Break Fake Rules: Change Big Giving For Good

Stupski Foundation
  • 4.6 (10)
  • 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. You Can’t Fight Autocracy by the Spoonful with Ralph Lewin feat. Skye Perryman

    1D AGO

    You Can’t Fight Autocracy by the Spoonful with Ralph Lewin feat. Skye Perryman

    This is philanthropy’s rainy day. Across communities, the escalation of ICE activity is terrifying. Families are living in fear. Core pillars of our democracy are under attack. Meanwhile, too many funders are still holding back, waiting for a crisis that’s already here. In this episode, Glen and Ralph Lewin weigh in on why escalating ICE actions should be a wake-up call for philanthropy to step up in real ways to protect our communities. They challenge the persistent myth that philanthropy must conserve resources for a future emergency. Spoiler alert: this is the emergency. Special guest, Skye Perryman, President and CEO of Democracy Forward, joins the conversation to share how ongoing litigation is actively defending our democracy. Skye brings both urgency and hope—reminding us that, despite efforts to flood the zone, the people are winning more than they’re losing. But we will only win if philanthropy fully funds the legal, advocacy, and organizing efforts that make those wins possible. 💡 Skye Perryman: The cost of inaction in this moment is far higher than the cost of taking action. Learn more about Democracy Forward and their initiative, Democracy 250, and find out how you can support the work of defending democracy Preorder your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation. Co-Hosts: Ralph Lewin & Glen Galaich Guest: Skye Perryman Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    27 min
  2. Risk Isn’t Irresponsible, It’s Required with Ralph Lewin Feat. María Teresa Kumar

    FEB 4

    Risk Isn’t Irresponsible, It’s Required with Ralph Lewin Feat. María Teresa Kumar

    Why does philanthropy resist risk? Ralph Lewin, Executive Director of the Peter E. Haas Jr. Family Fund, joins Glen as co-host to bust one of the biggest fake rules in philanthropy. In this episode, Ralph and Glen make the case for embracing “philanthropic reformers” (not critics!) and courageous risk-taking rather than clinging to a comfortable but broken status quo. Special guest, María Teresa Kumar, Emmy-nominated MSNBC contributor and founding president and CEO of Voto Latino, stops by to reflect on what it really means to be “American” in today’s political climate. As fear-driven narratives and ICE raids targeting immigrants intensify ahead of the midterms, María Teresa reminds us why reengaging and delivering on promises made to the Latino electorate has never been more urgent. 💡 María Teresa Kumar: “Recognize that no is for everybody else. Everybody will say no to you. And that's okay, because you only need one yes.” Get involved with Voto Latino. Break Fake Rules is a podcast that brings today’s news and big philanthropic issues into focus to change Big Giving for good. Learn about the Stupski Foundation. Co-Hosts: Ralph Lewin & Glen Galaich Guest: María Teresa Kumar Executive Producer: Claire Callahan Production Team: Podfly Graphic Design: Middle MGMT

    28 min
  3. Go Hard or Go Home with Jamie Allison feat. Representative Lateefah Simon

    JAN 28

    Go Hard or Go Home with Jamie Allison feat. Representative Lateefah Simon

    Welcome back to Break Fake Rules! In the season three premiere, Jamie Allison, Executive Director of the Walter and Elise Haas Fund, co-hosts with Glen Galaich to discuss the fake rules we need to break to relieve the pressure nonprofits are under at the outset of 2026. Special guest, Representative Lateefah Simon (CA-12), joins from Capitol Hill to reflect on her journey from nonprofit leader to federal policymaker. At a moment of intensifying fear and political division, Representative Simon calls on us to reject division, protect nonprofits, and do more for our communities. 💡Representative Lateefah Simon: “If we’re not going to go hard, we should go home.” Tune in for a candid conversation about breaking through partisan divides and making real change in our communities. Learn about Representative Lateefah Simon’s work and subscribe to her newsletter. Break Fake Rules is a podcast that brings today’s news and big philanthropic issues into focus to change Big Giving for good. Learn more about the Walter and Elise Haas Fund. Learn about the Stupski Foundation. Co-Hosts: Jamie Allison & Glen Galaich Guest: Representative Lateefah Simon Executive Producer: Claire Callahan Production Team: Podfly

    30 min
  4. Break Fake Rules Returns - Season 3 Trailer

    JAN 21

    Break Fake Rules Returns - Season 3 Trailer

    Break Fake Rules is back! Join us for a new season of rulebreaking to change the future of Big Giving for good. Get ready for more episodes, more often! This season, we're excited to welcome a few of our favorite rule breakers as recurring co-hosts. Alongside Glen Galaich, CEO of the Stupski Foundation, they will call on us to rethink the stories we tell about money, wealth, and power—and imagine a future where resources are shared, not hoarded. 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. New episodes drop weekly starting January 28, 2026.

    2 min
  5. BONUS EPISODE: Season 2 Roundup

    12/10/2025

    BONUS EPISODE: Season 2 Roundup

    That’s a wrap on season 2! In this bonus episode of Break Fake Rules, hear some of Glen and Claire’s favorite moments from the season. And spoiler alert - they drop exciting updates about what’s coming next season on Break Fake Rules.  Break Fake Rules is a podcast from the Stupski Foundation that questions philanthropy’s self-imposed rules and looks for ways philanthropy can better serve communities and contribute to lasting change.  Learn about the Stupski Foundation’s work. Host: Glen Galaich Guest & Producer: Claire Callahan

    37 min
  6. Where Do We Go From Here? with Jamie Allison and Carmen Rojas

    12/09/2025

    Where Do We Go From Here? with Jamie Allison and Carmen Rojas

    In the season wrap of Break Fake Rules, Carmen Rojas (CEO & President, Marguerite Casey Foundation) and Jamie Allison (Executive Director, Walter & Elise Haas Fund) bring the vibes to a year-defining conversation with host Glen Galaich. Together, they reflect on how philanthropy showed up in 2025—and how it needs to evolve in 2026. Jamie Allison calls on the sector to embrace courage and purpose: “Our communities and nonprofit leaders need from us what they've always needed from us. They need us to be courageous and to show that the project of philanthropy is about redistributing privilege and resources.” Carmen Rojas offers a bold vision for the road ahead, challenging philanthropy to think generationally and confront its own complicity: “We have an opportunity… to reset that table.” And: “We need to reconcile and have a meaningful conversation about the ways each of our institutions is enabling… this political movement.” Looking ahead at 2026, Glen Galaich reminds us why imagination matters: “So many foundations limit themselves to a cap… It stops us from dreaming and imagining things that could be leveraged for a better society.” Tune in for a finale filled with the kind of rule-breaking energy that sets the stage for a transformative 2026. Learn more about the Walter and Elise Haas Fund and the We Initiative to cultivate belonging.  Explore the Marguerite Casey Foundation and learn about their decision to significantly increase grantmaking to protect communities under attack. Break Fake Rules is a podcast from the Stupski Foundation that questions philanthropy’s self-imposed rules and looks for ways philanthropy can better serve communities and contribute to lasting change.  Learn about the Stupski Foundation’s work. Host: Glen Galaich Guests: Jamie Allison & Carmen Rojas Producer: Claire Callahan

    44 min
  7. Winning Back the Working Class with Joan C. Williams

    11/05/2025

    Winning Back the Working Class with Joan C. Williams

    Progressives have lost sight of a central issue: class. Lawyer, professor, and author Joan C. Williams joins Break Fake Rules to unpack how the Left lost touch with working-class Americans—and how we can win them back. As income inequality deepens across the U.S. and Europe, Joan explains how class blind spots and broken promises have fueled distrust and driven voters toward the far right. Joan offers actionable, research-backed steps for funders and policymakers to rebuild trust, restore credibility, and reconnect with the working class. Joan C. Williams: “Not only have we been class clueless, we've often been class condescending.” Read Joan’s book, Outclassed: How the Left Lost the Working Class and How to Win Them Back. Break Fake Rules is a podcast from the Stupski Foundation that questions philanthropy’s self-imposed rules and looks for ways philanthropy can better serve communities and contribute to lasting change.  Learn about the Stupski Foundation’s work. Host: Glen Galaich Guest: Joan C. Williams Producer: Claire Callahan

    32 min
  8. Fund Like You Want to Win with Ludovic Blain

    10/15/2025

    Fund Like You Want to Win with Ludovic Blain

    “It's only when you show your own courage that the performativeness of being inspired by others moves to allied-ness.” Ludovic Blain returns to Break Fake Rules, this time at a live recording at California Donor Table’s 20th anniversary convening and celebration! Last season, Ludovic delivered a master class in philanthropic giving across tax statuses. Now he’s back to urge us to play offense — by funding bold, long-term investments to counter the well-coordinated efforts of conservative groups and donors that harm our communities. How can donors fund initiatives that not only defend democracy but also create a better government for all? What lessons can we take from local-level wins to build progressive power at the national level? Tune in to find out.  Break Fake Rules is a podcast from the Stupski Foundation that questions philanthropy’s self-imposed rules and looks for ways philanthropy can better serve communities and contribute to lasting change.  Learn more about the California Donor Table. Learn about the Stupski Foundation’s work. Host: Glen Galaich Guest: Ludovic Blain Producer: Claire Callahan Mentioned in this episode: Designing Tomorrow Podcast Check out another social impact podcast called Designing Tomorrow. It’s hosted by Eric Ressler — founder of the creative agency Cosmic — and Jonathan Hicken, executive director at the Seymour Marine Discovery Center. If you’re looking for a show that’s real, smart, and made for this moment in social impact — give Designing Tomorrow a listen. You can find it wherever you get your podcasts.

    39 min
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4.6
out of 5
10 Ratings

About

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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