Break Fake Rules: Change Big Giving For Good

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 GalaichGuest: Vu Le Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT

What happens when we stop pretending that systems will fix themselves, and ask what it really takes to change them? In this episode, Stupski Foundation CEO Glen Galaich and returning co-host Jamie Allison, Executive Director of the Walter and Elise Haas Fund, first discuss the Endeavor Fund and what it means to back organizations with long-term, trust-based support. Then they sit down with guest Catherine Bracy, founder and CEO of TechEquity and author of World Eaters: How Venture Capital Is Cannibalizing the Economy, to examine how venture capital shapes our everyday lives.Catherine traces how venture capital shifted from funding innovation to driving financialization, and why wealth inequality functions as a strategy as much as an outcome. She breaks down the power law logic that underwrites the entire system, what it extracts from workers and communities, and why it matters when foundations are more invested in venture than the organizations doing the work on the ground. The conversation lands on a challenge that’s hard to ignore: if philanthropy wants different outcomes, it has to question the assumptions behind where its money is parked, and prioritize community benefit over donor comfort.💡Catherine Bracy: The dirty little secret of venture capital is that it’s organized like a power law itself. The vast majority of these funds do not outperform the S&P 500, so what are you actually getting for that money?Learn more about TechEquity and their work to build a more equitable tech economy.Preorder your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Co-Hosts: Jamie Allison & Glen GalaichGuest: Catherine Bracy | World Eaters: How Venture Capital is Cannibalizing the Economy Executive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT

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 democracyPreorder your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.Learn about the Stupski Foundation.Co-Hosts: Ralph Lewin & Glen GalaichGuest: Skye PerrymanExecutive Producer: Claire CallahanProduction Team: PodflyGraphic Design: Middle MGMT

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 GalaichGuest: Representative Lateefah SimonExecutive Producer: Claire CallahanProduction Team: Podfly

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 GalaichGuest & Producer: Claire Callahan

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 GalaichGuest: Joan C. WilliamsProducer: Claire Callahan

Farhad Ebrahimi: “What utility is it for grantmakers to survive this political moment if none of the organizations we believe in survive?”In this episode, Farhad Ebrahimi—Philanthropic Transformation Strategist and co-founder at Solidaire Network—joins Break Fake Rules to deliver a total takedown of philanthropy’s most pernicious fake rules. And he comes with receipts! Hear why Farhad spent down the Chorus Foundation’s endowment in 2023 and what it really means to organize and mobilize funders to support a just transition to a regenerative economy that no longer feeds the philanthropic industrial compex. In a period when fear and political retribution are on the rise, Farhad calls us to prioritize grantee survival over grantmaker self-preservation. Learn about and join the Solidaire Network.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 GalaichGuest: Farhad EbrahimiProducer: Claire CallahanDesigning Tomorrow PodcastCheck 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.