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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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Graham spends the day in Austin with billionaire businessman and dedicated philanthropist, John Paul DeJoria. The co-founder of both Paul Mitchell hair products (John Paul Mitchell Systems) and The Patron Spirits Company, DeJoria opens up about his rise from homelessness to Hells Angels to massive wealth, complete with sponsorship of multiple sports teams and a portfolio of charitable endeavors. He shows Graham around his home, his collection of cars and motorcycles, then to an affordable housing community designed to help the homeless rejoin society. John Paul's wife Eloise and daughter Alexis - the recently retired NHRA drag racing star- drop in to share stories of finding love and fast cars, respectively.

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