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This week on In Depth, sports figures open up about their dealings with money, including incredible gains, life-changing losses and lessons learned along the way. Some of the biggest names in sports – including Wayne Gretzky, Emmitt Smith, Lewis Hamilton, Billie Jean King and Kevin Harvick – share stories ranging from early introductions to budgets to the mindset after signing that first big contact.

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Graham sits down with Rob Dyrdek at the Fantasy Factory in L.A. to discuss his early pro skating career and the many entrepreneurial successes that followed, including Street League Skateboarding and multiple TV shows with MTV. Dyrdek also addresses his love of performing dangerous stunts and offers Graham a tour of the Factory.

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Richard Branson invites Graham to the Bahamas as Sir Richard hosts his annual Necker Cup Tennis Pro-Am. The three-day episode taping includes an In Depth interview with the British billionaire and humanitarian, plus kitesurfing and commentary from Martina Navratilova and other Pro-Am competitors. Branson shares some of his most impactful stories, including death-defying hot air balloon expeditions, excessive Formula 1 celebrations and overcoming hardships as he ventured into new industries, including commercial space travel.

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