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Break Fake Rules: Change Big Giving For Good: Daily Summaries Delivered
by Stupski Foundation
Some rules are meant to be broken—especially the fake ones! Break Fake Rules is a podcast that brings today’s news and big philanthropic issues into focus, challenging the self-imposed rules that shape the flow of money, power, and resources in America. Join Glen Galaich, CEO of the Stupski Foundation, and a rotating cast of co-hosts as they unpack the news of the day and engage in conversations with principled rulebreakers in philanthropy, nonprofits, government, media, and more. Each episode examines the fake rules holding the systems in place that don’t serve us—and which rules we must break to secure a better future for all. If you have ever questioned why we live by certain rules and wondered what becomes possible when we do things differently, this show is for you.
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- 1 weeks ago24 min
Is The Future of Philanthropy Impermanence? feat. Santhosh Ramdoss
What changes when we embrace impermanence instead of trying to live forever? In this episode, Glen Galaich sits down with Santhosh Ramdoss, president and CEO of Gary Community Ventures, for a conversation about impermanence and legacy. Guided by Gary’s commitment to move all its assets into the community by 2035, Santhosh debunks the fake rule that philanthropic impact depends on institutional permanence. He invites the sector to imagine a legacy rooted in stronger systems, durable public funding, and the beauty, love, and care we leave behind. In a Break Fake Rules exclusive, Santhosh rolls out a new game, The Philanthropy Challenge, that funders can play to respond to urgent crises and see where philanthropic funds can have the greatest impact. At the heart of the conversation is a more expansive question for wealth holders and foundation leaders: what if ending an institution is not a loss, but a strategic opening? And what becomes possible when philanthropy brings more joy, wonder, and imagination into the work of building a world that can outlast any one foundation?💡Santhoush Ramdoss: “I think one of the practices that philanthropy does need a lot more of is joy and wonder. I think we've lost our capacity to see what's possible, and sometimes the moment of being in that wondrous possibility of what systems could be is lost.” Learn more about Gary Community Ventures and play The Philanthropy Challenge for yourself! Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation.Host: Glen GalaichGuest: Santhosh Ramdoss Executive Producer: Claire CallahanProduction Team: Podfly & Gary Community VenturesVideo Editing: Edith BelmontGraphic Design: Middle MGMT
- 3 weeks ago31 min
Philanthropy Needs Its Critics feat. Gara LaMarche
What happens when philanthropy’s sharpest critique comes from inside the sector itself? In this episode, Stupski Foundation CEO Glen Galaich and co-host Eric Brown sit down with Gara LaMarche - longtime philanthropic leader, democracy advocate, and one of the OG fake rule breakers. Gara worked with George Soros at Open Society Institute, and Chuck Feeney at The Atlantic Philanthropies, and famously served as the “prosecutor” where he put philanthropy on trial in a 2011 mock trial before thousands of foundation leaders.Gara takes on the fake rule that people inside philanthropy are not supposed to criticize it, arguing that philanthropy should release its obsession with ego and that foundations should treat their resources as a public trust. Along the way, he digs into investing in power building, questions philanthropy’s instinct to be overly cautious, and calls on foundation leaders to use their influence to support communities, even when it’s uncomfortable or inconvenient.💡 Gara LaMarche: If you can't speak out about authoritarianism or attacks on the very communities that you're purporting to protect, if not now, when?Learn more about Gara LaMarche and his work advancing philanthropy, democracy, human rights, and social justice. Watch Gara put philanthropy on trial.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Co-Hosts: Eric Brown & Glen GalaichGuest: Gara LaMarche Executive Producer: Claire CallahanProduction Team: PodflyVideo Editor: Edith BelmontGraphic Design: Middle MGMT
- Jun 17, 202630 min
What If America’s 250th Becomes a Turning Point for Repair? feat. Aria Florant
Fake rules tell us funding reparations is too complicated, too controversial, or too distant. So what will it take for us to see that repair is a responsibility we all carry?In this episode, Glen Galaich and co-host Malia Becton-Consuegra, Stupski Foundation’s Bay Area post-secondary success program officer (who also leads reparations work at the foundation), sit down with a visionary leader in the reparations movement, Aria Florant, co-founder and executive director of Liberation Ventures. They discuss repair, narrative power, and what it takes to build a truly multiracial democracy. As the U.S. gears up to celebrate Juneteenth and its 250th anniversary, Aria challenges the fake rule that supporting reparations is politically impossible, unprecedented, or simply too hard. Instead, she invites us to imagine a country where reparations lay the foundation for enduring generational change.Aria shares how Liberation Ventures is investing in heart-and-mind change, with a Beloved Repair campaign to move reparations from the margins to the mainstream. At the center of it all is a bold, hopeful question: What becomes possible when reparations stop feeling radical and become common sense?💡Aria Florant: “We should be contending for the hearts and minds of everyone. This is not just about Black people, and all people can and should be doing this work, and in particular, doing it in their own communities with their own people, because we know that peer-to-peer organizing is one of the most effective ways to change culture.”Learn more about Liberation Ventures’work to support Black-led efforts for repair, racial healing, and reparations. Check out their Beloved Repair campaign.Learn about the Stupski Foundation.Co-Hosts: Glen Galaich & Malia Becton ConsuegraGuest: Aria FlorantExecutive Producer: Claire CallahanProduction Team: PodflyVideo Editing: Edith BelmontGraphic Design: Middle MGMT
- Jun 3, 202625 min
Can Funders Beat Thanos Without Engaging in Politics? feat. Vu Le
There’s a dirty word philanthropy doesn’t like to talk about - politics. But does staying above the political fray actually prevent us from supporting the communities and issues we claim to care about? In this live audience episode, Glen Galaich sits down with Vu Le, author of Reimagining Nonprofits and Philanthropy and the voice behind Nonprofit AF, for a funny, urgent, and table-flipping conversation. With his signature humor and candor, Vu challenges the fake rule that serious work has to be humorless, and pushes the sector to look at what conservative funders have built, what progressive funders keep avoiding, and what it would take to actually fund the future they say they want.Together, Glen and Vu dig into the power dynamics that keep nonprofits begging for crumbs, the limits of donor-centered philanthropy, and the need to make transformative, generational investments to support our democracy today, rather than waiting for it to crumble around us. At the center of it all is Vu’s challenge: philanthropy cannot fight for democracy, equity, justice, and a livable future while staying detached from power. We must harness our imagination and give all our resources like our future depends on it. 💡Vu Le - “We say foundations are not effective, philanthropy is not effective. That's not true. Progressive-leaning philanthropy is not effective because conservative funders have been extremely effective for like four decades now, and we're still here scrambling to do stuff to catch up."Buy your copy of Vu Le’s book, Reimagining Nonprofits and Philanthropy, and read Vu’s latest musings on NonprofitAf.com.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation.Host: Glen GalaichGuest: Vu Le Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT
- May 27, 202626 min
Asset-Framing to End Philanthropy's Savior Complex feat. Trabian Shorters
Philanthropy has a mindset problem, and it’s harming the very communities it claims to support. But what if philanthropy shifted its perspectives to see people through their aspirations, contributions, and power instead of their challenges?Co-hosts Glen Galaich and Eric Brown sit down with Trabian Shorters, a leading social entrepreneur, founder of BMe Community, and developer of the award-winning cognitive framework Asset-Framing®. Together, they explore why Asset-Framing is far more than a communications strategy—and how it fundamentally shifts how the brain understands people, problems, and possibilities.Trabian challenges the fake rule that fear is the strongest motivator, making clear that fear may trigger an initial reaction, but it cannot move us toward justice, equity, or lasting change. From there, he reframes what philanthropy can become when it stops treating communities as problems to solve and starts investing in people as the protagonists of their own lives.💡Trabian Shorters: When you think about folks just based on what is wrong with them, you won't even consider the other half of their life and the types of options that are available. There's more going on in your life than what's wrong with you. So if you can understand it for yourself, then you can understand it for other people.Learn more about Trabian Shorters and his work with BMe Community, where he is helping leaders across philanthropy, journalism, and social impact change how people and communities are understood, funded, and supported.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Co-Hosts: Eric Brown & Glen GalaichGuest: Trabian Shorters Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT
- May 20, 202631 min
New Data Highlights Reality Gap Between Nonprofits & Funders feat. Elisha Smith Arrillaga
Nonprofit leaders are ringing alarm bells, but foundations are still deciding whether this moment is different enough to act. In this episode, Stupski Foundation CEO, Glen Galaich, and co-host Eric Brown sit down with Elisha Smith Arrillaga, Ph.D., vice president of research at the Center for Effective Philanthropy, to discuss what CEP’s recent research reveals about the widening gap between how foundations think they are showing up and how nonprofits are experiencing this moment.Together, they dig into the findings in CEP’s latest report, State of Nonprofits 2026, including rising deficits, CEO burnout, possible mergers, foundation caution, and the risks facing the people who rely on nonprofit services. Elisha challenges one of philanthropy’s most familiar fake rules: that every urgent problem needs a long strategy process before funders can take action. Sometimes the data is already clear. Sometimes the need is immediate. And sometimes the bridge from foundation thinking to nonprofit reality is not another plan, but the courage to move resources now.💡Elisha Smith Arrillaga: I believe the most important fake rule to break is that we need a strategy to solve every problem...sometimes we get caught up in the need to have a plan. Sometimes it doesn't necessarily require a plan, but requires some action.Learn more about The Center for Effective Philanthropy and its research, including the State of Nonprofits 2026 and A Sector in Crisis: How U.S. Nonprofits and Foundations Are Responding to ThreatsOrder your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Co-Hosts: Eric Brown & Glen GalaichGuest: Elisha Smith Arrillaga, Ph.D. Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT
- May 13, 202626 min
The F Word Philanthropy Avoids Is the One It Needs Most feat. Nwamaka Agbo
What will it take for us to stop treating failure like a private embarrassment and start seeing it as a way to learn, grow, and take better risks? In this episode, Stupski Foundation CEO Glen Galaich sits down with Nwamaka Agbo, CEO of the Kataly Foundation, for a candid conversation about the fake rules that keep philanthropy playing it safe when communities need funders to move with more courage.Together, Glen and Nwamaka explore philanthropy’s complicated relationship with the F word: failure. Nwamaka makes the case that failure is already happening across the sector, but when foundations fail in secret, they miss the chance to learn and help others avoid the same mistakes. She also pushes philanthropy to think beyond what feels legally convenient and toward what is morally necessary in this moment, including moving capital beyond traditional 501(c)(3) structures. The conversation invites funders to lower the wall between investment and grantmaking, question their own risk tolerance, and consider what becomes possible when failure is treated not as a source of shame but as a powerful tool for change.💡Nwamaka Agbo: If you run a really good experiment, chances are every once in a while that experiment is going to fail, and the failure actually gives you more information, more indication for how to improve your work going forward. And so if we can share our failures with our colleagues in philanthropy, more widely, more broadly, then all of us don't have to fail as frequently, and we don't have to fail alone.Learn more about the Kataly Foundation and how they are challenging philanthropy to move capital with greater accountability, transparency, and courage.Check out their failure series.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Host: Glen GalaichGuest: Nwamaka Agbo | Kataly Foundation Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT
- May 6, 202633 min
When We Invest in Women, We Transform Democracy for Generations feat. Jennifer Siebel Newsom & Dr. Kimberlé Crenshaw
What happens when philanthropy stops treating women and girls as a side issue and starts seeing them as a powerful lens through which we can better understand the major fights for justice, democracy, safety, and human dignity? In this live episode, recorded at The Giving List Women “Doing It Differently” Summit in Santa Barbara, Glen Galaich, CEO of the Stupski Foundation, and co-host Gwyn Lurie, Co-Founder and CEO of The Giving List Women, sit down with two leaders who have spent their careers challenging the stories, systems, and assumptions that shape our society: Jennifer Siebel Newsom, First Partner of California and award-winning documentary filmmaker behind Miss Representation and the new documentary Miss Representation: Rise Up, and Dr. Kimberlé Crenshaw, professor of law at UCLA and Columbia Law School, co-founder and executive director of the African American Policy Forum, host of Intersectionality Matters!, and author of the new book Backtalker.Together, they take on one of the most dangerous fake rules in philanthropy and culture— the idea that women and girls are a “lane” instead of a lens for understanding the defining issues of our time. Drawing on law, media, narrative, movements, and lived experience, they call out the short‑sighted practice of measuring impact in one‑ or two‑year cycles while anti‑democratic backlashes are funded for generations, and challenge funders to abandon outdated frameworks. They make clear that investing in women’s health, safety, financial security, and leadership is central to building a healthier democracy and a more just future. 💡Dr. Kimberlé Crenshaw: The old frameworks that we've used to determine how to spend money, where to invest. We've got to throw that out. We’ve got to look at what this war is right now, and it's very, very different from the way we typically think about it. 💡 Jennifer Siebel Newsom: “When we center women, when we invest in women's health, their safety, their financial security, women will be the most transformative leaders in world history.” Learn more about The Giving List Women, created to inspire donors, leaders, and changemakers to apply the lens of women and girls to philanthropic and other forms of investment, and to build partnerships that fuel a more gender-balanced world. Order your copy of Dr. Kimberlé Crenshaw’s book, Backtalker.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation.Co-Hosts: Gwyn Lurie & Glen GalaichGuests:Jennifer Siebel Newsom - The Representation Project | Miss Representation: Rise Up Dr. Kimberlé W. Crenshaw- Backtalker | Intersectionality Matters! Executive Producer: Claire CallahanVideo Production Team: SeeBoundlessAudio Production Team: PodflyGraphic Design: Middle MGMT
About Break Fake Rules: Change Big Giving For Good
Some rules are meant to be broken—especially the fake ones! Break Fake Rules is a podcast that brings today’s news and big philanthropic issues into focus, challenging the self-imposed rules that shape the flow of money, power, and resources in America. Join Glen Galaich, CEO of the Stupski Foundation, and a rotating cast of co-hosts as they unpack the news of the day and engage in conversations with principled rulebreakers in philanthropy, nonprofits, government, media, and more. Each episode examines the fake rules holding the systems in place that don’t serve us—and which rules we must break to secure a better future for all. If you have ever questioned why we live by certain rules and wondered what becomes possible when we do things differently, this show is for you.
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