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.

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/

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/

Your case for support isn’t just a fundraising tool — it’s a strategic asset that can align your messaging, mobilize your team, and inspire serious investment in your mission. But only if you get it right.

In this episode, Eric and Jonathan walk through a 5-part framework to help you build a clear, compelling case that connects with hearts and minds — and opens doors.

➔ Why most cases for support skip the one question every donor is asking.
 ➔ The five ingredients of a persuasive narrative (and how to use them beyond fundraising).
 ➔ How to tailor your pitch without losing your integrity.
 ➔ Why “bragging” is essential — and how to do it without turning people off.
 ➔ A practical way to turn your case into a year-long content and management tool.

Whether you’re prepping for a major campaign or just trying to sharpen your story, this episode will help you rethink your approach — and give your supporters a reason to say yes.

Don't just ask for support. Make the case.

Episode Highlights:

• [00:00] Why your case for support must start with clarity

• [01:24] Why this isn’t just for capital campaigns

• [02:40] Step 1 – The Why

• [04:27] Step 2 – The Vision

• [07:44] Step 3 – The Strategy

• [10:30] Step 4 – Credibility

• [12:53] Brag or stay humble? Striking the right tone with funders

• [14:27] Step 5 – The Ask

• [21:42] Building a forecasting pipeline for major gifts

• [24:13] Mapping donor motivations to maximize engagement

• [25:40] Bonus: Turn your case for support into your content strategy

Resources:

• Better Brand Storytelling

• Rep. Katie Porter's Messaging Tactics

• Campaign Messaging for Major Donors vs. Grassroots Supporters

• Supercharge Your Social Enterprise’s Proof of Impact

• Your Theory of Change isn't finished until your Grandma can understand it.

• Change you make

• Your Organization’s Credibility Rests on Your Website

• Metrics or impact storytelling

• What to Do When Funders Say "No" 

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan challenge the traditional definition of efficiency and unpack why it can be a trap for social impact organizations. From donor pressure to staff burnout, they explore how the pursuit of efficiency often undermines effectiveness — and what to prioritize instead if you're serious about sustainable, meaningful impact.

➔ Why efficiency and innovation often live at opposite ends of the spectrum.
 ➔ How serving the process can slowly kill your mission.
 ➔ What to say when funders fixate on overhead (and how to shift the conversation to impact).
 ➔ A smarter definition of efficiency: spending time on the right work, not just more work.
➔ What systemic inefficiency looks like — and how to fix it without burning everything down.

If you're feeling the pressure to cut corners, over-optimize, or stretch your team thin in the name of “efficiency,” this episode will help you step back, reframe the problem, and refocus on what actually moves the needle.

Don’t chase efficiency. Build for effectiveness.

Episode Highlights:

• [00:00] Redefining efficiency: Doing the right thing at the right time

• [01:49] Innovation vs. optimization

• [03:30] The cultural obsession with optimization—and its dangers

• [05:35] Real-world ad example: Efficiency as a byproduct of innovation

• [06:32] Smart systems vs. busywork: What efficiency should actually look like

• [08:07] The trap of measurable efficiency—and the loss of trust

• [09:08] “Serving the process”: The red flag that your culture may be off track

• [11:44] Bureaucracy, balance, and unintended harm

• [14:33] The overhead myth and how to push back effectively

• [18:16] When “efficiency” undermines your people

• [21:45] Sector-wide inefficiency

• [24:57] Effectiveness as the healthier north star

• [26:25] Diminishing returns: Knowing when to stop optimizing

Resources:

• In Defense of Moonshots

• Breaking the Starvation Cycle 

• Marketing Isn’t Overhead

• Are You Using Your Power?

• MacKenzie Scott Proved Unrestricted Funding Works

• Supercharge Your Mission
  
  

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan dig into the storytelling struggles that come with multifaceted missions — and offer a practical framework to help you cut through the noise, focus your narrative, and connect more powerfully with your audiences.

➔ The one question every leader should ask before blaming the messaging.
 ➔ How to tell an emotionally compelling story without oversimplifying your mission.
➔ Why most orgs don’t have a storytelling problem — they have a focus problem.
➔ What to do when “just one story” feels impossible.
➔ A simple test to make sure your message really matters to anyone outside your team.

If your communications are feeling muddy, scattered, or just too complex to explain, this episode will help you zoom out, refocus, and tell a story people will actually remember — and care about.

Don't try to say it all. Say the one thing that matters most.

Episode Highlights:

• [00:00] - The complexity trap: “How do we take these complex missions and weave simple, compelling emotional narratives?”

• [01:33] - First things first: Is this actually a storytelling issue—or a lack of focus?
  [02:50] - The everything-all-at-once problem: How pride in breadth can dilute clarity.

• [04:15] - Non-profit existentialism: “What am I doing with my life?” as a strategic tool.

• [05:44] - The theory of change litmus test: Can you explain how your work creates change?
  [09:11] - The problem behind your problem: Defining your challenge before crafting your message.

• [10:33] - Unique qualifications: What makes your organization the right one to do this work?

• [13:24] - The “So What” test: Distill your purpose with this 3-step drill-down exercise.

• [15:25] - You don’t need to tell it all: The danger of overexplaining.
  [18:34] - Different stories for different audiences: Why stakeholder-specific storytelling is essential.

• [21:18] - Start with the simplest story: Lead with what’s most intuitive—expand later.

Resources:

• Better Brand Storytelling

• Defeat Mission Creep

• Supercharge Your Mission

• Your Theory of Change

• Messaging Framework

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan dive into the real tradeoffs of major donor programs — the power dynamics, the mission drift moments, and the long runway it takes to build trust at scale. Whether you're building from scratch or recalibrating your fundraising strategy, this candid conversation will help you weigh the potential upside and the pitfalls.

➔ When a major gift is actually too costly to accept
 ➔ How to spot — and avoid — single points of failure in your revenue model
 ➔ The true time horizon for major donor ROI (and why it’s rarely fast)
 ➔ How to handle “friendly pressure” from high-influence funders
 ➔ Practical steps to build a resilient, aligned donor pipeline

If you’re wondering whether a major donor strategy is worth the effort — or how to manage the one you already have — this episode gives you the clarity, caution, and confidence to move forward wisely.

Episode Highlights:

• [00:00] Major donors: blessing or burden? Jonathan reflects on a recent transformative gift and what it reveals.

• [02:45] - When major donors help (or hinder) the mission.

• [04:56] - Why strings aren’t always visible, and what to do about it.

• [07:52] - Would you want this donor on your team if they weren’t giving?

• [10:00] - The real cost and timeline of launching a major donor program.

• [12:35] Donor, grant, or individual giving? Eric and Jonathan weigh the most scalable strategies.

• [15:28] Unrestricted funding, or instability? The tradeoff that comes with flexibility.

• [21:30] - What happens when a major donor exits?

• [24:44] - The long tail and payoff of building grassroots support.

• [26:51] - How to lead a major donor program with intentionality.

Resources:

• Article - How to Differentiate Campaign Messaging for Major Donors vs. Grassroots Supporters

• Article - How to Create the Conditions for Sustainable Revenue

• Article - Top 5 Features Your Nonprofit Needs in a Donor Management Platform

• Article - Going All In: A Digital-First Guide to Sustained Nonprofit Fundraising

• Article - Build a Healthy Social Impact Community with these 5 Pillars

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan unpack how to rethink your approach to reporting — and turn your annual impact story into one of your organization’s most powerful strategic tools.

➔ The secret ingredient of high-performing reports.
 ➔ The real ROI of a well-designed impact report — and how to measure success beyond the PDF.
 ➔ A simple way to start small: what a minimum viable impact report looks like (and why it’s enough).
 ➔ How digital and physical formats can work together to spark deeper connection with supporters.
 ➔ Why your report is only as good as your distribution strategy — and how to plan one that delivers.

If your reports are starting to feel more like homework than momentum-builders, this episode will help you reframe the process — and unlock new energy, clarity, and results from one of your most overlooked assets.

Don’t just report impact. Design it. 

Episode Highlights:

• [00:00] - Why impact reports must go beyond check-the-box compliance.

• [01:43] - Design choices, storytelling moments, and a surprising community favorite.

• [04:34] - Jonathan opens up about why even EDs can dread it—and how to reframe it.

• [06:16] - Why that one piece matters more than you think.

• [07:41] - Conversation starters, trust builders, and supporter affirmation.

• [10:57] Why your report must have a digital component and how to make print feel like a premium experience.

• [14:34] - When to go immersive, when to go tangible.

• [17:25] Build your report all year long. Treat stories and metrics as ingredients, not afterthoughts.

• [21:03] - Personalized impact reports are the new frontier.

• [23:32] - Why “post and pray” doesn’t work, and what to do instead.

• [26:09] - How chunking up content triples conversions.

Resources:

• Case Study - Equality Fund

• Article - The Benefits of a Digital Annual Report

• Article - How to Prepare for Your Digital Annual Report

• Article -Prove it or Lose it: Why Proof of Impact Matters in the Social Impact Space

• Article - Turning Stats Into Stories: Supercharge Your Social Enterprise’s Proof of Impact

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan explore what it really takes to sell a bold new vision — even when the work is still taking shape.

➔ Why internal conviction is the first — and most underrated — step to building external trust.
 ➔ How to frame your future vision when your current reality doesn’t match it (yet).
 ➔ The power of showing instead of telling — and what that looks like with no budget.
 ➔ Why funders are often more excited by possibility than proof — and how to use that to your advantage.
 ➔ A real-world playbook for prototyping your vision, building buy-in, and navigating the messy middle.

If you're leading through change, launching something new, or reinventing your organization’s direction, this conversation will help you craft a message that inspires belief — before the results are in.

You don’t need to have it all figured out. You just need to sell what’s possible.

Episode Highlights:

• [00:00] - Eric and Jonathan kick off with a definition that goes beyond mission statements.

• [01:12] - Jonathan shares real talk about leading through transition at the Seymour Center.

• [02:13] - Eric maps the vision lifecycle from insight to realization.

• [05:13] - Why writing one too early can backfire—and what to do instead.

• [07:02] - Eric recounts Cosmic’s pivot to social impact and what it took to bring his team along.

• [11:48] - Jonathan’s tips for gaining internal and external buy-in.

• [14:48] - Funders and stakeholders appreciate realism—if you frame it right.

• [18:35] - A smart messaging pivot that worked for Seymour Center.

• [19:56] - How DIY prototypes and low-budget demos helped seed a big vision.

• [24:17] - A thought-provoking exchange on fluidity, revision, and what comes next.

• [28:42] - Two different leadership styles—and how to make both work for you.

Quotes:

• "It's a vision of a new way of what could be, but what is not yet true." – Eric Ressler [00:00]

• "You as the executive… you really, truly, deeply in yourself believe in the potential." – Jonathan Hicken [04:51]

• "Vision and mission statements sometimes get an outsized amount of attention… I'd rather see more time on having a compelling vision." – Eric Ressler [05:13]

• "The single best way to sell a vision when you’re not delivering yet? Start prototyping." – Jonathan Hicken [19:56]

Resources:

• Article - How Your Purpose, Vision, and Mission Can Guide Better Brand Storytelling

• Podcast - How to Stop Planning and Start Doing

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

Episode Highlights:

• [00:00] Why “the problem” isn’t always one thing

• [01:51] Intro to the 3-step content strategy: Problem, impact, vision

• [02:39] Naming and framing the problem: It’s more powerful than you think

• [05:10] Problem sets, not problems: How to tell different layers of the same story

• [07:11] Scale matters: Matching problem scope to your audience

• [08:09] Real-world example: How 35 Mile Foundation names the digital divide

• [10:53] Step 2 – Share your impact: Why it’s essential (and how to go deeper)

• [13:08] The “So what?” test: Making your impact stories hit harder

• [16:22] Human + data: Layering emotional and statistical storytelling

• [18:23] Why impact storytelling builds trust

• [20:15] From anecdotes to narratives: Connecting the dots for your audience

• [21:47] The results: Jonathan shares how this shifted fundraising outcomes

• [24:15] Step 3 – Share your vision: Moving from vague statements to bold future casting

• [25:42] Vision isn’t a promise—it’s a rallying cry

• [28:09] Make it visceral: Help people imagine your world

• [29:50] It’s not “the” vision—it’s visions, plural

• [30:42] The takeaway: Beat the drum until you're bored

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

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Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Eric and Jonathan unpack the three types of objections every social impact leader will face: the silent no, the vague no, and the hard no. They explore why each shows up, what it’s really signaling, and how to respond in a way that transforms rejection into relationship. Whether you're navigating donor hesitancy or partner pushback, you'll walk away with practical tools to shift conversations from confusion and avoidance to clarity, trust, and—yes—sometimes even a yes.

Episode Highlights:

• [00:00] - The 3 types of objections: Silence, vagueness, and direct no’s

• [01:42] - A real-world win: How reframing a donor’s “no” unlocked major funding

• [03:03] - Ghosted? Strategies for re-engaging silent prospects

• [05:59] - Automated follow-ups that work: Respectful nudging and content-driven touches

• [07:19] - Low-effort asks: Using newsletters to reignite dormant conversations

• [08:22] - The “breakup email” that gets responses: Permission to say no

• [10:43] - Why silence feels personal—and how to shift your mindset

• [12:04] - Vague rejections: How to politely mine for clarity

• [13:08] - Exact language that invites honest feedback

• [15:17] - Is it just the money? A powerful question to uncover root issues

• [17:43] - When “scaling down” won’t serve you—or them

• [19:17] - Invite donors into partnership: What funders really want

• [21:07] - Objections as insights: What “no” reveals about your positioning

• [22:19] - Flip your mindset: Think 70% about what they want to hear

• [24:06] - Fit-first fundraising: 3 guiding questions before accepting money

• [25:19] - Mission creep warning: Why not all dollars are worth it

• [27:20] - The takeaway: Always try to get to a direct “no”—and know why it happened

Quotes:

• “You have to become an irresistible fundee—for them.” –Jonathan Hicken [22:32]

• “Funders want to make an impact on something they care about. Period.” –Eric Ressler [23:25]

Resources:

• Article - Want Foundations to Fund Your Work? Speak Their Language. Here's How.

• Article - How to Embrace (and Own) Your Nonprofit's Digital Fundraising

• Article - 8 Reasons Why Donors Aren’t Giving on Your Nonprofit’s Website

• Article - Funders: Your Obligation to Social Impact Goes Beyond Giving Money

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

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Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

• The surprising parallels to early COVID-era chaos (and how that can inform today’s crisis response)

• Why you might need to ‘scale back’ strategically—and how to do it without losing your sense of purpose.

• The key to rallying donors, partners, and staff using open communication and powerful impact stories.

• The #1 mistake leaders make when forced to let go of talented people (hint: it involves your support network)
  
  

Whether you’re facing sudden federal cutbacks or seeking to maintain momentum in a tough environment, this episode is packed with actionable insights to help you adapt without compromising your impact.

Don’t let external forces derail your organization’s good work. Tune in now and learn how to protect your mission, inspire your team, and stay resilient. Even when the odds feel stacked against you.

Episode Highlights:

[00:00] - View from the field: What social impact leaders are experiencing right now

[01:50] - The ripple effects of federal policy shifts: Retrenchment and risk mitigation

[03:40] - “It feels like early COVID again”: Chaos, fear, and identity crisis in the sector

[06:20] - The grift narrative: Online misinformation and the backlash against nonprofits

[07:23] - Getting hyper-local: The strategic (and risky) pivot toward smaller spheres

[08:38] - Unprecedented losses: Real-world stories of scale-downs and shutdowns

[10:28] - Why the blame game backfires: Compassion over critique

[13:17] - From freeze to activation: What separated resilient orgs during COVID

[15:47] - "Now is the best time": Standing strong in your community

[18:22] - A call to funders: Emergency support is urgently needed—again

[19:25] - Action steps for leaders: Reconnect, recommit, and re-partner

[21:34] - Leading through contraction: Compassionate downsizing and clarity of mission

[23:53] - Over-communicating with intention: The power of transparency and storytelling

Quotes:

• “Now is the best time to stand up for science… for a community that's trying to protect itself from a changing environment.” – Jonathan Hicken [00:15]

• “We need to be better at getting these stories out in a way that actually cuts through.” – Eric Ressler [07:07]

• “There’s almost this feeling that we’re not allowed to be successful or be optimistic right now.” – Jonathan Hicken [11:30]

• “Organizations that activated quickly—even imperfectly—came out stronger.” – Eric Ressler  [13:50]

• “Start to prepare to help the people on your team land on their feet.” – Jonathan Hicken [22:25]

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this raw and unfiltered finale, they look back on the leadership decisions, strategic misfires, hiring blunders, and marketing missteps that didn’t go according to plan. No spin. No gloss. Just two founders owning their hardest lessons out loud.

Why end the season like this? Because mistakes aren’t just part of leadership — they are leadership. If we want a social impact sector that embraces failure as fuel for growth, we have to start by telling the truth about what we've gotten wrong.

So here it is.

Episode Highlights:

[00:00] Opening: “Today we're going to talk about all the shit we've messed up.”

[01:35] Why talk about mistakes at all?

[02:23] Jonathan’s board breakup

[05:34] Eric’s accidental leadership path

[08:04] Burnout and showing up as a leader

[10:26] When design isn’t enough

[13:28] Strategic blindspots

[18:17] “I blind copied them.”

[20:48] Firing with (or without) dignity

[27:07] Going too wide in marketing

[28:53] The cost of not marketing

[33:30] When vision stalls

Resources:

• Podcast - Rethinking Failure in Social Impact

• Podcast - How to Stop Planning and Start Doing - Discussion of MVS framework

• Podcast - Designing a Purpose and Strategy with Eric Ressler

• Article - Test Your Niche to Develop Your Organization’s Superpower

• Article - 8 Key Ingredients to Defining Your Social Impact Niche

• Article - How to Build a Next-level Content Strategy

• Article - A Guide to Social Impact Marketing Through Brand-building

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

In this episode, Jonathan brings a live challenge to the table: a bold new vision for the Seymour Center that could reposition it as a hub for climate solutions and STEM leadership — but it comes with branding risks, potential backlash, and major funding implications.

Eric coaches him through the decision-making, exploring when to stay quiet, when to go big, and how to avoid mission creep without losing momentum. This is real-time strategy, storytelling, and nonprofit leadership — unfiltered.

Episode Highlights:

[00:00] Jonathan tees up a live strategy session — and asks Eric to coach him
[01:12] Why the Seymour Center is shifting toward climate resilience
[03:09] The dual problem: climate impact and STEM education gaps
[05:49] What other groups can’t do — and where Seymour fits in
[07:02] How anxiety around climate is shaping a new kind of science education
[09:59] Is this a pivot, an evolution, or mission creep?
[11:34] Program tweaks vs. a bigger vision shift — what's on the line
[13:26] Fundraising, capital campaigns, and messaging trade-offs
[15:44] The two-problem narrative — and how to avoid confusing funders
[17:21] High school students as solution-makers (and a current gap)
[18:25] Pilot vs. launch — the fear of going public too soon
[21:00] Pushback: are we abandoning the ocean?
[22:23] Dropping the term “climate change” — and why
[23:00] What would Jonathan need to say “no” to?
[24:25] The risk of staying the same — and the case for going bold
[29:23] Why this is about relevance — not reinvention
[30:14] Eric's honest advice: it’s time
[31:12] “You’re not shooting from the hip anymore.”

Resources:

• Seymour Marine Discovery Center

• Article - Test Your Niche to Develop Your Organization’s Superpower

• Article - 8 Key Ingredients to Defining Your Social Impact Niche

• Article - The #1 Mistake Social Impact Organizations Make in Their Digital Storytelling

• Article - 10 Tips for Building a Community Around Your Cause

• Article - Are You Bold Enough To Lead The Conversation?

• Podcast - How to Stop Planning and Start Doing - Discussion of MVS framework

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

So how do you build a revenue model that works? One that’s not just about survival, but about impact at scale?

In this episode, Eric and Jonathan dive into how funding models are evolving, why earned revenue is becoming a bigger part of the equation, and how leaders can think more strategically about their revenue mix. They also explore the key trade-offs between major gifts, grants, corporate partnerships, and earned income, and how to determine the best fit for your organization.

If you’re feeling stuck in the same fundraising cycle—or wondering how to make your revenue more sustainable—this conversation is for you.

Episode Highlights:
[00:00] Introduction – The funding landscape is shifting. Is your revenue strategy keeping up?
 [00:20] Why many orgs struggle to fully fund their mission – The hidden gap in nonprofit and social enterprise revenue
 [02:44] Earned revenue: The opportunity (and challenge) – Why this model is gaining traction
 [04:37] Is donating profits better than direct impact? – The pros and cons of different funding models
 [06:56] What we can learn from Patagonia – Mission-driven business models in action
 [09:35] Are social enterprises just businesses? – Finding the balance between impact and revenue
 [12:22] Authenticity vs. cause-washing – Why your origin story matters in funding decisions
 [15:30] Nonprofit revenue models: Expanding beyond traditional fundraising
 [18:31] Your revenue model needs to evolve – How to move beyond what’s worked in the past
 [21:25] The small donor vs. major donor dilemma – Who should you prioritize?
 [27:09] Building a stronger donor pipeline – How small donors can turn into major donors
 [30:22] The role of grants, corporate giving, and capital campaigns – Smart strategies for diversification
 [41:44] Five key questions to assess your funding strategy – What to ask before making a shift
 [42:23] Final thoughts – Funding models that drive long-term impact

Resources:

• Article - 8 Successful Give-Back Models for Social Enterprises

• Article - Is the Buy-One-Give-One Model Dead? TOMS and the Future of Social Enterprises

• Article - How to Create the Conditions for Sustainable Revenue

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

So how do you build credibility, mobilize communities, and create real impact when attention is scattered and trust is eroding?

In this episode, Eric and Jonathan break down the new realities of marketing and media—the rise of digital tribalism, the fine line between authenticity and performance, and why the old marketing playbook no longer works.

Episode Highlights:

⏳ [00:00] A Changing Landscape – Why today’s media environment is unlike anything we’ve seen before.
 ⏳ [02:46] Misinformation, AI, and Media Silos – How rapid shifts in digital communication are reshaping public trust.
 ⏳ [06:29] The Attention Economy is Broken – We have more information than ever—so why do people feel more disconnected?
 ⏳ [09:40] Should Your Organization Speak Out? – The pressure to comment on every social issue vs. staying mission-focused.
 ⏳ [12:48] Authenticity or Performance? – The rise of “authenticity washing” and why your audience sees through it.
 ⏳ [17:14] The Death of Traditional Marketing – Why the old broadcasting model no longer works—and what’s replacing it.
 ⏳ [21:24] From Broadcast to Relationships – How social impact leaders can shift their approach to build real trust.
 ⏳ [26:00] The Future of Digital Trust – How organizations can navigate the chaos and create meaningful connections.

Notable Quotes:

• "We are in the middle of the biggest shift in media and marketing of our lifetimes." – Eric Ressler [01:26]

• "I know that my reaction to the world as it is, has been to sort of shrink my sphere of attention and sort of align my attention with where my ability to make impact overlaps." – Jonathan Hicken [07:31]

• "If we don’t actually take action on the things we say, is it really authenticity—or just another marketing play?" – Jonathan Hicken [12:48]

Resources:

• The Lookout

• Article - Don’t Build Your Brand on Rented Land

• Article - Top 10 Mistakes Social Impact Websites Make

• Article - Develop a Distribution-First Mindset to Win in the Attention Economy

• Article - How to Defeat the 3 Toughest Challenges All Nonprofits Face

• Article - 4 Scroll-Stopping Digital Experiences to Inspire Your Nonprofit's Content

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

Measuring impact is especially difficult when change happens over years or even decades, and when the outcomes are tied to complex, systemic issues. On top of that, the process of evaluation and measurement can feel like extra work — another task on an already full plate. 

But without it, we risk relying on anecdotes and vibes instead of real data to prove we’re making a difference.

In this episode, Eric and Jonathan break down:

• The difference between evaluation and measurement

• Why tracking the wrong metrics can hurt your mission

• How to measure impact without faking it. 

• Three critical pillars of impact evaluation

• How to avoid the pitfalls of mission creep while staying focused on what your organization does best.

If you’re struggling to track the real impact of your work — or wondering how to balance storytelling with hard data — this conversation is for you.

Episode Highlights:

[00:00] Why Impact Evaluation Is So Hard

• Measuring success isn’t just about external outcomes—it’s about internal sustainability too.

• Why some nonprofits don’t track their impact (and why that’s a problem).

[01:22] Evaluation vs. Measurement: What’s the Difference?

• Evaluation = the big picture. Measurement = the tools.

• Why confusing the two can lead to misleading conclusions.

[03:50] The Challenge of Proving Long-Term Impact

• "That impact story took 20 years—how do you measure it in year two?"

• How to identify leading indicators that show progress before the full impact is realized.

[12:48] The Mission Creep Trap: Why Nonprofits Lose Focus

• The risk of trying to "fix everything" instead of doubling down on what you do best.

• How social impact leaders can take a page from academic research to avoid spreading too thin.

[15:39] Measuring Internal Sustainability: The Missing Piece

• If your organization is burning out, your impact won’t last.

• The three critical pillars of evaluation every nonprofit should track.

[23:46] A Simpler Way to Measure Success

• "Look, this doesn’t have to be complicated. Pick three things. Track them. Get better over time."

• How to integrate measurement into your culture—without hiring expensive consultants.

Resources:

• Article - Beyond Aesthetics: The ROI of Brand Building

• Article - Prove it or Lose it: Why Proof of Impact Matters in the Social Impact Space

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

Research shows that 90% of high-growth nonprofits rely on a single dominant funding source. Does that mean nonprofits should double down on one funding stream—or is there a smarter way to approach fundraising?

In this episode, Eric and Jonathan break down the real reasons some nonprofits scale while others stay stuck, the risks and rewards of focusing on a single revenue source, and how to strike the right balance between specialization and financial security. If your organization has struggled to gain traction, this conversation is a must-listen.

Episode Highlights:

• [00:00] Introduction – The surprising secret behind high-growth nonprofits

• [02:06] Diversification vs. specialization – Why common advice might be flawed

• [04:52] The power of focus – How narrowing your fundraising can fuel growth

• [08:15] Case Study: American Kidney Fund – A nonprofit that 10X’d revenue by shifting its funding strategy

• [12:43] The scaling challenge – Why growing nonprofits struggle with funding transitions

• [15:59] The reality of small donor programs – Why they’re harder to scale than many expect

• [18:51] When to kill an experiment – How to know when a funding strategy isn’t working

• [24:09] Deep partnerships vs. shallow diversification – The value of transformational funders
  [26:54] Should you grow at all? – Rethinking what growth means for your nonprofit

Resources:

• Article - SSIR - How Nonprofits Get Really Big

• Article - SSIR - Ten Nonprofit Funding Models

• Article - Why Social Impact Brands Struggle to Attract, Grow, and Retain Revenue

• Article - How to Create the Conditions for Sustainable Revenue

• Article - From Starvation to Sustainability: Rethinking Revenue in Social Impact

• American Kidney Fund

• Podcast - How to Stop Planning and Start Doing

• Article - Want Foundations to Fund Your Work? Speak Their Language. Here's How.

Listeners, now you can text us your comments or questions by clicking this link.

*** If you liked this episode, please help spread the word. Share with your friends or co-workers, post it to social media, “follow” or “subscribe” in your podcast app, or write a review on Apple Podcasts. We could not do this without you!

We love hearing feedback from our community, so please email us with your questions or comments — including topics you’d like us to cover in future episodes — at podcast@designbycosmic.com

Thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.