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Break Fake Rules: Change Big Giving For Good

Break Fake Rules: Change Big Giving For Good

By: Stupski Foundation
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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.Copyright 2026 Stupski Foundation Economics Management Management & Leadership Political Science Politics & Government
Episodes
  • New Data Highlights Reality Gap Between Nonprofits & Funders feat. Elisha Smith Arrillaga
    May 20 2026

    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

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    31 mins
  • The F Word Philanthropy Avoids Is the One It Needs Most feat. Nwamaka Agbo
    May 13 2026

    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

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    27 mins
  • When We Invest in Women, We Transform Democracy for Generations feat. Jennifer Siebel Newsom & Dr. Kimberlé Crenshaw
    May 6 2026
    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
    Show More Show Less
    33 mins
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