Coach, Business Success & Podcaster Roy Castleman: From Near Death to 7-Figure Entrepreneur

Famous Interviews with Joe Dimino · Sep 23, 2026 · 24m

Welcome to a new edition of the Famous Interviews with Joe Dimino series. On this episode, we talk with Serial Entrepreneur, Coach & Podcaster Roy Castleman about near-death experiences, entrepreneurship, failure, resilience, regret, mental health, and completely rebuilding your life.

At 19, Roy was hit by a drunk driver traveling 70 mph on a South African motorway. Lying broken on the road, he wasn't consumed by the pain — he was consumed by regret over everything he hadn't done.

That moment became his blueprint for living without limits.

After emigrating to the UK in 1997 with just £75 in…