Break Fake Rules: Change Big Giving For Good

What happens when one of the most dreaded days on the calendar gets reimagined as a celebration of collective care? In this episode, Stupski Foundation CEO Glen Galaich and co-host Jamie Allison, executive director of the Walter and Elise Haas Fund, use Tax Day to open up a bigger conversation about public responsibility, private wealth, and what taxes make possible. Jamie makes a joyful case for loving Tax Day, not in spite of what it asks of us, but because taxes fund the schools, roads, clean water, and public systems that hold our lives together. Together, she and Glen ask what it would mean to stop treating taxes as something to avoid and start seeing them as an investment in one another, while also asking whether philanthropy is putting its own tax-advantaged dollars to work with that same sense of responsibility.
They are joined by Elizabeth Cushing, CEO of Playworks, a national nonprofit that helps nearly 1 million children each year build belonging, resolve conflict, and return to class ready to learn through structured play and recess. Elizabeth lays out the damaging impact of federal education funding cuts and tightening state budgets on kids across the country. She reframes the question of “how can philanthropy possibly backfill federal funding cuts” to “how can philanthropy act as a bridge in this moment to help nonprofits survive the next few hard years instead of forcing nonprofits to go it alone?”
💡Elizabeth Cushing: I'm hopeful that the midterms put some folks in Congress that prioritize children's well being, and I don't care which side of the aisle they're on, that is what our country is responsible for.
Learn more about Playworks and how they help kids build belonging, resolve conflict, and experience the power of play every day.
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: Elizabeth Cushing | Playworks
Executive Producer: Claire Callahan
Production Team: Podfly
Graphic Design: Middle MGMT

What happens when we stop designing philanthropy around preservation, control, and donor comfort, and start asking how to put more capital, trust, and collective action to work? In this episode, Glen Galaich speaks with Renee Kaplan, CEO of Forward Global, in a conversation recorded at the Forward Global Summit in Whistler. They challenge the fake rules that keep philanthropy cautious and exclusive, and explore what opens up when wealth holders, nonprofit leaders, entrepreneurs, and other changemakers come together to solve problems side by side.
Renee shares how Forward Global has evolved into a global community and impact platform built to amplify what works, accelerate collective action, and move resources at the pace this moment demands. If you’re ready to replace judgment and rigid boundaries with trust, openness, and a shared belief that no single person can drive lasting change alone, this episode is for you.
💡Renee Kaplan: Are you ready to deploy, or are you only into preservation?
Learn more about Forward Global and how you can join their global community.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.
Learn about the Stupski Foundation.

Guest: Renee Kaplan | Forward Global
Executive Producer: Claire Callahan
Visual Production Team: SeeBoundless
Production Team: Podfly
Graphic Design: Middle MGMT

What happens when we stop chasing individual freedom and start asking what it would mean to be free together? In this episode, Stupski Foundation CEO Glen Galaich sits down with Mia Birdsong, founder and executive director of Next River, where she is creating the cultural conditions necessary for a truly free world to emerge. Together, they break the fake rules of individualism, redefine what freedom actually is, and explore how we might pivot from a society organized around separation and scarcity to one rooted in care, connection, and collective well being.
💡Mia Birdsong: I understand the kind of fear and anxiety that has us wanting to grip tightly to what's familiar, because it feels safe, but it's not safe. It's never been safe.
💡Mia Birdsong: If we can find the courage to let go of trying to hold on to this thing, trying to fix this thing, and trust that together, if we are oriented toward our collective care and well being, we can build something better.
Learn more about Next River and their work to create the cultural conditions for a truly free world to emerge.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.
Learn about the Stupski Foundation.

Guest: Mia Birdsong | How We Show Up
Executive Producer: Claire Callahan
Production Team: Podfly

Graphic Design: Middle MGMT

We’re excited to share a special feed swap this week from our friends, Eric Brown and Kirk Brown, on the Let’s Hear It podcast! In this episode, you’ll get to hear directly from Glen Galaich and frequent Break Fake Rules co-host and Let’s Hear It host, Eric Brown, as they talk about Glen’s newly released book, CONTROL: Why Big Giving Falls Short.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Join Glen on the book tour!
CONTROL: Why Big Giving Falls Short, out now, makes an argument as simple as it is explosive: when a donor takes a tax deduction to give money away, they've made a deal with the public. That money isn't theirs anymore. But the system we've built lets donors park billions in foundations and donor-advised funds indefinitely — dribbling out 5 cents on the dollar while the rest sits on Wall Street going absolutely nowhere.
Glen isn't an outside critic. He's a sitting foundation CEO who spent years reinforcing every rule he's now trying to break. Eric read an early draft, argued with him about it, and told him his central framing was too polite. Glen ignored him. They pick up that conversation here.
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Learn about the Stupski Foundation and Glen Galaich.

This week, the co-hosts of Break Fake Rules are taking control of the show to talk behind Glen Galaich’s back about his new book, CONTROL: Why Big Giving Falls Short, out today!
Eric Brown, principal of Brown Bridge Strategies and co-host of Let’s Hear It, locks Glen out of the Break Fake Rules studio to bring you a conversation with all of your favorite co-hosts: Jamie Allison, executive director of the Walter and Elise Haas Fund; Ralph Lewin, executive director of the Peter E. Haas Jr. Family Fund; and Dr. Carmen Rojas, president and CEO of the Marguerite Casey Foundation.
Together, they dig into the book— what resonated, where they differed, and what it made them reconsider in their own work. What starts as a conversation about CONTROL opens into something larger: a candid conversation about leadership, power, accountability, and what philanthropy owes the communities it claims to serve. They also make a compelling case for why CONTROL is worth reading. Not because it offers easy agreement, but because it forces harder questions to the surface so we can change Big Giving for good.
💡Jamie Allison: I think what's more important is breaking the fake rule that proximity to resource, proximity to wealth, equals wisdom…wealth does not necessarily equal wisdom.
💡Jamie Allison: I think Control is worth reading because it invites philanthropy to look honestly in the mirror and ask whether our systems are truly serving the communities that we say that they're meant to.
💡Carmen Rojas: I think we need a different operating model and control offers us a different pathway to operate as a society in response to these current crises.
💡Ralph Lewin: The fake rule that stuck out to me from this book is that we spend all our time on 5% of our resources, when 95% of our resources is not necessarily mission aligned.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short. Join Glen on the book tour!
Learn about the Stupski Foundation.
Co Hosts: Eric Brown, Jamie Allison, Carmen Rojas & Ralph Lewin
Executive Producer: Claire Callahan
Production Team: Podfly