Break Fake Rules: Change Big Giving For Good

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

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 Galaich

Guests:
Jennifer Siebel Newsom - The Representation Project | Miss Representation: Rise Up
Dr. Kimberlé W. Crenshaw- Backtalker | Intersectionality Matters!
Executive Producer: Claire Callahan
Video Production Team: SeeBoundless
Audio Production Team: Podfly
Graphic Design: Middle MGMT

What happens when journalism stops pretending objectivity is the same thing as truth telling? In this episode, Glen Galaich and co-host Dr. Carmen Rojas take Break Fake Rules to Kansas City for another conversation from Common Thread, the national event series from the Marguerite Casey Foundation bringing people together around the issues shaping working-class life in America. They welcome Faiz Shakir, founder of More Perfect Union, the Emmy Award-winning nonprofit newsroom redefining what news can look like when it actually centers working-class people. Together, they explore how More Perfect Union’s reporting has become a powerful tool for policy change and corporate accountability.
The conversation takes on one of the media's biggest fake rules: the myth of objectivity. Faiz makes the case for an honest form of advocacy journalism, one that stays grounded in facts while refusing to hide its investment in the lives of working people. As Glen, Carmen, and Faiz talk through the stories that much mainstream media still fails to tell, a bigger idea comes into focus: journalism can do more than describe a rigged economy. It can help people understand the forces shaping their lives, see themselves as actors in that story, and build power to change it.
💡Faiz Shakir: We used to live in an America in which earning a paycheck was the way you got wealth, and was the way you helped take care of your family. Now your labor, your W2 paychecks, are really the source of pain and angst for you, because you can't get by with that.
Learn more about More Perfect Union and how they are building power through advocacy journalism.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.
Learn about the Stupski Foundation.
Co-Hosts: Dr. Carmen Rojas & Glen Galaich

Guest: Faiz Shakir | More Perfect Union
Executive Producer: Claire Callahan
Production Team: Podfly

Graphic Design: Middle MGMT

What happens when philanthropy stops assuming young people are not ready to lead and starts trusting them when it matters most? In this episode, co-hosts Glen Galaich and Ralph Lewin, Executive Director of the Peter E. Haas Jr. Family Fund, bust open a fake rule that assumes young people do not know enough to help shape the future of our democracy. Together, they reflect on their own first experiences making grants, what philanthropy misses when it decides what is best for young people without them, and why involving youth in funding decisions can strengthen both grantmaking and democracy.
They are joined by Josh Lee, director of the Youth Power Fund, a California collaborative fund where young people do not just advise on funding decisions, they drive them. Josh makes the case for involving young people where it matters most: where resources are allocated.
💡Josh Lee: Contrary to what we might think, young people, in my opinion, are not the leaders of tomorrow. They're leading right now, today.
Learn more about Youth Power Fund and how they are working to ensure more young people, the Boldest Among Us, can shape funding decisions, build power, and drive change in their communities.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.
Learn about the Stupski Foundation.
Co-Hosts: Ralph Lewin & Glen Galaich

Guest: Josh Lee | Youth Power Fund
Executive Producer: Claire Callahan
Production Team: Podfly

Graphic Design: Middle MGMT

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