From Rock Bottom to Redemption: John Flynn’s Billion-Dollar Comeback

Join us this week on Unlocking Moves, the show that dives into the pivotal moments in a leader’s journey that unlocks their potential. Most people only talk about their “glory” stories, but host Kurt Wilkin believes we learn more from the “gory” stories. This episode delivers both as Kurt sits down with John Flynn — co-founder and former CEO of Open Lending — whose journey from addiction and loss to building a $4 billion company is nothing short of extraordinary.

John opens up about growing up in a blue-collar family, working in steel mills to pay for college, and finding early success in the credit union world. But his ambition masked a destructive secret: alcoholism. After multiple DUIs, a failed marriage, and a near-fatal crash, John hit rock bottom and checked himself into treatment — a decision that changed his life forever. Thirty-four years sober, he credits faith and service as the foundation of his comeback. From that turning point, John went on to co-found Open Lending, helping thousands of borrowers secure fair and affordable auto loans while growing one of the most successful fintech companies in the world.

This conversation explores redemption, resilience, and purpose. John shares how faith gave him strength after the loss of his daughter, how mentorship and second chances shaped his leadership, and why he now dedicates his life to helping others recover through his women’s treatment center, Hammocks on the Edisto. His story proves that the greatest comebacks often start at the lowest points — and that true success is measured not by wealth, but by lives changed.

About John Flynn - John Flynn is the co-founder and former CEO of Open Lending, a financial technology company that reached a $4 billion market cap. A lifelong advocate for addiction recovery, he co-founded Hammocks on the Edisto, a women’s treatment center in South Carolina. John has been sober for 34 years and continues to mentor others on their journey to recovery and leadership.

About Kurt Wilkin - Kurt is a connector - of dots, ideas, and people. For over 30 years, he has advised high-growth companies, starting his career with Ernst & Young and today serving as Founder of BusinessEarth and Managing Partner of Bee Cave Capital. He’s a serial entrepreneur with multiple successful exits and has helped hundreds of entrepreneurs and CEOs build their companies.

Listen now:

Apple Podcasts: https://podcasts.apple.com/us/podcast/unlocking-moves

Spotify: https://podcasters.spotify.com/pod/show/unlockingmoves