The PM Podcast: “Monkey On My Back: A Conversation with David Callahan”
Host: Jay Frost | Guest: David Callahan | Release Date: September 5, 2025

Episode Overview

This episode features a candid, insightful conversation between Jay Frost and David Callahan, founder and editor of Inside Philanthropy and Blue Tent. They chart Callahan’s journey from his upbringing in a world of ideas and fundraising, through his critique of philanthropic power and its impact on democracy, and conclude with reflections on political engagement and the shifting landscape of American giving. Callahan shares personal anecdotes, historical context, and forthright critiques, offering listeners an in-depth look at the ethics, influence, and future of philanthropy.

Key Discussion Points and Insights

1. Origins: Ethics, Power, and the “Monkey on My Back”

• Family Influence and Early Awareness of Inequality

  • Callahan grew up in Hastings on Hudson, NY, surrounded by conversations on bioethics and fundraising, as his father co-founded a think tank.
  • “I was acutely aware as a teenager or even before that I had been born into this incredibly high position in the grand scheme of things in the world... I had won the ovarian lottery.” (08:42)
  • “I've often sort of thought of it as kind of a monkey on my back, you know, this desire to make the world a better place and this awareness of suffering and inequality.” (08:42-09:24)

• Social Justice Orientation: Internal Drive vs. Upbringing

  • Not all his siblings shared his sense of responsibility, suggesting both nature and nurture at play.
  • He discusses the challenge of carrying this sense of duty and the impossibility, for him, of stepping away from meaningful work.

2. Early Career: From Policy to Practice

• Path to Philanthropic Critique

  • Engaged with national security issues in college, wrote on diplomat Paul Nitze, and earned a PhD at Princeton, but avoided electoral politics.
  • Wrote Unwinnable Wars, discussing U.S. interventions and humanitarian decisions.
  • Notes the weight of government policy on life and death globally, shifting eventually from foreign to domestic focus.

• Foundation and Think Tank Experience

  • Joked: “I got a PhD so I didn't have to work twice as hard to prove I was just as smart.” (14:37)
  • Early job at 20th Century Fund exposed him to grantmaking and philanthropy from the inside.
  • Co-founded Demos, a think tank focused on economic and political inequality.

3. Building Demos and Critiques of Philanthropy

• The Challenge of Support and Scale

  • Consistent frustration with “near-starvation diets” for progressive nonprofits, in contrast to conservative funders’ multi-year, large-scale, general operating support.
  • “I've long felt that the way in which these foundations spread their grants around so thinly... has, you know, is really problematic.” (23:13)

• Strategic Approaches: Left vs. Right

  • Conservative philanthropy seen as more strategic and power-oriented:
    • Invests in think tanks, media, ideas, legal groups, and leadership pipelines.
    • “They've invested a lot in legal groups... and heavily in media and narrative because they understand that if you control the narrative, you will help structure debates.” (25:49)
  • Left-of-center philanthropy is more technocratic, issue-by-issue, less coordinated.

4. Transition to Inside Philanthropy: Accountability and Media Entrepreneurship

• A Bold Move to Media

  • “I was interested. You know, I'm a writer and blogger... and of course thought that being an Entrepreneur seemed really cool and exciting.” (28:55)

• Business Model Validation

  • Paid subscriptions aimed at grant seekers and makers, offering intelligence valued by both.

• Initial Challenges

  • “I often joke that initially Inside Philanthropy was really outside philanthropy because we were just on the outside blogging and loving hand grenades.” (33:00–34:55)
  • Opaque, insular nature of philanthropy made access and reporting difficult at first.

• Sector Accountability Issues

  • “The lack of accountability, the feeling like, you know, it doesn't really matter whether you pay any attention to the outside world. The insularity of philanthropy and... a kind of arrogance.” (36:30)

5. Transparency, Power, and the Social Contract

• Transparency Shortfalls and Donor Advised Funds (DAFs)

  • Criticizes the breakdown of the traditional “social contract” between philanthropists and the public.
  • “[DAFs]—no payout requirement, no transparency... all these elements of the social contract around philanthropy have broken down.” (37:08–40:12)
  • Notes that the philanthropic establishment shows little interest in reform or greater openness.

• Donor Anonymity and Political Polarization

  • Calls for transparency around giving to policy organizations, but recognizes current political climate complicates reform:
  • “In the current political environment, with the high levels of polarization and weaponization, I am not in favor of... revisiting laws around transparency and nonprofits.” (41:07)

6. Who Holds Power? Fragmentation and Changing Landscape

• Legacy vs. New Philanthropy

  • Old “establishment” of Ford, Rockefeller, Carnegie joined by new mega-donors with different approaches (LLCs, less collaboration, less transparency).
  • “Things are much more diffuse and fragmented than they were a few decades ago.” (42:47)

• Vulnerability and Mutual Support

  • Sector more vulnerable to political attack; certain donors or intermediaries “picked off.”
  • Foundations uniting under “Unite in Advance” to pledge mutual assistance against possible government weaponization. (47:04)

7. The Givers and the Future of Philanthropy vs. Democracy

• Philanthropy as Political Money

  • “Philanthropy as a kind of political money... it's tax deductible dollars that goes to think tanks and legal groups and is used for [influence].” (48:34)
  • Describes three tributaries of money in politics: campaign dollars, lobbying, and philanthropic spending.

• Growth of Donor Power: Looking Ahead

  • Warns of an impending era where the very wealthy create even larger philanthropic institutions as public budgets shrink.
  • “We could see foundations that dwarf the size of foundations that exist today and... exercising influence in more and more different corners of American life.” (51:29)

8. Blue Tent and Activist Philanthropy

• Direct Political Involvement Post-2021

  • Blue Tent created to move money more efficiently to voter engagement efforts supporting Democrats, motivated by alarm over the “authoritarian turn” of the GOP.
  • “I have to get involved in electoral politics because if we lose our democracy... everything else I care about is going to be washed away.” (54:15)

• Effectiveness of Philanthropic Political Giving

  • Notes much Democratic fundraising goes to ineffective advertising rather than strategic voter outreach.
  • “A lot of that money was spent on ineffective advertising as opposed to spending spent on turning out voters in key congressional districts. The resources are not deployed strategically.” (57:19)

9. Personal Mission and Closing Thoughts

• Continued Evolution in Aims and Methods

  • “I've always had this social justice monkey on my back... and I always ask the question... where am I making my unique contribution? How am I deploying my competitive advantage... to make the world a better place?” (58:33)

  • Open to future evolutions: more focus on politics or deeper into philanthropy.

Notable Quotes & Memorable Moments

• “I've often sort of thought of it as kind of a monkey on my back... this awareness of suffering and inequality in the world and in your own country, that's a big burden to carry around.” (08:42)

• “I think that conservative funders are more strategic... They are very focused on power and how to get it and how to leverage their scarce resources.” (25:49)

• “It's very problematic... The insularity of philanthropy and... a kind of arrogance of, 'we don't have to pay attention to anybody.'” (36:30)

• “Philanthropy as a kind of political money. It is used for influence... it’s a mighty river with three tributaries.” (48:34)

• “We could see foundations that dwarf the size of foundations that exist today and... their influence will grow greater as federal, state and local spending is squeezed... all these billionaires will be showing up with ever larger amounts of money just in time to be the people who help fill the gap.” (51:29)

• “I've always had this social justice monkey on my back... I always ask the question, which I think everybody should, is like, where am I making my unique contribution?” (58:33)

Timestamps for Major Segments

• [00:00–09:24] Early life, family influence, and the origins of Callahan's social justice commitment
• [09:53–13:51] Initial political engagement, focus on foreign and domestic policy
• [14:37–20:11] Move to think tank sector; founding Demos, early experiences with philanthropic fundraising
• [20:11–23:13] Challenges with philanthropy, success and disappointment in nonprofit funding
• [23:13–25:49] Strategic differences: conservative vs. progressive philanthropy
• [28:55–34:55] Launching Inside Philanthropy, hurdles in access, and building credibility
• [36:26–42:33] Accountability, transparency, and the evolving “establishment”
• [47:04–53:53] Sector-wide vulnerability, mega-donor power, predictions for philanthropy versus democracy’s future
• [54:15–58:33] Blue Tent and electoral engagement; strategic philanthropic influence in US politics
• [58:33–59:36] Callahan’s ongoing mission and outlook

Tone and Language

The episode combines a reflective, frank, and sometimes critical tone, matching Callahan’s deep familiarity with and concern for the sector, as well as his wry humor (“I often joke that initially Inside Philanthropy was really outside philanthropy”). Host Jay Frost’s approach is insightful, supportive, and probing, drawing out the nuances and implications of Callahan’s ideas for listeners invested in philanthropy, politics, or both.

Summary Prepared For:

• Listeners curious about the intersection of philanthropy, politics, and social justice
• Anyone seeking plainspoken insight into the structural challenges, ethical dilemmas, and real-world frustrations of American giving today

Key Takeaway:
David Callahan’s journey is emblematic of the complexities, burdens, and hopes that come with trying to “make the world a better place”—in a system where the lines between power, generosity, and democracy are constantly being redrawn.