In this full-circle episode of the Square Pizza Podcast, host Greg Schermbeck reconnects with Jason Terrell, President of the R. Howard Dobbs Jr. Foundation, for a wide-ranging and insightful conversation on fatherhood, leadership, and the evolving world of philanthropy.
Jason reflects on how his personal and professional journey has shifted since his last appearance in 2020—moving from nonprofit founder to a philanthropic leader with a statewide platform. Along the way, he shares what it means to lead with trust, how his thinking has evolved, and why the future of meaningful giving lies in deeper collaboration and intersectionality.
In this episode, you’ll hear:
- Jason’s reflections on parenting and how teaching and leadership tools show up at home
- His career shift from Profound Gentlemen to leading a $65M foundation with a two-person team
- Why philanthropy is more fragile than it appears—and what nonprofit leaders need to understand
- The Dobbs Foundation’s approach to funding education, health, and the environment, and how Jason applies a “multi-solving” lens to support holistic change
- The growing role of AI in philanthropy, from data transparency to democratizing access to information
- A call for funders to serve as learning engines, not just check writers, and to prioritize trust and flexibility alongside accountability
This episode is for nonprofit leaders, funders, and anyone navigating the intersections of community work, equity, and innovation. Jason’s honesty and strategic clarity offer a blueprint for how philanthropy can evolve without losing its heart.
Popular Podcasts
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com