Justin Steele gave away nearly $700 million leading Google.org’s philanthropy across the Americas, and he watched funding flow to the nonprofits closest to power rather than those closest to the problem. Now the founder of Kindora, a public benefit corporation using AI to help nonprofits find funders who’d actually say yes, he calls this the legibility trap. In conversation with Dimagi CEO Jonathan Jackson, Justin takes listeners inside a grant maker’s head: how a seven-person team ran a $150 million annual budget, why portfolios so often follow personal networks, and why honest feedback is so rare. They debate whether an LLM tuned on community wisdom could read a grant application more fairly than a program officer, why AI works best as a “junior staff member’s first read,” and why “not a fit” and “not competitive” are very different no’s. Justin also shares his bet on democratizing ownership of Kindora itself through a community crowd raise. Whether you’re fundraising, grant making, or building something mission-driven, you’ll come away with a sharper sense of how capital actually moves, and how it could move better.
Related Resources:
Kindora: Justin’s public benefit corporation. It uses AI to help nonprofits find high-fit funders, map warm connections and draft grant applications
Kindora’s Wefunder Campaign: Support Kindora’s active fundraising campaign and learn more about the opportunity to invest in its mission.
The Legibility Trap (EA Forum): Justin’s article on how “fund the most rigorous thinkers” can quietly favor the wrong organizations.
Outdoorithm Collective: the nonprofit Justin and his wife co-founded to take urban families out into nature. Kindora began as their own fundraising tool.
Incorruptible by Eric Ries: Ries’s new book on why good companies go bad, which Justin and Jon discuss.
The Steve Fund: a nonprofit focused on the mental health of young people of color, and one of the grantees in the Google.org teen mental health portfolio Justin describes.
Decolonizing Wealth Project: founded by Edgar Villanueva, whose “money as medicine” idea Justin cites.
Sign up to our newsletter, and stay informed of Dimagi’s work
We are on social media - follow us for the latest from Dimagi: LinkedIn, Twitter, Facebook, Youtube
If you enjoy this show, please leave us a 5-Star Review and share your favorite episodes with friends.
Hosts: Jonathan Jackson and Amie Vaccaro
