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 his bank account, Roy went on to build multiple 7-figure IT companies, survive the 2008 financial crash, and eventually acquire the very company where he had started his career as an engineer.
He thought he had it figured out.
Then he bought an adventure centre just before COVID, lost nearly everything, and eventually found himself in a hospital bed at rock bottom. That experience became the catalyst for another transformation and a new mission: helping entrepreneurs avoid the regret that once consumed him and build businesses and lives they can truly be proud of.
In this powerful conversation, we cover the whole story — from South Africa and a near-fatal accident to entrepreneurship, wealth, business failures, COVID, rock bottom, reinvention, coaching, and discovering a deeper purpose.
More Roy Castleman:
https://www.atpbos.com/
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