Designing Tomorrow: Creative Strategies for Social Impact

Most urgent fundraising appeals aren't truly urgent, and supporters can feel it. Constant false alarms erode donor trust, burn out teams, and leave nothing in reserve for the moments that really need a response. Ambitious work can move fast without the panic, and organizations that ration their urgency get a stronger response when it counts.

Episode Highlights: 

[00:01:20] Burnout, donor fatigue and the cost of always sounding frantic 
[00:04:55] What real urgency looks like: policy windows, funding cuts, sudden departures 
[00:08:10] Urgent for you, or urgent for your audience? 
[00:08:50] The urgency budget 
[00:09:40] How f...

Every cause depends on people knowing what's happening around them, and in a growing number of American communities, nobody is reporting it anymore. Matthew Copeland, Chief Executive and Editor of WyoFile, grew Wyoming's nonprofit newsroom from "three guys and a dog" people to sixteen by asking communities to fund journalism as a public good. He and Eric talk about why facts keep losing the fight for attention, and why every social impact leader should treat access to information as their second cause.

Episode Highlights: 

[00:02:05] WyoFile's mission and its three mandates 
[00:06:35] The collapse of...

Executive directors are expected to stay fired up all the time, and almost none of them do. Five years into leading the Seymour Center and fresh off a major milestone, Jonathan has hit a motivation slump. The conversation covers how to tell burnout from a slump, why success makes coasting tempting, and what helps leaders find the spark again.

Episode Highlights: 

[00:01:35] The success hangover after a major milestone 
[00:04:40] A leader's mood sets the team's temperature 
[00:06:35] The expectation that executive directors are always motivated 
[00:08:00] Self-determination theory: autonomy, competence, and relatedness 
[00:14:45] Pain...

Plenty of people still picture a museum as a quiet building with art on the walls and a staff whose job is to guard what's inside. Victoria Munro, Executive Director of the Alice Austen House, sees an advantage in that assumption: because museums look harmless from the outside, they have room to do serious work on social change and safe space. She explains how she took the velvet ropes down at a nationally designated site of LGBTQ+ history and built programs that turn visitors into co-creators.

Episode Highlights: 

[00:07:20] Museums as sites for contemporary c...

Social impact teams are happy to experiment. Where they struggle is admitting when the experiment fails. Jonathan and I dig into what design thinking and the scientific method can teach the sector, and why our refusal to name failure may be the thing holding impact back.

Episode Highlights: 

[00:03:30] Defining design thinking and the scientific method, side by side 
[00:08:00] The real failure point: we won't admit when things don't work 
[00:11:00] How science learned to publish its failures 
[00:18:00] A closed-door conference where funders aren't invited 
[00:24:30] In defense of design thinking 
[00:31:00] Knowin...

Philanthropy takes heat for being slow to move money, and learning usually gets the blame. 

Katherine Haugh, founder of the Convive Collective and a learning partner to some of the largest climate-focused philanthropies in the US and Europe, thinks that critique is fair but aimed at the wrong target. 

She and Eric dig into what's actually slowing foundations down, why learning so often becomes a way to dodge a decision, and the two things a foundation needs to genuinely learn.

Episode Highlights:

 [00:14:15] The real reason money moves slowly: control and...

Sandy Gould has spent 36 years studying where people's "superpowers" come from, and his answer is simple: the thing that makes you different is the same thing that lets you create what no one else can. In this conversation with Eric Ressler, the longtime GLAAD advisor and author of the forthcoming book Interlightening explains why conformity feels safe and isn't, and how the same rules that grow an individual grow an entire organization.

Episode Highlights: 

[00:03:00] From tech recruiting to GLAAD: a career built on unleashing people 
[00:05:30] Why the "why" leads to the what an...

Every leader in the social impact space has failures. But we rarely talk about them. We brush over them, reframe them, paper over them. Michelle Moog-Koussa thinks that's a mistake. She built the Bob Moog Foundation from $15,000 and a stack of Bob's crossed-out notebooks into a 20-year institution, and she runs it like a scientist: write down the idea, test it, and record an honest "didn't work" before turning the page.

Episode Highlights: 

[00:00:00] Why the social impact sector refuses to talk about failure 
[00:04:00] How 60,000 CaringBridge messages gave birth to a foundation 
[00:17:00] "You...

Every nonprofit leader has told themselves the same story: if funders just understood us, they'd fund us. Eric and Jonathan make the uncomfortable case that misunderstood impact is usually a you problem, and that what looks like a storytelling gap is almost always an identity gap. Close it, and funding, talent, and trust all get easier.

Episode Highlights: 

[00:01:15] The identity impact gap, defined 
[00:04:05] Why the gap quietly starves your funding 
[00:08:20] Why a widening gap can be a sign of growth 
[00:12:50] The three pillars: identity, expression, perception 
[00:30:00] "That's a you probl...

Most leaders know how to fight through a crisis. Almost nobody's ready for the moment things start working.

That's where Jonathan finds himself. Five years into running the Seymour Center, the survival years behind him. Funding's solid. The team's humming. He walks the halls, thinks "we're good," and tells me that stability feels strange. Almost uncomfortable. Like a problem he doesn't have the muscle for yet.

What I keep seeing after 15 years is that that's exactly how good organizations stall out. The bold, experimental swings that built the momentum are the first thing leaders quietly...

Is culture something you design, or does it emerge from the people you hire? I think you design it, through the decisions you make every day. Jonathan thinks it starts with the people and grows from there. The more we talked, the more the two came together: culture isn't your values poster, it's the consistent decisions a team makes over and over, plus the guardrails and tools that help everyone make them well. 

Episode Highlights: 

[00:03:22] Why culture always starts with who you hire 
[00:05:15] The case that American work culture is broken 
[00:15:19] The...

Two camps are forming around AI in the social impact space. One says boycott it. The other says you're already behind. Meanwhile, the biggest decisions are being made without us. 

Kaz McGrath and Stephen Silveira of Play (PLAI — Purpose-Led AI) make the case for stepping into the conversation, holding space for skeptics and builders at the same table, and using AI as a tool for imagination and mission.

Episode Highlights: 

[00:04:30] "You are behind" — the message the sector keeps hearing 
[00:08:00] What if nonprofit professionals became the builders? 
[00:15:30] Tracking endangered species in the A...

I have this problem, and I have it bad. At Cosmic I'm the bottleneck on more things than I should be, holding onto work because explaining it feels slower than just doing it. Jonathan doesn't get stuck there as often, so we dug into how executive directors and CEOs tell the bottlenecks that are right from the ones capping the whole org, and how to climb out of them.

Episode Highlights: 

[00:01:05] The bottleneck problem, named out loud 
[00:05:05] The real fear behind not letting go 
[00:12:08] Right sizing your role as the stakes ris...

Nonprofit leaders want more people to see their work, but almost none of them want to be the one posting about it. 

Saralynn Finn and I dig into what changes once you get past that resistance: story stems, a repeatable format for turning an ordinary moment into a post worth reading, and the difference between posting out of obligation and posting because something actually needs saying.

Saralynn brings a nonprofit CEO's 90-day LinkedIn experiment into it, and I bring my own inconsistent posting habits. This is a second conversation, picking up where an earlier episode o...

Every social impact leader believes in their mission.

Funders assume that too. What they actually want to know is why you, specifically, over the ten other orgs working the same issue, or the bigger name with more reach and a longer track record.

Most leaders answer with passion, good programs, being impactful. Genuine things that still don't add up to a strategy.

In this episode, Jonathan and I dig into a framework we use with clients constantly: naming your organization's exact role inside a broader social impact ecosystem, specific enough to defend, credible...

Sarah Newkirk became executive director of the Land Trust of Santa Cruz County in the middle of a capital campaign, the same week Jonathan Hicken took over at the Seymour Center. Five years later, she's landed a $15 million farmland deal, a wildlife crossing Caltrans is now replicating statewide, and a strategic plan built around one question: what would have to be true for this to work? She and Eric talk relationships, risk, and why joy is the real return on conservation work.

Episode Highlights:

[00:01:30] Coming in as the new ED mid-capital-campaign, the same...

There's a push right now to democratize strategic planning. Survey the community, poll the staff, put the big calls to a vote. 

I get the instinct, but it goes too far. Influence is not the same as decision-making power, and collapsing the two is how good orgs freeze. 

In this episode, Eric and Jonathan draft their ideal strategic planning teams fantasy-sports style from a pool of ten possible inputs, and work out how much weight each voice actually deserves.

Episode Highlights: 

[00:00:00] Drafting fantasy strategic planning teams from ten possible inp...

There's a number treated like gospel in philanthropy: the 5% annual payout private foundations are required to hit. It was written into law as a floor. 

Kristin Todd has watched it become a ceiling instead. After nearly two decades at the Daniels Fund, a $1.5 billion private foundation, she now leads the NoCo Foundation in Northern Colorado, where she's more than doubled annual grant-making by refusing to let donor dollars sit still.

Episode Highlights: 

[00:01:00] Running a $1.5 billion legacy fund vs. a nimble community foundation 
[00:07:00] Why mergers stopped being a taboo word for non...

Everyone keeps predicting the death of the website. First it was social, now it is AI. But it is still the one channel you actually own and control, which is exactly what makes it your most durable asset. So when a site has gone untouched for five years and a redo runs six figures, the real question is whether it is worth it, and when.

Episode Highlights:

[00:03:00] The identity impact gap, and when a redo is the wrong call 
[00:10:30] The 10-second homepage test 90% of nonprofit sites fail 
[00:13:00] Brand as coherence: the Ap...

For the last 50 years, we've operated under a single dominant idea: the purpose of business is to maximize shareholder value. But what if this whole era of extraction and short-termism isn't the natural order at all? What if it's just a blip? Sarah Gillard, CEO of Blueprint for Better Business, has spent 25 years inside major corporations watching what happens when companies forget what they're actually for, and she makes the case that business has both the power and the obligation to change it.

Episode Highlights:

[00:02:42] Two very different business models: profit maximization vs...

Jonathan recently learned that the Seymour Center is about to absorb a permanent new expense in the $150,000 to $200,000 range. On a $2.2 million operating budget, that's roughly 10% of the whole thing, and it's not a one-time hit. 

The instinct for most leaders is to pull back: tighten the budget, pause the big swings, and try again in a few years. But contraction changes the story you can tell funders, and that cost is harder to recover from than the budget hit itself.

Episode Highlights:

[00:00:30] Contract or keep pushing? The fundamental question. 
[00:02:00] Th...

Most social impact campaigns are built on two ingredients: information and emotion. The data makes the case. The storytelling makes people care. But caring, on its own, has a shelf life. Saralynn Finn, founder of Sett & Sley Consulting, joins Eric in the studio to argue that the third ingredient, what she calls "the hands", is where campaigns succeed or quietly die. Not more awareness, not more storytelling, but actionable pathways that give audiences something real to do with everything they now know and feel.

Episode Highlights:

[00:01:30] The head, heart, and hands framework for...

Most social impact leaders got into this work because they care deeply about the mission, not because they wanted to be public figures with opinions. But that instinct to stay quiet and let the work speak for itself may be doing more harm than good. Developing and sharing a strong point of view isn't a nice-to-have; it's a moral obligation for leaders in this space.

Episode Highlights: 

[00:01:00] The hesitancy Eric keeps seeing in leaders who won't go public with their thinking 
[00:04:00] Defining "point of view" as a pattern of lived experience, not ex...

There's an unspoken rule in the social impact sector: we tell the truth, we follow the science, we play fair. But those rules are increasingly a losing strategy, because the industries we're up against don't have to win the argument. They just have to muddy it. Joelle Lester, Executive Director of the Public Health Law Center, has spent 25 years studying how Big Tobacco manufactured doubt, and how that same playbook now drives opposition to progress on climate, food, and public health.

Episode Highlights: 

[00:04:00] Merchants of doubt: how the tobacco industry wrote the playbook f...

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

This episode explores the spectrum between "brandmaxxing" and "debranding," two extremes that reveal something important about how the sector thinks about visibility. The social impact sector has been structurally imbalanced toward the debranding end for decades, and the reluctance to invest in brand often masquerades as virtue. But...

Every major technological paradigm shift has broken society before it fixed it. The printing press, radio, television. Each one reshaped how we communicate and what we believe. Now the internet, social media, and AI are repeating the pattern at unprecedented speed. Joel Breakstone, co-founder and executive director of the Digital Inquiry Group, has spent over a decade studying how people evaluate online information, and what he's found is alarming: students, academics, and everyday adults are failing at even the most basic tasks of digital discernment. But his research also reveals a path forward, built on the surprisingly simple strategies...

There's a quiet belief running through the social impact space that being too visible somehow cheapens the work. That good organizations should let their impact speak for itself. But the orgs that get the funding, the talent, and the momentum aren't always the ones doing the best work; they're the ones who've made their work visible. This episode makes the case that visibility matters more than impact, and that staying humble is a belief most orgs can no longer afford.

Episode Highlights:

[00:00:00] Visible orgs outperform high-impact orgs 
[00:02:30] The humility trap and the "s...

The social impact sector has made community co-creation almost sacred. Design with people, not for them. Give everyone a voice. But what happens when the loudest voices aren't the most informed, and the planning process stalls because nobody can make a call? Taylor Stuckert, CEO of Lead for America, has lived this tension from every angle. Eric and Taylor dig into the question nobody in social impact wants to ask out loud: can too much community input actually be a problem?

Episode Highlights:

[00:01:30] Wilmington, Ohio and the...

Most nonprofit leaders have been through some version of the brand strategy process. Eric calls it process theater: brand strategy work that sounds great in proposals but leaves everyone wondering what they're actually building toward. This episode puts ten common elements of brand strategy on trial.

Eric and Jonathan each rank them as essential, important, or overrated, and the results surface a real philosophical divide. Where they genuinely disagree is on brand values, and the tension reveals the gap between how brand strategy is supposed to work and how it actually plays out. 

Episode H...