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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Everyone claims to be strategic. But what does that word even mean anymore?

In this episode, Eric and Jonathan dig into a question that comes up constantly: what actually separates strategy from tactics, and why do so many strategic plans end up collecting dust? Eric makes a bold claim: that strategy, at its core, comes down to one word: conviction. Strategy is not frameworks. Strategy is not 200-page slide decks. Strategy, at the end of the day, is having clarity and conviction about who you are, and more importantly, who you are not.

The conversation gets personal when Eric admits he lost that conviction at Cosmic, drifting toward service expansion before recognizing the pattern he’d seen in dozens of client organizations. Jonathan pushes back, pressure-tests the idea, and shares his own experience applying this thinking at the Seymour Center.

If you’ve ever sat through a six-month strategic planning process that ended in a fizzle, this one’s for you.

Notable Quotes

Eric [00:04:30] “There is a very strong conviction about who they are, but even more so who they are not.”

Eric [00:04:45] “Strategy is mostly about what are you saying no to versus what are you saying yes to.”

Jonathan [00:07:03] “I’ve been in a number of boardrooms on a number of strategic plans, and the impulse I find for most people is to go tactical. And to call it strategy.”

Eric [00:07:43] “It’s like trying to build a house without understanding what you’re even building. You might have a bunch of plans for the drywall and the framing and the tiles — but no one even knows why they’re building it.”

Eric [00:10:00] “I see this happen with the orgs we work with and I was blind to it for a long time — sort of like frog in boiling water.”

Jonathan [00:15:15] “My professor described photography as an extractive art rather than an additive one. When I’m saying no to things, I’m taking a photograph and excluding everything except the only thing I want to see.”

Eric [00:16:06] “The near enemy of conviction is having that conviction work in a moment in time and then never evolving. The conditions change, the sector changes, and you stay stubborn. That’s the near enemy.”

Eric [00:25:47] “The longer your strategic plan is, the more useless it is. 90% of strategic plans don’t actually matter and don’t actually get used by organizations.”

Eric [00:28:58] “Passion is not a strategy. It’s an important element. But you need conviction that not only do I believe in the mission, but I have a deeply held belief that this is how it should be done.”

Eric [00:29:22] “You can take any framework in the world, any approach — and if you don’t know what to say yes and no to, you don’t have a strategy.”

Resources & Links

• Good to Great by Jim Collins

• Minimum Viable Strategy episode

• Email the show: podcast@designbycosmic.com

Thanks for reading Designing Tomorrow! Subscribe for free to receive new posts and support my work.

Full Transcript

Eric Ressler What the fuck even is strategy?

Jonathan Hicken Does that word even mean anything anymore? I think strategy is a set of decisions that have good reasons behind them that you turn into action.

Eric Ressler If I had to choose one word to summarize everything, it would be conviction.

Jonathan Hicken You’re saying that there’s a hard separation between strategy and tactical execution.

Eric Ressler Strategy is mostly about what are you saying no to versus what are you saying yes to? And the longer your strategic plan is, the more useless it is. I’m Eric Ressler.

Jonathan Hicken I’m Jonathan Hicken.

Eric Ressler And this is Designing Tomorrow. Jonathan, today I want to talk about something that comes up a lot in my work and I think it comes up in your work too. I know it does actually. And let me kind of set the stage here a little bit. So sometimes people reach out to us to work with us and they ask a question that I find kind of interesting and a little bit funny too. And the question is, do you guys do strategy?

Jonathan Hicken Do strategy. Yeah.

Eric Ressler And every once in a while I have this kind of sick urge to be like, “Oh no, we don’t do any strategy work. We just tell us what you want and we’ll just make it happen.” Which is obviously kind of silly. But I think the reason people ask that is because what the fuck even is strategy?

Jonathan Hicken Does that word even mean anything anymore?

Eric Ressler Right. So I think I’m hoping today we can break down what does strategy even mean? What does strategic thinking mean? How does that loop into what we call in the social impact space commonly strategic planning? And how do we do that better in a way that’s actually constructive? I know you do a lot of this work at the Seymour Center. I do a lot of this work through our client work at Cosmic. So what do you think? Should we send it?

Jonathan Hicken Let’s get into it.

Eric Ressler Okay. So I want to ask you, what the fuck even is strategy, man?

Jonathan Hicken Man, okay. I think strategy is a set of decisions that have good reasons behind them that you turn into action.

Eric Ressler Okay.

Jonathan Hicken That’s what I’m going to put on the table as the starting position.

Eric Ressler All right. So those are your chips.

Jonathan Hicken That’s my opening bid.

Eric Ressler So okay, here’s how I’ve been thinking about this. I think there are a lot of flavors of strategy that all get lumped into this one word and they’re all different and they all serve a purpose. I think it also gets conflated with tactics, like tactics and strategy. So I’ve been thinking about in prep for this episode, just like as a little background, we do a lot of strategic work, quote unquote. There’s no agency in the world really that’s going to say they’re not strategic. And at the same time though, there’s a lot of agencies out there that are like, “Oh, we’re different because we’re strategic.” And it’s like, well, who’s going to claim they’re not? But that doesn’t mean that everyone actually is strategic. And the longer that I’ve been doing this work, the more I think our work really is strategic. And it’s really made me think about like, what does that even mean? How is that different than us just being creative only or us just being tactical only? And so I really started to kind of try and think deeply about this. I’ve read different authors and there’s all kinds of strategic frameworks out there.

You think about some common ones like the theory of change, right? Strategic planning processes. There’s a million frameworks for how to do that. We’ve talked about that before. By the way, I think we are slowly building an anti-audience of strategic planners who secretly hate us because we kind of talk shit on strategic planning on this show more than I think I mean to, but let’s just do it.

There’s also brand strategy, right? How is that different than strategic planning? There’s work that you do around building a case for support that’s highly strategic. So there’s all these different flavors of strategy, but I started to think about like, what is it that is similar about all of that kind of work? And there’s a couple themes that come up for me, but I’m going to put my chips on the table.

Jonathan Hicken Let’s hear it.

Eric Ressler And I’m going to say that at the end of the day, if I had to choose one word to summarize everything, it would be conviction. Conviction. Conviction.

Jonathan Hicken Okay. Let’s hear it. Unpack that for me.

Eric Ressler So the reason why I go there is because I think what I’ve noticed when I work with orgs who are deeply strategic and actually live that strategy, right? It’s not just sitting on a deck. It’s not a 200 page doc that’s collecting dust. It’s not this thing that everyone does for six months and then gets back to their real work, but where it’s like really truly embodied within the organization, there is a very strong conviction about who they are, but even more so who they are not. And so to me, strategy is like mostly about what are you saying no to versus like, what are you saying yes to? And to me, that means you have to have conviction because it’s one thing to have an idea about what your strategy is. It is an entirely different thing to actually live that idea and make those hard choices and say those nos when it’s really hard to do that.

Jonathan Hicken Okay. Counterpoint.

Eric Ressler Okay.

Jonathan Hicken You say conviction.

Eric Ressler Yeah.

Jonathan Hicken And where my mind goes is to like the classic tale of the charismatic leader, the person that speaks the loudest and speaks it well and is convicted about what they believe. But I don’t think you’re describing that right now.

Eric Ressler Right? Maybe. Maybe a little bit because I think what makes those leaders charismatic and what allows them to have conviction is they’re actually very deeply strategic. Not always, but often. And sometimes that strategy can be masked or overshadowed by their charisma or by their personality or by their network or all these things. But I think you get there by actually having a lot of clarity around who you are, who you are not, and where you are going, which to me, that is strategy more so than the how you’re going to do it, which is tactics, not strategy, or the plan, which often is used to mask a lack of conviction and boldness. It’s like, “Well, we need to raise 10 more million dollars, so we’re going to invest 20% more in our development team and et cetera.” Yes, all those things matter. Of course, these things need to be broken down, but only if there is a strong conviction underpinning all of it.

Jonathan Hicken If let’s say you have that conviction — by the way, I like this. I like this, partly because I relate to it and I want to convince myself that I’m strategic for this reason.

Eric Ressler Yeah, but let’s poke holes in it.

Jonathan Hicken Please. Yeah. I want to pressure test it because I want to be clear. You’re saying that there’s a hard separation between strategy and tactical execution.

Eric Ressler Yes.

Jonathan Hicken And so you can have a strategy that’s absent a sort of a tactical plan to get there.

Eric Ressler Yes.

Jonathan Hicken Okay. You think those things can exist separately?

Eric Ressler I think they should exist separately. I think they are connected and interrelated, but different. And I think they get very commonly conflated in our space.

Jonathan Hicken I agree with that. I’ve been in a number of boardrooms on a number of strategic plans and the impulse I find for most people is to go tactical. What are we going to do and how are we going to do it? And to call it strategy. So we’ll get to that, picking that apart for a second.

Eric Ressler Yeah.

Jonathan Hicken When you think about strategic thinking, strategic development, you are doing this totally absent of how are we actually turning that into work?

Eric Ressler Not totally absent. It’s a prerequisite. That’s the difference. That’s the distinction for me is like, if you don’t have that clarity and that conviction and that confidence in it and the willingness to actually embody that, not just talk about it, but actually do it, then basically nothing else matters. Everything else is like, it’s like trying to build a house without understanding what you’re even building and you might have a bunch of plans for like, “Well, this is how the drywall is going to go up and the framing and here’s the tiles we’re using.” But no one even knows why they’re building it or what they’re not building. That’s kind of a metaphor you might use to think about it and then people call that strategy.

And so I see this show up in a few different flavors and I think what often happens is there’s this kind of mission creep and mission drift that can happen where there might even be a really strong strategy or conviction or theory of change or use your buzzword to describe essentially like, “This is who we are and this is how we do our work and here’s why it matters.” And we should maybe unpack what some of these ingredients are a little bit later, but that can kind of start to happen and then things change, right? Leadership changes, new opportunities come into being or a new grant will come in and then all of a sudden like, oh, we spin up this program over here and all of a sudden there’s like not really a coherent strategy anymore or a coherent conviction. And actually, I want to talk a little bit about how I’ve been thinking about this at Cosmic as part of this episode too, as just like an example.

Jonathan Hicken Yeah. Often in designing tomorrow and our conversations where you’re kind of bringing the lens of seeing lots of different organizations doing lots of different kinds of work and I’m bringing the conversation over the lens of an active executive director in the space. But I actually think this is one of those cases where you as the founder and creative director of Cosmic comes into play because I want to hear about Cosmic. How are you thinking about strategy and how does conviction come into play for you?

Eric Ressler So I think like maybe partly why I was excited to do this episode and suggested the topic, and this again came through one of our fried chicken dinners, which one day we got to start inviting the audience into one of these things.

Jonathan Hicken This last dinner was a banger by the way.

Eric Ressler That was good. We are apparently incapable of doing one that’s under three hours. I’m starting to realize as far as schedule. But I’ve actually realized that I’ve lacked conviction in our strategy at Cosmic and it’s this thing that, and maybe I feel this more than other people might, but this also started to happen in a way that’s like really funny because I see this happen with the orgs that we work with and I was blind to it for a long time, sort of like frog in boiling water kind of situation. And I think what happened for me is like, I understand our sweet spot and I started to see how our sweet spot connects to all of the other equally important elements of a successful brand. And so if I had to really describe our sweet spot, the way that I would think about our work and what we’ve done for the last 15, 16 years in this space, outside of the space, we help people understand who they actually are, what sets them apart as an organization, which can be really hard to do on your own, and then how to best communicate that with confidence and conviction.

How that shows up shows up in a bunch of different ways, but that’s really what we do. The work is transformative, the work is sometimes highly emotional. It can almost feel like therapy at times to really dig deep to get past that surface level like, “Oh, well, we’re this kind of org in this space.”

Jonathan Hicken And I can vouch for that because I’ve been on the client side twice now, and so I can vouch for that. That does happen.

Eric Ressler So to me, however that shows up, if it’s a rebrand or a website overhaul or an impact report or a campaign, that’s our approach to the work. That’s our sweet spot. But what I noticed over the years is doing that work is transformative, but it is not comprehensive. Getting that clarity is foundational, but there’s all the other parts that matter as well.

Jonathan Hicken You’re talking about fundraising, you’re talking about team development, you’re talking about whatever, all that stuff.

Eric Ressler Yeah. Even more like direct response marketing, which is also really important, but not our sweet spot. And I found myself being tempted by these different pathways of like, “Oh, and what if we did that too?” And clearly our clients need help with this and we should help with that too. It’s a common agency trap of scaling services. And it’s kind of a similar thing that can happen nonprofits with grants or whatever it is. This sounds familiar. So it’s like, I’m aware of this and yet it happened to me too. And so what I realized is that I started to lack conviction about what our sweet spot was and to own that and to say no to the things that were like, “Yeah, that’s in our wheelhouse. It’s on the outskirts, but sure, we could start there.” And my brand strategy right now at Cosmic and where we’re going is to just double down on that sweet spot for a couple reasons.

One, I believe strongly it’s important and I’ve seen the benefit of that work to be truly transformational internally, externally for our clients and people need it and people want it. And there’s a bunch of different ways for me to grow the business to expand. And I don’t even mean grow in terms of headcount or revenue, but just to do this work more fully and more meaningfully over time. And yet I think actually the best thing that I can do for our brand is to just really, truly understand that’s our sweet spot and get better and better and better and better at it and just like own that. For the social impact space, there’s other things I could do in terms of like, should we double down on a particular focus area or category? But I’ve pretty intentionally decided not to do that. But it’s this weird reflection that I came back to that’s like, that is us and that’s enough.

That’s enough.

Jonathan Hicken So what the fuck is even strategy? I think what I’m hearing from you is it’s conviction, but I heard a couple of pieces, so I just want to make sure I’m hearing this correctly. One, there’s almost a self-awareness piece.

Eric Ressler Huge self-awareness piece.

Jonathan Hicken A self-awareness piece. And for a while there, it sounded like you started to lose a bit of that sort of clarity in your own self-awareness.

Eric Ressler Kind of like organizational self-awareness, but also personal self-awareness.

Jonathan Hicken I’m sure. Yeah. I’m sure on the leadership side too. But like Cosmic, you were like, for a moment there, you were losing sight of, or actually kind of losing grasp on the self-awareness.

Eric Ressler I think losing grasp and confidence.

Jonathan Hicken Yeah, and confidence, sure.

Eric Ressler But keep going because I want to come back to that thread.

Jonathan Hicken Okay. So that’s one thing I’m hearing you say. I’m hearing you also say like a brutal ability to say no, and to saying no to the things that you’re not informed by that self-awareness.

Eric Ressler Yes.

Jonathan Hicken And actually I love that. I just want a quick tangent because I think actually I think about photography a lot when it comes to this element of strategy of seeing what you are and seeing what’s not. Because I took this photography class at college once and the professor described photography as an extractive art rather than an additive one. And that has stuck with me for decades. And I often think about when I’m saying no to things, the picture that comes to mind for me is I’m taking a photograph and I’m excluding everything except the only thing I want to see. Anyway, so I think like there’s that like — and you’re a photographer actually, so this is part of your natural skillset. Part of what you’re just saying is you’re extracting all the stuff that’s not necessary and you’re only putting in frame the things that are in alignment with your self-awareness and that conviction.

Eric Ressler Yeah, I think that’s right. Now here’s what makes that really hard. The near enemy of that is like having that conviction and having that work in a moment in time and then never evolving, right? Like this is our spot, this is who we are, this is what we do. Meanwhile, the conditions change, the environment change, the sector changes, the needs change, the problem changes, and you stay stubborn in that. That’s the near enemy of that conviction. And so it’s tough because you have to know when to evolve and when to iterate, and you have to know when to be true to who you are at your core and what sets you apart.

Jonathan Hicken I mean, those things aren’t necessarily mutually exclusive though, right?

Eric Ressler Definitely not.

Jonathan Hicken Yeah. I mean, you could be convicted about Cosmic’s role. The industry may change and how we communicate may change, but transformations for social impact organizations, that’s not really going anywhere. I don’t think that’s going anywhere anytime soon.

Eric Ressler Right. So this comes down to like, how do you frame that conviction? How do you think about it? If I put myself in the bucket of defined by our deliverables or our tactics, then you see some agencies that like we’re a HubSpot agency or something. That’s a dangerous conviction to have because you’re attaching yourself to another brand or a particular platform that you can’t control. You see these startups who build on, back in the day would build on Twitter and then Twitter would change their API and they’re basically extinct overnight. So they are not mutually exclusive, but I want to acknowledge that it is difficult. It is difficult to both have that conviction and clarity around like, “This is who I am,” being really bold and protecting that, knowing where those boundaries should be, setting those boundaries, consistently holding them in a constructive way for your team, and saying no to a lot of things that are enticing, exciting, even aligned in some ways, but not perfectly aligned.

And I’ve heard this said in a different way, which is like, and it gets into this kind of self-help oversimplification sometimes for me, but it might be a helpful heuristic at some level, which is like either hell yes or no. It’s just like everything either needs to be hell yes or no. To me, that’s a little overly simple, but it is closer to the truth than not.

Jonathan Hicken When I imagine this decision making, I’m just thinking about my own, the way I think about strategy here, I’m constantly cross-referencing with how it’s actually going to play out. And so I want to unpack this a little bit because, just to be clear, when I use the word strategy, it’s everything we’ve been talking about, right? Or actually we’re trying to figure that out. But tactical one, that’s a little bit clearer to me like what a tactic is. And the tactic is like, what’s the actual work? What are we actually going to do? It’s the how. So I do think about the how even when I’m thinking about strategy and to me, these things aren’t clearly uncoupled. And so for example, I love this book, it’s called Good to Great, and it’s one of my favorite business books. And one of the things that they talk about is first the who, then the what. And so I think fundamentally, one of the things that I go to constantly is who is on my team, where are our skills, where are our strengths and weaknesses?

Are there other skills I need to bring onto the team in order to accomplish said strategy? And if I set a strategy that’s misaligned with the people that I’m working with, then that strategy is for not. So how does that fit into the conviction mentality?

Eric Ressler Well, I think that is partly where this gets tough because there are going to be times potentially where the strategy needs to change and you don’t have the right people in the right seats to help move that change forward. There are other times, I think, and this is probably more close to where I came from, where that’s just the wrong strategy because you don’t have the team to support that strategy. And maybe that’s a sign you’re getting out of bounds a little bit, right? Is this our core strength as an organization? Do we have the talent, the expertise, the experience, just the right alignment around that approach? And so I think there’s the who, that’s a very important part of this. I wouldn’t want listeners to think that, oh, I don’t have the team, so that’s the wrong strategy, because I don’t think that’s always true.

Sometimes I think you have to be open to like, there’s this new strategy that is right for the moment, that there’s a need that no one is filling, that we are, even though we’re not currently able to fill that need, we are best suited to fill that need out of anyone else that we’re aware of in the space. But that’s going to require training, that’s going to require growth, that’s going to require recruiting. That happens all the time and should happen. But I don’t think that you should build a strategy that you can’t logically figure out how to support with the right people, with the right tactics.

Jonathan Hicken Yeah. All right, fair enough. So the conviction comes from either, do I have the right team or can I build the right team? I mean, that has to be a question in the development of a strategy, doesn’t it?

Eric Ressler I think so for sure. And I think, again, my point with this is that I don’t think there’s a deficit of that kind of thinking as much in our space as there is of the deeper strategy work. I see a lot of strategic plans that outline who to hire, which programs to invest more and which programs to invest less than, but they are not underpinned by a coherent strategy or some kind of conviction about really who they are. Sometimes also I’ll just say this gets masked or conflated with, “Well, we have our vision statement and we have our mission statement.” And if those are done excellently, they can serve as a strategic anchor or a north star for the organization. That doesn’t happen very often, just straight up. How many people do we work with that are constantly regurgitating their vision to us? Very few.

And those get done in these retreats and then they get put on the website and then they get frankly largely forgotten. And so this goes deeper than messaging, it goes deeper than language. And it often comes frankly from like, how did the organization start? What was that spark? What was the core DNA? So for example, just to bring my own DNA back into this, if I had to choose one word to describe who I am, it would be designer. I’m a designer, I’m a creative person, I’m a musician, et cetera, et cetera. But professionally, design is my mental model of the world and I see everything through that model. So no matter what we do, no matter how we describe ourselves, no matter how we position ourselves, if it’s not designed forward, it is not going to be aligned with that conviction that I need to have to be able to say yes to certain things and no to others.

And I have a pretty broad view of what design is, so that works for me. But that’s where I would often look is like, what is that kind of core spark, that initial seed that everything grew from as part of the DNA of the organization?

Jonathan Hicken Yeah. And I mean, I relate to this. I think about my conviction that public spaces can be powerful catalysts for social change, like physical spaces. And that conviction drives Seymour Center strategy of becoming this hub for local resilience. And so I believe in the power of public spaces, and that is fundamental to how we’re building our business here. And I’ll sing that from the rooftops. So I think in that regard, I certainly relate and I see the power of that, even conversations with my own team and with donors and other stakeholders here of, if I show up with conviction, it’s almost like the self-fulfilling prophecy where they can become, actually the strategy can emerge.

Eric Ressler I think why I landed on the word conviction is because by definition, in order to have conviction in any meaningful way, it requires that you have some kind of strong belief as an organization and/or as a leader. And if you don’t have that strong belief, you kind of by definition can’t have conviction or confidence in that approach. And I think that that is, to me, if I really had to boil down strategy out of all these different — and again, hey, there’s frameworks for things. I’m not poo-pooing all those frameworks. You should never have a theory of change or whatever. That’s not the takeaway. The takeaway here is none of that matters if you don’t have some kind of deeper, strategic underpinning, some kind of belief that drives this work that you can have conviction in. And that also means that you act accordingly, right?

You have that conviction and sort of by definition, you can’t have conviction if you don’t act on it. That’s just an idea. Conviction to me is an active word. It’s a verb, right? It is something you do. It is not something you think.

Jonathan Hicken I do want to poo-poo some of the strategic processes.

Eric Ressler Let’s go there, man.

Jonathan Hicken Because even — I was at lunch today, literally, with a few other executive directors of nonprofits, and multiple people said that they had done this six month strategic planning thing, and it had ended in a fizzle, and they had just spent months on this thing, and really not a lot came out of it. And where my mind goes is, were those strategic planning consultants pressing these individuals to define what they’re convicted about?

Eric Ressler Probably not. So I mean, look, I’m going to hop on the strategic planning negative bandwagon here for a second. So we have received hundreds of strategic plans at this point. I’m going to make a couple claims. A, the longer your strategic plan is, the more useless it is. B, 90% of strategic plans don’t actually matter and don’t actually get used by organizations. Now, is there value in going through a strategic planning process? Of course there is. Going through some kind of retreat to do that, working with a consultant to do that. Of course. I think so. Yeah.

Jonathan Hicken Even just a minute ago, we talked about the value of having a third party perspective to help you see who you really are, right? So yes, there is value.

Eric Ressler I think the other thing about strategic plans is that, and this comes back to the word conviction for me, it’s one thing to have a plan and to put it in a deck and to try to embody that into an organization. It’s another thing to actually do that plan. And this kind of comes back to some of the ideas around design thinking even around testing assumptions early in the market, getting early prototypes and validation of those ideas early because plans are just plans at the end of the day, right? And they do not — they’re by definition imperfect. And I’m not saying you shouldn’t have a plan and everything should just be done with vibes or shooting from the hip where I know we’re in a vibes economy right now, but I don’t think that’s a responsible way to steward donor dollars in the world.

And at the same time, I’ve seen so many strategic plans and strategic planning processes skip that deeper work and they feel a little bit tactical most of the time. It’s all about the how. And maybe it’s just it’s hard to transfuse that deeper experience that maybe the org went through that we weren’t part of. But I honestly think that it would be a lot better to really just rapidly get to the core of this as quickly as you can, just enough strategy and then test it. Test it in the real world as soon as you can.

Jonathan Hicken Yeah. Go listen to the minimum viable strategy approach episode we did a little while ago. I mean, we break it down a little bit more like how to actually do it in that episode. I’m hearing some advice in here for future executive directors or social impact leaders, right? Which is almost like if you are in the process of choosing whether or not you’re going to join said organization or not, I think what I’m hearing you say is you got to ask yourself, are you really convicted about this? Is there some deeply seated belief you have that fits into the work of the organization you’re considering joining? And if you don’t feel that conviction, should you really do it?

Eric Ressler I think that’s a great test. Yeah. And I think that there’s a lot of feelings in this space around — and for good reason, I believe in this work, I believe in the cause, I believe in the mission, and I think that that is important, but it is not enough.

Jonathan Hicken It’s not enough. I totally agree.

Eric Ressler It’s not enough, not because it’s not good enough, but because that is not a strategy, right? Passion is not a strategy. It’s an important element, but you need to have that conviction that not only do I believe in the mission, but I have a deeply held belief that this is how it should be done. This is the way we’re going to do it. This is what is a yes and what is a no. At the end of the day, you could take any framework in the world, you could take any approach to this in the world, and if you don’t know what to say yes and no to, you don’t have a strategy.

Jonathan Hicken I’m thinking about homelessness as an example here, right? Like you may be thinking, yeah, homelessness is something I care deeply about and I think it’s really important for us to solve, but do you believe deeply in say the housing first strategy to solving this problem? Do you believe that deeply at your core or do you just sort of generally believe that homelessness is something that we should be working on?

Eric Ressler Yeah. I mean, I think that’s a good test that you could do for any niche, for any kind of focus area. So hopefully this is a good way. We didn’t get into all the details around different frameworks of strategy, but I just hear this word being thrown around to the point where it’s basically ubiquitous and there’s no definition around it. So I think it was good to just kind of unpack what does it mean to be a strategic thinker in this space? And this is my version of it. Other people can come up with their own, but it’s the closest that I got.

Jonathan Hicken Well, hey, honestly, like you’re saying, and I’m like, gosh, that works for me. That works for me in my position as an executive director. I’d actually be really curious to hear if other listeners think this fits.

Eric Ressler Yeah. So listeners can email us at podcast@designbycosmic.com. We get those, we read them, so please do. And Jonathan, yeah, thanks for riffing with me on this one today.

Jonathan Hicken All right. What the fuck is even strategy? I think we got there.

Eric Ressler We got a little closer at least. All right. Thanks, Eric. All right. 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 number that keeps coming up in conversations about American philanthropy right now. $1.5 trillion. That’s what’s currently held in U.S. foundations alone. Add in donor-advised funds and the total climbs past $1.7 trillion.

Now, some of that money is moving. But most of it is on the sidelines. It’s growing, it’s compounding, it’s waiting. And meanwhile, federal funding for nonprofits has been slashed. Communities are scrambling. Organizations on the front lines of housing, health, democracy, and climate are being told to do more with less while the sector that exists to support them guards its endowments behind a rule that was never meant to be a ceiling.

That rule is the 5% minimum payout rate. When Congress first required foundations to distribute a share of their assets back in 1969, it was meant to be a floor. More than fifty years later, most of the sector treats it as a maximum. The question is: what happens if we raise it?

To explore that, I talked with three leaders behind the Level Up campaign, a coalition effort organized by CHANGE Philanthropy that’s asking foundations to increase their payout to at least 8% for two years and to prove it with their tax filings.

Aaron Dorfman is the President and CEO of the National Committee for Responsive Philanthropy, the sector’s independent watchdog. Jodeen Olguín-Tayler is the Campaign Director leading Level Up at CHANGE Philanthropy. And Amanda Andere is Co-President of Neighborhood Funders Group, bringing a decade of experience organizing funders around housing justice.

I’m Eric Ressler, and this is Designing Tomorrow.

Episode Highlights

[00:00] The $1.5 trillion sitting in American foundations — and why most of it isn’t moving

[02:03] Why 5% isn’t enough for the urgency of this moment

[03:23] Challenging the perpetuity argument — and one leader’s decision to stop saving for her son’s college fund

[06:15] How philanthropy responded to the 2025 crisis — and where it fell short compared to COVID

[10:49] Moving resources rapidly, flexibly, and with trust

[13:50] What “give better” actually looks like — unrestricted, multi-year, and directed toward power-building

[17:24] Why Minneapolis was ready — the invisible infrastructure investment that held

[21:18] Confronting criticism of progressive philanthropy in a polarized moment

[25:39] The billion-dollar imbalance — how right-wing donors outspent progressive philanthropy

[29:24] Why Level Up requires proof, not just promises — the accountability pillar

[35:03] How peer pressure is moving reluctant foundations forward

[39:53] The donor-advised fund question — and what DAF holders can do right now

[44:03] MacKenzie Scott, Chuck Feeney, the California Endowment, and foundations already leading the way

[49:28] What foundations and nonprofit leaders can do right now to get involved

Notable Quotes

Aaron Dorfman — “We can’t leave this capital on the sidelines.” [02:30]

Jodeen Olguín-Tayler — “I stopped putting funding into my son’s college education fund because if we don’t have a world that is effectively addressing climate, racialized violence, building power for communities to actually make decisions, I’m not sure my eight year old is going to have the need for a college account.” [04:34]

Amanda Andere — “We didn’t see enough moving of resources fast enough because people were still trying to figure out where we were in the moment... We couldn’t agree what was actually happening.” [09:00]

Aaron Dorfman — “Find groups that are doing great work that you trust and give them the freedom to adapt to a changing landscape.” [15:00]

Amanda Andere — “What is the grant report or the theory of change you would’ve asked Dr. King in the civil rights movement? We laugh at that, but that is the moment that we’re in.” [15:54]

Amanda Andere — “Minneapolis has shown us that investment in infrastructure in 2020 is the reason why they’re able to respond in such a comprehensive way now.” [17:24]

Aaron Dorfman — “Right-wing donors spent a billion dollars in funding for voter suppression and other anti-democracy activities in three years leading up to the 2024 election. They got a pretty good return on their investment.” [26:00]

Aaron Dorfman — “Should anyone really be surprised that those who have a vision for a more fair, equitable, and just society can’t make progress when we aren’t willing to make the same kinds of long-term, high-dollar investments?” [26:45]

Jodeen Olguín-Tayler — “Other pledges could practically be signed by foundation communications staff because they didn’t require big changes.” [29:30]

Amanda Andere — “Whatever you thought you were doing during the civil rights movement, whatever you thought you were going to do during the Nazi occupation — that is what you should be doing now.” [51:15]

Aaron Dorfman — “If you’ve been broadly invested in the markets, you can afford to go to 8%, 9%, 10% payout rate for the next few years and still have immense purchasing power in your corpus.” [53:15]

Resources & Links

• Level Up Campaign — CHANGE Philanthropy

• National Committee for Responsive Philanthropy (NCRP)

• Neighborhood Funders Group (NFG)

• Amalgamated Foundation

• Movement Voter Project — Report on long-term philanthropic infrastructure investment in Minnesota

• Climate and Clean Energy Fund — Report on multi-decade philanthropic investment in Minnesota

This interview has been lightly edited for clarity and readability.

Full Transcript

Eric Ressler: Thank you so much for joining me today. Really excited to dig into our conversation about all things philanthropy, but especially the Level Up campaign that you all are behind. To start with, Aaron, I’d like to ask you a big component of this campaign is 5% is not enough when it comes to spend down percentage requirements for philanthropies. Simple question, why isn’t 5% enough?

Aaron Dorfman: If you look at what’s going on in our world right now and the immense threats facing communities in this country and the cutting of government funding, philanthropy can and shouldn’t be expected to fill all of those gaps, but 5% is not enough to match the urgency of this moment. We need more from donors and foundations who have the means to really bolster a strong civic response to this moment. They got to get in the game. We can’t leave this capital on the sidelines.

Eric Ressler: So one thing that I hear as kind of a counter argument to this is that the nature and the benefit of the 5% spend down is that it provides this perpetuity, this sustainability for these funders that by continuing to invest their assets and only spend down 5%, their overall assets are growing year over year as they invest them. And that makes sure that especially philanthropies that are doing, let’s say, climate action work or work that might take decades to solve, they ensure that they become a sustainable source of funding for those organizations. Jodeen, I want to go to you. What do you say to that counter argument?

Jodeen Olguín-Tayler: I would say that it is time that we have a new normal in philanthropy and the Level Up campaign is actually designed to set a new floor and not a new ceiling for the payout rates. I actually work at a philanthropic fund where we took a vote to become part of the Level Up pledge as part of a conversation about our commitment in the long term to setting a spend down timeline. And that’s because we know that the giving that we’ll be able to do, especially if we come to meet the payout rate of the Level Up pledge at this really timely moment for communities and in our country, we will inspire other philanthropic giving to come in over time. There is no shortage of resources in the philanthropic sector and this economy is producing billionaires and so there will be new philanthropists that can come in and step in when one institution doesn’t exist into perpetuity.

As a parent, I would also say I stopped putting funding into my son’s college education fund because if we don’t have a world and a sector that is effectively addressing climate, racialized violence, building power for communities to actually make decisions, I’m not sure that my eight year old’s going to have the need for a college account. So this idea that we need to be looking at perpetuity instead of the immense urgent needs of communities facing violence, facing climate catastrophes, who if they were empowered to actually be governing in local states and communities, we would be making better decisions that would change the work that needs to be supported by the philanthropic sector in the long term.

Aaron Dorfman: Yeah, let me jump in here. The pledge asks you to spend more for two years. This is not like you got to spend out all your assets. That’s not what we’re asking people to do necessarily. We are indeed hoping for a new normal in the sector that is above the historic 5%, but signing the pledge means you’re committing to spending more for the next two years. It’s not a heavy lift in response to what communities are experiencing right now. I mean, if we all see what’s been happening in my home state of Minnesota where I grew up and the attacks on immigrants and everyone there, it’s like spending a little bit more for two years is not a heavy lift. Anybody can do it.

Eric Ressler: On that point, we’re recording this at the beginning of 2026. 2025 was a bumpy year to say the least for the philanthropic sector, for the social impact sector, for communities around the world, especially here in America. And my sense on this is that it feels like there was not a sufficient response from the philanthropic sector even in the same way that we at least saw lip service if nothing else being paid during the pandemic where there was this global crisis and funders seemed to recognize that, seemed to voice support, and some of them took some pretty big actions to actually spend down some more money to meet the needs of the community. And it doesn’t feel like from my purview and from discussions I’ve had with other funders and with the clients that I work with every day who are on the front lines oftentimes of this work that there’s been an equal level, even close to an equal level of response to that. Amanda, I want to go to you for this one. What are you seeing out in the communities right now and how are you feeling like philanthropy has responded to the current moment?

Amanda Andere: Thank you, Eric. I think I’ve seen a little bit of both. We’ve seen major sweeping investments in legal defense that has stopped a lot of bad actions and been able to get a lot of wins in the courts. We’ve seen some immediate infusion in traditional advocacy, some organizing, some activism. And definitely as cities were overtaken, like occupied, like in DC, in LA, and now Minneapolis, we’ve seen more local funders support things like mutual aid and bolster up the infrastructure that was already there in response to the racial awakening and uprising and COVID.

But I think to your earlier point about perpetuity, what we also saw was a lot of scrambling that happened last year because funders were trying to figure out what was the right level of resourcing for the moment. And a part of it I think that slowed things down is that as much as at the beginning of COVID there was a little bit of unknown — where did it come from? How is it going to be transmitted? How do we protect ourselves? Is a cloth mask enough? — there were things in place that taught us about the science of disease.

I think when you’re talking about authoritarian rule, when you’re talking about oppressive regimes, everyone has a hot take. People have different analysis. And in general, what we saw from philanthropy was unfortunately a lot of not listening to the folks who’ve been sounding the alarm for decades, particularly Black queer activists in the South who’ve been under authoritarian rule locally or in their state for a long time and had a lot of lessons over the years to share. So we did see a scrambling and we didn’t see enough moving of resources fast enough because people were still trying to figure out where we were in the moment. As organizers say, what time is it on the clock for justice or liberation? And folks were still trying to figure that out as it was being destroyed. There wasn’t a lot of agreement about what was actually happening. Even saying authoritarianism was something that people debated. Are we here yet? Is our democracy destroyed yet? And so I think there wasn’t a lot of coalescing around what to do. We couldn’t agree what was actually happening.

Eric Ressler: I see this tension from the funder side, and I feel it from the practitioner side as well, where there’s this balance between wanting to get money out the door to fund the causes and the missions that need resources to activate and to mobilize, but also wanting to make sure that’s being done responsibly. And I think sometimes funders are looking for inputs and research and data and proof that this work is going to be effective, that these dollars are dollars well spent. But especially in times of crisis where we need to be more quick to mobilize and a little bit more open to getting money out the door, even if maybe it’s not going to be quite as effective at times, there’s a kind of calculated risk that needs to happen. And my sense is that philanthropy in general is pretty risk averse, especially when it comes to stewarding those dollars out into the community. So what do you see out there and what’s your opinion on how we should all be thinking about that right now?

Jodeen Olguín-Tayler: I appreciate the question, Eric, and I think it relates to the third pillar of the pledge, which is to move the resources rapidly, flexibly, and nimbly. So at a time when we know that there are such immense needs for resources, we want to get the money into the hands of the organizations who are actually best positioned to make decisions about how the resource should be used and along what timeline. And so moving these resources aligned with the Level Up pledge in a way that puts those sorts of decisions into the hands of grantees is actually part of shifting the norms and culture of philanthropy that we want to see. We also support long-term, multi-year sustained giving so that when we have these inflection points and crisis points where there is an influx of resources that are needed, they can be deployed more flexibly and organizations know that they will have other sustained funding coming in over time so that they’re really able to make strategic decisions.

The other thing that I would just add — I agree, there is this tendency in philanthropy to sort of twiddle thumbs or wait for information or want what are the newest KPIs. And I think to be honest, as someone who’s also been both in a grantmaking role and in a grant-seeking role, when you build relationships of mutual trust where you’re actually talking with field leaders about what the needs are, then you as a grantmaker can learn in real time with them as lessons are emerging because they trust you to share the questions that are coming up as well as the things that they’re learning instead of waiting two years to the end of the grant report to tell you anything because there’s this fear that if you say something where there’s not a complete conclusion, that could impact your funding. So actually being willing to trust, let go of some of the power that you hold as a grantmaker and actually trust in the leadership of folks who are leading in frontline communities — I actually think will result in philanthropic institutions getting better information because they’ll be in more of a learning position to learn alongside the work that’s happening.

Eric Ressler: So we’re jumping ahead a little bit, but that’s fine. Let’s stay on this thread. One of the other pillars is give better. How can we be distributing these assets in a more responsible, trust-based way? So Aaron, I’d like to go to you for this one. How do you characterize give better as part of this pledge? What does giving better look like for funders?

Aaron Dorfman: Philanthropy has historically underinvested in organizations led by people of color, in organizations doing grassroots organizing and movement building work. All of those organizations are really needed right now. So part of giving better is who are you investing in to get us out of this mess that we’re in as a society right now, and we need to see dollars going to those frontline, grassroots, accountable organizations. That’s part of it.

The other part is give unrestricted general operating support and make it over multiple years. The evidence is overwhelming. That kind of multi-year unrestricted support is what allows organizations to be effective, to have the most impact in the world. And who doesn’t want that? What funder doesn’t want to see the groups that they’re funding have that kind of an impact? So figure it out. Lots of funders have figured out how to do it, but more need to come along and transition away from restricted project grants and towards general operating support, especially in a chaotic political and policy environment like we have right now. The outcomes and deliverables of a project grant are going to perhaps be obsolete or useless three months from now. So find groups that are doing great work that you trust and give them the freedom to adapt to a changing landscape so that they can get our society to where it needs to be.

Eric Ressler: Amanda, I want to give you a chance to weigh in on this one too.

Amanda Andere: Yeah, I appreciate what my colleague Aaron said and I would just take it a step further and also tie together some of the questions that you were asking earlier about what moment we’re in. This gets said a lot, but I think it’s really important to mention here when we’re talking about what is trust and how do you know if it’s worth the risk. We often ask people, what is the grant report or the theory of change? You would’ve asked Dr. King in the civil rights movement — and we laugh at that, but that is the moment that we’re in. And so giving better is not just finding the right organizations and trusting folks, it’s all of that, but it’s understanding that the level of investment and the types of organizations that will need to take us through this moment are also not going to be the usual suspects.

Those good organizations are probably going to know organizations that have historically been underfunded, organizations that haven’t been given the capacity to work with mainstream advocacy and policy organizations. I worked in the housing justice field before I came to Neighborhood Funders Group, and we saw this a lot during the pandemic — the people closest to the problem were the folks who didn’t necessarily have a C3, but they knew the work to prevent people from becoming unhoused. And they were often five steps away from the mainstream organizations that were receiving the money. And so that meant delays in getting critical resources out.

I think now we’re seeing both ends. We know that there’s a crisis of basic needs happening in places like Minneapolis where people actually need support to be able to live, and there’s a crisis of organizational infrastructure. Minneapolis has shown us actually that investment in infrastructure in 2020 is the reason why they’re able to respond in such a comprehensive way now. And so when we think about giving better, it’s understanding the immediate needs of folks, the infrastructure needs of mobilizing and organizing, the protection that’s needed for independent journalists, for folks on the front line, for folks who might have their safety compromised, and for the spaciousness for the long-term planning about how we get out of this mess.

And that’s part of the give better — knowing that part of the learning is giving and testing things out and that the trust is that we will never lose when part of the work is about building community and solidarity and sharing information. Those things will always be accomplished when you invest in organizing and activism. That’s exactly what happened in Minneapolis in 2020 that’s able to carry them forward right now. If they had waited to build that infrastructure, we would see very different results. Even though what’s happening is devastating, we would not see the level of care, community, and commitment. And that’s because people took risks back in 2020 to invest in organizations that knew community well, that understood how to build infrastructure, that understood how to build trust within their communities and with their neighbors. And that’s the kind of giving better that we need to see happen.

Eric Ressler: I’m glad you brought that up because I do feel like a lot of this work can be and feel invisible at times, especially when we’re talking about building mutual aid, building communities, strengthening communities. But I think when you see how the community is responding and has responded in Minneapolis and more broadly Minnesota, it’s palpable. It’s like clearly there is some kind of network here that is powering this and it’s beautiful to watch even though the situation that’s being tested is obviously tragic at the same time.

I’m holding that in one hand and then the other hand I’m holding what seems to me to be this kind of growing criticism of the so-called nonprofit industrial sector. We see this a lot on the West Coast here in California where I am around housing, which Amanda, you have a lot of experience with. And I’m sensing this kind of narrative that I think is largely politically motivated, but leading into just general concerned citizens around billions and billions of dollars being invested in these complex issues and feeling like if anything, we’re going backwards on those issues.

And to me, that might be where some of the criticism of trust-based philanthropy comes from. It’s like, well, how do we do trust-based philanthropy but also ensure that there’s accountability, especially when these are taxpayer dollars in certain situations, maybe less so now than in the past with federal funding being cut. So at the end of the day, this is really about there are these systemic issues in society. They’re not equally distributed, but anyone working in good faith can say there are problems in the world that we need to solve. So to me, the question is how do we best solve those problems effectively and sustainably, not in a whack-a-mole kind of way — sometimes you need direct relief of course, but if we’re only just providing direct relief all the time and the system perpetuates, that’s not a long-term solution either. Jodeen, I want to go to you for this one. I know it’s kind of a thorny subject, but I love to ask questions like this on this show because I think these conversations often happen behind closed doors but don’t really get the light of day. How do you think about balancing all of that and are you seeing more pushback on the philanthropic sector in general, especially in this politically polarized moment?

Jodeen Olguín-Tayler: Yeah, thanks for the nest of questions, Eric. And absolutely, I do think there is more criticism and critique and examining of progressive philanthropy in this moment. And I think more pointedly, there are undue threats and trumpeted investigations on frontline organizations that are meant to cause alarm, meant to be distracting, meant to pull people away from the urgent work that they’re doing.

I also want to go back to what Amanda was raising — the important piece about investment and infrastructure over time at the state and local level. I think there are two really good reports on the long-term, multiple decades of philanthropic investments in a set of broad, multi-issue organizations and multi-entity infrastructure in Minnesota. One was done by the Climate and Clean Energy Fund and one was done by the Movement Voter Project.

And what they both highlight are more than 15 years of different types of philanthropic institutions, donor networks investing in a broad set of organizations — not all of them nonprofits — at the local level who are really rooted in community, who are thinking about how to diversify revenue, how to bring in their own revenue, and supported their collaboration and work over the long term. And it took philanthropic investors getting out of their silos — funders who traditionally fund in climate or funders who traditionally fund in democracy or workforce development actually coming together and asking the local infrastructure: what are the kinds of resources, over what period of time, do you need to build community organizations that are working together to have governing power in the state, to actually be able to reach people at scale, to mobilize people at scale, to participate in local and state government? And I think those are two reports that really show the kind of trust, collaboration, and partnership needed between philanthropic actors and grassroots infrastructure to build the type of state-based, multi-entity infrastructure that’s needed to sustain action in these kinds of intense moments like we’re seeing now in Minnesota.

Eric Ressler: Aaron, I want to go to you for this next question. In working with a number of different nonprofit organizations and social impact organizations I’ve noticed a trend actually away from certainly federal funding in this moment — which is almost a non-starter if you’re doing anything progressive — but even major grant philanthropy in general, away from working with major foundations and more towards direct funding from high net worth individuals, major donors in the community. Almost as an exacerbation of just like this is no longer sustainable for us as an organization when funders’ priorities shift all the time, when as soon as something’s not in vogue anymore — like we saw with the backpedaling of DEI investments from a lot of major foundations and philanthropies. I think we can all agree that there are parts about this system that are not working for the greater good. Is this a time to strengthen and to kind of double down? If you were in the shoes of an executive director trying to do fundraising and build a sustainable organization, how would you think about your portfolio? And obviously it depends on the type of org that you are, but is this salvageable in your opinion? And if so, what would it look like for this ecosystem to be healthier and more sustainable long term?

Aaron Dorfman: Yeah, Eric, I think there’s a place for foundation funding. There’s a place for individual donor fundraising. As you say, it depends a little bit on what your organization is trying to do in the world, who your constituency is. So that’s tough to generalize about.

But I want to go back to something you were saying a little bit earlier, like the frustration that we’re not making more progress on some of the thorny issues affecting our society. Part of the reason for that is that right-wing donors and foundations have invested heavily for decades in thwarting progress on these issues and in strategies designed to drag our society backwards, not propel it forwards. Just to give one example: right-wing donors spent a billion dollars in funding for voter suppression and other anti-democracy activities in three years leading up to the 2024 election. They got a pretty good return on their investment for that. So should anyone really be surprised that those who have a vision for a more fair, equitable, and just society can’t make the progress we need when we aren’t willing to make the same kinds of long-term, high-dollar investments in advancing our vision for a better society? I think that’s the kind of courage that donors in the center and on the left need to have if we’re going to make progress on this. And part of that is spending more, which is why we have this Level Up pledge.

Eric Ressler: Interesting. So your point there that I’m hearing is that this is not necessarily just a failure of effective work, but there are countermeasures actively working against some of these causes that are often not considered as part of the general assessment from the public.

Aaron Dorfman: And I think we underestimate the dollars and the level of commitment coming from those who have a different vision for society.

Eric Ressler: Yeah. I mean that gets really thorny because that’s the whole subjective element of this work. When we talk about social impact work, the vision for the future looks very different depending on where you sit and what your goals are and what your vision is. And so there are, in the best faith, these kind of different ideas about what equity and what justice looks like. I think that’s not always the case, or very much not the case right now in many situations. But there’s also these efforts that are actively suppressing these issues. And you see that very clearly in the political world, even just candidate A versus candidate B. But I don’t think people typically think about the social impact space in the same way. And it’s absolutely true — if you take any hot button, especially cultural, issue, there are nonprofits working on both sides of that issue, fighting for their vision of what the future looks like, funded by very different people in this country.

I want to shift over to the part of the pledge that we haven’t talked about, the accountability part. And this I think is pretty unique for the campaign. There’s been a number of giving pledges of various shapes and sizes that are a little bit more like a public letter of intent than any kind of deep agreement or structural change that we’re asking organizations to make. Jodeen, I want to go to you for this one. Can you talk through why you built in this accountability measure, what it looks like, and how that changes the nature of what it means to sign on to this campaign?

Jodeen Olguín-Tayler: Yeah, thank you for the question, Eric. The campaign is really designed to change behavior norms, narrative, and governance policies in the philanthropic sector as a means of creating a new floor for how the philanthropic sector operates. So it’s a big ambition, and the pillar in the campaign about accountability is a large part of that.

So first of all, I want to say that institutions who’ve committed to join onto the pledge have committed to share relevant grantmaking data in a secure way. And that data is not different than the data that they would need to share with the IRS eventually, but one of the things that we’re asking pledge signers to commit to is to share that data sooner as a way to make good, to verify their commitment, and as a way to help us learn more and produce and share research about how resources in the sector are hopefully shifting and being expanded.

It’s also, I think, in practice as we’ve talked with institutions and as I’ve been part of boards who’ve made the decision to sign on to the pledge — it’s become an important part of the discussion internally in an institution to make these commitments. It helps us really affirm that this is a step that we are committed to taking as an organization. In particular, I can speak to institutions that don’t usually set their grantmaking budgets over a two-year term or set their endowment payout rates over just a one-year term. This is asking them to think more than one year in advance, both about what they’re willing to commit to and how they’re willing to verify that commitment. And we need philanthropic institutions to make more than one-year commitments at this time because that allows the groups who are responding to these unprecedented needs from and within communities to plan in a more strategic and effective way. So I would say it’s an important part of the pledge, not just in terms of what we’re asking for, but it actually becomes an important part internally for institutions to really take seriously the commitment and the strategic rationale for why it’s important to make these commitments at this time.

Eric Ressler: Aaron, my understanding is that although this campaign is relatively new, you already have close to 50 pledging organizations and we’re not talking about necessarily just small organizations. Some big names on that list too. Can you speak to how this pledge has been received in the philanthropic community at large so far?

Aaron Dorfman: Well, I’m really pleased with the reception that it’s getting so far. I think we are hearing from funders that they agree that these are urgent times, that they agree that spending more and being held accountable to that is part of the solution and maybe part of the path out of this dark place that we are in. So I am optimistic. I continue to hear that folks are wrestling with what their spending policy ought to be in the next couple of years. So that makes me hopeful. We’ve got almost 50 signatories at this point. I wish we had 500 signatories at this point, and we will get more, but I am pleased with the early adopters that we’ve seen in this effort so far.

Eric Ressler: Amanda, I want to give you a chance to weigh in on this. What have you seen from your purview? My fear here — and I still think this is all a very good idea overall — but aren’t we also kind of asking the organizations who are more likely to get to this conclusion on their own? There’s a whole cohort of organizations that are going to be resistant to this. So at some level, is there a more systemic play here longer term where this becomes more of a legal requirement versus an opt-in that we should be thinking about?

Amanda Andere: Yeah, that’s a great question. I think the moment that we’re in now, what I’m seeing as I serve on the board of a family foundation and work with a lot of funders — yes, coming to this pledge was easy for them. They were already starting to have that conversation, or it offered them cover. But what we’re hearing from a lot of foundations who haven’t been on this journey is that they’re learning from their peers, and the peer pressure from other boards is influencing folks in a good way. Peer pressure can be a good thing, and it’s not just the pressure of it, but it’s the “how did you bring this conversation to your board? What are the things that you thought about that allowed them to think about this in a long-term and a short-term strategy?”

So in essence, this has created its own cohort of people who are starting to talk to each other, maybe in more underground ways, maybe in more overt ways, to get us to the 500 that Aaron wants — that we all want — if not all foundations who care about people and democracy and having a country that is able for all people to thrive and survive. We have to have a different conversation. And I think the Level Up campaign is allowing people to have that conversation in a context that might feel a little bit safer to them. And I think none of us in the CHANGE Philanthropy coalition want to just have safe conversations. We want to have bold conversations. But we want to have the right conversations that actually get people to move in ways that are transformative and not in this inattention and attention cycle, not in these short spurts. And so that’s what I think we’re planting the seeds and building the foundation for — these longer-term conversations.

Eric Ressler: I really like the concept of giving foundations the cover, the permission almost to do this, even the social cover. Because I do feel like a lot of the reluctance might be a PR backlash or social pressure or sometimes even accountability being something that they’re not used to. We see a lot of funders starting to spin up as philanthropy LLCs so they can do things however they want on their own terms, especially when we’re seeing family offices transform from tech where they’re used to basically doing whatever they feel like and not having accountability. So it is an interesting space that we’re in. But Aaron, I want to give you a chance to weigh in on that last one because I sensed that you had some thoughts.

Aaron Dorfman: Well, look, Eric, there is a time to have a conversation about what the rules governing philanthropy ought to be. And now is not that time. It certainly isn’t. We have an autocrat who is attempting to dismantle our democracy, and we all need to band together and resist that and make sure that we have a thriving multiracial democracy that we come out the other side of this with something that is better than what we’ve ever had before. That’s what I’m looking for. And someday there ought to be a conversation about what the rules governing philanthropy ought to be, but there are far more important fish to fry than that right now.

Eric Ressler: I think that’s a fair characterization, and I think that we need to be pragmatic as a sector right now. We need to understand there are systems that are imperfect and we need to work within them and mobilize rapidly in this moment. And we should certainly be having conversations around the long-term shifts that should happen to the sector. But there are people suffering right now that need support and need help and need dollars. And so I think that’s a really smart way to think about it.

I want to touch on one other element that’s tangentially related to this. There’s been a lot of discussion around DAFs, or donor-advised funds, as a safe haven for tax-free dollars for the ultra wealthy. Some people argue that DAFs are a net benefit for social impact and a new vehicle that will get more money out of bank accounts and into communities where we need them. But DAFs aren’t set up in a way that requires any spend down or payout, not even a 5% minimum from my understanding. And so I’d be curious to kind of introduce DAFs into this conversation. Obviously different — we’re not talking about major philanthropy here, we’re talking about individual philanthropy — but to me it’s a related topic in that how do we get more philanthropic dollars out of the coffers of ultra wealthy and into the communities that need them? Jodeen, I want to go to you to start on this one.

Jodeen Olguín-Tayler: Yeah, thanks for that. We have had a couple of donors who operate through DAFs who have signed on to support the pledge. And I think it is, as Amanda said about creating examples — catalytic examples and leaders that can be elevated within the sector for others to follow. So we’re glad to have those examples amongst the signers.

I would also say that we have talked about ways to approach some of the philanthropic institutions that house DAFs to talk with them about the importance of this campaign. And there are organizations — I would elevate the Amalgamated Foundation, that has a practice of encouraging DAF holders at the end of every year to get their money out. And you cannot indefinitely hold resources in a DAF there and just accumulate them and not spend them.

I think one of the reasons why it’s so important that this campaign is held and housed by a network of 10 philanthropic infrastructure organizations through the CHANGE Philanthropy Coalition is because we do have relationships with so many different types of philanthropic institutions and can help to collectively approach some of the influential actors like DAF holders and have conversations with them about what they may already be doing to ensure that DAFs are not just tax havens and actually get resources out to work that is very urgently needed in communities who should be holding those resources. And so that is something we’re discussing as both a coalition and as a campaign, as something on the horizon. But I do think it is a very important issue in the sector at the moment.

Amanda Andere: Kind of like Aaron, I think the conversation around DAFs is this larger conversation that we need to have in this sector right now. What we need to be doing is getting to those folks who might hold DAFs that have been politically motivated, who largely have contributed to political campaigns, that are now seeing the need for advocacy, organizing, and activism. And actually in having conversations with some of these high net worth individual donors and folks who have long been involved in some type of political work but not in this way, they want to figure out how to move money. They’re coming to organizations like Neighborhood Funders Group, like Funders for LGBTQ Issues. And that’s why the coalition is so important, because they want to figure out who do we move money to really quickly? What’s a trusted resource? And they know that we have those relationships and partnerships, they want to start to align their dollars with foundations, with individual donors.

So I think that work is happening right now and we need to in this moment build community and not shame people, but give them pathways and on-ramps in order to now move resources and stay connected with them so they understand the impact and then they start to move more resources. And that’s what I want to focus on in this moment.

Aaron Dorfman: Well, I think Amanda and Jodeen covered it. DAFs are an important piece of the landscape. Let’s make sure that donors who use donor-advised funds move that money, get it out the door, increase their giving.

Eric Ressler: So when we’re talking about increasing this spend down percentage from 5% to 8%, even over just two years, it’s a significant increase. Some people might feel like that’s a lot, but I also know there are examples of organizations out there who have already done this, have done it more aggressively — even thinking about MacKenzie Scott spending down billions and billions of dollars much more quickly than that. I’d be curious to hear, are there already organizations that you all are aware of who are moving this way already, that inspired you, or that are allies in this kind of faster spend down vision? Aaron, I’ll start with you.

Aaron Dorfman: Yeah, I mean there are a lot of great examples. MacKenzie Scott is one. She’s one of the few Giving Pledge signatories who’s actually moving resources at a speed fast enough to meet the terms of that pledge. Most of them aren’t anywhere close to it. You think about the sort of most well-known “giving while living” proponent, Chuck Feeney, the founder of Duty Free Shops, who gave away an $8 billion fortune during his lifetime. And those grants did a tremendous amount of good. The donors who think about this think about how making a difference on issues now is a more cost-effective way than waiting to try to make a difference on those in the future.

And I’ve had lots of conversations with donors and foundations who have signed this pledge or who are thinking about signing this pledge. And most of them tell me, “Well, we were already talking about this, Aaron, before you asked us to sign the pledge. We understand the urgency of the moment. We want to do our part.” And signing the pledge is a way for us to take a stand publicly and encourage other institutional grantmakers to also step up and meet this moment. I think I’m not speaking out of school to say that the California Endowment was one of those — they’d already been having these conversations, but they gladly signed on to the pledge because it was in line with what they were already thinking. And hopefully it encourages other donors, other foundations to have the permission to make that step as well.

Eric Ressler: Jodeen, do you want to weigh in on this one?

Jodeen Olguín-Tayler: Yeah, absolutely. As Aaron said, we’ve seen a number of family offices as well as institutional funders take the step formally because of the pledge. But we’ve also been in conversation with public charities, community foundations who have signed on, intermediary funds. One of the funds — the Movement Voter Fund — signed on early to the pledge and had a conversation with their board where they said, this is a risk for us to make a commitment for two years to raise our grantmaking because we raise money to give out. But actually signing on to this pledge is taking a strong position that this is a time to be taking action in our sector and gives us an opportunity to talk with our institutional funders and across our broad donor network about the importance of making commitments over a longer period of time and making larger commitments at this time. So in those ways we see a wide range of philanthropic actors getting involved in the pledge and also using it as a tool to make bigger and more active commitments to the field.

Eric Ressler: Amanda, what are you seeing out in the space?

Amanda Andere: I’m seeing the exact same thing. I think about one of the pledge signers, the Meyer Foundation based in DC, who I asked to sign the pledge. They in relatively short time talked to their board and their staff. And what’s important about that is that DC’s funding pool is very small compared to other communities. And so that level of increase is significant. And it also has necessitated conversations with other funders in DC who now are talking about increasing their payout — and they never were having those conversations or were putting off those conversations.

Meyer was already working with their grantees around increasing in certain areas. They were already giving responsive and emergency grants. And so this just leveled them up in a way that allowed other funders to see that they could level up. And maybe that means that they won’t sign the pledge, but maybe it means that they’ll think about doing their grantmaking in more responsive ways. Maybe they will do a temporary increase, and then we know we can hold them accountable having those conversations.

So I think those are the types of things that happen when you have these kinds of pledges. As we talked about before, all investment in getting people to do things differently is good because it builds community, it gets people talking, and it builds solidarity in ways that sometimes will be measurable and sometimes will not be. And that’s why we need to keep on having these conversations with folks so we can tell the stories about the unintended consequences that actually are good unintended consequences.

Eric Ressler: So before we wrap up, I’d like to give each of you an opportunity to make your own personal case. If we have some funders listening who are hearing this and they’re motivated and they’re on board, what is it that really tips people over the edge? And what’s the first step that people can take if they’re interested in potentially signing onto the pledge, or even for nonprofit executive directors who want to share this episode with funders that they’re in relationship with? Jodeen, I’ll start with you.

Jodeen Olguín-Tayler: Yeah, thank you. I would say please reach out to us. One of the great things about how we’re built as a coalition is a network of both board members and leaders of philanthropic institutions who’ve made these commitments and who have also said, “We’re happy to go talk with your board. We’re happy to share the process that we went through to be able to make this decision or have a longer-term conversation about it.” There are a number of partners in CHANGE Philanthropy who do amazing, very detailed research about how to move money, where it’s currently being moved to, who to move it to.

And so I think we have a wealth of resources to support philanthropic leaders and executive directors who want to make this journey. We also have a community of trustees of color who are board members of philanthropic institutions who are bringing the pledge to their boards and working internally to make — not just adopt the pledge, but it really is about making this bigger shift in the norms and behavior of philanthropy over the long term.

And so I would say reach out to us. This is a moment where collective action in the philanthropic sector actually does matter. This is an opportunity and an invitation for you to take a very important step to level up, and we will help you, support you, and accompany you and be sure you have the resources and networks to support you on this journey. So let us know how we can support.

Eric Ressler: Amanda, over to you.

Amanda Andere: Well, thanks Jodeen. I think you said the right things technically and the right resources. I would just take us up a level to where we started. And while these are not unprecedented times for people at the sharpest intersection of marginalization, it now feels unprecedented for many people who’ve not had to confront the realities that our country does not work for everyone.

And so what legacy do you want to leave in this moment? Whatever you thought you were doing during the civil rights movement, whatever you thought you were going to do during the Nazi occupation — that is what you should be doing now. That does not mean just doing incremental changes. It does not mean just a little bit more. It means showing up in ways that say to community: we understand what you’re going through. We understand that we’ve been part of this problem. We understand the long-term and short-term investment it’s going to take to get out of here and build a community that works for all people. And we are right there with you with more resources, learning alongside of you, trusting you, and being accountable to what we say we’re going to do.

And I would just call on people’s moral clarity. I would call on people’s spirit of abundance. And I would ask them to think about what they would say they were going to do in moments of oppression — because that is what you should be doing now. And it needs to be reflective of what you want your grandchildren to remember you by and the legacy you want to leave.

Eric Ressler: Beautiful. Aaron, over to you.

Aaron Dorfman: Well, Amanda and Jodeen said it all quite beautifully. I would just add: if you’re a trustee of a foundation and you’re wrestling with this question — does it make a difference even if we do it, if we give more? — there are 10 philanthropy infrastructure organizations that are connected to hundreds of nonprofits, thousands of nonprofits and grassroots movement groups, and they are telling you it will make a difference. It will matter if you increase your spending rate for the next couple of years. And if you look at your returns the last few years, if you’ve been broadly invested in the markets, you can afford to go to 8%, 9%, 10% payout rate for the next few years and still have immense purchasing power in your corpus when we are hopefully on the other side of this crisis facing our society.

Eric Ressler: Aaron, Jodeen, Amanda — thank you so much for taking time with me today to break down this Level Up campaign. Thank you also for doing this good work and encouraging a more ambitious, responsible form of philanthropy and getting more money into the communities that need it most right now. Appreciate all of you for joining me today.

Aaron Dorfman: Thanks for having us, Eric. Thanks so much.

AI can now generate more content in a day than most organizations produce in a year. Every platform is converging toward video. Algorithms reward volume, but audiences crave connection. And somewhere in the middle of all that, social impact leaders are trying to figure out how to show up authentically without burning out or blending in.

In this episode, Eric and Jonathan dig into what they’re calling the great content reset — the collision of AI, shifting media formats, and a growing hunger for real human connection. They unpack where AI actually helps (and where it creates what Eric calls “AI slop”), why Derek Thompson argues that everything is becoming television, and the timeless communication truths that still hold no matter what the technology of the moment looks like.

If you’re an executive director or communications leader trying to figure out your content strategy in 2026, this one’s for you.

Episode Highlights

[00:00] The Great Content Reset

[01:03] The Google Ads Nightmare

[03:05] AI as Content Accelerant

[05:20] Quantity vs. Personality

[08:18] How We Use AI on This Show

[10:33] When AI Helps vs. Hurts

[14:16] Everything Is Television

[18:22] Should Every Org Create Content?

[20:06] The Return to In-Person

[23:13] Timeless Communication Truths

[26:41] The Value of Imperfection

Notable Quotes

Eric Ressler: “As the channels get noisier and noisier, you basically have to show up more and more — and that is really the only way to truly break through. But is that really going to be your strategy?” [00:00]

Jonathan Hicken: “I had this nightmare moment where it occurred to me — are people even planning what to do on a weekend by searching Google anymore? Are they just asking ChatGPT?” [01:03]

Eric Ressler: “If you are using AI to just pump out more and more content, and you’re not at least heavily editing that content so that it feels like you, there’s a weird kind of uncanny valley thing happening.” [00:27]

Eric Ressler: “I think the idea of ‘we do good work behind the scenes’ — there is less and less viability in that model.” [18:22]

Jonathan Hicken: “If every listener went out and created a podcast for their cause, what does that make the sector look like? Are we better for it?” [17:55]

Eric Ressler: “The more AI slop comes in and pollutes these channels, the more anything that feels different than that becomes important.” [26:41]

Eric Ressler: “I often think I know something until I sit down and try to write a 1,500-word piece about it and realize I don’t have it as figured out as I thought.” [19:00]

Resources & Links

• Mike Nellis — The Endless Urgency of Digital Organizing (Designing Tomorrow Spotlight)

• Amanda Litman — Run for Something (Designing Tomorrow Spotlight)

• Derek Thompson — “Everything Is Television” (Derek Thompson’s Substack)

• Why No One Cares About Your Content (And How to Fix It) (Designing Tomorrow, Season 1)

P.S. — Struggling to figure out your content strategy in a world of AI and noise? Cosmic helps social impact leaders build trust through story-rich brands, compelling campaigns, and values-aligned strategy. Let’s talk about how to show up with clarity:

https://designbycosmic.com/

Full Transcript

This conversation has been edited and condensed for clarity.

Jonathan Hicken: Eric, over the last several months, I’ve been asking my team to put a lot more time and energy into Google Ads, and we’re seeing some results, don’t get me wrong. But over the winter break, I just had this nightmare moment where it occurred to me — are people even planning what to do on a weekend by searching Google anymore? Are they just asking ChatGPT to plan their weekend for them? If so, how do I get my results higher on ChatGPT? What does it look like to get into those results? My mind started spinning about how so many things are changing about content and algorithms and everything, and it made me feel like we are going through a great content reset.

Eric Ressler: Yeah, that certainly feels like where we’re at right now.

Jonathan Hicken: So I want to spend today unpacking some of these major changes that you’re seeing, particularly on the Cosmic side of things, the organizations you’re working with, and how we as brands could be preparing for this great content reset.

Eric Ressler: Yeah, let’s riff on it. I feel like we are in the middle of this very fluid media internet transition right now, and I don’t know where it shakes out. AI is definitely a major lever in that, but it’s not the only lever either. Where do you want to start?

Jonathan Hicken: Let’s start with AI itself. Not all AI, but let’s start there because we’re all using it. We use it at Seymour Center. We use it in Designing Tomorrow. But for social impact leaders who are trying to think about how they’re building a brand and putting themselves forward at a time where we’ve been hearing about how authenticity matters and individuals matter — what is the advice that you are giving to clients? How should I be preparing for this great content reset?

Eric Ressler: So to me, AI is kind of like an acceleration of an existing trend of lower and lower barriers to content production. Often these trends are driven by technological innovation. The common example is the printing press creating this democratization of information at a level where books no longer need to be hand scribed one letter at a time. Then you fast forward and you get to TV and radio and the internet and all these different modalities. I’ve even noticed this in production — making a brand video used to be a $250,000 investment. You needed a whole TV crew. And sometimes those videos still need to be made that way, but also everyone can just shoot themselves in a selfie iPhone video and post it on TikTok and get more views than those brand videos are getting right now.

So media is always changing, technology is always changing. Media and technology are two sides of the same coin. To me, AI is part of that. Now the ability to pump out large volumes of content essentially effortlessly is more possible than ever before. But the quality of that content and the resonance of that content is definitely not guaranteed.

I think what’s different about AI is that it’s not just a technology used by humans. It’s becoming more and more a technology that acts on its own as we start to get into agentic AI and discussions of AI replacing the workforce and the potential bubble around all of that. My general takeaway is AI is a transformative technology. We just don’t know what exactly it’s going to transform and how it’s going to transform culture yet.

Jonathan Hicken: I’m thinking about two interviews you did recently, one with Mike Nellis, one with Amanda Litman. The two messages that stick out to me — Mike said something like quantity is king, you’ve got to produce a lot of content to matter. But Amanda said people follow people, not brands. So what that tells me is one person has to produce a lot of content. Isn’t there just this tug towards using AI because you need to be producing a lot?

Eric Ressler: So just for listeners, you’re referencing Mike Nellis and Amanda Litman, two interviews we’ve had in our Spotlight series, which we’ll link to in the show notes. Both definitely worth digging into. If we want to point to this volume play that Mike is pointing to, which I think is real to a degree — he comes a lot from the political space but also works with social impact orgs — as the channels get noisier and noisier, you basically have to show up more and more. And that is really the only way to truly break through. I don’t think he means it’s the only way, but it’s the most sure way. Yeah, you could break through because you produce one viral video, but is that really going to be your strategy?

How many times do people come to us saying, “Hey, we need to make a viral video”? We know exactly — no, of course not. There’s a certain amount of luck and perfect alignment with the zeitgeist for viral videos to come out. I’ve had posts on LinkedIn go LinkedIn viral, which is so nerdy to say that I’m almost ashamed it just came out of my mouth. But those posts don’t move the needle as much as you think they do, and especially if there’s no follow through and consistency after the fact.

So Mike’s pointing to this consistency element, this quantity element, and Amanda’s pointing to something related but different — that the era of brands influencing people as these faceless corporations that don’t have strong human leaders at the forefront from a communication standpoint is basically over. People naturally want to follow people. People naturally connect with people. People naturally want to hear and get information from people over institutions. Good and bad things about that, but that’s kind of where things are going.

Jonathan Hicken: I totally understand that, but in my seat as executive director, if I’m combining their advice — people need to follow a person, and I also need quantity — now it’s all on me to produce a lot of content. And that is pulling me towards AI. As long as the AI sounds like me.

Eric Ressler: I see how you get there, and I don’t even think that’s necessarily the wrong assumption. Let’s just open the kimono a little bit here. Do we use AI for the show? Yes, but we use it in very intentional ways. We don’t use AI to write content for us. First of all, it’s a podcast. Our podcast format, we have a few different flavors of content at this point, but we’re just riffing on a conversation here. AI is not doing anything here.

Jonathan Hicken: In the room.

Eric Ressler: But before we prepped for this episode, we did use AI to figure out how we’re going to frame this. And that helped us hone in on what we’re going to focus on. There’s a lot to wrestle with here. I do have concerns about some of the ethics of AI as an artist, as a creative person, especially as it relates to some of the pure forms of art like music and film where these companies have essentially just trained their models on human expression and created the ability for anyone to steal and repurpose that. That still makes me feel icky at some level. And also I’m a geek and a tech nerd, and I’m enthralled by the possibilities of the very real value that AI can have even today and even more so where it’s going when used responsibly, when used in the right ways.

But what I’m noticing, and what I think everyone needs to be very aware of, is that if you are using AI to just pump out more and more content and you’re not at least heavily editing that content so that it feels like you, there’s a weird kind of uncanny valley thing happening for me. The more you use AI, the more it’s easy to spot AI. I’m not talking about em dashes here. I’m talking about cadence of sentence structure and different little tells. I saw a post the other day of a printed book that had the ChatGPT “Would you like me to reformat this?” prompt still in it. It’s just these cringe moments. Are we losing our humanity in the process, or is it becoming more intertwined with technology?

Jonathan Hicken: This is clearly very personal to you as a musician and a creative person. But how can an executive director or a marketing leader look at this great content reset and see this world of possibility in the form of AI and see the risk? How do we make decisions about how to make content or marketing or branding moves with AI right now?

Eric Ressler: I think it really depends where you’re starting from. One way to use AI that I think is helpful and constructive and doesn’t reduce the humanity of the work is as an editor or an executive producer or a riff partner. “Hey, I’m thinking about doing something like this. Ask me some questions, interview me, help me refine my thinking” — and then use that to draft a post or create a podcast outline or whatever the format is. So less as a creator and more as a sparring partner. That’s how I use it mostly.

I think it can also be really good when you’ve created a draft of something to have it not edit it as an editor, but to review it for its strengths and weaknesses and ask it to put itself in the shoes of your target audience. What questions might they still have? To me, that’s a good low-hanging-fruit way to use AI that isn’t the same as just “Hey ChatGPT, make me five LinkedIn posts about social impact marketing in 2026.”

You’re coming at it more from a like, “I need to make more stuff. It needs to be about me and human. I don’t have the capacity to do that on my own, so do I just go to AI?” I honestly think the answer is mostly no. I think AI shows up in the framing and idea generation or refining side of it, that sparring partner angle, and there’s still a need for some human level of curation in that process.

To open the kimono again — we have human editors working on our work. We have Edith, who’s awesome, shout out Edith, for editing. And she’s doing creative work in this moment. When do I cut? When do I not cut, either out of the episode or between angles? AI can do that. We’re on a system that does auto cutting, but it doesn’t do as good of a job as Edith does still right now. Is that going to be true in two years or three years? This is all very fluid. But I think the idea of “I generate content, I feed it into the AI machine and I get it out to the masses” — I don’t think that’s got longevity unless the technology continues to improve in meaningful ways.

Jonathan Hicken: I want to take us over to another conversation about the great content reset, which has to do with an article that Derek Thompson wrote recently called “Everything Is Television.”

Eric Ressler: Yeah, I think that was it.

Jonathan Hicken: Essentially his argument is that forms of media are converging into a single format and single distribution method. The perfect example is Netflix is now live streaming podcasts. If that is true, if everything is indeed becoming TV, how do social impact leaders need to think about their brand or their message or their strategy differently?

Eric Ressler: I should start by saying I don’t fully buy Derek’s argument. I believe there’s truth to that. I think the headline is maybe slightly sensational in that it implies that all other forms of media are going extinct, which I just don’t think is quite true. What I do think is true is that if you are running a social impact brand right now in 2026, you need something that is TV in your stack. You need some kind of raw, uncut, video-first content in your feeds.

For us at Cosmic, that’s what the podcast is. I don’t have other video content for Cosmic. I could do other video stuff. I could create motion graphics breakdowns on case studies or whatever. My hope and my goal, both from a marketing standpoint and in service to the sector and a way for me to think out loud through publishing, is I want to share my thinking on the sector and how this work should be done.

I’ve often thought about the question I try to answer in my work: how can and should design be applied to social impact for the greater good? That’s what I spend every day thinking about. And the podcast has been my most meaningful channel to do that. You get Eric the most through the podcast, and that’s true. Last year I also started rolling out newsletters that are a little bit different, more kind of podcast-esque, with voiceover recordings. And that’s still a little bit more me than other stuff we put out, like guides or articles.

I think the reason we’re all so attracted to this format is because it feels the most like getting to know someone in real life. It taps into our human psychology.

I think that gets taken to a further degree with short-form video platforms like TikTok, where there’s this hacking of psychology. Full disclosure, I’m not an active TikTok user, so I might be out of touch on this. But TikTok and YouTube by extension have become this kind of amalgam of different types of media, hyper-optimized for attention. On TikTok, people know intuitively whether or not they’re going to watch something after milliseconds. So it has this veneer of being very authentic, but also there’s someone behind the curtain thinking very deeply about how to optimize for hacking human psychology. It’s this weird amalgam of both things.

Jonathan Hicken: The point that Designing Tomorrow has felt for you like the most meaningful way to express your ideas — first of all, congratulations, you’re doing a great job. But it makes me think, if every listener went out and created a Designing Tomorrow or created a podcast for their cause, what does that make the sector look like? Are we better for it?

Eric Ressler: It’s a legit question. Creating is hard. It’s vulnerable. Something I’ve struggled with as I’ve been more and more public in this work. What I would say is, does everyone need to create? No, not necessarily. But if you’re going to be a social impact organization in 2026 and you’re going to try to get your brand story out there and you need support and brand awareness, then you do need to create. Because the idea of “we do good work behind the scenes” — there is less and less viability in that model.

Publishing is incredible. Making stuff is great. I have a bias — I’m a creative person. The nature of that word means I like to make things from nothing or from raw ingredients, so it comes naturally to me. But you learn so much by putting yourself out there and creating. I’ve often said I think I know something until I sit down and try to write a 1,500-word piece about it and realize I don’t have it as figured out as I thought. There’s value even in creating even if you don’t publish. But that feedback loop that happens, that conversation with your community — it’s so valuable that it’s worth doing.

Now, does the whole sector become both a broadcaster and a consumer? Yeah, I think that’s basically what’s happening.

Jonathan Hicken: Honestly, to answer my own question, yeah, I think it would be good for the sector if we all started producing stuff. Because then collectively we are bombarding the airwaves with content that is good for the collective wellbeing. So I do think that would be good for everybody, every listener, to create something similar to Designing Tomorrow.

Eric Ressler: For whatever reason, this reminds me of another thing that’s been top of mind for me. So much has gone digital since the pandemic especially, and digital’s definitely not going away. But there seems to be this very real, very visceral, and timely shift back to in-person right now — not just in a human way, but especially in a professional way. I think we are all yearning for that human connection and face-to-face conversation.

I think podcasts and this type of “everything is TV” conversation is the closest you can get to that digitally without actually doing something in person. A lot of times when you’re thinking about this great content reset, I think part of that is things moving back more into in-person. Now, are events going to be the same as they were before? No. I think we need to get creative about how we do these convenings, these conferences, in a way that’s not stuffy and rigid and where you don’t actually get what you want out of it.

Jonathan Hicken: Isn’t it interesting that so much of the workforce went remote during the pandemic, and some of us still really like that remote element of our jobs, yet we’re also craving those in-person professional experiences — but not at the workplace. Isn’t that interesting that we’re hungry for that community, but not in the traditional format that we would normally get it? I’m not sure what that means. I’m just observing this contradiction.

Eric Ressler: Yeah, I think people are naturally craving human connection. They always are. And I think we’ve been taught through the psychology hacking of our devices that when I’m scared, when I’m bored, when I’m sad, I scroll my phone to get that. And I think everyone is realizing that’s not it.

Not necessarily New Year’s resolutions, but something I’ve been very cognizant of as I’ve been trying to reset some of my own behaviors — when I’m done with work, my phone goes away. And that hasn’t been true for me for a while. I’ve been busy, I have excuses. But the shift in my consciousness and my experience spending time with my girls and my family by doing that — it’s embarrassing how much in that moment I find myself instinctively reaching for my phone when I’m bored, when I’m frustrated, when something annoying happens. The phone becomes this almost adult pacifier.

I think this is relevant because so much of content generation and brand strategy is “how do we get our message out?” And I think we all need to be thinking about that really holistically, not just about whether we’re doing Google Ads this year.

Jonathan Hicken: So look, the great content reset — we’ve got AI in front of us, we’ve got questions of in-person events, we’ve got everything becoming TV. But as I think about the history of how we communicate with each other as humans, from face-to-face to letters to radio to TV to the internet, something has to be fundamentally true about how we communicate. What are some of the fundamental truths of social impact communication that will never change no matter what the channel or technology?

Eric Ressler: We could do another episode on this one. Let’s try and hit some of the heavy hitters. To me, there has to be some kind of crystallized vision of where you’re going as an organization to be able to do this work well. If you don’t have clarity around that, you don’t know if a choice is a mistake or a distraction or aligned with your organization. The orgs I work with who are the most effective — there’s crystal clarity on where they’re going. This is who we’re becoming, this is what we’re working for, this is who we’re fighting for. And everything can be filtered through that lens, including “this is the content we make and here’s who it’s for and here’s why these channels make sense.” You have to always have that truth or everything is just a guessing game — whack-a-mole and sporadic.

There are things about negative framing or curiosity-driven framing and the hook — we’ll point back to some episodes that I did in season one where I went deep on all that stuff. I think that’s a skill. You’ve got to just start and see what works, but there are actual skills in doing this work that are worth reading up on.

But more deeply, the goal should be — and this is a long-time goal for us on this show — the more real this can be, the better. The less this is about “let’s create something polished, let’s create something professional, let’s create something based on some standard of what this should look like” — and the more real it is, I think the better it performs. That’s been true in our experience. This show feels more and more like our dinner conversations today than it did in season two, by a long shot.

I mean, you’re dropping F-bombs these days, which I’m here for. But those are some of the non-traditional things. I could give you tactics, but I really think that’s where you should start.

Jonathan Hicken: Yeah, as an executive director, I’m thinking about a shifting landscape. And if I can root myself in something that I know is going to be reliable no matter where the industry or content goes during this great content reset, then I can feel confident knowing that I’m putting out something that’s going to be effective for our mission.

Eric Ressler: To take it back to the top of the episode, I do think that the more AI slop comes in and pollutes these channels, the more anything that feels different than that becomes important. Whether that’s a conversation on film between two human beings, or something kind of oddly related — I find myself listening to more and more live recordings of music versus studio recordings as AI starts to come into music, and appreciating the imperfection there. One of the reasons I’ve always liked going to see live music is because the show’s an experience, it’s different. One of the reasons I love jazz is because of the improvisation, the one-offness of it.

I think there’s going to be a resurgence and a yearning towards the human imperfection of the human experience being more and more prized — the human factor in all of this work. This gets put under the authenticity lens. You even think about the trends around film photography and vinyl and owned media that’s physical. This has been coming, and AI is just accelerating all of that.

Jonathan Hicken: Well, for all those executive directors and social impact leaders out there, this content reset is here. But stay with us through Designing Tomorrow this year. I think we’re going to be helping unpack all of it along the way.

Eric Ressler: Yeah, this is fun. There’s a lot more to unpack here that we’ll do in future episodes. And listeners, if you’re curious about showing up in 2026 on your content strategy, check the show notes — we’ll be sure to put some tasty morsels in there for you.

Jonathan Hicken: Fantastic. Thank you, Eric.

Eric Ressler: Thanks, Jonathan. If you enjoyed today’s episode, please be sure to hit like and subscribe or leave us a comment. It really helps. 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.

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.

Every organization has a “someday” list.

The rebrand that never quite gets prioritized. The content strategy that’s been “in the works” for three years. The bold idea that came up in a board meeting, got tabled for further discussion — and was never discussed again.

But what if the right time already came and went?

In this episode, Eric and Jonathan go behind the scenes on a project that almost didn’t happen: building Seymour Studios, a turnkey media space designed to make storytelling fast, simple, and accessible for the social impact community in Santa Cruz.

Eric pitched this same concept to another local organization months earlier. They stalled. Jonathan saw the potential, moved on it, and now the opportunities are already flowing in.

They cover:

➔ Why rigid strategic plans often kill the opportunities they’re meant to create.
➔ The hidden friction that stops good ideas from ever getting off the ground.
➔ How to screen opportunities without defaulting to “someday.”
➔ What it looks like to pursue the end goal relentlessly — while staying flexible on the journey.
➔ The early returns from building momentum instead of waiting for perfect conditions.

If you’ve ever felt stuck between vision and execution — or wondered why some organizations seem to move while others stay frozen — this conversation will challenge how you think about timing, risk, and the real cost of deferral.

Stop waiting. Start building.

Episode Highlights

• [00:00] Introduction: The cost of “someday” and why opportunities rarely wait

• [01:40] The pattern Eric has seen over 16 years of working with nonprofits

• [03:05] How the studio idea came to be, and why another org passed

• [04:38] Jonathan’s lightbulb moment: connecting the studio to a longstanding problem

• [06:18] The hidden friction of media production (and why it kills creativity)

• [08:00] Other flavors of “someday” — board approval, distractions, unclear ROI

• [10:04] Leadership, culture, and organizations in motion

• [14:05] Balancing opportunism with focus: how to avoid shiny object syndrome

• [14:30] Relentless pursuit of the end goal vs. rigid journey planning

• [17:30] Screening opportunities: the donor/supporter “look them in the face” test

• [19:49] Early feedback from the community — and why people see themselves in it

• [22:02] The future of content: accessible, human, less polished, more interesting

• [23:27] The quantity play: why more stories > fewer perfect ones

• [25:00] Challenge to listeners: shed the someday mentality in 2026

Notable Quotes

“We’re so focused on the journey — what step we’re making, when, how much it’s going to cost — that when you build that rigidity into your plan, you’re not ready to take those opportunities that would get you to your end goal more quickly.” — Jonathan Hicken [14:30]

“Clarity of purpose — a really clear crystallized version of a vision — is what allows you to pursue that so relentlessly. Because if that’s vague, you just can’t do it by definition.” — Eric Ressler [15:05]

“It’s not loosey-goosey. It’s one where I feel like I could look a donor or supporter in the face and say, ‘This is going to help us deliver impact more quickly.’” — Jonathan Hicken [17:50]

“That energy and that buzz is what creates capacity, what creates opportunity — not the other way around.” — Eric Ressler [10:45]

“Get your reps in. The next time someone pitches you a new idea, screen it against your vision, your end state, and your near-term goals. Build that muscle.” — Jonathan Hicken [25:43]

“More and more, we have to be better communicators in this space. How do we take those big scientific concepts that are esoteric, inaccessible, unequitable — and break them down into stories, into narratives, into conversations that are more accessible, more human.” — Eric Ressler [22:02]

P.S. — Feeling stuck between where you are and where you know you could be? Cosmic helps social impact orgs build trust through story-rich brands, compelling campaigns, and values-aligned strategy. Let’s talk about how to get moving: https://designbycosmic.com/

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.

After months away, Jonathan Hicken returns to Designing Tomorrow — and this time, we’re recording from the brand new Seymour Studios at the Seymour Center in Santa Cruz.

In this episode, Eric and Jonathan take a real look back at 2025: a year that felt like a grind but delivered surprising wins across the sector. They dig into what the data actually says about giving (spoiler: it’s not all doom), why the story you tell yourself shapes your reality, what it means to actually invest in storytelling instead of just talking about it, and the personal lessons they’re carrying into 2026.

If you’re ready to shed 2025 and enter the new year with big moves and big ideas, this one’s for you.

Notable Quotes

“Those beliefs drive your actions, they drive your perception, they drive how you show up in real life, how you show up in your work.” — Eric [28:51]

“We just kept banging that drum. We kept banging that drum as long as things were working and we were moving in the same direction.” — Jonathan [25:31]

“Everyone says they want to do storytelling. You just don’t see it in their investments. You don’t see it in their energy. You don’t see it in the dollars.” — Eric [20:07]

“Vulnerability and radical honesty — it’s been a superpower. And it’s something I want to carry into 2026.” — Jonathan [31:16]

“In my work, I’m seeing these huge wins from these growing nonprofit organizations, and it just gave me a lot of hope and kept me going.” — Eric [10:00]

Episode Highlights

0:00 — Jonathan’s Back: Welcome to Seymour Studios
2:06 — Looking Back on 2025: What Went Well
3:43 — The $350K House Party and Santa Cruz Generosity
5:00 — Why Jonathan’s Been Missing from the Show
6:12 — The Interviews That Kept Us Going
6:30 — Major Donor Giving Is Up (What the Data Says)
7:46 — Should We Worry About Fewer Donors?
9:00 — Client Wins: $13M, $14M, and More
11:00 — How Cosmic Celebrates Client Success
12:43 — Eating Our Own Dog Food: The Case for Support
15:00 — The Questions That Forced Hard Conversations
17:00 — What Even Is a Case for Support?
19:00 — Building a Storytelling Engine (Content Brokerage)
20:07 — Why Most Orgs Talk Storytelling But Don’t Invest
22:00 — What Charity Water Knows About Storytelling
23:26 — Getting the Whole Team Aligned
25:27 — Growth Isn’t Linear, It’s Cyclical
27:00 — Big Moves Aren’t Knee-Jerk (They’re Secretly Researched)
28:00 — “What If It’s Not All Falling Apart?”
30:00 — Turning 40 and the Midlife Recalibration
30:44 — Jonathan on Vulnerability and Radical Honesty
32:00 — Thank You, Listeners — and What’s Next

Referenced Episodes & Resources

Fewer Donors, Bigger Checks: Interpreting the Latest Giving Data https://designbycosmic.com/podcast/nonprofit-donor-trends-2025/

Growth Isn’t Linear. It’s Cyclical. https://designbycosmic.com/podcast/growth-isnt-linear.-its-cyclical.

How to Build a Strong Case for Support https://designbycosmic.com/podcast/how-to-build-a-strong-case-for-support/

Seymour Center Case for Support Example
https://www.canva.com/design/DAG4hkxvfvQ/zRnCdWPZkovr3v-KSSyTyg/view

Connect

Cosmic:

https://designbycosmic.com

Seymour Marine Discovery Center:

https://seymourcenter.ucsc.edu

P.S. — Feeling a disconnect between your mission and your brand? Cosmic helps social impact leaders build trust through story-rich brands, compelling campaigns, and values-aligned strategy. Let’s talk about how to elevate your impact:

https://designbycosmic.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.

I’ve been thinking a lot lately about the gap between what we know we need to do and what we’re actually willing to do.

Not in theory. In practice. When the stakes are real and the consequences matter.

This year, I’ve had to make several decisions that I’ve been putting off, some of them for years. Decisions I knew were right but that felt impossible in the moment. Walking away from revenue that no longer aligned with where we’re headed. Restructuring relationships that were incongruent with our vision. Letting go of ways of working that served us well in the past but were actively blocking our future.

Each time, there was a moment where I had to choose: the comfort of what I knew, or the reality of what I needed.

It boils down to a simple truth: What got you here might just be exactly what’s holding you back.

The Pattern I Keep Seeing

Here’s what I’ve learned after 15 years working with hundreds of social impact organizations:

The biggest barrier to your next stage of growth isn’t lack of vision. It isn’t lack of funding. It isn’t even lack of capacity.

It’s attachment to what got you here.

The program that built your reputation but no longer serves your mission.

The funder who strings you along with just enough support to keep you dependent but never enough to let you scale.

The board member who helped you survive your startup phase but is now dragging your strategic thinking backward.

The team member you love, who’s been with you from the beginning, but who can no longer execute at the level your organization needs.

The “we’ve always done it this way” processes that made sense when you were scrappy but now slow you down.

The old partnerships, old structures, old identities that you’re clinging to — even though you know, deep down, they’re what’s keeping you stuck.

And the hardest part isn’t identifying what needs to change. You already know what needs to change. The hardest part is admitting you’ve been choosing comfort over growth. It’s deciding that you’re done pretending otherwise, and taking the very actions you’ve been putting off.

But sometimes it feels like you’re powerless to make that change. Or it feels like betrayal. Or it feels too risky, especially when things are already fragile.

So you don’t. And you stay stuck.

Why This Is Especially True in Social Impact

I’ve seen this pattern play out differently in the social impact space than anywhere else.

Mission-driven leaders have a unique form of stubbornness — one that’s rooted in deep values and genuine care. You’re not motivated by profit or fame or status. You’re motivated by impact. By justice. By the people and communities you serve.

And that’s beautiful. That’s why this work matters.

But it also means you’re more likely to:

• Keep underperforming programs running because shutting them down feels like abandoning people

• Accept toxic funding relationships because “any money is better than no money”

• Tolerate team dysfunction because firing someone feels like a moral failure

• Avoid hard conversations because you don’t want to be “that kind of leader”

You tell yourself you’re being loyal when you’re actually just avoiding a hard conversation. You call it resilience when it’s really just fear of change. You convince yourself that holding on is the same as showing up for your mission.

But it’s not.

What you’re actually doing is protecting your comfort at the expense of your impact.

And the sector suffers for it. Because when individual organizations can’t break through to their next stage, the entire ecosystem stays stuck.

What Actually Happens When You Let Go

I’ve watched organizations make the hard call. Let go of the beloved but underperforming program. Walk away from the funder who’s more trouble than they’re worth. Restructure the team even when it’s painful. Sunset the old brand identity that served them well but no longer represents where they’re going.

And here’s what happens:

Short-term discomfort. Long-term momentum.

There’s grief. There’s loss. There’s the nauseating feeling that you’re making a terrible mistake.

But then space opens up. New partnerships become possible. The team breathes. Strategy gets clearer. You stop spending 80% of your energy maintaining what’s no longer working and start spending it on building what comes next.

Because here’s the thing about transformation that nobody tells you:

It doesn’t happen in strategy decks or visioning retreats. It happens in the daily micro-decisions where you choose your future over your past.

Every conversation with that problem funder is a choice.
Every meeting with that underperforming team member is a choice.
Every hour you spend trying to force your new strategy into your old structures is a choice.

And those choices compound. They either move you one step closer to where you need to be, or one step further away.

The Real Cost of Inaction

When you refuse to let go of what’s no longer working, you’re not just holding your organization back. You’re holding yourself back, too.

As a leader. As a strategist. As someone who’s trying to build something meaningful in the world.

Because every time you accommodate dysfunction to preserve a relationship, you’re teaching yourself that your boundaries don’t matter.

Every time you absorb the cost of someone else’s inability to follow through, you’re reinforcing the belief that your capacity is infinite and your needs are secondary.

Every time you say yes when you really mean no, you’re chipping away at your ability to lead with clarity and conviction.

And eventually, you stop trusting yourself. You stop believing in yourself. You start to wonder if maybe the problem is you — maybe you’re just not good enough, not strategic enough, not resilient enough to make this work.

But that’s not true, unless you are unwilling the make the difficult, uncomfortable, but ultimately right choices.

And the only way to become that leader is to practice being that leader. Every single day. In every single decision.

This is the work. Not the creative work, not the strategic work — the identity work. The shedding of who you were so you can become who you need to be.

What Are You Holding On To?

If you’re reading this and feeling the weight of something you know you need to let go of, here’s what you should to ask yourself:

Is this thing I’m holding onto protecting my mission, or is it protecting my comfort?

And here’s the harder question:

What would it cost you to let go? And what will it cost you if you don’t?

Because here’s the truth: letting go always costs something. There’s loss, there’s grief, there’s uncertainty. That discomfort is real.

But staying stuck costs more.

It costs you momentum. It costs you clarity. It costs you the opportunity to build what you’re actually capable of building.

And it costs the people you’re trying to serve, because every year you give up on your vision is a year you’re not reaching your full potential.

What I’m Choosing

I’m choosing to trust that the discomfort of letting go is better than the comfort of staying stuck.

I’m choosing to believe that the organizations and leaders who are ready for this conversation will find their way to partnership. And the ones who aren’t? They’re not meant to be part of this chapter.

And that’s okay.

The real win is the integrity between your truth and your actions. It’s knowing what you stand for. It’s trusting yourself enough to make the hard call and live with the consequences.

And that’s the only way you ever actually grow.

So here’s my question for you:

What are you clinging to that’s blocking your next chapter?

Not the easy answer. The real one. The thing you know needs to change but you’ve been too afraid, too loyal, too exhausted to address.

Because I promise you: it’s not a mystery. You already know what it is.

The only question is whether you’re willing to let go.

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