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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.

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