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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
  • Rewriting Foundation Board Rules feat. Carol Cheney & Katie Carter
    Oct 28 2026
    What if a foundation board’s most important exercise of power is knowing when to share it? In this live crossover episode with the Can we talk about…? podcast filmed at Philanthropy Northwest’s conference, co-hosts Mares Asfaha, Associate Director of Programs at Philanthropy Northwest, and Glen Galaich, CEO of the Stupski Foundation, are joined by Carol Cheney, CEO of The Collins Foundation, and Katie Carter, CEO of Pride Foundation, to challenge long-held assumptions about board authority and accountability. Together, they explore how inherited governance practices can shape whose voices are heard, whose priorities prevail, and who ultimately gets to make decisions that affect communities.Their experiences reveal that fake board rules often hold our sector back from realizing lasting change. Together, they question where power resides, how to build trust across an organization, and reconsider what it means to honor a legacy. From fiduciary responsibility to perpetuity, they challenge a fundamental assumption in philanthropy: that accountability requires control.This episode is also available on Can we talk about...?'s feed. Listen to more conversations about equity-centered philanthropy and subscribe here.💡 Katie Carter: “It turns out that the best role for the board was not deeply reviewing all of these grants, making that whole process take a whole lot longer and making it harder for us to get resources out to community.”💡 Carol Cheney: “The big question is, what is a legacy, and really examining what that really means for different people. And you know, a legacy can happen today. We can make a legacy happen right now.”💡 Mares Asfaha: “And maybe this is another fake rule we talk about. It's either 5% or perpetuity. There are so many numbers between five and 100.”💡 Glen Galaich: “This system has been built very much on centering donors and what donors need, much more than it's built on focusing on what communities need.”Explore Philanthropy Northwest and its work over 50 years to shift resources and power toward underinvested communities across the Northwest and beyond. Check out the Mentimeter results to see which foundation board rules audience members are ready to challenge.Visit The Collins Foundation to learn more about its work rethinking legacy, equity, and how a family foundation can respond to the needs of communities today.Explore Pride Foundation and its approach to putting decision-making power closer to the people and strategies shaping the work.Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Learn about the Stupski Foundation.Co-Hosts: Mares Asfaha & Glen GalaichGuests: Carol Cheney & Katie CarterExecutive Producers: Claire Callahan, Aya Tsuruta & Emily DamanProduction Team: SeeBoundless & Podfly Graphic Design: Middle MGMT
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    31 mins
  • If You Want Nonprofits to Win, Fund the People Who Make It Possible feat. Jennifer Haas
    Oct 21 2026

    What becomes possible when philanthropy invests in the well-being of the people doing the work? In this episode, co-hosts Jamie Allison, Executive Director of the Walter & Elise Haas Fund, and Glen Galaich sit down with Jennifer Haas, President of the Levi Strauss Foundation and founder of the Women’s Leadership and Wellbeing Award, to examine the connection between philanthropic impact and nonprofit worker wellness.

    Jennifer’s own experiment offers a different model. Through the Women’s Leadership and Wellbeing Award, women social justice leaders receive $15,000 tax-free personal checks with no proposal, reporting requirement, or prescribed definition of what well-being should look like. That choice opens a much larger conversation about trust, proximity, and philanthropy’s attachment to control. The question running through the episode is deceptively simple: if philanthropy is serious about helping organizations win, are its own practices designed to make that possible?

    💡 Jennifer Haas: “You're almost throwing money away if you give a grant to an organization and you don't consider the well-being of the staff and the team.”

    💡 Jamie Allison: “You can't contribute toward building a healthy community through unhealthy organizations. If the people inside of an organization are not doing well, that's going to take away from the community impact.”

    Learn more about Jennifer Haas and the Women’s Leadership and Wellbeing Award through the Levi Strauss Foundation.

    Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.

    Learn about the Stupski Foundation.

    Co-Hosts: Jamie Allison & Glen Galaich

    Guest: Jennifer Haas

    Executive Producer: Claire Callahan

    Production Team: Podfly

    Video Editing: Edith Belmont

    Graphic Design: Middle MGMT

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    30 mins
  • What If the Best Leadership Move Is Knowing When To Leave? feat. Kate Levin Markel
    Oct 14 2026

    How long is too long to lead a foundation? In this episode, Glen sits down with Kate Levin Markel, President of the McGregor Fund, to break a fake rule philanthropy rarely talks about: once foundation leaders get the job, there is very little incentive for them to leave. Kate explains why she made herself a promise to step aside after roughly a decade. As she demonstrates, staying too long can lead to stagnation and disconnection from community, while new leadership can expand our view of what is possible.

    Kate also shares how McGregor responded when its grant partners faced an increasingly uncertain political environment by doubling their payout from roughly 5% to 10%. For Kate, both decisions come back to the same question: are foundations willing to evolve when the communities they serve need something different from them?

    💡Kate Levin Markel: “I think the longer many of us are in these roles, the more disconnected we become from the community we are serving.”

    Learn about the McGregor Fund and how it is evolving its grantmaking and leadership to stay responsive to the communities it serves.

    Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.

    Learn about the Stupski Foundation.

    Hosts: Glen Galaich

    Guest: Kate Levin Markel

    Executive Producer: Claire Callahan

    Production Team: Podfly

    Video Editing: Edith Belmont

    Graphic Design: Middle MGMT

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    24 mins
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