The Funder Breaking All the (Fake) Rules

Designing Tomorrow: Creative Strategies for Social Impact

What if philanthropy, as we know it, is a flawed system?
In this episode, we're joined by Jen Nguyen, a director at the Stupski Foundation, a unique "spend-down" organization designed to close its doors after giving away all of its assets by 2029. Jen, a former college counselor, provides an unapologetically candid look at a sector she may soon leave, revealing a rare freedom to challenge the status quo from within.
We'll discuss how a "wait and see" approach to philanthropy falls short in moments of crisis, why foundations often prioritize their own survival over the needs of the communities they serve, and what it truly means to lead with a "nothing to lose" philosophy. Jen unpacks her critiques of the 5% payout rule, the "overhead" myth, and the power imbalances between funders and the organizations on the front lines.
This conversation is a must-listen if you've ever wondered what a more just, trusting, and effective philanthropic sector could look like, or if the "rainy day" that so many foundations are saving for is already here. ⛈️
Notable Quotes
“The rainy day is here. So what are we saving for? What good is the Stupski Foundation going to be if it exists 50 years from now?” — Jen
[06:05]
“In my opinion, my job is not hard. The work is hard... We just need to give out money more quickly.” — Jen
[28:24]
“We need to be able to value that solidarity… The philanthropic field is set up to reflect capitalism, competition….” — Jen
[34:50]
“It’s their practices that are causing executive directors to have to stretch themselves into different practices and way too thin….” — Jen
[40:42]
Timestamps
[00:00] The “Wait and See” Approach
[01:03] The Flaws of Institutional Philanthropy
[02:18] Why Funders Are Reluctant to Speak Out
[03:55] A Crisis of Government Funding
[07:01] The Spend-Down Foundation Model
[10:09] Rethinking Trust-Based Philanthropy
[14:49] The Proper Role of Philanthropy
[19:38] Balancing Intentionality and Impact
[22:16] A Magic Wand for Philanthropy
[26:22] The Problem with Due Diligence
[29:22] What Philanthropy Can Learn from Venture Capital
[35:32] The Overhead Conversation
[40:33] Advice for Foundations
[42:28] Advice for Nonprofit Leaders
[46:31] Where to Connect with Jen and the Stupski Foundation
P.S. — Feeling a disconnect between your mission and your brand? Cosmic helps social impact leaders build trust through story-rich brands, compelling campaigns, and values-aligned strategy. Let’s talk about how to elevate your impact: https://designbycosmic.com/

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