There’s a trend called looksmaxxing that says appearance is everything, and optimizing it is just pragmatism. Apply that same logic to nonprofits and you get an interesting thought experiment: what happens when an organization goes all in on brand? And what happens when one deliberately strips brand away entirely?

This episode explores the spectrum between “brandmaxxing” and “debranding,” two extremes that most organizations will never fully inhabit but that reveal something important about how the sector thinks about visibility. Brandmaxxing means pouring maximum resources, attention, and intention into becoming the authority on your issue. Debranding means stepping back entirely, taking no credit, and letting the work dissolve into the ecosystem. The social impact sector has been structurally imbalanced toward the debranding end for decades, and the reluctance to invest in brand often masquerades as virtue. But humans are influenced by brand the same way they’re influenced by appearance, and refusing to play the game doesn’t make the game go away.

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Then there’s the question of who carries the brand. Institutional trust is in decline, and people increasingly follow people rather than logos. That creates real opportunity for individual-led storytelling, but it also creates a single point of failure. When a charismatic executive director leaves, they can take the organization’s identity with them. The key distinction is that the individual should be the channel for the message, not the brand itself. You still need to be yourself, you can’t be a shell spokesperson reading the company line, but the story you’re telling belongs to the mission, not to you personally.

The episode concludes that the instinct to stay behind the scenes, to say “I don’t want to add to the noise,” often feels like humility but is actually its own kind of arrogance. It’s the belief that you’re somehow above the game, that your work is too important for self-promotion. But if the work matters, it deserves to be seen. And opting out of visibility has real consequences that too many leaders aren’t honest with themselves about.

Episode Highlights:

[00:00:00] The looksmaxxing trend as a lens for brand strategy
[00:01:00] Defining brandmaxxing vs. debranding as a spectrum
[00:04:25] Where brand investment crosses into unhealthy territory
[00:06:25] Why brand is a game you have to play, even in social impact
[00:07:00] Debranding to make space for partners: noble or misguided?
[00:08:50] Trust through depth vs. trust through visibility
[00:11:00] “Putting ourselves out of business” and why that’s oversimplified
[00:14:00] People follow people, not logos: the Amanda Litman insight
[00:16:50] Truth and clarity over presentation and performance
[00:17:50] The single point of failure problem with individual-led brands
[00:22:00] The sector’s historical imbalance toward invisibility
[00:23:00] False humility and the arrogance of staying behind the scenes

Notable Quotes

[00:06:30]: “Humans are influenced by brand. You can be humble about it, but at some level, you got to realize you have to play the game.” Eric Ressler

[00:07:30]: “Is there valor in debranding to make space for others versus brandmaxxing, which would be like, take as much of that pie as you can?” Jonathan Hicken

[00:10:10]: “I would consider a meeting with a funder in a one-on-one situation an act of brand, because either you are going to show up in coherence with your stated brand values or not.” Eric Ressler

[00:10:45]: “Is there valor in debranding to make space for others, especially if we’re working with underserved communities?” Jonathan Hicken

[00:23:15]: “Get over yourself, because that is actually kind of a pretentious point of view. You’re not saying you’re not good enough. You’re saying you’re too good to put yourself out there.” Eric Ressler

Resources & Links:

• Amanda Litman, co-founder of Run for Something — Prior Spotlight episode.

• Amanda Litman’s Substack

• Run for Something

• Science, Solutions, Santa Cruz

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:00]: Eric, a couple weeks ago there was this SNL video going around where one of the SNL cast members was parodying a looksmaxxer.

Eric Ressler [00:00:10]: Oh yeah.

Jonathan Hicken [00:00:10]: Did you see this?

Eric Ressler [00:00:10]: The looksmaxxing.

Jonathan Hicken [00:00:10]: I instantly started thinking about our work and I was like, “Is there such a thing as brandmaxxing?” And then I was like, Eric Ressler is definitely a brand maxxer.

Eric Ressler [00:00:20]: I’m not even going to argue with that one. I think I should update my LinkedIn profile, Brandmaxxing for Social Impact.

Jonathan Hicken [00:00:25]: Please do that. So today I want to put you on the hot seat a little bit and I want to ask you some tough questions about brandmaxxing and see where we land at the end of it.

Jonathan Hicken [00:00:45]: So just to start things off, when I say brandmaxxing, I’m talking about an organization, its leadership, its board in some cases, going all in on brand. It’s almost like the Eric Ressler method, taking everything you say and implementing it a thousand percent. And being the best of the best at branding in every way that you and I have talked about on the show and more. Max resources, max attention, everything. And then the opposite end of the spectrum is debranding. So this is deliberately going out of your way to remove all elements of brand from your organization. Almost like a total decentralized play where you as the organization are taking zero credit for your work.

Eric Ressler [00:01:35]: Okay.

Jonathan Hicken [00:01:35]: Now, I actually don’t know that that exists in reality, but just as a thought experiment. This is what I mean by brandmaxxing and debranding. And so when I started to dig into the implications of these two ends of the spectrum, I came up with a whole list of questions for you. So the first is if you think about core philosophy of these two ends of the spectrum. One is humility. And we’ve talked about this in past episodes, not being visible could actually just come from this moral place of being humble and not wanting to get into it. And so success is really measured by just how embedded you are in the ecosystem of impact that you’re working on quietly.

Eric Ressler [00:02:25]: Okay.

Jonathan Hicken [00:02:25]: The opposite end of the spectrum is brandmaxxing where dominance and distinction is really the goal, where success is measured by becoming the authority on some particular kind of work. Do you see any reason when it comes to core philosophy not to be a brandmaxxer?

Eric Ressler [00:02:50]: So I love this, first of all. I just want to say that. I’m not a deep student of looksmaxxing, so I should get that out of the way. It keeps coming up on my feeds. So my understanding, please correct me if you have a different understanding about this. I’ve seen this SNL skit, but I haven’t actually watched it. Looksmaxxing from my understanding is this philosophy that appearance matters so much in modern culture, especially if you’re a young person, and that it’s a good strategy to become as attractive as you possibly can by any means necessary. I think the main dude, is it Clavakar or whatever? Something like that. He literally smashes his face with a hammer to restructure his jawbone.

Jonathan Hicken [00:03:40]: I haven’t actually witnessed that, but that’s the claim.

Eric Ressler [00:03:40]: So to me, that is clearly unhealthy from not just a physical standpoint, but it’s an unhealthy philosophy. So that’s where I would say, can you get there from a branding standpoint? Whereas getting close to that, but not quite that far, let’s take diet, exercise, sleep, things that will have a positive impact on your appearance, maybe even self-care and your apparel and things that matter and that are by any normal standpoint a good thing to do. I think there’s a version of brand that I advocate for. So I want to just put it on the table. I don’t want to say I’m a brand maxxer to the point where it’s like brand is the only thing that matters. Impact doesn’t matter at all. All you need to do is become the authority. You shouldn’t be humble about your work. So I think there is a version of brandmaxxing that, just like looksmaxxing or my understanding of looksmaxxing, can go too far.

Jonathan Hicken [00:04:45]: Okay. So there’s an unhealthy version of investment in brand. And so for you, what’s the line?

Eric Ressler [00:04:50]: So first of all, I would say I can’t think of a single example of that in the social impact space. Examples that I might think about would be maybe some personal brands where people have built up a brand about themselves that is so powerful that they basically become audience captured where they stand for something and they have so much financial incentive and audience incentive that they’re even maybe sometimes going against their own self-interest or going against their true core beliefs or identity. That would be an example of brandmaxxing gone too far. There might be some examples in the social impact space of orgs that, maybe in the political space where there’s so much investment in donor acquisition and just spamming people and you might consider that in the purview of brand or under the brand umbrella at some level, communication certainly, where as soon as it starts to be at odds with your identity and your beliefs and your values as an organization, however that shows up, to me that would go from strategically sound brandmaxxing to unhealthy short-term thinking brandmaxxing.

And I want to say one more thing that’s interesting in this thought experiment around brandmaxxing. There is, I think in the looksmaxxing community, this pragmatism element to it that I think it’s taken too far, but is rooted in some truth, which is that humans are influenced by appearance. And I think there’s a parallel in brand and in social impact, which is that humans are influenced by brand.

Jonathan Hicken [00:06:35]: And stories.

Eric Ressler [00:06:35]: And stories. And so when you talk about the other side, this humility side, you can do that, but at some level, you got to realize you have to play the game at some level. And I think there is a way to play the game in a healthy values-aligned way that is just a net positive.

Jonathan Hicken [00:06:50]: Okay. Let’s talk about debranding and brandmaxxing in the context of an ecosystem of work. So in the debranding example, when you’re a minimalist, maybe it creates more room for your partners to be more visible. So imagining visibility as almost this zero sum game. And so if you’re debranded, you’re creating more space for partners who are doing similar work to be seen or to be uplifted, especially if we’re working with underserved communities, communities of color, et cetera. Is there valor in debranding to make space for others versus brandmaxxing, which would be like, take as much of that pie as you can, even if it means that other people in your space are getting less attention?

Eric Ressler [00:07:40]: Well, I don’t think it’s a zero sum game. So in that example, I think it’s a good example. Let’s say there is an org that has a lot of attention already, go-to org for any given issue or community, and they want to debrand to make more space for other people. I think that is a worse strategy than leveraging their platform and their power and their brand prowess to uplift those other people and to give them a platform that they don’t have yet. And so you are still in that case as that parent organization or that more known organization, still brandmaxxing at some level, but you are sharing the power of your brand to uplift someone else in the ecosystem.

Jonathan Hicken [00:08:30]: Fair enough. So let’s move on to this idea of trust building. Because I think a lot of what we end up talking about in storytelling and positioning and messaging is building trust, building credibility. And so there’s a version of debranding where you are earning trust from the depths of your relationships that are happening in the 3D world and the real world, where brandmaxxing is almost more of a breadth play, a breadth of social proof where you are earning trust through scale of visibility and almost celebrity. Is there any qualitative difference in how we’re building trust on these two hypothetical ends of the spectrum?

Eric Ressler [00:09:20]: Well, I would push back a little bit on the idea that doing things in the 3D world is not brandmaxxing. I think that we think about the word brand and sometimes we think about your logo or your content, but brand is really how you show up in the world at large. And to me, when I think about building a brand, it’s about having clarity about who you actually are, self-awareness around that, a conviction about who you’re becoming. We’ve talked about these concepts recently a lot and they’re top of mind for me, and a consistent set of actions and truth to reinforce those things. And so to me, yes, that’s your brand identity system and your website and your messaging and your communications, but it’s just as much, if not more, important that your real world actions, small or large, reinforce your brand too.

I would consider a meeting with a funder in a one-on-one situation an act of brand in one way or another, because either you are going to show up in coherence with your stated brand values and your stated conviction as an organization or not. So to your point about breadth versus depth, or visibility versus those 3D actions, to me, those are just different strategies. And some orgs might need to go breadth first, some orgs might need to go depth first, but to me, that all fits into my new favorite brandmaxxing bandwagon.

Jonathan Hicken [00:10:50]: So in this work, we often talk about success looking like making our organizations obsolete. We’ve solved this big problem, so the world no longer needs us, high fives, we did it. And so I feel like in a debranding world, that goal is more achievable because you’re integrated systematically and if your brand never really existed, you can just disappear and the world goes on. Whereas in brandmaxxing, we’re almost looking for a more capitalistic market leadership. And so can you just disappear and say that you’ve solved the problem, now your brand no longer exists? Are you caught in needing to sustain your brand?

Eric Ressler [00:11:40]: That’s a good question. To me, I think about brand as a critical pillar for an organization. So I could ask that same question about if you’re operations maxing or if you’re culture maxing, does that mean you can’t spin down? To me, this is just a good sound business investment. And if not done well, you probably won’t ever get to the point where you can spin down because you haven’t been able to make that impact. Now, of course there’s going to be some exceptions to this, but I also think that paradigm of “we’re putting ourselves out of business” is a bit of a misnomer or oversimplification because usually the problems that we are solving are fluid, they’re not fixed, and usually they’re big wicked problems. And so you might solve one part of it, but there’s certainly another aligned problem that you are probably going to be well fit to solve as well.

And now you have momentum, you have experience, you have a team of people who are aligned, who are already in motion. So you’re probably better fit to go pivot as an organization than to spin down and hope someone else spins up for that next problem. Again, probably some caveats, probably some examples where, “Oh, we fixed that one problem and that one community and now we’re shutting down, it was great.” But I think that’s pretty uncommon too.

Jonathan Hicken [00:13:00]: Yeah, I think that’s fair enough. And I also think that some of these problems, I think of a bell curve and if your organization’s successful, maybe you’re just shifting that bell curve, but there’s still ends of the bell curve that you can continue to work on.

Jonathan Hicken [00:14:05]: The other theme that comes up for me when I think about debranding and brandmaxxing is this idea of something that I think came up in an interview you had with Amanda, forgive me, I’m forgetting her last name.

Eric Ressler [00:14:15]: Oh Amanda Litman

Jonathan Hicken [00:14:15] About people not following brands, but following people. So okay, if we cross reference brandmaxxing with individual-led brands rather than organizational-led brands, is there a world in which you’re building up an individual so much that it actually becomes a fragile point of risk for the organization?

Eric Ressler [00:14:45]: Absolutely. Yes. I think this is actually a really important point because Amanda’s totally right, first of all, and she comes from politics and so a lot of her point of view, she has a really interesting point of view, which is why I was so excited to have her on the show because she is often talking about individual political candidates and politics at large in America, and she’s also the executive director of Run for Something, which is a brand that helps young people and everyday people run for office. And so she has a unique vantage point in that she is both building a brand, she’s building a personal brand, and she’s helping. She has thoughts, ideas, and opinions, and recommendations around how to run successful political campaigns and what the next generation of political candidates needs to look like. And I think her point that you reference is that newer generations especially, but just culture at large right now doesn’t have the same relationship that we used to to brands.

And especially Fortune 500 brands or big corporate brands, even institutions as brands. You see this so much in the academy or science or political institutions where there’s such a degradation of trust that has happened in those institutions that used to just be like, “Of course we’re going to do what the CDC does.” And now it’s like, “Well, what does my Instagram influencer think about vaccine schedules?” That’s a huge cultural shift, not probably for the best in many cases. So what does that mean in terms of brandmaxxing versus debranding to take it back to our conversation? I think it just means the nature of how brands show up in culture has changed a lot. I think that in a positive light, it means that brands need to be more, I’ll use some buzzwords here to point at a concept, human, authentic, these are the things you hear, less polished, more just straight up and real and less of a PR-based play and more of just... I think it’s less about presentation and performance and more about truth and clarity.

Those are the words that I’m really thinking about a lot right now when I’m thinking about how we brand organizations, helping them deeply understand who they are way, way, way past surface level. That’s becoming more and more important, crystallizing that vision and being really good at communicating that in a way that people can get instantly. And then yes, also having some people-powered stories behind that or people representation so that it’s not your PR spokesperson getting a press release out. It’s often the executive director or your development director or a staff person who’s now responsible for that message.

Jonathan Hicken [00:17:35]: The risk I see, if you take these two concepts of brandmaxxing and individual-led brands, the risk I see is that you get the single point of failure where, especially if the individual who’s most visible is the executive director or CEO, because one mistake and that whole brand comes crashing down. If you have invested a lot of brand equity and time into this individual and they leave or they make a mistake, you’re toast.

Eric Ressler [00:18:10]: Totally agree. And I’ve seen this happen over and over again. Even before personal brand building was the hot topic where even just a super charismatic leader or board chair or executive director who was responsible for telling the story, who was really good with people, who had a good network, who was really good at fundraising, all of a sudden they’re onto the next thing and the org’s got the rug pulled out from underneath them. So I think we have to be careful about that. And I still believe strongly that as much as we should have more of that human, authentic, focused storytelling and yes, more coming from executive directors or CEOs and staff, we do have to be careful not to over-index on that to the point that there’s no support behind it as the brand. You can do both at the same time.

And Amanda’s doing a really good job of that. She’s building a really strong personal brand. She’s an author also. She has her own personal Substack. She talks about her work, she talks about her life, she talks about parenthood, and she’s at the same time building up the Run for Something brand too. If Amanda were to leave, it would be a big thing for their brand probably, but she wouldn’t be leaving behind an empty shell either. So I think there is some pragmatic balance that you have to strike there.

Jonathan Hicken [00:19:25]: Yeah. I mean, obviously we want to tell human stories and I think all of the listeners can agree that’s important. But there’s this nuanced distinction between telling human stories and centering your brand on an individual that works there.

Eric Ressler [00:19:40]: Yes.

Jonathan Hicken [00:19:40]: Frankly, I’m thinking about it in my own work because now I’m hosting a podcast for the Seymour Center that is arguably the most visible thing that we’re doing that’s outside of our building. And so I think about that. I’m like, I don’t want to put my organization in a risky spot because now so much of the attention’s on me. At the same time, I know that raising money, people give to people, and I want donors to get to know me. So there’s this dance.

Eric Ressler [00:20:15]: It’s a dance. It’s a healthy tension, I would say, when done right, where people want to give to people, people want to follow people. I don’t think that means you can’t also build a strong brand, but I do think it means you have to be intentional about that. So you’ve built this studio, you’ve built this strategy and this workflow around creating content. If you were to leave or God forbid, get hit by a car or something and disappear all of a sudden, it would be a transition, but you’ve also built some infrastructure out that someone else on the team could come in and take over. And I think also the distinction is the story is not about the person. The story is delivered through the person in a personal human way.

Jonathan Hicken [00:21:00]: That’s a cool distinction there, that the individual is the channel by which the message of the organization is delivered. That’s a cool way to think about it.

Eric Ressler [00:21:10]: But the challenge there is not at the expense of your personality and your humanity, right?

Jonathan Hicken [00:21:15]: Like I still need to be Jonathan.

Eric Ressler [00:21:20]: You still need to be Jonathan, right? You can’t just be a shell spokesperson. I think that’s the thing that doesn’t work anymore where you’re just like, “I’m going to put on my suit and tie and say the company line.” That’s not personal brand building. That’s not the kind of message or story or delivery method that’s working in our current media environment.

Jonathan Hicken [00:21:40]: Ultimately, all of this is about balance, right? I mean, debranding and brandmaxxing, we set up the premise with these two extremes, right? So by nature, we’re going to fall somewhere in the middle, but also that’s really the reality of it. And from my executive director perspective, that’s just running a business. You got to balance all of the levers. And so obviously debranding and brandmaxxing to the extreme are really not even feasible, but the sector at large has been unbalanced or imbalanced, excuse me, for decades or maybe even since the beginning. And so your voice in this sector, I think is really important because you’re advocating for a particular version of running social impact, which prioritizes brand really heavily, but I think you’re pulling the whole sector to become more balanced, which I think is ultimately healthy.

Eric Ressler [00:22:30]: Yeah. And one thing I would share as I’ve become more public in this work and through this podcast and other efforts is, I don’t want to diminish that. I also, I’m an introvert. I don’t love being on camera. I hate speaking in front of large audiences, et cetera. And I think sometimes we have almost this, we talk about this a lot, this pride of being behind the scenes. Or sometimes I see this with clients, and I think we’re going to do an episode more on this, but I want to tease it out a little bit, where there’s this, “Well, I don’t want to add to the noise. I’m not important enough. I don’t have a strong enough point of view.” And honestly, I’ve started to come around to: get over yourself, because that is actually a pretentious point of view when you think about it, because you’re saying it’s not really that I’m not good enough. It’s almost like I’m too good to put myself out there in that way and I don’t want the attention. So it’s this weird... And this is a transition that I’ve had where it’s just like, you’re not so special that you can’t also do this. I don’t know if I’m making any sense.

Jonathan Hicken [00:23:40]: You’re totally making sense. The way I would interpret that is this hubris that if all of a sudden I add my voice to the mix, everybody’s going to be focused on me.

Eric Ressler [00:23:55]: Right. And that’s the thing, no one really cares that much. Your stuff is not so special that it can’t also be in the fray. And I think the way that I would just think about this is that you need to be out there telling stories. You need to be out there. If you’re doing this work, it deserves to get its message out into the world and you are doing a disservice, and this idea that I don’t have anything to say or that we’re going to bring too much attention to our mission. There’s just a certain amount of this that’s like, look, if you’re going to be in the game, you got to play by the rules and the rules are dictated by human psychology and just get over it and just do it. That’s something I’ve been learning a lot more because I was that person. I was like, “I don’t want to get in front of a camera. I don’t want to have attention on me. I don’t want to be in the spotlight.” And when I really started to unpack that more deeply and do some self-reflection, it was that, yes, I had imposter syndrome, I was worried about flubbing something, but also I was like, “I’m better than that. I’m too good to play this game. I don’t need to.” And it’s just like, you don’t need to, but be clear about the consequences in our current world about what you’re giving up by not doing that.

Jonathan Hicken [00:25:05]: Well, look, I hope that you do change your LinkedIn profile to Chief Brand Maxxer of the Social Impact Sector. No, but I really, really appreciate it. And I think that frankly, you’re pulling the sector in a really important direction and I’m glad to be a part of it. So thanks for unpacking this brandmaxxing concept with me today, Eric. Anything else?

Eric Ressler [00:25:25]: Thank you for giving me my new LinkedIn profile.

Jonathan Hicken [00:25:30]: All right, that does it.

Eric Ressler [00:25:30]: Thanks, man.

Jonathan Hicken [00:25:30]: Thanks.

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Every major technological paradigm shift has broken society before it fixed it. The printing press gave us the scientific revolution, but it also gave us witch hunt pamphlets. Radio connected millions of people, but it also let demagogues broadcast hate into our living rooms. The television brought the world closer, but it also turned politics into performance. And now we have the internet and social media and AI, and the pattern is repeating, but the speed is meaningfully different.

Now one person can fabricate a story and reach hundreds of thousands of people in mere hours or minutes. AI can generate video that’s basically indistinguishable from reality. And all of the platforms that are delivering all of this to us, they’re basically engineered to reward whatever makes us the most outraged, angry, and divided. For leaders in the social impact space, I believe this is an existential problem. If the people you’re trying to reach don’t believe anything is real anymore, your message can’t land and your brand doesn’t matter and your mission falls flat.

So what do we do about it? To explore that question, I wanted to talk with Joel Breakstone. Joel is the co-founder and executive director of the Digital Inquiry Group. They’re a nonprofit that spun out of Stanford to tackle one of the most urgent problems of our time. How do we help people tell fact from fiction online? His civic online reasoning curriculum has been downloaded millions of times across all 50 states, and it’s built on a deceptively simple insight borrowed from professional fact checkers.

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Episode Highlights:

[00:01:55] Was the internet a huge mistake?
[00:05:15] How algorithms and human psychology feed each other
[00:06:50] Is the internet fundamentally different from past paradigm shifts?
[00:08:30] From Stanford History Education Group to the Civic Online Reasoning curriculum
[00:12:35] Fact checkers vs. PhDs vs. Stanford freshmen: who evaluates sources best?
[00:15:20] Lateral reading: the counterintuitive skill that changes everything
[00:16:40] Why digital literacy mandates keep failing without materials
[00:22:40] What a “driver’s license for the internet” might look like
[00:26:20] The collapse of institutional trust and rise of influencer trust
[00:31:05] AI as both threat and tool for digital literacy
[00:38:35] The “.org means trustworthy” myth and why evidence-based guidance matters
[00:41:50] What keeps Joel optimistic despite the scale of the challenge

Notable Quotes:

[00:11:25]: “The myth of the digital native is very much a myth. Young people, like the rest of us, need help making sense of the unbelievably crowded and confusing landscape that we encounter when we go online.” Joel Breakstone

[00:27:30]: “It can become really easy to just throw your hands up in the air and say, ‘Nothing’s real. I don’t know what to trust.’ And that is a really dangerous place for us to end up because it plays into the hands of authoritarians. They want people not to know what to believe.” Joel Breakstone

[00:24:30]: “This is not just a couple of skills. It’s an orientation to how you make sense of new sources.” Joel Breakstone

[00:35:50]: “Early arbiters of truth were often religious bodies. In modern history, that became media organizations and institutions and the academy. With the dawn of the internet and social media, arbiters of truth became algorithms. And now AI is just a new form of a new arbiter of truth that we have to question just like we questioned all of those others.” Eric Ressler

[00:32:50]: “AI is not an oracle. AI is drawing information from somewhere. Students need to understand that information comes from somewhere. It’s not free floating.” Joel Breakstone

Resources & Links:

• Digital Inquiry Group — Joel’s nonprofit, spun out of Stanford, developing free digital literacy curriculum and research

• Civic Online Reasoning (COR) Curriculum — Free curriculum teaching lateral reading and source evaluation skills, available to anyone with a free account

• Verified: How to Think Straight, Get Duped Less, and Make Better Decisions about What to Believe Online — Book by Mike Caulfield and Sam Wineburg (University of Chicago Press, 2023)

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:40]: Okay, Joel Breakstone, thank you so much for joining me today.

Joel Breakstone [00:01:45]: Oh, it’s my pleasure. Thanks for having me.

Eric Ressler [00:01:45]: So lots to talk about today. Really a big fan of your work and when we worked together on civic online reasoning, I actually learned a lot about how to be a good digital citizen, something that I’ve been since I was really young. The first question I want to ask you is half in jest, but also not totally. Was the internet a huge mistake, Joel?

Joel Breakstone [00:02:05]: No, I definitely don’t think so. I think it’s an incredibly powerful tool and we are better for having access to it, but certainly our work shows that we need to help people, and our work focuses particularly on young people, to understand how to use that incredibly powerful technology well.

Eric Ressler [00:02:30]: Yeah. So I asked that question half in jest because I do actually think deeply about this at times where so much of my life has been shaped positively because of technology and specifically the internet to the point that I run basically a creative agency, a digital agency that maybe wouldn’t exist without the internet in one form or another. We build a lot of digital tools and websites as well as brands and strategy. And yet I’ve seen in real time, the internet, maybe a little bit more so specifically social media, really negatively impact society in pretty meaningful ways to the point that it’s influencing elections, it’s influencing dialogue around really big picture things, even war. Can you talk to me a little bit about how the internet went from this really good faith, incredible experiment where we could suddenly be connected instantly to where we are today?

Joel Breakstone [00:03:30]: I don’t know if we can trace the entire history briefly. I think that what has happened is that there has been a proliferation of deeply problematic content online and we have an information ecosystem that rewards people who can capture attention and that within that attention economy, bad behavior is often rewarded. That ranges from the ways in which algorithms are tuned to hold us on platforms and to make us pay attention to whatever it is, even if it’s not good for us or if it’s harmful for young people, and to spread deeply problematic content and dangerous and damaging content as well. And that has only intensified in recent years. And so without a doubt, there are fundamental issues that we need to address to ensure the wellbeing of young people and all of us, as well as to strengthen the democratic systems at the heart of our country and nations all around the world.

And so for sure, the stakes are very high and the need to address this threat is very significant and it needs to be a whole of society approach. Not one sector is going to be able to take on the set of ills that we are being confronted with. Instead, we all need to be figuring out ways to try to address the problems that have become all too apparent.

Eric Ressler [00:05:15]: So I want to hold a little bit on this. Specifically, you mentioned that the algorithms reward bad behavior. And I think that I’ve been curious about, and I don’t think this is probably an either or situation, but how much of that is intentional because of algorithmic tuning from big tech companies to reward engagement basically at all costs versus how much of that is just a negativity bias in human psychology?

Joel Breakstone [00:05:45]: I think there’s certainly some of both. And those two things feed into one another to create a landscape in which people get rewarded for that bad behavior and they can grow their following and their clout online by propagating problematic content, by being rage merchants. That is, as you note, a fundamental piece of human psychology, that we have that innate reaction and we engage, and that engagement is what platforms want. They want people to spend time there and to be engaged. And so people have responded to those incentives and we’re all worse for it.

Eric Ressler [00:06:40]: Yeah. So I want to kind of... Your background is actually as a historian originally, if I’m getting my notes right here, working out of Stanford and Dartmouth before that. Is the internet uniquely different than other major paradigm shifts in technology and communications? For example, when the printing press came out, there was all kinds of mis and disinformation in pamphlets and the witch trials. And this was also a problem even before that technology. So is the internet unique in that it’s just at scale and at a speed that is meaningfully different than past paradigm shifts?

Joel Breakstone [00:07:20]: Well, I think you’ve noted something that’s important. That this is not a new phenomenon in terms of people spreading inaccurate, misleading, and dangerous content. That has been around for a very long time. But I do think that in the present moment, the speed of dissemination and the ease of dissemination is fundamentally different. When the printing press came out, everybody didn’t have a printing press in their pocket that could reach across the world in moments. That presents a fundamentally different reality. And with the advent and rise of AI and the power of those tools now, anybody can create incredibly lifelike images and videos that can be spread all across the world. And that also is fundamentally different. The power of the technology is hard to get our heads around.

Eric Ressler [00:08:25]: Yeah. And I definitely want to spend some time on AI in a little bit, but before we get there, I’d love if you can tell our listeners a little bit about how your work with Stanford History Education Group led to the creation of COR, or civic online reasoning, which is essentially free curriculum to help combat this issue of mis and disinformation, but more broadly digital literacy. So can you at a high level outline, how did that come to be? What was the research showing? What did you learn from that? And what’s the intervention that you guys have created to try and combat the negative downstream effects of what you found?

Joel Breakstone [00:09:05]: Yeah, absolutely. So as you noted, our organization was called the Stanford History Education Group, and we were based at Stanford’s Graduate School of Education. And our focus was primarily on history education. I’m a former high school history teacher and my colleagues all had backgrounds in history education. We were making document-based history lessons and assessments and giving them away for free online. And just over 10 years ago, we were approached by a foundation, the McCormick Foundation based out of Illinois, and they wondered if we could do some similar work to what we had been doing around history assessments, making short tasks that asked students to evaluate real sources and do the same thing in the area of digital literacy, that they were funding projects that focused on helping students to navigate online spaces. And they wanted to have better evidence about whether or not those programs were effective in helping students to be more discerning.

And so we began to make short tasks that asked students to evaluate unfamiliar online sources, native ads, unfamiliar social media posts, websites that were created by public relations firms and asked students to make sense of them. And we gave these tasks to students ranging from middle school to college all across the country. And we saw a really disturbing result, which was that across the board students struggled with even the most basic tasks. They couldn’t distinguish sponsored content from a news story. They didn’t know that a PR firm was behind a website that was purporting to provide nonpartisan research-based evidence about public policy issues. They were easily misled by social media videos. And so this idea that because young people have grown up with digital devices, that they are better equipped to make sense of the information that those devices provide just really did not hold up. That myth of the digital native is very much a myth. Young people, like the rest of us, need help making sense of the unbelievably crowded and confusing landscape that we encounter when we go online.

And so yeah, our research revealed deep problems for students in making sense of digital content. And we released our findings, more than 7,000 student responses we collected, in November of 2016, shortly after Donald Trump was first elected president. And there was an enormous amount of interest in the question of misinformation and how to be a little wiser on the internet. And so we heard many, many inquiries about, well, what do we do about this problem? Your research shows that students are struggling. How do we help them do better? And so we wanted to try to identify expert practice. What are more skilled approaches to evaluating online sources? And so we did a research project led by my colleague, Sam Wineburg and Sarah McGrew, where we asked three groups of people to evaluate unfamiliar sources.

And we thought each group might be particularly well suited to evaluate sources that they hadn’t seen before. And those three groups were Stanford University freshmen, young people in the heart of Silicon Valley who are online all the time, and many of whom will go on to found and work at tech companies, and then historians, people who have PhDs and are evaluating sources for a living. And then finally, fact checkers from the nation’s leading news outlets, people who are responsible for ensuring the accuracy of information that those organizations publish. And what we did was to present them with online sources and to record their screens as they showed us what they would do to try to decide whether or not to trust those sources. And there were some really striking differences across those three groups. The professional fact checkers were way better than the students or the academics at evaluating unfamiliar sources.

And the thing that distinguished them more than anything else was when they came across an unfamiliar source, they almost immediately left it. They didn’t read it carefully or closely. That’s what the students and the academics did. They did what helped them to be successful as students and as researchers. They read carefully and closely. But on the internet, that often could lead you astray. One of the tasks we had people complete was to evaluate an article from the website, minimumwage.com. And it says that it’s a project of the Employment Policies Institute. And the Employment Policies Institute has a .org website and it says that it engages in nonpartisan research and that it’s a nonprofit organization. All these things that sound good and that the students and the academics read carefully and closely. In contrast, the fact checkers did something fundamentally different. They didn’t read the article carefully.

They left it and they turned to the broader internet and opened a new tab in their browsers and searched for information. And by doing that, they found out that this is a website that is a front group for a public relations firm that’s working on the behalf of people who want to keep minimum wages lower, and that this is not a nonpartisan effort. In fact, it’s a very concerted effort to influence public policy. That information is readily available if you go looking for it. And that’s what the fact checkers did. And what we did was to try to distill down their strategies. That move of getting off an unfamiliar page we refer to as lateral reading, of leaving an unfamiliar source and opening up new tabs and reading across them rather than staying on a single page and reading vertically, which often works well in a print environment, which is why it helps students get into Stanford and academics get their PhDs, but is not nearly as useful in online spaces.

And so what we’ve tried to do is to distill those strategies that we saw the fact checkers deploy effectively into a set of tools to teach students. And that’s at the heart of the civic online reasoning curriculum, which is a set of resources that teach these skills like lateral reading to students and provide them opportunities to practice them with real sources from the spaces that we know students are spending their time, TikTok and Instagram, so that they have opportunities to practice and to build their capacity to sort fact from fiction when they are on their devices.

Eric Ressler [00:16:35]: So to me, this skill, let’s say broadly under the umbrella of digital literacy, seems like the single most important skill to teach young people in the world in this moment. And yet you guys have free curriculum that you’re providing. There’s more and more tools out there. There are these checklist tools that you have, I think, rightfully called out as being inadequate or flawed, even if the intention is right. There’s now a bunch of state legislation across multiple states in America. There’s other legislation in other countries attempting to solve this problem, but it’s not working, at least at the scale and the depth that we need it to work. And I don’t mean that as a criticism of your organization. Obviously, as you mentioned at the beginning, this is going to take everyone coming together to solve this problem, but what isn’t working about this intervention? Because my sense is that we have the tools, the methodology, the technology. We understand how to solve this problem practically, but it’s not being solved nearly quickly enough. So what’s getting in the way from your perspective?

Joel Breakstone [00:17:45]: No, I think that’s exactly right. We have evidence that these approaches can work. Our studies have shown that by teaching these skills to students, we see them improve. We’ve engaged in research ranging from studies across an entire urban school district to interventions in college classrooms. And those results have been replicated by other researchers, both in the United States and abroad in Canada and in Italy and Sweden. So yeah, there is clear evidence that this is not an intractable problem. We can move the needle and improve students’ ability to discern, and the public at large, that this isn’t just restricted to young people. I think the key problem is, especially when we think about educational settings, is that there is not a school subject called digital literacy. There is not a home for this work in the school day. And so we can create new legislation that calls for the teaching of digital literacy, but until there is a way to make it a meaningful part of students’ education, we’re not going to see much progress.

This isn’t something that can be solved for in a single workshop. Students need practice and opportunities to reflect with their classmates and their teachers about how to do these strategies effectively. And so we believe that the way forward is to find ways to build this kind of instruction into the existing curriculum. So not trying to create a brand new version of the school day, but instead find ways to work within the curriculum as it exists. So for instance, if we’re thinking about the history curriculum, how might we have students investigate a TikTok about an issue related to reconstruction? For instance, the origins of the term grandfather clause. You can find very interesting sets of videos about that online, and we could teach about that video quickly in a broader lesson on a topic that teachers are already spending time on. Everybody in US history is teaching reconstruction.

We could spend a little bit of time by doing a quick activity at the end of a lesson and provide opportunities to practice. So really finding ways to weave these materials into the existing curriculum. And that speaks to what I would say is also the broader problem, which is that there have not been parallel efforts to create the resources and professional development for educators to implement these mandates. By and large, these legislative mandates have been mandates without materials. And teachers and schools and districts are being left to try to figure out how to address this incredibly challenging problem on their own. And so if you believe that this is a very pressing problem for young people and our society as a whole, we need to invest in developing materials that will make it as easy as possible for educators to enact this important type of work in their classrooms and to support educators in doing so.

This is new for everybody. This is not the kind of instruction that most teachers learned about when they were preparing to become teachers. And so we need to ensure that we are not just loading another responsibility on the back of teachers without giving them the support to do that well. So both finding ways to build this kind of instruction into the school curriculum and then making the materials to do that well.

Eric Ressler [00:22:35]: There’s so many ways I think we could approach this, and I appreciate your pragmatism and always have in terms of realizing creating an entirely new school day is going to be difficult. And yet at the same time, we have done that for other really important topics. And even something like if we think about a parallel of getting a driver’s license in the United States, everyone doesn’t get to just start driving all of a sudden. You have to actually get a license, take a test, do practical application, and that can happen through high schools, but you can also do it third party. You don’t have to do it through the school system. If you could wave a magic wand and redesign how this all worked and put aside all the barriers of changing the school system and the academy, what would the absolute right way to do this look like in your opinion?

Joel Breakstone [00:23:30]: I think that the elements that we’ve seen from our work is this kind of effort has to be ongoing, that this is not a simple, here is a small set of strategies, we told them to you and now you are ready to be a much more discerning consumer of online information. No, it’s like anything else, any skilled practice, you need opportunities to try it out and to make mistakes and to learn. And importantly, you need to have a way in which to build that capacity over time. And so we need to think about how to make that a long-term strategy so that it’s not just, “Oh, I learned that once and now I’m done with it.” Instead, it’s a disposition towards information. I think that’s a key understanding. This is not just a couple of skills. It’s an orientation to how you make sense of new sources.

It’s asking, “What is this thing? Do I know what it is?” And even if you aren’t able to track down exactly what it is, just having that question of saying, “I’m not sure,” allows you to have a very different engagement with online sources. Just that pause can make a huge difference rather than just accepting at face value, which is what we’ve seen so often. Seeing is believing.

Eric Ressler [00:25:10]: Yeah. And I think that I can relate to that. I think through our work together, I have learned to practice lateral reading. And so whenever an unfamiliar source or claim is presented to me, the very first thing that I do is go to Wikipedia or do a web search. And I know that’s not an infallible strategy, but what I’ve found is that even people who I’m close friends with or in my family who should know better, and I fall into this too, I think everyone has fallen for some version of mis or disinformation, even probably all the time without even realizing it. But I noticed that most people just go by vibes more than anything. Does it reinforce a belief that I already have, I think, is something that we all need to be wary of.

And does it just feel legit even if it’s not? And I think one thing I’d love to tie in that I think is relevant to anyone doing this work in the social impact space, whether you’re focused on digital literacy or just any kind of social change, is the relationship between information, disinformation, attention, trust and credibility, that whole ecosystem. And I think that the thing that I’ve noticed is that especially in the last five-plus years, there’s been a massive shift in the general public away from trusting institutions, trusting organizations, trusting the government, and a lot of that trust has been reallocated towards individual people, either people directly in their lives or more and more individual influencers on the internet. I’d be curious to hear how you think about that problem and whether you think that is just an inevitable shift in our modern media ecosystem, or if there’s something that we should be resetting back to trust in some of these broader institutions that needs to be taught as a skill.

Joel Breakstone [00:27:15]: Yeah. I think it’s absolutely a shift of increasing distrust in institutions and more broadly, a distrust in everything, that as problematic content has spread and as AI slop has proliferated, it can become really easy to just throw your hands up in the air and say, “Nothing’s real. I don’t know what to trust. There’s nothing there.” And that is a really dangerous place for us to end up because it plays into the hands of authoritarians. They want people not to know what to believe. And then they say, “The only thing you can trust is me or my organization.” And that’s a problem. We want people to be empowered to make decisions that are based on evidence and are in the interests of them and their communities. And so it’s crucially important that people have the tools to seek out information so that they can make good decisions.

If we end up in a place where people don’t think they can do that, it’s a pretty bleak future. So without a doubt, it’s really important for us to make clear that there are strategies for finding better information and that you can use them. And that, as you note, it’s not infallible. This is not a foolproof effort, but if you practice some of these ways of reasoning, you generally end up in a better place rather than just accepting information at face value and certainly in a better place than saying, “I can’t know.” And so it’s impossible to know because then you’re not informed and you aren’t going to be empowered to be a civic actor in our shared democracy. And so it’s really important to be able to both make that reality apparent to people and then to equip them with tools to help them to find the information that will allow them to make decisions that are aligned with their own interests.

Eric Ressler [00:29:30]: Yeah. I mean, I think the result of this that I think we’re all becoming more aware of and hopefully are working as a culture, as a society to shift, is that now we all live in these siloed ecosystems from an information standpoint. You used to have the three TV channels or your local news, and that’s how you got your information and your facts, or you talk to your friends at the school board or at the bar or wherever. And if you had a really weird, wacky idea, you’d bring that to a social situation and someone might be like, “Hey, Eric, that’s a weird idea. Where’d you get that from?” And now you can find an entire community who’s like, “Yes, that idea is exactly right.” And so these weird, unhealthy, not evidence-based ideas are able to proliferate and flourish in a way that before this ecosystem and the ease at which we could all connect existed, basically we just get shut down by normal human culture.

And so with all of that in mind, I think the thing that I struggle with is we get into this situation where it’s like, okay, well, I don’t know who to trust. I can’t trust anyone. You hear that a lot, but then you see the behavior and people go to, “So I’m going to trust this Instagram influencer,” which to me seems like the exact opposite conclusion that you should draw from that ecosystem. So I want to bring this into a couple threads before we wrap up here. One, we should definitely go and talk more about AI because AI is, in my opinion, a double-edged sword around all of this because I think it has potential in an optimistic way to solve some of these issues, but it also has potential in a much more pessimistic way to just proliferate them even further. So let me ask you one question I have.

I mentioned earlier that my version of lateral reading used to be Wikipedia web search. My new version of lateral reading is to do deep research on a topic and have AI essentially do that for me. And I’m aware of the potential issues there. And I’ve watched one of the things that I use Claude to do a lot of research and it will show you citations. And I always check who are they actually referencing. And what’s interesting is they will reference, or the tool will reference, sometimes partisan sources. But if I were to go do a web search, I would also likely find partisan sources and would need to get into this lateral reading, never-ending spiral where it’s like, “Well, I’m going to go do another search and find another source, but now that source is also potentially unfamiliar.” So I guess the question really is, how do you see AI affecting this? What are the ways that AI might be a helpful tool to counter some of this mis and disinformation and just digital literacy in general and what are the ways that it’s going to probably be very problematic against this issue as well?

Joel Breakstone [00:32:30]: So the first thing is that it would be easy to say, well, your whole approach to lateral reading is irrelevant now because who’s on a web browser anyway, who’s doing a search? But the reality of it all is that it still is important to think about where information comes from because AI is not an oracle. AI is drawing information from somewhere. And as we think about how to move forward with teaching these ways of reasoning to students, that’s at the heart of it. Students need to understand that information comes from somewhere. It’s not free floating. And when we are encountering AI generated content, whether that is the AI summary when you use a search engine or if you are going directly to a chatbot, we want to know where the information is coming from. We should just not accept an AI generated response because it is polished and seems convincing.

We need to think about exactly what you said, which is what are the sources that they are providing. And that is lateral reading ultimately, of using other sources to become better informed about a claim or a person or an organization. That has to be part of the process. And sure, many of them are going to be partisan. That’s fine. That’s the nature of the beast. We just need to take into account what is the perspective of those sources and to be thinking about what are higher quality sources also. And that comes back to the issue about influencers and who to believe online, is to think about the authority of a source. Why is this person in a position to know on a given topic? And there are a variety of ways to think about that. And also, what was the process that was used to create this information?

Were there processes that helped to improve that ultimate product? Were there editors involved? Are there experts who were consulted? Are there checks to correct mistakes if they happen? Why is it important to have a correction policy if you’re a news organization or if you are an academic press to think about the review of something before it’s published or peer review? Again, none of these things are infallible. There are deep problems with news organizations and with academia, but it’s better to have processes to ensure the quality of information than not. And so to really think about what kinds of sources would you want to use is a part of consulting and using AI for these purposes. It just needs to be addressed that we can’t just think, “Well, it’s a good result,” without saying, “Well, what are those sources?” And if they’re not linked, to ask for them, and also to think about prompts that push the models to provide sources from particular types of organizations or people. Those are all tools that can lead to better results.

Eric Ressler [00:35:45]: Yeah. And I think about this in the sense of, again, these paradigm shifts. So early arbiters of truth were often religious bodies, if we go back far enough in history. In modern history, that became media organizations and institutions and the academy. With the dawn of the internet and social media, arbiters of truth became algorithms. And now AI is just a new form of a new arbiter of truth that we have to question just like we questioned all of those others as well. But I am optimistic with, again, the right skills that AI can actually be a really good force for good for this. And I’ve, again, learning through you all, have been trained on lateral reading and click restraint and some of these other core disciplines and skills. And I’ve been able to translate that into AI tools in I think a positive way where often even just to your point around prompting, when I’m learning about an issue that I’m confused about and I hear different partisan opinions, it’s like, “Hey, I’m interested in learning about this issue. What are the different opinions about this? Is there consensus about this at this point? Who are the sources that I should be looking at to learn more about this?” And it gives me a really good starting point very rapidly, whereas before I would’ve had to do all of that research on my own. Often in these deep research, either through Perplexity or Claude or ChatGPT or any of the big players, they’re looking at three, four hundred sources. I don’t have time to do that. Now you could say, is 400 sources any meaningfully better than the top 20? I don’t know. That’s an open question for me, but I’ve found that with intentional thought and using the tools wisely, they could potentially really help with this. Do you find that to be true or are you more skeptical about the technology?

Joel Breakstone [00:37:35]: I think there’s real potential. And I think that we’re in a moment where we need to do careful research in classrooms. For us as an educational nonprofit, we want to have evidence about what are practices that work. We think that there is real potential for being able to use these tools to verify viral claims on social media and to quickly surface fact checks, that these tools can potentially work very well in that regard. But just as we set out to initially identify what are best practices for verifying content in a space when we’re primarily just using search engines, we need to do the same now. And we need to make sure that we are providing guidance that is grounded in evidence. I think one of the shortcomings of our approach to teaching students to navigate the internet was too often the guidance wasn’t based in good evidence and there were really negative consequences.

Countless students learned that .org websites are more reliable ones, even though there is no evidence for that whatsoever, but it became just a bromide that everybody learned. So going forward, as we think about this new technology, we need to make sure that our educational approaches have some real backing for them. But without a doubt, there’s real potential. And I think your phrase was how to use AI wisely. And I think that’s what we need to be working towards, is to prepare people to understand how the technology works and what are strategies that will help them to find information. And importantly, that they as individuals are part of that process. It comes back to that same idea of empowering people to find information, not to simply say, “Well, in ChatGPT or Gemini or Claude, I trust.” Instead, it’s, how can I use this tool to become better informed?

And there’s incredible power there and we should think about how we can harness it well.

Eric Ressler [00:39:50]: Yeah. And I think a lot of the same foundational principles can be applied to AI use responsibly. It’s just not blindly trusting things, especially because AI is great at confidently being wrong. And honestly, in my use, I find that the newer models are getting better at that. And you see them in the benchmarks, what they call hallucinations are dropping, but they’re still there and they can be not only confidently wrong, but very convincingly confidently wrong too, because they can articulate things in a way that sounds intuitively right and evidence-based, but then will make up citations. You see this tragically showing up in scientific reports. You see it tragically showing up in government-funded research. And so there are real risks, not to mention all of the ability to create AI slop and propaganda at scale more rapidly than ever before, obviously deepfakes and AI-generated video.

So we’re getting into a very sci-fi moment as a society where it’s going to be more and more difficult to know what is truth and what is real, especially within our own information silos and our fragmented ecosystem. And so to me, these skills are becoming existential for society in a way that I applaud Digital Inquiry Group and you and your team for doing the work that you’re doing and providing the curriculum for free, which by the way, I should mention to listeners, you don’t have to be a student in high school to use the curriculum. It’s fully accessible online. All you need is a Digital Inquiry Group account, which is free to create. And my hope is that more people start to pay more and more attention to this. I think there’s a lot of discussion around the downsides of the internet and the downsides of social media and the downsides of AI that I wish some of that energy were translated into funding, resources, efforts, policy, regulation, the things that we’ve been able to do for other major issues in society.

So I applaud you and your team for doing the good work and I want to leave you with one last question that will hopefully be a little bit more optimistic since there’s been some existential discussion in this episode. What are you excited about? What’s keeping you lit up and what are you optimistic about despite all of the challenges that we’re seeing with all of this?

Joel Breakstone [00:42:10]: I would say that we believe that this is a problem we can tackle. It’s not an easy one, but we’ve seen over and over again that there are approaches that can be used to help people to become better informed online and that students and educators want to take these issues up. We’re privileged to have the opportunity to work with teachers all across the country and they are hungry for resources and for support. And their students want to learn meaningful strategies for engaging with the content that streams across their devices. And so I see it as a landscape of opportunity in that regard, that there are people who care deeply about this issue and are ready to take it up. We just need to, as a society, make sure that we’re equipping them with the tools to be successful in addressing this crucial issue for us as a society going forward.

Eric Ressler [00:43:15]: Wonderful. Any listeners who are also funders, please consider hitting up Joel and his team. They have spun out of Stanford and are now Digital Inquiry Group, their own 501(c)(3) nonprofit, and we need to fund these efforts. So anyone with big wallets and opportunities to make meaningful gifts, please consider that. Also, any listeners who can make even a small gift to Joel and his team, would also recommend doing that. Very much worth supporting this work. Joel, thank you so much for joining me today. This was great.

Joel Breakstone [00:43:45]: Thank you so much. It was my pleasure.

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There’s a quiet belief running through the social impact space that being too visible somehow cheapens the work. That good organizations should let their impact speak for itself. That humility is a virtue worth protecting, even at the cost of funding, talent, and reach. This episode makes the case that it’s a belief most orgs can no longer afford.

The provocative claim at the center of the conversation: organizations that are consistently good at visibility outperform those that are really good at impact. Not because impact doesn’t matter, but because without visibility, there’s no flywheel of attention, trust, and resources to sustain the work at scale. The most funded organizations aren’t necessarily the most effective ones. They’re the most visible, and that visibility was almost always deliberate.

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So what counts as visibility, and who actually needs to see you? For some orgs, it’s a national audience. For others, it’s 10 donors over dinner. The answer depends entirely on who you’re trying to reach, but there’s a simple test: ask your board, your funders, and the people on your periphery what you do and what impact you have. If the answers are vague or inconsistent, you’re looking at a visibility problem, a messaging problem, or both. And if you had to pick one to solve first, visibility wins, because at least it opens a door.

The practical path forward doesn’t require a massive budget or a media team. It can start with two articles a month, a single newsletter, or being deliberately visible to one person who represents the audience you care about most. One organization launched a video podcast four weeks ago and already has 15,000 views, guests receiving donations, and a three-month booking waitlist. The flywheel builds from the smallest possible action, but only if you take it.

Episode Highlights:

[00:00:00] Eric’s claim: visible orgs outperform high-impact orgs
[00:02:30] The humility trap and the “scrappy org” fallacy
[00:03:30] Why the most funded orgs are the most visible, not the most effective
[00:04:00] The Obamacare vs. Affordable Care Act branding lesson
[00:08:30] Visibility as the most underleveraged strategy in social impact
[00:10:00] The visibility test: can people describe what you do?
[00:14:00] If you had to pick one: visibility or messaging?
[00:17:00] Building visibility into every program from the start
[00:22:00] Starting from zero: one client’s two-articles-a-month breakthrough
[00:25:00] Jonathan’s journey from skeptic to podcast host
[00:27:00] 15,000 views in four weeks and guests receiving donations
[00:31:30] Using media to scale your face time with future donors

Notable Quotes:

[00:01:05]: “Orgs who are consistently good at visibility outperform and are more successful, generally speaking, than orgs who are really good at impact.” Eric Ressler

[00:02:25]: “There is just some sort of moral objection to maybe if we’re too visible that devalues the sincerity or the authenticity of the impact. There’s a sort of humility thing in there.” Jonathan Hicken

[00:02:50]: “I think that era is over. I would not bet on that strategy if I were you.” Eric Ressler

[00:14:00]: “Visibility, man. At least you get the chance. You’re opening a door and people could maybe dig in on their own. If you have no visibility, you don’t even have a chance.” Eric Ressler

[00:24:35]: “Literally be visible to one person. Pick one person that you think represents the kind of people that you want to be visible to and be visible to that one person.” Jonathan Hicken

[00:32:30]: “You’re almost certainly under-indexing on it. Take it seriously and reap the benefits.” Eric Ressler

Resources & Links:

• Seymour Marine Discovery Center — Jonathan Hicken’s organization at UC Santa Cruz

• Science Solutions Santa Cruz — Jonathan’s new video podcast.

• Gallup Poll: What’s in a Name? Affordable Care Act vs. Obamacare

• Obamacare/ACA polling data — Measures of public opinion of the Affordable Care Act (ACA)

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:00]: Sometimes the nature of your work is complex. It’s nuanced. It’s behind the scenes. The impact that you do might take years or even decades to really show up. We’ve talked about this before on the show. Not an excuse. You still have to figure out how to make your work visible.

Jonathan Hicken [00:00:15]: The biggest question in there is who are you visible to?

Eric Ressler [00:00:20]: Yes.

Jonathan Hicken [00:00:20]: That’s a question I’m asking myself right now at Seymour Center is who are we visible to and why? And what is the result that I need to see as downstream [00:00:30] of being visible today?

Eric Ressler [00:00:30]: I’m Eric Ressler.

Jonathan Hicken [00:00:30]: I’m Jonathan Hicken.

Eric Ressler [00:00:35]: And this is Designing Tomorrow. So Jonathan, lately I’ve been working with clients and this happens to me, I feel like in fits and starts a little bit, where sometimes the clients are a little bit reluctant to be visible about their work. There’s a couple different reasons why this shows up, which we’ll get into. But it irked me enough that I felt like I’m going to bring this into the pod for this week and I’m going to make maybe a little bit of a provocative claim here, which is that orgs who are consistently good at visibility outperform and are more successful, generally speaking, than orgs who are really good at impact.

Jonathan Hicken [00:01:15]: Spicy. I’ve been thinking about this a lot lately at Seymour Center.

Eric Ressler [00:01:20]: And just to be clear, I’m not saying you shouldn’t be good at impact. What I am saying and my claim here is that you also have to be equally good, if not better, at figuring out how do you make your work visible.

Jonathan Hicken [00:01:30]: Let’s break this down.

Eric Ressler [00:01:30]: So a couple things. There are good reasons why visibility is hard in our space, and I do want to acknowledge some of those reasons. So sometimes the nature of your work is complex, it’s nuanced, it’s behind the scenes. The impact that you do might take years or even decades to really show up. We’ve talked about this before on the show. Not an excuse. You still have to figure out how to make your work visible. Sometimes it’s capacity. We don’t have the staff. We don’t have the time. We’re so busy doing this. Not an excuse. You have to figure out how to make your work visible. So I hear all of these reasons, and they’re valid reasons, but I am going to passionately defend. I don’t care about those reasons. This is so important. You have to figure it out. You have to figure it out just the same way you have to figure out and get creative and get scrappy or whatever word you want to use to actually make an impact as an org too.

Jonathan Hicken [00:02:20]: I think you’ve missed one of the reasons why some of us in the space might avoid being visible. And that is just some sort of moral objection to maybe if we’re too visible that devalues the sincerity or the authenticity of the impact. There’s a sort of humility thing in there.

Eric Ressler [00:02:40]: That’s a big one. The we’re a scrappy org doing good work behind the scenes fallacy.

Jonathan Hicken [00:02:45]: Yeah. I don’t-

Eric Ressler [00:02:45]: No, not an excuse.

Jonathan Hicken [00:02:50]: It’s not good enough. I agree. Not good enough. I agree.

Eric Ressler [00:02:50]: I think that era is over. I think that there used to be, and maybe there’s still some corners of the social impact ecosystem where you can get away with that, but I would not bet on that strategy if I were you.

Jonathan Hicken [00:03:00]: Now, when you say that an organization that is better at being visible than one that’s not outperforms, what does that mean? What do you mean by that?

Eric Ressler [00:03:10]: That’s a good question because by what metric, right? Largely resources. And so resources matter in this space. One of the biggest barriers of impact work is not having the proper resources to match the scale and the ambition of your mission, especially when your mission is really ambitious or big. So what I’ve noticed is that a lot of orgs who get the attention, who get the funding, who attract the right teams and the staff to do their work, there are also the orgs that are the most visible. Begs the question, what came first the chicken or the egg? Are they visible because they are so good at their impact that they naturally become visible? And I don’t think so.

Jonathan Hicken [00:03:50]: No, no, I don’t think. I mean, maybe there are a few cases of that being accidental, but I think in the vast majority of visible organizations [00:04:00] were deliberate about it.

Eric Ressler [00:04:00]: Yeah. So let’s talk about, I have a sort of weird political parallel here that I think is interesting. So you know Obamacare/the Affordable Care Act, right?

Jonathan Hicken [00:04:10]: I certainly do.

Eric Ressler [00:04:10]: So even at a national politics level, when we’re talking about reaching everyday citizens for an issue that matters to basically everyone, healthcare, they did polling and they, I don’t know, we’ll look it up and put it in the show notes, but I distinctly remember this, where people pulled very positively overall for the Affordable Care Act. And those same people pulled very negatively for Obamacare.

Jonathan Hicken [00:04:40]: The branding of Obamacare.

Eric Ressler [00:04:40]: Yes. Just the name, just even Obama. And there’s political polarization and whatever in the mix there for sure. But my reflection here is that Democrats have traditionally been not very good at making their work as visible as they could or should. And that is one of the problems that they are facing as a political party and movement right now, just at large. There’s obviously a huge, there’s lots of disagreement and differences in the Democratic Party and Democratic leadership and whatnot, especially in this moment. On the contrary, Trump is very good at making his work visible even when, and maybe especially when it’s awful. And maybe that’s because it’s like bull in a China shop style visibility where it’s just like you can’t look away or a slow motion car wreck. But even when you think about what’s going on with a lot of his policies, it’s almost like spectacle as policy. I think I probably stole that from Ezra Klein. But the point being that we need to make our work visible at every scope and scale from the national level all the way down to community level. Because if the work isn’t visible, then you can’t build that flywheel of getting attention, educating people, creating behavior change, getting the resources that you need, reaching the right people who are either partners or funders to get that flywheel going and get the resources you need to actually have your mission scale and make the impact that you want to.

Jonathan Hicken [00:06:10]: In the political sphere, there’s this New York mayor, right? He’s a Democrat and he’s getting good at making his work in New York visible. And that I think that probably explains a lot of this attraction across the country for him. Mahmdani, I think is his name.

Eric Ressler [00:06:25]: That’s right.

Jonathan Hicken [00:06:25]: But I have to ask you, right? In that example, would you then say Trump is more effective than Obama because he’s more visible?

Eric Ressler [00:06:40]: Well, again, by what measure, right? Trump, for all of his faults, I’m obviously not a supporter of Trump. One thing he is really good at is getting media attention and media visibility. And so by that metric, I think he beats pretty much every politician ever. Is he more effective, was the question?

Jonathan Hicken [00:07:00]: You used the word outperform.

Eric Ressler [00:07:00]: Outperform. Right, right, right. Well, if you look even, and I don’t know how much we can really attribute success around fundraising to his visibility only, et cetera. But yeah, I mean, he’s been extremely successful with fundraising as well. So if you want to look at it from that metric. And if he were also competent, he would be able, he would have the resources and the setting and the scenario to actually take that visibility, take those resources and apply them in a strategic way. And you can argue that in certain cases he has whether you are for or against his policies. But yes, I do think he’s been very effective at harnessing attention and being able to turn that into at least directional policy action, even if he’s incompetent at actually creating change in a meaningful way, because he’s essentially sidestepping all the legislative processes that will make his change durable over time.

Jonathan Hicken [00:07:55]: That’s one of the world’s biggest stages. And the point carries over to one person, tiny little nonprofits too, right? Even if you’re at the smallest of scales, being visible is a critical component to you being able to deliver impact. That’s the argument I think I’m hearing you put forward.

Eric Ressler [00:08:15]: Yeah. Let’s bring this back to our listeners here and our audience to your point. And I do agree that yes, this matters if you are a two person nonprofit or a 50 person social enterprise. If you’re doing work in the social impact space, visibility is what I’ve noticed, probably the single most underleveraged strategy for creating social change. And I’m passionate about this. I have an agency built to solve this problem to some degree, but I think maybe what we should do next is talk about what do we mean exactly when we say visibility? Because I think that’s a word that can connote different types of things. And I think probably the first thing people are going to think about is media attention, being written up in media or having large social followings or getting lots of likes and comments on your social posts or having a big newsletter, that’s a form of visibility. And I actually think that’s quite important because so much information and so much relationship building does happen through digital channels these days. But another opposite form of visibility that could actually in certain cases, depending on the type of org that you are, be even more effective or successful would be a dinner with 10 people who matter and making sure that they understand who you are and what you do and the impact that you’ve had too. So there’s not a one size fits all. So there’s maybe a little bit of a test that you can do as an organization to say, “Hey, do we have a visibility problem here?” So here’s a test you might be able to run, ask a couple different cohorts, what do we do and what impact do we have in the world? And let’s say maybe you should ask your internal team this, you should ask your board of directors, you should ask aligned funders who you’ve worked with before. It’d be great to, if you could, pull people who have tangential understanding but aren’t deeply in your world yet. And if you notice that there’s not a cohesive, somewhat consistent, clarified answer to those questions, more often than not, you have two problems, a visibility problem and a messaging problem, they go hand in hand, which we can break down in a little bit more detail, but that’s a good way to test, do I have a visibility problem at my organization?

Jonathan Hicken [00:10:35]: The biggest question in there is who are you visible to?

Eric Ressler [00:10:35]: Yes.

Jonathan Hicken [00:10:40]: I think that’s a question I’m asking myself right now at Seymour Center is who are we visible to and why? And what is the result that I need to see as downstream of being visible to them? And so in your example, maybe there’s an organization out there that wants to be state or nationally visible for whatever reason. For us, Seymour Center, we care about being visible within Santa Cruz County, right? We’re a very local and regional organization, so I care about that, but another organization might not care about that at all and they may care about those 10 donors or the 10 most important policymakers or whatever, but the point is you got to make sure that those people you care about most can answer these two questions consistently.

Eric Ressler [00:11:25]: Exactly. So to your point, you don’t need to be visible to everybody depending on the type of org that you are. If you’re a grassroots advocacy org, yeah, the more visibility, the better, right? But if you are, for example, one of our clients works only with state legislators. And I remember in our listening session that we did with them recently, they were very explicit about we do not need to be a household name in America for everyday people because those aren’t the people that we’re trying to reach here. We are upstream of that. So that’s one example. Or to your example, you might care a lot about being visible in a particular region or a particular community. You probably don’t care what people in Kansas think about the Seymour Center as much as people right here in our community. Now, could national visibility be a net benefit to you?

Jonathan Hicken [00:12:15]: Sure,

Eric Ressler [00:12:20]: Sure. But if you’re going to have to prioritize, yeah, I do think it’s worth thinking about who are the most important for me to be visible to as an organization.

Jonathan Hicken [00:12:25]: I wonder though, you said if we’re talking to donors, we’re talking to funders, maybe we’re talking to several, we do your exercise, we do your test, right? And we talk to all these different groups and they’re giving us different answers. There’s nuance in interpreting those answers. And I don’t know if we want to do that right now, but you kind of expect these different groups to give you slightly different answers.

Eric Ressler [00:12:45]: I think that’s true. Are we expecting those different groups to recite your elevator pitch and your perfectly crafted mission and vision statements? No. But if they can’t answer, maybe here’s a good way to think about it with enough specificity where they’re like, “Well, I know Jonathan’s doing something in the Marine space, but I don’t know if it’s conservation or advocacy or I think you can go see a whale there or something.” That is a sign that you’re not doing a good job with either your visibility and/or your messaging. So maybe let’s actually, if you don’t mind, let’s break down that distinction because I think I’ve seen it both ways. So I’ve seen orgs that have really dialed messaging, maybe because they worked with us or maybe because they did it on their own, but no solid visibility strategy, that doesn’t work either because there’s just not enough of the right people who have the opportunity to even see that message to understand it. The flip side problem is that you get a lot of visibility, but your messaging is so vague and so jargony and so unclear that people are like, “Yeah, they’re over here doing something in this space, but I don’t really understand it.” I would say that that latter example is a little bit more common.

Jonathan Hicken [00:14:00]: If you had to pick one to do well and one to do poorly, which one-

Eric Ressler [00:14:00]: Visibility, man. Yeah. All right. Visibility, because at least you get the chance. You’re opening a door and people could maybe dig in on their own. If you have no visibility, you don’t even have a chance.

Jonathan Hicken [00:14:10]: Yeah, fair enough.

Eric Ressler [00:14:20]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency, purpose built for nonprofits and mission-driven organizations. [00:14:30] For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:15:05]: I think about this in terms of sequencing and how much effort I’m putting into certain arms of the business at any given time. And actually, I think back to my time at tech and I worked at this company that was doing usability testing and it was a platform where people could sign up and take usability tests and earn 10 bucks for 15 minutes of their time. And there was this balancing act where we needed to get enough customers to run the business, but we also needed to get enough testers on the panel to meet the demand. But if we had too many testers, then they’d drop off because they didn’t get enough work. And if we had too many customers. So there’s this balancing act where it’s, what are we building at any given time? And I actually think of this work similarly. If we take impact and visibility as these two things to balance, I think that organizations need to start with the impact, but they’re going to need to turn their attention towards visibility for a while. But then I’m anticipating, at least at Seymour Center, I’m in this visibility mode right now, but I’m anticipating, once that really gets cooking, I’m going to need to turn back to impact and ramp that up. And it’s going to be this ladder, climbing up the ladder of visibility impact little by little.

Eric Ressler [00:16:30]: I actually want to challenge that thinking a little bit because I think that’s actually a common way to think about it. And I think there is a new strategy to consider that we’ve advised some clients to take that has been really successful, which is to build visibility into every, however you break down your work, every program, every initiative, so that visibility is built into the planning from the beginning. Now, we’ve seen this sometimes with major grants have a communications budget attached to them or something, right? And naturally you’re going to have to prioritize, and you’re in a mode of visibility right now, which I do want to give you a chance to talk a little bit about that. But one way to get started on this visibility play or this visibility strategy is to start to think about every time you are spinning up a new program or assessing a program, there should be a visibility arm or element to every bit of what you do. So if you think about your programs at the Seymour Center, education, exhibits, now we have Seymour Studios, visibility should not be necessarily always an equal amount of your work in each of those things. Some things are naturally going to have more opportunities for visibility or be a very visibility first play. But I’m going to argue and claim that everything that you do should at least be considered through a visibility lens because I think sometimes what happens is that we talk about this with clients and they’re like, “Okay, but I just don’t know what to talk about. There’s nothing new going on or there’s nothing exciting.” And then you realize or re-realize through working with them that you might think that thing is boring, but that’s actually exactly the thing that you need to talk more about. Maybe sometimes that’s a build in public behind the scenes and we’re working with an org right now who’s in a little bit of a pilot experimentation mode. It’s like, “Well, we don’t have any impact yet.” Totally fair, right? We don’t want to make up impact. That’s not the idea here. So instead, let’s shift into a mode where it’s like, “Hey, here’s our thesis, here’s what we’re seeing, here’s what we’re observing in the space, and here’s what we’re learning along this journey so far. And we’re going to take you along for that ride and say, hey, this is what’s stopping us right now. Here are the challenges and here’s how we’re thinking about solving them.” I think some orgs do that in a really interesting way and that build in public, behind the scenes style of visibility and content and storytelling can be really magnetic to your supporters.

Jonathan Hicken [00:19:00]: I just went through this little journey as you were going through that. My first gut reaction was like, no, dude, it doesn’t work like that. You can’t build visibility into every program, especially if you’re a small organization, that’s just impossible. The dollars don’t add up. The dollars and cents don’t add up. And then I corrected myself and I was like, no, actually you can do small things.

Eric Ressler [00:19:25]: It doesn’t have to be huge.

Jonathan Hicken [00:19:25]: It doesn’t have to be huge. And so even we have volunteering, we have our youth school programs and stuff like that. And we actually, I’m realizing in real time, and maybe this is a little encouragement for listeners, yeah, we build that in because we know that in volunteering, folks that are retired and college students are the people who volunteer the most. So we make sure that when we’re recruiting, we hit those audiences. And our school programs, I actually think of teachers as being our constituent In that program. So we’re like, okay, how are we communicating with teachers? So yes, it is possible. It doesn’t have to be huge, but you do have to be deliberate about it.

Eric Ressler [00:20:00]: That’s a good word, deliberate or intentional. I think my challenge to listeners is throw those assumptions away and just thought experiment, how might we make this part of our work more visible and what’s our visibility strategy? And look, even if you walk away and say, “You know what, there’s not really much there. There’s not much juice to squeeze out of that program.” Great. At least you tried, at least you went through that exercise because I think what ends up happening is orgs will just default to the obvious solutions, but then you get stuck telling the same stories over and over and over again. And a lot about publishing consistently, having a point of view, being visible in your work is figuring out how to tell similar or the same story over and over and over and over again in new and interesting and creative ways. So I think that if you look in the corners that you haven’t looked at, there’s sometimes some storytelling gold there.

Jonathan Hicken [00:20:55]: And it’s so funny because sometimes I feel like that’s my whole job, is telling this story a thousand times the day with slight little tweaks depending on who I’m talking to, but I’m just repeating this vision and this impact and the story over and over and over again.

Eric Ressler [00:21:10]: Yeah. I mean, let’s not forget that you hear that story more than anyone in the world, right? And so sometimes you’re like, “Well, we already did that piece. We already did that thing.” I mean, I’ve been talking about brand for 16 years. You think I don’t get bored about it, but it’s like I constantly find new ways to think about it and to repackage and retell the story.

Jonathan Hicken [00:21:30]: I actually think you don’t get bored with it.

Eric Ressler [00:21:35]: Yeah. Okay. I don’t really get bored with it, but I do sometimes feel like, “Oh, we already did something on that.” And even some of these ideas in this podcast we’ve covered in various ways and past ones. Sure. So look for those opportunities. I do want to speak to something else you said, which is, we don’t have the dollars or cents for this. And you already alluded to this, but if you’re a listener right now and you’re like, “Okay, Eric, I’m convinced I need to be more visible. I’m going to take visibility more seriously in my work, but how do I even get started? It feels overwhelming. We don’t have the dollars. We don’t have the capacity, whatever the constraints might be.” I think you just need to start, right? You need to start and just do one thing and commit to that and then build on that because my claim here and what I’ve observed over and over and over again is once you start, you might not see success immediately, but you’ll be surprised, especially if you’re going from zero to step one, how much impact even just a little bit of visibility might have. We, for example, had a client that we did a rebrand for, they were a brand new org. We started so simple. We’re going to write two articles a month and we’re going to send two newsletters a month. And at first they didn’t hear much. And then they went to a conference and everyone at that conference came up to them and was like, “Hey, I saw that article about that thing you did.” It was so good. And they were like, “Oh my God, people are reading our thing.” I mean, even our podcast, sometimes I feel like we publish into the void. And that’s the nature of podcasting as you see downloads, see views, but you get some feedback. But I commonly will get people who are like, “Hey, I listened to that episode and I thought it was really great.” I was like, “Cool, maybe hit like next time.” So you have to remember that, and this is a little bit of a content point of view, but there’s so many people who are lurking and are not participating, but you are creating signal. And so I think that if you’re in this position of, well, how do we even begin? First of all, just consider visibility as core to your strategy and think about for every program, for every initiative, for every area of our work, how might we build some sort of visibility strategy into that work and then begin. And then if you do that consistently and you build out that capacity, that skill, that muscle, what will you start to see? Well, now people start to understand your impact. They start to understand your story, start to understand what you do more that leads to opportunities to funders, to partners, to staff who you really need that you couldn’t have attracted before. It is this flywheel effect. And now, oh, we actually have some capacity. We actually have some more resources than we did last year. Let’s not just put all that straight back into program work only. Let’s make sure now that we are investing in brand, investing in storytelling, investing in visibility at large, and then that’s how it becomes this flywheel effect.

Jonathan Hicken [00:24:25]: For anybody out there that’s still thinking, “Okay, Eric, that all sounds good. You keep telling me just start, but how?” I would say literally be visible to one person. Pick one person that you think represents the kind of people that you want to be visible to and be visible to that one person. And that’s just doing the reps. That’s just building the muscle. Pick that person and be visible and then it’ll grow, right? And then you’ll start reaching more people like that and stuff. So I would say literally one person.

Eric Ressler [00:25:05]: Yep. So I remember season two or something when we still had seasons on this show, I claimed, Jonathan, you need to be your marketer at the Seymour Center. And at the time you’re like, “No, dude, I’m not doing that.” I convinced you on that one. You’ve come around.

Jonathan Hicken [00:25:20]: I’m fully in, man. I have drank the Kool-Aid full blown.

Eric Ressler [00:25:25]: So now I want you, before we wrap up today, to just tell a little bit of a story. We’ve built this Seymour Studios out here at the Seymour Center where we’re recording today. You’ve launched your show, Science Solutions Santa Cruz. It’s like what, week three of it being out at the time we’re recording this, something like that?

Jonathan Hicken [00:25:40]: Yeah, four weeks,

Eric Ressler [00:25:40]: Four weeks in

Jonathan Hicken [00:25:40]: And almost 15,000 views.

Eric Ressler [00:25:45]: So tell me about how good my idea was here. No, I want you to make an honest case and reflection of how this visibility has affected your business so far. And obviously it’s still early, but I’m really impressed with how successful the show is so far.

Jonathan Hicken [00:26:00]: Yeah. I mean, look, I did the thing where it was just get started. And to be fair, we had the resources to go bigger.

Eric Ressler [00:26:10]: Sure.

Jonathan Hicken [00:26:10]: We had the time, we had the team, we had the resources and we had a clear idea of the story we wanted to tell and who we wanted to tell it to. All of that was pretty clear to us when you pitched this idea to me on our walk along Westclef. So just acknowledging that all of those pieces were already in place for us. We had the space, right? There was a lot of reasons why we were set up for it. I just took the plunge. I knew going into it that I didn’t know if this was going to be successful and it’s still early. There’s still a lot to learn. But four weeks in, we’ve got 15,000 views. I’m already booked out three months with guests. I have people in the community reaching out to me asking to come on the show. I’m getting people writing emails to my guests. In fact, we just got an email today from someone that’s in one of my guests’ universes saying how much they appreciated the perspective and advocacy and stuff. And so-

Eric Ressler [00:27:05]: Guests are getting donations?

Jonathan Hicken [00:27:10]: Yeah. And one of my guests called me saying that she had gotten a donation as a result of the podcast we did together. And so I mean, it was scary and it felt very risky. And to be honest, it still does, right? I mean, we’re seeing some really cool, honest, exciting early results, but every time I sit down on this chair to interview someone for the show, it feels like a risk. And I think a big part of it was just taking that plunge and taking that first step. And so-

Eric Ressler [00:27:40]: So it’s a risk in that there was upfront investment. And by the way, listeners, do you need to build out a pro level podcast, video podcast studio to build visibility? Again, no. No. It’s a good strategy if all the conditions are right, I think creating media like this, I think is an important strategy in our current media environment, but there’s that upfront risk, right? But there’s also the bigger ongoing either risk or trade off of a lot of your time and energy now is spent on this kind of work, which means you are not doing other things that you did before, right? You have a certain amount of time as an executive director. So I’m wondering if you could talk about how you think about that trade off. And you even mentioned earlier, okay, we’ve been really focused on visibility. Now I’m worried about impact, but I want to challenge, I don’t think those two things are a zero sum game. I think they feed on one another.

Jonathan Hicken [00:28:35]: Yeah. I mean, my vision for the program that we’re producing is actually that I’m building it so I don’t have to be the host. That’s my vision here is that ultimately somebody else is in this seat. And frankly, I envision launching multiple shows and having this network of media, frankly, where I then get to step back and point my attention as executive director to other areas that need my attention, but it was, and I believe it continues to be the right use of my time. Now what’s really important, the thing that I’m trying to turn on is the fundraising results. For me, the visibility has to lead to fundraising results. And we’re so early in on this program that I haven’t seen those yet, at least that I’m aware of. And so that’s my next focus is turning on that connection. And I’m confident that it’s going to work because the results are so impressive that I think the donors in my network are going to see real impact and real meaning in that, just like I do.

Eric Ressler [00:29:41]: I think one way to think about this, and I think about this in our business also is, your next cohort of donors have maybe not even heard about you yet. And I think about this in the nature of our work being transformative. We work with clients over multiple years, but every year we work with the new cohort of clients too. And so the clients that we work with three years from now might be listening to this episode today and I don’t know that this episode is going to be that first touch point. So this is just brand building 101. So I think not to say you might not get a viewer of a show like this that then is already in a place that they’re already really keen to donate or to make an investment in an org like yours and that visibility instantly leads to a donation, that’ll happen too. But more commonly, you need a certain number of just visibility touchpoints to build trust, to build credibility, to build a relationship over time. So a good way to think about visibility as a strategy is you are paving the way for, in your case, next month’s donations, next year’s donations, five years from now donations. And if you build that visibility machine, you’re just creating more opportunities for those conditions to build that. And it’s the same for me as well. And so it is a bit of a long game, right? Visibility. It doesn’t have to be. There’s short game visibility plays you could do as well, but you do have to be patient at some level and you have to be willing to play that long game for it to work out.

Jonathan Hicken [00:31:15]: One of the things that we knew about fundraising is that we, in terms of major donor fundraising, we got the best results when I personally had time with the individual or the family or whatever, and that was producing results. The challenge is it’s hard to scale one person’s face time with a lot of major donors.

Eric Ressler [00:31:35]: Yes.

Jonathan Hicken [00:31:35]: And so the way I think about the show is actually scaling myself with donors that I don’t even know about yet, giving them a chance to get to know me, get to know the questions I’m asking, the kinds of people that I’m working with week in and week out, and having this fantastic starting point. So when I do meet that donor, they know me a little bit.

Eric Ressler [00:32:00]: Yes, yes. I think I say this a lot when we work with clients and we work with their development directors or development teams. It’s like, we do our job well and your job gets significantly easier because we are building awareness, trust, credibility so that by the time you sit down for an in-person meeting, you’re not starting at zero anymore. You are three or four meetings ahead that you would otherwise have to do in person. So yeah, I think to me for listeners, the big takeaway [00:32:30] today is visibility matters. You’re almost certainly under-indexing on it. Take it seriously and reap the benefits.

Jonathan Hicken [00:32:40]: Start with one person if you have to, but get started.

Eric Ressler [00:32:40]: Okay, Jonathan, this one was fun.

Jonathan Hicken [00:32:40]: Thanks, Eric.

Eric Ressler [00:32:45]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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The social impact sector has made community co-creation almost sacred. Design with people, not for them. Give everyone a voice. And I believe it, but I’ve also watched it go sideways. The meeting that devolves into NIMBYism or the planning process that stalls because everybody gets a vote, but nobody makes a call. The loudest voices in the room are often not even the most informed ones, and sometimes a leader just has to make a decision. I’ve lived this running my own agency for 16 years. I still don’t have a clean answer for where the line is between participation and just making progress. Taylor Stuckert has been on every side of this tension. He’s the CEO of Lead for America, a national service organization. And before that, he spent 14 years as a planner in his hometown of Wilmington, Ohio, a place that lost almost 10,000 jobs overnight when DHL shut down.

He watched that crisis get managed behind closed doors. He also sat through years of heated planning commission meetings where community input made things harder, not easier. And in our conversation, we dig into this question that nobody in our space really wants to ask out loud. Can too much community input actually be a problem? And what does it look like to lead with conviction while still making room for the voices of the people that you serve?

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Episode Highlights:

[00:01:30] Wilmington, Ohio and the day DHL disappeared
[00:05:30] Why big economic decisions used to happen behind closed doors
[00:06:30] The guerrilla flyer campaign that drew hundreds to a town hall
[00:08:30] When community input becomes a double-edged sword
[00:11:30] The civic infrastructure most communities never build
[00:12:30] Building a steering committee out of strangers
[00:14:00] Stop trying to please everyone
[00:16:30] The binary framing trap killing community engagement
[00:17:30] There is no “the community”
[00:19:30] What gets lost when you climb the leadership ladder
[00:23:30] Inheriting a CEO role you didn’t found
[00:28:00] Why the brain drain narrative misses the bigger story
[00:31:30] National service shouldn’t only be for 22-year-olds
[00:37:00] Why AI will widen the divide we never closed
[00:44:30] What keeps a leader going when the work gets heavy

Notable Quotes:

[00:14:10]: “We have to get away from this notion that we’re going to make perfect decisions. Everyone always says it, but we still struggle with the idea that you’re just not going to please everyone — and that shouldn’t take away from how we engage everyone.” Taylor Stuckert

[00:17:40]: “We act as if the community is this unified object that has complete consensus and you’re either engaging them or you’re not. And that’s just so inaccurate to reality.” Taylor Stuckert

[00:11:45]: “You have to invest as much time, energy, and resources in the actual preparatory civic engagement work as you do around the issue itself. Proactiveness is everything — and yet planning so often feels reactive.” Taylor Stuckert

[00:21:10]: “I’m always so impressed by leaders who find a way to sit in that discomfort and yet still have conviction and move quickly — not in a reckless way, but in a confident way.” Eric Ressler

[00:40:35]: “If we really want to get the most out of the economic opportunity from AI, we have to have a country where everybody has the basic digital skills and the basic access to deploy them. We would be selling the opportunity short for anything less.” Taylor Stuckert

[00:47:40]: “The future is unwritten, and we are the authors of that story.” Taylor Stuckert

Resources & Links:

• Lead for America — The national service organization Taylor leads, focused on activating local talent in communities across the country

• American Connection Corps — Lead for America’s fellowship program placing emerging leaders in digitally disconnected communities

• Carnegie Corporation of New York — Referenced via Taylor’s mention of former president Dame Louise Richardson and her work on binary framing

• Energize Clinton County — Taylor’s previous nonprofit in Wilmington, Ohio.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:30]: Taylor Stuckert, welcome to the show. Thanks so much for joining me today.

Taylor Stuckert [00:01:30]: Yeah, thanks for having me.

Eric Ressler [00:01:35]: So you have a really interesting background — Peace Corps, coming back to rural Ohio where you grew up and seeing a really changed community. And I actually think I want to start there, because you came back to a community that had gone through a pretty big shift. The main employer, DHL I believe, had gone through some big restructuring and there was a lot of disruption in the economy. And my understanding from talking to you and learning about you is that there was this moment where big decisions that really had a major influence on the future of the city were being made essentially behind closed doors — by senators, by corporate leaders. And you said, “No, that’s not how we’re going to do this.” And you took matters into your own hands with a bit of a guerrilla movement-building play. I’d love if you would share that part of your history with our listeners as a way to kick off our interview today.

Taylor Stuckert [00:02:30]: Yeah, absolutely. So the company was DHL, an international shipping company most people probably know about. And Wilmington’s unique. It’s a small town of about 12,000. If you look at it on a satellite view on Google Maps, you’ll see this large airport that physically is about the size of the community. It was an old strategic air command base from the 50s. It closed down in the 70s and then was acquired by a shipping company in the early 80s. Airborne Express grew that incrementally over many years. And then DHL, the largest shipping company in the world, acquired it as the headquarters for its domestic operations in Wilmington, Ohio. Growing up in the community, the airport was always a backdrop. It wasn’t anything that stood out the way that a lot of physical, large employers and industrial campuses stand out, because it’s an airport.

You’d see a stream of planes flying in on the night sky every night growing up. So it was always just there in the background. You knew people that worked there. I had family that worked there. Maybe because of its slow growth over many years, it wasn’t anything that felt like this big splash and then something that just disappeared. It was slowly growing over many years and then it disappeared. So it was a unique situation in that regard. I had been in the Peace Corps and service was disrupted, and I ended up back home really by accident around that time. The national recession was starting. Because of the timing of the announcement, Wilmington was thrusted into the national spotlight — some people would say it was the ground zero of the Great Recession at that time.

I’ve talked to a lot of colleagues about this, especially in recent years. When we think of impactful issues facing communities, it’s very natural today for us to think about community meetings, town halls — these are very relatable environments today. People can picture the viral videos of town halls. And I think we take for granted how new of a concept that is. In New England, they’ve always had town halls and robust civic engagement, but for most of our communities, large economic decisions, industrial decisions were not things that involved a very democratic process with the broader community. However, when I was in the Peace Corps, that was something we were teaching in our work abroad — the importance of community engagement, of people having a seat at the table and drawing out the vision for the future of the community.

So when I came back home, this big event was happening, and for that conversation to not be happening felt a little odd. I don’t think it was unusual at the high-level view — that was actually probably the norm — but it was unusual looking at it through the lens of work we had done through international development. A friend of mine from growing up in Wilmington and I happened to be home at the same time, and we felt that because this was such a profound change for the community, it would make sense for the community to have some voice in that envisioning process for the future. We didn’t really have a strong vision for what that should be. It was really about galvanizing a community conversation. So we took what you might call guerrilla tactics — identifying certain popular community gathering spaces or moments to start to initiate that conversation.

We have this holiday parade that takes place every year, the Saturday after Thanksgiving. Thousands of people are in our downtown, and we printed out probably a thousand or more of these little flyers that just said, “Are you mad about the DHL situation? Come to this meeting to talk about the future.” We handed them all out, and we didn’t really have too much of a plan for what that conversation would look like. We certainly didn’t anticipate what ultimately transpired, which was a few hundred people showing up to a meeting. We had several regional news stations that even came. We had to throw this conversation together. For us at the time, it really was about: Wilmington’s going through this major economic transition. Where do we see ourselves from an employment standpoint, from a workforce development standpoint, from a community standpoint, where do we see ourselves in this future economy?

It’s interesting to look back to 2009. Hindsight’s always 20/20, but to think about how in that moment even then, there was a lot of question about what the future of work looked like. What would transpire coming out of the recession? And it feels eerily similar to where we are today as we think about technological disruption, how jobs are going to be impacted by these disruptions, and what are the future skills needed? What are the future job opportunities? What do wages look like? These were a lot of the same questions that we were having and talking about in 2009 as well.

Eric Ressler [00:08:25]: There’s a lot of good threads I want to pull on there. We’re going to get to your current role as CEO of Lead for America and talk a little bit more about what you’re going through right now that I think will relate back to this. But I actually want to hold on something I struggle with a lot personally trying to form a strong opinion about — community input, community co-creation. There’s this lionization of that approach in the social impact space, and it’s rooted in good reasoning. But I also think there are some negative downsides that can happen when the process gets almost too democratic, to put it in a weird way. The way I think about this showing up is in city council meetings, community convening meetings where there are residents who have a stake in the game, who have really strongly held opinions, but maybe don’t see the full picture or have very personal motivations for their opinions.

And then I see process for social change get bogged down. I’m curious about what is the best version of that and what is the worst version of that? One practical example we can talk about is housing supply. In California where I am, there’s a very strong state mandate where our cities and counties actually have much less power than they used to around decisions around housing. And yet housing creation is still a major issue, and there are very strong counterpoints to some of this housing supply creation. Some of the criticisms I think are fair, but other times it’s really just straight NIMBYism. So community co-creation, community input is a double-edged sword in certain ways. You I think are uniquely qualified to have a strong opinion about this because of your background and your work you do every day. How do you think about that tension?

Taylor Stuckert [00:10:25]: Yeah. I’ve lived it from every angle of perspective around it, from NIMBYism to now YIMBYism. And I heard a recent one, a new acronym recently called Banana, which was “build absolutely nothing anywhere near anything,” something like that.

Eric Ressler [00:10:50]: Never heard that one.

Taylor Stuckert [00:10:50]: Yeah. Which is often what it feels like. I was a regional planning director before this. I was on the front lines of that. I’ve been through numerous heated city council meetings, heated planning commission meetings about everything from very impactful things based on scale to things that it’s really surprising we’re having a heated debate about — from the smallest of items like a fence to a full housing development. So I definitely hear you on the upside and downside of that. I felt like I had really developed my thinking on it throughout my time in planning, and really centered it on the belief that you have to invest as much time, energy, and resources in the actual preparatory engagement, community engagement aspect to the work as you do around the issue itself. Proactiveness is everything.

And yet planning so often feels so reactive. Community development work often feels so reactive. All the tensions we’re talking about are reactions to an announcement, to a perspective development. We’re not doing that civic infrastructure work that’s needed to be in place before those big announcements happen. That’s the problem — we’re always a step behind. I remember we did a big comprehensive plan. It was one of the last major projects I did in the community. It keeps getting referenced by both sides in tense arguments these days. One thing I really set out to do for that process was to build a steering committee that involved mostly people I’d never met before. Clinton County, Ohio is a small county of 42,000 people. It’s amazing when you have tens of thousands of people, how easily it can be to think that you know everyone when really you probably know less than 5% of the population.

So I was very intentional about that steering committee and identifying people who did not hold elected office, who were not the typical well-known people that you see in community meetings or at the front of city council conversations, and bringing them to the table. Several of them were people who had just moved to the community. Often that’s a tension point — “I’ve been here my whole life” or “you just moved here, what do you know?” It was a fascinating process. I wouldn’t say it was perfect, but it was really interesting how that shifted the dynamic of that process, of the conversation, and ultimately of the adoption of the plan. It actually felt like something that people saw themselves in, that they heard their voice in.

To your point about the upside and the downside, we have to get away from this notion that we’re going to make perfect decisions. Everyone always says it: “you’re not going to please everyone.” That’s such a cliche, but yet we still struggle with that notion. You’re just not going to please everyone, but that shouldn’t take away from how we engage everyone, or at least create opportunities for everyone to be involved in the process.

Eric Ressler [00:14:35]: Yeah. I appreciate your commentary on that. I actually think there’s a similar issue I struggle with even leading a small social impact agency — and I can imagine this problem only scales as you grow and you’re leading a much bigger team than I am. Similarly, you want to co-create with your team. You want to empower your team, you want your team to have ideas and bring them in good spirit and have decision-making, not just be totally hierarchical and top-down. And yet similarly, there’s a time and a place for leadership — for people who are in positions of leadership to make strong choices, even if some people disagree with those choices. I see this as a similar metaphor to co-creating with the community. There’s a similar scope and scale where you’re co-creating within an organization that I think a lot of executive directors and CEOs are grappling with.

To me, it feels like a different flavor of the same tension and the same balance that needs to be reached. Honestly, that’s something I continue to struggle with as a leader. I’ve been running Cosmic for 16 years at this point. I’ve tried more democratic, less democratic processes — flatter structures, more opinionated leadership. And I still don’t think I’ve found the golden solution to that. It’s something that feels always a little bit fluid, maybe depending on the season we’re in as an organization. Are we in a growth mode? Are we in a consolidation mode? Where are we in the process? I’d be curious — does that parallel resonate with you from a leadership standpoint? How do you think about that as you’re running your organization as a CEO?

Taylor Stuckert [00:16:20]: Well, one thing I want to touch on too — the head of the Carnegie Corporation of New York, Dame Louise Richardson, brilliant person. A lot of her background was focused around domestic terrorism in Ireland. She’s from Ireland, and she talks a lot about the influence and the impact of binary framing in society as it relates to acts of aggression and violence. Going back to the community voice piece of it and thinking about it even from an organizational standpoint, through a variety of ways and factors, we have put ourselves in this position where everything is a binary choice. When we think of even — does the community have a voice, have they participated? It’s not a binary situation. It’s not yes or no.

One of the things I think about a lot lately, as you were talking about that being lionized in the social impact sector, is that that often surfaces. And yet we never really question what does it even mean — was the community involved or did they have a voice? Did we engage? Who is the community? And we act as if the community is this unified object that has complete consensus, and you’re either engaging them or you’re not. And that’s just so inaccurate to reality. Leadership is really that responsibility of hearing and listening and analyzing the landscape and hearing the multitude of voices of the community, recognizing that there’s a pluralism in community and bearing the responsibility of making challenging decisions based on the data and the observations and the information that they’re seeing in these situations. That’s why sometimes I don’t even like the notion of “we’re not going to please everyone,” as if pleasing is the basis of all decision-making or tough decision-making. We put ourselves in these binary corners of “you either pleased or you’re displeased,” and that’s just not often how it shakes out.

So when I talk to people who are coming up in their career all the time, I will say that I was thrust into a leadership role. I found myself leading a regional planning agency without a ton of serious management experience. And then I’ve continued to stay in a management or executive type position since that time. One of the things I realized when I stepped into that role was how much I gave up in terms of the hands-on work I was doing. I no longer was able to do the map-making or the design work that I really enjoyed doing. Now I was doing budgeting and management decisions and HR-type stuff — things I never imagined were a part of the equation. But we are trained to see all careers as a ladder that leads to an executive role.

I’ve accepted that I’ve been in that role now long enough that I’ve acquired a lot of the skillsets and the necessary lived experience to navigate it well, but I’m not sure if I would’ve followed that path again if I was given the choice. Because what comes with it is that responsibility of imperfect decision-making and dealing with a pluralism of voices and data and information, and never feeling like you’re really making a perfect decision. For us, naturally, that can be a challenge — you want to feel this sense of closure in decision-making. Sometimes it can happen in certain moments when you have a certain level of consensus or a process that feels fulfilling or satisfying of all the voices involved, but it’s maybe rarer than we think it is.

Eric Ressler [00:20:45]: Yeah. I imagine that almost everyone listening to the show who’s in any form of a leadership or management position can relate to that. I think that is a healthy challenge. I completely relate to “I never feel like I make a perfect decision.” Even that framing is probably a little bit of a misnomer. As I’ve been doing this work longer and learning from other leaders, I’m always so impressed and inspired by leaders who find a way to sit in that discomfort and yet still have conviction and move quickly — not in a reckless way, but in a confident way — and accept that they’re always going to be a student in life at some level. That’s a lot easier to say than to actually do, especially when real people’s lives and livelihoods are at stake, either just your employees or because of the type of work that we’re doing where the stakes are high at certain points.

We’re not talking about, in this space, “are we going to cut 15% of our highly paid tech workers?” — not to diminish the livelihood impacts of that for the tech worker class — but we’re talking about: “is this intervention going to hit underserved communities harder than we anticipate, or actually backfire in a way that is exactly opposite to the stated mission of our organization?” The stakes are much higher, and often the resources to have the right evidence, the right tools at our disposal to make those decisions as best as we can, might also not be ideal. It’s a really challenging situation.

Hey friends, real quick before we continue today’s episode — I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

I feel like I’d like to transition, and this is a good time, into your experience coming in as the CEO of Lead for America — not being a founder for the organization, but inheriting a CEO role, which is another identity shift. We’re going to talk a little bit about identity and narrative today. I’d love if you could just share a little bit of background on how that happened, what that experience has been like, and how you have stepped into that role as a leader inheriting an organization.

Taylor Stuckert [00:23:50]: Yeah. So I have been a founder of a nonprofit, and I feel like I can relate to the identity attachment that comes with founding something. I try to hold that carefully. I know firsthand what that attachment can feel like. I try to be very respectful and caring of the attachment that the individuals that started this organization, that got it off the ground, hold for it. I carry that with me as I do my work. I make sure I’m thinking about that and being considerate of being a steward of this mission — just stewarding it while I have it — that ultimately someone else will likely take it and leave their fingerprints on it as well. Having had that experience, I probably care for it a little more carefully than somebody that maybe hadn’t founded something before.

My style, in just about anything — whether it’s work or personal life — and something I’ve kind of dialed in on over the years, is really a listen-first approach to just about everything I do. I do try to ensure that I’m giving the appropriate amount of attention and thought and consideration to those that help construct things, those that feel part of things. That can be anything from the founders of the organization to the staff past or present. For us in particular, as a service organization, we have a lot of individuals who have passed through in a fellowship role and are now alumni. Hearing their experience and understanding what this mission means to them and holding that, while also inviting them to be a part of the continued evolution of the mission. I took that very seriously, and it felt right for me — just because of that experience and that approach — to come into a role like this where I’m not the founder of the organization. I don’t have that specific niche story that was often told over and over again as the impetus or the foundation for the existence of this mission.

But I’ve also been able to care for that and continue to grow and evolve that mission. This goes back to the conversation about who is the community when we talk about engaging the community. Is it a fixed group of people or is it a dynamic group of people that changes over time? My belief is that it’s always dynamic, and that the people coming into the work at this moment do have agency and do have say over what this mission means and how they’re going to contribute to it. So it’s a balancing of holding onto the past in a respectful and caring and considerate way — not losing sight of what people put in terms of sweat equity and care into this mission — but being a good steward and doing that, while also looking at current conditions and future horizons for where this work is going, and trying to steward the work in a direction that is sustainable, that is authentic, and is responsive to the world we live in today.

Eric Ressler [00:27:40]: When we were prepping for this interview — and a little bit of time has passed since we did that — you mentioned that you were in the process of going through a strategic narrative shift at Lead for America. Catch me up on where you’re at there and what was the impetus for that. How do you think about that in terms of identity, community, all of the topics we’re discussing here, and engaging your team in doing that?

Taylor Stuckert [00:28:05]: So again, I’m very comfortable looking at the past and recognizing it as a moment in time. Sometimes people get uncomfortable with the sense that when we talk about the past and we make shifts or recalibrate, that we’re saying that what they did was wrong. That’s never how I see it. I see it as just a moment in time. When this organization was founded, it’s an era I can totally relate to, because I was a part of that community. I was not involved in Lead for America, but it was an era in which a lot of books and research and articles were put out about the brain drain issue and about the loss of young people from the heartland. That really was the origin impetus for this work — you had a group of college-age students who had been from smaller communities all across the country, from Kansas to Oklahoma to Minnesota, Kentucky.

They were in college and they were looking at the landscape of fellowship opportunities, and they all were taking them to New York or DC or Silicon Valley. There really weren’t any opportunities to do a fellowship in the heartland or in a small community. They wanted to change that. They wanted to create opportunities for that. It’s very noble. It’s very relatable to me as somebody who moved to New York City and then came back to Ohio. But over time, as I spent a lot of time in Ohio and the Midwest, I really came to see that narrative as just one piece of the story, and a small piece. It’s definitely not telling the whole story about these communities and the future of these places. Returners are important. Brain drain is something communities should care about, just from the standpoint of: are we inviting the young people that we raise to stay here, but are we also giving them the opportunities to flourish and do the things they want to do?

But that narrative leaves out, I would say, obviously the majority of the population. Returners and brain drain make up a small percentage of the human capital that makes the community thrive. I noticed that in my own work before Lead for America — that we’re talking about a very small subset of individuals. As I came into this organization, I was very interested in expanding the tent, not just for that conversation, but for national service as a field. National service is something that does skew young, 18 to 24. I totally support a lot of the folks that are still adamant that this is the springboard for young people, and I agree with that. But I also think people spring at different times of life. Some people spring mid-career, they might spring into retirement. Service should be an opportunity that truly is open for all.

For a lot of our communities, we need everyone we can get and we should welcome anyone that wants to step forward. As I transitioned into this role, I was really interested in taking a step back and thinking about where is our mission and narrative really centered. Historically, the centering was on the individual service fellow that came through the program — their journey, what I was describing in the founders, that they got to do this fellowship and where did it take them from there. I really thought that is just a piece of the story and not the beginning and the end. The centering should be on the places we’re serving in this work. What is happening to the communities we’re supporting and partnering with in this journey? That really was the main shift — to focus our work on activating local talent and building the leadership pipelines that communities need to realize their own unique visions.

We’re not going to tell a community what their vision should be. We’re not going to describe or prescribe to them what talent looks like, that it’s an 18- to 24-year-old that went to this very prestigious school. It could look very different in one community. We’re going to let communities really be step in step on building what leadership pipelines look like to them. That was the main shift, and that’s where we have recentered our work, recalibrated our work. As we look ahead, we’re taking a step back. I talk a lot about — one of the things I was pleased by when I came into the national nonprofit world was that one of the universal consensus that I felt like I could see was everybody would always nod their head when somebody would say something to the effect of, “you’ve seen one community, you’ve seen one community.” We all sort of agree that communities are these very distinct, individualized things that at a certain level have similarities across the board, but we don’t arrange social sector interventions and even philanthropy in many ways at a national level to be aligned to that.

It works at the local level, it works at the regional level, but at a national level we really have a hard time doing that — about how we measure impact, how we tell that story, how we fund it. It is hard. It’s more challenging. But that’s really where I personally, and I think as an organization, we want to be — in that challenging space, because that’s where the work happens. That’s where innovation happens.

Eric Ressler [00:34:00]: Yeah. Tell me more about how you think about that with regards to — you guys are in local communities in the day-to-day work, and yet you are this national organization. Is it chapter-based? Is it cohort-based? Is it place-based? How do you get the best of both worlds? We do work with orgs like this that have districts or chapters, but then there is this kind of parent umbrella organization that provides the infrastructure, the backbone, the cross-learnings. What’s your version of that at Lead for America?

Taylor Stuckert [00:34:35]: Yeah. I came to look at it through my own lens as a local practitioner first, and for many years, about what was I missing in that regard? I was the person on the ground. I knew the community well. I didn’t need a national nonprofit to come in and say, “I should do this, this, or that.” What I was missing — and I think what LFA is focused on providing — was that I didn’t have the bandwidth to provide the administrative infrastructure that was needed to provide a fellowship opportunity to one or two individuals. That’s a lot to ask for. I wasn’t going to apply for a federal grant so that I could have one or two fellows working in my regional planning agency. The other thing was — I was very fortunate, so it wasn’t specifically for me, but I saw the benefit of it — to have been a part of a national dialogue. Because of the spotlighting around the DHL situation, I was very privileged to be a part of national panels about the future of small towns and rural communities.

I took a lot from that. I loved being a part of those conversations and bringing that knowledge back to my community, bringing those connections back to my community and those resources back to my community. That’s something that I feel any local practitioner should want — to feel connected to the country at large, and not feel that they’re working by themselves at the local level with nobody to relate to. Providing that national cohort model gives our participants who do our fellowship, but also the host site communities that we work with, the opportunity to be a part of something beyond their community. There’s these indirect, maybe even direct effects of that — especially as somebody who has worked in a rural part of the country, having exposure to other communities, to other practitioners, whether they’re in other rural communities or non-rural communities, is such an eye-opener and is such an important piece of knowledge to share with the community you’re working in. From a civic bridging opportunity, I think it’s a great way to bring people together from across the country doing similar work for places that they care about specifically.

Eric Ressler [00:37:00]: We’re in another moment right now that at least feels like we’re on the precipice of another major technological disruption that’s going to have impacts to the workforce, to careers, to starting and raising families. I’m speaking broadly about AI here, but I think other technologies as well. I’m not going to ask you to predict a future about what happens there — I don’t think anyone knows exactly what’s going to happen here. But what I would like to ask you is: what is the sentiment within these communities, especially within young people, where one of the stories that we’re hearing — and maybe even starting to see come true — is that quote-unquote entry-level positions are going to be some of the first to be most exposed to some of these new technological disruptions. You’ve led organizations and towns and communities through major change from an economic standpoint before. How do you think about those major disruptions and how to plan for them and how we can best support culture change at that scale?

Taylor Stuckert [00:38:10]: Yeah. What pains me the most about it is that I’m not that old, but I feel like I keep living through these crazy moments where I keep thinking to myself, when are we going to learn? Coming out of the recession, all the stuff I was saying about the proactive civic infrastructure building that we need to do — I think would have really served us well in this moment. Unfortunately, we’re just not there. I wish that we were. The thing I’ve learned over the years is to know that we don’t know, and to avoid some of these binary framings that we go into — that either AI is all good or it’s all bad. I really don’t operate there. There’s a ton of positive opportunity. There’s a lot of things communities should be thinking about and how they’re going to address it in their own unique way.

For me, there’s still a lot of things that aren’t settled on this conversation. I felt that early on, last summer, last fall, as data centers were being built. Where the developments are happening just so happen to be a lot of the places where the digital divide is at its greatest. You’re talking about places where big shifts are happening, big infrastructure being developed in communities where a lot of people still don’t have access to a laptop. They still don’t know what a keyboard and a mouse is. They have never done a telehealth appointment, and now they’re hearing about this new disruptive thing that the rest of us are ready to move on to. A few things come to mind for me. One is, this transformation is not going to happen in a healthy way if we don’t have this human infrastructure to support communities in making that transition.

If we want older adults to be using telehealth, they have to have a broadband connection, they have to have a device that they can use, and they have to have the digital skills to know how to use it. If we really want to get the most out of the economic opportunity potential from AI, we have to have a country where everybody has the basic digital skills and the basic access opportunities to deploy those skills to get the most out of it. We would be selling the opportunity short for anything less than that. I worry that if we try to moonshot past all of those things, we’re leaving the door open for political disruption that’s not going to serve anyone in the end as far as national progress goes, if we just leave it to that. It would be a misfortune if we just closed our eyes, covered our ears, and just hoped that everybody got it and was okay with it.

Eric Ressler [00:41:35]: Yeah. I think that’s fair. I’m under-impressed so far with how little AI is being considered for social innovation and social impact work. It’s happening at the individual practitioner level. The nonprofit space gets a lot of criticism for being slow to adopt technology, but I’m actually seeing — and there’s some data to support — that nonprofits are actually adopting AI more quickly than the private sector at large, which has its pros and cons. But to your point, yeah, we’re talking about this new transformative technology when a certain percentage of our population right here in America still doesn’t even have access to the internet in a meaningful way or the skills to use it effectively. I grew up as the internet was growing up. I had access to the internet very early. I was lucky in certain ways for that. In other ways, maybe not so lucky.

I worry that the internet has actually been in certain ways a net negative on society — especially when you see the polarization and how much hate and disagreement there is in our country right now. I don’t think the internet is solely responsible for that, but I think it is a big part of that equation. My fear is, will we see something similar happen with AI where it just creates an even bigger digital divide, even bigger divides in terms of class and wealth in America, where the most privileged and the wealthy of us are able to have even more leverage because of AI, and the people who are most at need or need more help or lack those resources — there’s this technology that in theory could help them move up in life, but instead is going to just hold them down.

I don’t know. There’s just so much going on with it. I don’t think anyone knows. But your story is poignant around these data centers that are using resources, water, electricity, et cetera, being built in these communities where a good portion of people don’t even have access to last generation’s technological innovation. Big issue, big equity issue. Not here to be an AI hater whatsoever. I think it has a lot of transformative potential. We use it all the time in constructive ways, even in our work today. But I do think this is a place where social innovation should be getting more attention than it is. I hope that leaders in our space can start to make a case for that and participate in it, and that the AI providers do a better job of ensuring we’re not just looking at how we can code things faster, but also how we can apply this technology to some of the things that we were promised early on in this vision they painted around medicine and health, and even universal basic income — was this thing that was talked about really early and doesn’t seem to be talked about nearly as much as part of the AI disruption story.

Taylor Stuckert [00:44:30]: Yeah. It’s hard. I’m in a lot of conversations where each one of those points gets brought up, and I still struggle with just the reality I see on the ground, which is — I’m plugged into this national community that’s talking about this very futurist vision of AI, but people around me are really just focused on this square box that’s being built in the middle of a cornfield. Those are just such divergent situations and realities. As a country, we’re in a position to really hopefully try to merge those two divergent realities, to bring people along with this opportunity and ensure that — we only get the most out of it when we have people participating and have the capability and agency to participate. I remain hopeful that that’s the direction we ultimately go as a national community, that we are able to merge those divergences and ensure that this is something that is about widespread impact.

Scale is the main distinguisher for AI — how fast it’s grown, how quickly it has spread. There’s really no reason that it shouldn’t bring people along. It shouldn’t leave people behind, versus the digital infrastructure of yesteryear, which was fiber and broadband infrastructure that does take longer to spread and more investment and work to build. This is something that spreads much more rapidly. So we need to be doing a better job of equipping people and communities to ensure that they can positively benefit from it.

Eric Ressler [00:46:35]: So before we wrap up, I want to ask one other thing. As a leader — and I think all leaders can relate to this in one way or another — sometimes it’s a grind. Sometimes the work is hard, sometimes it’s difficult, especially when we’re trying to grapple with these existential technologies or major cultural shifts that are happening, or even just get through a community meeting when we’re really trying to do our best job to listen. What in your life keeps you energized about this work, keeps you going, helps you wake up every day and not burn out when especially things get tough?

Taylor Stuckert [00:47:05]: I think for me, I try to be present in these moments. I try not to dwell too much on the past or feel too overwhelmed about the future, to remain grounded in the present and recognize that for as much as we read articles and studies and information and listen to podcasts, that they’re just signals. It’s not a tablet coming down from on high that’s telling us what the future is. I still believe that the future is unwritten, and that we are the authors of that story. What keeps me going through the grind and being hopeful — I love hearing what our individual service members are doing across the country. They’re not the ones that are on podcasts being spotlighted often, but they’re the ones that are sitting with that older adult, showing them how to use telehealth technology.

They’re sitting with a group of folks from the community going through AI images and quizzing them on what’s real and what’s not real. Those little things that are going to be critical for us to bring people along, that’s the work that gives me goosebumps. Whatever I can do to provide the resources or the means, the mission framing that enables that work to happen, that’s what motivates me. I think that the future is largely unwritten. They’re the ones that are writing it in community, and I’m just here to support them.

Eric Ressler [00:48:45]: I think that’s a beautiful note to end on today. Taylor, thank you so much for joining me. This is great.

Taylor Stuckert [00:48:50]: Yeah, thank you, Eric. Appreciate you having me on.

Eric Ressler [48:30]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Most nonprofit leaders have been through some version of the brand strategy process. The board retreat, where everyone debates whether “empowerment” or “transformation” belongs in the mission statement. The persona exercise where someone invents a 34-year-old Prius-driving mom of two to represent an entire constituency. The tagline brainstorm that eats up a full afternoon and produces something no one will remember six months later. Eric calls it process theater: work that sounds great in proposals and looks impressive on a timeline, but halfway through, everyone in the room is quietly wondering what they’re actually building toward.

This episode puts ten common elements of brand strategy on trial. Eric and Jonathan each rank them as essential, important, or overrated, and the results surface a real philosophical divide. Jonathan, coming from the executive director seat, keeps returning to self-awareness as the throughline: an organization that deeply knows its values, its audience, and the specific value it delivers to the world has the foundation for everything else. Eric, working as the branding strategist who inherits the output of these processes, keeps seeing the same trap: organizations that pour months of effort into the wrong elements and emerge with jargon-filled statements that sound impressive and communicate nothing.

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Where they genuinely disagree is on brand values. Jonathan ranks them essential; Eric calls them overrated. Jonathan argues that values should inform hiring, culture, and how leadership shows up every day. Eric’s response is: “Compelling argument. No one does that.” They end up aligning on a nuanced middle ground, but the tension reveals something important about the gap between how brand strategy is supposed to work and how it actually plays out in practice.

Episode Highlights:

[00:01:00] Brand strategy has a “process theater” problem
[00:03:00] Mission and vision statements: both rank them overrated
[00:05:00] Brand values: essential or a motivational poster trap?
[00:09:00] Why positioning and niche is the most undervalued element
[00:13:00] Taglines: “No one gives a shit about your tagline”
[00:14:00] Audience segmentation vs. the persona exercise trap
[00:19:00] Brand voice and tone: important, but only after the essentials
[00:22:00] Value proposition: Jonathan’s “God tier” pick
[00:26:00] Theory of change: comic books over engine schematics
[00:30:00] The four questions that replace your entire brand strategy

Notable Quotes:

[00:01:20]: “Sometimes these processes can be overinflated, a bit of process theater. Things that sound great in proposals, and then halfway through you’re like, ‘What are we even doing here?’” Eric Ressler

[00:05:35]: “I need to know what my values are as an organization to build my team, to build my board. That’s going to inform who I hire, how I show up, how I expect others to show up.” Jonathan Hicken

[00:07:15]: “I see these values that are so ubiquitous they essentially mean nothing. Integrity, empathy. That version of brand values is more common and is a trap.” Eric Ressler

[00:12:30]: “As an executive director, knowing what your niche is, is like a stress reducer. When other organizations pop up, rather than being fearful, you can just be like, ‘Oh no, that’s a different thing.’” Jonathan Hicken

[00:23:30]: “We cannot assume that because we’re doing something that might feel good, or that our staff and volunteers really care about, that we are bringing meaningful value to our community.” Jonathan Hicken

[00:24:05]: “Working on solving a valuable or important problem is not in and of itself a value proposition. That is a mission.” Eric Ressler

Resources & Links:

• Cosmic — Eric Ressler’s creative agency for nonprofits and mission-driven organizations

• Seymour Marine Discovery Center — Jonathan Hicken’s organization at UC Santa Cruz

• WeDo (Women’s Environment and Development Organization) — Global advocacy org referenced as a case study for distilling complex work into clear messaging

• Santa Cruz Museum of Art & History Theory of Change comic

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:00]: I think you need to know what your values are as an organization to build your team, to build your board. I need to know those things because that’s going to inform who I hire, how I show up, how I expect others to show up. And I need to know that deeply about who I am and bake that into my brand strategy.

Eric Ressler [00:00:20]: Compelling argument. No one does that. That’s my take.

Jonathan Hicken [00:00:25]: Bullshit. I do that.

Eric Ressler [00:00:25]: I’m Eric Ressler.

Jonathan Hicken [00:00:25]: I’m Jonathan Hicken.

Eric Ressler [00:00:25]: And this is Designing Tomorrow.

Eric Ressler [00:00:30]: Okay, Jonathan. I’m very excited for today because we’re going to continue talking about brand strategy and strategy in general. And I thought it’d be really fun to do... Have you ever seen these tier ranking YouTube videos or podcasts before?

Jonathan Hicken [00:00:45]: Oh yeah. I listened to Bill Simmons podcast and he does this with sports all the time.

Eric Ressler [00:00:50]: Okay, cool. So we’re going to give our shot at this, but we’re going to be tier ranking the elements of brand strategy.

Jonathan Hicken [00:00:55]: Awesome. Amazing.

Eric Ressler [00:01:00]: What even is brand strategy? We just did an episode. What the fuck even is strategy? We’re going to keep going deep on these things. So as a designer and a branding guy, I think deeply about brand strategy. We do a lot of brand strategy work with our clients, but there’s a lot of these different elements of brand strategy like mission and vision and niche and all these things. And sometimes, frankly, I look at our brand strategy process and framework almost every year and I’m like, how can we simplify this? Because I do think sometimes these processes can be overinflated, a bit of process theater, things that sound great in proposals. And then halfway through you’re like, “What are we even doing here?” So today, I hope we can get more clarity for our listeners around, yes, you do need a brand strategy. And what does that mean exactly and what are the elements that matter and what are some of the elements that are in fact overrated and not as important as we think they are?

Jonathan Hicken [00:01:55]: I’ve got my elements tiered out here, man. I’m ready to get into it.

Eric Ressler [00:02:00]: So the other thing I just want to tease is that we’re going to talk a lot about all these different elements of brand strategy and it’s going to probably feel maybe even a little overwhelming to some of our listeners.

Jonathan Hicken [00:02:05]: Sure.

Eric Ressler [00:02:05]: I think at the end of the day, this really boils down to four questions that you need to be able to answer as a leader for an organization. And so once we get through the tiering, I’m going to ask those four questions, give an example, and hopefully that’ll be a nice summary takeaway for today.

Jonathan Hicken [00:02:20]: And just to be clear, we’re not talking about people strategy, we’re not talking about financial strategy, we’re talking about brand strategy, limiting it there, right?

Eric Ressler [00:02:30]: I think so. And I would say that brand strategy should influence some of those decisions.

Jonathan Hicken [00:02:30]: Yeah, and vice versa.

Eric Ressler [00:02:30]: And vice versa. But yeah, we’re talking about brand here, baby. Okay.

Jonathan Hicken [00:02:30]: Sounds good.

Eric Ressler [00:02:35]: All right. So here’s where we’re going to start. We’re going to go and I’m going to have you rank first and then I’m going to rank for each of these. And we’re going to start with the most common one of mission and vision statements. And just to be clear, we’re going to rank these on three different tiers basically. So is it essential? Is it important or is it overrated?

Jonathan Hicken [00:03:00]: Overrated.

Eric Ressler [00:03:00]: Oh, I was hoping we disagree on this one. Definitely overrated.

Jonathan Hicken [00:03:05]: It’s definitely... I mean, there’s baggage to this one, right?

Eric Ressler [00:03:10]: Especially for me.

Jonathan Hicken [00:03:10]: There’s a century of history and mission and vision statements. And there’s a whole... When I say overrated, it’s all that stuff. So it’s not just the “Hey, here’s our mission, here’s our vision.” I think there’s value in those things, but when we think about mission and vision statement as this process and you got to get your board and everybody involved in a thousand voices to write the perfect sentence, that is the thing that’s overrated.

Eric Ressler [00:03:35]: Yeah. Unfortunately, we’re perfectly aligned on this one. I was hoping we get some early disagreement, but yes, I think you need a vision statement. I think you need a mission statement. I think you should even think deeply about those things. What I see doing a lot of these and clients coming and hiring us to help them build some of this out as part of their brand strategy and their messaging strategy is that they get an outsized amount of effort and the impact of them is usually not very important. And so yes, we get into wordsmithing land really early. We get into, “Oh, well, the board member thinks this word needs to be in there and oh, we’re forgetting about this one program that’s really important too.” And so then what inevitably happens is you end up with these jargon filled laundry list mission and vision statements that people read and you’re like, “Oh, well, that sounds cool and I have no idea what you do.”

Jonathan Hicken [00:04:25]: I think what ends up happening is we try to use these mission and vision statements as tools to do a lot of different things when they really serve one purpose and it’s a sales purpose. It’s almost like your elevator pitch. The best version I think of a mission and vision statement is the thing that you tell someone, what does your organization do when you’re in passing? It’s my quick pitch.

Eric Ressler [00:04:50]: So you think about it almost like a little elevator pitch.

Jonathan Hicken [00:04:55]: It’s like a little elevator pitch. And then you should have that. You should have that. But as far as it being central to brand strategy, totally overrated.

Eric Ressler [00:05:05]: Okay. I think we’re mostly in agreement on that one. Let’s keep going. So next one up on the list for me is brand values.

Jonathan Hicken [00:05:10]: Brand values. Okay. I think it’s essential.

Eric Ressler [00:05:15]: Oh, okay. So I have brand values overrated.

Jonathan Hicken [00:05:15]: You go first. Okay. Here’s the disagreement you’re going for. Okay. I think that brand values are essential because it’s a part of defining who you are and knowing who you are. And that’s going to be a thread through all of the items here that I call essential. And that is this deep sense of self-awareness. And I think you need to know what your values are as an organization to build your team, to build your board, to motivate people. I need to know those things because that’s going to inform who I hire, how I train, how I show up, how I expect others to show up. And I need to know that deeply about who I am and bake that into my brand strategy.

Eric Ressler [00:06:05]: Compelling argument. No one does that. That’s my take.

Jonathan Hicken [00:06:10]: Bullshit. I do that. Okay.

Eric Ressler [00:06:10]: Okay. You’re like the only person I know who does that. So okay, here’s my take on this one. I see this similar to mission and vision statements where we choose these words and we did an early episode on brand values. Yeah, we did.

Jonathan Hicken [00:06:20]: We did.

Eric Ressler [00:06:20]: And you impressed me because I was like, this is the smartest way I’ve ever heard anyone articulate how to actually take brand values and put them into action. And it’s funny because we have values at Cosmic and I couldn’t even rattle off what my actual values list is because I didn’t do as good of a job as you’re doing with your brand values. But there are a couple that stick with me. And I remember talking about this in the episode that we did. So one of ours is Kaizen, which is a Japanese word that basically means continuous improvement. And so there’s these values that become very embodied that I can remember and they become, for me, less of a laundry list of things I remember and more of just an embodied knowing and that’s the best version of a value. And I think that that is very important.

And so I hear your argument around knowing that and knowing who you are is really critical. However, what I mostly see is that this is the same trap that we fall into when it comes to mission and vision statement where we come up with these words like integrity and empathy that are so ubiquitous that they essentially mean nothing.

Jonathan Hicken [00:07:25]: Yeah.

Eric Ressler [00:07:25]: Right. So that’s why I somewhat controversially put this in the overrated because that version of brand values is more common and is a trap. And I think especially when they become these “Oh, we’re going to go do a retreat and we’re all going to figure out our values and then we’re going to live our values and we’re going to put them on the website and we’re going to print posters.” I think that’s mostly how it happens. And I just honestly, I don’t ever hear anyone say, “Well, one of our brand values of this is this, and so we’re going to act this way.” So maybe it is more of just an embodied thing.

Jonathan Hicken [00:07:55]: Yeah. I think in the version of the motivational poster, I agree with you that is overrated. If that’s as far as you take the brand values work, then it’s totally overrated, waste of time. If you’re going far enough to incorporate those values into expectations for your people, into your tone, your messaging, right? If you’re integrating those values thoughtfully into other elements of your business, I think that is essential because it helps define who you are for yourself, for your team, for your supporters. But you’re right, that work doesn’t always happen. And so lacking that work, overrated. I can see that.

Eric Ressler [00:08:35]: So phoned in brand values,

Jonathan Hicken [00:08:35]: Overrated.

Eric Ressler [00:08:35]: Okay.

Jonathan Hicken [00:08:40]: I can get on board with that.

Eric Ressler [00:08:40]: Well executed, deep, strategic, integrated, embodied brand values, essential.

Jonathan Hicken [00:08:45]: All right. All right.

Eric Ressler [00:08:45]: Okay. Agreed. All right, let’s keep going. So next we have positioning, differentiation, and we’ll just kind of like, the word I like to use for this is niche.

Jonathan Hicken [00:08:55]: Yeah, essential. Again, for me, this is about knowing who you are, knowing how you fit. This is almost like a flavor of product market fit or service market fit. And I think that you need to know where you sit in your community of focus. That could be community, regional, state, national, international, whatever, but you need to know who you are and how you fit. And I think that clarity is essential to building everything else around it.

Eric Ressler [00:09:25]: This is essential for me too. If I could tier rank my essential tier, this would be the top. And the reason I say that is because in the social impact space, I think this gets... Whereas mission and vision get outsized attention, this gets less attention than it should. And this is where we run into all these different nonprofits who are all working on the same issues in the same way. So not enough differentiation, not enough understanding of where the needs are and where there’s white space opportunities. And this isn’t the same as in the business world where you need to differentiate or you die necessarily because we’re not in competition with one another. We’re in collaboration with one another for the most part. But I think really getting clear on your niche is absolutely critical because everything else is downstream of that.

And I think we’re starting to see some themes here. So we spend a lot of time when we work with our clients helping them figure out how are you positioned in, the way we like to describe it, the broader social impact ecosystem. And there are different levels you can look at. You could look at that regionally, you could look at that in terms of the skillset. I often think about this as, what is your sweet spot? What is unique about how you do your work that you can claim that is different and advantageous to creating an impact in ways that even peers in your social impact ecosystem wouldn’t be able to claim in the same way? Getting really clear on your niche to me unlocks all kinds of amazing things. And maybe I’m a little biased here because when we decided to niche in on the social impact space, there was this fear that I had around, well, now I’m pigeonholing myself and now I’m going to say no to all these opportunities.

But as we talked about in previous episodes, saying no is strategy, right? That’s one of the hardest things about having conviction with the strategy. So to me, niche is just probably the most important and most undervalued element of brand strategy in this space.

Jonathan Hicken [00:11:15]: You mentioned competition versus collaboration. And I think that having your niche well-defined actually is a benefit for collaboration.

Eric Ressler [00:11:20]: Agreed.

Jonathan Hicken [00:11:25]: Yeah. Because you can show up to the table and you can say to your collaborators, “Here’s our piece, and that’s your piece. And if we put these pieces together, we can do great things.” In some of the collaborative situations or the conversations I’ve been in, lacking that clarity on your niche can just lead to this nebulous confusion about how we want to work together, but we don’t really know how.

Eric Ressler [00:11:50]: I think that’s so true. And also someone who before felt like they might be in competition with you now suddenly become more of a collaborator.

Jonathan Hicken [00:11:55]: Correct.

Eric Ressler [00:12:00]: And you can say clearly, no, this is actually not our sweet spot, but this org over here who’s very adjacent to us would be a perfect fit for you.

Jonathan Hicken [00:12:05]: Exactly.

Eric Ressler [00:12:05]: And vice versa. I think also being clear on your niche is magnetic for referrals and introductions and that natural networking that happens because if someone knows you and they’re like, “Well, they’re in the climate environment space, but I don’t really know exactly how they’re different or unique in any way or what exactly they do,” then how are they supposed to introduce you to the people who are going to help move your mission forward?

Jonathan Hicken [00:12:30]: Last thing I’ll say as an executive director, knowing what your niche is, is like a stress reducer.

Eric Ressler [00:12:35]: Oh, huge.

Jonathan Hicken [00:12:35]: It’s a huge stress reducer because when news of other organizations or other things pop up, rather than being fearful that “Oh, they’re going to beat me or they’re going to attract more gifts or whatever,” if you have your niche, you can easily just be like, “Oh no, that’s a different thing.”

Eric Ressler [00:12:50]: The way that I think about this sometimes, to just piggyback off that, is you’re predeciding how you’re going to act in the future. And it’s not niche isn’t the only way you do this, this is just about boundary setting in general. It’s like, I’m going to make the decision now so that in the future when there’s some deliberation that might happen, I don’t have to spin out on it mentally. That mental taxation just goes down immediately because it’s like, I’ve already made this decision three months ago.

Jonathan Hicken [00:13:20]: Totally. 100%. Then you can just do it.

Eric Ressler [00:13:20]: So

Jonathan Hicken [00:13:20]: If for wellness alone, I recommend that you develop your position and niche. Yeah.

Eric Ressler [00:13:30]: Okay. Next one. Tagline.

Jonathan Hicken [00:13:30]: Overrated.

Eric Ressler [00:13:30]: Overrated. Taglines are overrated. People love taglines. They want their taglines. They think their tagline is the most important thing. If only we just had the perfect tagline, all of our problems would be solved. No one gives a shit about your tagline.

Jonathan Hicken [00:13:45]: Nah.

Eric Ressler [00:13:45]: I mean, maybe if you’re Nike, and that’s the one example of a tagline that people actually remember that’s any good. The other big trap that people fall into with taglines is they’re like, “The tagline must describe who we are.” Just like the logo must visually represent who we are, another common mistake. And no, it doesn’t and you don’t need one. That’s my take on it.

Jonathan Hicken [00:14:05]: Honestly, I don’t think we need to spend too much time on this one because it’s overrated. Don’t spend time on it.

Eric Ressler [00:14:10]: Okay. Listeners, no more taglines allowed, unless you can come up with a really good one. All right. Next one should be interesting. Audience segmentation and personas.

Jonathan Hicken [00:14:20]: Essential.

Eric Ressler [00:14:20]: Essential. Okay.

Jonathan Hicken [00:14:20]: Essential. And again, this is about understanding who you are and who you serve and just this deep sense of self-awareness. And I have a background in tech, so there’s also just, this was hammered into me early in my career on understanding the customer and everything. So I think deeply understanding your customer or your constituent or whatever word you use, that has to be crystal clear. As you’re making decisions and building programs and iterating, you have to have that always in focus when you’re making those decisions and you need to be able to segment. Just a quick example from Seymour Center. We have this fabulous educational program that’s a field trip to our center. You probably went to something like this when you were a kid. Our kids are going to be coming to this program, I’m sure, here soon. On the surface, it seems like it’s a youth program. I actually think it’s a teacher program.

Eric Ressler [00:15:20]: Yeah.

Jonathan Hicken [00:15:20]: So I think we’re actually providing more of a value to teachers, not to say we’re not serving the kids and providing value there, but when we think about designing this program, we’re actually designing it to meet the teacher’s needs first. So anyway, that’s just one little example of how we’re using audience to make decisions internally. And it’s because we know who we are and what this program’s all about.

Eric Ressler [00:15:45]: Okay. So I have audience segmentation and personas in important, but not essential. And I think it’s because of the persona that put me that way.

Jonathan Hicken [00:15:55]: The activity of creating the persona.

Eric Ressler [00:15:55]: Yeah. To me, this goes back into that performative process theater side of things. So I agree. Knowing your audience, knowing who you are for, and actually that example you gave is great because the audience you think you’re for, I really recommend a peeling of the onion style exercise for this of just really deeply questioning some of these assumptions around “Oh, we serve kids.” It’s like, “Okay, but who are you actually serving in that scenario?” That pushes me up into essential when you start to think about it that way. Persona exercises irk me because they feel reductive and in a way that’s not actually helpful for moving processes forward. It feels like you’re trying to... And just to be clear, when we’re talking about personas here, it’s like, “Oh, our audience is a 34-year-old Prius driving mom of two.” And it’s just like, no, it’s not. You’re taking an entire population of people and trying to... And I get why people do it, right? Trying to paint a more human relatable version of that. Again, I think too much time and energy gets put towards that.

We do audience strategy work at Cosmic, as you could imagine. We do audience surveys, et cetera. The way that we segment our audiences, and we’re obviously biased because we’re looking at this from a brand communication standpoint, is there a meaningfully different message that needs to be developed for that audience? If yes, new audience segment. If no, figure out where to lump them in. And I found that that’s a really pragmatic and practical way of breaking down audiences without... We don’t do any personas. No one has ever come to us and said, “Oh, the process was so great except we didn’t do personas.” And I think that’s meaningfully hurt our success here.

So I would say ditch the personas, audience segmentation, get very clear about who you know and who you’re trying to reach and what you know about them. Segment based on is there a meaningfully different message or story that you need to tell to them? And I think that’s probably good enough.

Jonathan Hicken [00:17:45]: Yeah. I mean, here’s a really easy shortcut for personas. Just picture somebody that you know that fits that persona. Boom, done.

Eric Ressler [00:17:55]: Yeah.

Jonathan Hicken [00:17:55]: And you

Eric Ressler [00:18:00]: Don’t need to define them. And you do need to acknowledge that a persona and a segment is a group of many people.

Jonathan Hicken [00:18:05]: Exactly.

Eric Ressler [00:18:05]: But when you start to get hyper specific about what kind of music they listen to...

Jonathan Hicken [00:18:10]: Yeah, all these fictitious things that... Yeah, I agree. That’s not helping anybody. Never research-based, by the way, just totally vibes all the time.

Eric Ressler [00:19:15]: Brand voice and tone.

Jonathan Hicken [00:19:15]: Ah, important but not essential.

Eric Ressler [00:19:20]: Okay. We’re aligned there. Brand voice and tone, I think can be a superpower for certain brands who are willing to be bold with that. Most are not. But to me, it’s only helpful to have a strong brand voice and tone if some of the more essential elements of your brand strategy are strong.

Jonathan Hicken [00:19:40]: So you agree, important but not essential?

Eric Ressler [00:19:40]: Agree.

Jonathan Hicken [00:19:40]: Yeah. For me, the items that fit into this bucket are ones where it’s really about expressing who you are and I feel like expressing who you are comes after knowing who you are.

Eric Ressler [00:19:50]: Yes.

Jonathan Hicken [00:20:50]: And so to me, this is an example of a way that you’re going to express things like position and niche and your clarity on audience. And so it’s just the expression piece. I think you need to be good at that, but it’s important and not essential.

Eric Ressler [00:20:05]: And I think if you think of it as essential, that’s a trap because what I’ve seen sometimes is people skip the truly essential work and try and just mask it over with a really hip voice and tone that sounds forward thinking, but actually is empty inside when you open it up. So I think yes, it’s important to have a brand voice and to have a tone and have that be consistent. You don’t want staff writing things in certain ways or speaking in certain ways or having a certain message that’s dissonant with how your leadership is talking. So having a unified voice as a brand is truly important, but it should not be the thing that you elevate.

Jonathan Hicken [00:20:45]: Yeah. Agreed.

Eric Ressler [00:20:50]: Okay. Let’s keep going. Brand story and messaging.

Jonathan Hicken [00:20:50]: Important, but not essential.

Eric Ressler [00:20:50]: Important but not essential. We’re aligned. And the same argument as the last one.

Jonathan Hicken [00:20:55]: Yeah. Yeah.

Eric Ressler [00:21:00]: What do we mean when we’re talking about a brand story? To me, this is almost more where I think about the elevator pitch. When you run into someone and they’re like, “Oh, you work at this org, what do you guys do?” That’s your brand story, right? And it should be, that’s an elevator pitch version of it, but it’s your narrative. It’s how you talk about the work. You can, again, process theater this thing and write this massive thing. We’ve been trying to cut these down more and more. When we deliver brand stories and messaging for our clients, if we’re not doing audience specific messaging, we have the brand level one. We write a page version, a half page version, a paragraph version, and one that you can put on your social profile. Done. And they’re all basically the same. They’re just cut downs. So it’s when someone’s like, “Hey, we need a one pager about you.” You have a boilerplate that’s accurate, that’s aligned with the rest of your strategy. You’re not cobbling it together with ChatGPT last minute. So that’s all that you really need for that.

Jonathan Hicken [00:21:55]: Yeah. Don’t work on your brand story until you know yourself and you really know what your story is, right? That’s ultimately what we’re saying here.

Eric Ressler [00:22:00]: I think so. Okay. Next one’s an interesting outlier. Not to be confused with values, your value proposition.

Jonathan Hicken [00:22:10]: I’m going to zag on you here, Eric. I created a new tier.

Eric Ressler [00:22:15]: Whoa. You can’t do that. That’s not allowed. There’s three tiers, man.

Jonathan Hicken [00:22:20]: S tier, God tier. This is the top. This is tops for me. You said you put positioning niche as your number one in that. I’m like, I think it’s value proposition.

Eric Ressler [00:22:35]: Okay. I feel like most nonprofits, especially social impact orgs, don’t even think about this.

Jonathan Hicken [00:22:40]: Yeah. Well, that’s a problem.

Eric Ressler [00:22:40]: I mean, do you agree?

Jonathan Hicken [00:22:45]: Well, I think it depends. I really do. I think that some, at least the organizations I’m familiar with, some really get it more than others. So the reason why I think that value proposition is the most important thing, because why does any business of any type exist other than to deliver some value to the world? I mean, to me, I think it is the very essence of working in any organization that you want to make better.

Eric Ressler [00:23:20]: I think that’s true, but I think a lot of nonprofits especially assume that their value is obvious and inherent in just being a nonprofit.

Jonathan Hicken [00:23:30]: Yes. A, yes. B, be better. We can’t assume that because we’re doing something that might feel good or something that we might really care about as individuals, or even that our staff and volunteers really care about it, we cannot assume that we are bringing meaningful value to our community or to whatever our sphere of influence is. We cannot make that assumption just because we think it’s good or right.

Eric Ressler [00:24:05]: I’m going to take that a step further and say, you can’t make that assumption even if the issue area or the problem that you’re solving is worth solving. Working on solving a valuable or important problem is not in and of itself a value proposition.

Jonathan Hicken [00:24:20]: Right.

Eric Ressler [00:24:20]: That is a mission.

Jonathan Hicken [00:24:20]: So let’s talk about housing homelessness, right? Housing homelessness is important and maybe you’re working on it, but if you don’t know the value that you are bringing to the problem of housing and homelessness, then what are you even doing?

Eric Ressler [00:24:35]: You don’t have a value prop.

Jonathan Hicken [00:24:40]: You don’t have a value prop and you have absolutely no basis to begin your work.

Eric Ressler [00:24:40]: So how do you think about value prop in your work?

Jonathan Hicken [00:24:45]: Yeah. Specifically to Seymour Center? Or just in general, as someone who’s been in the social impact space in a number of different positions.

Eric Ressler [00:24:45]: Sure. Or just in general.

Jonathan Hicken [00:24:50]: Yeah. I get to this... You brought up Kaizen. I’m going to go to another Japanese concept and we may have talked about it on the pod before, Ikigai.

Eric Ressler [00:25:00]: Oh yeah, Ikigai.

Jonathan Hicken [00:25:00]: Yeah. We’ve talked about this, which I think is the intersection of these four pieces, which is something the world needs, something that is economically viable or that you can make money doing, something you’re uniquely good at doing and something that you’re passionate about.

Eric Ressler [00:25:15]: And the Venn diagram where all those four converge is your Ikigai.

Jonathan Hicken [00:25:20]: Right? Yeah, that’s your Ikigai. And that’s where my mind goes immediately: can you define all four of those things for yourself in terms of your organization? And also, the next thing I would do is thinking about audience. We talked about audience for a second. What problem do they have? Would they articulate the problem in the same way you would? And would they validate that the thing that you’re doing is solving that problem?

Eric Ressler [00:25:45]: Yeah. Yeah.

Jonathan Hicken [00:25:45]: So some combination of those things.

Eric Ressler [00:25:50]: Okay. So we’re pretty aligned. I have value prop as essential as well. I didn’t make my own fake tier and break the rules, but yeah, value prop is high up there and I think underconsidered. I don’t get a lot of nonprofits in social impact orgs coming to us saying, “Hey, we need help defining our value prop.” Although we do get that, it’s a little more rare. We get a lot more people saying, “Oh, we need help rethink our mission and vision.” So something to consider, I think, for our listeners. Okay. Next one, also an outlier to a degree, theory of change.

Jonathan Hicken [00:26:15]: Okay. I think it depends on how we’re going to define this again, right? Because if it’s the process of doing the thing and the flow charts and the infographics and all that stuff, I think that you can get lost in that and it can become a waste of time. But I think at its very core, the idea that you have clarity on how your work produces meaningful impact, I think that’s essential. I think that’s essential. And you have to understand that and you have to understand how the way that you’re using donors’ money, the way that you’re showing up, the actual work that you’re doing is producing impact and that you’re fueling the pieces of that chain that are ultimately getting you to your desired end state.

Eric Ressler [00:27:05]: Yeah. Okay. So I hedged my bet a little and put this one in important because of that, you see these schematic style diagrams of theory of change and you’re just like, “Are we building a car engine here? What’s going on?”

Jonathan Hicken [00:27:15]: Exactly.

Eric Ressler [00:27:15]: So I agree though that you should be able to answer, how do you and how does your organization and how does its value prop and its work actually create change in the world? You got to be able to answer that and you have to be able to answer it in a way that someone who’s a layperson or not in your field as an expert could basically get it. And so I would say also important, if not essential, and I don’t think it needs to be... I remember, I think we’ve talked about this on the show before, but at the Santa Cruz MAH, the Museum of Art and History, the Theory of Change was a comic.

Jonathan Hicken [00:27:50]: Yeah.

Eric Ressler [00:27:50]: I loved that. I was like, yes, more comics, less engine schematics.

Jonathan Hicken [00:27:55]: For theory of change. Yes. And by the way, I’ve never seen a theory of change better than that one.

Eric Ressler [00:28:00]: Yeah, that one’s amazing. And we’ll link to that in the show notes, which I will have to do later and remember to do. I always say that. I’m like, “Why do I say that?”

Jonathan Hicken [00:28:05]: Email us and we’ll send it to you. How about that? Yeah.

Eric Ressler [00:28:10]: Okay. Last one. Number 10 here, case for support.

Jonathan Hicken [00:28:15]: Oh man, see, this one’s tough. This one’s tough for me. Ultimately, I put it into important, even though you and I worked on a case for support for Seymour Center, and it has been so impactful to the point where in my day-to-day work, I would call it essential. For me personally in my work, I need that case for support and it’s been really helpful. And to me, it fits into this bucket of expressing yourself after you know yourself.

Eric Ressler [00:28:40]: Interesting. Okay. I’m going to push back on that one a little bit. I have it in essential. And the reason why I have it in essential, and we can riff on this a little here, I think to have a solid case for support, going through that process forces you, if done well, to answer all of the other essential elements. You have to know what your positioning is and your niche. You have to know what your value prop is. You have to know what you are standing for in the world, all these things. What’s the problem that you’re solving? So it’s a shortcut for forcing you to make the hardest and most impactful and important decisions as an organization. So I put the process as essential. Does every org need a polished... I think sometimes you think of case for support and you think of this report that you put together for a capital campaign, that’s a version of a case for support, right?

Similar to the theory of change for me is, if I ask you, Jonathan right now as the executive director of the Seymour Marine Discovery Center, why should I donate? Why should I support? You should have a pretty good answer for me.

So to me, again, I think a lot of times, and as we wrap up, I think we’ll get into this here, these different elements, there’s all these terms and terminology around, well, what’s a theory of change, a case for support, and it feels jargony. I’m in it every day, so I have deep knowledge of what it means to run these things. But if you’re in a leadership position at a social impact org, what really matters? What’s the distilled version of this? And so I want to leave listeners with a bigger picture takeaway, which is I think that however you describe this stuff, however you think about it, which parts you think are essential or whatnot, there’s really four questions that you need to be able to answer as an organization. And if you can answer those questions, you could basically ignore all of this stuff at some level.

And the first question is, what do you do? The second question is, who do you do it for? The third question is, how are you different? And the fourth question is, why does it matter? I think if you can answer all four of those questions well, you have a brand strategy and you don’t need to worry about all these terms and terminology and all this process.

Jonathan Hicken [00:30:55]: Preach that from the rooftops, my friend, because that’s such a simple thing that literally every listener could take to their next staff meeting, take to their next board meeting and work through that if they don’t already have the answers. It’s such a simple exercise. It doesn’t need to take months and months and hundreds of thousands of dollars to answer those questions. And if you can’t answer those questions, that’s probably really good for you to know. Maybe there’s some problems with your business.

Eric Ressler [00:31:25]: The thing I will also add to that is you would be surprised how many orgs who are well-known, highly successful, and by common metrics of how we measure success in this space, who’ve come in to my door at Cosmic and cannot give me a solid answer on those four questions. And I don’t mean that in a judgmental way. I mean, this is actually, those questions are simple, but they’re hard to answer. And especially if you’re in a moment of transition or stepping into a new chapter as an organization, the answers to those questions may not be relevant anymore. So you might be able, “Well, we were this, but we’re becoming something else, and I don’t really know how to articulate that yet. It’s this vague thing we’re still shaping.”

I wanted to also just share, and I challenged myself to come up with an example that was actually difficult to answer these four questions for. We’ve been working with an org called WeDo for a long time now. They’re amazing. Shout out to them. We just launched a new website, by the way. Go check it out. WeDo.org. They stand for Women’s Environment and Development Organization. Their work is very complex. They do global advocacy work. It’s the kind of org that... And I’ll just be honest, and Bridget, I love you to death, but this was very hard to figure out how to take this super insular advocacy policy. They’re at the UN, they’re at COP. This is deep expertise work. And we still believe this needs to be distilled down into something that someone who’s not in those rooms can understand without dumbing it down.

And so I actually tested. I was like, did we get to a point in their messaging where we could answer those questions? And does it show up on the website exactly like that? No. But I think we did. And so I’m going to test. WeDo could have been a complex global advocacy organization working at the intersection of gender equity and climate justice, but what does that mean? So what do they do? They advocate for gender just climate policy. Who do they do it for? They do it for grassroots feminist leaders and frontline environmental defenders. How are they different? They’ve been doing it for 35 years and they’ve been building coalitions and tools that get women in the rooms where climate decisions are made. And why does it matter? Because we know that when climate policy excludes women, the climate policy fails. Done.

Jonathan Hicken [00:33:50]: Done. Beautiful. That’s wild. Congratulations to WeDo and to Cosmic for that because that’s super powerful. Yeah.

Eric Ressler [00:33:55]: Okay. So Jonathan, this was great. More tier ranking podcast coming up.

Jonathan Hicken [00:34:00]: Yeah, dude, that was fun.

Eric Ressler [00:34:00]: That was fun.

Jonathan Hicken [00:34:00]: Yeah, thanks, Eric.

Eric Ressler [00:34:00]: All right, man. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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“AI only knows how we describe empathy, but it doesn’t know what empathy looks like in practice.”

Tina-Marie Gulley was the CEO of Ada Developers Academy, a tuition-free coding program for women and gender expansive adults. In a moment where everyone is racing to adopt AI and equity programs are being quietly dismantled, she’s doing both at once: embedding AI into the curriculum while refusing to water down the mission.

What’s fascinating is how she thinks about the tension between technology and humanity. She pointed out that the children of tech billionaires often aren’t using AI in school the way the rest of us are pushing it on kids. That disconnect says something worth sitting with.

We also talked about what happens when funding dries up. Her take was sharp: impact reporting shouldn’t stop when the checks stop. If a funder gave you $10,000 ten years ago, they should still be hearing about what that investment made possible. That’s how you build relationships that outlast grant cycles.

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Episode Highlights:

[00:01:00] From corporate marketing to nonprofit CEO: how a computer science competition revealed tech’s inclusion problem
[00:02:00] Why technology hasn’t fulfilled its promise of closing the digital divide
[00:04:00] Why nonprofits are slower to innovate and what Ada is doing differently
[00:05:30] Using vibe coding and hackathons to build real solutions for nonprofits
[00:07:00] Cutting through the AI hype cycle: grounding innovation in mission
[00:09:00] The hidden human cost behind AI, from data centers to the communities around them
[00:10:00] Why AI should never replace your therapist
[00:12:00] Working in community with AI and the risk of treating machines like people
[00:17:00] Investing in AI means investing in humanity, and in unplugging
[00:18:00] Why billionaires’ kids aren’t using AI in school the way everyone else’s are
[00:21:00] Reframing DEI in a hostile political climate without compromising on impact
[00:23:00] Navigating the funding shakeup and keeping funder relationships alive after the checks stop

Notable Quotes:

[00:02:20]: “People get really excited about innovative creations and creating the next unicorn, but they don’t really think about all the pieces that drive that. Making sure that they’re in the room at the start versus as an afterthought.” Tina-Marie Gulley

[00:07:55]: “People get so enamored with this new shiny thing that they forget how it can also further exaggerate inequalities.” Tina-Marie Gulley

[00:11:10]: “AI only knows how we describe empathy, but it doesn’t know what empathy looks like in practice.” Tina-Marie Gulley

[00:16:00]: “Are we gaining efficiency and more technology and more information? But what is the cost of that? Are we losing pieces of our deep humanity?” Eric Ressler

[00:17:00]: “A big part of investing in AI is investing in humanity. And that means investing in ways where people are able to unplug.” Tina-Marie Gulley

[00:25:15]: “A lot of times the impact reporting stops once the checks stop, and I don’t think that’s fair.” Tina-Marie Gulley

Resources & Links:

• Ada Developers Academy — Tuition-free nonprofit coding academy for women and gender expansive adults

• AI2 Incubator — Seattle-based AI startup incubator; Ada partners with AI2 on the AI House initiative

• AI House at Pier 70 — Public-private AI hub in Seattle launched in partnership with the City of Seattle, AI2 Incubator, and Ada Developers Academy

• Tina-Marie Gulley on LinkedIn — Connect with Tina-Marie directly

• Imagine Cup — This is Microsoft’s global student technology competition.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:00:45]: Tina Bree, thank you so much for joining me today.

Tina-Marie Gulley [00:00:45]: Thank you so much for having me.

Eric Ressler [00:00:50]: So your career began in corporate marketing and I’m curious to hear how you got from there and maybe what pivotal experiences moved you from that world into being an executive as a nonprofit CEO.

Tina-Marie Gulley [00:01:05]: So actually one of my first jobs, I was doing marketing and we were managing Imagine Cup. And so that’s a big computer science competition. And that was one of the aha moments where I was like, “Hey, this is so cool, but it doesn’t seem like there’s a lot of opportunity for people that are diverse or I just don’t see them in the room.” And so that was my first indication of, “Oh, tech is not really as inclusive as I thought it could be.” And so through there, I just started building my career and I did a lot of the work around equity, education for folks that are often not part of the conversation as a volunteer. I really am passionate about creating opportunity for people that maybe are underestimated.

Eric Ressler [00:02:00]: Technology has this promise of bringing us closer together, of closing these digital divides, of being a way to get past some of these issues of inequity and inequality. Why do you think it hasn’t fulfilled that promise?

Tina-Marie Gulley [00:02:15]: I think that people aren’t as intentional as they could be. I think people get really excited about innovative creations and creating the next unicorn, but they don’t really think about all the pieces that drive that. So not only your customer base, but also the people who are creating those innovations. So making sure that they’re in the room at the start versus as an afterthought. I think it’s really about creating opportunity for folks that maybe wouldn’t necessarily have that opportunity and really thinking about, okay, what kind of future do we want to build? Do we want to just continue building these systems that really do us all harm or do we really want it to be intentional from the start and really see it evolve from there? I think a big part of that is just really making sure that we as individuals, as we’re creating rooms, as we’re having a seat at the table, that we’re looking at who’s missing and who could really make a difference in evolving this idea, this innovation, this thing that we’re trying to move forward to adapt and problem solve for.

Eric Ressler [00:03:35]: You used the word innovation and coming from the tech world, that’s a term that’s used a lot to describe experimentation. Use the word unicorn, these new bold ideas, these white space ideas. How have you experienced the transition from the tech world into the nonprofit space? Another space that talks a lot about innovation, but I don’t think is really set up properly always to facilitate that kind of research, that experimentation, a willingness to be bold, a willingness to experiment and to fail. Has that been a bit of a culture shock for you or have you been able to bring that spirit of innovation through your career path?

Tina-Marie Gulley [00:04:10]: I think that Ada is one of those anomalies where we’re creating that intentionally and to what we’re doing every day. I do see that oftentimes nonprofits are slower to innovate, slower to invest in things like AI, slower to improve their systems. And so fortunately, that’s not our situation at Ada. We really think of those things at the, how we can continue to be cutting edge and take some of those elements from businesses and bring that into our organization as a nonprofit and as an education technology provider or institution. And so I don’t see us having that issue, but definitely as I talk to other nonprofits, I definitely see that there is a lag behind. What’s really exciting though is that we’re seeing a lot of forces joining together to bring innovation to organizations. We actually did that most recently. We had a hackathon where we were really trying to solve for real world issues for other nonprofits and community organizations.

And we did that through what’s called vibe coding now, which is a lot of prompting and making it more accessible for people. And so we were really building solutions that we know that nonprofits can use and take and iterate on. And so I’m seeing more of that. I’m also seeing more opportunities for partnerships, solution innovation partnerships with different organizations. I know Salesforce is doing it. I know JP Morgan Chase and a host of other organizations are doing it where they are bringing in re-imagining, hey, if you were to bring AI into your organization, what would it solve for? Would it help improve curriculum? What are the things that you can create? So I think there’s lots of avenues where these forces are joining together. We don’t have to be so distant, but we also can learn from each other. A big portion of, I think, working in nonprofits is around the impact of people in a way that businesses don’t necessarily think about.

Eric Ressler [00:06:40]: So AI is this new technology, this transformational opportunity, and it’s very controversial change, a lot of fear, a lot of uncertainty around it. And I think a lot of that is grounded in good, healthy skepticism and criticism. And at the same time, a lot of potential. And everyone’s trying to figure out how AI fits into their work, into their life. How are you thinking about how AI fits into your work, into your mission, into the values that drive your work? And what are the things that you’re excited about when it comes to AI and what are the things that you’re cautious about when it comes to AI?

Tina-Marie Gulley [00:07:20]: I think what can be challenging, especially as somebody who works in tech and who’s worked in tech for years is there is a huge hype cycle echo chamber that sometimes happens with these new innovations and things that come out. And so for us, it’s really being grounded in the work that we’re doing, really looking at it as AI is amazing, but it does not replace humans. It does not replace the connectivity. It’s really meant to be your copilot. And so oftentimes people get so enamored with this new shiny thing that they forget how it can also further exaggerate inequalities. And so for us, it’s really grounding ourselves in our mission and our purpose and how can AI help us to solve it. So whether it be internally from an operational standpoint, whether it be embedding it into our curriculum like we did about a year ago, whether it be through partnerships that we have with other orgs as well as the government to see how we can make it more accessible, I think those are the things that I’m really locked in and focused on. As we are creating these pathways for people to have AI, to use AI, to also think about the ethics around AI, also thinking about what goes into the background of AI.

There’s people behind all of this, from the language learning models, from tagging things, from the people that are creating the data centers to the water that is running through the data centers to the communities that are impacted by those data centers outside of their door. And so we really try to be intentional about the way that we’re using AI, where we’re really making sure that when we use it, we’re being constructive with it. We’re just not using it because it makes sense, it’s because it’s helpful, but we also understand the ramifications of all of those things.

Eric Ressler [00:09:35]: Where do you think AI is most helpful when it comes to social impact work and even just in general as it comes to creating social change, doing your work, being a human being even, and where do you think it is not a good fit and where there’s some potential either downsides or even just places where AI is not constructively used or shouldn’t be considered as the first tool in the toolbox?

Tina-Marie Gulley [00:10:00]: Well, therapy is one. I know that is a big one that I’m starting to see the trends that people are using AI as their therapist and those are one of those areas where I say, “No, let’s not do that. Let’s go to our therapist.” It’s really meant to be a copilot. A lot of times, depending on the language learning model that you’re using, AI is meant to please you. It doesn’t want to make you angry. It’s going to tell you what you want to hear. And so we have to take that into consideration. It might give us a perspective based off of the prompts that we put in or what it knows about you. And so we really have to take that into consideration as we’re using it. I really love the idea of co-authoring with people, with humans and the machines to really make a better perspective, to understand all of the nuances.

There are things that AI is just not going to know because it doesn’t have the lived experience of humans. It only knows how we describe empathy, but it doesn’t know what empathy looks like in practice. And so it’s really important for us to make sure that as we are guiding what the future of AI looks like, that we are not displacing people. It’s really meant to be used as an opportunity for you to focus on the areas that you really enjoy doing and all of those minute tasks that maybe aren’t so fun, it can help you solve for that. For me, I think AI is less about productivity and more about figuring out what are those things that people enjoy doing, what are those core competencies that AI can help you with, and what are the things that we need to continue to let people do?

I don’t want us to get into a situation where AI is replacing people. I don’t think that is great. People still have to have a livelihood, people have to pay bills. And I really want there to be a world where we can work in community with AI.

Eric Ressler [00:12:20]: It’s an interesting way of putting it. I don’t think I’ve ever heard anyone quite say it that way, working in community with AI. And it is an interesting way to think about it. And it starts to get almost very sci-fi very quickly around this idea of humanizing this technology in a way that I really don’t think any other technology has been humanized so quickly. At the time of this recording, ChatGPT-5 just rolled out and there’s a whole subculture of the internet freaking out because they miss their old model, not because of the tool element of it, but because almost like they would miss a dear friend who got replaced unexpectedly. This goes back to your point about maybe we shouldn’t be using AI for therapy or in replacement for therapists and the constructive and the skillful use of AI versus a maladaptive use of AI. Does that cultural relationship worry you even when you’re using terms like working in community with AI?

Tina-Marie Gulley [00:13:30]: It worries me all the time. I mean, we’re seeing a proliferation of people having relationships with their AI. They consider their AI their best friend or their romantic partner, and that definitely has me very concerned. I think that there is a way to invest and engage and make AI a part of your community in terms of really improving systems, improving experiences, creating more opportunities, better understanding outcomes. But we really have to think of it as a partnership ecosystem versus this is an actual community member. And we can definitely build together and create the next era of things, but it definitely should be led by human beings and not by machines.

Eric Ressler [00:14:30]: I have a bit of a complicated relationship with technology, and I’ll try and explain that briefly here. So I grew up with basically the popular adoption of the internet and have been pretty connected to technology my entire life, personally, professionally. I’m an artist, I’m a designer, I’m a creative, and the convergence of creativity and technology has essentially been my life’s work. And at the same time, and maybe part of this is because I’ve recently become a parent, I have two young kids. I do worry about how technology has so deeply become interwoven into humanity. And I think the internet was a major milestone in this. The smartphone was maybe even a more major milestone because now we are connected everywhere we go. We’re looking at VR and AR and now AI. And it seems like technology is getting closer and closer and more interwoven into our humanity.

I walk around with a smartwatch on and I track my daily steps and I know what my resting heart rate is. And sometimes it can be constructive because it might remind me, “Hey, dude, you got to get up and move a little bit. You can’t just be sitting at your desk all day.” And at the same time, I do worry sometimes, and when I think about my daughters growing up in this world, I worry sometimes about, are we gaining efficiency and are we gaining more and more technology and more and more information? But what is the cost of that? Are we losing pieces of our deep humanity in a way that is leading to some of the cultural and societal issues and the polarization and the loneliness epidemic and maladaptive behavior trends that we’re starting to see show up in data and in science? As someone who’s also very tied deeply to technology and social impact, I’m just curious how you think about that and how you think we might be able to more skillfully coexist with these technologies because it’s not going away. The genie’s out of the bottle at some level. So I think the question is, how do we best... Is it regulation? Is it social and cultural norms? Is it people speaking up and reconnecting with their humanity? Where do you see this going?

Tina-Marie Gulley [00:17:00]: I think a big part of investing in AI is investing in humanity. And that means investing in ways where people are able to unplug, where they’re able to be in areas where we do things without technology, without AI, to have that balance. I think we still have to have opportunities to spark amazing conversations that lead to action that allow us to really be able to use a lot of those soft skills that we’ve already developed as human beings. And so we definitely need to have... I don’t necessarily know if it’s regulation, but it could just be a framework of how to do it properly. So that means not only at work, but in your personal life, at schools. One thing that I find really interesting, I’ve read a couple of articles that were speaking to billionaires and the schools that their children go to, and a lot of times they are not using AI or technology in the ways that other schools are.

And it’s very interesting because these are children of people who are running technology companies. And so it’s really advantageous for us to learn from that, where there has to be balance, where part of what this AI and technology as a whole is supposed to do is democratize some things, but also realize that we have to be able to spark conversations and innovations in natural settings without technology as well. We have to use both sides of our brains to ensure that we’re able to do that. And we’re not living in a world where we are so reliant on technology that the next generations don’t know how to think critically, or they don’t know how to analyze, they just don’t know how to do basic things. And so we do have to have the balance. I don’t know if that’s policy. I don’t know if that’s some type of mandate, but I definitely know that that has to be part of this conversation.

Eric Ressler [00:19:30]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

I want to shift and talk a little bit about diversity, equity, inclusion, given that those are major drivers in your personal life, your lived experience, also the values that shape how you think about your organization. We’re unfortunately in a moment where a lot of those values, a lot of those efforts are being scrutinized heavily, at least in America. We’re in a moment where a lot of funding that was flowing pretty freely towards some of those initiatives in the corporate world, especially in the social impact world, that seems to be pulling way back, even just because organizations don’t want to attract any negative attention or extra scrutiny. What’s the experience been like for you this year navigating all of that as that’s been unraveling in real time? Or maybe you have a different experience and that’s not how you see it happening.

Tina-Marie Gulley [00:21:10]: I think more of it is I want to focus more on reframing it. At the end of the day, we’re trying to create opportunity for everybody, but we really have to focus on what are the challenges to those opportunities. We have to call it what it is. I don’t care if you call it DEI, something else. I really want to scale responsibility. I don’t want to compromise it. I want to make sure that impact is there. I want to make sure that we are able to create those cultural safeguards that these communities need. And I want to be able to feel good about what I’m doing in terms of creating opportunities for folks that are untapped or considered non-traditional and being able to partner with organizations that don’t want to retain these archaic systems that cause everybody to suffer.

For us, scaling really means quality over quantity. That means our students, once they graduate, they’re giving back to our program, not only in mentorship hours or volunteer hours, but also in dollars. We are still addressing structural barriers that are happening, but we’re reframing what that looks like and changing what equity and action also looks like.

Eric Ressler [00:22:45]: I want to pick back up on a thread that we started early in this conversation around innovation, and especially as it relates to fundraising and philanthropy. So you talk about power dynamics with regards to philanthropy and finding the right partners, the reciprocal partners who will fund this work. What’s your experience been like, especially recently with a major shakeup in the funding landscape and the incentive structures that are in place for some of the major donors and most importantly, some of the institutional donors. What’s that experience been like for you this year?

Tina-Marie Gulley [00:23:15]: I think more than anything, there’s a lot of uncertainty on both sides, and that’s definitely relatable. And I think more than anything, we want to make sure that as things get aligned or adjusted as different priorities happen, that we also think about other organizations. There are other organizations that are literally ensuring people are alive and they’re being prioritized and they should be. If there’s a nonprofit that is ensuring people have cancer care, people have a place to live, and to eat, they should be a priority. And I don’t fault any organization that wants to realign to those things. Those are very important. Those go back to the humanity of society, but also knowing that we all play a part. And so really making sure that if it is something where an organization is perhaps shifting in direction, to know how we can still be a part of maybe future conversations, that this relationship hasn’t ended.

And so for us, that’s what’s really important. We really want to make sure that whoever we partner with, that they understand our mission, that we’re mission aligned to the focus of the organization and to know that we’re here, we’re not going anywhere. And even if you’re readjusting the way that you’re distributing grants and funding for the next two, three years, we’re hoping that our mission was so strong, the relationships that you created with us was so strong that you still want to figure out how you can still be involved with what we’re doing. And so it’s really about building those relationships and also showing the level of impact. I think a lot of times the impact stops or the impact reporting stops once the checks stop, and I don’t think that’s fair. I feel like if somebody’s given to you, they should always have those updates of what the organization’s doing, what are some of the things that you’ve rolled out, because that impact has a ripple effect.

And it’s important for them to see this $10,000 grant that you gave us 10 years ago has allowed us to accomplish all of these things. So I think it’s really important to have those mechanisms where you’re still reporting back to funders way after maybe their relationship has formally ended.

Eric Ressler [00:26:00]: Before we wrap up, I want to ask you something a little bit more personal about how you show up in this work. And no one comes into this work and dedicates their life to doing social impact work because it’s easy. Being up at the top as a leader, not to get too hierarchical with it, but it could be lonely at times, it could be hard at times. What do you do when it gets hard for you? What keeps you going? What keeps you energized doing this work, especially when it gets hard? How do you balance all that? How do you prevent yourself from burning out, from losing hope and motivation for the future as it relates to technology and just in general, how you show up every day in doing this work in community?

Tina-Marie Gulley [00:26:45]: I think I have to ground myself in who I am and what I can control. And that’s a big thing that I do with my team as well. I think it’s also important to always just have a mindset of continuous learning. You might be an expert in all of these areas, but there’s so many more areas that you have to learn from or learn about. And I think the other thing is being able to unplug, rest, rejuvenate. I think that naturally, a lot of us didn’t even know what that looked like, like work-life balance, what is that? I don’t know her. And so being able to prioritize rest. I’m always a big proponent: when your body tells you to rest, you do it or it’s going to make you rest. And I think I’ve learned that so many times. If you are not filling your own cup, you can’t fill other people’s cups.

Eric Ressler [00:27:45]: That’s beautiful. Thank you. What are you personally most excited about right now as it relates to the work that you’re doing or even just in your own life? What are you looking forward to?

Tina-Marie Gulley [00:27:55]: My goodness. I think that I’m most looking forward to creating new partnerships. I think that we’ve started this year with some amazing partnerships with the city, with the state, with other nonprofits, with AI2 Incubator. And I’m really excited about where that is going. I think that a lot of times we’re just so focused on ourselves or our organizations that we don’t think about the totality of what we can do when we come together. And so that’s what I’m looking forward to is more community and private partnerships to ensure that people are being able to be a part of society, able to make sure that they’re part of the workforce, able to make sure that they’re contributing in lots of different ways that we find the value in the different ways that folks in our communities can contribute. So that’s what makes me really excited right now.

Eric Ressler [00:29:00]: Awesome. For listeners who want to learn more about your work, to connect with you, where can they go? Where do you want to plug?

Tina-Marie Gulley [00:29:10]: Yeah, please visit us. Our website is adadevelopersacademy.org, and I’m on LinkedIn. I am Tina-Marie Gulley, G-U-L-L-E-Y. That’s a great way to plug in with me. And definitely at an event. I try to go to a lot of tech, social impact events, as well as my team. We’re a small but mighty and approachable team, and we really believe in the best in people.

Eric Ressler [00:29:45]: Tina Marie, this has been awesome. Thank you so much.

Tina-Marie Gulley [00:29:50]: Thank you.

Eric Ressler [00:29:55]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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There’s a post going around LinkedIn right now where a fundraiser is calling out a foundation for not structuring a grant as multi-year support. The tone is essentially: our work matters, so funders should give us what we need.

That sparked the thorniest disagreement Eric and Jonathan have had on the show. Jonathan’s take is blunt: nonprofits need to stop treating funders as fuel for their missions and start treating them like customers. Not in a transactional way, but in the way a great customer success team operates, deeply understanding what success looks like for the individual program officer.

He’s so committed to this idea that he’s stopped pursuing competitive grants entirely, opting instead for a relationship-first approach where he only seeks funding from partners he’s actually gotten to know.

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Eric agrees with the pragmatism, but he can’t let the systemic critique go unspoken. These are organizations with massive tax advantages hoarding wealth, spending down the legal minimum, and investing in ways that sometimes directly contradict their stated missions. Trust-based philanthropy is a structural response to a power dynamic that’s been broken for decades.

Eric draws a parallel to his own decision to stop doing RFPs at Cosmic, and Jonathan admits his approach might be its own quiet act of resistance.

Most fundraisers live in this tension every day… they just don’t say it out loud.

Episode Highlights:

[00:00:01] The LinkedIn post that set Jonathan off
[00:02:00] Why funders should be treated like customers, not fuel
[00:03:00] The long-held power dynamic between funders and nonprofits
[00:04:00] Trust-based philanthropy and where it fits
[00:05:30] Jonathan’s case for relationship-first fundraising
[00:06:30] Why Jonathan gave up on competitive grants entirely
[00:08:00] Eric’s pushback: isn’t this a broken system?
[00:11:30] The RFP parallel: why Cosmic doesn’t do them either
[00:13:30] Understanding funder motivations at the individual level
[00:17:00] When foundations abandon their own stated priorities
[00:20:00] Whose job is it to fix philanthropy?
[00:23:00] Entitlement as an excuse for not being fundable

Notable Quotes:

[00:02:10]: “We need to stop thinking of philanthropic funders purely as fuel for our missions and more like customers that we deeply need to understand and serve in their own right.” Jonathan Hicken

[00:03:10]: “There’s a long-held power dynamic in the space of social impact where funders basically hold all the power because they’ve got the money.” Eric Ressler

[00:05:25]: “If I deeply understand what my funders are trying to do, that puts me in a position where I’m actually seen as an ally and a partner rather than a hungry mouth to feed.” Jonathan Hicken

[00:23:00]: “If you’re commenting on systems change, fantastic. Let it rip. If you’re talking about actually going after money, the entitlement tone is hurting all of us.” Jonathan Hicken

[00:24:15]: “How can we build social impact organizations that are not constrained by resources, but can sit there and imagine and do bigger work and not always be stuck in scarcity or reactivity mode?” Eric Ressler

Resources & Links:

• Stupski Foundation — Spend-down philanthropy referenced by Eric; Jennifer Nguyen was a previous guest

• Jennifer Nguyen’s article on abolishing philanthropy

• Rusty Stahl episode — Recent guest discussing new fundraising mechanisms.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:00]: I think that we need to stop thinking of philanthropic funders purely as fuel for our missions and more like customers that we deeply need to understand and serve in their own right.

Eric Ressler [00:00:15]: Interesting.

Jonathan Hicken [00:00:15]: I get the feeling you got some things to say about this.

Eric Ressler [00:00:15]: I have opinions. As fundraisers, as leaders and organizations doing this work, really understanding motivations and trying to attract right fit partners for our work. But the longer I’ve been doing this work and also just seeing some of the frankly shitty downstream effects from some of these funders who, let’s remember, have tax benefits to being set up this way, have hoarded massive amounts of wealth, so they’re in this position of privilege and power. And so we should hold them to a very high standard.

Jonathan Hicken [00:00:45]: Okay.

Eric Ressler [00:00:45]: Yeah.

Jonathan Hicken [00:00:45]: Are you ready to get into it?

Eric Ressler [00:00:50]: Let’s go. I’m Eric Ressler.

Jonathan Hicken [00:00:50]: I’m Jonathan Hicken.

Eric Ressler [00:00:50]: And this is Designing Tomorrow.

Jonathan Hicken [00:00:55]: All right, Eric. There was this post on LinkedIn the other day that nearly had me throw my mouse against the wall. It was from a fundraiser, I’m not naming names, that was talking about how this foundation wasn’t structuring a grant in a multi-year way, and it was a call for foundations to structure their giving in a way that met that particular organization’s needs. And it came off to me as totally out of touch and very entitled with an assumption that the work is so important that the funders should acquiesce to our needs. And the first thought that came to mind was, “No, dude, it’s completely the other way around.”

Eric Ressler [00:01:40]: Mm.

Jonathan Hicken [00:01:40]: And so I wanna unpack this idea that funders actually don’t owe us anything as nonprofits and what that actually means. At the end of the day, I think that we need to stop thinking of them purely as fuel for our missions and more like customers that we deeply need to understand and serve in their own right. And what I mean by that is the individuals — we can bring this down to a human level. The individuals that are working at these foundations, they have goals, they have objectives, they have strategy that they’re trying to execute. And when we put them in the position that somehow they are not doing right by us, I think that just causes separation in the industry that I don’t think is healthy for anybody.

Eric Ressler [00:03:00]: Yeah. Okay. I think this one’s super thorny. That’s my first take on this one. Thorny, complex, nuanced, use your word, because I can make counter arguments for every argument you just made. So there’s a long-held power dynamic in the space of social impact where funders basically hold all the power because they’ve got the money, right? That’s the general power dynamic. And Jen Nguyen, who we had on the show from the Stubski Foundation, who is clearly an institutional funder — they’re unique because they’re a spend-down philanthropy. This is not the Stubski’s point of view, but it’s Jen’s point of view that philanthropy in and of itself should just be abolished because the structure is so broken. It’s not my take necessarily. I respect Jen’s take and I think that there’s a lot of really good reasoning behind her take on that. She just wrote an article about it, which we’ll link to in the show notes.

I think where this comes from and where we can loop into the movement around trust-based philanthropy, which sounds like this person on LinkedIn was advocating for, is that there is this power dynamic inevitably between someone who has resources and someone who needs resources that’s gonna be there, right? Let’s just acknowledge that there’s gonna be a power dynamic there. And there’s been traditionally a lot of funding that comes in that’s just open call or invite only, however it comes in, there’s a grant opportunity and you can get this. And it becomes this competition, essentially. And a lot of upfront work is required by nonprofit organizations to even win the grant. If they get it, it’s restricted. So they don’t actually have the right resources or structures to do their best work. They’re being pushed into a system and it’s elective, right? They don’t have to apply for the grant, but these organizations need funding to do their work. So I guess I should just come out and say I’m generally a proponent for trust-based philanthropy. I think it is a better way of doing this. I don’t think that’s necessarily at odds with your key takeaway.

Jonathan Hicken [00:05:00]: Yeah, me neither.

Eric Ressler [00:05:00]: So maybe we could just start there and get into some of the details.

Jonathan Hicken [00:05:05]: Yeah. Something that’s coming up for me is where’s the onus of responsibility for changing these things? And I think for me in my position as a fundraiser, as an executive director, I feel like it’s counterproductive to be villainizing my funders rather than spending the time to deeply understand what it is that they’re trying to do and the impact that they’re trying to have, because if I deeply understand that, that’s going to make me more competitive, and that puts me in a position where I’m actually seen as an ally and a partner rather than a hungry mouth to feed.

Eric Ressler [00:05:40]: Okay. So I think that’s a really important distinction, which is we can do both. We can work with funders to be better funders, and we do that by being partners with them, and not expecting them to just bend to our will. Because really at the end of the day, there’s a shared objective here, or there should be, if the partnership is healthy, where there is some impact in the world that you as a practitioner or organization are working to make, and that an aligned funder feels like you are a good fit to help make, right? But I’m gonna push back in a couple ways here. One, I just wanna — my understanding is you’ve basically given up on this style of fundraising.

Jonathan Hicken [00:06:25]: Yeah. We don’t go after these huge competitive grants anymore.

Eric Ressler [00:06:25]: So tell me more about why you made that choice.

Jonathan Hicken [00:06:30]: Well, because rather, what I prefer to do is to go seek out individuals and organizations and build relationships first. So we don’t go after these massive calls where I know that hundreds or thousands of other organizations are gonna apply. Because I have no relationship there. I don’t necessarily understand that foundation’s needs or their goals or the way they think or the way they show up or who they’re looking for. I don’t know any of that stuff. All I have is a website with the requirements for the grant, right? And to me, this comes down to dollars and cents too. How much time and money am I gonna put into this thing with what percent chance that I’m gonna get this grant? I would much rather put my time and effort into developing relationships that is gonna give me a really high chance of getting the gift rather than spinning my wheels on these organizations I know nothing about.

Eric Ressler [00:07:25]: Right. Okay. So I’m gonna keep going on this thread. Doesn’t that feel like a broken system?

Jonathan Hicken [00:07:30]: No, not at all.

Eric Ressler [00:07:30]: So you think it’s okay that these organizations who have gathered wealth in our society, largely because founding organizations have built them as, just be real, a tax haven for the most part. They’ve got all of this wealth and power. They exist legally and in spirit to do good, and they are not spending down, in many cases, more than 5% a year, and they have the ability to. And the structure basically means that you have to have some kind of in to get money because you either already are successful enough, or because you have a personal relationship with a program officer, or because you’ve been funded by someone that they know in their network. And as much as a lot of these orgs pay lip service to being really research-backed and objective about who they fund, that’s not usually how it actually happens in the real world.

So I don’t think these things are necessarily exclusive, right? I do agree to your point around you shouldn’t just expect to get money just because your mission matters. There is a healthy amount of competition. It’s not a zero sum game either. So I don’t think this means that every nonprofit who has a worthwhile mission is just deserving of all the foundation money in the world, and at the same time, I do think some of these structures are inherently not as effective as they could or should be.

Jonathan Hicken [00:09:00]: Okay. Let’s separate the fact that philanthropy has to exist in society from the way that we as leaders and fundraisers are going after that money. ‘Cause I agree with you. At a moral level, how do we get to this place where this is the system that we have to operate in?

Eric Ressler [00:09:20]: Yes.

Jonathan Hicken [00:09:20]: Okay? Yes. Okay. Fine. Fair enough. All sorts of questions arise with that, right? Major shout out to Stubski for their work.

Eric Ressler [00:09:30]: Yeah.

Jonathan Hicken [00:09:30]: On a personal level, I’m like, yeah, fuck yeah. I hope more foundations operate the way they do. Mackenzie Scott. Right? Great. Love that. Fantastic. But for us as individuals who are seeking the money to expect that from every foundation out there right now, I think is a waste of time and frankly just a not very smart way of going about fundraising.

Eric Ressler [00:10:00]: Yeah. So I would agree that that’s not a pragmatic strategy, right? Is to hope that philanthropy is going to fix itself. And look, I mean, we had Rusty Stahl on the show recently who is trying to advocate for some new fundraising mechanisms to fund the people. Like any systems-level issue, there’s a need for the kind of people who see that system and say, “Fuck that,” and work to change the system. But that is long, hard, decades-long work usually.

Jonathan Hicken [00:10:20]: Sure is.

Eric Ressler [00:10:25]: And then there’s the pragmatic, “Well, we gotta get the important urgent work done within the broken system.” And so what I’m hearing from your point of view is less, “Oh, the philanthropic system is perfect. We should stop complaining.” And more, this is the way it is, so either your work should be changing that or your work should be figuring out how to operate within the constraints that exist. Is that generally your point?

Jonathan Hicken [00:10:45]: That’s exactly my point. There are people who are already funded by a foundation, right? And let’s say you’re going out for a renewal or for an extension of that support. By all means, go have that conversation with your program officer about restructuring the flow of the money. That is an opportunity where, yes, you can express to your funder that this isn’t quite working for us, but there’s already a partnership that exists. There’s already a relationship that exists, and that is meaningful feedback for that foundation to hear from their grantee about what’s working or what’s not.

Eric Ressler [00:11:25]: I think about this sometimes from my point of view as an agency owner. A common but broken approach for hiring an agency is to put out an RFP, right? “Hey, everybody, we have this project. We’re looking for submissions to a proposal.” It’s very similar to applying for a grant. We basically don’t do RFPs at Cosmic for a very pragmatic reason. And I believe that, and I’ve written about and spoken to people individually and publicly about, hey, just like pretty much every agency owner who’s ever been through an RFP process, hey, this actually isn’t the greatest way to hire people like us. There’s a better way to do this. And it is very similarly about partnership. I have similarly pragmatically decided we’re not gonna do that. We are gonna work with people who are certainly should be doing their research and talking to multiple agencies and seeing who’s the right fit, but who are approaching it from a peer-level partnership from the beginning and not a “Well, it has to be this many pages and this set type and you have to have these professional references and know we won’t meet with you before you submit.”

How are you supposed to do that and do good work, right? That’s similar to, I think, sometimes nonprofit leaders and fundraisers, maybe especially ones who are early in their career, think, okay, well, I’m just gonna write a bunch of grants with people I have no real connection or relationship to and I’m gonna mold our work to fit the requirements of the grant because that’s just how we have to get money, right? That’s not a good strategy. And I’m not saying — I mean, we work with organizations that are 90-plus percent grant funded, but that’s not how they do their grant work, right? There’s a much deeper relationship and networking-based approach to doing it. So it’s both at some level, but I’d be really curious to hear more about how you think about, okay, if you flip the script and say, “We’re not entitled to this money,” whether it’s from a major institutional philanthropy or a major donor or a community member who’s giving what to them is their best gift, but might not be a lot of money — I’d like to hear your thoughts around understanding the customer and thinking about it that way.

Jonathan Hicken [00:13:20]: So everybody’s got a motivation. Individual motivation, organizational motivation, whatever makes them tick. And I don’t think that we spend enough time in the sector deeply understanding what that is for our funders. I think we’re generally better at that with individual donors, right? Because it’s a person. And you can ask them, “Why do you care about this?” When you’re asking a program officer, well, they’re gonna give you the company line, right? So it’s a little less personal.

But when I think about my time in tech and for-profit, business-to-business — I ran a customer success team and so much of our time we spent as a team asking our customers and trying to deeply understand what success looked like to them at their own job. I’ve worked with Adam from HubSpot and I’m like, “Adam, what’s gonna make your boss think you’re doing a great job and what’s gonna get you a raise?” Down to that level of what makes Adam work well? And then of course, I wanna understand what HubSpot’s goals are too so we can demonstrate that our product is helping them achieve both individual-level and company-level success.

I think the same thing needs to happen with foundations. Understand deeply what this individual that you’re working with needs. Maybe that’s a program officer, maybe it’s the CEO, maybe it’s somebody in between. Understand deeply what they care about, and then also at that organizational level. And it’s more than just their three goals that they’re stating on their website, right? It’s deeply understanding what they’re tracking, what success looks like, what are they trying to improve at. That level, I think, is really important so that when you put your proposal forward, you are addressing things that is speaking to a human and speaking to a team of people who are trying to get something done.

Eric Ressler [00:15:30]: Hey, friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Eric Ressler [00:16:15]: I think about that when we’re exploring client partnerships at Cosmic, and sometimes people have a really clear answer about that for the organization and personally, but I would say in more cases than not, that requires facilitation. It requires two skills that I’ve been really trying to lean into and acknowledge that I’ve developed over my career, which are deep listening and relentless curiosity. To me, to be a good designer, you have to be really good at both those things, to be a good strategic person doing this work in a meaningful way, those skills are gonna translate to almost any position in a good way, I think. On the flip side, I do think there is some reasonable criticism for some of these organizations that articulate they have a focus area or a mission, articulate they have standards and details about who they will and will not fund and all those things, but they’re loosely held.

I’m just gonna go ahead and put it out there. Chan Zuckerberg Initiative had some pretty strong opinions about who they were gonna fund and what they stood for, and they were really quick to let go of those as soon as Trump was elected again. I don’t have any problem with individual people at that organization who are doing their best work in philanthropy and wanting to do good and came in in earlier days where maybe that was a little bit more true, but these stated motivations and alignments are not always as clear or as real as they are stated. And so then funder priorities just change on a whim at times. And hey, that’s just the way the world works at some level, right? So again, back to the entitlements — you gotta be pragmatic about, I’ve seen over and over again clients who have multi-year relationships with funders, sometimes seven years long, and all of a sudden, oh, our priorities changed, best of luck to you.

Jonathan Hicken [00:18:00]: Bye.

Eric Ressler [00:18:00]: And it’s like, wait, that was a third of our operating budget, and you gave us three weeks’ notice, right?

Jonathan Hicken [00:18:10]: Yeah, but that can happen with an individual donor too, right? That’s not unique to a foundation. That happens — you need to build a business that can withstand those changes. That’s part of the job, I think.

Eric Ressler [00:18:20]: 100%.

Jonathan Hicken [00:18:25]: And someone like Chan Zuckerberg — they should be held to account for their priorities changing. I don’t waste my time with that, right? And that’s — I’m looking for organizational partners who do have a clear sense of self. And do know where they’re headed, and those things could change, and I need to be ready for that. But that’s on me to deeply understand the partner I’m looking for.

Eric Ressler [00:18:50]: Yes. I mean, I agree. And I think this is why I started by saying this is thorny. ‘Cause I think it is. Because I do agree that both can be true. As fundraisers, as leaders at organizations doing this work, we need to be doing the things that you’re talking about. We need to be really understanding motivations and trying to attract right-fit partners for our work who are doing this work. There are funders out there who, institutional funders and philanthropies, even if the money came in in less than ideal ways at the beginning, have turned that money into incredible impact. So I don’t want to come off as being anti-philanthropy, anti-foundation, but the longer I’ve been doing this work, the more I do question — a lot of these structures are bullshit. And I’ve been seeing more and more of that, interviewing some really awesome people even on our show and meeting them through the networks and also just seeing some of the frankly shitty downstream effects from some of these funders who, let’s remember, have tax benefits to being set up this way, have hoarded massive amounts of wealth, have invested that largely in things that are not necessarily good for the world and maybe even directly at odds with their stated mission. So they’re in this position of privilege and power, and so we should hold them to a very high standard.

Jonathan Hicken [00:20:00]: Yeah. Whose job is that?

Eric Ressler [00:20:00]: Whose job in the world is that?

Jonathan Hicken [00:20:00]: I mean—

Eric Ressler [00:20:05]: I think it’s — is society an acceptable answer? I think it’s—

Jonathan Hicken [00:20:10]: Designing Tomorrow, Eric and Jonathan—

Eric Ressler [00:20:10]: Well, here’s why I think I’m sticking up a little bit for your LinkedIn example. Shouldn’t it be all of our jobs? If we care about this work, if we care about this sector being the best version of itself that it can be, which I know you do and I know we both do, we have to be holding all of this at the same time at some level.

And look, you as executive director at the Seymour Center, you’ve got mouths to feed, you’ve got impact to make here locally. How much of your time should you spend thinking about this? Probably very little. But there’s a counterpoint to be made there too that’s like, these systems persist because no one says, “Hey, this sucks. Let’s do it a different way.” So I think there’s a lot to chew on here. And this is why I come back to — I think both can be true. I think you can be pragmatic. I think you can continue to say, “Hey, foundational institutional funding isn’t a fit for us for these reasons. This system works for us. We’re gonna double down on that.” And I know when you are talking to local community members and partners who are giving to you, you’re doing the same thing, right?

But yeah, whose job is it to fix philanthropy? That’s a big one, man.

Jonathan Hicken [00:21:20]: Yeah, I don’t know. Maybe as we’re talking, my little act of resistance is just bowing out of it, right? Of I’m not gonna play this game. I’m gonna look for people who wanna do good work together and if it works out, we’re gonna do it. And if not, that’s okay too. Maybe that’s my little contribution, right, is I’m just not applying.

Eric Ressler [00:21:40]: Yeah. Well, and I think that there’s no one way of doing this work. That’s something I’ve definitely learned.

Jonathan Hicken [00:21:45]: For sure.

Eric Ressler [00:21:45]: Even, and this comes down to what kind of org are you? Because you are a place-based organization, you have the ability to earn income. Not all issue areas have that ability, right? So some orgs really need that institutional funding because there isn’t a market-based approach. It’s really hard to raise from individual giving. It’s the kind of work that’s important but not sexy. Someone’s gotta fund that stuff if we think it’s real. So I think that my general take on this is that if we’re going to have institutional philanthropy that is not government, or that is government money, we should be consistently trying to do it better. To me, that seems obvious. Does that mean we need to be entitled about, oh, my mission’s important, so I deserve money? No, I don’t think those two things are the same.

Jonathan Hicken [00:22:35]: I think we just need to be really clear then when we are expressing our feelings about the system. Especially if we are a practitioner in the social impact space. To be really clear about when you’re talking about system change and when you’re talking about real grant-seeking work, because I can see if you’re commenting on systems change, fantastic. Let it rip. If you’re talking about actually going after money, the entitlement tone I think is hurting all of us. Do better work to better understand your funders.

Eric Ressler [00:23:15]: I think it can be, not always, but can be an excuse for an org that is not fundable. There are, let’s just be real, a pretty big percentage of social impact organizations and nonprofits that aren’t viable, just like there’s a number of businesses and startups that aren’t viable. The world is brutal.

Jonathan Hicken [00:23:35]: That’s how it works.

Eric Ressler [00:23:40]: And so I think that challenge, that competition, if you wanna use that word, there’s a certain amount of it that’s healthy. And I don’t think that means we should just accept the way this has been done traditionally, because I think there are emerging ways that are not just don’t just feel better and sound better, but actually just work better, right? When there are these orgs and these funders who have said, “Hey, you’re right, this sucks. How else might we do this work in a meaningful way, not just because it’s progressive, but because it’s actually more effective at the end of the day in terms of creating the kind of impact we wanna make, and how can we build social impact organizations that are not constrained by resources, but can sit there and imagine and do bigger work and not always be stuck in scarcity or reactivity mode.” We’re talking about the hardest problems in the world here. We have to think big about it. So I don’t know. I could keep going on the nuance of this. And I don’t have good answers for all of it either. It’s something I think about a lot and every time I feel like I have a really solid take on it, there’s some counterpoint that I’m like, “Ugh, that’s also true.”

Jonathan Hicken [00:24:45]: Yeah. I mean, this is one of those where I really wanna hear from listeners on the way you’re thinking about this and the relationship with your funders, because I see the argument for both. This episode topic came out of a place of frustration for me, where I was like, “Come on.” So it’s actually a little cathartic to talk this out with you, right? To be like, okay, yeah, actually this is — that particular post came from a real place, right? It wasn’t just someone whining.

Eric Ressler [00:25:10]: Right, right. And what I’ll say is your perspective on this is relevant regardless, right? Because approaching it that way is naturally going to lead to finding better, more aligned, more sophisticated, more progressive funders who are going to give you better support and gifts and partnerships.

Jonathan Hicken [00:25:30]: Yeah, I think so.

Eric Ressler [00:25:35]: So we don’t need to choose. And so I think it’s just, be clear about what is your place in this world and what feels right? Hey, if you wanna speak up and do it, do it. And if Jonathan thinks you’re a little entitled, who gives a shit, right? And I do think, to be clear though, there is a way to do that that’s constructive, and then there’s a way to do it that’s performative.

Jonathan Hicken [00:25:55]: Yeah, yeah.

Eric Ressler [00:25:55]: And so maybe the person you saw was a little bit more performative and felt a little bit more entitled in a way that was just like, oh, I need attention, or maybe they’re just venting. Who knows, right? A thorny one. One of our thorniest ones yet.

Jonathan Hicken [00:26:10]: In fact, I think this might be the biggest disagreement we’ve had on the show yet, so that’s good. All right. It’s good.

Eric Ressler [00:26:15]: Let’s keep going.

Jonathan Hicken [00:26:15]: All right. Well, this is a good one, Eric. Thank you so much.

Eric Ressler [00:26:15]: All right. Thanks, Jonathan. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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The nonprofit sector has a marketing philosophy problem. Somewhere along the way, we adopted a playbook built almost entirely around conversion, direct response, performance marketing. Get the click, get the gift, optimize the funnel, rinse and repeat. And look, that stuff matters, but it’s also incomplete because all of that activation depends on something most organizations never intentionally build: A brand that people actually know, remember, and feel something about.

You can’t convert someone who’s never heard of you. You can’t retain a donor who has no emotional connection to your work. And right now, the sector is raising roughly the same amount of money from fewer and fewer people every year. That’s what happens when everyone is fighting over the bottom of the funnel and no one is investing in the top. The missing piece isn’t a better campaign or a sharper donation page.

It’s brand. And not brand as in a new logo or colors.

Brand as in a deliberate long-term investment in making people feel something about your organization before you ever ask them for a dollar. That requires a willingness to make bets that are hard to measure and may take years to pay off. It requires playing the long game — and almost nobody in our sector is doing it. Except for charity:water. They’ve become one of the most recognized nonprofit brands in the world and it’s not by accident. Over the past few years, they’ve been quietly re-imagining how they invest in brand from TV campaigns designed to surprise rather than solicit to a 7,000 square foot immersive experience space in Tennessee. They’re making big bold bets and they’re working. To understand what that looks like from the inside, I wanted to talk with Brady Josephson. Brady is the head of growth and innovation at charity:water. Before that, he led their team through this multi-year shift from performance first marketing to serious brand investment.

He spent most of his career in the direct response and performance marketing trenches. So when he says the sector needs to rethink its relationship with brand, he’s not just a designer selling you in aesthetics. He’s a data guy who followed the data and he came to a completely different conclusion. I’m Eric Ressler and this is Designing Tomorrow, and now my conversation with Brady Josephson.

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Episode Highlights:

[00:03:00] How charity:water unknowingly burned through its brand equity

[00:05:30] What “investing in brand” actually means beyond logos and colors

[00:07:00] Why brand marketing takes 3–6 months to show ROI — and why that scares people

[00:11:00] Self-determination theory and why trust is really about competence

[00:14:00] The charity:water origin story and building for skeptics

[00:18:00] Why brand strategy looks different for small local orgs vs. large international ones

[00:22:00] You can tell the same story far more times than you think

[00:25:00] Inside charity:water’s 7,000 sq ft immersive experience space

[00:30:00] TV, attention, and why you need 2.5 seconds to form a memory

[00:39:00] What it actually takes to get organizational buy-in for brand investment

[00:44:00] Pick one growth engine and stop trying to do everything

[00:48:00] Brand vs. individuals: why charity:water was slow to adapt — and what they’re doing now

Notable Quotes:

[00:04:00]: “There’s something that we can’t see further up, carving the pathway for us that has now gone dry.” Brady Josephson

[00:15:10]: “Every nonprofit consultant would be like, ‘Don’t worry about them. They don’t give. Focus on these people.’ But that’s the exact type of thinking that creates where we are in this space, where we are raising the same amount of money from fewer people every single year.” Brady Josephson

[00:09:30]: “They don’t have a very clearly defined impact story. Maybe there are fundamental issues with the brand. We need to all be better about understanding human psychology if we want to reach people in a more deep and emotionally driven way.” Eric Ressler

[00:44:15]: “What you say no to or what you do less of is the game. That is strategy.” Brady Josephson

[00:24:00]: “You acknowledge some of the footage is old, some of the facts are out of date, and yet you’re putting millions of dollars of ad spend behind that piece.” Eric Ressler

[00:39:50]: “I did the work, did the research, came to the conclusion, vetted it to the point I was like, ‘I’m fully committed to this. I’ll put my job on the line for this thing.’” Brady Josephson

Resources & Links:

• charity:water — Brady Josephson’s organization, known for innovative brand-building in the nonprofit space

• The Factory at Franklin — Chelsea Market-style venue in Franklin, Tennessee, home to charity:water’s 7,000 sq ft immersive experience

• Lenny’s Newsletter / Lenny’s Podcast — Former Airbnb growth lead Lenny Rachitsky’s newsletter and podcast, home to the “race car” growth framework Brady references

• SSIR article on fundraising diversification — Article on the trap of fundraising diversification

• Bank of America Philanthropy Study — Referenced in context of giving trends showing fewer donors giving more

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:02:15]: Brady Josephson, thank you so much for joining me today.

Brady Josephson [00:02:15]: Thanks for having me, Eric.

Eric Ressler [00:02:20]: So I’m really excited today to dig into all things brand and brand marketing and social impact and the intersection of those things. We are right in my sweet spot and the sense that I get from you is we’re right in your sweet spot too. So I would love today to just break down, and if you wouldn’t mind, let’s imagine together a completely different social impact sector where brand marketing and brand building is core to how nonprofit organizations communicate and what that looks like. And I think I’d like to tee us up by giving you an opportunity to talk about what you’re in the middle of right now as a leader at charity:water and how you’re experimenting with really completely re-imagining how you guys are making investments in brand and in paid media and in communications in general, and let that tee us up for the rest of the conversation.

Brady Josephson [00:03:10]: Yeah, that’s a big conversation. I’ll do my best. I think one thing to acknowledge right off the hop is I come to the brand side of the brand marketing conversation pretty honestly and through the back door. So much of my career was on more of the bottom funnel, transactional, performance marketing, direct response. Like a lot of people in the nonprofit space. If you read articles and go to conferences, the vast majority of things that get taught and are learned, whether it’s at grad school or conferences or podcasts, it’s often pretty transactional, pretty bottom funnel. And so I think it’s a bit of a journey that a lot of direct response people go on for a bit is like, “Oh yeah, direct response is the best provable ROI.” And then at some point you’re like, “Oh gosh, this isn’t working like it used to. What’s the problem?” And then you figure out, ah, there’s something that we can’t see further up, carving the pathway for us that has now gone dry, which is exactly the story of charity:water.

Unbeknownst to charity:water, I think, was really investing in brand, in brand marketing for years and years and years. Very intentional about brand and design, but in terms of building a brand and brand marketing, I think it was a lot of just intuition from our founders and early folks. And so then when we shifted more to really growing the monthly giving program and focusing more on revenue optimization, we started pulling from all that brand equity that we had built up until one day it was like, we’ve pulled all the brand equity that we’ve earned up. And so how do we get this ship going in the right direction again? We need to actually invest more in the brand.

And so that’s really the journey that we’ve been on over the past two years or so is really plateauing in revenue, what’s going on, ending up and saying, “I think we have a brand problem, not so much in logo and positioning, but just reach, awareness, engagement, which is causing a lot of revenue problems for us.” And so that’s the journey that we’ve been on and the journey that I’m on more as a marketer as well.

Eric Ressler [00:05:10]: There’s so much to dig into right away. And I want to try to break down some of these terms to listeners, especially who aren’t as in the weeds on this stuff and make it more accessible. So bear with me while I do that a little bit.

Brady Josephson [00:05:25]: All right.

Eric Ressler [00:05:25]: When you talk about investing in brand, what does that actually mean? Because I think a lot of people hear that and they’re like, “Oh, so we’re going to redo our logo and our colors now.” So what do we mean when we talk about brand marketing and brand building? And I’m happy to riff on it from my perspective, but I’d love for you to start.

Brady Josephson [00:05:40]: Yeah. Again, it’s hard. And you could probably ask six different people and they would answer it slightly differently. When I say invest in brand, I’m very specifically talking about how we use paid dollars and resources to make the brand more known. And now you don’t want to do that unless you have a better sense of who we’re trying to reach, what the targeting looks like, what the positioning is, what the logo should look like. Those are underlying things that you would have in place before you really spend a lot of resources and time and money to make sure people know who you are. Otherwise, what’s the point? If you’re not creating the emotional connection that you want, there is not as big of a point for brand marketing.

So it’s both the lowest thing of how do we reach people with the brand, but it’s also the highest thing of how do we leverage the brand to create emotional connection with people and hopefully invite them in some way to join us on our mission and our journey.

Eric Ressler [00:06:30]: Great. So I agree with that. And I would say that one of the things that you alluded to in your first response is this tension between brand marketing and brand building, which I look at really as longer game plays. They may have some short term results, but really we’re looking at playing a long game. Whereas direct response, performance marketing, very targeted campaigns, conversion focused campaigns — we’re talking about measuring things in weeks, months, sometimes even days. Whereas brand marketing, and I think some of the data that you guys have collected even on your own shows that we’re talking more at least in three to six months before we can really start to see a return on investment.

And I’ll just put a pin in this because I want to come back to it in more detail. Measurement of brand investment is becoming harder and has always been harder to a degree. And I think that’s a big reason why people traditionally underinvest in brand marketing.

Brady Josephson [00:07:25]: Yeah, that’s definitely it. And I think a lot of it does start with the measurement side. And when you actually go into a lot of the research around how do you measure brand, it’s often quantified in things like business effects, share of market, are you actually growing or sales improving? They’re pretty top level. And that’s at one level so opaque, but it’s also like, what do we exist to do? We do not exist to increase retention by two percentage points or increase our donation page conversion by three percentage points. Those are little pieces of the whole. We exist to grow our causes to help more people, in our case, get the clean water that they deserve. That’s all that matters.

And so at one level, we get so wrapped around the axle and myopic around what was the ROI on that email and this campaign and just saying, are we moving the organization forward and achieving the things that we need to do or not? And that’s really what is the bellwether of the brand. If you have all the awareness in the world and you can’t execute your mission, who cares? So that’s fundamentally the thing that you start measuring against. And once you start really understanding brand measurement, it is really the most important thing that you can get into. Now you can get into more detailed specific parts of brand measurement that we can talk to, but at the highest level, it’s like, are we helping drive the business forward or not?

Eric Ressler [00:08:40]: Totally agree. And what I would also add to that from the way that we think about it is if you get so myopic in these conversion rate optimizations to the stat that you threw out, improving conversion rate in the donation form by 2%, that can make a big difference, especially if you have hundreds of thousands of monthly donors. But what I often see in my work, and we tend to work with growth stage nonprofit organizations, social impact organizations, is that we’ve been trained to focus on ROI, on return on investment, return on advertising spend, these things that we see as best practice.

But what I consistently see with the clients that come to us is that they are missing the bigger picture fundamentals of good brand marketing and hyper focusing on these things almost like they’re trying to run before they’re even walking in a lot of cases, where they don’t have a very clearly defined impact story. Maybe there are fundamental issues with the brand that might be the name, it might be the logo, it might be the design system, it might be their ability to just create any kind of emotional connection. I think there’s a lot of academic speak and jargon being used to describe the impact work coming from research and that stuff is important, of course, but we’re losing something.

We need to all be better about understanding human psychology if we want to reach people in a more deep and emotionally driven way and actually move our missions forward. And so I would rather take all of that time spent, or let’s say 75% of the time spent on these micro improvements, these conversion focused improvements, and put that towards understanding how people actually tick in this space, what actually gets people lit up.

And I want to touch a little bit on one of those things I think is becoming increasingly important, which is trust, which is a little bit of a buzzword right now. But if people don’t know your organization and people don’t trust your organization, if there’s not an emotional connection, if there’s not credibility built, none of those conversions are going to matter because you are reaching only a fraction of the people that you have the potential to reach. So I’m wondering if you might be able to riff on how you all think about building that trust, building relationships with the people that you need to reach and reaching new audiences at charity:water.

Brady Josephson [00:10:55]: Yeah, definitely. It’s critical for all transactions. And let’s try two different frameworks. One, so talking about understanding humans, I’m a pretty simple guy and one of the best frameworks for understanding humans, self-determination theory, which basically says at the root of all things that we do, we want to be competent, autonomous, and connected to others. And I think that’s a pretty good way to think about it. And so for me, trust is a subset of competence. When people give, they want to feel like, “I’m a smart person making a good decision.”

So I think too often when we hear trust, we immediately go to overhead spending or impact reports or something like that. And that’s a function of it. We have that. We have a hundred percent model, which is really built on the idea that so many people when it was invented did not trust charities. And so we just said, “We’re going to do it differently to take that out of the equation altogether and just say, do you want to give or not?”

So that is a component of it, but a bigger component is, are you helping people feel competent? And you can do that in different ways through really great storytelling where people have an understanding of the work that you do, through a really tangible offer of $40 does this. That’s a way for people to feel confident. There’s so many different ways to go at building trust, but I prefer to focus more on competence because I feel like it’s a little bit bigger and it’s a little bit more of the driver that I think humans are really looking for when they’re scratching at trust. It’s really, “I want to make sure I’m making a good decision and there’s other ways that we can do it.”

Eric Ressler [00:12:20]: Yeah, I actually really love that reframe. I’ve never really thought about it quite that way. The way that I’ve thought about it before is that people want to support organizations that they feel like are going to make an impact, which sounds very obvious, right? But when you start to really break that down, what is it that makes people feel that? And it is a mix of things, I think, in my opinion. Yes, impact storytelling and stats and numbers and seals and transparency and those things are all adding to it.

But I think more than anything, it’s actions in the real world. And this is why I believe communications, and we can even stretch this more to brand building, is so important, because you have to show people that when they are investing in your organization, it is actually leading to actions in the real world, not just an annual impact report. And I believe this is something that charity:water has been exceptional at compared to the standard.

And we can talk about the 100% model. We could talk about the transparency and the tracking opportunities that you provide donors and supporters, but I think you guys have done an exceptional job at making someone who’s considering becoming a supporter feel like it’s going to be a good choice, that it’s going to actually make a difference, going to lead to real world impact, that it’s not just this, “I’m supporting because it feels good.” And there’s nothing wrong with supporting because it feels good. And a lot of people do give from that emotional standpoint. But I think the more that you can make, to use your framework, supporters feel like it’s a good logical decision — people do give from emotion, but there is a logical barrier that has to be overcome for that giving to actually take place and people actually put their credit card in.

Brady Josephson [00:14:00]: Yeah, for sure. And a lot of the charity:water story for people who aren’t familiar — it was a club promoter in New York who was like, “What is my life about?” He’s 31 saying, “This got to be more to life.” Quit cold turkey, went on a service trip on a mercy ship, started taking photographs and walked out into rural Liberia and came in contact with just horrible water and said, “You know why everyone’s getting sick? It’s because they’re drinking this water.”

Came back and turned his life around and said, “I’m going to give my life to this cause.” And so much of the DNA of charity:water is built for skeptics, to be honest, right? He went back and threw a birthday party with all his not typically philanthropic friends and said, “I’ll prove this to you.” And that’s what we have today. We track a metric of how many people give to charity:water and it’s their first time ever giving to a nonprofit because we feel like that’s part of our role in the charitable ecosystem is to help try and grow the charitable pie, not just take a bigger slice of it.

And two, that’s what we try to hold ourselves to. The vision originally was to reinvent charity. You can’t say you’re reinventing charity by just raising more money from the same people. So that’s always been in the DNA. And that’s where a lot of the model, the proof, the trust is saying, we are trying to convert the skeptics. And that is on paper, low ROI proposition. Every nonprofit consultant would be like, “Oh, don’t worry about them. They don’t give. Focus on these people.” But that’s the exact type of thinking that creates where we are in this space, where we are raising the same amount of money from fewer people every single year because we all follow that methodology. And it’s not one focused on growth.

And so I feel really lucky to work at an organization that has so much of that in their DNA because that mindset and view is often by far the hardest thing to get in organizations. And I realize that.

Eric Ressler [00:15:40]: Yeah. And I think that’s consistent with some of the recent giving trend data. We just did an episode with the Bank of America philanthropy study. And one of the things that came out from that is that overall, fewer people are giving. However, the people who are giving are giving more. And that’s positive in some ways. And a lot of the takeaways from that episode is there’s some good things to be feeling good about in terms of overall giving is up. Some of the data that just came out around Giving Tuesday was pretty positive as well.

But the near enemy of that that I’m a little bit worried about is that fewer people are giving. And not only are fewer people giving, but this is just, in my opinion, a reflection of growing income inequality, especially in America. And we want charity to be a big tent game, in my opinion. I don’t think it should be something that is reliant on a smaller and smaller subset of wealthier and wealthier people to prop up. And there’s been all kinds of discussions around some of those elements of philanthropy.

So how can we make philanthropy every person’s game? Where it’s not this exclusive club where you’re a philanthropist and you come to expensive galas, but something that everyone can participate in in a more democratic way. And I think that charity:water has been a good example of what that style of philanthropy looks like.

And what I’d like to go next actually is to talk about how that might translate to orgs where the story isn’t quite as simple or intuitive as charity:water. I think when you’re first introduced to charity:water, it makes intrinsic sense. Oh, people need clean drinking water. I give money to charity:water. They give clean drinking water to people who need it. At face value, a very simple story. The ROI for a potential retail donor is really straightforward. What about orgs who are doing more upstream work, where they’re doing systems change, where they’re doing advocacy work, where they’re doing policy work, where they’re not doing as much boots on the ground work? Do you feel like some of the approaches that you’re taking specifically around brand building and building out more awareness and top of funnel is still worth exploring? Or what would you do if you were to join an organization like that and be in charge of growth?

Brady Josephson [00:17:55]: Yeah, I think that’s a great point. Oftentimes we get in conversations and we talk about the nonprofit space, or especially when maybe you go to conferences and are talking about the nonprofit space with folks who maybe don’t spend as much time in it. It’s a huge space, right? It’s like 13% of the workforce. It’s bigger than the manufacturing industry. It’s huge, and yet we often talk about it as it’s singular. And so I think it is worth pointing out. There’s some splits that we can talk about, like large and small, international and local. So even just think about a two by two grid. We’re large international. That’s very different than small local.

So some core concepts, marketing is marketing, fundraising is fundraising, great. But some of the things carry less value. And I would say if you are local and small, yeah, building up top of funnel and brand is probably not as impactful, but it doesn’t mean you don’t need people to know who you are or resonate with what you do or have an offer. You absolutely do. It probably just means that strategy will diminish quicker than say a large international organization.

And so again, if you come back to people need to know and trust and feel competent, that’s really what the brand exists to do. You can’t feel competent about something you’ve never heard of before. Or if the story is so confusing, you can’t quickly understand what it is. So we are very fortunate. Clean water, we’re not faith-based, we’re not political, we are very accessible and that has been part of the recipe for success. So I fully acknowledge that.

I do think we overcomplicate things in the nonprofit space as well, right? You get a lot of programs people, a lot of academics, a lot of people who get into it because they want to serve the people, but how they think about the work is often very different than the average person who will fund the work. And that is one of the marketer’s and fundraiser’s biggest blind spot — you know too much and you lack the ability to talk about it in ways that work if you don’t have that information.

And so that’s where agencies and outsiders can be super helpful. Actually, if you trust them, that’s where research can be super helpful and testing can be incredibly helpful because almost for sure how you think and talk about your organization is wrong, just left to your own devices. Maybe major donors, maybe major funders, but if we’re talking about mass consumer, which is where I live, your natural instincts are probably wrong. It’s just the way it is, honestly.

Eric Ressler [00:20:20]: That rings really true. And I think one of the things we’re often working with clients on is there’s this intuition, especially if you’re more academic in your background and more research oriented, really true category experts in the space, which a lot of nonprofit organizations and leaders are — we’re talking about some of the most complex issues in the world. They should be the world’s leading experts at this work, but they have a sense that they must tell the entire story all at once.

That’s the big mistake that I see more than often. It’s like, oh, but we’re not talking about this program or this program or this program, or that’s not quite true where you’re forgetting this one nuanced thing. And it’s like, great. So when you go to a movie, do they just regurgitate the entire plot all at once or is there an actual narrative? Is there tension built? Is there an introduction? Is there an establishing shot?

So I think a lot of what I see our job as we are working with social impact organizations who are doing oftentimes super complex, super deep work, how do we translate that in a way that is accessible without at the same time inadvertently dumbing it down? And there’s no silver bullet answer to that. That is the hard creative work and that is the strategy work that needs to be done.

But one of the things, and for listeners who are trying to figure that out right now and also figure out how does that fit into this idea of brand marketing, I would encourage you to realize that you don’t need to tell the whole story all at once, that you can drip that out. What is the simplest, most memorable, most intuitive way to introduce someone to your story and then build more depth and breadth over time in relationship. We talk a lot about donor nurturement and nurturing donors, engaging donors. One way to do that is to tell a deeper and deeper story over time instead of trying to do it all at once.

Brady Josephson [00:22:15]: Yeah, for sure. Again, and this is where data can help too. If you think about web, probably 85% of people who visit our website have never visited before. And so even if you’re telling a story, keep it simple, but also you can tell the same story pretty much way more than you think, just like you can reuse content.

So when we launched our monthly giving program called The Spring, there was a video called The Spring Film, and it’s an 18, 19 and a half minute mini documentary. And we’ve been running it and sharing it and putting millions of dollars of paid spend behind it for seven years. And people see it for the first time and they’re amazed. It’s a little old, some of the footage, some of the facts are out of date, but what we’re trying to accomplish, it absolutely achieves. And there’s so many people who still haven’t seen it, even though over a hundred million people have. And even if they have, they’re like, “Oh my gosh, I forgot I watched that a few years. This is amazing.”

And so again, I think the parallels to me are just like, we are so in our own shoes without using some data or research or trying to get outside and say, “Yeah, but they don’t know who we are.” Or even if they do, you’re probably not as big of a role in their lives as you think they are as well. So some repetition or some revisiting is totally fine. And I just think we get so wrapped up in our own stuff, it gets harder to do that. And in some ways it’s actually harder when you’re smaller because you know everyone or you feel like you know everyone. When you’re big and you just have a lot of numbers, “I can’t possibly know everyone,” it does get a little easier in some ways. But that mindset I think is really helpful. And that’s where I think coming from more of the data side actually helps in some ways on the brand side — you just think about data and it really helps unlock some of that.

Eric Ressler [00:23:55]: Yeah. I want to reiterate one thing you said that I think is actually quite fascinating, which is you acknowledge some of the footage is old, some of the facts are out of date, and yet you’re putting millions of dollars of ad spend behind that piece. I’ve worked with so many organizations where those two things would be an absolute deal breaker. And this is, I think, where we sometimes lose sight of the bigger picture — we can’t get so caught up in these minute details and lose sight of the fact that you guys put a lot of time, energy and effort in producing that piece.

I remember when it came out, it stuck with me because it felt different, and you’re willing to continue to promote it and to distribute it, which is another thing that I think a lot of folks heavily under index on. They spend all this time and energy putting creative things together, but have no distribution strategy whatsoever or no paid media spend behind it.

So I think that’s a good segue actually. I’d love if you wouldn’t mind sharing some specific stories and examples about what you all are doing right now and taking some bigger swings around investing in brand. And I’d love if you wouldn’t mind starting with the 7,000 square foot retail space that you guys have opened and what was the idea behind that? How’d that come to be and what are some of the early results from that so far?

Brady Josephson [00:25:10]: Yeah, that’s definitely the biggest swing we’ve taken since I’ve been here. It’s a pretty big one. So what it is, it’s 7,000 square feet. It’s in Franklin, Tennessee. It’s in a cool Chelsea Market style place called The Factory. And we’re up on the second floor and we have hour long reservation only free tours where people are introduced to charity:water and the water crisis and watch a video.

They go for a walk for water in a really hot room lined with LEDs and you’re on a treadmill and you carry a jug of water while you walk behind a girl in Uganda to try and get a sense of what it would be like in Uganda. You learn more about diseases, bacteria and water, you learn about the solutions that we have. We have a VR film that we shot where you see a community get clean water for the first time through the eyes of a girl in that community, which is the pinnacle absolute experience. Everyone rates it the number one. And part of it’s the journey that we create, but part of it too is just, again, keep it simple. If you watch a community go from not having water to having water, you’re forever changed by seeing that. So that’s all we’re trying to do is just let you see it.

And then there’s a real pump that we built that you can pump in celebration. So it’s really tactile, really experiential, really family friendly. Costs a lot of money and took two years to build and get off the ground. And we’re about nine months post-launch, one year after soft launch.

The idea came about because we would have so much success and invest so much in our galas in the past. And so you’d put all this energy into these amazing experiences at an event and then you’d have 200, maybe a thousand people see this, they’re transformed, and then onto the next thing. No one else gets to experience it or see it. And so the idea, and this wasn’t my idea, it was long before — it’s when we were still based in New York — was saying, “What if we just took the best that we’ve produced and made it accessible for more people to come and experience it because this stuff is amazing. And we’ve already spent so much time, energy and money to develop it.”

And so we started looking at shops or pop-up shops, and this was New York in 2019, 2020, and then it was not a good time to invest in retail. And so when we got on the other side, we went remote only. Our founder found his way down to Nashville and Franklin, Tennessee, and we hit this plateau. Then it was like, well, what if we revived this idea but gave it a different spin. So instead of in New York or at a pop-up, what if we put it in this up and coming place where we could get a really great deal and it’s close to the founder and it could be this storytelling asset as well as something that the public can really use.

And so it was really risky at one level, but also we had a decade of knowing that when we put our story and experience in front of people, it works. So the risk was more in, can we get enough people through this space and will it generate enough revenue? It wasn’t, would we provide something that’s compelling? And again, I think that’s a luxury that we have at charity:water where that’s not really what we question. We know that we have that in us. It’s more like, can we make this work from a business standpoint?

And so yeah, we’re about nine months in. We’ve had over 7,000 people visit. We’ve raised about two and a half million dollars in projected revenue. The net promoter score’s about 93%. People are coming back and bringing their families. It’s truly amazing. You got to come check it out. It’s quite special.

Eric Ressler [00:29:20]: I’d love if you could share some of the other ways that you guys have been reallocating your spend from bottom of funnel to top of funnel and some of the early results that you’ve seen from that too.

Brady Josephson [00:29:30]: Yeah. So I think one of the things is we started investing a lot in TV. And so again, when we went on this deep dive of how do we invest in brand in a meaningful way and what’s out there from a research perspective, you quickly end up in a place where you’re saying we need to capture attention. You need about two and a half seconds of attention to form a memory and memory is linked to building brand or recall or something called mental availability, which is the academic term of when someone goes to think of you, will they? Essentially.

So you need attention and some channels are way better at delivering attention than others. So you can run display ads for days, but capturing someone’s attention is really difficult. They’re just going to glaze right over it. Where TV, whether you like it or not, especially non-skippable ads, they capture a lot more attention than almost any other medium. And so TV doesn’t make sense for some things, but when you’re trying to build brand or mental availability, you need that dedicated time.

So TV was one, but then you also need a different style of creative. We can’t just take a 19 and a half minute documentary or take some of the things that work really well in a fundraising campaign because those are made to activate people, not necessarily leave a memory. And some of the emotions that are linked to memory are things like surprise and happiness. And surprise is one that nonprofits typically don’t do very well at all. I think we’re getting better and better at happiness, but it’s pretty expected happiness. This person didn’t have something, thanks to you or thanks to this organization or a local partner, now they do and everything’s happy. It’s also pretty expected. So even the happiness that we provide, I think, is a little muted because we all tread a very similar storyline.

And so we shot some very different creative that would be more like brand spots that you would see. A car going through a car wash without water, a kid going on a slip and slide without water, someone at a diner who gets coffee without water. And we don’t actually talk a lot about the work we do in the water sanitation and hygiene space or our local partners or none of that’s there. It’s really solely built on how do we capture attention, leave an emotional connection tied to our brand, which is really what nerdy brand building on TV is really about. So we really tried to execute that strategy.

Eric Ressler [00:31:45]: And I think this is what you see consumer brands do all the time. And sometimes I talk to friends and the classic example of this is the Super Bowl ads. And everyone’s talking about what their favorite Super Bowl ad is, but there’s always someone in the room who’s like, “These ads are all stupid. None of them describe what the products are.” And there’s a very good reason for that, which is that they don’t exist to describe what the products are, what the benefits of the products are. They exist to create that recall and that memory. And surprise and curiosity also are two of the most important emotions to trigger to create memories and to create that recall.

And it is interesting to think about how might social impact organizations do that. The way that you approach some of those spots, and I’ve seen some of them, are very nontraditional for the space. I can’t really think of too many others quite like that. I would say probably the closest thing would be celebrity voiceover style ads that you’ve seen from some major international orgs that have been done by some of the major ad groups down in LA who have a for good arm or something.

And so I’d be curious to hear how that’s gone for you so far and how you think about how that fits into the overall flow of engaging someone and inviting someone into the charity:water world.

Brady Josephson [00:33:05]: Yeah. So I think one thing worth pointing out too is TV today is very different than TV five years ago and definitely TV 15 years ago. So to help measure this, we implemented something called marketing mix modeling and it tries to take a holistic view of what’s driving performance. So it’s not your CRM doing attribution, it’s not your platforms doing attribution. It is a data model looking at three plus years of all the data and trying to — then we trained it for six months to try to figure out what’s actually driving that.

So you think something shows up as a search donation, search doesn’t drive very much. Something drove the person to look for you. It could be seeing an ad, hearing someone speak, something’s driving it. And so what MMM is trying to do is figure out, yeah, but what’s the thing that drove the thing that got the thing?

And so we implemented that largely to help monitor TV. And what we found through that is TV was our second cheapest donor driving platform according to MMM. So they may have given through search, but TV is really what drove them. And that’s a bit of a game changer. And if you think about how you watch TV, you can watch TV, be like, “Huh, that’s cool.” Pull up your phone, Google really quick, scan the QR code. You can go to the website. And if the website’s good and simple and clear, you can go from never hearing about a brand, being like, “That’s pretty cool,” to buying something or taking an action faster and easier than ever before.

And so that’s the other one of the main arguments for investing in brand now is you can transact almost anywhere, but can you be remembered and will people hear about you? The value of brand is going up in the world. That’s the bet that we’re making. But I want to make that point on TV because often it’s like, “Ah, TV, it’ll take forever.” And maybe, but it’s more of a performance channel today than you might think, I think, especially if you do creative really well.

Eric Ressler [00:35:00]: No, that’s great. I want to actually go a little bit deeper on that because what I don’t want listeners to do is say, “Oh, Brady says TV is the future. We’re going to go spend a bunch of money on TV.” Because I think what you have to realize is, especially if you’re doing connected TV or YouTube is often synonymous with TV these days, you cannot just run your boring academic documentary on TV and say you’re doing brand marketing. I mean, I guess you could, but that would be a really bad idea.

And so I think especially if you’re talking about YouTube, but even to a degree just TV as a channel, people are typically watching TV to be entertained, right? Sometimes people are there to learn. I do actually a lot of learning on YouTube for my own personal reasons for music stuff. But it’s an entertainment modality. And so if your content isn’t entertaining, even if it’s edutainment, it’s a mix of education and entertainment, it’s probably not going to perform very well. So I’m curious how you guys thought about the creative element of that and making sure that the content was actually appropriate for the medium.

Brady Josephson [00:36:00]: Yeah. Again, I think that’s where a lot of the research is coming in handy is trying to figure out what are the emotions and then how do we evoke some of those emotions like surprise. And then we did some pretesting. So we did various degrees of pretesting to see, “Hey, is this resonating with people?” And you can do it as cheap as $800. There’s a tool called Listener that we use a lot. We just used it this week and you can recruit a panel pretty cheaply and get some feedback. And again, trying to get out of your own mind. I mean, that’s why we did it — our creative director was working on something and I said, “I like this, but I’m pretty biased because I really like those people. Let me try to get out and get some other data.” And sure enough, the folks that we paneled really preferred the other one. So I said, “All right, let’s try the other one.” So that helped guide us.

And then we had some more sophisticated testing in there as well to make sure that we were on the right track. And so it’s not just like, you don’t flip a switch and then just start pouring money into TV. You can test in little ways. Again, you can stand up TV or if you have YouTube, you can say, “Just show this on TV with some creative that you feel might work and just start getting your feet wet.” There’s some ways to do it.

And then we also — I spent maybe a year getting the alignment that this is a good thing for us to spend on. So even though charity:water has high risk tolerance and we get brand, it wasn’t just like, “Hey, I want to take half the budget and just spend it on things that are going to be super hard to measure.” It took a lot of time and that’s where a lot of the research came in. And then our founder intuitively getting it helped a ton, but it was a year and a half process to get us to the point where we were willing to start making those types of investments. And then we made smaller investments and then made bigger investments. So all in, it’s been a three-year process to get to this point where we feel like we’re aligned, we’ve got the creative, we’re investing at a high level and we’re confident in it. It didn’t just happen in a three-month window. It’s definitely a big commitment that we made.

Eric Ressler [00:38:05]: I think that’s actually a bigger theme I’d like to dig into just a little bit because I often do hear and see people online in the social impact space hold charity:water up as this benchmark, this aspiration around, “Well, this is how charity:water did it. We should do that too.” But what I don’t think a lot of people understand is how much time, energy, investment and expertise you all put behind the work. I think a lot of that is invisible and people want the results, but don’t understand what that actually looks like to get those results.

So I’m wondering if you might be able to, at least at a high level, just give people a sense of what does it take to run your communication and fundraising program at large at charity:water? What’s the general team size, level of investment at a high level even? How much iteration and growth and professional development are you doing? I want people to understand that this doesn’t happen magically. And I’d actually like, even if you wouldn’t mind talking about the ability for risk tolerance, because I feel like that is a non-negotiable for running a program like this.

Brady Josephson [00:39:10]: Yeah. I think that’s probably the best place to start, honestly. And I was having this conversation with someone and we were just saying, how do we create ways to shift the mindset of executive leaders and board members? Because absent that, it’s really hard to change. Someone could be listening being like, “I get it. They’re sold on brand, they’re sold on TV, but they have to get that person or those people or all the way up the chain because you can’t just make this type of investment over time without that type of alignment and buy-in.”

So one, I do think even at charity:water, you have to work hard for it. So you have to be really convicted and willing to put yourself out there. And it wasn’t just me, but it was definitely something that I did — I did the work, did the research, came to the conclusion, vetted it to the point I was like, “I’m fully committed to this. I’ll put my job on the line for this thing.” And so few times do I think people are actually willing to do that. And then it’s like, “Wow, nothing happened.” And it’s like, “Well, how willing were you to put yourself out there and do the work?”

So I think that’s important, but I do think risk tolerance at charity:water’s super high. We’ve had something in our culture from day one about trying things, testing things, wanting to be the first. There’s a concept called safe to try where there was a process where you’d get a gathering of cross-functional people and run this idea by them and you’d get a cumulative, yeah, that feels safe to try, to de-risk some things, but everyone’s starting point was yes.

So there’s these things baked into the culture to make it happen. And then our investment last year on the paid side was about $2.6 million, which is pretty big for international, but pretty small compared to some others, and especially TV. That was one of the learns actually — we can’t compete on TV with the other people that were competing on TV, so we need to still be smarter on the TV side.

Our marketing team’s way smaller than people think. When I started, we were rebuilding the marketing team. There was zero full-time marketing people when I started. Now we had a big creative team and they did a lot of the marketing work. So again, when you get into marketing, it’s like, oh, copywriter, are they creative? Are they marketing? Some fine lines, but our marketing team’s about five. Our creative team’s going through a transition. We’ve been as big as 12 and as small as two.

So it’s still a pretty lean team, but so much of our time and energy in the past has been really focused on marketing. And I think we have a marketing led founder or a marketing centric founder. When you think of Airbnb, they’re design led because their founder’s a designer. You think of Shopify, they’re engineering led, their founder’s an engineer. Our founders are creative and a marketer. So when he gets free time, he’s thinking about creative and marketing. And so I think that’s also really different as opposed to the programs person, the practitioner, the academic. Ours is a salesman, a marketer and a creative. So that makes its way through the org.

And again, it’s a really lucky spot to be in. But we’ve got a lot of constraints. We wish we had more time and money. We fail a lot too. Some people are surprised. Our email program is very small compared to what people think it is because we don’t focus a ton on it. We focus on some different levers. So yeah, you’d be surprised on some of the things that we have or don’t have maybe at charity:water too.

Eric Ressler [00:42:40]: Yeah. Thanks for sharing all that in a transparent way. And I think it’s all relative because sometimes we work with folks where they fought tooth and nail to get one full-time chief communications officer who’s supposed to do the job of 12 people somehow and also has no marketing budget to invest. So there’s folks at that level. And then of course, there’s obviously a whole spectrum of maturity from there.

I would like to just get your thoughts really quick around if you were starting from a smaller point of view, and let’s say you’re a $5 million a year org and you aren’t as staffed up. What are the bigger picture ways that you would think about making investments in brand, in fundraising, in some of the just general best practices for communications when you’re not quite at a level of sophistication that you’re even at at charity:water at this point? What do you feel like in your bones right now are the fundamental skills and where those are going and how those are changing right now? Because I do feel like this is all very fluid in this moment in culture.

Brady Josephson [00:43:50]: Yeah. No, that’s a great question. And I should mention too, my first job out of grad school, I was the only full-time employee. I know what it’s like to work in a small shop and wear all the hats. Before I answer the skill question, I think there’s a question on model. And I think this is where small and medium-sized nonprofits get really tripped up — they feel like we have to do all the things and you really don’t. You maybe have to do all the things at a small level, but you should not be doing all the things at the same level. What you say no to or what you do less of is the game. That is strategy. Saying, “Oh, we should do this, fine.” What we won’t do or what we’ll stop doing or what we’ll do less of is actually what real strategy is about.

And so there’s a great framework. There’s a podcast and a site called Lenny’s Newsletter, and he’s a former Airbnb growth guy, and he’s got a growth framework called a race car. And it really resonated with me because it basically boils down to — and this is a for-profit example — but there’s only four ways that you grow, that is your growth engine. And when you’re starting up or you’re small or medium, you only have one engine. You don’t have multiple engines. When you get to be really big, maybe you can develop a second engine. So you need to figure out what is the engine that is going to drive your growth, and then you orient everything around that.

That doesn’t happen in nonprofits. It feels like we got major gifts and grants and foundations and email and direct mail and monthly, and you cannot do all of it, especially if you’re really resource constrained. So some of that hard work is trying to figure out, like saying, we are going to be paid ads heavy and we’re going to focus on monthly giving. That’s how we are. That’s a tough road to go. It’s not the easiest one for all startups, but then you start going, “Here’s what we need then. We need money, we need content, we need data, we need digital.” So then who you need or who you hire is way easier to figure out, or what you need from the board.

If you can’t make that decision of what your revenue engine is or should be, then all these decisions get really hard. And so I think that’s the hard work that not just smaller, every org really has to do. And then you basically, again, have to double down and triple down on that growth engine and get better and better at it. And even diversify — I think we’ve overdone it on diversification. If you’re really good at one thing, keep doing it and finding other ways to improve within it. I think we’re often a little too quick to do big diversification like, “Oh, major donors are starting to dip. Let’s go to Corp.” Nope. That’s a totally different world. Get better at major donors, revamp major donors.

So I think that’s my own personal belief and I’ve really just resonated with that idea of growth engine and then what are all the things. And so then that leads to answering the skills question. So I don’t think you can really answer who do you need and what are the skills without knowing, well, what’s the strategy? What’s the engine?

Eric Ressler [00:46:40]: Yeah. Well, and there’s actually, and maybe you’re familiar with this — I’ll link to it in the show notes as we put the episode out. But there was a seminal article on SSIR about this exact issue, which is that there’s this trap of diversification around fundraising. And the data shows that when orgs really double down on one modality of fundraising and get really especially good at that, that’s when they tend to grow most.

And I don’t know that means that every social impact org out there should just find only one modality of fundraising and shed everything else that they’re doing. But I do think it means there should be one that you spend 75 plus percent of your time. Yeah, dominant. Totally. And optimizing around that. So I’ll check out Lenny’s podcast around the growth engine. That’s really interesting.

Brady Josephson [00:47:20]: Yeah, no, it’s great. And I think the other thing is there’s all these halo or additional benefits of a strategy that you pick up along the way. And so that’s one of the arguments for brand is by focusing on brand reach, you often reach your own donors and it actually helps increase loyalty and retention, even though that’s not exactly why you’re doing it.

And so that’s the other thing. If you have this dominant thing that you keep investing in, there’s network effects, there’s economies of scale, there’s unseen connections. And so you can get some of that as a byproduct, whereas trying to intentionally go after it sometimes is not even the right play too, right? So yeah, that idea of a dominant way to grow or focus, I think is really important.

Eric Ressler [00:48:00]: I have one more thread I’d love to tug on with you before we wrap up here around how you’re thinking about brand versus individuals and influencers and institutions versus people, because I feel like that’s a really big part of the conversation right now. We had Amanda Litman on the show earlier who comes more from the political world and she has some interesting perspectives around that brands can’t actually have ideas, that it’s really people that have ideas.

And you see this with content becoming less polished and more authentic, to use a buzzword. You see this with the trends in technology and more influencer based content and phone-based content being created. And I don’t think, by the way, that investing in brand and doing more authentic content is necessarily an either or. I think you can do both. But how are you all thinking about that in terms of showcasing the people behind the org and considering that trust in brands and institutions is down, although trust in nonprofit organizations is down less than any other major institution, which is good news for us.

Is that part of your thinking and conversation right now internally at all?

Brady Josephson [00:49:10]: Yeah, it is. And I think we were too slow to adapt, especially on the social side. And I think that’s where not being maybe as focused on data or what customers or consumers are saying directly or indirectly through data, we were pretty slow to react. The brand is beautiful. It’s really well designed and it’s world-class. I think it’s amazing, but it’s very clear that that stopped working the same way and we were pretty slow to figure out how to make that work for us.

Being here in the United States and working in the global south, there’s a lot of issues that we want to make sure we represent the people and communities we serve in an authentic way that makes it harder to just have someone in Franklin, Tennessee up in front of a camera and talk about the plight of a woman in Uganda walking for water. There are some real reasons why we were slow to get into it as well, but there were some things that we probably could have done in terms of our storytelling here, our supporters, where we could have done more face to camera.

So that is part of what we’re doing as we revamped the strategy. Having a physical place in Franklin helps a lot in terms of storytelling and some of those things. We started developing a local network of storytellers in some of the countries and communities where we worked. So we had about five or six folks that we had on contract that were excellent creatives, but from the communities that we served and grew up there and knew the people and spoke the language. And so when we would go on a trip, we would train and then we would keep ties with them. So if we needed a piece of content or wanted that first person story, the idea was that we could go and tap them so that it could be authentic, could be first person and not from us here in Tennessee or New York. It’s difficult to scale. It’s pretty tricky to maintain, but philosophically it was really cool.

So we are thinking more about that. And then the brand risk too, I think we’ve just acknowledged, look, this is part of it. If you really want to reach people, you got to lower the access and be okay with a little bit more risk in your brand — people talking about it. They won’t say it all correctly. You might get some blowback.

So we’re a little behind in that area, I’d say. And then the one thing too is everything goes in cycles. So that’s the other thing to be worried about is right now, great. That’s what the algorithms are saying. That’s what the brands are doing. That’s what everyone’s doing. Five years from now, it’s probably going to be something else. And so I think that’s the other thing. If you’re really rooted in what a great brand is about and what is great, whether they come to our site or they do it through chat, whether they hear it from an influencer or they hear it from our founder, the core that is the brand is still what you really need to make sure you maintain as those things come and go. So that’s where I feel like, yeah, we are a little slow, but at our core, I still think we’re in such a great spot to either catch up or catch up with what’s next.

Eric Ressler [00:52:00]: Yeah. I think that’s a great takeaway that I want to make sure listeners don’t misinterpret my question that, “Oh, now brand’s not important. Don’t worry about building.” I think it’s more about how does a brand show up in a modern way right now. And I think there’s a bit of an art and science to it because we see sometimes people are just hopping on whatever the latest bandwagon is. Oh, everyone’s on TikTok now. We have to do short form video and that’s our thing.

And to your point, these things all do happen in cycles. So if all you’re doing is building on those tangential discovery platforms, but there’s no foundational brand that supports it, you may be successful in that one channel, but then you’re constantly chasing the trends and there’s no bigger brand foundation that’s being built on top of that. Whereas if you do have that stronger brand foundation, you can surf those waves as they come, but always come back to something that’s building longevity and more robust support over time.

Brady Josephson [00:53:00]: There, as you think about it, I think I’m a growth guy and one of the differences I think between growth and marketing is you come with a hypothesis. And I think that’s helpful for things like that — okay, so TikTok, what’s the hypothesis? If the hypothesis is other people are doing it and it works, that’s not a hypothesis. Because you observe what means that you’re going to do what and you’re going to evaluate success because of what. And then any good experiment then goes, “Okay, if this works, now what do we do?”

And for most brands, I think they don’t have a hypothesis. And then even if you succeed, it’s like, well, now what? Now you got to feed the TikTok beast. Are you ready to do it? Can you do it? No. So why are we doing it? And I think that’s one of the reasons why I really like hypothesis-based thinking — it forces you to have some of that rationale or ask that question, “If this works, what do we do next?” And we had that. We had this great idea and we said, “If this works, we can’t even do the next phase. So let’s not even test it. It’s not worth it.”

So I think that’s one way to guard yourself a little bit against always chasing the shiny objects — having a hypothesis. Sorry, I just wanted to get that in there.

Eric Ressler [00:54:05]: No, thank you. I think that’s really helpful and touches back to your earlier point around so much of strategy is what you say no to, not what you say yes to. And it’s easier said than done, but I think that idea of thinking ahead a few steps — what happens if this does work? What happens if it doesn’t work? And I think the art of marketing and brand building and growth is knowing how long to run these experiments for before shutting them down.

Because sometimes if you shut them down prematurely, especially when it comes to attribution being hard and some of the brand building efforts taking six months, even a year at times to really start to pay off, you’re shutting these things down before they have time. I think about our show this way. If I started to measure the effectiveness of our show Designing Tomorrow after month three, I would’ve shut it down, but I knew that it takes a hundred plus episodes to really start to make a difference. And now we’re starting to see that payoff as we’re in episode 72 right now. And that’s because I come from that more long game brand building philosophy as a designer in my background and just as I’ve observed it.

Brady, one last thing before we wrap up for today. Thank you so much for your time. This has been awesome. I feel like we could do four more episodes on any of these topics, but I’d love to just hear what is lighting you up right now and what are you most excited about? You’re on this mission — my interpretation around where you’re at right now — of really doubling down on brand at charity:water, which seems close to your ethos as a growth marketer. But I’d love to just hear, what are you thinking about next and personally, professionally, what’s getting you excited these days as you’re waking up and doing this work every day?

Brady Josephson [00:55:50]: That’s a good question. Well, I’m about to go on parental leave, so I’m trying not to get too excited for anything other than hanging out with my baby boy. I think one of the things that we’re spending a lot of time thinking about and that I’m, I’d say maybe not so excited, but very curious about is AI search and web — or bigger picture, just off platform giving. Already so many people give off platform, donor advised funds, whatever, and we’re losing data and information through Privacy Acts and that’s only going one direction.

And so trying to think a few years from now, how do people even interact with charitable causes? Do they even come to our website? Are they even transacting through our forms? It’s definitely less. We always overpredict the future. And so then what does it mean to show up in the world when that is happening? It’s a pretty big question that we’re all facing. And I think that’s really interesting and curious — I’ll hopefully be able to spend some time on that.

And then maybe at the other end of the scale, I’m really excited to get more into our monthly giving program again. I feel like we took a couple years, not off, but to really focus on major gifts and brand. And now I think hopefully in this next phase, it’ll be back to, yeah, but why do we really want to build brand and build up this future demand? It’s to really grow our movement, capture that demand. And that’s really about subscription giving in The Spring. And I just love that program. I think it’s so important for us. I think it’s so relatable and accessible for small donors, young donors, old donors. And so to put some more life and energy into that program, I think is going to be really exciting.

Eric Ressler [00:57:30]: Awesome. Brady, this has been great. Thank you so much for your time today. Really enjoyed everything we talked about and looking forward to what you all do next.

Brady Josephson [00:57:40]: Thank you so much for letting me share.

A single phrase from a previous episode sent Eric into an existential tailspin, and reshaped how he thinks about organizational identity.

Most organizations can tell you their goals. They can rattle off their theory of change, their five-year plan, their success metrics. But ask them who they are becoming, and the room goes quiet.

It’s a deceptively simple question, and it lands differently than anything in a strategic plan. Goals describe outcomes. Vision statements describe aspirations. But “who are we becoming” is identity-level. It’s personal. It implies growth, imperfection, and a direction you haven’t fully arrived at yet. And in a sector defined by impossible expectations and limited resources, that kind of honest self-reflection is both rare and powerful.

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In this episode, Eric and Jonathan dig into why this one question has become a centerpiece of how they think about organizational growth, leadership, and daily decision-making. They explore what happens when you answer it honestly: the clarity it creates, the dissonance it reveals, and the follow-up question that turns aspiration into action: “What would I do differently if I were already that?” They also wrestle with how the question scales — from individual leaders, to teams, to the social impact sector as a whole — and why right now might be the most important time to ask it.

If you’ve ever felt stuck between where your organization is and where you know it could be, or if the phrase “strategic plan” makes you feel more tired than inspired, this episode’s worth your time.

Episode Highlights:

[00:01:30] The phrase that triggered an existential crisis
[00:02:00] Why "becoming" reframes identity, not just strategy
[00:03:00] Using the question with prospective partners and clients
[00:05:00] Who is Cosmic becoming?
[00:05:30] The follow-up: "What would I do differently if I were already that?"
[00:07:00] Every decision is a vote for who you're becoming
[00:09:00] What happens when you don't choose who you're becoming
[00:11:00] How the question stops leaders mid-conversation
[00:14:30] Permission to acknowledge you're not there yet
[00:16:00] Using the question as a management and leadership tool
[00:18:00] Facing the gap between who you are and who you want to be
[00:21:00] Scaling the question from individual to sector-wide

Notable Quotes:

Eric Ressler [00:05:30]: “The next question that I ask myself is, ‘Well, what would I do differently if I were already that?’ And that’s where I think it becomes extremely powerful.”

Jonathan Hicken [00:06:55]: “Every action I take, every decision I make as an individual is sort of a vote for who I’m becoming. And that’s something I can center myself on, that’s something I can decide where I’m headed.”

Eric Ressler [00:09:30]: “If you don’t have a clear sense of who you want to become, you are inevitably going to become someone else’s version of you.”

Jonathan Hicken [00:10:00]: “Build the culture you want or you’ll inevitably get the one you don’t.”

Eric Ressler [00:14:40]: “As soon as you’re satisfied, you’re behind. And I don’t mean that in a hustle culture kind of way. I mean it in the craft, like excellence, like pursuit of growth: deep, meaningful, even potentially spiritual growth.”

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:00]: One of the ways that I’ve thought about this before is every choice that you make, every decision that you make, every email that you send, it’s basically either moving you closer or further from who you are becoming.

Jonathan Hicken [00:00:15]: I think so frequently we think of organizations as rigid and not able to evolve and grow and become like this entity with an identity even of itself. And so by framing it as something that we are becoming, you’re acknowledging imperfection, you’re acknowledging growth, you’re acknowledging a direction and a conviction. It feels very human.

Eric Ressler [00:00:35]: To me, this is the perfect time for the sector to be asking that. There’s so much changing in the world, in the sector, with how funding is happening. There’s a huge generational shift happening in culture at large. We do all owe it to ourselves in this sector to think about who are we becoming as a sector.

Jonathan Hicken [00:00:55]: Build the culture you want or you’ll inevitably get the one you don’t.

Eric Ressler [00:01:00]: Yep.

Jonathan Hicken [00:01:00]: Because if you’re not clear about who you’re becoming as the team, you’re almost certainly going to get something that you didn’t want to begin with.

Eric Ressler [00:01:10]: I’m Eric Ressler.

Jonathan Hicken [00:01:10]: I’m Jonathan Hicken.

Eric Ressler [00:01:15]: And this is Designing Tomorrow.Jonathan, I haven’t even really shared this with you yet, but we did a pod a couple weeks ago and it threw me into an existential tailspin.

Jonathan Hicken [00:01:20]: Okay. All right.

Eric Ressler [00:01:20]: So thanks for that, buddy.

Jonathan Hicken [00:01:22]: You’re welcome. I don’t even know what I said.

Eric Ressler [00:01:25]: So we were talking about who you were becoming as an organization and you used that exact phrase, “We are becoming.” And this actually came through our work together. But something about the way that you said it and the way that it hit my brain in that moment, it threw me for a loop because it begged the question for me, who are we becoming at Cosmic? And I found that I was not satisfied with my answer.

Eric Ressler [00:01:25]: So we were talking about who you were becoming as an organization and you used that exact phrase, “We are becoming.” And this actually came through our work together. But something about the way that you said it and the way that it hit my brain in that moment, it threw me for a loop because it begged the question for me, who are we becoming at Cosmic? And I found that I was not satisfied with my answer.

Jonathan Hicken [00:01:50]: Fascinating.

Eric Ressler [00:01:55]: And that was what gave me the existential spin. And so what I realized in that is that that is an extremely powerful framing for that question, which is a question that could be asked in so many different ways. What’s your desired future state? What are your goals? What’s your success metrics? Where are you going? What’s your business plan? What’s your theory of change? But something about the “who are we becoming” just changes the framing in a way that I think is exceptionally powerful.

Jonathan Hicken [00:02:25]: Literally in the case for support we did together, the front page, the headline is “We Are Becoming.” And I agree that is a powerful story because it communicates growth, it communicates transition, it communicates directionality, it communicates conviction, it communicates growth and learning and flexibility. There’s a lot in that word “becoming” that I have found powerful and I’m using it all the time.

Eric Ressler [00:02:55]: Yeah. And I think it implies a lot of the things that you just mentioned. And what it really triggered in me is that I haven’t been thinking about our work in that way as a brand. Who are we becoming as a brand? I’ve been thinking a lot more about who are we working with and what’s our business model and what do we say yes and no to? And these things that are also really important. But when I started to ask myself, who are we becoming? I found that I didn’t have as much clarity or even that I hadn’t really thought about that in far too long. So I want to tease that out as a really powerful framing. By the way, I’ve started using this question as people are approaching us for partnership and the answers I’m getting are incredible and it’s literally stopping people in their tracks.

I used to ask things like, “What are your goals? Where do you wish you would be in a year? What does that look like? What would have to be true for you to be really happy in three years?” There’s all these future framing questions that I’ve used to try and get here, but something about this exact framing, this exact phrase even, really hits people in a different way. And I think it feels more personal.

Jonathan Hicken [00:04:05]: It does.

Eric Ressler [00:04:05]: It feels more like identity in the way that it’s framed, which I think is partly what makes it powerful. So I want to riff on this a little bit today and talk about why this question is so powerful and maybe even help listeners figure out how they might be able to ask themselves that question and some of the downstream questions they should ask themselves as a way to frame their growth as an organization.

Jonathan Hicken [00:04:30]: I’m all in. This is fascinating.

Eric Ressler [00:04:35]: All right. Well, first, let’s see if I can answer who I think we’re becoming.

Jonathan Hicken [00:04:35]: Yeah. Eric, who is Cosmic becoming?

Eric Ressler [00:04:40]: So when I really break down who we’re becoming, and I thought about this deeply, this is the tailspin part. I think that we are becoming one of the world-class creative agencies for the social impact space.

Jonathan Hicken [00:04:50]: Hell yeah, I get it.

Eric Ressler [00:04:55]: And you might feel like that’s aspirational or that’s a little vague or whatever, or what does that even mean to look like? And we can get into how do you define what you’re becoming in a little bit. But to me, that is really what I’m trying to do. And I have other things I’m trying to do too personally and professionally, even with the show, which I consider to be essentially a professional passion project more than anything else in support of becoming that though. What it really started to get me thinking about is that is an incredible way to think about where we’re going. And here’s, I think, the true power that it unlocks. The next question that I ask myself is, “Well, what would I do differently if I were already that?” And that’s where I think it becomes extremely powerful.

Jonathan Hicken [00:05:35]: Answer that question.

Eric Ressler [00:05:40]: What would I specifically do? Yeah. Well, I could get into some specifics, but it’s everything from what opportunities are right fit for us or not, to how do I show up as a leader to how do I show up even on this show? It really, to me, frames the entire way that I show up individually as a leader, as a person in my life, and how we show up as an organization and just how we act. I think so much of embodying any kind of vision is about how you show up every day and act in those micro decisions. And one of the ways that I’ve thought about this before, which is both very freeing and can be paralyzing if you’re not careful, is every choice that you make, every decision that you make, every email that you send, it’s basically either moving you closer or further from who you are becoming. You don’t want to go so far to this where it becomes “fake it till you make it,” but honestly, I would lean more that way than not.

Jonathan Hicken [00:06:40]: This really reminds me of a conversation I’ve actually had with my therapist. And I think this actually maybe gets to what you were saying a minute ago about the question of “who are you becoming” feeling more identity based. Because every action I take, every decision I make as an individual is a vote for who I’m becoming. And that’s something I can center myself on, that’s something I can decide where I’m headed as an individual. And that feels really real. It feels like human beings, we grow, we evolve, we change, we respond. And as long as I know who I’m becoming, I can make those choices day to day that move me down that path. But I think so frequently we think of organizations as more rigid and not able to evolve and grow and become like this entity with an identity even of itself. And so by framing it as something that we are becoming, you’re acknowledging imperfection, you’re acknowledging growth, you’re acknowledging a direction and a conviction to make a vote for who you’re becoming with every decision you make and every email you send. It feels very human.

Eric Ressler [00:07:55]: I think that’s right. And I think in a certain way, that’s why I said it can be very empowering, right? Because what you can realize is that you have agency that — I think there’s sometimes, especially in this space, these meta narratives around — and these narratives are rooted in truth, but these meta narratives around structural issues, right? These barriers, these inequalities. And without discounting that, I think that if you start to embody too much of that way of thinking, you are giving up your own power and your own agency to change those structures and those barriers. And I’m not saying every org and every leader out there needs to be doing systems change work, but I think we have to be really aware of that because — and I’ve found myself in this position before too where, oh, the agency space is messed up and AI is eating everything and SEO is changing and last year the sector was frozen and all these excuses, these limiting beliefs that if you’re not careful, they start to really infect you in your daily decisions and how you show up.

And maybe partly because I feel like personally I am coming out of this early parenthood cocoon to some degree, some days more than others, and having to reckon with who am I becoming in my second half of life. And it’s all convergent with the agency because it’s really hard for me to separate myself from the work because I’m so embedded in it. And so I’m doing this personally and professionally at the same time. And what I realized is if you don’t have a clear sense of who you want to become, you are inevitably going to become someone else’s version of you because of the structures or your coworkers or who you’re spending time with. And I think it’s really important to have clarity around who you want to become.

Jonathan Hicken [00:09:45]: This is reminding me of a quote, and I can’t remember who to attribute it to, so I’m really sorry about that. But there’s a quote about culture building and organizational building, and the quote was, “Build the culture you want or you’ll inevitably get the one you don’t.” And it’s the same thing, right? Because if you’re not clear about who you’re becoming as a team, you’re almost certainly going to get something that you didn’t want to begin with. And I feel like that translates to an organizational strategy or identity is you have to know what you’re becoming so that you can make those decisions day to day.

Eric Ressler [00:10:20]: Yeah. And I think that what, again, to double down on this idea, I want to acknowledge that this is easier said than done. And so much of this is not even just knowing who you’re becoming, but having the conviction and the courage to actually act that way over and over and over and over again, especially when it feels the hardest, that’s when you have to do it the most.

Jonathan Hicken [00:10:45]: Let me go back to, you said that you’ve been asking clients this question a bunch, and without naming names, can you describe some of the responses or reactions that you’ve gotten to this question?

Eric Ressler [00:10:50]: Yeah. I would say the biggest reaction that I get is it feels like the most human moment in the conversation. People literally pause and stop and think, and not in a “Oh, I’m unprepared” way. It’s like, whoa, that stopped me in my everyday autopilot mode that I might be in interviewing multiple agencies or whatever. And so it’s a really powerful question. So the biggest theme is that it’s a conversation stopper in a positive way.

Jonathan Hicken [00:11:30]: And it forces a presence. It forces a reflection.

Eric Ressler [00:11:35]: Yes. Yeah.

Eric Ressler [00:11:35]: And I think it leads to people thinking more deeply, thinking outside of the strategic plan, thinking outside of even their mission and vision, thinking outside of even what some of the success metrics of any particular project might look like. And so for me as an agency owner and a creative director that so much of my job is helping people understand who they are, a lot of understanding who you are is understanding who you are becoming at the same time. And so it gives me this really insightful contextual element to this that gives me more clarity around if it’s a fit or not at the minimum, but also more like, is this something I want to be part of? Do I feel inspired to help this org or this leader become this new thing?

Jonathan Hicken [00:13:15]: We may have actually already answered this question in the conversation so far, but I wonder why a question like “who are you becoming” hits differently than a question of “what’s your vision” or “where are you headed in the next five years?” I think where my mind goes is it has something to do with this humanizing thing. It allows for vulnerability, allows for fallibility and it’s like there’s this space to acknowledge that we’re not perfect and we’re not where we want to be yet, but there is a commitment and a positive momentum towards that thing, which is a very human thing to do. And I certainly feel that a lot with being a parent, right? Because I’ve got a six year old, our kids are about the same age, three days apart, and I think a lot about who I am becoming as a parent so that I can be the best. And a lot of that is humbling because you know that you’re not perfect and you know you’ve made mistakes and you wonder how that’s going to impact your kid. And I feel like in an organizational sense too, it allows for that humility and a little bit of that space.

Eric Ressler [00:14:25]: Yeah. I think it’s permission too, right? It’s permission to acknowledge that you are not where you want to be yet. And I think that’s good. I think that if you are doing this work especially, you should basically never be satisfied. As soon as you’re satisfied, you’re behind. And I don’t mean that in a hustle culture way. I mean it in the craft, excellence, pursuit of growth, not in terms of revenue necessarily or headcount, but deep, meaningful, even potentially spiritual growth. And I think that one of the things that is so powerful about this that can be really hard, I will just say, is that the bigger swing you take with who you want to become, the bigger the gap is between who you are and who you’re trying to become. And the more you’re going to have to face where you are falling short of that.

Jonathan Hicken [00:15:20]: Dude, you know what? I think this is an amazing question to ask someone on your team, no matter what area of the business they’re in, if you’re helping someone grow and that’s part of who you want to be as a leader, asking someone, “Who are you becoming here?” or “Who are you becoming in your career?” I don’t know. This is just hitting me right now. That’s a really powerful management leadership question.

Eric Ressler [00:15:50]: Yeah. I hadn’t really thought about it that way, but I agree. And I think that I’ve always framed this as, who are you becoming as an org, as a team for your mission? But I think it could be equally powerful to your point as a management tool. What makes it hard, and I think what we need to be careful about, let’s just start with the management side is, are we giving people the space and the tools and the support systems to become something else? And are we doing that in a real way and not just piling on this like, “Yo, dude, you want me to get all this stuff done and now you’re asking me who I’m becoming too?” Come on, right? So not to shut the idea down, but I think we just have to acknowledge that, and I know that that’s the kind of leader that you are and that you have a team that has that agency and that space to have permission to fail or whatever. But I think we have to be careful about it in the social impact space where so many times expectations are impossible to meet.

Jonathan Hicken [00:16:55]: More, more, more. Sure. More, more.

Eric Ressler [00:17:00]: More, more. Absolutely. The other thing though I do want to talk about is I’ve been reflecting on this question both personally and for the org and what I’ve learned in doing that is that it’s hard at the very beginning because you see that dissonance, that gap between where you are right now that you got to be brutally honest about. Part of this is you have to be willing to let your guard down a little bit and acknowledge where you’re strong and where you’re not. And then you have that future state, who we want to become, this north star, what does it look like for me to become one of the leading, most world-class creative agencies for the social impact space? Which by the way, I will say, I feel like we’re pretty close.

Jonathan Hicken [00:17:40]: Yeah. Yeah, I really do.

Eric Ressler [00:17:45]: And I don’t mean that in a “Oh, we’re better than everyone else.” I have a lot of peers in this space I highly respect, I look up to, I admire, I talk to, and I welcome them. I don’t think this is a zero sum game at all. And yet I know that there’s work to do, right? And what I noticed is when I really decided that is it for us, that is who we are becoming and start to share that with my team, immediately you start to realize all the things that you’re doing that are not in alignment with that. That’s not how a world-class creative agency in the social impact space would act. Well, I should probably change that and I don’t need to wait. I don’t need to wait to change some of those things. And you have to balance this, but I think there’s a lot of excuses that we, and limiting beliefs and reasons why we can’t that get in the way of us actually becoming the things we want to become.

Jonathan Hicken [00:18:35]: So how often do we need to ask ourselves this question?

Eric Ressler [00:18:35]: Every single day. And I think what I’ve noticed is that it’s almost like a mantra or context setting. I wake up and look, I’m not perfect at this and I’m not suggesting you have to be either, but you should aim to do it every single day. And when you start your day, it’s a nice little setting the scene for the day. Who am I becoming and now what do I do with that? And now when I look at my to-do list or I look at my calendar, is that in service of that or is it not? And you might even want to start by writing down everything that you are commonly doing in your daily and weekly life personally and at work. And is it moving me towards or away from that version of who I am becoming?

Jonathan Hicken [00:19:20]: So apparently I said this thing that threw you into a tailspin. But honestly, I think you reflecting it back to me has also gotten me hyped up about the power of this and how to start to use it for myself as an individual, but also for the team. And I often talk with my team about stop, start, or keep doing. This is a prioritization exercise and we often align those priorities to goals or outcomes. And I’m wondering in this moment if in fact we should try aligning that exercise to this question of who are we becoming?

Eric Ressler [00:20:00]: Absolutely.

Jonathan Hicken [00:20:00]: Man. Yeah, I’m going to try it. I’m going to try it and then I’ll report back.

Eric Ressler [00:20:05]: Well, so I think what you have now is you have a really good, clear answer about who you’re becoming in this moment. And that might be different in three years. Maybe it even should be different. I think it depends how quickly you get to that version of who you’re becoming. But yeah, I do think it is a nice litmus test for everything that you’re doing and you could use your productivity framework of start, stop, or pause for every action that you take. And you don’t want to go so detailed with this that it starts to become — there’s limiting returns on this at a certain point. But I found myself reflecting on every day, what do I do? Is this the highest leverage thing that I could be doing in service of who I am becoming? Yeah, sometimes you got to do some busy work, it’s not always going to be perfect, but every day you’re working on it and you’re shedding and you’re evolving and you’re refocusing. That’s how you get there.

Jonathan Hicken [00:20:55]: You know what’s cool, man, is this is an infinitely scalable question too, because I started by saying, “Hey, you could apply this to an individual,” but I also think you could ask this of the sector. What are we becoming collectively? What does that mean? Right? I mean, isn’t that like ...

Eric Ressler [00:21:15]: I mean, honestly, to me, this is the perfect time for the sector to be asking that. There’s so much changing in the world politically, in the sector, with how funding is happening. There’s a huge generational shift happening in culture at large.

Jonathan Hicken [00:21:30]: Economically.

Eric Ressler [00:21:30]: Economically, the global order is changing, unfortunately, largely in bad ways, in my opinion, but I do feel like we are on the precipice of a new major version of the sector. And I think we do all owe it to ourselves in this sector to think about who are we becoming as a sector. So yeah, I love the scalability of this down to the micro all the way up to the macroist of macro.

Jonathan Hicken [00:21:50]: Yeah. If we’re going to start a meetup group, maybe we need to call it “Becoming” or something. Something like that. Yeah.

Eric Ressler [00:22:00]: I mean, it’s a powerful question. So I think for our listeners, think about this. Think about it deeply. Take it to your team, get everyone to do it individually and bring it together and have a conversation around that. I think it’s a super powerful alignment exercise and something about the phrasing has some sort of magic secret sauce to it. And I’ve experienced it myself. I’ve experienced it in asking different social impact leaders and it stopped all of them in their tracks in one way. Words are powerful, man, and the way you frame things are powerful. So hopefully this has some good takeaways for our listeners today.

Jonathan Hicken [00:22:35]: This is awesome, Eric. I really, really appreciate the topic.

Eric Ressler [00:22:35]: Awesome. Thanks, Jonathan. Thanks for the existential crisis.

Jonathan Hicken [00:22:40]: By the way. You’re welcome.

Eric Ressler [00:22:40]: I need one every six months or so.

Jonathan Hicken [00:22:40]: All right. Thanks, Eric.

Eric Ressler [00:22:45]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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The social impact sector has gotten very good at describing problems. We have white papers, we have statistics, we have annual reports filled with data on gaps and disparities and needs. We know how to quantify suffering. We’ve built entire institutions around it. But here’s what we haven’t built, a system for telling stories that actually move people. Think about Hollywood for a second. Disney doesn’t release one film a year on one topic and then hope for the best. They have studios, development pipelines, distribution networks, talent agencies. They build collections of interconnected stories. They build entire imaginary worlds. Now think about how the social sector approaches storytelling. We fund one documentary and even that’s rare. We cross our fingers and then we wonder why it didn’t change everything. And meanwhile, the most powerful storytelling machinery in history is sitting right there. Madison Avenue can make you cry in 30 seconds.

22-year-old creators have audiences of millions, but the social sector’s still operating like it’s 1985, pleading, shaming, and hoping that the facts alone will change minds. Hope is magnetic. Guilt is repulsive, and we know this, and yet we keep reaching for guilt. To explore what it would actually look like to truly build a narrative infrastructure for social change at scale, I wanted to talk with someone who’s doing exactly that. Heather Mason spent 20 years producing some of the biggest convenings in the social impact sector, Skull World Forum, events for Ford and Rockefeller and more. But her first career was in film, and she never stopped believing that stories are the most powerful lever we have for social change. So she built the Impact Lounge, a traveling hub that brings together funders, filmmakers, and creators at places like Sundance and Cannes to build the connective tissue the sector has been missing.

I’m Eric Ressler and this is Designing Tomorrow. And now my conversation with Heather Mason.

Episode Highlights:

[02:15] Why narrative change is the most powerful lever for social change

[05:00] The social sector treats film as a tactic — Hollywood treats it as a system

[07:05] “I invested in one stock. It did not do well. I don’t think stocks do well.”

[08:00] Marvelization: what world-building looks like for social impact

[12:30] You were hired to solve a problem — what if you were hired to create a vision?

[15:30] What the Impact Lounge is and why convenings are the crucible for ecosystem building

[22:30] How storytelling drives policy change — from the UN to Minecraft

[30:00] The massive shift happening in media and why it’s an opportunity, not a threat

[37:00] Why small teams should build, not buy — and let go of perfect

[39:30] Nonprofit product placement and the rom-com that could change conservation

[44:00] Big swing content moves vs. daily raw content — you need both

[45:00] The Skunkworks mindset: annoyingly positive in a hard year

Notable Quotes:

Heather Mason [03:45]: “Data can inform us, but only stories can move us.”

Heather Mason [06:40]: “I wonder how our film is going to do. Our film. Our one film. That is a little bit like saying, ‘Well, I invested in one stock. It did not do well. I don’t think stocks do well.’”

Heather Mason [13:00]: “If people get hired to focus on the problem, you’re going to get problem-focused experiences, problem-focused communication, problem-focused white papers. When you’re hired to create a solution, when you’re hired to create visions, that’s a very different experience.”

Eric Ressler [49:15]: “If these are the world’s most important pressing ideas and we have ultra wealthy folks who have a lot of money who claim that they want to solve these ideas, then we should be not sparing expenses on getting the most creative minds telling the stories around these ideas.”

Heather Mason [49:30]: “You have the most powerful propaganda machine on Madison Avenue. Why are we not plugging these ideas into it? We have the most viral machinery in the world, true creators. Why are we not plugging these ideas into that, into cultural supernova of storytelling?”

Heather Mason [15:55]: “Hope is magnetic. Guilt and shame is repulsive to most people. So you don’t want to repel people if you want them to come to your cause. You want to become a magnet.”

Resources & Links:

• Impact Lounge — Heather Mason’s traveling hub connecting funders, filmmakers, and creators at events like Sundance, Cannes, and Climate Week

• Caspian Agency — Heather’s events and convenings company that has produced events for Skoll World Forum, Ford Foundation, Rockefeller, and more

• Trabian Shorters’s Asset Framing — Framework on shifting from deficit-based to asset-based language in the social sector. Please research and add URL.

• Outrider Foundation Nuclear Bomb Simulator — Interactive tool where you enter a zip code and see the impact of a nuclear blast, referenced as a model for big-swing content

• Lumen Awards — Awards show created by Impact Lounge held three days before the Oscars honoring changemakers and filmmakers. Please research and add URL.

• Cosmic — Creative agency for nonprofits and mission-driven organizations, founded by host Eric Ressler

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [02:00]: Heather Mason, thank you so much for joining me today.

Heather Mason [02:05]: Thank you. Thank you for having me on.

Eric Ressler [02:07]: I’m really excited today to dig into a lot of topics, but one of the first things I think I’d like to start with is a perspective that you have, which is centered around a couple different things. We’re going to talk today about media and the intersection between media and film specifically in storytelling and social impact, but you have this perspective that narrative change is, in your opinion, the best way for social change to happen in the most impactful way. I’d like to just start there and let you unpack that philosophy a little bit for our listeners.

Heather Mason [02:35]: A lot of this stems from my love of film, so I am biased. That was my first career. But I would say it also comes from, I know there are a lot of psychological studies. I’m not going to be able to list them all. They talk about how we learn, how we share information and how we decide the rules and guidelines of a culture, the morals, the values. Those all come from stories and you can trace those back to Hans Christian Anderson tales or myths or legends or African parables. We are learning through the Bible. Religious texts, they’re all taught in stories because there are parts of our brain — and again, I can’t list all of the scientific reasons behind it — but that light up when we hear a story. And there are things that turn off and why we yawn in lectures when we start to hear the facts and statistics.

Those are important. I am not saying they aren’t, but when they’re woven into storytelling, they take on a whole different meaning. And we have a statement we say, which is data can inform us, but only stories can move us. That’s when you get a change of action is when people hear a story, can relate to it. And there’s a reason why film has been called an empathy machine. It allows us to be a part of their stories. So I do think it’s critical.

Eric Ressler [04:05]: So I hear this a lot, and I’ve actually spoken about this a lot from my purview as well, touting the impacts, the potential of storytelling, and yet we’re not really seeing that in any meaningful way shift the sector. You could maybe counterargue that. I think there’s been a lot more embodiment of storytelling, at least philosophically in the sector at large, but then there’s often still this retreat to the comforts of annual reports and white papers and academic jargon when we’re trying to describe sometimes, to be fair, these complex social issues. Why do you think that the sector at large has been so reluctant or unable to adopt storytelling in the same way that consumer brands do or that documentary film producers are able to?

Heather Mason [04:55]: I think a lot of that stems from the fact of the way that the social sector has thought of film, media, now it’s broadening out creators as a tactic, as opposed to a world, as opposed to creating a cultural ocean, as opposed to working together across stories with different organizations instead of working across silos and partnerships. Those are two different ways of thinking. And the way I would describe that is if you think about the Hollywood system, Hollywood has a studio system. They have the big ones, Disney, Warner Brothers, Universal. You’ve got the big guns. They have a system around them to distribute, to create, to work in development. I worked in development at Fox. To have that, that’s an incubator in a sense. That’s an accelerator program. You have production deals. I would say that’s probably more like accelerator, incubator, maybe development at large.

And then you also have distribution deals with National Association of Theater Owners, NATO. You’ve got conferences. There’s an entire system, but Disney doesn’t just put out one film a year on one topic. No, they have slates of films. And if a certain genre picks up, they all pick up on it. And all of a sudden you’ve got tons of superhero movies. How did that happen? Why are there two Armageddon films with meteors crashing into planets? Well, because that’s hot right now. So we’re going to jump on that. Let’s contrast that with the way that film is used, and I’ll use film again over in the social sector. We have an issue area that’s girls’ education. We’re going to do one film. I wonder how our film is going to do. Our film. Our one film. There is not an acceleration around slates of films.

There are not, how can this film be a TV series that might be distributed by a different foundation? How can that one actually inculcate a whole other studio? One film. I hope that one film works. That’s why I think people have looked at that and gone, why hasn’t that one film worked? And that is a little bit like saying, “Well, I invested in one stock. It did not do well. I don’t think stocks do well.”

Eric Ressler [07:15]: Right. So I love this contrasting thought experiment that we’re doing here, and I wonder if we can go a little bit deeper on it. And clearly you’ve thought about this deeply. So I’d love to hear what does the world look like? What does your world look like when media and film and more immersive forms of narrative change are embedded at a fundamental level in the social impact sector instead of these one-off bets that are being placed and the burden is largely falling on individual implementation organizations to come up with, create and distribute that one piece as a big swing move that maybe doesn’t pay off because of the problems that you’re describing here. What is the right way to do this look like in the social impact space?

Heather Mason [08:00]: I get so excited talking about this. And I don’t know that there’s one right way, but I’ll give you some ideas. And I will say there is a gentleman, and I’m going to forget his name right now, so whoever thinks of this can put this in your show notes, who has come up with a term called Marvelization. And I wish I had come up with that because that’s what I’m describing. I love Marvel movies. I will say that. I love Star Wars movies as well. I love Star Trek. Any of those are franchises because they’ve created a world and Marvel has created a world, that’s why they can have all those spinoffs. And the rules apply in that world. That’s what world building is called in film. You build the world, John Wick has a world. So to do this in a way that I think would work for the social sector is you can have world building and hopefully the competition wouldn’t be so great in the IP that you could, because the IP here is saving the world, so I would hope we’d be a little open source on that, is you could create more characters and more experience in a Marvelization type of world.

That is one way that if you take a large foundation is doing this, but if they started to agree in a sense creatively to be a part of these worlds, what does that look like if you win? And I know that’s been a phrase for a lot of social good folks. What does it look like if we win? And I think there is not enough time thought about that because there is so much time spent on we need to tell people how bad it is first. And I can see the relevancy there. And sometimes people get upset when I do not put enough gravitas on that because I haven’t sobbed enough or cried enough. There is a time for that. There is also a time and there is a place for people and personalities who do focus more on the world building of the solutions that can take place because I think that’s how you get there.

And I think you can look at Star Trek, why we have flip phones, world building.

Eric Ressler [09:55]: This ties into something that I think about a lot, which is this tension between needing to articulate the problem, identify the problem, talk about the stakes of the problem, talk about the relevance of the problem. There’s no shortage of problems in the world right now. I think we can all agree on that. But I don’t think there’s enough imagination, enough time spent to your point around this world building or Marvelization. I’ve thought about that in a different way around just being better about having compelling, clear, engaging visions for what does it look like if we win, to use your terminology. I think film and media has a lot of potential to do a better job of sharing those ideas. When we work with social impact organizations, we can feel that when we talk to executive directors or CEOs or founders. And then when we look at their communications, when we look at their website, when we look at their social presence, there’s this massive gap between the experience of talking to one of them or hearing them on a podcast and their communications as an organization.

Now, what I’d like to press on a little bit from your perspective, and this maybe starts to get into the fundraising ecosystem a little bit more, is my sense is a lot of orgs want to do this. Maybe they believe in it, maybe they’re a little skeptical, they don’t even see the full potential of it, but there’s an impotence in the sector. Yes, we want to do storytelling. Yes, we want to do more rich media. We want to break out of the box of the academic jargon and the reports and the white papers, but we don’t have the money to do it. We don’t have the funding to do it because it’s restricted to this particular program or because that would cost $100,000 for a documentary or whatever it is. How do we break that catch-22, that cycle of needing the funding to invest in story building at a fundamental level and not just as one-off experiments?

And where’s the burden sit there? Is it on the funder’s responsibility? Should foundations be writing checks for this? Do we need to be just building more sustainable orgs? This is the constant catch-22 in my mind around any kind of investment, but especially investment in anything that has to do with communications in the sector. How do you think about that?

Heather Mason [12:05]: That’s always going to be a tension. And anything with fundraising is where you prioritize your dollars. And I would reel this back just one step when you were starting your question on why or how does this happen in the fundraising ecosystem because they want to do this and it’s different when you talk to them. Where I think it goes a bit astray is folks are told when they’re working at some of these organizations, we’re here to solve a problem. It was set up to solve a problem. That’s why your organization exists. So when you start to hire people and say, you’re here to solve a problem, you are going to naturally focus those people on problems. As opposed to, think about if I said I was going to hire you for an organization, your job is to create solutions. That’s a very different way to think.

Your job is to create a vision. Your job is to become a visionary. And I think if people get hired to focus on the problem, you’re going to get problem-focused experiences, problem-focused communication, problem-focused white papers. When you’re hired to create a solution, when you’re hired to create visions, that’s a very different experience. And the reason I start there is because with fundraising, there is often, there’s a wonderful guy, Trabian Shorters, I’m sure some people know him who are listening to this, talks about asset framing and gaps in asset framing and that a lot of funders are focused on lacking language in order to fund things as opposed to abundance language to fund. What’s the opportunity of this community? What are the assets of this community? Not under, under, under. And that is focusing on problem. And the reason why I start there is because that’s a bedrock philosophical look at why your organization exists.

And until we talk about why the organization exists, we cannot create new priorities for what they are going to fund and what is going to be fundable. If you’re funding solutions, then maybe you’re funding a part of the film ecosystem. Maybe you’re not funding the entire production of the film. I outlined an entire Hollywood system, but there’s so many different organizations that feed into that. Some own theaters, they’re theater owners, some are doing accelerators, some are working in development of scripts, some are agents, some are collecting types of films or stories that could be funded. There is a role. I also think this is where looking at Hollywood is a good example because an organization or a foundation may be like, “We have to do everything.” Well, that’s not necessarily true, especially if you’re an independent studio, which I think a lot of different organizations could be.

Eric Ressler [14:55]: I love this metaphor of this ecosystem, and I think that social change creates or necessitates ecosystems and collaborations, which I think ties in nicely to a lot of the work that you’ve been doing at Caspian around convenings and events and bringing people together. And I’d love to talk a little bit about specifically what you’re doing with Impact Lounge since that ties into both of these topics. I’d love for you to actually just describe what Impact Lounge is and where it’s going and how that vision came to be.

Heather Mason [15:30]: And it’s funny because it’s exactly where we’re talking about, which is perfect because my whole thought after working in convenings around the social good sector for 20 years is looking back to my start in the movie industry. And I’ve always thought that that is the number one way to move hearts and minds is in stories and bringing people to hope. Hope is magnetic. Guilt and shame is repulsive to most people. So you don’t want to repel people if you want them to come to your cause. You want to become a magnet. And that is what film does. And so I thought, I’m going to bring my two loves together and create the Impact Lounge so that this movement, this ecosystem can be accelerated. And the way you accelerate, as I’ve seen at events, and I fully believe in them, is events are a crucible, when done well.

And in that crucible, those experimental little containers that we had back in chemistry class, not the book about witches, is in that little chemistry cup, you put all the ingredients to create the catalystic experiment you want to happen. And that is what happens at the Impact Lounge. So we bring together change makers, funders, and those in the filmmaking ecosystem, the creator ecosystem, so that they can start to meet. And that accelerates this movement because all of a sudden, I was on calls just even today. All of a sudden people are like, wait, I didn’t know they were working on that. Yes, they are. That’s more like studio system work. These guys are working on this. Well, we could go in on a funding thing with them. Yes, you could. You don’t have to go it alone. I didn’t know they were doing that.

Well, I know about that because we work with them with Caspian. That’s how that all comes together. And we have created, I would say, I have a success list of some major partnerships that we have been a part of bringing together because we’re forming that crucible for this to take place in. And people believe in events, they know events work, and this type of event is to bring together the, I would say, counterintuitive players. Why would a creator be on stage with one of our largest social entrepreneurs? This is why.

Eric Ressler [18:00]: And for listeners who don’t know Heather and Caspian, we’re not talking about small players here. We’re talking about Skoll World Forum and the Packard Foundation and some of the major foundations, just to speak to the foundation side of things for a bit. And this to me ties into the broader ecosystem around funding and how funding is happening and how money flows into the space because like it or not, social change needs money, it needs resources in a capitalist society. And if anything, we need way more money being spent out to the orgs that are doing this work, whether they are funders or intermediaries or the boots on the ground implementer orgs or consensus building orgs. We need the full ecosystem, in my opinion. So how do we get more of these network effects in motion and how do we get more people who are able to spend money and to invest in these causes to write checks?

I’m imagining your answer is going to be through narrative change and through story, but walk me through that theory of change and why that’s a better way of doing it than the more arduous scientific academic way of doing this work.

Heather Mason [19:05]: At a certain point, there will become the arduous academic type of work and fundraising. You have to know that these things actually have statistics behind them and studies and all of that. So that is a compliment. I don’t want to discount that. That’s definitely a compliment. But where I think about getting people to want to invest more is you start to show some of the work that has happened and how impactful it has been when you talk about, do you remember An Inconvenient Truth? Do you remember The Cove? Do you remember Food Inc? Supersize Me. Selma, Philadelphia, and do you remember what has happened with this particular org and some of the milestones that have happened in this movement? That’s probably a little fuzzier than maybe a scene that really stood out to someone in a movie.

And maybe that is why they got involved, or they probably got involved into a subject area because someone told them a story about a specific person. They probably didn’t just paper it over or they started with statistics and they led into a personal story. That’s fundraising 101. Here’s the big global need and here’s the individual stories. And those stories are told to everyone through films, creator content. And I think for any funder that says, because I know they really care, we’ve met them, we’ve seen them at our conferences, I really care about this issue because I’ve been on the ground, I’ve been involved in this, they’re crying, they’re sobbing, and I want it. Don’t you want everyone to feel that way? Yes, I do. Okay. Well, if you think you can run around and do a bunch of salons over the next, let’s see how many years you got, or you could move them to feel the same way and same passion you have doing this on a broader scale.

That is what this enables funders to do. Take the passion they feel about an issue area and translate it to a ton more people to get that excitement on the ground level for their issue.

Eric Ressler [21:15]: I want to dig into, I think there’s a very strong and maybe more intuitive case to be made that if you’re an org that is trying to activate the general public, everyday people who are maybe not experts in this issue, maybe it’s not their career trajectory, but they just care about a particular issue. Let’s take climate change. A lot of folks care a lot about the environment and climate right now who aren’t doing any of that work in their professional capacity, they just care about it as engaged citizens. I think there’s a very intuitive argument to be made there for the power of documentaries and story and media, and especially around hope instead of apathy. I think, and not necessarily apathy, but the end result being apathy of hope versus a more negative framing, a more problem-based framing, which has really been the main way that climate activism has been framed traditionally.

And I think we’re starting to see that’s not working very well. All of that to say, what about if an executive director or someone in an org that isn’t trying necessarily to activate grassroots support, but is doing more policy-driven work or policy advocacy work or consensus building work? Is there a place for storytelling for that type of org too, in your opinion?

Heather Mason [22:30]: A hundred percent. I’m thinking of, we’ve worked with UNDP before, the United Nations, and a gentleman there’s phenomenal. Boaz Palde started a very cool extinction series where he showed a Tyrannosaurus Rex coming into the UN to shine a light on what was happening from a policy perspective. He also did something around weather kids, having kids report on weather around the world, specifically focused at policy, global policy. You also have Hunting Ground, which was a documentary about assault on campus focusing around policy. I know National Geographic has done multiple types of films around policy. And some of those are focused on a very few people who can move mountains based on policy as opposed to we need this to go to be seen by millions of people in multiplexes. These are very finely focused and their success stories because of them, because people would see this and actually make change.

And then, and I know this is a negative example, but I think it’s very cool from a potential groundswell policy area is gaming. And I know we’re talking more about film, but I think of all types of media.

There was apparently an organization that showcased how climate was affecting people in, I believe it was Minecraft. And one day there was this great forest in this game, you could play in it, and the next day it was gone and everybody was really upset because you’re playing your game, you need to map your forest and know where it is. It was gone. They said, “Oh, that’s okay. Got clear cut,” because there was a policy change that allowed this entire forest to just be clearcut. Now that is impactful. And if you want to impact, there’s more people playing video games than watching films necessarily, so we will be going into that area a bit, but that was very visceral. And if you had done that on a localized level, think about that type of media play.

If there was a pipeline going through somewhere and you were able to showcase in games, media, anything that something was a problem, you could probably activate a lot more people than doing potential petitions, signs, showing up at Walmart with a checklist.

Eric Ressler [25:05]: I think the other thing that I’ve thought about a lot as it relates to this topic is that even if you are an org that is doing work in a very grasstops or policy-based arena where you need to change the minds of 10 decision makers at the state level or national level, whatever it is, wouldn’t you want broader cultural tides and support behind your decision and your recommendations? We need the general population. And to some extent, shouldn’t we be bringing in the mandates and the will of the people in policy in general anyway? So I think it was a little bit of a devil’s advocacy style question because I personally believe very strongly in the power of all of this and I believe that it has a place, maybe needs to be used a little bit differently dependent on the type of org that you are and who you’re trying to activate.

But I think sometimes that gets used as a, “Oh, well, we don’t need to do storytelling because we have 10 people. All we need to do is get them in the right room.” And I would actually challenge people who think that way to reconsider the power of this approach and of narrative change as a huge asset in your potential direction.

Heather Mason [26:10]: 100%. If I can say one more thing about that, 100%, because the other piece of this that I find so fascinating, because I have old brain, I have Gen X brain, and whenever I come across new brain, it’s so different and it’s so exciting. For instance, we did an Impact Lounge at the United Nations. So we travel, we go everywhere, we do Impact Lounge, Sundance, Cannes, UN, Climate Week, we go international, and we had three creators on stage, meaning YouTube creators at the United Nations, and we had them talk about what they were doing with impact. And those three, I keep wanting to say kids, young people, represented over 20 million followers. So there’s first that, that’s bigger than a publicity and advertising P&A budget for a lot of independent films, those three young people. But what I thought was even more fascinating than thinking about who they could influence and what big voices they had was in the middle of the panel at the UN, this gal takes out her phone and she does a live, “Yeah, I’m right here on the stage UN. It’s super cool.” Totally live to her followers.

Now, I’m a Gen X person. What we normally do is, of course, we have photos, we do video, we send that to post-production, we slice and dice it, we put it through some people. The other thing I would challenge when you’re saying, “Don’t just focus on those couple people.” I would say don’t just focus on those couple of people. And you can get a massive groundswell behind you by the time you go to those people using just creators and what they’re calling verticals, vertical shows just on your phone and you can reach 20 million people. Imagine that level of cultural pressure that could be applied while you are even building your campaign. Don’t wait till it’s pretty. Don’t wait till it’s cute. She wasn’t waiting until she was even offstage and she already had 20,000 likes.

How does that even happen? So I agree with you that waiting and only focusing on these couple people just for this pretty campaign, those days are gone. They’re over and I am not sad to see them goodbye because if those 10 people pass a law that nobody else knows should be passed, you’re pushing a boulder uphill against the wind for someone else to come and undo it because nobody knew, nobody believed in it, nobody supported it. And I think that happens a lot of times because there’s a story behind it.

Eric Ressler [28:45]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

This is a little bit of a, you could argue maybe off topic, but I want to go there. As I’ve been watching media change and someone who loves to geek out on seven episodic sci-fi, deep novels that are 1,500 words each, long form content, love media and film and the art behind it and understand that that is something that requires a lot of time, energy, budget, intention to make these beautiful films, these beautiful documentaries. And then alongside that, there’s this next generation of media coming up that is so the opposite of that. It’s live streamed. It’s vertical video. There is no production value. It’s all just authentic human expression in its raw, uncut, unfiltered form. How are you just personally thinking about the massive change happening in media? And I don’t think that that new media is coming in replacing old media. I mean, look at how many more pieces of media are being generated on streaming platforms. The movie industry is not going away, it’s just changing. But I’m just curious, how are you thinking about all that right now personally?

Heather Mason [30:45]: I get excited because I’m one of these builders people. I’m an entrepreneur by trade, of course. So I’m always seeing like, “Hey, if it’s raining, you sell umbrellas. When the sun comes out, you sell sunscreen.” So I am always that irritating person that’s going to try to see opportunities, gaps, things we’ve never thought of before are always going to be more interesting to me. And I lived through the movies are going to die because of Blockbuster. Then they were going to die because of Blu-ray. I’m definitely aging myself and everybody’s going to stay at home because they’re only going to watch DVDs forever. It’s over. And that never happened. And iTunes is going to kill concerts. iTunes has been a problem, but I think there’s always room for more.

So when I look at how the movie industry is changing, one thing that’s fascinating to me, and this goes into my event background, of course, but this also is a falloff from COVID is events are going logarithmic. Events are a hockey stick right now as far as how many and the industry. The second thing that is coming along with that is eventizing movies. Movies should no longer just be go and sit and then go home again. That’s great for Gen Xers. We love that. Go watch a movie. Everybody quiet. We go home again. That’s not what’s happening. That’s why Minecraft was so exciting as a movie where people were coming and having a great time. Barbenheimer, you now have the reason why theaters, and I know AMC is changing their theaters, you now have Netflix creating houses. So not only is Netflix not necessarily killing things, they’re now creating events around all their series. That’s different. That’s new. That’s getting people together. They want to discuss things. So you’ve got this movement towards wanting to discuss, and you also have movement towards, you have creators on set who are going to do clips and videos of a film while it’s being made.

That’s already ancillary content around a film. Are you watching the film? Are you watching the film about the film? The creator who’s going to be in the film, the YouTube kid who’s going to be in there, who’s actually shown you it being created. And sometimes the movie can be a culmination after it’s already been streamed. After you’ve been streaming it, you build a following. And now the movie theater is the pinnacle. It’s not the start. It used to be that was the start and then it trailed off into streaming. Oh, it went straight to video, sadness. Now it could go straight to streaming, end up in a movie theater and it won. And now it really wins and now people are going to go to experience it like a concert. When my favorite band puts out a song, I don’t get sad that I’ve already heard it.

I can’t wait to go see it in concert. That is almost a better way to think of how some of these — I keep saying kids, I feel so bad — young human beings are thinking about it in one way that it could change and develop. And that is exciting. And you’ve got the break apart of more art houses that are able, you can distribute straight to theater. That was totally impossible before. So I think thinking of these as more like a must-see TV, must-see experience is very different. Now that does mean if you want the award season, awards would have to change because the Oscar — but that’s why we started our own awards show through the Lumen Awards is our awards show three days before the Oscars, and we don’t have any of those rules because I think rules are going away. They need to be a lot more flexible and fluid and ours give awards for change makers and filmmakers.

But there’s excitement for me.

Eric Ressler [34:20]: That makes me think of a couple things. One, this move away from individual films to more interest in TV and serial content that you can binge. Stranger Things, season five dropping recently. And it is a world in the same way that Marvel or Harry Potter, there are these world building opportunities. And then also so many shows now have a companion podcast, which seems like 10 years ago that would’ve been the most weird thing ever to consider. But I’ve listened to those, which is so geeky, but it’s awesome. If you really get invested in a show and its characters, to me as a creative person, I’m like, how did they make this? I want to know what the showrunner thought about this and why they made the decisions that they made. And so the depth that you can go on any given piece of creative media today is just so much more. You used to be lucky to get a behind the scenes release after a film that would come special on the Blu-ray DVD, and that would be one reason why you would get it.

Now there’s so much more. Now I want to tie this back into social impact here. I’m going to try to here in a segue, which is we need social impact organizations to figure out how to produce exponentially more content than they are able to produce right now. I talked to orgs who are highly successful, who have been around for 30 plus years, who are struggling to get an email out a week. That is not going to cut it in today’s media landscape. It is just not. There’s so much content out there. And then they’re frustrated when it’s like, well, no one knows what we want to do and we’re having trouble getting support. And this ties back into this catch-22 around, well, you need to be able to invest in producing content. And it doesn’t all have to be high fidelity, high production value content.

It can be, let’s get a clip mic on and let’s talk about, I’m about to go into a convening meeting. What am I hoping to get out of it? What happened out of it? But it’s still, I don’t want to diminish. Even we create a lot of content at Cosmic, this podcast being one of them. And it is a struggle as a small team, we’re a team of eight. I personally do a lot of our content creation and distribution alongside. So I don’t want to diminish that creating content is time, effort. It requires expertise, even if it is low fidelity, off the cuff content. How do you think we bridge that gap? Let’s take it from the point of view of if an executive director or a communications manager at a nonprofit is listening to the show right now and they want to, they believe in this.

They’re like, I want to do this. I believe in the power of narrative change. I see the power of storytelling. I see how it could work towards our mission. How do I go from where I am today struggling to send an email a week to producing documentary films, to producing an exponentially larger amount of content? And how are you seeing organizations bridge that gap?

Heather Mason [37:15]: I don’t think they have to do it alone. And I also think there’s a very large spectrum of producing content. I think there’s another piece of that when you are a small team, because we have worked with organizations that have small teams as well as very, very large teams, where you do have to let go, and this is the entrepreneur speaking, you do have to let go of the perfect and accept the good. And that is just a philosophical, that’s a leadership issue. I know there’s downsides. I’ve worked in social good. I know that the landmines you have to avoid. However, to your point, we are in a different world. This is a faster world. We may have to let go of all the precious, all of the perfect, or it’s going to be irrelevant by the time we wake up and figure out how to adapt those rules.

So when I think of the creators and I think of them, and I’m speaking of YouTube, YouTube type creators or TikTok creators or any of those folks, they’re already doing it. So it’s a build, not buy situation, I would think for a small team, but also for large teams. Bring them in. Usually they will have some sort of cause like those three we had on our stage. They each had a different thing they were very interested in and it’s not their main thing. If someone’s talking about beauty, one gal was talking about beauty, but she also really likes organic, sustainable skincare. Well, that’s her thing. That’s her organic. Could you pull her in to talk about regenerative farming that also supports some of that? Maybe. And she already knows how to do it. Are you going to be able to control her? No. That’s what I’m saying.

In the world of social good, there needs to be some let go so that these concepts can go viral. We actually want regenerative farming to go viral. We want fan fiction around organic. We want things around solar. So finding those creators can do the work for you. Might not do it every time, might not do it perfect, might have to have some guidelines, but if they’ve got 20,000, 20 million followers, that may be worth it. So it doesn’t have to be documentaries. It can be a clip a gal is doing on her Instagram every other day, which is huge that moves the mark.

And the other thing I would say is too, it’s the same with partnering with films that are already being made. So a film might be made, and documentaries are awesome, but I really love narrative films that you can do what I call nonprofit product placement. There was a film last year that was about domestic violence. Wouldn’t it have been nice if we had some nonprofit product placement in that film? And what if that popcorn bucket that was associated with that film could have had a QR code? Those are two very tiny things that potentially could have been done to basically drop in an action campaign that would have nothing to do with a nonprofit having to make a film.

My belief is, I’ve written a rom-com, it’s about conservation, but it’s a rom-com. I believe rom-coms can change the world. And imagine if those 200 films that are being made every Christmas, which I would love to be a part of if anybody’s out there, I was a development executive. I know my story beats, but I already have in mind the nonprofit because I’ve written in their tagline as a key plot point of the script. These stupid people that they say the earth needs a lawyer, whatever. And at the end, the earth does need a lawyer and that’s Earth Justice and they are a critical part of my plot, but it’s a rom-com and they kiss at the end and it’s beautiful.

So that is to me, if you want to start working in this world, in my perfect world, what I would love to see is every conference we produce, every 10th person should be a 20-something kid who’s either coding Minecraft, playing Minecraft, doing a TikTok series. They should be peppered into this world. And that is the point of the Impact Lounge, is to already get them to pepper together because that’s when you figure it out, you talk to them, bring them in the room.

Eric Ressler [41:15]: I think that’s a really good point of view is that two things I’m hearing. One, you don’t have to physically create all of the content yourself. There are professional full-time content creators out there just waiting to be paired up with the right cause who should be paid for their work and their expertise and their platform and their reach. And in doing so, you’re going to need to let go a little bit and not control the narrative, which I think is something that people think, “Oh, well, we’re going to find this creator and then we’re going to give them the script.” No, that’s the exact opposite thing you should do. And most good creators will say, “No, we don’t work that way.”

Heather Mason [41:50]: Would say no. Yeah, 100%.

Eric Ressler [41:55]: So that’s just something to be aware of if you’re exploring this path. To me, it ties into a bigger thing that needs to change in the social impact sector, which is the willingness to just take risks at all. And there’s a lot of reasons why orgs have been trained to and are not taking risks and sometimes lives are on the line. But one of the risks we can take is letting loose a little bit on our content. It is not going to end the world. Every once in a while, you may get a little bit of a PR blowback, but what are the opportunity costs of not doing that and publishing yet another boring white paper or yet another newsletter digest that no one is going to read is not going to move anything forward.

So I think we’ve been preaching on we need to be more forward looking, more willing to take risks, more willing to be bold. When it comes to content, one thing we think about a lot also is there’s the daily raw, rough content. And then map out what are four big swing features we’re going to do this year, whether that’s an interactive report. One of my favorite examples of this is an org called the Outrider Foundation. It’s getting old, but it’s still one of my favorite examples. They launched, one of their key focus areas is nuclear disaster and mitigation. They launched a nuke simulator, which is a little bit morbid, maybe not so positive, but informative where you put in your zip code, you choose a bomb and you see what happens. That was a big bet content move for them. They could have released that as a white paper that no one would read except for policy wonks, but that went viral because it was this immersive, maybe negative and scary, but interactive, emotionally compelling piece that they released.

We work with our clients to try and advise, what’s your version of the bomb blast simulator that we can do this year? We don’t need to only do those. Yes, they’re expensive. Their bigger swing moves are not always going to pay off, but they’re never going to pay off if you don’t ever try them. And that can be supplemented with the more person on the street, off the cuff, low production value, “Hey, here’s what we’re doing right now. Here’s why we care about it. Here’s what you should know.” Informing and inspiring your audience at the same time.

So hopefully some of these ideas give listeners permission and the ability to think about how to get from where they are to where they’d want to be. And we do need to wrap up here, but before I do, I want to talk about one more topic that came up as we were prepping for today, which is something that you said that stuck with me, which is that you are almost, what is the term that you used? I think annoyingly positive. I think it was something along those lines. And this has been a year that’s been hard for a lot of people to be positive in many ways in the space. And so I’d love to hear before we wrap up, we’ve talked about the Impact Lounge. I know you have a lot going on. I want to give you a chance to plug all the things that you’re doing, especially things that are lighting you up and making you feel annoyingly positive in this moment.

Heather Mason [44:50]: Yes. And I am annoyingly positive. So apologies to some of your audience because I do always look for the opportunity. Every time there’s a crack in the foundation, there’s always something springing up. That’s how our world works. It doesn’t work any other way. When we lost horse-driven carriages, we got the car. So there’s always something around the corner for creators.

And one of the things, just as a mindset, and then I’ll talk about what we’re doing is during COVID, I run a live events company. That’s what I do. So everyone called me during COVID as though they were coming to my wake, “How are you doing? How are you doing?” And I was like, “I’m great.” Now for the first two weeks, I wasn’t. I’ll admit, I was not annoyingly positive. I was like, “Oh dear, the world’s falling apart and so is everything I do in my life and believe in.”

But then two weeks later, I took a note from Silicon Valley and I wish more social good organizations would do this, which is they start a Skunkworks team. That is part of Silicon Valley. What does that team do? They don’t know. They just get four or five brilliant people and go, “Here’s a big salary. Think of what is next. Think of not what’s around the next corner. Think of what is around the next glacier, hilltop and sea and moon and come back. We don’t even know what that is.” And so I started a Skunkworks team and every day I said, “We landed on a planet and there cannot be live events. What do we do?” There’s an alien race here, and that is how we became a whole different company during COVID that did virtual events and et cetera. So when I say I’m annoyingly positive, it’s because I take the Skunkworks approach.

What’s making you sad? Okay, be a Skunkworks. On this planet, you can’t do X. Take your two weeks, take your moment, you can cry. That’s okay. And then, and then, and that is the place I try to live in is the “and then.” So the “and then” is Caspian. So we are doing plenty of events. Events are going off the charts because people want to get back together. That has not just ricocheted back from COVID, it is ricocheted and added on top of itself, also because of AI. And there’s a couple people out there saying, which I agree with, AI means you can only trust in person and in person is such a powerful way to make a connection.

And then with Impact Lounge, again, I thought, geez, more years behind me than ahead of me. I might as well bring my two loves together of what I think really will work. And the other thing that’s lighting me up about Impact Lounge and where we go is I got to go to Cannes Lions last year. I’ve been to Cannes Film Festival. Of course we go there. Cannes Lions is about advertising. And when you were talking about what’s that nuclear bomb moment thing, this was exactly that.

The other piece, and I’m so glad you made me think of this, besides having a creator in audiences or bringing them into your office is ad agencies. Ad agencies, I thought film people were the most creative people in the world until I went to Cannes Lions. Impact Lounge will be having a big presence at Cannes Lions if I have anything to do with it and we get the right funding behind us, which we are fundraising, is advertising people can take a message, make you cry, make you laugh, turn out your heart and give it back again in 30 seconds.

And they do Cannes for Good. And they’re doing pro bono work for these different organizations. Now, they might not always do pro bono, so people have to get over that, but you get Madison Avenue attached to your cause. In a minute and a half, they can say anything that would turn people around. And the way I see them, and I went up to them, I said, “Those are short films. Don’t let those die. Don’t let those have a run on TV and be dead, bring them to the Impact Lounge, and we will play them like short films in between every session. Please let me have those as interstitials.” That’s what gets me excited and lit up lately.

Eric Ressler [48:45]: And I have friends who work in big ad world and let me tell you what they would do for causes that they cared about instead of products that they actually hate in real life and are forced to work on for years at a time and get their creative ideas shut down by MBAs who don’t know anything about advertising, it would be incredible. But the money’s got to be there. That’s the thing is who’s going to pay the bills on that? It shouldn’t have to be pro bono. And that gets back into the bigger structural thing around how fundraising flows. But if these are the world’s most important pressing ideas and we have ultra wealthy folks who have a lot of money who claim that they want to solve these ideas, then we should be not sparing expenses on getting the most creative minds telling the stories around these ideas.

Heather Mason [49:30]: Because you have the most powerful propaganda machine on Madison Avenue. Why are we not plugging these ideas into it? We have the most viral machinery in the world, true creators. Why are we not plugging these ideas into that, into cultural supernova of storytelling? We are leaving some of the biggest machines that we have and we created even here in this country to the sideline for Gen X 1980s fax machine level pleading and shaming and begging. That time is over and it needs to move forward into this next realm if we are going to supercharge the changes.

Eric Ressler [50:10]: Heather, I think that’s a beautiful place to wrap up. Today’s been awesome. Thank you so much for your time and sharing all of your ideas with us.

Heather Mason [50:15]: Thank you so much for having me.

Eric Ressler [50:20]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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If solving the world’s hardest problems requires the world’s best people, then why do we pay social impact professionals like they should be grateful just to have a job?

I have watched incredibly talented leaders leave our sector, people who are deeply mission driven, but simply can’t sustain careers built on sacrifice. And then we wonder, why does the sector struggle with retention or with innovation or even with results?

The big bad word here is overhead, and it’s become the single biggest blocker against investing in our people. Funders and watchdog groups have created arbitrary caps on overhead percentages, and then they point to them as if they’re a standard. And although there’s been real pushback on that approach and some genuine progress, the core problem persists. The sector still treats its workforce as a cost to be minimized rather than the most important element to their success.

So what would it look like to have a sector that invested in its people with the same urgency it brings to its missions?

To explore that question, I wanted to talk with someone who’s been inside the machinery of philanthropy and decided to reimagine it. Rusty Stahl is the founder of Fund the People, an organization dedicated to transforming how the social impact sector invests in its workforce. A former Ford Foundation program associate, Rusty has spent over a decade pushing back against the structural barriers that keep nonprofit workers underpaid, overworked, and undervalued.

We dig into the toxic legacy of the “overhead” myth, why the current menu of grant types — from restricted project funding to general operating support — still isn’t enough to support the people doing the work, and Rusty’s bold new proposal: SOS (Staff Operating Support) grants, a funding model designed specifically to invest in nonprofit workers. We also explore why nonprofits fudge their numbers to satisfy funders, what it would take to change the culture of giving, and why the sector’s greatest asset is still its most neglected investment.

Episode Highlights

[00:00] Why we pay social impact professionals like they should be grateful just to have a job

[02:45] The structural barriers holding back the nonprofit workforce

[03:20] The “overhead” myth: how a toxic formula warps the entire sector

[05:44] Why overhead became the default measure of effectiveness — and why it shouldn’t be

[06:46] The case for a well-resourced nonprofit sector in a moment of federal retreat

[08:43] Introducing SOS grants: a new funding model built around people, not programs

[11:59] How SOS grants actually work — a senior center case study

[14:27] The permission problem: why nonprofits need cover to invest in their own teams

[16:09] The MacArthur Foundation president told grantees to take time off. What that reveals.

[18:29] How do we actually get SOS grants into the nonprofit zeitgeist?

[20:29] What nonprofit leaders can do right now to start the conversation with their funders

[21:43] Rusty’s podcast, the Long Haul Grantmaking report, and where to connect

Notable Quotes

“The sector still treats its workforce as a cost to be minimized rather than the most important element to their success.” — Eric Ressler [00:00]

“You’re taking things like your charismatic leader and their work fundraising and mobilizing support for your cause, and you’re lumping that into administrative.” — Rusty Stahl [03:50]

“The nonprofit workforce is the asset, the greatest asset for any organization and its greatest expense, and it’s the bedrock of effectiveness, impact, and sustainability.” — Rusty Stahl [11:00]

“I’m using almost the restricted paradigm for the people. It’s like a Robin Hood kind of play.” — Eric Ressler [15:13]

“We should not have to rely on the president of all the different foundations to get on podcasts and say, ‘I hereby declare you can take summer vacation.’” — Rusty Stahl [17:15]

Resources & Links

• Fund the People

• S.O.S. — Nonprofits Need Funding for “Staff Operating Support” — Rusty’s NPQ article laying out the full SOS framework

• SOS Grants Concept Paper (PDF)

• Introducing Staff Operating Support (S.O.S.) Grants — Fund the People podcast episode

• Long Haul Grantmaking Report — Case study of the Haas Senior Fund’s seven-year Endeavor Fund grants

• Fund the People — A Podcast with Rusty Stahl
  

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Eric Ressler: Rusty Stahl, welcome to the show.

Rusty Stahl [01:37]: Hey, thanks a lot, Eric. Good to be here.

Eric Ressler [01:40]: I’m excited for today. I think where I’d like to start is actually to rewind a little bit. As a somewhat outsider to the space, so to speak, I’ve run Cosmic for 15 years now. The first seven of those years, we were focused on largely working with B2B and B2C organizations in Silicon Valley alongside some nonprofit organizations. And then when we kind of decided to put a stake in the ground around social impact as our focus as an agency, I was exposed to a lot of these interesting contradictions that I think unless you work in the space, you’re just not very aware of.

There’s some cultural understanding that I’m hopeful is changing and that you’re part of changing that if you’re going to work in the social impact space, you’re basically going to take a pay cut to do so. I remember distinctly talking to some executive directors that we worked with early on who said they were really highly qualified MBAs that could easily go do four or 500K a year CEO salaries that were scraping by on barely making six figures as an executive at a nonprofit.

[02:45] And I remember just thinking about this contradiction. And so we’re going to talk a lot about, I think, funding and specifically funding people and quote unquote overhead, this word that gets a lot of attention in the space. But I think what I’d like to start with is just getting your sense around what some of the biggest structural barriers are right now in terms of how the space has been set up and how those are becoming especially front and center in this moment where there are direct attacks on the sector at large, especially anything progressive happening from the federal administration.

Rusty Stahl [03:20]: Well, you named one of them, the O word, the very concept of overhead or indirect costs, which I think are both problematic and deeply embedded in the culture, in the systems that have been set up.

So the formula is you slice up the money into three slices of the pie, administration, fundraising, and program. And then you add administration of fundraising together and that equals overhead and everything left is program, easy formula, right? Simple, but toxic and not actually useful for anyone in particular.

So you’re taking things like your charismatic leader and their work fundraising and mobilizing support for your cause, and you’re lumping that into administrative and labeling that administrative, everything else from actual administrative work to that high level leadership. And just if it’s not directly connected to some kind of event or quote unquote program, you’re labeling it either administration or fundraising and then bundling those things into this thing called overhead and then taking that term overhead and saying, “That’s taboo, that’s negative, that’s looked down upon.”

We don’t want to touch it. We don’t want to fund it. We don’t want to hear about it. We don’t want to address it. We only want this other slice of the pie called program.

And that is embedded in the IRS Form 990. They request that information and it’s embedded in the guidelines that auditors get when they audit nonprofits, they have to do that. So what ends up happening is that nonprofit people have to end up fudging things. And so rather than getting real information about what it takes to run the place, funders end up getting a different kind of pie than they would really get if they really were looking at the reality.

And that warps what then funders respond to and what they think it takes to run an organization. And that seeps into organizational culture and recruitment and retention and who comes into the field, who can afford to work in the field, who can’t.

So it has all kinds of ripple effects.

Eric Ressler [05:44]: I think one of the reasons that overhead is kind of the de facto go-to approach to measuring the effectiveness of an organization is because it’s the easiest thing to measure and because measuring impact is really hard and costs money to do well, which is just like a catch-22. So it’s like, well, show us that you’re impactful. It’s like, well, we need funding to do impact evaluation to show you that we’re impactful, right? So there’s so many contradictions in this space.

I think the way that I think about this is it does come down to balance. I think everyone can agree who’s working in good faith, that there are issues in the world that we need to solve, that there are issues in the world that are not solved by capitalism right now. Some issues are, some issues are not. I’m not anti-capitalist. I think there’s a good place for free markets to produce innovation and competition and all of that, but capitalism’s not going to fix everything in and of itself because some things just don’t have a viable profit model that’s going to solve problems.

[06:46] I think we have to be clear-eyed about that. I think also we’re seeing in real time how important local organizations are to government effectiveness when so many government programs are actually implemented at the end of that stream by a local community-based organization, often a nonprofit. And so if we agree that we need to solve important problems, that there are important problems to solve in the world, that some of those problems do not have a profit motive, then by definition, we need a strong, effective, well-resourced nonprofit sector, which means they need to be funded properly to attract the world’s best and brightest minds to solve the hardest problems in the world that no one else is solving.

So I think about it that way. Now, does that mean that there shouldn’t be accountability for these organizations? Of course not. Is the right way to measure their effectiveness by looking at their overhead percentage?

[07:35] At this point, I think we could say also, of course not. That is one data point. It is not the best data point. So let’s fund these organizations. Let’s fund them properly for the scope and scale of the problem that they’re solving. Let’s make sure that everyone doing this work is doing the thing that they’re the best at and there’s not too much redundancy. I do believe that is a real problem, but let’s make sure that we’re attracting the brightest minds and that we’re paying them properly so that they have the incentive to work at a social impact organization and not one of the big five tech companies that are attracting everyone right now.

And when we have hundreds of billions of dollars to invest in an AI bubble, not saying AI is only a bubble, it’s a transformative technology, but it’s also a bubble. It seems like we have enough resources in America and across the globe to do this right. It’s just a cultural thing that needs to change.

[08:18] I want to get into this next topic though that we were talking about before the show, which is a new, I’m calling it a paradigm that you’ve invented, a new fundraising and funding paradigm that you call SOS. Can you tell our listeners a little bit about what you’re cooking up with SOS?

Rusty Stahl [08:43]: Yeah, I’m really excited about this. So thank you for the opportunity to share it.

So I think nonprofits have been under tremendous amounts of pressure through a series of crises that have kind of been compounding over the last 10 or so years. And what I believe is that the kind of grants that folks currently raise or give are not adequate to meet the needs of nonprofits and their employees and their people in the current environment in which nonprofits are operating.

And so these kinds of grants that we’ve just kind of inherited from our predecessors, they’re not in the Constitution, they’re not in the Bible, they’re not in the tax code, they’re just the way things have evolved. So there’s restricted grants that are restricted by project or for a specific program. Then we have kind of on the other side of the continuum, if you will, general operating support.

And so that’s unrestricted. It doesn’t say you have to spend it on these line items or for this program or for this function. You can do whatever you want with it. And then there are other kinds like, we’re going to fund your building a capital campaign expense or we’re going to fund an endowment. I would call that capital another kind of capital campaign.

And then there’s capacity building grants, which tend to be kind of supplemental. You’re already a grantee. We give you project restricted grant or we give you general operating support. Now we’re going to give you a smaller amount to support a particular capacity building effort like strategic planning or implementing a database. So those are kind of some of the general types of grants. And I would say the most common are those project specific project restricted grants. And a lot of people in the field have been arguing we ought to move from project restricted grants to general operating support grants.

[10:59] What I’ve seen is that none of those kind of grants are adequate for supporting the nonprofit workforce. And the nonprofit workforce, again, in my view, is the asset, the greatest asset for any organization and its greatest expense, and it’s the bedrock of effectiveness, impact, and sustainability.

And so if you’re underinvesting in the workforce through these kinds of grants, you’re underinvesting in effectiveness, impact, and sustainability of your organization and its programs. So what I’m proposing is a new kind of grant that I call staff operating support grants or SOS grants. And some folks listening may recognize that phrase SOS, right? Save our ship. It’s a signal that ships would send out if they were in trouble. SOS grants take some of the best parts of the existing kinds of grants and combine them in a new way to incentivize investments in the grantees, staff, and people.

[11:59] So here’s how they would work. An SOS grant would be restricted for investments in the grantee’s people, and that could be staff, it could be volunteers, it could be contractors. So the restriction would say, “We think it’s really important for you to invest in your people.”

Within that zone of restriction, if you will, an SOS grant is flexible, responsive, malleable, and trust-based. So you could change the particular use at any given time as the internal and external context changes.

So for example, let’s say you have a three-year SOS grant to your senior center, and in year one, you’ve got 50 staff, but no HR person. So in year one, you’re going to use year one dollars to hire an HR person. And then that HR person’s going to say, “You know what? We need better benefits. We don’t offer health insurance and we don’t give a match to retirement savings.”

[13:02] So let’s change that. So in year two, you’re going to say, “Let’s use our SOS grant to pay for that match of employees in their retirement savings to incentivize and support retirement savings and yes, let’s get some health insurance for our employees.”

And in year three, you might say, “I don’t know, the federal government is attacking nonprofits and defunding human services, so we’re going to cover those costs with our SOS grant to keep payroll going.” I’m just making that up on the fly, but that’s the point is that over time, as the internal and external context changes, you could shift how you use the dollars.

And I would say another couple key elements of an SOS grant, these are sensitive issues. Funders who want to be trust-based don’t want to be seen as meddling with how much do you pay this person? And nonprofits don’t want to say to their funders, “Hey, we got a lot of burnout and a lot of turnover in our staff. It’s a pretty toxic workplace here. So can you help us make that better?” They don’t want to say that.

So an SOS grant would be a place where you would document what you did and how it created value and how it strengthened your impact without divulging sensitive information that’s counterproductive.

Eric Ressler [15:13]: I love it. I mean, I’m smiling because I just think it’s actually kind of clever and ironic that you’re using almost the restricted paradigm for the people. It’s like almost like a Robin Hood kind of play.

And I think it’s really interesting. And I think what resonates with me is that even with general operating support growing in popularity, from what you’re sharing, and it rings true for me, you’re not seeing that those funds are being used to invest in people all the time. They’re just being used in certain ways, even in good faith to perpetuate some of the structural issues within the sector already.

So you’re saying, “No, no, no, you’re going to fund the people and that’s all you can fund, but within that one kind of meta restriction, we trust you to use that money for your people in the best way, however you see fit.” And I think that’s a really smart way to go about it and to almost, it feels like give these organizations the permission to do that, the cover to do it.

Rusty Stahl [16:09]: Exactly, exactly. It’s the permission.

On my podcast, Fund the People Podcast with Rusty Stahl, one of the most interesting moments of doing the podcast over five years was we had on, and I was privileged to have on John Palfrey, the president of the MacArthur Foundation, and we were talking about what they’re doing in response to the Trump administration. We talked about the overhead and indirect cost myth as well. But I asked him at the end, I was just like, “Well, what do you think nonprofit people should be doing this summer?” This was in June when I interviewed him and he actually said, “Take time off.”

Rusty Stahl [16:44]: And then he said that an executive director of one of their grantees had approached him and said, “I’m thinking about taking off an extended time, but what do you think?” Could we use your grant to do that? And they were very wary and they wanted his permission. And he said, “Of course, that’s why we give you general operating support.”

And so he told that story and he said on the podcast, “So any of you, anyone listening who’s a MacArthur grantee, please this summer, I give you my permission to take time off.”

Okay, we should not have to rely on the president of all the different foundations to get on podcasts and by fiat or whatever you call that, say, “I hereby declare you can take summer vacation.” So I think there’s just an interesting need for some boundaries around this that incentivize it, enable it and give that permission.

Eric Ressler [17:40]: I imagine a lot of our listeners might be in this moment saying, “Well, this is great. I would like that.” And maybe a sabbatical probably, yes. But even beyond that, yes, I believe in funding the people. I want people at my organization, if I’m an ED and myself or if I’m a staff member, I want to invest in our team and our people power.

How do I get an SOS grant? I mean, how does it even work? These are all just made up ideas, right? They’re norms. They’re not legal charters, are they? I mean, I literally don’t know how this works, but how do we get this into the nonprofit zeitgeist, especially to the funders and start to get the word out and change the culture and start to get SOS grants becoming one of the most normal things that nonprofits across the world get?

Rusty Stahl [18:29]: Yeah, that is a gold question for me. I have the same question. How do we do it?

We’re just at the beginning of rolling out the idea of SOS grants, and I think we’ll get pushback from funders, we’ll get pushback from nonprofits. So one thing I want to make sure I say is that SOS grants should be one of the tools in the toolkit for fundraisers and for grant makers.

I do hope that SOS grants become the main grant and then general operating support or project restricted supports become supplemental because that way the SOS grant gives the kind of significant level of investment that nonprofit workers need and want.

So far, I don’t know of anyone offering this in quite this particular way, so I’m hoping to get some folks to try it out and share how it went. And I think nonprofits can just start asking their funders, “Hey, we heard about this idea of SOS grants — staff operating support.

[19:29] That would be really helpful given that there’s no PPP loans coming for this crisis and we need to support our staff to get through this. And here’s the concept paper from Fund the People that shares what an SOS grant is. Would you give this a try?”

And if the funder says, “No, we’re not going to do that,” you’re no worse off than you were. But if a bunch of nonprofits start going to a funder and the funder hears that from three grantees, all you need is three different grantees to go up and say to one program officer at different times, “Have you heard about this SOS grant idea that could be really helpful for us?” They will then take that into consideration and it’ll start a conversation inside the foundation.

So nonprofits need to buckle up and just ask for this, just raise it. Just share the paper that’s going to be available on our website and with your funders and say, “I’d be curious to hear what you think about this.”

Eric Ressler [20:29]: Yeah. So step one is we got to get the word out, which we’re excited to be part of with our massive audience for this show.

Rusty Stahl [20:36]: It’s awesome. Yeah.

Eric Ressler [20:37]: But also I think it does, these little ripple effects add up. And I hope that we get to a point where this is one of the main tools that funders use and maybe even offer as this cultural change happens to, again, using that word permission, give these organizations the permission, they might feel like, “I don’t want to burn my bridge with one of my major funders and ask for an SOS grant.”

So in my opinion, the burden falls on the funders to say, “Hey, we realize through reflection and research and experience that when we fund people, organizations are stronger.” Alongside our general operating support grant we’re giving you for the next three years, we want to also offer you a separate SOS grant to help build additional people power to get all of that work done. That’s the dream state, I think, right? So let’s hope that we get there.

[21:29] Rusty, this has been awesome. Before we wrap up, I do want to give you an opportunity to just kind of plug anything that you’d like, plug the podcast. We’ll link to the concept note once it’s live. Hopefully it will be by the time this episode drops, but anything else that you’d like to share with our listeners, go for it.

Rusty Stahl [21:43]: Thank you. Thank you so much for having me on and to talk about this.

Other things we have, so the podcast you can find on our website or on Apple Podcasts or Spotify or anywhere. So again, it’s called Fund the People — A Podcast with Rusty Stahl. It’s kind of a long name, but if you just search for Fund the People in your podcast player, you should be able to find it. And we have on funders, nonprofits, researchers, even some government people talking about different issues that all connect to investing in the nonprofit workforce. So it’s got some real high quality stuff. And we have addressed things like the overhead myth on there and lots of other topics.

Another thing I’d love your listeners to know about is we have a fairly new report that came out in September called Long Haul Grantmaking. And it’s a case study of the Haas Senior Fund in the Bay Area, California, and their Endeavor Fund, which gave out these seven-year grants.

[22:50] Here’s an interesting thing. In this case, it was general operating support, but they explicitly emphasized, “We encourage you to use these dollars to create or support good jobs in your organizations.” So it was unrestricted, but with that incentive structure in place. So a sort of a form of SOS grants.

Eric Ressler [23:12]: SOS light, maybe.

Rusty Stahl [23:13]: But very effective and already two years into those seven-year grants having some really important impacts on the staff, the wellbeing of the organization and the program. So that report is a really good read and a really great complement to the SOS grants concept.

Eric Ressler [23:31]: Very cool. Well, thank you, Rusty. We’ll link to all of that in the show notes for listeners. I’m interested to dig into that Haas case study and learn a little bit more there. This has been super fun. Thanks for joining me today.

Rusty Stahl [23:42]: Eric, I really appreciate it and psyched to know about your show and be part of it. And I’m going to be a new listener. So thanks so much for what you’re doing. I’m glad you’ve turned your focus of your firm to social impact. That’s really exciting and I commend you for doing it.

Eric Ressler [23:58]: Thank you. Me too. It’s always a blast. Never a dull moment here. But yeah, this has been fun. We’ll have you back on at some point, Rusty. Thank you.

Rusty Stahl [24:04]: I’d love to. All right, thank you. Bye.

In the social impact sector, we talk a lot about systems. Structural barriers. Root causes. Power structures. And that framing matters. But I’ve also watched systems-focused thinking become its own kind of trap — this top-down, abstract, sometimes alienating thought process that can unintentionally distance itself from the very people it aims to serve.

Because systems aren’t just structures, policies, and laws. They’re people. And you can’t change a system by imposing solutions from above. You have to build with the people living inside it.

My guest today calls herself a practical radical. After her father died when she was eleven, it was basketball that saved her. A team became her second family. And for eight years, she coached high school girls in West Philadelphia, taking a program from zero wins in her first season to state champions in her last.

She believes deeply in what sports can do for young people. But she also noticed something: for some kids, sports is a hobby. For others, it’s a lifeline. We celebrate the ones who make it out — the scholarship winners, the champions — but we rarely ask about the far greater number who don’t. And we almost never ask why so many young people need a lifeline in the first place.

To explore what it actually means to be a practical radical, I wanted to talk with Beulah Osueke. Beulah is the Executive Director of New Voices for Reproductive Justice and the founder of PILR, a new initiative transforming youth sports into spaces of wellness, equity, and growth.

This interview has been edited and condensed for clarity.

Eric Ressler: You have a really interesting background—psychology, sports, social justice, reproductive rights. In our pre-discussion, you talked about being interested in the intersection between sports and social justice. How are those things related?

Beulah Osueke: I love sports. I’ve loved sports ever since I could walk and run and saw my older brother on a soccer team and wanted to do what he was doing. When my father passed away when I was 11, it was a AAU basketball coach and a new team of sisters that really held me during a period of grief. At the time, I was a kid—I didn’t know I was grieving—but sports and basketball in particular is what came in and saved me. So I think a lot of my fondness for sports and basketball and coaches and team come from that.

But I also recognize that with sports, there’s this desire to accomplish high feats—getting a scholarship, going Division I, winning a championship. And I realized that if you don’t have the foundation of your needs met—psychological safety, food, a warm place to sleep at night—you’re not going to be able to get there, or it’s going to be extremely hard.

Oftentimes when I think about sports, people like to highlight all the barriers and the resilience that people navigated. I’m asking: why do people have to navigate those barriers? Why do we require resilience of individual people as opposed to making tenacious structures and systems that look out for the good of people?

For me, I was introduced to a world of possibilities through sports—an avenue that saved me, an avenue that introduced me to people that became a second family to me. And with social justice, I think it helps ask and answer the question why. We can really look to create more solid foundations so that fewer kids have to be resilient and there’s more equity at the forefront.

I think we live in a society that often exalts people for having to navigate really tough situations, but our society doesn’t equally ask why and look to put an end to those strained circumstances.

Eric: I want to tug on that thread because I think it’s fascinating. Sports requires resilience, and there’s some good in that—these challenges you have to overcome, these personal transformations that can happen. At the same time, especially in America, there’s this meta-narrative of pulling yourself up by your bootstraps, working hard, grinning and bearing it. I don’t think that’s all in bad faith, but there are structural issues that run counter to that narrative. We’re not all starting with an equitable start in life.

It’s not an either/or. There should be individual resilience building and transformation and cultures that allow people to have those powerful human experiences, but we also want to get everyone starting as close to equal as possible.

Beulah: Yeah, I agree. There are themes that show the brilliance of communities. Think about the grassroots effort—that one kid that has all this talent and the neighborhood might pull together to get that kid resources to set them up. Think about these athletes that are crying because they put so much into it. Sports can really elicit that human component. Music unifies people, sports unifies people. You can have people on different ends of the political spectrum rooting for the same team.

But what I’m touching on is: there are some people that get to play sports as a hobby, and there are some people that are playing sports as a lifeline. If we continue celebrating the ones that make it out but don’t analyze and assess the higher percentage of people that don’t, we don’t get to the root of the problem. What ends up happening is we individualize that story—whether success or failure—and there’s many more kids that don’t have access to what they need, that are just kind of falling off to the wayside. And it’s like, “Well, you deserved it.”

Along with that meta-narrative of resilience and personal overcoming is another narrative: that if you don’t have good things, you deserve poorness. That narrative is driven into kids’ heads early on who are in the midst of survival.

One of the things about social justice that became the biggest relief to me once I started getting into it was realizing that my misfortunes were not from my own personal failings. We have inadequate systems and structures that are not looking out for us all on an equitable lens, but also that kind of keep things in place. There’s this perpetuation that those that are wealthy and rich deserve it because they’re smarter or whatever, and those that are not deserve it because they’re lazy. That’s a lie that I think is deeply rooted in capitalism—to encourage people to stay on that hamster wheel instead of inquiring, “Why don’t I have my basic needs?”

When it comes to the intersections of sports and social justice, what I most love about it is that anyone and everyone knows what sports is—has either played, has a child that played, had a family member that played. But sometimes social justice can be very pie in the sky. So I love the marriage of the two. I love the marriage of anything social justice and something that’s practical, because I believe in being a practical radical—showing people what’s possible through the lens of what already exists and just improving what already exists.

Eric: You mentioned that this on-ramp to sports was kind of your first exposure to even the concept of social justice. That led you to becoming an executive director at a social justice organization. Can you talk about what that transformation was like?

Beulah: I did play sports in my adolescence and I’m now the executive director of a reproductive justice organization. But in between those two very different realities, I actually entered movement work through a faith-based organizing entity called POWER—Philadelphians Organized to Witness, Empower, and Rebuild. I was a communications director there. I knew nothing about social justice. I just knew what I lived. I knew what I navigated.

That experience was transformative. I got introduced to a God of righteous anger. I got introduced to the principles of faith broadly, Christianity more specifically, that talks about giving your shirt to the naked, feeding the hungry. Never before in my adolescent years had I connected the teachings of Christ to social justice. It felt like this holy essence, this holy being, is caring for the people that are pushed off to the side. But most of the teachings I had received were about prosperity gospel—follow these rules and you’re going to be rich and wealthy, you’re going to have all the cars.

I was never before introduced to the grounded discipline and commitment of being a person of faith living in a world of perpetual and insurmountable inequity. When I participated in POWER and did their communications work, my eyes were so open. I was sitting alongside priests, imams, pastors, atheists coming from different fields of faith saying, “This is not right. And our faith tells us to do X, Y, and Z.” It helped me release myself from toxic theology—the faith or religions that are like, don’t do this, don’t do that, but don’t tell you what to do or give you a practical guide.

I was introduced to people that are passionate and unapologetic about pursuing a better life, not just for themselves, but for what Reverend Dr. Martin Luther King called the beloved community. That was my introduction to justice.

But at that particular organization, there was restricted funding that limited the issues we could focus on. I participated in a fellowship that introduced me to the Black radical tradition, and I got kind of radicalized. I was like, “This is nice, but we don’t talk about queer issues. We don’t talk about women’s rights. This feels inadequate. It feels insufficient.”

I was lamenting to a friend—you know how it goes when you’re unhappy with a job—and she sent me a job description for a communications manager position at New Voices, the organization I’m currently at. I entered as a comms position, and four to five promotions later, I’m now the ED.

I really think it’s critical that my entry point into the reproductive justice realm was actually through faith, because a lot of people act as if being a person of faith and someone who advocates for the complete bodily autonomy and freedom of all people are at odds with each other. For me, they actually complement each other.

Eric: What I’d like to talk about is your background in psychology and communications and how that informs your worldview and leadership style. We work with a lot of social impact organizations with executive directors whose background is in research or science or policy. Communications can feel like this squishy, unscientific, weird amalgam of storytelling and vibes. How do you think about communications in this work, and how important is it?

Beulah: I’ve definitely been exposed to people that think comms and psychology is soft science and not necessary. I think that’s interesting—we can bookmark that for another day.

For me, I love the fact that I started in psychology. Actually, toward the end of my graduate program, I was like, “I can’t do this for a career. I’m going to take people’s stuff home with me. It’s going to bleed me out.” But through a leadership lens, I’m so grateful that I did it.

One of the first misconceptions I unlearned as a psychology student was that I don’t have the answers for people. People have the answers. A skilled psychologist, a skilled communicator, a skilled coach, a skilled person that knows how to facilitate someone else’s growth—they know the right questions to ask, the observations to make. They know how to shepherd people to their own epiphanies.

Given that I used to coach high school, it’s not as meaningful or worthwhile if you give answers to someone else, because that’s your answer for them.

I think both communications and psychology help you identify circumstances, teach you to be very observant. You can have your own articulation and conclusion, but it’s really your duty—particularly when you’re in a leadership position—to help pull that out from the person who might not be seeing it for whatever reason. They might be too close to it. They might be navigating some adaptive strategies or coping mechanisms.

I actually think that people skilled in psychology and communications have a sense of clarity—not judgment, but clarity and observation—that makes the implicit more explicit. Comms, psychology, all the “soft, not real stuff,” whatever—provides very fertile ground. Whereas other backgrounds or disciplines are more black or white, more “it has to be this way.”

It’s interesting that you say most other EDs have that background, because I can kind of see it. Maybe we need to push for more EDs with backgrounds in psych and comms.

Eric: The solutions exist and they are in the community. To some degree, social justice orgs’ job is to help shepherd and surface and amplify and support and build infrastructure for those ideas. How do you do that in your work, especially around reproductive justice, especially in a time with so many barriers from a policy and federal level?

Beulah: Whenever I talk about reproductive justice, I like to make sure there’s a grounding and shared understanding. There’s a reproductive ecosystem with three primary pillars: repro rights, which looks at legality; repro health, which looks at the actual healthcare people receive and the quality; and repro justice, which examines access. Something can be legal and the highest quality, but if people cannot access it—if poor people can’t access it, disabled people, elderly people—then it’s not equitable.

I like to make that distinction because people often conflate them all together or don’t even know there are three separate pillars, which is okay. That’s the role of education and bringing people into the fold.

I’m the executive director of a reproductive justice organization. Reproductive justice was founded by Black women. It centers Black women and people that are marginalized by their gender, sexuality, social markers.

Honestly, the first year of being an ED was a lot of cleanup. That’s not surprising to anyone—anyone that has come after a founder knows there’s a lot of cleanup you have to do. Financially, administratively. The organization invested a lot of professional development into my staff capacity because a lot of my team members come from divested communities. Education isn’t great, or family structure is challenging.

I also want to name that you have to make sure you have a solid foundation or base, because otherwise your initiatives aren’t going to make sense, or you as the individual person are going to have to be at the helm of everything, which is not sustainable.

The second thing I realized once we got our foundation settled is that this is too pie in the sky. I do believe academics and the academy play a role in social justice work, but we have readily adopted language that’s not accessible to everyday people—or the people we want to reach. I’m not saying dumb it down. I’m saying make it accessible.

One of the things we did at New Voices that I’m very proud of is we launched Political Homes for People—we call them the People’s Portal. Wherever people are, they enter the People’s Portal and we’re granting them access to trainers, speakers, a new way of thinking and being and looking at the world.

We have hubs in each of the cities we operate—Cleveland, Pittsburgh, and Philadelphia—where people come together on a monthly basis, talk about their current conditions, talk about why they think that is, what’s the source. And together they arrive at this collective: “Ah, it’s not me. It’s misogyny. It’s not me. It’s X, Y, whatever reason.”

From there, we don’t just stop at this new awakening or awareness. We plug people into tangible, concrete, accessible, and ongoing ways to chip away at that injustice. So twofold: you have this individual, personal-level community building—”Oh my God, I see how this is true for my life and what’s possible for my life”—but then you also have what’s possible with collective action, with sustained engagement.

I’m oftentimes critiquing people that share a post or attend a rally and they’re like, “I’m done. This is enough MLK for the day. I’m good.” The struggles are hidden, boring, tedious—but there is huge possibility between that first awakening and seeing shifts in structures and systems and realities.

Eric: I want to talk about language. We spend a lot of time helping clients understand that using simple, plain language is not dumbing down their message. Even if you’re trying to reach people who know the jargon, it’s still, in my opinion, a defense mechanism. It shows a lack of confidence in truth and knowing, because if you really deeply know something, you should be able to say it plainly. That’s not easy—it’s actually quite hard.

If you look at the true experts, the true thought leaders, they’re going to be the first to say, “I don’t know all of the answers. I’m still learning every single day.” That curiosity and beginner’s mindset is what allows you to achieve excellence.

Beulah: It’s so funny, Eric—we’re talking about big words and I heard you just sneak in “obfuscating” and I’m like, there you go.

Eric: Yeah, see, I’m guilty of it myself.

Beulah: One of my favorite words is “proliferate,” and anytime I use it I’m like, someone’s going to be like, “What does that mean?” I love that word.

But I totally agree. This is why my relation to sports and social justice are inseparable—because I could very much see myself using these fancy languages, getting defensive, and people are like, “But why? How does that make sense?” if I didn’t coach.

I’m learning about this new movement, reproductive justice. I’m like, “What the hell? What is this? There’s a movement for Black women, by Black women?” And I’m also coaching young Black girls in West Philadelphia that don’t have all the provisions as children that they should have. These are kids telling me, “Coach B, I want to go Division I. Coach B, I want to win this championship.” And they don’t have consistent housing.

What I realized was my formal career in RJ was the theory, and coaching was the practice. They were oftentimes in tension with each other. But I think that’s why I’m very here—I’m very optimistic, I think we deserve so much more than what we’re getting—but I’m also like, we cannot be too pie in the sky because we lose the very people that we say we’re advocating for.

There’s a thought leader named Andre Banks who has this phrase called “cultural intelligence” that really resonates with me. He defines cultural intelligence as the ability to read the emotional and material conditions of the city and then craft a campaign that tells the truth people were already living.

That’s what I think you and I are saying. The role of the organizer, the role of the academic, the role of the person who believes in a better reality than what we’re currently existing—it isn’t to be pie in the sky, off in the corner with your smart friends throwing around fancy terms. As Toni Cade Bambara tells us, our role is to make the movement irresistible.

How do you help people realize? How do you empathize with people and say, “I know how that feels. This sucks. This should not be how it is.” You don’t just stay there—you say, “Look what’s possible.” And you don’t just stay there. You walk alongside them every step, regardless of the challenges, regardless of the hopelessness, regardless of defeatism. That is liberation in practice.

It is not doing the same thing that our current government officials do and looking down on our people. We have to be very careful to build power with our people, otherwise we’re going to replicate the very same power structures that we’re now critiquing.

Eric: Let’s pivot to your latest initiative called PILR. Tell us about how it came to be and what you’re most excited about.

Beulah: I am so excited about PILR. If you’re listening to this, just know that I’m smiling super big.

PILR is essentially a community-building model where young athletes, parents, and coaches all collaborate to transform youth sports. We envision an even playing field where every young athlete is fully supported—not just on the court or on the field, but in all things that they do. Our mission is to transform youth sports into spaces of wellness, equity, and growth.

I coached high school girls basketball for eight years. The first season, we did not win a game—we were 0 and 18. The last season, we were state champions. A lot happened between that first and eighth season. That’s where I really got grounded in realizing it doesn’t matter what I develop on Xs and Os. My kids can have the best swag. We can have gyms full of people. If I’m not conscientious of what these kids are navigating when they’re out of my view, I cannot show up and support their holistic development the way I want to.

I developed PILR because I did not get the support I needed as a coach. A lot of coaches are extremely powerful and influential and do not have a support system. They don’t have a community of values-aligned people. They don’t have access to entities or institutions or individual leaders that can help push their mission forward, that can help fortify their leadership.

We’re in development mode, looking to launch next March around March Madness. We want to provide support, clarity, and guidance to parents and guardians, coaches, and community members that want to play a role in championing young people in their lives.

I have a brilliant innovation director and a brilliant creative director. I’ve been ideating PILR for years, and now it feels surreal that we’re at a point where we’re about to have a seed gathering—we bring in 50 people that we’ve socialized this idea with and start testing our assumptions. This is what we assume people need. How do we compare that to what people actually want?

From October until March when we launch, we’re going to go through a number of rounds so that when we officially launch and introduce it to people, people see themselves in what PILR offers. I’m envisioning chapters across the nation where anyone that’s part of the sports ecosystem can tap in and get what they need—whether it’s material support, education, or just relationship.

Eric: I want to go deeper on that. I’m hearing elements of co-creation, elements of idea validation. That makes perfect sense based on how our conversation has gone—really truly rooting people at the center of this work, not coming in with a solution but creating the solution with the community. Share more about how that’s gone—assumptions that were tested, surprises or validations in that process.

Beulah: Eric, you’re really good at your questions. I’ll be glad to share about that.

Because I was a coach, one of the assumptions I made was that coaches are who need to be invested in. Coaches are the ones there with the kids. I was able to recruit two brilliant team members that are actually currently working pro bono, as am I, and they’re both parents. From there, I went from the hyper-focus on coaches to: oh wait, it needs to involve parents and guardians and young people too.

It was really hard for me to release that idea of focusing on coaches. I’m like, coaches are always thrown under the bus, always disregarded. But I trusted the process. I trusted these brilliant people I brought to the forefront. Now you cannot convince me that it’s not at least those three entities.

With that, I’m also like, coaches need workshops, we need leadership development sessions. We’re actually now leaning towards developing a wellness-centered playbook with different modules—how to navigate race, how to navigate gender, how to navigate these social justice concepts. If we kind of deflower them and just have them at face value, kids deal with it all the time.

I know so many Black kids whose parents have them at white-dominant schools for better resources, but the kids are navigating racism. Their white counterparts are saying, “You’re only here because you’re good at basketball.” That’s so dehumanizing. So we have modules for that. But we also have modules for how to create strategic and fruitful partnerships in institutions and beyond. We also have literal budgeting—when I was a coach, I had to budget a little bit of money.

That’s an assumption we’re making—that people would appreciate this wellness-centered playbook. So we’re going to do an empathy map. But also, if the data from our empathy mapping tells us people actually just want to be in community, then that’s something we have to release, because our real users are telling us what they want.

One of the things I’m really enjoying in this period is that we have parameters, structure, aspirations, ideas of what we need to do to get there—but we also have flexibility. You cannot offer something for a community and you cannot say something is co-created if you’re not willing to make shifts once people show up and give you free wisdom.

We’re literally saying these are assumptions because we don’t know, and we’re trusting people to tell us what would actually gain traction for them.

Eric: This is exactly the right way of doing this kind of work. If you come in too vague and say, “Hey, what do you all need?”—there’s not enough structure, nothing to react to yet. Coming in with assumptions based on life experience, coming in with a rough plan but a willingness to truly listen and change your beliefs—which is difficult as human beings—that’s hard.

If you’re truly going to do co-creation or community-based work, you have to be willing to listen to what the community tells you, even if that’s not what you want to hear. It’s an art and a science. Because if it’s completely democratic and you’re trying to solve all things for all people, you water down your focus. You get into mission drift or mission creep—we start here, then we’re adding auxiliary things on, and we don’t have the resources or capacity to do that work well. Now we’re trying to do 10 things and not doing any of them very well.

Beulah: Precisely. You know how it is, Eric, when you have this idea—you’re a founder, innovator, entrepreneur. I was talking about this with someone and she was like, “Well, you don’t want to say just parents. Some kids don’t have parents.” Most of my kids do not live in a two-parent household. I know that.

But I also know for the stage we’re at, I need to say parents. Because if you start watering it down—guardians, caretaker—what does that mean? Then it gets into, how do we define X, Y, Z? I’m saying parent because a non-parent can function as a parent. Of course I also want to say parents and guardians to acknowledge the vastness and the roles that people play. But I’m trying to get schmoney. So I’m saying parent so I can be clear that I know what we’re talking about: the young person themselves, the parent or parental figure, and the coach.

To your point, it is so difficult to have specificity and also the appropriate amount of flexibility. And that makes me think about leadership. A lot of people think leaders should have all the answers, leaders should be warriors—strong men, strong women. No. The most effective leaders are actually servant leaders. They’re the people that say, “I have this toolkit, I have these abilities. If I’m going to support this person getting from point A to point B, I have to figure out what their barriers are, what their potential blind spots are, and what from my toolkit can I pull—but also what from their toolkit might they not be acknowledging.”

I always feel like people either pay for it on the front end or back end. When you lead through servant leadership, when you’re truly collaborative, you pay for it on the front end. There’s a lot of ego death that has to happen. People can mess with your vision. But if you’re steadily holding onto your North Star—the best-laid plans of mice and men often go astray—you’ll eventually get there. You have to be willing to adjust as signs are coming to you.

Eric: I think it’s a tough balance. This is something I struggle with running my small organization of eight people. We’ve been around for 15 years. Our North Star has changed many times.

Because of my background in design—and in my opinion, good design requires empathy and curiosity—if you get those two things really dialed, good design flows more freely from them. That by definition means there are many ideas I have around what I want my organization to be and how I want to help people, and then there’s the reality of where different organizations are coming to us needing help.

We serve this niche of social impact organizations. I’ll be blunt: we are not structured or a good fit to help organizations in the startup phase. That’s not our skillset. For a long time, I wanted to offer something to those people because I care about the work and want to see everyone succeed. But I had to come to a point of clarity: we’re actually not serving them by taking them on and not doing our best work.

Instead: here’s a bunch of free resources that can help you get started. Here’s partners more fit for your stage of organization, so that we can get much better at the types of clients we’re best fit to serve.

Little examples like that, as well as big ideas I get jazzed about where I can see the vision—then there’s the hard work of getting validation, and sometimes not getting validation. Putting ideas out there, experimenting, and saying, “You know what? This experiment failed.” That’s a negative framing, but a failed experiment is actually one of the best outcomes because that’s the fastest path to learning.

This is the hard work of leadership—building new solutions and challenging the status quo of what has been versus what could be. But if you approach it from a lens of curiosity and experimentation, it’s way more fun too.

Beulah: Absolutely. Thank you for sharing that. I resonate so much with what you offered.

I really want to introduce the word discipline. Many people that want to do good in the world can be accused of having bleeding hearts. When you have a bleeding heart, anyone that needs anything, you want to give them anything they need. That does not allow you to pour into whatever your vision is, to have a judicious nature about yourself. That’s something I’m learning.

When I became ED, so many people came to me with requests—jobs, money, favors. I’m not going to lie, it kind of hurt my feelings. I’m like, I’m a human. I’m the same friend before I entered this role. I felt like people were reducing me to a favor. I processed this with my therapist and she said, “I can see how it can feel that way, but perhaps people are just being resourceful. They don’t see it as taking from you. They’re like, ‘This person is positioned to help me.’”

When I think about innovation and the ideas I have, people are not necessarily trying to pull me off track. People are like, “How do I benefit from this? How would I want to switch it or shift it to meet my needs?” So I do think there’s a level of discipline and commitment.

It’s easier to say yes than it is to say no. Saying no is really hard. I appreciate that mindframe switch you had. I don’t want to say I love rejection, but I don’t hate rejection as much as I used to—because it’s data. I’ve been rejected from so many things, but it’s data. It also doesn’t steal your time, because maybe it’s not meant to be.

Eric: The word discipline is really important. What I’ve found is that discipline requires strategic clarity. If you don’t have strategic clarity—if you don’t know deep down what is my identity as an organization and as a person—then there’s this “maybe this is for me, maybe this isn’t.”

I don’t think strategic clarity is something you have and then you have it the rest of your life. It’s consistently evolving as the organization grows. That’s been my experience personally and watching clients we’ve worked with for close to a decade. Strategic clarity is something you constantly need to have tested. But when you have it, it makes it so much easier to make quick choices that you know are right—because you have guardrails and discipline.

When you have that, it feels almost like a superpower. You’re like, “I know so clearly what is a fit and what is not a fit.” And I know that saying no is the right choice for me and whoever I’m saying no to—especially if I can connect them with someone who’s going to be the right yes for them.

This is actually a great place to wrap up, but before we do, I’d love to give you an opening to pitch anything you’d like—where people can follow you, how people can support you who are inspired by this conversation. This is your plug zone. Go for it.

Beulah: Thank you. Well, first of all, again, thank you for having me on. This has been fun.

People can find me on LinkedIn—just look up my name, Beulah Osueke. I accept any request that comes. I won’t be like, “Who’s this stranger?” I’ll just accept it.

And yeah, I’m really excited about the work that my team and I are doing with PILR. You can just type in PILR training. Our website will come up.

The last thing I really want to offer is: I can imagine the people that listen to this or read this are innovators, entrepreneurs, great individual thinkers. I really want to encourage people to build a village. Build a village of people that are equally bright, people that might have a little bit of different perspective—because I have learned so much from being vulnerable, from leaning onto people and recognizing I can be wrong and I can be shifted.

One of my favorite quotes, and I’ll wrap up with this: “What’s destined for you is far greater than what you desire. This is why surrender is essential.”

The first time I read that, I was like, “What a loser take.” But it’s actually—you could be looking at something that is minute compared to what is possible for you. But what you were looking at was possible with you as an individual, versus you submitting yourself to community and the brilliance that comes with that.

I just want to lift that up: sometimes it can feel like we’re losing or going the wrong way, but there’s submission and yielding to anything beyond us as individuals that is required for us to take that next leap. And I’ll stop there.

Eric: Beautiful. I think that’s an incredible message and one that’s really important for our time in history right now. Beulah, this has been amazing. Thank you so much for joining me today.

Beulah: Thank you again for having me.

Beulah Osueke is the Executive Director of New Voices for Reproductive Justice and the founder of PILR. Find her on LinkedIn or learn more about PILR at pilrtraining.com.

I’ve worked with enough nonprofit boards to notice a pattern.

Some boards are force multipliers. They ask the hard questions. They open doors the CEO can’t. They show up when things fall apart. They make the work easier, not harder.

Other boards are an anchor. They second-guess operations they don’t understand. They demand reports they won’t read. They shut down smart investments in the name of financial responsibility.

And here’s what I’ve learned: The difference isn’t about finding wealthy donors or well-connected people.

It’s about design.

Most nonprofit boards are set up to fail. Board members don’t have clear expectations about their role or responsibilities, or where they have influence and where they don’t. They aren’t trained on the very real skills required to sit on a governance board. And they’re shoved into systems that are built in good faith, but don’t allow them to bring their best strengths to the table.

But when you actually design a board — with the same intentionality you’d bring to building a product or shaping a strategy — everything changes. Because building a highly functional nonprofit board might be the single most important thing you can do to build a sustainable social impact organization. It might even determine whether your organization can actually deliver on its mission.

To explore what designing effective nonprofit boards looks like in practice, I wanted to talk with Rob Acton.

Rob founded Cause Strategy Partners 11 years ago after serving as a nonprofit CEO and watching boards either multiply impact or drain resources. Since then, he’s placed over 3,000 board members across 1,500 organizations. He wrote Becoming a Causey, a roadmap for effective board service. And he’s spent a decade figuring out exactly what separates boards that work from boards that don’t.

Full Interview:

Eric Ressler: I’m really excited today to dive into all things nonprofit boards, specifically governance boards. I’ll start by saying we’ve had a lot of board exposure working with social impact organizations and our clients. I’d be lying if I didn’t say that we often look at the board as a barrier to getting good work out the door — which I say carefully and intentionally and not with disrespect. But it’s been a challenge for us. I think we’ve seen it oftentimes be a challenge for our clients as well, where the board feels like this invisible hand that has influence in sometimes not a very constructive way. But I’ve also learned through working with you and through studying the work that you do, that there is a better way and that a board can also be an incredible asset for organizations. I’ve seen that firsthand too. So what I’d love to start with is just to get your opinions and your perspectives and your experience around what is it that makes a nonprofit board constructive and helpful and a force for good instead of something that feels more like a barrier for social impact organizations?

Rob Acton: That’s probably one of the core motivators of why I launched Cause Strategy Partners 11 years ago. I served as a nonprofit CEO for 11 years and had the opportunity to see what it looks like when you have the right people in the right seats who understand the role and are doing the role — how that multiplies a leader’s opportunity to drive mission impact versus a board that becomes a net drain on the organization.

I can’t think of anything worse than a nonprofit organization — we don’t operate around the edges of society, we’re taking care of homelessness, kids, the sick, the environment — to have a board that’s actually draining resources instead of contributing. It’s just not appropriate.

Top of mind elements of a great board: First, high expectations have been set. We’re not embarrassed to say this is a real set of commitments — a meaningful amount of your time, your resources, opening your network to the organization, contributing the core talents you bring to the board. I’ve seen people apologize for the roles and responsibilities and expectations. That makes me sad. There’s no apology. You’re stepping into a role where you’ll be one of 10, 12, 15 people shepherding this important work.

Second — and this is the theme of today’s conversation — designing that board. Not just “who do we know?” or “does anybody have a friend who might want to serve?” But really being thoughtful around what is the right mix of backgrounds, experiences, skill sets, industries that we need represented in these strategic conversations. Really designing that board instead of letting board development happen to you.

Third, great boards are well-trained and have a culture they invest in. It’s not a group of strangers who show up at four meetings a year. A great board invests in becoming a team. They know one another, trust one another, communicate with each other. I chair a board — Broadway Inspirational Voices — and we have two meetings a year. We take the first hour at those in-person meetings, literally says on the agenda “board culture time,” and we engage with one another around fun activities, go-around questions, getting to know one another, because it matters that you’re a team.

Eric Ressler: I’d love to dig in a little bit more about something that you said that’s a little bit surprising to me around you shouldn’t apologize to the board for setting a big ask, essentially. And I know that what’s interesting to me about that is that it does feel like board positions are often volunteer positions, unpaid positions, I would say in 95% of cases for nonprofits, if not more. And so what I’ve experienced also is that it can be hard for younger professionals, professionals who don’t have the means to dedicate extra time and energy to show up and do that volunteer work, especially in a meaningful way, especially when oftentimes there’s a spoken or unspoken expectation that part of the role of being on a board is to give money or to open your networks. And yet there’s also this drive, and I think this is really core to your work as well, around making sure that boards aren’t just a bunch of old rich white people, to put it bluntly. So how do you manage those two sometimes contradictory scenarios?

Rob Acton: The nonprofit sector has really shifted over the last decade. I don’t see a lot of organizations anymore that are like “who can write the biggest check and those are the only people we’re interested in.” There’s a lot more awareness that diversity matters. When I say diversity, I mean across a range of spectrums. Racial and ethnic diversity of course matters — that’s been an area where the nonprofit sector has traditionally fallen behind. Look at the community the organization is serving and then their board, and it’s not reflective. We have to change that.

But there are many other aspects of identity — gender and sexual identity, living with disabilities, age. Then we need to look at skill set, industry, sometimes geography if the organization is serving multiple geographies, and life experience. Being thoughtful around building that board that will serve our organization well is what matters.

We need money to run nonprofits — you’re keenly aware of that as much as I am — but that won’t get you the whole way. When a board has delegated everything else to the CEO and their team and said “okay, we’ll just raise money,” they’ve really lost track of their core responsibilities. Boards shape strategy. Boards ensure that strategy’s coming to life. Boards leverage their core skill sets in the boardroom to make wise decisions in a complex operating environment and sometimes in crisis. Boards provide fiduciary oversight, financial sustainability, and manage the CEO’s efforts.

It’s about much more than writing that big check, and I’m happy to say I’ve really seen acceptance of that reality. That said, it doesn’t happen automatically. That’s the work we do at Cause Strategy Partners — we help organizations get well outside of their existing network and find talented professionals at great companies with wonderful skill sets who are passionate about the organization’s mission. We train those board members, set high expectations, and set them up for a strong track record of success.

You have to work at it. You have to set a strategy. You have to design this. You have to find partners that can help you identify candidates. You can’t just rely on your own network of board members sitting in the boardroom today if you really want to build that kind of board.

Eric Ressler: I know that this is going to be a little bit of a tough question to generalize, but I’d like to try, at least for listeners who are trying to understand how they can have a more constructive board and a constructive approach to their board. What should fall, in your opinion and in your experience, generally speaking, in the board’s set of influence and oversight versus staff? Where do you see those lines being drawn in a healthy way?

Rob Acton: Great question. The CEO has a great amount of responsibility to lead and shepherd the day-to-day work of the organization. But in almost every aspect of responsibility, there’s a corollary board role.

Take strategy. The board cannot set strategy on their own — they don’t have enough information, don’t have day-to-day operational experience, aren’t working with clients on the ground. But we need that diversity of experience, insight, and wisdom brought to the strategy shaping process. So it’s a collaboration. The CEO brings reports, landscape analysis, competitor analysis, SWOT analysis built with the team — they’re providing core insight, but they’re not doing it alone. The board has an important role.

So they’re collaborating around strategy, around ensuring resources are coming into the organization, around ensuring those resources are being well-utilized and the strategic plan is coming to life, around making sure the organization has the right talent in key positions and can develop them in their positions.

In every element of this, there’s a “you do / we do / we do together” conversation. But you’ve got to define that upfront. You can’t just operate assuming that everyone intuitively knows “this is the CEO’s work, this is the board’s work.” You’ve got to talk about it.

Eric Ressler: In your experience, because you’ve worked with so many nonprofit organizations specifically on helping to place candidates for the board, what would you say from your purview is the general state of board and staff relationship right now? Are most nonprofits generally happy with their board but need a little bit of work? Are most nonprofits mostly dissatisfied with their board and see them more as an anchor than a force for good? What’s the benchmark right now? What’s the average?

Rob Acton: I can give a data point here that boards get a B minus to a C plus from their CEOs in terms of “do you have the right board in place to accomplish the mission?” That comes from BoardSource’s Leading with Impact, a biannual survey of governance in the nonprofit sector. So not a failing grade, not a D. A B minus.

There are a lot of organizations that come to us where the CEO is very unhappy with their board. They really don’t think that their board is getting the job done. That’s troubling. That actually makes me sad for that CEO and that organization, because it’s already a lonely job to run a nonprofit, but to have a board that doesn’t feel like your partners in mission but sort of an adversary — there’s definitely a lot of room for improvement across the vast majority of nonprofits we see.

That starts with who’s in the boardroom — designing the right board. But it also moves into training. I think nonprofit board service may be the most important responsibility that almost nobody ever gets trained for. In the workplace, you would never elevate somebody to a new role they’ve never been in before and provide no training. But we do that in the nonprofit boardroom all the time. I would venture to say less than 5% of all nonprofit board members serving in the country have ever received any governance training at all. Maybe they were onboarded to the organization — they saw the strategic plan, met the senior staff, toured the facility — but did they receive training in how to read financial reports? How to engage in fundraising efforts? Around strategic planning?

We just say “you’ll figure it out.” We can do better than that. At the very least, we should be regularly training our boards to perform the roles and responsibilities they take responsibility for when they step onto a board.

Eric Ressler: Where does the burden fall on that training? Should that be coming from the nonprofits? Should that be coming from the philanthropic sector at large? Should foundations be funding open source board training materials as a service to the sector? Is it a mix of all of those things? How do we fix that problem in your opinion?

Rob Acton: I’m trying to think of where the buck stops. The buck stops with the board itself. They typically have a governance committee who is charged with — most boards, I should say, that have broken off into committees have a governance, maybe it’s a governance and nominating committee — ensuring that good governance is happening at that organization. That’s the starting point for me.

At Cause Strategy Partners, we’ve placed 3,500 board members on 1,500 boards across the United States and United Kingdom. All of them have had access to good governance training at three or four stages in the process while we help them find their board. We’re not interested in placing folks on a board who don’t know the job, aren’t committed to excellence, and may not even show up.

I once had a CEO that I was on the board of an organization, and the CEO used to say, “Look, I’m going to take care of the day-to-day of the organization board. I need you to take care of yourselves.” That was sort of blunt, but also quite powerful for me. Why is Sharon needing to take care of 15 grown adults who are pretty solid professionals in their own right? Can you just take care of yourselves? Can you grow the board? Can you ensure that you meet your fundraising targets? Can you make sure that you get the training that you need? I think that’s a relatively fair comment. We can step up as a board and really ensure that we are operating at the level that we should.

Eric Ressler: So as we wrap up here, I know it’s been a big year in the social impact space. There’s been a lot of change. The landscape has changed rapidly. I imagine there’s been a lot of motion and turnover and change as it relates to nonprofits and their boards and their board chairs and all of that. Despite all of that, I’d be really curious to hear what are you seeing forward-looking, future-looking, that’s getting you really inspired right now, that’s helping you get up every day, even amongst things being really difficult, and feeling motivated to continue towards this work, to continue working in this sector. What are those things for you right now?

Rob Acton: High-capacity people like to deal with challenges. They don’t like to sit on boards that are rubber stamp boards where they attend four meetings a year, go to the gala, sell some tickets, and call it a day. High-capacity people are motivated when a complex challenge shows up and they need to sort something out in a manner that’s critical and timely, and they’ve got partners in that work.

If we have high-capacity people on boards that are trusting one another, communicating with each other, and working well together, there’s a different level of engagement. In the challenging environment we’ve been operating in, I have not seen the boards I’m connected to — any board members backing away and saying “this is getting hard, I didn’t sign up for this.”

An organization I’m involved with had to do substantial layoffs in the recent environment. I didn’t see any board members say “that’s not what I signed up for.” I saw board members lean in, strategize, want to solve these challenges and problems, and have very strategic discussions.

That’s what I’m inspired by. I think an environment like this actually creates the opportunity for us to engage high-capacity board members in a way they might not otherwise be engaged. And that sort of leadership will get us through the challenges we’re facing. I’m really genuinely inspired by that.

Rob Acton is the Founder and CEO of Cause Strategy Partners, where he’s placed over 3,000 board members across 1,500 nonprofit organizations. He’s the author of Becoming a Causey: Champion Your Cause Through Nonprofit Board Leadership. Learn more at causestrategypartners.com.

Eric Ressler is the Founder and Creative Director at Cosmic, a creative agency for nonprofits and mission-driven organizations. Learn more at designbycosmic.com.

I’ve been thinking a lot lately about what happens when you’re stuck running from crisis to crisis, when every day is about responding to the latest emergency, the latest headline, the latest trauma. You lose something fundamental. You lose the ability to imagine what could be different.

To explore this challenge more deeply, I wanted to talk with someone who’s dedicated his career to solving it.

Jamye Wooten has a name for this. He calls it reactivism, and he’s seen it up close. He was in Ferguson, he was in Baltimore after the murder of Freddie Gray. He watched the social impact sector move, as he puts it, from Black death to Black death, from hashtag to hashtag. And at some point he realized: if we keep this pace, we’ll always be in reactive mode and we’ll never actually build the future we say we want.

So Jamye stepped back from the front lines to create what he calls an imagination incubator. Through his work at CLLCTIVLY in Baltimore, he’s now serving over 200 social impact organizations. But he’s not just funding projects — he’s building infrastructure for imagination itself.

That means residencies that pay people $75,000 just to pause and create. Participatory grantmaking that values people over programs. Gatherings designed around remembering, reimagining and restoring.

Jamye’s proving that imagination isn’t some soft luxury we get to when things calm down. It’s the foundation. And when a sector stops imagining, it stops building anything worth reaching.

I’m Eric Ressler, and this is Designing Tomorrow. And now, my conversation with Jamye Wooten.

This interview has been edited and condensed for clarity.

Eric Ressler: Jamye Wooten, thank you so much for making time for me today.

Jamye Wooten: Alright, I’m glad to be here with you Eric.

Eric Ressler: So we were talking a little bit before we started recording about different ways you might kind of frame the show and some of the things that have been new with you since it’s been a while since we’ve connected. And the way I kind of want to start this is by teeing up a piece we just published just this Monday, at least when we were recording this. And the piece was really a reflection of mine around how to navigate what’s going on right now. I’ve been dealing with a lot in terms of how the sector has been shaped this year by a lot of the federal policies and the general kind of chaos and uncertainty in the space that’s had trickle down effects for us. And I’ve kind of developed a little bit of this like mantra, this North star for me around really making sure that when I show up each day, I’m focusing on the things that I actually personally have control and agency over and making sure that I’m making moves around those things instead of getting sucked up in the chaos, the uncertainty, the headlines, the negativity, which is real, it’s real, I don’t want to diminish that. And you were talking a little bit earlier about this idea of imagination, and I’d love if you could share your perspectives on how you’re thinking about all of that right now.

Jamye Wooten: We’ve been calling CLLCTIVLY an imagination incubator — a space for imagination. There’s a quote by Dr. Asa Hilliard: “When we ‘dream’ we often do not dream original dreams; we merely seek relief from pain.”

We serve over 200 social impact organizations here in Baltimore, and so often they’re starting with the pain, which is reasonable. They’re finding themselves in certain situations, but that pain often robs them of their imagination.

Years ago I wrote about something I called “Beyond Reactivism.” When I was thinking about starting CLLCTIVLY, it was: How do we move beyond reactivism? This was during the emergence of Black Lives Matter and state-sponsored violence, and we were going from hashtag to hashtag. From Black death to Black death.

I wanted to step back from the front lines. I was in Ferguson, I was here in Baltimore after the murder of Freddie Gray. I wanted to ask: How do we build more holistically? How do we dream and build the type of institutions that we want? If we keep this same pace of responding to every crisis, we’ll always be in reactivism mode.

We’ve been trying to create a container for imagination and provide space for folks to pause and imagine the future that they want to see.

Eric Ressler: I love that perspective. It connects to something I know deeply as a creative professional: my most creative ideas happen when I’m not working on them. When I’m away doing something else. The common saying of “shower thoughts” — I do a lot of thinking in the shower. I’ve been trying to walk more, get away from the screen, back into lived experience.

There’s a similar pattern in what you’re describing around imagination, but it requires space. And right now, space feels like a luxury when you’re stuck in reactivism or a true scarcity position — not just a scarcity mindset. How do we break that cycle?

In my opinion, a lot of the burden is on the funder side to provide resources for sabbaticals, for space, for true innovation and R&D in philanthropy. How do you think about the off-ramps from that cycle?

Jamye Wooten: You have to be really intentional about it. This year we hosted We Give Black, a three-day gathering. The theme was remembering, reimagining, and restoring. Remembering that we’ve been here before and that we have tools — what we call our ancestral intelligence. How do we go back into the ways we’ve always built community? Then, how do we reimagine from that what’s possible in this moment?

We’ve always had a residency program, but we made it public this year. We had over 250 applicants. All the fellows receive a $75,000 stipend to spend a year with us and work on a creative project. We currently have five residents.

I saw a video from one today about what it means to pause, particularly if you’ve been an entrepreneur or creative looking for the next gig, the next job, the next thing. To have a year where at least some of your basic bills are covered, you don’t have to hustle for the next gig. Most creative genius happens when we have a moment to do nothing.

It’s hard to deprogram yourself when you’ve been in grind hustle mode. We’ve been trying to be intentional about creating space and offering it to individuals and community so they can take a pause and be their best self.

Eric Ressler: I’d love to dig into how you think about designing and evaluating programs like that as a funder. My sense is that traditional institutional philanthropy focuses on outcomes — making sure investments are paying off and we’re making progress on important issues. There’s good faith behind that.

At the same time, I fear we get stuck in short-term outcomes and we’re not building toward sustainability for the organizations doing the boots-on-the-ground work. Organizations need things like overhead, sabbaticals, breaks, space for imaginative thinking, trying things they’re not sure will work. We need that to come up with new ideas.

Sure, there are proven solutions that lack funding and we should throw money at those. But we also need new solutions to problems we haven’t solved despite trying for decades. As a funder, how are you thinking about assessing success and figuring out who’s a good fit for grants?

Jamye Wooten: We start with impact. We start with organizations we know have done amazing work in the world. Often philanthropy invests in projects and programs, and we try to put people before projects and programs.

All of our grantmaking is participatory, so we have community advisory boards and review committees that come alongside us. We’re looking at maybe not traditional metrics. Like, do you have opportunity to rest? How are you collaborating and partnering with others in community? We really care about well-being.

I come from a family of entrepreneurs and lost my dad at 56 and my sister at 53. We know that while we may celebrate the hustle, the bootstrapping, the grind and resilience of community, it will also take you out.

We want to make sure our leaders who have often been pouring from an empty cup, often using their own personal resources to give back to community, that they have what they need.

Everybody deserves this sort of risk capital. We’ve been blessed to have the type of investment that allows us to try non-traditional programs. The outcome and response we receive from community has been a blessing. We want to make sure others have that same opportunity to say, “Can I just try this?” And that you can fail forward.

Everything’s not a failure. We’ve had some hiccups with things we would do differently. But the ability to try and the ability to imagine — we don’t want to snatch the dream away to where now you learn how to fill out a grant application just to serve the interests of philanthropy and you’re no longer imagining beyond that thing that first drew you to this work in the beginning.

Eric Ressler: I recently did a spotlight interview with Jen Nguyen of the Stupski Foundation, and I’m hearing parallels in how you’re both thinking about this. What are some ways you’d like to see the funder ecosystem and best practices change in a way that would better the social sector at large?

Jamye Wooten: Definitely more participatory trust-based models, allowing folks who are most impacted to be part of the decision-making process. Particularly even in this moment, we’ve really doubled down on individual donors.

Philanthropy, every three to five years, is creating a new priority and not necessarily giving organizations the runway they really need to build, grow, and sustain. If it was true in 2020 that Black-led organizations in particular were disinvested and underfunded, the same is true today. It didn’t take very long after the murder of George Floyd for funders to begin to say, “We are now shifting to other priorities.”

I would love to see foundations and funders make a long-term commitment to really bet like they want organizations to win, to give them the ability to scale and take the type of risks that they need. Most organizations we work with are going from year to year just trying to stay afloat.

I would love to see the type of investments, the multi-year commitments to organizations you believe in, to really fund them like you want them to win.

Eric Ressler: You have a background as an entrepreneur. You were raised in a family of entrepreneurs. I’ve been thinking about how investments happen in the corporate world — especially in the startup, VC-backed world — versus how it happens in philanthropy. We’re not comparing apples to apples, but despite all the deficiencies of the venture capital world, there’s this sense of placing a bet and really having a shared goal of that bet paying off.

The incentives might be because VCs want a 10X financial return. But my sense is there isn’t a similar feeling in the social impact sector traditionally. I think that’s where there’s a gap in risk capital and longer-term thinking. When you’re an investor in a VC world funding a two-person tech startup, you’re looking at the IPO 10 years out. There’s a pathway with multiple rounds of funding, gap funding, angel investors.

I don’t see a similar pipeline for the social impact sector. Does it exist and I’m just not aware of it? Or is there actually a deficiency?

Jamye Wooten: If it does exist, I’m not aware of it as well. Particularly serving Black-led organizations that are normally starting as one- to two-person operations with no funding available, now trying to build the relationship capital you need to even have a conversation with a funder, and normally not coming out with the type of investment that would allow you to scale.

We hear a lot of conversations about capacity and capacity building. I’m like, well, capital will help you build capacity. It was more trainings, more trainings, folks need more capacity building, more learnings. As opposed to: What does it mean to get the upfront capital that allows me to go hire my CFO and my CEO and my legal and begin to build out a team?

Most folks are building as they climb without this type of infrastructure. What we’ve tried to do in the last couple years with the launch of our fellowship is to pay the fellows a $2,000-a-month stipend as they travel along with us and help them build out their business model and provide intentional space for them to really grow and build their work.

But I think often we’re not — it’s training after training without the type of capital that allows organizations really to thrive. And then we say, “See, you need more capacity.”

Eric Ressler: I love that point. The term “capacity building” can be such a misnomer because what’s the number one lever we have to build capacity? It’s funding. Funding unlocks capacity. It unlocks the ability to hire, to train, to have space. All of that is capacity.

There’s no point in learning if you don’t have space or time to learn. There’s no point in training if you don’t have space and time to absorb it or put it into practice. What I see on the front lines is that organizations are lacking capacity, but that’s a symptom of a deeper problem: lacking the funding and resources they actually need.

I want to talk about the current state of work focused on liberation, DEI — there’s a whole spectrum here. Circa 2020 through 2022, there was an upsurge because of the cultural tide shifting. Now there’s been political backlash from many different points of view — ignorance, misinformation, bad faith actors. Philanthropy, especially corporate philanthropy, seems almost relieved to get back to business as usual, which is a travesty.

How has that been for you and the organizations you serve?

Jamye Wooten: It’s been tough. Particularly for organizations that have relied on federal grantmaking and funding over the years, to have that snatched overnight is a major impact.

For us, that just hasn’t been our model. Our model has been: How do you build a revenue base as you do this work? How do we develop individual relationships with donors to sustain this work?

It’s clear when you’re trying to do liberatory work that these attacks will come. I’m always planning for these moments, whether it’s a Trump moment or this DEI moment. History shows us that when you’re beginning to make a certain level of progress, there will be a snapback.

It’s about being able to prepare in such a way that says: How do we build sustainable organizations in the midst of this work?

I think it’s telling about who are our real partners, who really are our friends and allies in this moment. For me, it’s refreshing to see those who are doubling down and understand they’re just as committed as they were before. And then to see those who are fly-by-night — when the moment is high and it’s whatever issue, whether it be the Black community, LGBT community, environment, whatever it is, how they move with the wind versus those who are committed because of their values and see each other as human and what we want to do to make a difference in this world.

Eric Ressler: Talk to me about your model and this philosophy of building in earned revenue, which isn’t always possible for all types of organizations. There’s common advice that you should have a diversified portfolio of funders. But there’s also research published in Stanford Social Innovation Review showing that a lot of organizations who’ve been successful have largely gotten really good at one, maybe two particular fundraising methodologies.

It doesn’t seem like trusting the federal government to fund social work is a good bet right now, especially if you’re doing anything progressive or DEI-focused. We’re seeing organizations shift to individual major donors who are value-aligned. How are you thinking about that as both a funder and an organization that has to fundraise to generate resources?

Jamye Wooten: Definitely doubling down on individual donors and relationships. A couple years ago I thought about: Do we scale wide or scale deep? We landed on scaling deep and really being intentional about building relationships here locally. It’s worked well.

We’re coming off Collective Give, our annual day of giving to support Black-led social change organizations in Baltimore. It launched in 2019 and raised about $5,000 in 24 hours. We just raised $1.2 million this summer in 24 hours — our third year over a million dollars.

I believe in crowdfunding. I believe in individual donors, really cultivating those relationships so that we aren’t — I often walk into philanthropy and say “partnership, not paternalism.” From the beginning I’m like: How do we partner? How do you see us as a valued partner? Invest with us for the long haul.

Some say we don’t, and we keep it moving. Then there are those who have stuck around. I think about 67% of philanthropy is individual donors, so looking at that large pool of individual donors using their personal wealth to give back to community.

We’re also on the cusp of launching a new campaign called the Power of One, something I did years ago. It’s a dollar-based campaign. It really says that everyone has an entry point into philanthropy, into giving their time, talent and treasure.

For me, it’s really doubling down on individual donors and doing that work. We’ll be launching a new platform later this fall which is revenue-based, so the donor fees that everybody else is charging us right now — we’ll use some of that 3%, but it’s regenerative in the sense that those funds help us grantmake and continue to do the work back in community.

Eric Ressler: You’ve gone from a $5,000 day to an over $1 million day in a short amount of time through individual donors. What have you learned about that modality that’s important? You say it’s relationship-based. What does it actually look like in practice?

Jamye Wooten: We started a process, a liberatory process, where we go through our virtues, our values, the history of philanthropy, how even some received their wealth through extraction. What does it really look like to be in relationship and see each other as humans?

In 2018 I participated in Old Money New Systems. It was a gathering of individuals of high net worth, folks in nonprofit space, activists coming together to reimagine what philanthropy could look like. We went through a similar process of healing, looking at the historical implications of philanthropy, and then building something new, which was a fund.

Individuals of high net worth said, “This is the first time I’ve been in a space where I felt like I didn’t have a dollar sign on my head.” One of the things I realized was that we all have needs. Sometimes there’s this power imbalance in philanthropy. What does it mean to remove that power imbalance and begin to have just human conversations?

In our first fund, everyone could ask. Individuals of high net worth couldn’t ask for money, but they might say, “Jamye, can I have an hour of your time? I want to learn more about this.” Or, “If you’re in Baltimore, you need an extra room, I have a room you can stay in.” Ways in which we create an exchange so it’s not always that power balance or seen as just one-way exchange of giving.

It’s worked well. Over the years it’s been tears, it’s been people walking away and coming back. But for the most part folks have stayed the journey to do the tough work.

I think, again, relationships and doubling down on being honest and truthful about these moments that we find ourselves in, willing to wrestle with certain ideas, but ultimately thinking about what it means to be human and give back to community.

Eric Ressler: This year has been especially challenging for organizations who are justice-oriented, who are trying to create social change, who feel like there’s been major setbacks, especially here in America. I’m curious what you’re seeing right now that’s inspiring or defying this moment despite the challenges and friction.

Jamye Wooten: I think this theme of imagination is not just ours. I think it’s in the air. The beauty of that is even in these moments, people reclaiming their joy, reclaiming time, reclaiming space, deciding how they’re going to live in this moment.

I see less of what I would call reactivism. I think it’s there and we have to react and respond to these moments. But I see people being a lot more intentional about their time, their space, their joy, and creating the world that they want.

I’m excited about what I see emerging. I see our residents who are creating new songs and using animation to tell stories. I’m excited about what people are working on and that their joy and their purpose is not being robbed by this moment.

Eric Ressler: I think it’s really important, but it’s also really hard for a lot of people. It’s not something that’s going to come naturally. It’s a muscle that you have to have the space for, but you have to put the energy into it as well.

Jamye Wooten: Part of the design community — it’s all around sacred memory and imagining. These are very heady people. So it took a moment. One of the things we did was watercoloring. We do a lot of things to say: How do you get out of head and more into heart? Because it is hard, even when you have space, to get back into that imaginative space. We’ve been really trying to say: What does it mean to really slow down when folks are very heady and often that’s where their superpower is — to go back into being?

Eric Ressler: This hits really close to home for me. I’m definitely one of those people that tends to live in my head. My brain’s going 24/7, especially as I’m trying to solve problems. It’s a superpower, but it’s also a huge deficit if it’s not controlled.

I’ve found I need those moments of embodiment — whatever term you want to use. For me, that’s music. For me, that’s exercise. I know if I don’t do enough of those things consistently, even if I don’t feel like I have the energy for it, ultimately it’s just not helpful.

For a long time at Cosmic, we’ve had a four-day work week where we have Fridays off. This year’s been a little different — we’ve had to buckle up and put our head to the grindstone a bit more, largely in service to our clients who need extra support right now. That’s been hard in some ways, but in other ways it’s been refreshing. It’s taking me back to the early days of starting the organization, that entrepreneurial experimental learning-based mindset.

This year’s really tested me personally and my team on that. But I’m picking up on the vibe you’re describing, which is this sense of intentionality. Everyone’s being forced in this cultural moment to figure out: How do I show up? How do I show up best? What do I focus on? What do I let go of?

I’ve been hearing this from interviews on this show — everyone’s got to find that thing that re-energizes them. There’s been a lot of talk about self-care, but it’s just: What’s your humanity? What makes you feel most alive and most human and making sure you’re carving out space for that?

I challenge everyone listening who says they don’t have space for that to look at their screen time report every week and figure out how much of that time could I be giving up for other things instead? I don’t mean that in a judgmental way — I’m very guilty of this myself.

What is that for you? What keeps you lit up? What keeps you energized? Obviously the work you’re doing is important, meaningful, substantial. But even outside of that, what are those things for you?

Jamye Wooten: Our facilitator at our retreat last week said, “The times are urgent, we must slow down.” It’s beautiful, particularly in the way in which I can go.

We’ve carved out focus weeks and other things that we implement in this work. It calls me as well. I have to do better at my own pacing. I can stay on the grind because I really love this work.

But I try to spend as much time by the water as I can. To your point earlier, I realized some of my greatest ideas and inspiration comes through the slow down. I try to catch myself when I realize sometimes I have been busy without being productive. I could have shut down two hours ago. I was just scrolling the last two hours. Why am I even at my office as opposed to home?

That was a piece too where I’m at home and it’s 7, it’s 8, and the kids are like, “Are we eating tonight?” My son just came back from Brazil two weeks ago. I’m sitting there with him on the bed and he said — he’s 14, I’m homeschooling him — he said, “Dad, you’re so close, but so far.”

Man. You think you’re doing something — I’m homeschooling, I’m physically present, but I wasn’t emotionally present.

So what does it mean to create those boundaries to slow down for family that sees you doing work in the world? And it’s hard for me to get your attention in this moment.

I can’t tell you that I have the balance in that. This work calls me, I love it, but I am definitely trying to be more intentional between home and work. What does it mean to come into the office, and when I come home, we’re not going back to work? I could do this work night in and night out.

I think it gives me great joy to see — what we hear often from the organizations is “Thanks for seeing me.” Even more than the grant, it’s the acknowledgment of their humanity that they’ve been here, they’ve been in community, they’ve been working tirelessly to serve. And “Thanks for seeing me.”

It’s such a great currency. I just have to make sure — I think I’m doing a decent job, but I want to make sure if my children aren’t saying that, then something’s out of whack. My son saying that to me was definitely saying, “Okay, I heard you and I got to make sure I’m being more intentional at home as well.”

Eric Ressler: Kids have a way of just really cutting deep in those ways, being so clear-eyed about it. And yeah, I think it is hard to just shut down sometimes, especially when you’re doing important work. It’s different than, say, working in a cabinet shop where you come home and you might be thinking about cabinets still at some level — and I’m not here to diminish cabinet makers, in some ways I’m kind of jealous of that setup.

But the kind of work you do, and I think it’s similar for me, I could spin on this 24/7 and I love it and I believe in it. At the same time, showing up more for your friends, for your family, and knowing how to turn it off — your brain’s still going to do it, even if you turn it off, even if you are emotionally present. In the background, I believe your brain’s still working on solving those problems, even if they’re subconscious.

I completely relate to that and I’ve been trying to work on that myself, oftentimes failing at doing so. When I come in after a day where I didn’t get the things done that I needed to or hoped to, it can be especially hard to shut off on those days. But I’ve also found that when I do, I’m more effective overall. I’m more able to show up at my best when I do show up at work.

It’s a constant tuning. It’s not something you fix and you’re done with. You have to be constantly intentional about it.

Eric Ressler: Before we wrap up, how can people get in touch with you? How can they follow you? Is there anything you want to promote?

Jamye Wooten: We’re CLLCTIVLY at C-L-L-C-T-I-V-L-Y on all social media. That’s the website.

I’m excited about our new platform. I think our current way of being, we can be as an organization the bottleneck. The new platform will allow changemakers and donors and community members all to be on the same platform and to build community as well. That should launch early October.

The last few years we’ve hosted 28 Days of Black Futures. That’s every February for Black History Month. The year before last we did the Black Futures Cypher where it’s a new artist dropping every day. We’ll do that again this February. It was an amazing digital media campaign that won a few awards. So look out for that as well.

I just recently came back from South Africa where we’re looking at building a global impact house. Believing in place, but what does it look like to partner with other folks around the world? So excited about what the future of partnering around the world and doing this work looks like.

Eric Ressler: Awesome. I feel like we could do an episode on each of those things, but for today we’ll wrap it up. Thank you again for your time. This was great.

Jamye Wooten: Thanks so much. It was beautiful. Appreciate you.

This interview has been edited and condensed for clarity.

There’s a number that keeps showing up in conversations about American philanthropy. And it tells two completely different stories depending on how you read it.

Over the past decade, charitable giving from affluent households increased more than 30%. That’s remarkable. That suggests a sector that’s thriving. Resilient. Responding to need.

But here’s the other story that same data tells.

Donor participation dropped from 91% to 81%. Twenty million American households stopped giving to charity entirely. First-time donor retention? Below 20%.

Fewer people are writing checks. They’re just writing much bigger ones.

So which story matters more? The one about record-breaking totals? Or the one about democratic participation collapsing?

To answer that question, I wanted to talk with the researchers who created the data in the first place.

Amir Pasic is the Dean of Indiana University’s Lilly Family School of Philanthropy. It’s the world’s first and only school devoted entirely to the study of generosity. He oversees Giving USA — the longest-running report on American charitable giving.

Bill Jarvis is the Managing Director at Bank of America Private Bank. He’s spent nearly two decades tracking how wealthy Americans give through the Bank of America Study of Philanthropy. He bridges wealth management and charitable giving in ways few others can.

Together, they’ve surveyed over 15,000 affluent households since 2006. Their 2025 findings reveal a sector at a crossroads.

And that crossroads is exactly what we’re exploring today.

This interview has been edited for brevity and clarity.

Eric Ressler: Amir, this study has a lot of really interesting takeaways. As someone who’s been in the philanthropic space studying it as an academic for a really long time, what were the most striking things that you took away from this report?

Amir Pasic: This is a very valuable report, the Bank of America Study of Philanthropy. We’ve had a partnership with Bank of America since 2006, surveying high net worth individuals or affluent families and their behaviors, which are so vital for the health of our nonprofit sector. The continuation of this is in itself a remarkable resource for nonprofits and donors in the field.

In the most recent study, the 2025 study, we saw a significant increase in giving by high net worth donors. The average gift has gone up significantly, which is reflected in other studies that confirm that as well. We have seen a decrease in participation, however, in terms of the number of affluent donors who are giving, and that reflects a broader trend as well.

I think it’s really important to pause and focus on the top line. The average gift increased from 2015 when it was just over $25,000 to over $33,000 in 2024. So that is a remarkable increase. The other caution is that there was a decrease in participation of how many high net worth affluent donors have given from 91% in 2015 to 81% in 2025. So this reflects something of a broader trend we see across our society where we have the dollars up, but the number of donors down.

Eric: Bill, what were some of your takeaways?

Bill Jarvis: The dollars in fact are up. What’s more important though is that in inflation-adjusted terms, the dollars are at least constant. What we’re seeing here on the part of this group of affluent donors is that they are keeping pace with inflation. In other words, the real value of what they’re doing is being maintained. That’s very important because we’ve been through this burst of high inflation.

It is true that the donor participation, the incidence of donation in this study is down. But that also is consistent with Amir’s large social giving study called Giving USA, which comes out annually. That’s the study of mass giving in this country. If you look back to the beginning of this century, the population of Americans pursued this very broad model of donating. Two-thirds of American households taken as a whole were giving to charity. By 2020, and other surveys show that was now less than half in terms of the incidence of giving, the participation in giving. The inflection point was the global financial crisis, which damaged average household balance sheets from which they have not recovered and did not recover.

So what this means is that if you are listening to this podcast, you are fated, you are condemned to rely on this small group—what we would call the top 5% of the population in terms of assets and income. But the trigger, the asterisk there is that although they are the ones who are giving more and more at the top of this pyramid, they don’t like to be alone. They don’t want to be the people who are just by themselves.

So if you’re listening and you’re in development, or if you’re in a nonprofit that’s trying to raise funds, part of the other part that you’re condemned to, in addition to seeking monies from this top group, is to create breadth in your donor pool to the point where even the so-called—I mean, it’s a commercial term that’s become applied to fundraising—the return on investment for that more modest gift may be relatively small, but you have to build that base in order to get those higher net worth donors to be there and make those gifts for you.

Eric: Bill, I think that’s a really important point that I see a lot of the clients that we work with miss. They look at what I call retail donors as something that you either choose to go that way or you choose to go the high net worth route. And I think that is a mistake because the high net worth donors want to see broad support and momentum.

Bill: Yeah, and it’s a false dichotomy, and here’s why. Our anecdotal information, and I’m sure some of Amir’s research also tells us this—we read in the newspapers, usually several times a year, about charities who receive bequests or who receive extraordinary donations from people that they either didn’t know or they knew only tangentially or who were small donors or who were just volunteers and small donors.

As they approach the end of their lives, these people say, this is what I want my legacy to be. This is what I want to be remembered for. And here comes this relatively substantial bequest. So you just don’t know. If all you’re doing is focusing on the people who are visibly affluent or wealthy, you’re missing that opportunity to cultivate these other people of modest means.

The donor of modest means or the everyday donor is important. There are extraordinary donors hiding in that group and also taken as a whole, your gift of $50, $100, $250—if you add these up, they do make a difference.

Eric: I want to touch on something potentially a little bit complex, which is that my takeaway from this study was a little bit of a double-edged sword. There’s definitely some positive news here. We’re seeing the absolute number of philanthropy increase, even in relation to inflation. But we’re also seeing that concentration. To me, that feels like a result of growing income inequality in America and broadly as well. What I worry about is that more and more returns to this almost Gilded Age style of philanthropy, which we all know is not sustainable. I’m seeing it on the front lines with the clients that we work with where they’re struggling right now. We have a lot of funding down largely from the fallout of the federal administration policy change that’s happened this year.

Amir: This is a very good question, and it goes to a lot of the core issues that we’re facing. The concentration issue is part of the broader societal challenge. Where did all that wealth come from? Is it equitably distributed? And how can we as a society look at this issue? Those are very good questions.

But the issue of generosity, caring for each other, and giving is such a fundamental part of the human condition. It is built into our humanity, built into the way we organize ourselves as families, as communities. We’ve seen it throughout history, and we’ve seen it even as wealth has grown more or less evenly distributed.

The research that we’ve conducted over the years shows that lower-income individuals give a higher proportion of their assets than wealthier individuals. So even as there are inequities in our society and inequality in our society, there’s still that impulse to care for each other. That is fundamental, and that’s something that we should always harken back to.

Now, when we think about this concentration of wealth, it also gives us a clue about where change can be made. If you had to change the mind of 100 million people versus 100 people, which would be easier? In some sense, this concentration of resources means there’s an opportunity for influencing change at a very significant level. That’s not the goal for everyone, but for those who think about advocacy and changing social systems, it does provide a different pathway.

Bill: I want to take us to another part of the study, which I think is really important and actually one of the most encouraging findings, which is the extraordinary bounceback in volunteering among affluent Americans. It was 30% at the low in the pandemic where people were nervous, didn’t want to do it. And now it is 43%. We estimate the average volunteer contributed 120 hours to two organizations.

Why does this matter? Because our data shows that volunteers give two and a half times more than non-volunteers. We’ve tested that, and it’s significant to the 99% confidence level. So volunteering is the gateway to philanthropy. When you give your time, you have an opportunity to really understand the organization, to understand what they’re doing, to understand their priorities, to assess their effectiveness. You can also assess whether the organization’s values are aligned with your values. And then you have a much better, more intimate understanding of whether you want to be supportive or not.

Eric: That’s a really, really important data point. Because I would have thought that folks who have achieved a significant amount of financial means would be too busy to volunteer, right? They don’t have time.

Bill: This comes back to that idea that humans are social creatures. We’re wired for this. This is not exceptional behavior.

Amir: Absolutely. We sometimes think that self-interest is the only motivation that people have, but the research is overwhelming that generosity is built into our nature. It’s essential to how we survive as a species. We see volunteering as an expression of that, and it cuts across all income levels and all sectors of society.

Eric: I’d love to hear you talk a bit about generational differences in giving and how Millennials and Gen Z are different from their parents. What are you finding?

Bill: Gen X and Millennials are now two-thirds of affluent donors, so they predominate. We’re also seeing the rise of Gen Z donors. For organizations that exist today, this matters a lot because younger donors prioritize issues over organizations. It really doesn’t matter if you have a very strong established brand. You have to turn that inside out and lead with what you do and why what you do is important and then attach your brand to that. You’re having to reintroduce yourself to this next-generation donor.

Other things that we see about younger donors—they’re more interested in online giving and being involved in social media. They talk about their philanthropy more. Forty-two percent of younger donors associate their names with gifts, whereas 31% of older donors do, and 69% of older donors give anonymously.

Amir: There’s an extraordinary change that’s going to take place. One of the things we learned from this Bank of America study is the great wealth transfer—$84 trillion over the next 30 years—which is the largest intergenerational wealth shift that we’ve ever seen. Only 13% of affluent respondents involve children, grandchildren or younger relatives in their giving decisions. This is a catastrophic disconnect.

If nonprofits are not soliciting and cultivating the pipeline of donors who are giving less, then they’re abandoning the future by just focusing on where the money is right now. You have to be asking about both. How do we preserve what we have today and build for what we need in 20 or 30 years? That’s the real challenge for nonprofits.

Eric: Can you talk a bit about donor-advised funds and how we should be thinking about them?

Bill: Twenty-four percent of affluent households use a DAF, a charitable trust, or a private foundation. Among those with $5 to $20 million in assets, 48% either have or plan to have a giving vehicle within three years. Structured giving represented 18% of donations in 2024, nearly double from 11% in 2015.

These vehicles enable donors to give with greater intentionality. They can set up the vehicle, make the gift, get the tax deduction in that year, and then take time to thoughtfully decide which organizations to support. The benefit is it enables that kind of thoughtful giving.

Amir: There are debates about DAFs. The criticism is that some donors get the tax benefit immediately but the money sits there indefinitely. But as Bill says, the evidence shows they actually pay out at higher rates than foundations. On average, DAFs are paying out at 20 to 24%, which is much higher than the 5% minimum for foundations.

Eric: One other thing that really stood out to me in the study is that nonprofits are actually the most trusted institution when it comes to solving problems. That feels pretty significant.

Bill: Year after year in our study, when we ask what confidence people have in societal institutions to solve problems, large and small companies, the branches of government and so on are really pretty much at the bottom. Who is at the top? Nonprofit organizations, individuals, and very importantly, future arising generations.

This is the opportunity in the society that we live in, but it’s important for us to recognize that that exists and to take that responsibility happily. There are some societies in the world where individuals do not have this ability to make a difference and are constrained by law, by power structures, by social practice from doing those things which we can do here.

Eric: That’s really powerful. As we start to wrap up here, I want to leave each of you with a double-ended question at the end. One is one major piece of advice or guiding philosophy for executive directors, development directors, folks who are out there who need resources and support for the good work that they’re doing. How should they be thinking about where we are and where we’re going? And secondly, what are you most inspired, motivated, and activated about right now in this current landscape despite some of the setbacks that the sector has seen? Amir, I’ll start with you.

Amir: I think generosity and giving are such an important part of society. In a time when so much is up in the air and being changed in front of our eyes, the title of your podcast comes to mind. We are designing tomorrow through the voluntary and generous actions of our population. This is really the antidote in many ways to the polarization, the enmity, the distress of coercion that we feel internationally, nationally.

The great American tradition that Alexis de Tocqueville recognized in the 19th century when he came here—people binding together, getting together in innovative ways, not waiting for somebody in authority to come and help them out and tell them what to do. This is the core of the dynamism of American society. The executive directors of nonprofits are really the leading edge of this in many ways, trying to redefine for communities how they stand and how they’re going to deal with where we’re going next.

So I think that is the depth of the mission, the importance of the mission. You always come back to that when you’re running a mission-driven organization, whether it’s formally a nonprofit or whether it’s a social enterprise or even if you’re working in a quasi-governmental entity that is dealing with the community. Always come back to mission.

If your mission is no longer relevant, then we do also have opportunities to say, we can’t do our mission, let’s start something else. So don’t stick with a mission that doesn’t have a relevance for today. We’re not in the business of continuing organizations just to survive with the organization. Always come back to the mission. How is it relevant to where the world is going? How can we help move and design tomorrow?

The second part of the question is what gives me hope and inspiration. I’m at a university where we deal with young people on a daily basis. You have to have faith in the future when you see young people curious and ambitious about the possibilities in front of them. That is both the greatest opportunity, but also our greatest challenge when we have young people who don’t see that opportunity. So those of us with gray hair, that is our responsibility to make sure that they see that the world is in their hands and they are the ones who are designing tomorrow.

Eric: That’s beautiful. Thanks, Amir. Bill, I’ll let you weigh in too.

Bill: Designing tomorrow, Amir, you’ve been with us on the mountaintop here. I’m going to take us down to a little more implementation. I have two recommendations to our audience.

One is to make a strategic investment in development and advancement. This is very important. In so many cases, in too many cases perhaps, we see nonprofits that think they can just hire a consultant to do a campaign, or they think they can just have one part-time person doing it. If you look at the organizations that are successful at fundraising, first of all, it is glued to their strategic plan. The strategic plan has a three or five-year trajectory. There are things that you want to continue doing, things that you’re not doing that you want to start, things that you’re doing you want to do more of. Each of those has a price tag. And for each of those price tags, there is a principled source of funds.

You have to think through whether it be membership, annual giving, the gala, things like that—how are you going to get these monies? This is where strategic fundraising comes in. And that then gets embodied in the things we’ve been talking about, in volunteering, in cultivating the donors, enabling them to think that the organization is aligned with their values and so on and so forth.

The second point that I would say in terms of advice is I would like to make the case for endowment. Now, many people think endowments are only for rich organizations, but endowment is a kind of capital for a nonprofit. It speaks of stability. It frees you from the vicissitudes of having to worry about annual giving. It also, if you have donors who are visionary enough, enables you to endow the key offices of the nonprofit in a way that will enable you to hire people who are just as good as that visionary implementer that you’ve got in that place right now. So that also begins to give you stability.

I do believe that strategic investment in development and also thinking strategically about endowment and the role that it could play in achieving that stability for the organization—its ability to lift its head above the turmoil of the day-to-day and to think more about the future.

In terms of what gives me encouragement, I echo what Amir said. One of the questions that we ask in the study is what confidence do you have in societal institutions to solve problems? And as you can imagine, consistently year after year, large and small companies, the branches of government and so on are really pretty much at the bottom. Who is at the top? Nonprofit organizations, individuals, and very importantly, future arising generations.

This is the opportunity in society that we live in, but it’s important for us to recognize that that exists and to take that responsibility happily. There are some societies in the world where individuals do not have this ability to make a difference and are constrained by law, by power structures, by social practice from doing those things which we can do here. So I would say it’s an encouragement. Thank you, Amir, for taking us to that mountaintop to think about again, forming that future, designing that future.

We’ve known the facts about climate change for decades. The science is settled, the data is clear, the solutions exist, but the problem isn’t a lack of information. The data has been modeled, graphed and discussed since I was a young student watching Bill Nye, the Science Guy in the nineties. So why hasn’t that knowledge translated into action more and more? I think the problem is how we’ve been trying to teach it, to message it, to contextualize it.

There’s a story that stuck with me from my conversation today. A kid who loved potato chips, but when asked to trace them back to their source, he couldn’t get out of the factory. The idea that his favorite snack started as a tuber in the ground covered in dirt was completely foreign to him. If a child doesn’t understand where their food comes from, how can we expect them to grasp the complex systems that govern climate, ecosystems, or community resilience?

Facts don’t change minds. Lived experience does. Connection does. Belief does.

To explore what that looks like in practice, I wanted to talk with someone who’s been proving this theory for over two decades. Drew Dumsch is the President and CEO of the Ecology School at River Bend Farm in Maine. He co-founded the organization 26 years ago with a radical idea that ecological literacy is foundational to creating engaged, compassionate citizens. He’s built a solar powered campus that models regenerative living, helped pass bipartisan legislation for outdoor education, and leads a network proving that education isn’t just about memorizing facts, it’s about understanding how the world actually works and our place within it.

Full Interview

This interview has been edited and condensed for clarity.

Eric Ressler: Let’s start with where you are right now. What’s it been like this year leading an environmental education organization?

Drew Dumsch: We’re an environmental living and learning center here in Saco, Maine. We bring people to our 313-acre farm to experience systems thinking and experiential education—conservation, regenerative farming, social-emotional wellness, environmental justice, climate action, food security. Everything I just listed is under attack right now. I don’t think there’s one thing that doesn’t feel like it’s at some level a little bit under attack.

We had a USDA grant that was frozen, then unfrozen. We were going to host a national conference called Women of the Water—women scientists doing aquaculture work funded through NOAA and Sea Grant—and they had to drop out. We’re also seeing the impact of the Canadian tourism boycott. Last month alone, we saw at least a 30% drop in tourism because a lot of our summer tourists come from Canada.

The need is there, but the funding—whether federal, state, or even foundations—there’s a lot of shifting. Trying to keep up with that is interesting, to say the least.

Eric Ressler: So how are you thinking about sustainability in this moment — not just environmental sustainability, but organizational sustainability?

Drew Dumsch: Having our own site has been transformative. We can convene the important work of environmental justice, climate action, food security, and conservation. We have 172 beds, five miles of trails, and we’re becoming a place where people doing this work can meet in an environment that embodies the work itself.

Our role as a convener is going to help us get through this. We can’t do this work alone, and we don’t want to. Fifteen years ago, we founded what’s now called the Maine Outdoor School for All network—a partnership of outdoor schools. This spring we got the Outdoor School for All Maine Students bill passed. It went 34 to 0 in the Maine Senate, completely unanimous. Then in the House, it passed 113 to 1. The fact that we could take something like getting kids outside and spending time at a place like ours that’s modeling climate action and farming, and get that level of bipartisan support, is encouraging.

The challenge is they gave us a $500 fiscal note after passing it. So we’re trying to figure out the funding part, but that kind of network power and collaborative power is going to mean more than ever.

I think about this almost every day as a father of two daughters: We’re all seeing the impacts of climate change in our lived experience—flooding, wildfires, heat waves. The science is clear. There’s consensus this is urgent. Yet policy doesn’t seem to keep up with the science. As someone in environmental education, what’s your theory of change?

Drew Dumsch: Being told facts is not the purpose of education. Facts are part of becoming a well-rounded human being and an engaged citizen, but I think a huge gap is that as a society, we lack the ability to understand systems.

Here’s a great example from early in my career. I’d do a food systems activity where kids would pick their favorite food item and trace it back to its source. I had a kid who loved potato chips. I could not get that kid out of the factory. The idea that his beautiful potato chip started as a tuber in the ground covered in dirt was reprehensible to him. As much as I like taking kids out into the forest or to tide pools, if I’m not doing a heavy dose of food systems education, I’m missing a huge part of that.

Teaching people the complexities of a system through simple, repeated, enjoyable experiences is what we’re about. Teaching how the world works, how ecosystems like a forest or a tide pool function when they’re healthy. We can take that to be less impactful as humans and more regenerative.

Eric Ressler: Talk to me about this idea of regenerative principles beyond just agriculture.

Drew Dumsch: I’ve recently embraced applying regenerative agriculture principles to leadership. The Living Building Challenge dorm and dining commons here are examples of regenerative design, but I’m really interested in regenerative learning—creating learning systems and communities based around how a healthy ecosystem functions. We’re trying to mimic more of nature instead of fighting it with herbicides and pesticides. What if we do organic? What if we do permaculture?

The wonderful opportunity is giving kids and adults experiences where they pick an apple from a tree, maybe cook that apple, see the sunrise over the river. These experiences, linking to bigger systems and community dynamics, are powerful because we can’t talk our way out of this and we can’t be told our way out of this. Sure, there’s plenty of education about climate change happening. But going back to learning theory, that’s just not how most people learn. Some people like you and I might pick up a policy paper on climate change, but so few people do that.

Eric Ressler: You mentioned this idea of norming experiences. What does that mean in practice?

Drew Dumsch: One thing we do at the Ecology School is give an enjoyable week-long experience living and learning together, and you’re norming things like eating farm-fresh food and being compassionate with each other. That’s really come to the forefront, especially in the last few months. There is no place for casual cruelty at all. Unfortunately, we’re seeing at very high levels constant casual cruelty.

I think one thing we do really well is model compassion — compassion for each other, compassion for the earth. I’ve got a great colleague, John DiGregorio, who’s the education director at the Great Smokies Institute down in Tennessee. We were hanging out one time and he said, “You know what we do in our sites really well? We do kindness.” That stuck with me.

Eric Ressler: That’s a powerful frame. You could create sustainability through other means, couldn’t you?

Drew Dumsch: You could create sustainability through fascism and cruelty. It may be sustainable, but is that a vibrant community you want to live in? You could force everyone to do solar power and electric cars—I don’t think that’s what we want, though we know that’s the smart solution.

There’s a really great book called The Triple Focus by Daniel Goleman, who did the social-emotional intelligence work, and Peter Senge, who’s the guru of systems thinking. They said basically the education of the future is just three things: understanding of self, understanding of others, and understanding of systems. If you can get that right, you’re going to have an amazing society.

Eric Ressler: You’ve talked about this idea of ecological literacy. What does that mean?

Drew Dumsch: Just as you learn your ABCs so you can read, if you learn what we call the ABCs of ecology, you can learn to read the landscape. It’s all about ecological literacy. If you’re illiterate, you can’t read. How can you be a fully functioning member of society? If you are ecologically literate, it brings a whole other level to your ability to understand the world and to walk within the world with intention and compassion.

When I started the Ecology School with my friends and colleagues Steve Siegel and Brad Bradway, we started with that level of intentionality. I’ve been at other centers where you get the kids out in the redwoods, do a tide pool, but there wasn’t that underpinning of why we’re doing this.

Eric Ressler: There seems to be a major schism between what people care about and their feeling of being able to do anything about it. How do we bridge that gap?

Drew Dumsch: Teenagers and young adults — the level of depression and anxiety is striking. Hope is based on both understanding of what can be and then agency to be a part of that. What we’re trying to do by grounding people in lived experience at River Bend Farm is start where people are, not where you want them to be.

There’s often with climate action this all-or-nothing mindset. If you’re not solar, if your house isn’t solar powered and you’re driving an electric car, you suck. But having a handful of people go super passive solar house, solar powered, electric car, versus a lot of people even taking a basic step like turning down their air conditioner or buying more local food—there’s impact there. The motivational force of change can happen when you’re modeling that.

Here at Riverbend, we’re reimagining the future now, not waiting. We often get these utopian visions: we’re just going to have solid-state batteries and carbon scrubbers, and it’s always about technology 10 or 20 years down the line. But we know right now that we have what we need to radically lower carbon and feed more people. It’s all about these little things. Multiple simple, enjoyable, inspirational, awe-inspiring experiences add up to some greater whole where you become more attached and connected to your community—not just the human community, but the world community, the natural community, the environment.

Eric Ressler: I think we often want simple solutions to climate change, but the reality requires multiple approaches.

Drew Dumsch: The wonderful thing is using food systems as an overarching lens. We knew we wanted a farm because applying ecological principles to growing food—that’s agroecology. If you get agroecology right, it’s a systemic and holistic approach. You create resilient communities, help address food insecurity, localize the economy. Agriculture is a huge driver of climate change, so getting agriculture right means you’re addressing climate change.

People want the simple solution. That’s boring. I think the level of diversity in solutions is exciting and creative. It’s such an opening for people to engage that there isn’t just one monolithic solution. We will all do this and the world will be better. It’s going to take multiple solutions. I know that’s hard for some people to embrace.

Eric Ressler: What’s giving you hope right now?

Drew Dumsch: My wife came up with this term because it’s definitely been hard — she used the word “demoralizing,” and I’m like, that’s it. I am demoralized. At the same time, as you can hear when I start talking with people like you who really care about this stuff and have kids and want their future to be bright—I’m motivated. Showing up to work every day is my act of rebellion.

If you want to be a benefactor to a place like the Ecology School, that is such an actionable way to do positive impact and invest in the future. I always tend to think of the glass is more half full than half empty.

When I helped found the Maine Outdoor School for All network 15 years ago, people would ask, “How can you work with 4-H and these other folks? Aren’t you competing?” It’s a growth model. If it’s an equity issue, every child should be able to go to an outdoor school in middle school to have that week-long inspiration, that rite of passage. It’s a growth model because only about 15 to 20% of kids in Maine get that now, and it’s definitely often the richer communities. So partnering together is actually not only collaborative, it’s good business.

Eric Ressler: What does deeper collaboration actually look like?

People say “we collaborate,” and often when you ask what they’re really doing, it’s barely collaboration. Collective impact is that deeper model. We’re lucky in New England, especially Maine—we’re a highly collaborative state in terms of environmental education, conservation work, and food systems work. There are a lot of cool organizations that play well with each other.

Eric Ressler: Before we wrap up, how would you like people to connect with you?

Drew Dumsch: Our web address is pretty easy: theecologyschool.org. We have a LinkedIn presence, Instagram, Facebook. I’m always looking for new ideas and figuring out how to convene people. I love what we do and I’m a big advocate of it. When we can bring more people into this work, it’s just wonderful.

Every month, political campaigns raise hundreds of millions of dollars online. They move fast. They test everything. They know what works. And most nonprofits are still trying to figure out if they should send an email this week.

That gap has been on my mind for years. Why are campaigns so effective at digital fundraising? And why is the social impact sector so far behind?

But here’s the thing: Political campaigns aren’t perfect. In fact, they get a lot wrong. The churn and burn tactics. The fake urgency. The impersonation schemes that drain trust from the entire ecosystem.

So the question isn’t just what can we learn from campaigns — it’s what should we take, and what should we absolutely leave behind?

To explore that gap, I wanted to talk with someone who’s got a foot in both worlds. Someone who’s run some of the biggest and most successful political campaigns in the country—and who’s also building something different.

Mike Nellis is the founder of Authentic, a digital agency that’s raised over a billion dollars online for progressive causes and candidates. He’s worked as a Senior Advisor to Vice President Kamala Harris and on presidential campaigns for Obama and Biden. His client list includes Adam Schiff, Cory Booker, and the United Nations.

But he’s also someone who nearly killed himself doing this work. For years, he was buried in anxiety and depression, using food to cope until he weighed 600 pounds. Over the last four years, he’s lost over 300 pounds and completely transformed his relationship to the work.

That journey taught him something critical: You can’t sustain this kind of work through misery. Now he writes with what he calls “endless urgency” — a philosophy about moving fast without burning out, about choosing resilience over destruction.

And he’s proving you can build attention at scale without a massive team. His Substack has grown to over a million followers. Just him. A laptop. And the right strategies applied with relentless consistency.

In our conversation, we dig into what campaigns know that nonprofits don’t. And just as importantly — what they’re getting dangerously wrong.

Full Interview:

Eric Ressler: Mike Nellis, thank you so much for joining me today. Really excited to have you on. I think the first thing I want to dig into is that you have a pretty unique vantage point in a lot of different ways. You’ve done incredible work with fundraising through your agency and personally. You’ve also worked with both causes and candidates. I think I want to start there. When you work with political candidates, what is the different way of thinking about that work compared to working with a nonprofit organization or a cause?

Mike Nellis: I think the foundations of it are roughly the same, right? You’re trying to create an emotional connection with people that makes them want to part with their money and support what you’re doing. And ultimately, I know that that’s maybe a crasser way of thinking about it, but that is at its core what it is.

Now, I think with political causes, as opposed to our clients—we work with the United Nations, we’ve worked with Red Nose Day, we work with a bunch of others—there’s much more logic to, I think, fundraising. And when you create content, there’s a lot more of an expectation that people understand where that money’s going and how it’s being useful. And on the political side, that content doesn’t perform as well in my opinion. It doesn’t perform poorly, but it doesn’t perform as well.

And so I think politics becomes more visceral, emotional. It’s part of the reason you see—and we don’t run these style programs—but you see these programs that are really based in anger and churn and burn and, you know, donate now or all hope is lost or all that stuff. I don’t think that works as well on the nonprofit side because people want to feel hopeful in terms of the donation they’re given. They want to be like, I’m giving you 25 bucks, we’re going to help save the ocean. We’re going to support abortion rights for women across—this is a lot of what we do with the United Nations is helping with reproductive rights and freedoms and healthcare in Africa through the United Nations Population Fund.

So I think people want to see progress, whereas on the political side, it’s much more—it’s like playing whack-a-mole sometimes on people’s emotions, which sucks. And the system shouldn’t work that way, but you kind of have to live in the world you live in.

Eric Ressler: Yeah, that’s something I’ve been thinking a lot about lately. And we recently had Amanda Litman on the show and we talked about this a little bit too. She’s awesome. Really great interview. You should check it out. We are seeing though, I think the bad sides of political fundraising start to seep into nonprofit fundraising, or at least I’m starting to see that a little bit. You know, things like outrage, fake urgency, these kind of empty promises around donation matches, which may or may not actually happen.

And I think to me, I see this as a tie into just a bigger cultural phenomenon around the attention economy and just how noisy everything is right now and what it actually takes to break through. And in my opinion, this is kind of unsustainable. And I think we’re all starting to feel that this kind of almost runaway experiment of social media and digital platforms that we’re on. How are you thinking about balancing all of that showing up in a way that’s true and honest and authentic, which we’ll get into that word a little bit more today, but also effective at the same time?

Mike Nellis: Yeah, if one more person says the word authentic to me, I get a free set of steak knives, I think. So I desperately want to build a meaningful relationship between my clients and our supporters. And if you look at the clients that I think have been the most successful at that over time, they’re usually the ones that you’d be surprised at the list size.

Right. That turns out as much money. We’ve worked with United We Dream for a long time. Much smaller list than you would expect given their fundraising. It’s true for a lot of our other nonprofit clients too. It’s even true for some of our larger clients too. I mean, Adam Schiff, who is my oldest client, I’ve been with him for 10 years, has a massive email list, but just has this gigantic following of people.

So if you want to create that type of alignment between you and your supporters, you have to spend more time on it. You have to do it right. And in my view, running an ethical and effective fundraising program that’s rooted in storytelling can raise you a lot more money than the churn and burn stuff. The difference is the churn and burn ones are usually from campaigns and organizations that don’t have a good story, aren’t interested in being patient, aren’t interested in building that connection.

If you build it over time, you raise more money. That’s why Adam was able to raise so much money for his Senate run. That was a 10 year project, essentially. We might not have known we were building it for that, but we got to a point where we could do that. What we did with Kamala in 2019 for a presidential election raised something like 30 million dollars, I think for her campaign at the time. What Bernie Sanders did in 2016, you build those connections, you get people to donate more money more frequently.

The challenge is that in this attention economy that we’re in, and I know this now as a content creator, the biggest thing that moves the needle is volume. It matters a lot more how many times you’re posting than the quality of the content. You have to self-police on quality. There’s a lot of creators out there, and God love them to death, they’re posting one video a week or one video a month, and it’s beautiful, detailed really really good and their growth is dead because the algorithms are demanding that you post regularly and so that’s why if you go to my TikTok page you’ll find a lot of videos of me in my studio with my phone in front of my face just complaining about what happened that day in the news.

It’s because I got to feed that algorithm and frankly I don’t do it enough. The truth is I probably post on average on Instagram and TikTok once per day when I should be doing it three to five times per day based on the algorithm, but I have a throughput problem. My throughput problem is time right now—time and attention and creativity because I also run my businesses and do this and I have a six year old. So there’s a lot of that.

I think the same problem with fundraising, right? The text messages in particular are completely out of control and it’s part of the reason that Apple is essentially creating a spam box for everybody’s phone to get rid of a lot of those. And I think it’s going to hit the nonprofit sector harder than it’s going to hit the political sector because political speech is going to be considered free speech and probably rooted outside of that over time, which would just be my guess. And the nonprofits are going to get stuck right into it. And that’s going to be a huge problem, but it’s a problem of our own making, frankly.

Eric Ressler: Yeah, I mean the text messages are definitely getting out of hand and there’s good work being done there. I think even on ActBlue’s side, we’ll see how it actually pans out. But at least it seems like some good faith motion towards more responsible data sharing and performance and things like that. I’m like a lot of people, I’ve donated to many campaigns. I get easily 10 plus text messages even though I’m actively trying to opt out every single day. And it’s to the point where I literally don’t even read them anymore. Right, because there’s just the volume is so much.

Volume is something I would like to spend a little bit more time on because you mentioned having to kind of feed the algorithm in order to break through in this attention economy that we’re in. When we’re talking about, let’s say executive directors of small teams at nonprofits or social impact orgs where you tell them a weekly email is a good idea and they start to get overwhelmed. How do we move the culture and the understanding and frankly, the belief in how important communications work is as it relates to fundraising and just social change in general, when it’s been traditionally this kind of piecemeal, “we’ll get to that when we have time, we’ll get an intern to do that.”

And I know this is not true necessarily for larger campaigns, but I think often people would be surprised how small some of the communications teams are, even in bigger teams.

Mike Nellis: I mean, there is a culture problem here, which I think a lot of nonprofits move very slowly. One advantage I have as I’ve worked in Democratic digital fundraising for so long is I move really fast at everything that I do. The name of my Substack is literally Endless Urgency. And that is not unrelated to the career that I’ve had.

When I work with these nonprofits, they’re hoping to get one email out a week. They’re hoping to get two emails out a month or something like that. And it’s just not enough. If you—this is the issue. We have this problem with our campaigns, particularly when we get towards August, September, October of an election year. If I on average send for my clients, I would guess anywhere between 25 to 30 emails a month, which is a lot less than a lot of my competitors. Now my emails are better written, in my opinion, they get a higher donation rate than a lot of my competitors.

The difference is that a mothership style program is going to send 100 emails that month in an election year in the election months. Since August, September, October, they’re going to send like 400 or 500 emails to people, they’re going to overwhelm your inboxes. So if I stay at 30 high quality emails, I’m going to get even more drowned out than I already am in order to get people’s attention. So I have to scale up and go to 100 in October, which is ridiculous.

So I’m beholden to the ecosystem that exists that drowns people’s stuff out. I have to worry about spam inboxes, I have to worry about deliverability. So everything’s just a lot more complicated. And a lot of the problem with the nonprofit world is they have fallen dramatically behind in terms of keeping up with best practices for volume, deliverability, tactics, scale, stuff like that.

On acquisition too, a lot of nonprofits are very opposed to doing bulk buy acquisition. I hate bulk buy acquisition to be clear. I do not think it is ethical, but I have no other alternative in terms of how to build my clients’ rosters in a world where Meta has virtually shut down our ability to build email lists the way that we used to. That’s a—in my opinion, that’s a tired conversation from 10 years ago, but you get a lot of people who are mad about it. I don’t have a better solution than the way we’re running our programs now.

I’m constantly on the lookout for one, but we’re so drowning that we can’t figure it out a lot of the times because every Democratic Party organization is overwhelmed and overloaded and it’s even worse in the nonprofit world. Plus they’re dealing with a mentality that’s 10 years old at best.

Eric Ressler: What do you think the end game is here? Because we can’t just continuously increase volume, increase volume, increase volume. And I think there seems to be some kind of cultural change happening digitally, at least from my vantage point around people feeling overwhelmed, people intentionally kind of unplugging a little bit more, which I think is very good and much more needed. I mean, maybe let’s just open this up outside of the nonprofit space, outside of the social impact space. How are you thinking right now about digital culture and the digital landscape and the intersection of that and just, I would say, our humanity at large.

Mike Nellis: Yeah, so I’ll split this up. The first thing is there’s the assumption that there’s eventually going to be a breaking point and everything’s going to change. I don’t know that there will be a breaking point and everything will change. People can put up with a lot, people do put up with a lot.

We’re living in a society right now that is, in my opinion, just broadly mentally unwell and a lot of that has to do with algorithms and volume and the content that people are experiencing in 45-second increments on their TikTok and the incentive structures that exist for the type of content that creators create. And that is a really serious issue.

The social media companies and the billionaires who own these algorithms are not going to self-regulate themselves into doing something better. This version of the federal government is not going to solve that problem. Maybe a Democratic version will, but I’m also pretty skeptical about that because the Democratic Party is struggling to articulate or be able to solve any of the problems it wants to solve that are higher up the food chain, but this needs to move higher up the food chain, frankly, I think for the Democratic Party too, because it’s a pretty serious issue. So there’s that.

Right now you can take personal responsibility for your digital wellbeing. That’s the answer. I spend less time—I was off social media for years. I did. I missed TikTok entirely as it rose. I came back into social media and I was still looking for Vine. And now I know what TikTok is. I’m on TikTok. I’ve got 50,000 followers or something like that. So it’s not unsuccessful, but it is a platform that I’m uncomfortable with because typically when I’m thinking social media, I go to YouTube because the YouTube algorithm has me pegged.

I think people have to decide for their own mental wellbeing, what it’s going to be like, because we’re living through an era of self-regulation and self-ethics. And again, billionaires and big tech companies, they’re not going to regulate, they’re not going to protect our kids, they’re not going to protect ourselves. I think you’re going to have more and more bad faith actors who take advantage of the situation.

And the thing is, I would argue that my firm in this space is the most ethical actor that exists. We take every precaution that we can. We’re very thoughtful about the programs that we run. We get pushed in directions that we don’t want to by the market forces. And that is the bad faith actors who overwhelm.

Impersonation is a huge issue for us. We did Cory Booker’s online fundraising when he did that filibuster. We had to wait until we could fundraise until after Cory was done, because it would have been inappropriate for us to have been fundraising while it’s happening. Well, a bunch of Democratic Party, quote unquote, aligned organizations went live with content and ads and they were raking money claiming that it was going to Cory Booker and we probably lost a couple million dollars I bet that’s now in the pocket of a consultant that has another house in Maui somewhere.

So that’s the type of stuff that is wrong and it requires us as the good faith actors to be more aggressive and to bend our ethics because we have goals and expectations that we have to hit for our clients too. So I just don’t know, there’s been—my entire career since we started, I mean I’m basically one of the first generation of people to do this 20 years ago.

People have been saying email’s going to die, we’re going to hit the cliff, it’s going to be bad, and then it just doesn’t. People sort of amend to it. So I’m not saying it won’t happen to be clear, I just feel like every three years there’s some prediction that we’re hitting a turning point and then we don’t. And I sort of am skeptical.

Eric Ressler: Yeah, and to be clear, I actually think I agree with you and I worry about the trajectory because I’ve also been observing digital culture basically as I’ve been growing up. And there’s a lot about it that’s awesome, right? And there’s new spaces out there. I think Substack is one of them that, you know, not a perfect platform, but a lot of things that I like about it compared to some of the others, right? Especially from the tech side. So—

Mike Nellis: If you’ve ever done a live, you know it’s not a perfect—my God, I love them. I love Substack so much to be clear. Don’t kick me off the platform, but the live function needs work.

Eric Ressler: Hopefully some improvements coming there. Nonetheless though, we’re seeing everything get kind of chopped down and clipped down into shorter and shorter sound bites with less and less depth. And at the same time, in parallel, people have no problem listening to a three hour Joe Rogan podcast. So there’s this kind of narrative that everything is short form, everything is short form, long form is dead. People still watch long movies, people still read books, although that’s certainly down. So there’s this just weird amalgam of different types of content. And I think people are searching for stuff that’s true and that’s becoming harder and harder to find.

And as AI comes in and there’s more deep fakes and clips cut out of context and algorithms feeding outrage, it’s just a messy world out there. And I’m definitely seeing people struggle, especially in the social impact space around how do we show up right now in a way that actually works? I think there’s this perception that in order to win in this attention economy, in order to do this work well, we just have to have this big team and we need to have all these resources and time and money. And there’s some truth to that, right? If you treat this as a side project and this kind of, let’s get the intern to do it, how hard could it be to send some social posts out? It’s not going to work.

But at the same time, I think some of the most successful campaigns have been done by a small group of really smart people who care about the work and do it well. To use you as an example, you’ve built a Substack following of over a million people. And as far as I understand, it’s mostly just you doing a lot of it. I know you have some a small team supporting you, but maybe you could just talk about what that trajectory has looked like for you and how you think about showing up and growing that following in a meaningful way.

Mike Nellis: Yeah, I have no team supporting me. I mean, I have an assistant that helps with scheduling stuff, but we just hired a community manager to help scale up our content because again, I need to be posting more than I am. The truth is I post—I treat Substack a lot more like a blog. So I post rants, not newsletters. But so usually there’s two a week, but based on the response, I could probably send five a week. And I think people would tolerate that type of volume because again, the news media and the landscape is changing so much that people have an expectation of hearing from you so regularly. People forget who you are like that.

So you got to be a lot more aggressive. I want to go back to something you just said though on, you know, people tolerate a three hour Joe Rogan interview and then they’re also looking for things in 15 second increments. There’s different audiences of people and I think you have to understand who your audiences are.

But one thing that Rogan is exceptionally good at, and I described this to somebody on the Harris campaign last year, is trying to explain why they should do Rogan, is that it isn’t just Rogan’s podcast. Yes, Joe Rogan sits down for three hours with God knows who talking about God knows what and I don’t know, maybe half the time it’s pretty good and the other half of the time it’s ridiculous stuff. But there’s a whole economy under Joe Rogan.

So there’s the Rogan accounts that get that out, push their stuff, they get it on Spotify, they make a ton of money. But then there are all kinds of clip factories out there that are posting short form clips. I would argue that the way most Americans experience Joe Rogan is not through the show properly. It’s through these, you know, minute and a half clips that they get of a back and forth and stuff like that and people interspersing him into—I don’t know if you’ve ever seen this one. He has one where he’s like, Jamie, pull up that video of that crazy thing that happened and people will grab that and then they’ll put something else that they want there.

I’m going to actually start doing that myself, because I want to see if it’s successful for my stuff to do that and then cut immediately to Trump trying to pronounce Semaglutide this week, which if you haven’t watched that, I highly recommend it, it’s hilarious. Honestly, it was one of those times where I was like, somebody help him, please, I feel bad for him right now. But so there’s a lot of that and I think people have to understand, go look at my show.

You asked me about my show, so I’ll answer it. I go live basically twice a day for about 30 minutes to an hour with somebody. I try to have a meaningful, interesting conversation with them. The general vibe I wanted to be is that if this person and I were sitting at a bar drinking a beer, talking about our day, it would not be dissimilar if we were reacting to the news of the day. Because I’m not bringing a character. That’s the other thing is a lot of people develop a persona and a character of themselves that they get. And I might dial it up 10% or dial it back 10% depending upon the topic.

But I tell people this all the time—can I curse on this show, Eric?

Eric Ressler: Sure, all right.

Mike Nellis: I’m the same asshole in every room. Every single room. It’s something my father used to say to me. My father would be like, I’m not a different asshole when I go over there. I’m not a different asshole here. I’m the same guy. If I’m on a work call, that’s who I am. When you watch my show, that’s who I am. When I’m on Jesse Watters, fighting with Jesse Watters, that’s the same thing. Now I’m a little bit different, but I don’t have a character.

You know, Bill Maher has that sort of famous moment where he went to have dinner with Donald Trump and he was like, Trump is so different than you would expect when he’s on TV. And I’m like, yeah, no kidding. He’s playing a WWE character. He’s the heel. So we need a lot less of that. And I think people are trying to snuff that stuff out. So they’re looking for people that they can relate to who are real.

It’s why Rogan is successful. I believe that’s the real Joe Rogan. I believe that’s the real Theo Von when I watch his show. And because of that, it makes the conversations a lot more interesting. I think if you do that and you come in with consistency, you can get a following. And it might not be a big following, but I would rather have 5,000 hardcore people that are with me every day than 2 million people that maybe show up every now and again.

And there are a lot of YouTube channels that I’ve seen, and I don’t know if they paid for this, where there’ll be people that are prominent, you know, progressives or conservatives, and they have 2 million on YouTube, and you go look at their views, and their views are less than mine. And I have 2,500 on YouTube. I do not have a big YouTube page.

So I just think that the algorithm matters here, but also the connection and the intensity matters a lot here and I think you should—the other concept that I have that I think is useful is, and I haven’t fully been able to execute this for my own, because I need help. I need a small team of people, it’s why I’m bringing on a community manager, I’m trying to hire a video editor right now too, is I believe in the—this is what I call it, is the Russian nesting doll theory of content. And I’m pretty sure I came up with this, but if I didn’t and I’m stealing it from somebody, I apologize, because I can’t remember anymore.

But it’s you know, Russian nesting doll, you pull it out, there’s all other things pulled out. So I have Endless Urgency the Show, I’m on for an hour, I pop that up, it’s TikToks, I pop that out, throw it into an AI thing, and I have tweets, I pop it out in here. And I’ve gotten some of that going so I can build a model of it, it makes me more efficient. But that’s what you want.

So I think if you’re a one person shop or a two person shop, you’re running a congressional campaign, go live once a day, at the end of the day, talk about what’s going on, bring on a guest if you can, build that connection on a Substack, then distribute those clips throughout and you can do that. You don’t have to be—when we did Adam Schiff, he had a full video team. Mallory McMorrow has an amazing video team on her campaign right now that put out that Super Bowl, or not Super Bowl, the NFL Red Zone ad that everybody liked so much. That was real work that went into that. That was art. There was art to that that was really cool.

I’m not capable of making that, but if you need me to shoot a 45 second TikTok video, I could do that and yell at the screen and call Donald Trump the most corrupt president in American history, which I do pretty frequently. This is different. Do what you can, but consistency matters the most with these tools.

Eric Ressler: Yeah, I want to pull on that thread a little bit more because I think specifically what you said around, I’m the same asshole in every room. And there’s been a lot of discussion about that as it relates to specifically Democratic candidates. But I actually think we need more of that in the nonprofit space too, not necessarily that they’re assholes, but—

Mike Nellis: And I’m not really an asshole either. You will find people who will tell you that I’m an asshole. Sure they exist. My wife is probably among them.

Eric Ressler: The point being though that there’s this professionalization and academia kind of mentality in the nonprofit space that I think is rooted in good, right? It should be serious work, especially when we’re talking about big social issues. I want true researchers on those teams. I want academics on those teams, but that kind of communication just does not work anymore.

I don’t know if it ever really worked, but it especially doesn’t work right now. And I think that we need more nonprofit executive directors who are out there making content in this way instead of sending the monthly digest style newsletter about their annual report or whatever. And it just seems like there’s a reluctance from some leaders, not all leaders, to be able to show up that way. But when I see examples of leaders who are showing up that way, it seems to be significantly more effective and doesn’t require these big teams to create these super polished branded videos.

Mike Nellis: Yeah, I think you need people who can talk like a regular human being. And I don’t think that it’s—I think there’s an assumption that America is getting dumber or something like that. I don’t really think that that’s what it is, that people’s attention spans are shorter. They’re being trained to be shorter. And they’re also deeply skeptical of intellectuals right now. Like it or not, one of the institutions that has let people down is academia. And I think there’s now a distrust of academia.

And when you have conversations with people, the more that you’re like, the Harvard Law put this study out that said blah, blah, blah. People are like, okay, whatever. Do I even know that’s real anymore? It’s what leads to people running towards an RFK Jr. who is a quack. And you know I often say about MAHA is the bottom third of MAHA makes a lot of sense to me. There’s some stuff in there about red food dye and sugar and things like that. I mean, I used to weigh 600 pounds. So I think that’s a real thing. But then he’ll be like, Tylenol causes autism, which there’s really no actual link to and is to me pretty dangerous.

So you need smart people in the room who know what they’re talking about and understand the research and I listen to those people but part of my job is I’m not an intellectual. I talk I think a lot more like a regular person than not. My job is to distill that and help other people understand it. So you need—if I was thinking about who I want to be the CEO or the public face of my nonprofit, I would be thinking about somebody who could make a donor call. I’d be thinking about somebody who could do a TikTok. I’d be thinking about somebody that could go on TV and do the press. I would make sure that they were surrounded by really smart people that were forming the policy.

But you mentioned the Democratic Party having this problem, and I’ll just give the sort of treatise that I have on this is Donald Trump, when he ran for president, was like, build the wall, drain the swamp, no tax on tips, very simple stuff. He might’ve said a lot of crazy stuff around it, but people got the four or five messages that were most important to them because they were three words long. Bernie Sanders was the same way. Medicare for all, free college, like those are very basic principles. People care a lot more about that than anything than they do about anything else that they can understand what you’re running for.

Zohran Mamdani, Freeze the Rent, I think is the best TV ad I’ve seen since the They/Them ad with Donald Trump, which is also a very simple basic ad that I think tanked Kamala Harris’s presidential campaign, frankly. And I know a lot of people think that that’s overselling it, but I actually really believe that based on the research that I’ve seen.

Democrats need to do that because the reverse is we go, we have the blah, blah, blah act. And with the blah, blah, blah act, you can file Form 72B with the IRS, make sure by the way you file it on a yellow sheet of paper and if you file it correctly at this time when the lunar eclipse is like this, you can get a 37 cent tax rebate. And it’s like, what is that? And that happens every single time with the Democratic Party.

And so that’s kind of why we’re struggling right now. People are like, can we articulate the vision for the party? Well, no, we can’t because the thinkers, the academics, the policy tank folks have good ideas and good policies, but they need to be a lot more actionable and they need to be simpler to explain. I think in the nonprofit world, it’s got to be the same. The simpler that you can make it, the better.

I liken it sometimes to the difference between the guy who founded Savannah Bananas and the guy who is currently the Major League Baseball Commissioner. It’s just entirely two different people. They’re the same relative to the leagues that they have, but look at how different they are. And what’s the name of the—is the MLB commissioner still Rob Manfred? I think it is.

Eric Ressler: You’re asking the wrong dude.

Mike Nellis: Yeah, somebody out there will fact check me on that. I don’t remember. But the Savannah Bananas guy whose name I don’t know. But if I saw him, because he’s always in a yellow suit, I remember that guy. I don’t think you have to go full Savannah Bananas to be interesting, but you can find your version of that. But that’s how you get people interested in it. They’re taking an existing thing that people find boring and they’re putting a new flip on it. And to me, it’s pro wrestling baseball.

But we’re in pro wrestling politics right now, so I think people need to sort of be mindful of the fact that that’s where society’s moving and we got to be more interesting to get attention.

Eric Ressler: I’d be curious to hear kind of your theory of how social change does or should happen, especially in America, where there used to be in a good faith way, and maybe not always very effective, this kind of partnership between the federal government, state, local governments, and community-based organizations and nonprofits to enact a lot of that social change.

The entire playing field is very different right now with the current administration and basically all, not all, but most federal funding, especially for anything progressive being either completely cut or frozen. And it’s leaving our sector sort of scrambling for funding in a lot of ways. And a lot of that funding is now moving towards individual donors, major donors, some philanthropies, although philanthropy has not really stepped up to fill the gap and isn’t even capable. So how are you thinking about—

Mike Nellis: Because they’re under attack too. Yeah.

Eric Ressler: Obviously, if you’re especially trying to do any kind of progressive change, anything that is under scrutiny or under attack by the current administration, this change is still important, if not more important than ever, and it’s harder to get funding from and support from the federal government for that change. What are you seeing from your vantage point around, you know, in a tactical way, how to get over that, but just in a bigger picture cultural change way, how do you think we need to fix politics in order to, if that’s even possible now, to get through some of these bigger social changes that we want to see or is the way that we need to enact social change going to just shift because of this? How are you feeling and thinking about all of that in a bigger picture way right now?

Mike Nellis: Yeah. If you look at the history of American politics, the history of politics period, there are ebbs and flows where things function and don’t function. And is this the worst it’s ever been? Maybe. I don’t know. I think you really sit back. You can look at other administrations in the past and go, that was rough. And people did not trust each other. And sometimes it was there was massive distrust with the federal government, but the federal government was right. I mean, time tells all.

I mean, there was plenty of times where southern states did not trust the federal government to the point where they seceded from the union. So it isn’t that bad yet. So I just always remind people put it into context. It is bad. Don’t get me wrong. And it is hindering progress in this country. And I’m generally somebody who believes that Donald Trump is a fascist, is a wannabe dictator. I use those terms with intentionality. And that is an issue that’s impacting all of us.

And now I go the opposite way. I think that the way society often incentivizes us, the way the algorithms incentivize us to be focused on the big things in the world that we cannot control. So national politics, D.C. Even major things like Palestine and the Sudan and what’s happening in both those countries is horrible. But people get so focused on that and you can’t really do anything about it. Which is not to say that collective action isn’t important, collective action is absolutely important.

I encourage people a lot of times, this is what I do in my own personal life, just try to—how I think about it is my dad when I was a kid, my dad’s a big Republican, I’m left of center, I think I don’t really—I wouldn’t call myself a liberal, but I’m left of center. So my dad would say, my responsibility is to take care of myself and my family. He’d put his fist up like this and he’d go, this is just the five of us that we have to take care of. And I always thought that was a little selfish.

As I’ve gotten older and I have my family, I think it’s more right than it’s wrong, but it’s limited in the way it works. So I think about it as I got to take care of myself and be—and I say this as somebody that I didn’t take care of myself for years. I was so committed to the work and I had mental health issues that I ballooned up to 600 pounds. So I needed to get focused on my physical health, my mental health, my digital health, my spiritual health, et cetera, to then be useful to my family.

So think about it like a concentric circle. So I’m now useful to my family and I can take care of my son, I can take care of my wife, et cetera. Then I could focus on my community, then I could focus on everything else. And I think more people need to think that way because I can’t stop Donald Trump from being the tyrant that he is, cutting off people’s funding, not listening to Congress, ignoring the Supreme Court. Those things are horrible. And again, collective action is really important and that should be part of how you’re positioning yourself as a citizen.

But a lot of times you go this way down and so you ignore your physical and mental health, you ignore your family, you ignore your community when you could strengthen all those relationships. And my general theory of the case right now is you want to make the world a better place, you want to solve a lot of problems, you start bottom up. And so you start with yourself, you make yourself mentally strong, physically strong, you make sure your family’s in a good place, you raise good kids, you be the partner and spouse you want to be, be the friend you want to be, you fix the shit in your community that’s actually fixable.

And so I ran for school council down the street. There’s a small school over here, my son doesn’t go to it, they needed a community rep. I got elected by about 10 teachers and parents. And my job is to source beanbag chairs for the sensory room for the kids that need it and help them get the money for a TA and stuff like that. And I genuinely, I get more value in my own life out of it. It’s selfish a little more than a little bit. But I also think that work is more important than a lot of the going on Jesse Watters and arguing with him in front of four and a half million people.

That’s the stuff that people see and that people care about that. I do it because it’s important and I do it because it draws new followers, which then helps me with the rest of the messaging and things I want to get out. But I think what I do there is more. And I think I’m more fulfilled by that. So I think if you’re lost in this, maybe—I don’t know if this is answering your question, Eric, because I don’t have a solution for nonprofits, I’m sorry.

But if you’re lost in this moment and you’re frustrated with whatever it is, you might be frustrated from the right too. You might be a conservative going, this isn’t what I want either. Go pick up trash in your neighborhood. Go be useful somewhere there. I just think if more people did that, we’d actually be in a better position. And if we had more people who did that, we’d have a better crop of leaders on both sides who would eventually run for city council and mayor and Congress and Senate because they have actually been in their community instead of what we have is a lot of pseudo celebrities and influencers that are now using it as a stepping stone to become a Fox News host or an MSNBC host and I’m tired of that shit too.

Eric Ressler: Yeah, I want to end before we wrap up, just kind of, if you’re open to it, talking a little bit how you’re thinking about the next generation. We’re in this generational change, both in terms of leadership, but also another new generation of kids growing up. And you’re a dad, I’m a dad also of some young kids. And I think a lot about all of this as it relates to what does their future look like. And I’ll be honest, there are times that I’m very pessimistic about what that looks like. Bigger things like climate change and all the political violence that’s happening right now and just the general ecosystem.

I drop my kids off at school and I have to, in the back of my brain, think is this going to be a school shooting day and am I going to be affected by that, right? These are things that are not symptomatic of a healthy society. And I don’t think it’s constructive to spin out on that stuff, even though it is rooted in truth.

It makes me energized around how can we create a better future for our kids, which I think ultimately what everyone wants even if they’re really misguided around what that looks like or if there’s different opinions around what that better future looks like. I mean that is in a good way it’s kind of the American experiment that I hope that we can continue to work towards together in some kind of constructive way even though there’s been a lot of polarization and the trajectory has not been good but back to my question.

How are you thinking about, you know, you mentioned taking care of yourself first, taking care of your family next, raising kids in this environment and doing that constructively and doing that in a way that builds community and builds character and sets up that next generation for success.

Mike Nellis: Yeah, I spend a ton of time thinking about how to raise a good man. I mean, the joke with my wife when we got the news that we were having a boy, I remember we were riding an Uber back to the house and I remember going, we’re having a white man. And it was sort of during all the Black Lives Matter stuff, so it was a little bit more topical than today, although I still think it’s really topical today. But I want to raise a good man.

And I think we’re watching a world that is dominated by the worst possible role models and the President of the United States is Donald Trump and I think he’s not a good role model for anyone. You just look at his own kids to find that he’s not a good role model for anyone. And beyond that, it’s who are the loudest, most successful voices talking to young men right now? It’s Andrew Tate. And Andrew Tate is a dangerous individual. Now he is a symptom of a system that doesn’t work.

And we’re also raising the first generation of young men who are going to make less money than their female counterparts. I mean, women are twice as likely to graduate from college, twice as likely to buy a house right now under 30. That’s crazy. It’s the first time it’s happened in American history. We should not do anything to get in the way of that, because it’s incredible progress. But I think we need to make sure that men see their path in the future too. Otherwise, they’re going to listen to people like Andrew Tate, and Andrew Tate preaches violence against women.

So I think about that a lot, what you said about school shootings hit me too. My son had his active shooter drill, his second one a couple of weeks ago and I don’t like that happening. I don’t like getting that email and I don’t like answering those questions when he comes home. And I don’t know, but again, I think it’s I don’t have control over school shootings. I can’t stop a random person from getting access to a firearm in a country where it’s really easy to get a gun. I mean, I’m a gun owner. I own a Glock 19. I went and bought it. I trained with it. I know how to use it, but I know how easy it is to get a gun. It is not hard.

And honestly, I got a little bit frustrated by the three day waiting period because I didn’t want to have to drive back out to the suburbs to get it. But I was like, no, I need this. This should probably be a five day waiting period. You can’t control it. So focus on what you can control. Make sure your kids are smart, empathetic, get good educations, that you’re there and present in their lives. I just feel like that’s—to me is I also I’m a joyful warrior. I refuse to be miserable.

In the first Trump term, I became a very miserable person and it had huge ramifications on the parent that I became, the father that I was, the human being, the boss that I became. I didn’t like any of it. I’m not doing that this time. I choose to be joyful in the face of death threats. I choose to be joyful in the face of all the political violence happening around us and the way that they’re framing the left right now as being responsible for that political violence, which to anybody listening is ridiculous. Both sides are responsible for what’s happening right now and both sides should be trying to do better.

But I think you just push forward one step at a time and you don’t give up. Because I’ll also say to the forces who want to take this country in a direction that I don’t think Eric, you or I agree that it should go in. They want you to quit. They want you to become cold. They want you to become lifeless. They want you to lock down and you can’t do that either. We need more people that keep their heart and keep their soul.

One of my biggest fears when I’m up late at night thinking about the future of the Democratic Party, which for some reason is one of the biggest things I think about all the time, which would, if you’d explained that to me when I was 14 would make no sense to me. Because I wanted to be a football coach. I was going to be a football coach. That was what I wanted to be. And I worry the Democratic Party becomes the mirror image version of the Republican Party where the Republican Party’s party of grievances. They don’t care about how they’re going to solve people’s problems.

When was the last time the Republican Party presented a solution on anything? They’ve passed no laws in the last nine months. None. They’re just outsourcing everything to executive actions, and they can complain about Joe Biden signing EAs. What Trump has done is ridiculous. The Democratic Party has a lot of solutions. People don’t believe we can get them done. Oftentimes they’re complicated and they’re disaffected from people’s day to day lives. That’s a different problem. At least there’s solutions. At least they’re trying to help people.

And I get asked this all the time when I do these media hits, it’s why are you a Democrat? The answer is it’s the only party that gives a shit about whether or not you have a good paying job and can live the life that you want and retire with dignity and have a vacation every now and again. And unless that becomes not the case, I will remain a Democrat till the end of time. And we got to fight, we got to hold onto that. And we got to get better, tougher, stronger about the things that we’re doing.

Nonprofits have to get better, stronger, tougher about the things that they’re doing, but not lose sight of the mission because there’s a reason we wake up every morning and care about this. You or I or anybody else listening to this could probably be working somewhere else, making more money, and clocking out earlier than we do in the jobs that we have now.

Eric Ressler: I think that’s a beautiful place to end. Mike, thank you so much for your time today. Where would you like our listeners to dig deeper, follow you, subscribe, et cetera?

Mike Nellis: Yeah, you can find me on any major social media platform, but mostly my Substack, endlessurgency.com, if you’d like to subscribe.

Eric Ressler: Awesome. Thank you so much, Mike.

Mike Nellis: Thanks for having me.

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Most philanthropic foundations are built to last forever. They're guided by a dominant philosophy: Preserve wealth, preserve institutions, preserve power. The idea is to generate resources for some future rainy day and then swoop in to save the day.

But there's another approach. It asks: What if the rainy day is already here? What if saving for a distant future is pointless if communities are in crisis now? That flips the usual script.

Foundations have long been criticized for hoarding wealth, for funding with strings attached, and for prioritizing their own survival over the needs of the communities they exist to serve. Those flaws are only sharper now.

Federal funding has been cut, nonprofits are scrambling for dollars, and the sector is more competitive than ever. The old power imbalances between funders and implementers are only getting worse. In a moment when communities need solidarity, philanthropy too often defaults to playing it safe.

So what does this other theory of philanthropy look like in practice? To answer that, I wanted to talk with Jen Nguyen.

Jen is the director of post-secondary success at the Stupski Foundation, a spend-down organization designed to disappear after giving away all of its resources by 2029. She's been candid that she'll likely leave philanthropy altogether when it does. In her words, she's got nothing to lose — which means she has an unusual freedom to speak openly, challenge her own field, and ask the questions that others often avoid.

Jen started her career as a college counselor working directly with first-generation students. Now, as a funder, she leads multi-million dollar initiatives to help students persist and graduate. At the same time, she's pushing philanthropy to be more candid, more urgent, and more just. She's emerged as a sharp voice in the sector, writing essays, running a column called "Philanthropy Confidential," and making the case that maybe institutional philanthropy shouldn't exist at all.

I'm Eric Ressler, and this is Designing Tomorrow. And now, my conversation with Jen Nguyen.

Full Interview

Eric Ressler: Jen Nguyen, thank you so much for joining me today.

Jen Nguyen: Thanks for having me, Eric. I am really excited about this conversation.

Eric Ressler: I am too. As we've started this series and started to get more interviews in the mix, I've been trying to get some funder voices on the show. And that's been a lot harder than I expected. I was hoping that as I've been reaching out to different people in my network and people I don't know who I think would be a good fit for the show, that largely people would be receptive and open to it. But I have found that funders have been the least receptive and the least open to it. I'm just curious, why do you think that might be?

Jen Nguyen: If I could take two betting guesses here, even though I'm not a betting person, the first thing that you're witnessing is probably this wait-and-see approach that funders typically take, even outside of the current moment. Let's wait and see and analyze the entire situation and try to come up with a perfect solution to a problem. And you're noticing that that wait-and-see approach doesn't work when the current situation moves very, very quickly.

The second guess that I would make is that talking about the current moment and our philanthropic practices requires some level of reflection of what's happening within foundations. And I have found that foundations typically are not very reflective in nature or candid about their practices or transparent about their practices. That may be why you might be having some challenges getting communications directors to reply to you at this current moment, because they're probably wondering, what can we say? What can we not say? And maybe the foundation hasn't quite figured it out yet.

Eric Ressler: That was my suspicion. Something that I've been reflecting on, as I've been serving the social impact space for a while now through a couple of different crises. The first real crisis was around COVID and all of the lockdowns. What I noticed in that moment is that there was a clear threat and a clear issue that had to be overcome in the social impact sector. At the time, it felt like there was a rallying in the sector to come together and to work together. Granted, a lot of that was from government in terms of new government funding coming in, which obviously is not happening right now. But it also felt like the funding arms of the sector rallied and increased spend out in a way that felt tangibly, materially real, and also in a way that felt like it was in solidarity.

In this moment where there's been another major crisis for the social impact sector with the federal government drastically reducing federal funds for social impact organizations and community-based organizations, the spend down of USAID, there doesn't seem to be a response from the philanthropic sector that matches the need and the gap that's been left in this moment. Do you agree with that? What are you seeing from your vantage point?

Jen Nguyen: One thing that's really interesting is I've been at the Stupski Foundation since 2019, so I've ridden this wave of different crises. I did notice the solidarity among funders to really want to give more during 2020 and during the COVID crisis. But one thing to note is that they didn't actually give that much more. The payout is set at 5%. In 2020, the payout rose to 6.6%. So unless you're one of those people that's like, "1.6%, that's amazing," it didn't really get that much higher.

Even in that crisis, it was enough to push out maybe more press releases and communications about what people were doing. But in terms of dollars and cents, I don't think we've seen that materialized or at least sustained over time, which is the moment that we're currently in. Because we haven't had the muscle memory as a field to really give during moments of crisis, I think that's what we're suffering from right now as a philanthropic set of entities.

One thing to also mention is that what's built into the muscle memory of foundations is this idea of saving for a rainy day. We're trying to save money for some reason to continue operating 50 years from now. But the argument that we at the Stupski Foundation are constantly trying to make is the rainy day is here. So what are we saving for?

What good is the Stupski Foundation going to be if it exists 50 years from now? And even if I exist as the director of post-secondary success, if post-secondary institutions don't necessarily exist in their current form. That's the thing that we need to navigate as a field is trying to figure out if the rainy day is here. I think it is. And what are we trying to save? Is it our institutions and our society or is it just ourselves? And what I'm noticing is the answer seems to be, whether it's verbalized or not, we're trying to save ourselves.

Eric Ressler: The Stupski Foundation is what's known as a spend-down foundation or philanthropy. You have set, I believe it's 2029, as a goal to spend down literally all of your assets and shut down shop. Can you tell us about how that decision was made and how does that feel as a team to be part of an organization that you know is rightfully, if you agree with this philosophy, putting itself out of business, so to speak?

Jen Nguyen: The Stupski Foundation has been around since 1996 in different iterations. We were operating as an education funder for nearly 20 years, shut down in 2012 when Larry Stupski passed away from prostate cancer, and then we opened up again as a spend-down foundation.

Even though Joyce Stupski is not currently with us, she passed away in 20211, her vision at that time in opening up as a spend-down foundation was, one, if we push out a ton of money, what kind of maximal and quick impact could transpire regionally in the places that she calls home, Hawaii and the Bay Area. The second reason she wanted to do a spend-down foundation was because she was deeply inspired by Charles Feeney of The Atlantic Philanthropies, who spent a vast majority of his wealth in his lifetime and passed away in San Francisco, where we currently operate. And the third reason is less of a head reason and more of a heart reason. Joyce really just wanted to make Larry proud in this last chapter of the Stupski Foundation.

When lots of folks think about spending down, they think about all those head reasons, but there are a ton of heart reasons that are legitimate as well. And I think that's the one that resonates the most with me. It's this idea of not just Joyce's legacy, but her joint legacy with her husband.

In terms of how that makes me feel as a spend-down foundation employee, on a philosophical level, it's really interesting working for an entity that is about to end because in many cases, it's about letting go. If I'm annoyed with a conversation with a colleague, I'm like, will this matter in two years when I'm not employed at a foundation? Let's let go.

That's a micro thing, but at a very macro or practices level with grantees, it also applies. When you give out a grant in a spend-down foundation, usually it's going to be one of the final grants that you're ever going to give with that particular entity. The mentality is less about compliance and more about, it doesn't matter if this thing is working in the middle of the grant or not. You've got to make it work because it's the last grant. My position as a program officer/director is less about checking in about what's not working and trying to figure out if there are numbers that match up to remove the grant. That's not the role that we take. It's really about how can we build the capacity of these organizations or help the organization succeed with the remaining resources that we have. It's a fundamentally different way of being in relationships with grantees.

Eric Ressler: This ties into a broader trend and discussion point around what's been dubbed trust-based philanthropy. I can try and summarize my interpretation of what that terminology means, but I'm also seeing it being used in a lot of different ways. To me, it feels like that term is being brought into our zeitgeist because there's been a frustration, especially from the grantee side, around very competitive grant cycles, arduous reporting that isn't accounted for in the budgets of these grants, and a feeling of a transactional approach instead of a partnership-based approach to philanthropy.

My interpretation of trust-based philanthropy is that it's done more in partnership. There's less scrutiny, there's more trust in the frontline implementer type organizations to understand what the priorities should be instead of taking the lead from philanthropists on what the priorities should be. But I'd be curious to hear, is that a term that resonates with you? How do you think about and define that? And do you think this is a movement that is gaining traction, or do you think this is a hope and a dream and a fad that ultimately will just be squashed by the bigger machine and the muscle memory of the philanthropic sector at large?

Jen Nguyen: It's a great question. Regardless of whether we understand the framework or the definitions of trust-based philanthropy, from my perspective, the simple way of describing it is that organizations should spend more time with their constituents and users of their services than with people working in philanthropy. We need to invert the amount of time that people spend with us versus the people that they are actually serving.

What that ends up translating to is a series of practices, which include things like if you write a proposal for one foundation, it should be good enough for another. When we check in, it doesn't have to be multi-page reports. It could be a verbal report, just as rigorous in my opinion, as well as another series of practices.

There is this false equivalency of trust-based philanthropy being not rigorous and not accountable. But I do find that there's a level of trust, relationship building, and accountability that just looks a little different in these practices. An example that I could give you is every year I check in with school districts that I work with, we look at data together, but whenever there's a data point that looks a little awry, my question isn't, why is that happening and what are you doing wrong and what kind of punishment can I give this grantee in terms of compliance? It's more like what's happening and how can I help you?

And what we find is, for example, when a school isn't doing very well, maybe there's a series of bureaucratic challenges happening at the superintendent level and my job is now to go to the superintendent and ask, "Hey, what can we do to help out this school because I'm noticing this trend?" That's shifted my relationship in a really fantastic way and morphed my role to something that's a lot more rewarding and fulfilling than someone who's just counting beans on the side. That's the nature of trust-based philanthropy from my perspective.

Now, is it gonna be squashed by the powers that be? One thing that I wanna point out is, philanthropic entities are supposed to be bipartisan in nature, but we know that the field has gone into different, not necessarily partisan ways, but they're supporting things that are dramatically different on one side of the spectrum to the other.

With that being said, some of the most successful initiatives like school vouchers, for instance, have been supported through long-term funding. One could argue trust-based funding of initiatives that are of a wide spectrum: grassroots organizing, parent groups, think tanks, things like that. They're engaged in trust-based philanthropy, whether or not they know it, because their eye is not on compliance, it's on this bigger goal of privatizing education.

As a public systems advocate, I would say that we need to apply those same practices if we want to protect our public systems to continue serving the people who are most impacted by bad policies. You can call it whatever you want, but really what it is, is we need people to spend more time doing the work and not talking to program officers, if that makes sense.

Eric Ressler: There's so many good threads I wanna pull on there, but I wanna start with the last thread that you introduced. Something I've been thinking about a lot and trying to tease out with some of the different folks that we're interviewing on the show. And that is: what is the right mix and balance of these different social change bodies in society? And how can they best work together to create social change effectively?

You have the government, you have the social impact sector, you have the free market as basically the three main forces. There are some people who say, if the government just did their job, the philanthropic sector wouldn't need to even exist at all. These problems are the leftover problems that the free market and the government haven't solved. And that's the whole reason the third sector needs to exist in the first place.

It makes me wonder sometimes, we're in a moment right now where the way that government is being used — or not used — is changing very dramatically, at least in America. And to some degree, it feels like it can no longer be counted on as a trusted partner, especially if your mission as a social impact organization has anything to do with progressive values or DEI or anything that's been banned or scrutinized under the current administration. To me, that feels like an obvious miss because my interpretation of the way things could have worked — or used to best work when they did work — is that philanthropy essentially got to show up and be R&D. And that when those pilot programs were proven, then the government could step up and scale those programs.

So how are you thinking about all of that right now? I don't think the philanthropic sector even has the assets to fill the gap that has been created by the federal policies right now. So are we just in a social impact recession for the time being? Like, how do we get through this?

Jen Nguyen: Eric, I'm one of those people who aligns with the first thing you said, that I believe that if the government worked the way that it should, then we wouldn't need the philanthropic field or sector. And we wouldn't need nonprofit organizations having to step in and fill in basic services. I see that every day on a school level, for instance. But then we also have to acknowledge the reality of the situation where sometimes government, and we're noticing in this administration, they're rescinding federal aid that was previously approved to states. They're making decisions very, very quickly. And so there's this question of, do you trust government to make long-term investments?

But there's a bigger question to me, which is, how did we get to this place? Whether it's the government and the current administration or philanthropy, my argument is that they're both an amalgamation of a bigger challenge, which is the outsized influence of wealthy people in this country. It doesn't matter whatever political affiliation they are, there is an outsized influence of the disproportionate amount of control that the ultra-wealthy have in our electoral system, as well as in some of these initiatives that are being funded that are impacting public systems. I'm one of those people that wonders, what can we do to tip the balance back again to the people? And I constantly wonder what that moment requires. In my opinion, it's a big tent strategy.

The way that I think about ecosystems and the way I think about philanthropy in ecosystems is we as philanthropic entities should not be constraining what we fund. I'm writing about this a lot where philanthropic entities for some reason like to put all these funding criteria on. You have to be an organization of X size serving this, serving that, but it doesn't acknowledge the interdependent nature of organizations to make change. You need everybody: grassroots organizations, think tanks, advocacy organizations, public systems, watchdogs, you need everybody to work together.

The one thing that I would call on philanthropy to do right now is to stop creating the conditions of competition. We also have to figure out how to do that by working together because we have this rhetorical analysis of, these groups need to work together. But the question I have is how are philanthropic organizations and foundations working together? The reason why we've created this crabs-in-a-bucket kind of situation is because we haven't pulled our funds together to create an amount of abundance to make sure that people get what they need from the philanthropic field. So I'm such a yes-and person for the bigger picture of how we can make sure that the disproportionate power is not in the hands of a few, but redistributed back to the people.

Eric Ressler: I love that answer and I think it feels very reflective of the ethos that I feel when I consume content that's coming from you and the Stupski Foundation. And then I also wonder, you have a limited pool of resources, you have your own funding priorities as an organization that are place-based and to some degree tied to the founders of the organization. How do you strike that balance? Because you can't just fund everybody. You have to some degree, you have a lot of resources, but they're still limited. So how do you balance that need to be intentional, strategic, and effective with your investments, but also not overly rigorous? Like, what's that balancing act look like? How do you make those decisions day to day at your work?

Jen Nguyen: It's very difficult. And it varies from person to person at the Stupski Foundation. I think there was recent communication from our organization that we're deploying maybe around 70-ish percent of our remaining assets this year. We've balanced both how to extend our remaining grantees to the very end of our spend-down trajectory, at the same time trying to figure out how we're going to leave a big financial hole in a lot of our grantees' organizational budgets. How do we fundraise for them? That's the more traditional program officer role of trying to support the grantees on our portfolio.

But then there's this other question of sector influence. We're on the way out. I'm the kind of person who I don't think I'm going to work in philanthropy after this. I think I've had a great run thus far. I'm a person without a lot to lose. My organization is going away. I'm going away as a program officer and director, and I probably won't be in this field anymore after two years.

What I'm thinking a lot about in organizational mortality is what kind of sector influence can we be a part of in an effort to make the philanthropic field better? And in my opinion, better to the extent that the field doesn't need us anymore and philanthropy won't exist. So I'm writing a lot. I'm trying to speak a lot. And I'm trying to progress this idea that we should give up control and give up constraints on organizations in an effort to deploy more money that's needed right now. But you're right, Eric. It is a really difficult juggling act, and we haven't quite figured it out yet. I would be welcome to additional conversation about this, because it's a nut that I haven't yet cracked.

Eric Ressler: I think it's one of those problems that doesn't have a solution. The solution is in the everyday work that you're doing and the learning of that. But I am curious to hear, what does a better way look like in the sector? You guys are leading by example in your own way, but if you had the opportunity to wave a magic wand and reinvent the philanthropic sector specifically from the funding perspective, what are the big moves that you would make to change it for the better?

Jen Nguyen: The first thing right off the top of my head would be that the 5% mandated payout needs to be a lot higher. There was a move to 10% in California a few years ago, but that was shot down, unfortunately. The thing that I would advocate for is it needs to be 10% or higher. We need to also have a cultural shift and not put the perpetuity of our organizations before the existence of the public systems and the general systems that we deeply care about. So that would be number one, having a higher than 5% payout.

The second thing that I would advocate for is on a practices level, for us to be less controlling over grantees and really give grantees the creative runway to be able to serve their communities. What I'm imagining is, of course, more general operating support for grantees to make the best decisions for their organizations, but also for us to not just fund basic programmatic services that we think are valuable. That's great. But at the same time, to be able to have our grantees figure out how they can best serve their current constituents. One concrete example is we have grantees who are saying people love in-person services, but we also need to make more technological hybrid offerings for students who feel more privy to chatbotting it, for instance. As difficult as that is as an in-person college counselor, it's something that I have to be more open to at the moment.

The third thing is trying to figure out what are sector-wide incentives for collaboration that get funders in the same region or in the same field to work together more, not just at this learning level. Foundations tend to spin around learning. How much more can you learn? Everybody knows lots of stuff. We need to actually give money out. I do wonder if there's some kind of incentive structure that could be applied field-wide to get more people to come together, because that creates more conditions that are less competitive and more about abundance.

And I also think there needs to be a move for foundations to do more lobbying. There's only one type of lobbying that we can do, and that's about the existence of foundations. We need to see more people trying to change the Tax Act of 1969 that puts us in this 5% mandated payout bind. If we can get more people to lobby because we're legally allowed to do so, I think that would be so helpful not just for philanthropy in having more transformative practices, but for more money to be with our nonprofit organizations.

Eric Ressler: I want to press on a couple things that I hear from our clients who are often at the whim of funders, not like you exactly, but just funders at large. Two of the things I hear a lot, the first is that institutional philanthropy likes to tout that they're very rigorous, evidence-based in their funding practices, research-oriented, learning-based, but often it feels like at the end of the day, funding decisions are still made because of personal relationships and personal networks. What is leading to that? Do you agree with that, first of all? Obviously, it's different for different orgs, but that's what I hear on the front lines a lot, is that they could be qualified, they can do the grant application, and they can send 100 of them out and not be successful, but if they know someone at the org and they can get a personal intro, that's gonna obviously increase their odds. What leads to this dichotomy of saying one thing, but acting a different way in this sector?

Jen Nguyen: Not to get wonky here, but the philanthropic due diligence processes are very flawed. A due diligence process is just trying to do your research about the landscape of organizations to potentially fund. And a lot of times funders just end up talking to other funders. Then that propagates the same organizations over and over again. We've noticed the inequity of funding that goes to very large organizations versus small organizations. At a very concrete level, I'm trying to figure out how we could have better due diligence processes and how program officers don't just talk to other program officers, but they develop a political and community acumen where they can do due diligence with community partners that's not extractive in nature. So that's one really challenging part of the field.

The second thing, Eric, that's really interesting is this idea of rigor. The framework that I try to use for myself is I don't think my job is hard. I think the work is hard. The idea of making sure that every single child in America gets a high-quality education is hard work. My job as a program officer or director is to give out money. That is not hard.

We need to separate those two things and stop putting false rigor, which is basically just barriers to grantees, and stop trying to make this job more than what it is. We just need to give out money more quickly. We need to do so in a thoughtful manner. And again, that requires better due diligence processes. But without those two things, Eric, you're right. People are making decisions based on relationships or as Gen Z likes to say, making decisions based on vibes, quite frankly, which is not a great way to enact social change. It's just vibes.

Eric Ressler: One comparison that I've used before — and people have criticized me on it, but I'm gonna continue to use it — before working in social impact, we were based in Santa Cruz, near Silicon Valley. We did a lot of work in the startup space for B2B and B2C startups. In that world, funders are venture capitalists, and they're looking for a return on an investment. They're looking for exits, IPOs, et cetera. The thing that I noticed though (and I have plenty to criticize for venture capitalists as well) but there was this sense of shared success where they were rooting for their investments. They were doing everything in their power to fund ideas that they believed in and then to support the people that they funded with money, yes, but also with networks, with relationships. And the idea was that they would find these startup organizations when they were really small, and there's a whole subset of venture capitalists that are looking for founding teams and wanting to scale them all the way through IPO.

There doesn't seem to be the same support system and trajectory in social impact. In the B2B and B2C space, you have angel investors, seed investors, A, B, and C round venture capitalist rounds that come in. There's a whole ecosystem and framework and playbook on how to go from an idea to an IPO. Do we have anything like that for social impact organizations? It doesn't feel like there are these clean handoff points where if you're a tiny org, you might be competing for a $15,000 grant to prove out an idea, but then if you prove it, you're back to square one trying to find the next round of funding. Or if you're at $2 million a year, but you really need to be at 15, you have to cobble this together on your own. There's no sense of a round coming together. I know this metaphor isn't perfect, but it feels like we could learn some things from the venture capital world in terms of how we support organizations, not necessarily the incentives behind why we're supporting them.

Jen Nguyen: Eric, I actually think it's a really great analogy because I was thinking about it recently. One of the challenges in philanthropy is our definition of sustainability. I live in Oakland. I don't live that far away from Uber or Lyft in their headquarters. What's really interesting about those entities is they haven't turned a substantial profit yet, but they're still dependent on venture capital to continue operating. But what they've done is cultural change. They've changed the way that we have traveled and what we see as transport that's not taxi-like, which is highly successful.

If you want to take that model, what's interesting is we don't apply those same practices to a social entity. For example, we give one grant and we're like, "Hey, the ultimate indicator of success is if you're able to sustain this money after three years." It's like, if we don't apply those same practices to Uber and Lyft, how are we supposed to apply that same definition of sustainability to an organization that by definition does not make profit? How are they supposed to sustain themselves?

Your analogy offers this idea that we should have more patience and grace for organizations in the same way that society has offered some level of patience and grace to an Uber or Lyft that still hasn't been able to turn that profit, but has been able to transform practices for better or worse on how we travel.

The second thing that's really interesting about what you're saying, Eric, is people are dedicated to the organizations that they fund from the VC side because they see a profit on the other side. They're trying to get to the idea that they could profit at some point and become really wealthy. I'm not going to make a judgment on that. But on the social impact side, we need to have a framework that's similar, that we're so dedicated to these organizations, not because of profit, but because we know the payout is going to be so good for the social good that we care about it. That needs to be a value system that is on par with the idea of a VC trying to profit. They need to be at the same level. And I really don't think that foundations feel that way. They're trying to find the quick hit to move on and say that they solved the problem, even though it hasn't been solved.

Eric Ressler: Totally agree. And it is kind of a head-scratcher. You would think that that would come intuitively. If you're going to be a program officer at a foundation, you would think that you would be largely influenced and motivated by that impact. And you would think that you would understand that these are the most difficult problems in the world that we're trying to solve. To your point, there is no profit model in most cases that's going to make an organization self-sustaining. It's just confounding to me that there doesn't seem to be, when there's such a need and an opportunity for solidarity, emotional support, looking at things in a bigger picture, especially when these orgs are often touting how rigorous and evidence-based and researched they are, you would think they realize that social change takes a long time.

Jen Nguyen: Absolutely, and you use the keyword there: solidarity. We need to be able to value that solidarity.

The other challenge is the philanthropic field is set up to reflect capitalism, competition, to find the best thing, the one intervention that's going to solve everything. It requires a mindset shift of really believing that solidarity is at the level of a VC who's after profit. And I don't know if we're there yet. I wonder how we can get there to know that all of us are working together to envision a community that works for all people.

Eric Ressler: The other thing I want to touch on briefly that I've also heard from clients that we've worked with and just observing the space is that there's also some deeply entrenched, unconstructive norms in the space that have basically been a result of this broken funding ecosystem, at least in part. And those are things like the scarcity mindset, which is more than a mindset. I think that term is a little bit of a misnomer. It is true that a lot of these orgs are underfunded and under-resourced. The mindset is valid because they are actually scarce in resources and overhead and time and energy to do their work.

But what this leads to is this growing crisis of burnout of people being unfairly compensated, working on these important causes. Orgs not having what we call overhead, which is really just sustainable business funding to be able to do the work they need to do, to invest in things like marketing, communications, being able to pay their team and their staff fair wages. Even if you want to look at it from a free-market standpoint, to be able to compete for the world's brightest people who we need on these issues and not on tech and AI. We need to be able to compete with those sectors for talent, at least a little bit more closely than we're able to right now.

I think that some of this does come back to funders not wanting to fund overhead, not wanting to provide general operating support, and this entrenched viewpoint that if you're going to work in the social impact sector, you're going to take a pay cut and that's just the way it is. I'm curious to hear how you all are thinking about that.

Jen Nguyen: The overhead conversation super annoys me because any kind of standard on overhead saying you can't charge 15% on overhead on this grant... do we put the same standard on foundations? Do we have the same stipulation? We don't. And if we don't, then I don't understand why we put that on grantees. There are some exceptions. I totally understand why people would put an overhead cap on an institution that is really large. But for small or mid-sized nonprofit organizations, the overhead is what runs the organization, quite frankly. It doesn't make sense, especially if we don't put those standards on ourselves.

I don't know if a lot of people know this, but that 5% payout that I mentioned earlier, that foundations are mandated to spend out every single year, you can count some overhead from foundations towards that 5% payout, which makes it even more absurd that we want to put some standards on nonprofit organizations but don't put those standards on ourselves.

There's a strange dynamic I can't quite figure it out, where people are annoyed with things like executive director salaries, for instance. It happens here in the Bay Area a lot, where a nonprofit organization says an ED is making $200,000 a year, and people have this pitchfork mentality that it's a lot of money. But one thing that socially we haven't quite figured out is valuing the work that those people are doing relative to, say, an AI executive who's making $250 million. It's this crabs-in-a-bucket mentality without keeping in mind that there are people who are making an absurd amount of money.

I wonder how can we as a social sector control the narrative on the idea of how much is enough to have dignified work, to have talent, and that what is currently happening right now in the nonprofit field is limited and operates on a scarcity mentality. But we don't put those same standards on tech companies. So why are we putting them on nonprofit organizations? And at another level, why aren't we putting them on philanthropic entities?

Eric Ressler: We could talk all day about the shortcomings of some of the structures around funding. I do think it's worth mentioning, there are a lot of really good people in the field who are stuck within these structures, who are doing their best within them. Not to say we shouldn't challenge them, but also worth acknowledging there's a lot of good people who are inheriting some of these long-held structural issues.

I also want to see as we wrap up today if we might be able to help some executive directors and leaders on the practitioner side who are vying for funding, who need funding to do their work. How should they be thinking about attracting and building relationships with funders, especially trust-based funders, in a constructive way so they can escape the scarcity mentality and this cycle of chronic underfunding that tends to happen for some of these organizations, especially when they're first getting started?

Jen Nguyen:

Eric, I know you're asking me to speak to the executive directors of nonprofit organizations, but if you don't mind, I'd like to speak to foundations because I think it's their practices that are causing executive directors to stretch themselves thin in order to fit into the funding requirements of foundations. I'd like to speak to foundations first and then we can come back around to executive directors.

The first thing for anybody starting at a foundation that feels problematic is I think any thoughtful person entering a foundation space should try to stay as sane as they possibly can. That was the best piece of advice that somebody gave me before I started and I would want to offer that advice more widely.

But the second thing is that if you are a CEO of a foundation or even a director or program officer and you want to figure out how you can deploy more money more quickly, one thing I would recommend looking at is spending authorization policies. Those are policies that dictate how much a staff can deploy on their own without board approval versus what the board needs to approve. If there are ways to expand the authorization of the staff, I think that is a good first step.

The third thing we could potentially do here is really ask our boards how much do you need to approve? Can we give most of the authority to the staff? Because what happens at a board meeting is the board ends up approving the slate of grantees that's presented before them anyway. That's a good reflective question to pose to boards.

Finally, it's for us to rethink what a relationship with the board looks like and what boards should be doing. The idea of reading a huge packet of information that's been extracted from grantee time for a board to simply approve a slate doesn't seem like a good use of time. What does a board actually want to do? Is it supporting grantees directly? Is it helping them with their communications, amplification? There are so many more interesting roles for boards. I want to offer that to our field because whatever we do here impacts what executive directors do as well.

For the executive directors, what's interesting is that there's this multi-trillion dollar wealth transfer that's happening over time and it's written about a lot. I wonder if diversifying who you reach out to—that it's not just the institutional philanthropy organizations anymore that's going to be holding the wealth. A lot of it is individual donors who are going to be not starting their own foundations but still writing checks to causes. I wonder if it's time to stack a board full of people who have those networks to be able to answer this concern of this great wealth transfer.

The second thing that executive directors could potentially do is to continue talking and building relationships with foundations, even when that foundation says no, because those nos can become yeses over time. I know it's frustrating because there's so much that executive directors can do other than talking to foundations. But it's happened to me multiple times where somebody stuck around and was like, "Hey, I want to keep talking strategy." And that person eventually became a grantee, to their credit. It does require this level of dogged resilience, which is unfortunate because again, we need to change the philanthropy side so that the executive director doesn't have to do that sort of headhunting of a foundation person. But I wonder, Eric, if there are other questions or other thoughts that you have about what executive directors can potentially do here.

Eric Ressler: Those are great answers. We are seeing a lot of our clients who have traditionally been funded either through the government or philanthropies, who are becoming more competitive, lean in to major donors. That's a whole other set of funding. It's not an easy transition. In my mind, there are some overlapping skills required to solicit funding from those different types of institutions, but there's also a whole different set of skills.

It feels like the gap that is being left by the federal government and to some extent the philanthropic sector is now putting the burden on these organizations to raise money either through individual wealthy people or more and more everyday people who have the capacity to give a small amount, but even that small amount is disproportionately a large gift for them. Often these are people who need the services of these nonprofits. It feels to me like a deeper unfortunate symptom of the same intractable societal inequity that we see around very wealthy people getting more wealthy and everyday people struggling more financially, and then also being asked to foot the bill for the services that they need just to live in a sustainable society.

It seems untenable long-term. I do hope that we see some sort of social and economic correction in more evenly distributed wealth again, but it doesn't feel like we're naturally going to get there based on what I'm seeing.

I'm hoping that conversations like this, and why I was so excited to have you on today, will help. A lot of this gets talked about behind the scenes and not really brought out into the sector, at least enough in my opinion. I was really happy to have you on the show today to talk about that. And before we do wrap up, how can people best follow you, learn from the ideas, see the good work that you're doing, either you personally or at the Stupski Foundation, how can people get involved?

Jen Nguyen: Yeah, Eric, and if you don't mind, I thought of another answer to the previous question. You inspired me, and it's kind of a non-answer in many cases, but what you inspired me to think about is I think we all kind of know what the vision that we wanted to see in the world, which is less wealth inequality. I mean, indeed, there are grander visions of course, but let's say that that's sort of the north star here.

What is the bigger question right now is what do we do in the interim in this messy period of time? And one thing that I want to depend on is the thoughts of people who are in the field already who are doing the messy work.

And so there's this idea that I have of really wanting executive directors to create that visionary space for themselves to be able to dream into the future and to be able to protect that imaginative space as much as possible. And I know this feels really philosophical, but I think it's really, really important for folks to be able to operate on the day-to-day, but also hold that space to strategize in the moment. And this is a call for philanthropy to fund those spaces, to give people sabbaticals and weeks to be able to dream. I think that's required for us to make it to the other side of this current moment. And one thing that working at philanthropy has done, it's given me the time and the space to be able to do that dreaming as well.

To answer your other question on where you could follow Stupski Foundation's work as well as my work, you can go to the Stupski Foundation website, stupski.org. There's a ton of links to all the different communications that Glenn, our CEO, puts out, as well as a column that I write called "Philanthropy Confidential," where people can submit confidential or anonymous questions, and I'll candidly answer them through email on a quarterly basis. It's been a lot of fun seeing all the different questions. Both Glenn and I have Substack accounts that you can also follow. But in general, we're on all the social media platforms with the exception of the platform formerly known as Twitter. You can find us on most social media platforms at the moment. And we hope to continue to be in conversation with folks, including yourself, Eric.

Eric Ressler: Awesome. Jen, this was so great. Thank you so much for coming on today.

Jen Nguyen:

Thank you so much for having me. I really appreciate the conversation.

Key Takeaways

• The "Rainy Day" is Now: The sector's tendency to save for a future crisis ignores the urgent needs of the present moment.

• The Goal: Let Nonprofits Do Their Work: The core principle is simple: nonprofits should spend more time with their communities and less time with funders.

• "False Rigor" Creates Barriers: The job of a funder is to give out money. Complicated processes and "rigor" often serve to create unnecessary barriers for grantees and make the funder's job seem harder than it is.

• Decisions are Based on "Vibes": Despite claims of being evidence-based, many funding decisions come down to personal relationships and networks, not objective analysis.

• Rethink the 5% Payout: The mandated 5% payout is insufficient and should be raised to 10% or higher. Foundations should also lobby to change the laws that lock this in.

• The Overhead Double Standard: Funders impose strict overhead limits on grantees while not holding themselves to the same standard.

• Fund Visionary Space: Philanthropy should fund sabbaticals and protected time for nonprofit leaders to dream and strategize for the future, which is crucial for navigating the current reality.

• Stupski Foundation: spend-down foundation where Jen is the Director of Post-Secondary Success.

• The Atlantic Philanthropies: The foundation founded by Charles Feeney, who Jen mentions as a major inspiration for Joyce Stupski's decision to create a spend-down foundation.

It’s brutal logic. And it’s logic that deserves to be challenged.

What if there’s another way? A different economic model, one that doesn’t see tradition as something to be destroyed but as a foundation to build on. A model that refuses to accept that leaving people behind is the cost of doing business. It’s an economy built not on destruction, but on care.

You might call it artisan economics.

To explore what that looks like in practice, I wanted to talk with someone who has dedicated her life to proving this counter-model can work.

My guest today is Stacey Edgar. She has been a social worker, founded a multi-million-dollar fair trade social enterprise, and is now the Executive Director of the International Folk Art Market — the world’s largest folk art market. She’s seen firsthand that a more humane, more connected, and more sustainable way of doing business isn’t just a theory of the future. It’s already happening all over the world, and it has been for quite some time.

In our conversation, we explore what artisan economics can teach us about building a more equitable and connected future.

Interview

Eric Ressler:
Your career has been anything but conventional. You grew up in small town Illinois, and now you’re leading the world’s largest folk art market. You’ve been in social work, founded a social enterprise, taught at the university level, and are now a nonprofit executive director. How did that trajectory happen, and how has it shaped your experience in this sector?

Stacey Edgar
It’s funny because I don’t think anyone would ever plan a career path like mine. When I taught at the University of Colorado at the Leeds School of Business, I used to tell students there is no career ladder — there’s a career jungle gym. You go from one piece of playground equipment to another, following your curiosity.

That’s what happened to me. I was a social worker working with women and children, helping moms in welfare-to-work programs around the time Bill Clinton’s TANF program was in place. Meanwhile, my father-in-law was a two-time governor in Illinois, and when he left office, he and my mother-in-law joined boards with the UN World Food Program. She met women selling handcrafts while visiting food distribution sites and brought their work back for me and my sister-in-law. I thought, I know women who would love this stuff — and want to support these entrepreneurs. That’s how I started Global Girlfriend.

Seventeen years running a social enterprise was like an MBA. After that I ended up teaching, and eventually I came to IFAM — an organization I had admired for many years.

Eric Ressler:
Was there a specific story or encounter that made you take the plunge and turn a $2,000 tax refund into a multimillion-dollar social enterprise?

Stacey Edgar:
It was really two stories combined. After 10 years in social work, I had worked with so many women in the child welfare system who were young mothers flagged for neglect. But often, they didn’t have childcare, job opportunities, or training. It wasn’t neglect — it was lack of safety nets.

Meanwhile, my mother-in-law was meeting women entrepreneurs abroad facing the same challenges. Across Africa, 76% of women still work in the informal sector — no protections, no safety net. One story that stuck with me came from the Gemini Trust in Ethiopia, which supported moms of twins. At the time, famine meant many mothers were losing one of their babies because they couldn’t feed both.

Those experiences — in the U.S. and abroad — lit the spark for Global Girlfriend.

Eric Ressler:
When you were growing Global Girlfriend, what were some of the key lessons, obstacles, or mistakes? What do you wish you had known starting out?

Stacey Edgar:
One of the biggest joys was how open people were to the idea. We partnered with Whole Foods, West Elm, Target.com, even Neiman Marcus — all because people wanted to support artisans. My first advice is: just ask. You’re not making a sale, you’re inviting someone to be part of a movement. That was really fun. It was really fun to see how many people wanted to join in that.

On the flip side, there were hard lessons. Social workers don’t know much about importing. My first large shipment wasn’t tagged correctly and U.S. Customs said they would burn it. They didn’t — but gave us three days to relabel everything. There were lots of basic business learnings like that. Today, there are far more resources available, whether or not you’ve gone to business school.

Eric Ressler:
After Global Girlfriend, you shifted into academia. How did your social enterprise experience influence your teaching? And how did teaching change your perspective as you moved forward?

Stacey Edgar:
I guest lectured for eight years in a class called Business Solutions for the Developing World (since renamed). When I was leaving my brand, they asked me to teach it. The course didn’t fill that semester, so they offered me another one instead — BASE — a hands-on business practicum. Students worked on things like internal rate of return and weighted cost of capital. Social entrepreneurs don’t always dive into those details, but they matter. Profit is the fuel for purpose.

I went on to teach the Business Solutions course, where students worked with companies worldwide — artisan groups, agriculture projects, tech. Seeing them apply business knowledge to real-world contexts was amazing, both for students and entrepreneurs.

I also taught World of Business, an intro to political economy. That course revealed how few women, people of color, and Indigenous voices are included in core economic texts. If we want people to see the world as a whole, we have to look at the whole world. That realization is a big driver for me now — including in the book I’m working on, which looks at what gets discounted in the global economy, like care.

Eric Ressler:
Tell me about your transition into IFAM. This is a nonprofit with a 20-year legacy and a different model than your past work. What surprised you about stepping into this role?

Stacey Edgar:
I’ve always thought of myself as collaborative, but when you run a small brand you’re flexible and do what you want. Running a nonprofit with a board is different. IFAM has nearly 50 board members plus 1,500 volunteers. Becoming a better listener and managing diverse stakeholders was a learning curve. I used to teach stakeholder vs. shareholder theory, but now I live it. At IFAM, stakeholders include artisans, community, volunteers, board, donors, and shoppers. It’s a lot to balance — but the collaboration is worth it.

Eric Ressler:
You’ve talked about resilience in leading organizations. How do you think about resilience in this moment, when the sector is under pressure from funding cuts and political scrutiny?

Stacey Edgar:
Running an international market is always challenging. This year we had 57 invited countries — meaning visas, shipments, customs. On top of that, there were country bans and tariffs. Some artists were afraid to travel or worried about detention at customs.

Despite that, volunteer numbers went up, and we hit record sales — $3.88 million in three days and three hours, with over 20,000 visitors. The economy isn’t great, inflation is high, there was a 10% tariff. But people still showed up. Not because they needed to consume, but because they cared about person-to-person diplomacy. That resilience — from staff, volunteers, and artists — was inspiring.

Eric Ressler:
You’re working on a new book, Artisan Economics. What themes are you exploring, and how do you see the state of purpose-driven business today?

Stacey Edgar:
When purpose and mission become your marketing, you go past the core — which is doing the right thing for the right reason. Artisan Economics isn’t a how-to-build-a-business book. It’s about choices we all make, and how the artisan economy works opposite the mainstream economy.

Joseph Schumpeter talked about creative destruction — the idea that progress requires destroying the old. But in the artisan economy, creativity builds on itself. It doesn’t discard tradition, it builds forward. He also talked about the paradox of progress — that some people will be left behind. But artisans don’t leave people behind.

A story I love: Mercedes and Nati, a mother-daughter team in Peru, run a cooperative employing 800 women in the Andes. When one small community they worked with was suffering from anemia due to a poor harvest, they didn’t wait for someone else to fix it. They carried vegetables up the mountain through storms until the community recovered. That’s a culture of care — and it’s what we need more of across the economy.

Eric Ressler:
“Culture of care” is a phrase I’m hearing more often in movements. What does it mean to you?

Stacey Edgar:
From a feminist perspective, and in my PhD research reflecting on 17 years of social enterprise, one thing is clear: there is no country that treats women equally. And for anyone who is transgender or non-binary, it’s not even close. Until the 1970s, women’s labor wasn’t even recognized in the global economy. The women-in-development movement began when a researcher pointed out that women were doing most of the work in Africa and India and no one noticed.

Still today, 76% of women across Africa work informally — with no recognition or credit. Add to that all the unpaid care work globally. Some countries, like Norway or Denmark, are better — high taxes but strong cultures of care. Bhutan was eye-opening: gross national happiness is their measure of development, 60% of land must remain forested, and if you build a house you must replant the trees used. That’s care for the environment, the ecosystem, and the people.

Eric Ressler:
Leadership can be lonely. Where do you turn for inspiration and strength when things get hard?

Stacey Edgar:
It does get tough, and you don’t always do the right thing. You do what you think is best, and sometimes there are unintended consequences and you have to shift. That happened when I merged with a larger company. For me, resilience comes from peers — other leaders in the artisan space. I lean on their expertise and friendship. I also rely on my family and friends. And I try to take care of myself through reading and yoga — though not always as well as I should.

Eric Ressler:
We’ve talked about social media becoming more performative, less connective. How do you think about showing up digitally in ways that create authentic connection?

Stacey Edgar:
We all get on social platforms because we want to connect. And they do give us global reach. But I feel like our biggest personal poverty at the moment is disconnection — from the things we buy and how they’re made, from one another in the rat race of work. Finding ways to connect more authentically is something I think about a lot, and it’s what artisans want too.

At IFAM, you meet the person behind the work. That’s my favorite part of my job — I’m not always the intermediary. It’s person-to-person connection. Platforms like Substack are meant to do that too, but they can get performative. We all need to be more intentional — reaching out to people we find interesting, having real conversations. That’s where connection happens.

Eric Ressler:
As we wrap up, what are you most excited about in the near and medium term?

Stacey Edgar:
I’m excited about the book, though it won’t be out until 2027. And I’m excited about where IFAM is going. We’ve been grassroots for 21 years, but we’re at a peak moment to show the world the importance of this space. At a time when people worry about an AI-driven future and loss of authenticity, I think global creativity and cultural exchange matter more than ever. The more authentically we can represent those, the better.

Eric Ressler:
Where can people follow you and IFAM?

Stacey Edgar:
Visit folkartmarket.org to learn about our organization. Follow IFAM on Instagram and Facebook. Personally, I spend most of my time on LinkedIn for professional updates. If you want family news — like wedding pictures of my kids — that’s on Instagram.

Takeaways

1. Connection as wealth: Poverty isn’t just lack of money, it’s disconnection — from each other, from culture, from the story behind what we consume.

2. Artisan economics as an alternative: Instead of creative destruction, artisans build forward while preserving heritage and including everyone.

3. Resilience as practice: It’s not about perfection, but adapting to challenges while staying true to purpose.

4. Values over Cause Marketing: Mission and marketing aren’t separate. Lived values create deep trust and loyalty.

5. Women at the center: Empowering women artisans transforms not only individual lives but entire communities.

Stacey Edgar’s journey proves that another economic model is not only possible — it already exists. One built on care, connection, and creativity. One where no one is left behind.

Listen to the full interview below, or find it on YouTube or your Favorite Podcast App.

How does real change happen?

That's a question I've been wrestling with lately. When we look at our biggest problems, what are the most effective levers we have to pull?

The first and arguably the most important is government. The idea that we create change together through our public institutions. But that belief is being tested right now — not because the idea is wrong, but because there are deliberate efforts to reshape the very theory of government happening in real time. We see agencies being dismantled, budgets being slashed and disinformation being sown. And when the government is sidelined like this, it makes it impossible to deliver on its promise.

Then there's the free market. The argument that change comes from competition, from innovation, from the power of business. That where government fails, the free market has better and more efficient solutions — as long as there's money to be made in the process.

And then there's us. The third way. The social impact sector. Here to take on the problems the first two sectors are unwilling or unable to solve. But our sector is exhausted. And right now it's struggling.

But what if the answer isn't about choosing one of these levers? What if the real engine of change is something more fundamental? A force that underlies all three of these paths but isn't about policy, or profit, or programs — it's about people.

To explore what that looks like in practice. I wanted to talk with someone who has put this theory into action at a massive scale, and that person is Amanda Litman.

Amanda is the co-founder of Run For Something, an organization that has recruited over 225,000 ordinary citizens to run for office and helped more than 1,500 of them win.

And her latest book, When We're In Charge, charts a new course for leadership and our relationship with work.

In our conversation, she answers the very question I've been wrestling with:

In a digital culture that feels increasingly transactional: How do we build authentic human connection? And how do we focus that connection on powering meaningful social change?

Full Interview

Eric Ressler: Amanda, thanks for joining me today.

Amanda Litman: Thank you for having me, Eric.

Eric Ressler: To start, I’d love to hear how you think about social change in this moment. Not just politics, but broadly. In your view, what’s the most effective path to creating the change we need?

Amanda Litman: I think there are lots of different avenues for social change, which sounds like a mealy-mouthed answer, but I think you need all of the different avenues in order to actually get progress. So I think there's obviously electoral. That's the work that I do at Run for something where you're trying to get people elected who can be different kinds of decision makers, who can move the needle, especially on the local level, cities, states, counties, that kind of thing.

I think business leaders can have a really big way to make a difference in people's lives. I had a book come out in May about called When We're In Charge, about people leading differently, and one of the arguments I make in the book is that if work sucks less, it creates more time for people to be better partners, parents, friends, citizens, community members, and that that can actually transform society if enough business leaders operate in that way.

And I think there's ways in our relationships with one another that we can move things forward. Thinking about how to be a better friend, how to be a better parent, a better partner, which if we are all making collectively little decisions in service of that, it adds up to something big.

Eric Ressler: You’ve written about “casual hosting” on Substack, and it really stuck with me. I’m also a parent of young kids, and I’ve seen my social life shrink because of it. How did you come to this practice, and what has it meant for you?

Amanda Litman:

So like most good things in my life, it's because of my husband. My husband is a therapist. He works in mental health all day long. He was listening to some podcast, I think at the end of last year. My second daughter was born in September, so right now I have a two-and-a-half-year-old and a 10-month-old. We're deep in it.

We were at that point still in the newborn trenches, and he was listening to some podcast and they were talking about Shabbat dinners — hosting people every Friday to have them around your home, and the beauty and the tradition and the ritual of that.

He got it in his head that he wanted to do something similar, but with two little kids with busy jobs. The idea of Friday night felt unimaginable. Kids go to bed pretty early. Thank God. So we decided that he was going to make a New Year's resolution to host people at our home every Saturday in 2025. And I thought this was absolutely insane. I was like, alright baby, whatever you want to do, I'm down for a good time. But we can try. We have since done it.

Every Saturday in 2025, we have either hosted people for dinner or gone over to someone else's home for dinner a couple times.

Once or twice we did it on Sunday — for Passover, we had a Seder on Sunday instead of Saturday. But every weekend this year, we've had time with adults and occasionally little kids to eat, to hang out.

And what we've learned is that it's both transformative for our social life, way lower stakes than you need it to be, and so meaningful to take people from acquaintances to friends, which is the hardest thing to do I have found as an adult, especially as an adult with little kids.

Eric Ressler: I’ve been thinking a lot about how digital culture shapes real-world connection. We’re in a strange moment—the platforms are shifting, the promise of connection often feels hollow, and polarization is everywhere. How do you navigate that landscape and still build authentic relationships?

Amanda Litman: Especially when you're in the trenches with little kids, it's really hard to be in person. I'm at the whim of my daughter's nap times. So I think about how I'm using my group chats. How am I engaging? It's okay for some of my friendships right now to be weak ties that are DMs over Instagram or sending memes and TikToks back and forth. That's not a replacement for a friendship, but that's okay if that's what the friendship is right now. Understanding that it has to be something more later.

One of the things that I am really, really careful about, especially in this stage of my life, is making sure that I am not letting things go unanswered, which I know can be very easy for things to fall through the cracks. If I get a text message and even if I can't answer it immediately, I try to remember to answer it later. If I get an email, I try to work through my inbox really quick.

If I get a DM — not a point of pride necessarily — but I know how frustrating it is to be on the other side of that where you send the text and it never gets answered and then you're like, well, do I double text? Do I triple text? They actually don't want to talk to me at all. It's never personal, but it feels personal. So I'm careful when people are extending bids for connection to try and take them and return that as much as I can. It's so hard though. It's so hard.

Eric Ressler: It is hard. One of the things making this so hard is just the sheer volume of information each of us is exposed to as a normal human being in our modern culture. It's unreasonable. It's incongruent with our psychology and our capacity as humans. As a leader of a movement, of a nonprofit, of an organization, how do you think about actually growing your reach in a meaningful way to make your mission come true?

Amanda Litman: I think a lot about what can I do to make it easy for people to say yes, which is kind of the same thing we're doing with dinners where we just say, come over at 5 o'clock. Here are three Saturdays that are available. Which of these works for you? If not those three, how about these three? Now, the work that we do at Run for Something — asking people to run for office — is an incredibly challenging thing. Our job is to ask as many people as we can and then make it really easy for them to say yes.

We do that through digital tactics. We do that through onboarding. We do that through resource generation. I do that through accessible communication.

What can I do as an organization or as a leader so that if I'm asking someone to do something, it's so easy for them to satisfy that?

It feels intuitive, but you'd be surprised — maybe you wouldn't — how many times you get an email and think, I don't know what you're asking me to do here. I want to help you, but I don't know what help looks like, and if I don't know what help looks like, I can't provide it.

Eric Ressler: Yeah, I mean, this is the "hey, can I pick your brain" kind of email that you might get, right?

Amanda Litman: I hate that, which I feel bad because sometimes people send me those. I've written — in the book, in Substack, whatever — don't pick my brain. Ask me a specific question and I will give you a specific, concrete answer. Picking my brain is not fun for me, and it's not going to be helpful for you.

Eric Ressler: It also feels like when you get a request like that, you don't know what you're even really saying yes to. The motivations can be unclear. I've been thinking a lot about fundraising tactics, more from the nonprofit space, but also in the political world. Fundraising has become tragically transactional and broken. I see this on both sides of the aisle — I get text messages from every side you can imagine. No one's winning there, in my opinion. There are rare exceptions.

Can we do this in a more constructive, authentic way, but still raise the funds we need to? We're in a moment where funding is falling short for a lot of social impact organizations — fallout from federal funds evaporating, USAID being spun down. Many causes we work with are not only short on funds; some lost funding out of the blue with no planning. Fundraising is more competitive than it's ever been.

How are you thinking about fundraising in your world and, more broadly, how can we bring people together for these movements in a way that's constructive — not extractive or transactional?

Amanda Litman: I've been thinking a lot about this because my original career entry point was in digital fundraising. My first job was doing online fundraising for Barack Obama's presidential campaign in 2012. I did the same thing in 2014. Then I ran Hillary Clinton's email program, which was asking people for money and to volunteer and engage in other ways — primarily grassroots support. I remember in 2012 running an experiment on our email list testing, was there such a thing as too much email?

One of my jobs for two months was that every day I was responsible for picking the two or three emails we were going to send that day and sending it to an additional test group and a control group to determine: was there a limit to how many times we could ask people to give? What we found in that experiment — this was 2012, over a decade ago — more email meant more money even when you factored in unsubscribes. And if our job on the campaign was to raise the money to help win, that was worth it, even if people complained.

We were thoughtful and careful about the tactics we used as part of those emails. We were intentional about making emails sound like the voice they were coming from. We thought about treating supporters with respect. Our guiding ethos was to never treat the list like an ATM. Over the decades since then, people and programs have internalized "more email means more money" — you ask more, you get more — without remembering the treating people with respect part.

Run for Something does not run a program like that. We email people for money regularly because we're doing work that deserves to be funded, but not every time, not every day. I am rigorous about the kinds of things I approve. Sometimes we do things and I'm like, we need to scale that back next time.

I think it's important because we're trying to build something long-term and sustainable, and that means we want our supporters to be with us for the long-term. I can't burn those bridges.

Campaigns have a very different mindset, and nonprofit groups can have a very different mindset. One of the tensions is that if you aren't putting your foot to the fire for your small-dollar fundraising — email, social, text — the money has to come from somewhere else. And right now, it's not. Major money — foundations, institutions, major donors — is also not really moving in a meaningful way.

So we're at a standstill. I still don't think that's an excuse to treat supporters like crap, but I understand the motivation for these organizations to do so. It's a big conversation among the Democratic left and the broader nonprofit sector: how do you do this in a way that sustains the work and the relationship?

Eric Ressler: I want to touch on that a little bit more deeply because I've thought about this parallel between what I've observed with political candidates and their campaigns and how they fundraise versus the nonprofit sector. I always chalked it up to this: at the end of the day, these folks need to raise as much money as quickly as they can.

At the end of that, they either win or they lose the campaign. And so they can — to put it bluntly — afford to burn some bridges if that means they might win. I don't think that's ever been true for nonprofits. And I think that mindset, to your point, has spilled over into the nonprofit space — fake urgency, negativity bias — tactics that make me feel icky, even from candidates or groups I support. Their reputation is tarnished because of how they're fundraising.

Is that coming back to bite us now? This decade-plus of fundraising that way, in a way that's tarnished the brand, where a lot of supporters feel like ATM machines?

Amanda Litman: 100% — if you've been telling supporters for a decade "the sky is falling, kiss all hope goodbye," and then the sky does fall, what do you do? What was it for? It feels like we've been gaslit. I also think many of the tactics that many of these organizations and organizers are using — it's just lying, and I don't think there's ever a good reason to lie to your supporters. The ends never justify the means on that front. Kind of a hot take maybe, but I think it is worth being really on the level with people.

If you are doing work that is good, if you have a story to tell that is honest and true, if the impact is clear, then you should be able to raise money telling that story.

There's "supporter record" — like, oh, you haven't given yet this year. I think that's fine within reason. There are ways to do that respectfully. But the 400X match happening today, deadline tonight, surge the money to XYZ, and trying to raise money off a thing not related to your work — no. It's shitty.

It treats people like crap and they deserve better than that, and it's emblematic of how voters in particular feel about the organization — like the Democratic Party's brand. They feel like they've been told "we're fighting, we're fighting, we're fighting" — are we? Is this what fighting looks like? Doesn't seem like fighting to me.

Eric Ressler: Let's tie this into one of the other big topics you're talking about a lot right now — the generational change in work culture. What do you think is behind the cultural shifts happening right now? What are you seeing and hearing as you're writing this book and out there in the world?

Amanda Litman: In 2030 the youngest boomer is going to hit retirement age. We are already seeing now, per a new Glassdoor survey, millennials are now a majority of all managers. Gen Z makes up one in ten of all managers. Fortune 500 boards and companies are passing off from boomer CEO to millennial CEO. They're skipping over Gen X entirely — sorry to Gen X. It is a lived reality that we are about to have a generational passing of power.

And I think it's going to look and feel very different.

Millennial leaders are showing up with a very different relationship to institutions, to mental health, to work-life balance, to transparency, to authenticity, to social media. They're thinking very differently about the responsibility of the workplace to the employer and the responsibility of the leader to model that — to model the kind of behavior they want to see.

A lot of this got accelerated because of COVID. The shift to remote or flexible work probably would have happened eventually anyway, but COVID put gas on the fire in a way that meant all of a sudden you had executives trying to manage teams remotely or flexibly and not really knowing how.

Those who have grown up online — cultivating friendships over group chats, on online forums since we were teenagers — understand which gifs are right to use in which moment; think about emoji as part of communication style; and what it means to show up over a video chat and have executive presence. That comes more naturally when you've been doing it your whole life. As Millennials take power, you'll see downstream effects in the workplace be very different — and when work sucks less, things open up more outside of it.

Eric Ressler: On that note, some of the fallout from the last election cycle — there was a lot of Monday morning quarterbacking around "the left doesn't understand new media" and that was the Achilles heel that lost the campaign. Without getting into that toxicity, how do you think about new media fitting into these causes, to your cause, in a responsible way? How important is it to understand how culture is happening digitally if you're behind one of these missions right now?

Amanda Litman: So funny you use the term "new media" because when I got started in politics 15 years ago, New Media was the name of the digital department. It's not new anymore.

What’s different now — and a challenge for organizations — is that organizations cannot really further a mission. A person can. A personality can. Perhaps an organization with a strong point of view or a compelling character can advance an effort, but you kind of need a person.

I think one reason Run for Something has been able to succeed up till this moment is because I have put myself out there as a person telling a story. I've had to operate a little bit like an influencer, a non-influencer. I'm an operative and executive — it's not the same thing.

But I think about how to use my personal voice and point of view to advance the organization's mission really thoughtfully. Even the fact that I have a personal Substack and I write about parenting and books and also politics — that's an intentional strategic choice as part of my communications efforts for the organization as well as for myself.

If you don't have an executive who is comfortable putting themselves out there in that way, it can be really hard to break through in this media environment. You can't do a 45-minute podcast interview where you only talk about the organization or pivot back to kitchen table issues. You have to be willing to be a person. We're in a moment where personality drives things, persona drives things. Brands don't — unless they can find the persona within them.

Eric Ressler: I've compared this year at times to how it felt going into COVID, where everything became contracted and paralyzed. I'm starting to see some motion away from that. I imagine you've had a tough year in your own ways. Everyone has. How do you keep going when things are hard and feel impossible? What keeps you energized around the work?

Amanda Litman: The work itself is really forward-looking. I'm lucky and grateful that I created a job for myself where I get to focus on the future. We've had more than 60,000 people sign up to raise their hands to say they want to run for office this year. That's more than we had in the entirety of Trump's first term. We're very close to it. We're probably going to exceed that number by September. It's huge. Those are people willing to change their lives and careers to ultimately change the world, and I'm grateful they're willing to reach out to Run for Something for help to do it.

I'm also lucky that I have two very rambunctious children who keep you grounded whether you like it or not. It's hard to think about the bad things happening in the world when your toddler is screaming, "Mama, help me tuck in my monsters," and the baby is just giggling as second kids do. The final thing I would say is being really thoughtful about my news consumption.

I read a lot of news — it's my job — but I try to only drink the poison I have the antidote for. I focus on the Democratic Party, congressional stuff, all the races we work on. I read a lot about New York City politics because as a NYC voter I can do something about it.

If you drown yourself in the flood of information every day, you will never catch your head above water. It's okay not to know everything going on at all times — as long as the things that you do know about, that you can take action on, you do.

Eric Ressler: My podcast co-host Jonathan Hicken, who's an executive director at a nonprofit, has described this as knowing your sphere of influence and acting within that. I think that's an interesting tie-in to what you're doing with Run for Something, because it's been a seed-sowing organization — coming down-ticket up and growing off of that. How did you first come up with that strategy and how does that tie into your philosophy on this work?

Amanda Litman: I worked for Hillary for two years — gut-wrenching. About a week after election day, I started hearing from people I'd gone to high school and college with: "Hey, Amanda, I'm a public school teacher in Chicago. I'm thinking about running for office. If I want to do this, who do I call? What do I do?" At the time — November 2016 — if you were young and you wanted to do more than vote and volunteer, there was nowhere you could go that would take your call. That felt like a symptom of big problems in the Democratic Party and our democracy. So I reached out to a bunch of people with an idea: what if we solve this problem?

One of those folks became my co-founder, Ross Morales-Rochetto. We wrote a plan and built a website and then launched Run for Something on Trump's first inauguration day, thinking it'd be small. We thought we'd get 100 people in the first year.

Eight years later, 225,000 young people have raised their hands to say they want to run. We've helped elect more than 1,500 across 49 states plus DC. At this point in 2026, there will be dozens running for higher office — Congress, Senate, governor, secretary of state, treasurer — who have come through our pipeline. They are the present and future leaders of our party and our country. It's exciting to see that pay off.

Eric Ressler: Amanda, thank you so much for today. Before we wrap up, how would you like people to get in touch, to support, to follow you? This is your time to plug anything you want.

Amanda Litman: I am all over the internet — either Amanda Litman or Amanda Lit — on social. I post too much. You can find me on Substack: amandalitman.substack.com. And you can get my book, When We're In Charge, which is a next generation's guide to leadership. Available wherever you get your books — audiobook, ebook, hardback.

Eric Ressler: Awesome. Thank you so much, Amanda. This was great.

Amanda Litman: Thanks, Eric. This was fun.

Key Takeaways

• The fourth lever is people. Durable change comes from distributed leadership—not savior narratives.

• We’re mid–generational transfer. Millennial/Gen Z leaders are rewriting norms around mental health, transparency, and work-life boundaries.

• Culture is infrastructure. If work sucks less, people have more capacity to be better partners, parents, neighbors—and citizens.

• Play the long game. Treat supporters with respect. Don’t burn bridges. Sustainable fundraising > panic-driven tactics.

• Leaders must be people, not just brands. A clear personal voice can advance a mission—when used thoughtfully and authentically.

• Act within your sphere of influence. Curate inputs, protect energy, and take action where you can actually move the needle.

• Democracy is built locally. Recruiting and electing everyday people to local office compounds into real power over time.