The PM Podcast — Not Your Money Anymore: A Conversation with Glen Galaich

Date: March 20, 2026
Host: Jay Frost
Guest: Glen Galaich, CEO of the Stupski Foundation

Episode Overview

In this compelling episode, Jay Frost sits down with Glen Galaich—CEO of the Stupski Foundation, host of the "Break Fake Rules" podcast, and author of Why Big Giving Falls Short. Their conversation dives into Glen’s personal journey from studying political science and ethnic conflict to leading one of the Bay Area’s most progressive “spend down” foundations. The episode dissects power in philanthropy, the mechanics and ethics of foundation spend downs, and Glen’s bold critique of how traditional philanthropy overlooks its own flaws and potential. Listeners gain insight into Glen’s perspectives on democracy, hierarchy, and the urgent need for foundations to unleash locked-up assets for greater, more immediate impact.

Key Discussion Points and Insights

1. Glen Galaich’s Origin Story and Worldview

• Growing Up and Early Influences

  • Glen grew up in San Diego, later moving to the Bay Area (01:46). He was not always interested in the issues he engages with now.
  • He credits his growing interest in power dynamics to a time when the world was optimistic about democracy—namely, the "third democratic wave" post-1989 (03:07).
  • Glen aspired to help write constitutions for newly democratizing African nations, diving deep into ethnic conflict theory (03:50).

    "It's very hard to get past segment issues...almost all of those models...have all failed." — Glen Galaich (05:25)

• The “Strongman” Dynamic and Democracy as Experiment

  • Societies revert to patriarchal, hierarchical leadership structures in times of change or uncertainty (08:40).

    "Humans have a need for that kind of hierarchy...anything you're doing in democracy is really trying to upend that natural order of humanity. And it is, it's not an easy experiment." — Glen Galaich (10:43)

• Personal Relationship to Power and Philanthropy

  • Glen reflects on how political science at its core is about the study of power—how it’s balanced, shifted, or abused (12:13).
  • His family background included both wealth and "fomented class division"—his mother was effectively kicked out of the upper class (14:26).

    "My father...still calls it 'philanthropy.' I cannot for the life of me get him to see that H. So that's how little it was in my house." — Glen Galaich (14:26)

2. Entering Philanthropy: From Academia to Human Rights

• Global Philanthropy Forum & Accidental Entry

  • Glen describes the early 2000s Bay Area boom, his work launching the Global Philanthropy Forum, and his learning curve about philanthropy’s mechanics (18:20).

    "I just assumed everybody got grants from the National Science Foundation. I didn't know about philanthropy." — Glen Galaich (19:50)

• Human Rights Watch Years

  • At HRW, he witnessed the sector’s growth in influence, with budgets expanding to let NGOs sit "almost on the level of states" (22:46).
  • Human Rights Watch works under international law frameworks but, in reality, power—not law—determines progress (26:23).

    "There really isn't an international legal order. There's a hope for one...but power is the structure." — Glen Galaich (28:06)

3. The Realities and Rhetoric of Philanthropic Power

• Money, Power, and Impact

  • Discusses philanthropy as a mechanism of power; most foundations only deploy 5% of assets while 95% remains invested, often in “harmful stuff” (00:00, 32:13).

    "95% of a foundation's assets are going to be in horrible stuff. It's the 5% that we spend all of our time talking about." — Glen Galaich (00:00, restated at 42:22)

  • Strategic philanthropy’s emphasis on impact evaluation is mostly performative, with little demonstrable difference in outcomes (“all a bunch of folly”) (33:10).

    "There's really nothing I just said actually, in my opinion, works. And what's really clear to me is there is just no such thing as foundation impact, nor the ability to evaluate it or track it. It's just annoying waste of time stuff." — Glen Galaich (33:10)

4. Spend Down—Structure, Philosophy, and Emotional Realities

• Stupski Foundation's Spend Down Approach

  • The Stupski Foundation, under Glen and founder Joyce, will fully spend down its assets by end of 2027 (~$600 million), focusing on the Bay Area and Hawaii with a racial equity lens (37:23, 32:13).
  • The deliberate spend down means releasing far more to communities during the foundation’s lifetime than had it followed the 5% model (37:23).

    "If we had not been a spend down, we would have been $160 million over that time and there'd still be the same amount in the corpus." — Jay Frost/Glen Galaich (37:30)

• Operational Mechanics

  • To avoid harmful investments, the foundation moved to cash and invested operational reserves as interest-free loans to community lenders (39:37–41:52).

    "We moved all of it and it backed out to community lenders with no interest on it so they could make all the money off the interest. We didn't need it, we didn't want it." — Glen Galaich (40:51)

  • Glen underscores the emotional spectrum within his team as spend down approaches—the clarity of a known end date is bittersweet (42:22).

    "It's a lot better to know the flight path than to wake up one morning and find out that your program's been eliminated and you're out...I love the people I work with, and I know a lot of people say that, but it takes a really special group to do this." — Glen Galaich (42:22)

5. Glen’s Challenge to the Sector & "Why Big Giving Falls Short"

• Critique of the Sector

  • Glen is vocal about philanthropy's systemic refusal to challenge donor control, the myth of impact tracking, and resistance to transparency around investments (47:30).

    "Most donors, when you ask them about the foundation they govern, they will refer to it as their foundation and their money. And neither of those things are true. But that's what they've told themselves and that's what their staff has been told, and that's what they believe." — Glen Galaich (53:04)

• Invitation to Change

  • The upcoming book Why Big Giving Falls Short invites donors to move from excessive control towards genuine community engagement (47:30–55:20).

    "If you can say to yourself that that is not your money anymore, then you are, you are ready to start approaching community engagement." — Glen Galaich (53:04)

  • Glen’s hope: more donors will embrace trust-based philanthropy and confront how much "harmful stuff" their assets are supporting.

    "There are so many people who have shown you the way. I'm just trying to help people see it. That's all I'm trying to do." — Glen Galaich (55:12)

Notable Quotes & Memorable Moments

• On the “Spend Down” Movement
  "We wish they could see the brightness of what a spend down environment provides to not only you as an organization, but to the sector that so desperately needs the assets that are tied up in such harmful stuff." — Glen Galaich (00:00, 42:22)

• On Power Structures
  "Most of how you can look at humanity and why a person decides or an organization or individual decides to do what it does, it's driven by three forces...culture, self-interest, and structures." — Glen Galaich (26:23)

• On Foundation Impact
  "There is just no such thing as foundation impact, nor the ability to evaluate it or track it. It's just annoying waste of time stuff." — Glen Galaich (33:10)

• On Letting Go of Control
  "If you can say to yourself that that is not your money anymore, then you are...ready to start approaching community engagement." — Glen Galaich (53:04)

• On Reflections and Sector Empathy
  "I have a lot of empathy for donors and I have a lot of empathy for my friends and peers who continue to practice this stuff in such, in my mind, irresponsible ways, honestly. But I don't... It's a system. We're playing a role in it. And it's the way power distributes." — Glen Galaich (54:48)

Timestamps for Key Segments

• 00:00 / 42:22 — Opening blast at foundations for locking up assets
• 03:07 — The third democratic wave and 1990s optimism for democracy
• 08:40–12:13 — The lure of hierarchy and strongman rule, both globally and at home
• 14:26 — Family history: class, wealth, and the accidental influence on Glen’s worldview
• 18:20–19:50 — Glen discovers philanthropy’s breadth—“individuals give you money for what you do”
• 22:46–30:43 — Human Rights Watch, international law, and power as the final arbiter
• 32:13–33:10 — The fallacy of impact measurement in foundations
• 37:23–41:52 — The Stupski Foundation’s spend down strategy, practical and philosophical
• 42:22–46:37 — Emotional reality of spend down, team reflections, and parting thoughts
• 47:30–55:12 — Upcoming book: Why Big Giving Falls Short, challenging donor control, a sector call to action

Tone and Style

Glen Galaich is candid, self-deprecating, and emotionally invested; the conversation is peppered with both warmth and frustration, calling out sector complacency while emphasizing his ongoing hope for change. Jay Frost’s questions are probing, insightful, and gently personal.

Additional Links and Resources

• Stupski Foundation
• Why Big Giving Falls Short (available March 17, 2026)
• Break Fake Rules Podcast
• "Who Gives?" newsletter (in partnership with Ari Allen)
• Philanthropy Confidential Newsletter by Jen Nguyen

This episode offers a masterclass in examining the intersection of power, philanthropy, and societal impact—delivering both critique and inspiration for anyone involved in, or simply curious about, modern philanthropic practice.