Break Fake Rules: Change Big Giving For Good

Stupski Foundation
  • 4.6 (12)
  • Non-Profit
  • Updated Monthly

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.

  1. 22h ago

    The Fight Is Generational. The Funding Should Be Too. feat. Emily Lee

    What could we change if we broke out of boom-and-bust election-cycle funding to support long-term generational transformation? In this episode, Glen and co-host Ari Datta, Stupski Foundation’s Food Justice Program Manager, sit down with Emily Lee, executive director and co-founder of Seed the Vote Action, for a conversation about voter organizing, political power, and the fake rules that keep philanthropy funding too little, too late. Emily has dedicated her career to grassroots organizing, multiracial coalition building, and growing people-powered political movements. Through Seed the Vote Action, she mobilizes volunteers in battleground states while building lasting political power in working-class communities and communities of color. Emily challenges funders to move beyond short-term grant cycles and invest in the relationships, organizing, and risk-taking required to meet this moment. At the heart of the conversation is a clear call to philanthropy: stop funding like this is a two-year fight, and start funding like democracy depends on what we build for generations. 💡Ari Datta: “Get really clear on what fake rules you're operating with, and those will be rules set by your board, by internal culture, by your mindset or your belief system, and get really clear on what the real rules are.” 💡Emily Lee: “Don't fund for the grant cycle, fund for the generational fight.” Learn more about Seed the Vote and support its work to build people-powered movements through voter organizing, deep canvassing, and long-term community power. Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation. Co-Hosts: Ari Datta & Glen Galaich Guest: Emily Lee Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    The Fight Is Generational. The Funding Should Be Too. feat. Emily Lee

  2. Jul 22

    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 Galaich Guest: Santhosh Ramdoss Executive Producer: Claire Callahan Production Team: Podfly & Gary Community Ventures Video Editing: Edith Belmont Graphic Design: Middle MGMT

    Is The Future of Philanthropy Impermanence? feat. Santhosh Ramdoss

  3. Jul 8

    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 Galaich Guest: Gara LaMarche Executive Producer: Claire Callahan Production Team: Podfly Video Editor: Edith Belmont Graphic Design: Middle MGMT

    Philanthropy Needs Its Critics feat. Gara LaMarche

  4. Jun 17

    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 Consuegra Guest: Aria Florant Executive Producer: Claire Callahan Production Team: Podfly Video Editing: Edith Belmont Graphic Design: Middle MGMT

    What If America’s 250th Becomes a Turning Point for Repair? feat. Aria Florant

  5. Jun 3

    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 Galaich Guest: Vu Le Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    Can Funders Beat Thanos Without Engaging in Politics? feat. Vu Le

  6. May 27

    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 Galaich Guest: Trabian Shorters Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    Asset-Framing to End Philanthropy's Savior Complex feat. Trabian Shorters

  7. May 20

    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 Threats Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation. Co-Hosts: Eric Brown & Glen Galaich Guest: Elisha Smith Arrillaga, Ph.D. Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    New Data Highlights Reality Gap Between Nonprofits & Funders feat. Elisha Smith Arrillaga

  8. May 13

    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 Galaich Guest: Nwamaka Agbo | Kataly Foundation Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    The F Word Philanthropy Avoids Is the One It Needs Most feat. Nwamaka Agbo
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4.6
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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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