Designing Tomorrow: Creative Strategies for Social Impact

What if the biggest barrier to your mission isn't funding, or talent, or market conditions — but the people sitting in your boardroom? Not because they're bad people. But because they don't have clear expectations about their role. They weren't trained on the very real skills required for governance. And they're shoved into systems that don't allow them to bring their...

What happens when organizations can't dream? Not because they lack vision. But because they're too busy scrambling to make payroll, chasing emergency grants, firefighting the latest crisis. Scarcity doesn't just drain bank accounts — it steals the capacity to imagine what's possible. In this episode, I sit down with Jamye Wooten, founder of CLLCTIVLY in Baltimore, to explore wh...

We break down the 2025 Bank of America Study of Philanthropy with the researchers who created it — exploring what this concentration means for nonprofit sustainability and the future of philanthropy.  There’s a number that keeps showing up in conversations about American philanthropy. And it tells two completely different stories depending on how you read it. Over the past decade, charitable givin...

The biggest barrier to your next stage isn’t lack of vision or resources. It’s the moment you stop imagining what could be and start protecting what already is. 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 po...

In this episode, we're joined by Drew Dumsch, President and CEO of the Ecology School at River Bend Farm in Maine. Drew co-founded the organization 26 years ago with a premise that felt radical then and feels essential now: that ecological literacy — learning to read the landscape the way you learn to read a book — is foundational to creating engaged, compassionate citizens capable of underst...

Once you see the pattern, you can't unsee it. 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 fro...

Mike Nellis has raised over $1 billion for progressive campaigns and causes. As the founder of Authentic and former Senior Advisor to Vice President Kamala Harris, he's seen what work — and what doesn't — in digital fundraising. In this conversation, we explore what nonprofits can learn from campaign strategy, the dangers of volume-driven marketing, and why authenticity might be the only...

The dominant narrative this year has been that everything’s falling apart. But what if we're manifesting a social impact doom loop? Why I have a newfound resurgence of hope and optimism for this work. 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 soc...

What if philanthropy, as we know it, is a flawed system? In this episode, we're joined by Jen Nguyen, a director at the Stupski Foundation, a unique "spend-down" organization designed to close its doors after giving away all of its assets by 2029. Jen, a former college counselor, provides an unapologetically candid look at a sector she may soon leave, revealing a rare freedom to cha...

Reflections on fear, control, and what you can actually do about it.  As we head into year-end — often the most high-stakes season in our sector — this episode will help you develop the right mindset to navigate it skillfully.  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-w...

What if everything you’ve been taught about economic progress is wrong? In this episode, Stacey Edgar — social worker turned social entrepreneur and now executive director of the International Folk Art Market — shares her journey through the “career jungle gym” of the social impact sector. We unpack her concept of artisan economics , a radically human approach to commerce rooted in care, dignity,...

How to recognize and act on the rare moments when transformation is possible. Join the conversation on substack: https://open.substack.com/pub/eressler/p/the-vision-window-is-openfor-now?r=8rkfl&utm_campaign=post&utm_medium=web&showWelcomeOnShare=true Listeners, now you can text us your comments or questions by clicking this link. *** If you liked this episode, please help spread the w...

What if real change doesn't begin with institutions, campaigns, or capital — but with the people we invite into our lives? In this episode, Eric sits down with Amanda Litman, co-founder of Run for Something and author of When We’re In Charge , to explore how small, human-scale actions can spark transformational impact — from politics to parenting to how we rebuild our social lives post-pandem...

In this episode, I’m exploring a question that’s been showing up in a lot of our recent work — and in my own thinking: What is your truth? Links: 📝 Read the full essay version on our new Substack: https://open.substack.com/pub/eressler/p/what-is-your-truth?r=8rkfl&utm_campaign=post&utm_medium=podcast&showWelcomeOnShare=true Listeners, now you can text us your comments or questions by...

Everyone loves the idea of collaboration — but real partnership? That’s harder. From mismatched visions to unclear roles, even the most well-intentioned alliances can go sideways fast. In this episode, Eric and Jonathan break down what makes partnerships work — and what to watch out for before saying yes. ➔ The five elements every partnership needs to succeed (straight from the Collective Impact f...

Too many social impact leaders step into donor meetings with a bold vision — but an unclear case for why anyone should support it. 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 framew...

We’re constantly told to “do more with less” — but what if that’s the wrong goal altogether? 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&apos...

Too many social impact organizations are stuck trying to explain everything they do — and in the process, end up saying nothing that sticks. When your mission is complex, how do you distill it into a clear, compelling story that actually resonates? In this episode, Eric and Jonathan dig into the storytelling struggles that come with multifaceted missions — and offer a practical framework to help y...

Major donor funding can feel like the holy grail of nonprofit growth — big checks, deep relationships, and potentially game-changing support. But what’s often left out of the conversation? The risk. 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 yo...

Annual reports shouldn’t feel like an obligation — they should feel like a gift. But for too many nonprofits, impact reporting is still stuck in the past: flat, uninspired, and quickly forgotten. 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 ingredie...

Social impact leaders are visionaries — but getting others to see what you see isn’t easy. When your work hasn’t caught up to your ambitions, how do you win over funders, staff, and partners who need proof before they commit? 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 —...

Nonprofit leaders know storytelling matters — but many are missing a critical opportunity to move hearts, shift narratives, and deepen support. In this episode, Eric and Jonathan pull back the curtain on why so much nonprofit content falls flat — and how a simple three-step framework can radically transform the way you communicate your mission. ➔ Why "naming the problem" is more powerful...

Not all “no’s” are equal—and if you’re in fundraising, you know that firsthand. 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...

Social impact leaders are scaling back, funding streams are evaporating, and public trust is eroding. In this candid kickoff to Season 4, Eric and Jonathan hold space for what’s really happening in the field—and why this moment demands courageous communication, community resilience, and reimagined leadership. This isn’t a time to shrink. It’s a time to show up . The surprising parallels to early C...

To wrap Season 3, Eric and Jonathan are doing something different — and a little vulnerable. 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...