Break Fake Rules: Change Big Giving For Good

In the wake of the midterm elections, the question remains: will institutional philanthropy strengthen our communities and democracy, or will it continue operating by fake rules that entrench inequality forever?
Co-hosts Eric Brown, Principal of Brownbridge Strategies, and Glen Galaich, CEO of the Stupski Foundation, break down the results and outline the opportunity ahead for philanthropy to fuel the changes communities overwhelmingly demanded at the ballot box. Special guest Aparna Rae, speaker, workshop facilitator, journalist, and Forbes contributor, joins them to question whether institutional philanthropy strengthens democracy or reinforces the inequalities it claims to address. Drawing on her reporting on the nonprofit workforce crisis, Aparna describes widespread layoffs, financial insecurity, and a sector struggling to measure the true extent of its losses.
Aparna argues the problem goes far beyond inadequate funding. She challenges a system in which publicly subsidized wealth remains under private control while nonprofits struggle to sustain their workers and communities. From foundation investments that may perpetuate the problems philanthropy seeks to solve to charitable dollars sitting in donor-advised funds, Aparna questions whether these institutions are serving the public or simply preserving themselves. Her proposal is provocative: use philanthropy to help dismantle philanthropy.
💡 Aparna Rae: “We need philanthropy to help dismantle philanthropy. I'm not saying that we give up the idea of helping people in need, but modern philanthropy, I think, is extremely caustic.”
💡 Eric Brown: “What can philanthropy, if it can at all do, to be a part of that of a solution that allows us to reclaim a democracy, solidify the things that we value in this country, and move beyond the crazy little moment?”
Read Aparna Rae's Forbes article, The Invisible Job Crisis: America's Third-Largest Employer Is Hemorrhaging Talent, which examines the employment crisis affecting nonprofit workers and the sector's ability to serve communities.
Explore her follow-up article, Nonprofit Workers Are In Crisis. Funders And Policymakers Have The Tools To Fix It., on the funding practices and working conditions contributing to the crisis.
Read Catherine Liu's Virtue Hoarders: The Case Against the Professional Managerial Class, which Aparna recommends during the conversation about professional privilege and institutional power.
Read Glen’s latest Substack on What Comes After a Win?
Order your copy of Glen's book, CONTROL: Why Big Giving Falls Short.
Learn about the Stupski Foundation.
Co-Hosts: Eric Brown & Glen Galaich
Guest: Aparna Rae
Production Team: Podfly
Graphic Design: Middle MGMT

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 Galaich
Guests: Carol Cheney & Katie Carter
Executive Producers: Claire Callahan, Aya Tsuruta & Emily Daman
Production Team: SeeBoundless & Podfly
Graphic Design: Middle MGMT

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

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

Break Fake Rules listeners, enjoy this special feed swap from our partners at the Center for Effective Philanthropy (CEP), who invited our co-hosts, Glen Galaich and Jamie Allison, to guest star on their Giving Done Right podcast. Follow Giving Done Right here or wherever you get podcasts. New episodes of Break Fake Rules return next week.
In this episode, co-hosts Phil Buchanan and Elisha Smith Arrillaga, CEP's vice president of Research, discuss some of philanthropy's oldest tensions: who should decide how charitable dollars get spent and how to balance short-term needs with the long view? Their guests, Glen Galaich, CEO of the Stupski Foundation, and Jamie Allison, executive director of the Walter & Elise Haas Fund, are usually the ones asking the questions, as frequent co-hosts on Glen’s podcast, Break Fake Rules.
Glen makes the case from his new book, “CONTROL: Why Big Giving Falls Short”, that too much charitable wealth sits parked in private equity and hedge fund accounts rather than moving out to the communities that need it, and that donors should treat public stewardship, not private control, as their guiding value. Jamie pushes back on the idea that this is a binary choice between spending down and staying perpetual, describing how the Walter & Elise Haas Fund has worked to increase payout and shift toward larger, unrestricted grants without abandoning a long time horizon. Together, they debate what foundations with large endowments owe to this moment of crisis for nonprofits, why "responsiveness" matters more than any single spending formula, and what foundations might learn from everyday donors.
Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.