Who is Dan Bilzerian? Read our exclusive cover interview with the controversial King of Instagram...

The $850K cycle ride

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Perhaps Dan Bilzerian’s most famous bet – and one that drew global attention – came when the Instagram star cycled 270 miles from Los Angeles to Las Vegas in under 48 hours. Venture capitalist Bill Perkins bet $600,000 that such a ride could not be done; rival poker player Rick Salomon added a side bet of $250,000 against Bilzerian’s private jet that Bilzerian would die in the attempt. After enlisting the help of Lance Armstrong, revamping his diet and training like a madman, Bilzerian finished the ride in 33 hours – and then promptly spent several days in bed.

The $6m coin toss

Perhaps the most costly coin flip not conducted by Two Face. Bilzerian loves a bet, but hates the anticipation of finding whether or not his wager will be successful. Therefore the instant gratification of a coin toss is the ideal outlet on which to wager millions of dollars – unless of course you call wrong. Bilzerian called wrong. “I was like, whatever,” he told chat show host Graham Bensinger. “F**k.”

The $10.8m poker game

The Bilzerian fortune was made at the poker table – and when you walk away with eight figures of winnings from a single session, you can afford to lose the odd coin toss. In 2014 Bilzerian tweeted, “Won 10.8 million last night playing poker, headed to Puerto Vallarta to relax” – the accompanying image showed Bilzerian strolling toward a private jet. Bilzerian specialised in winning large sums of money from wealthy, casual players; you can’t argue with the business model.

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The $342,150 boxing match

Bilzerian nearly bet $2m on Floyd Mayweather to beat Manny Pacquiao in the 2015 superfight but he backed out at the last minute, fearful of the money Mayweather stood to gain on a loss followed by an even-bigger rematch. (Mayweather transpired to value legacy even more than money, and comfortably outpointed the Filipino. When Mayweather met MMA fighter Conor McGregor two years later, Bilzerian learnt his lesson and lumped big on Floyd; it wasn’t $2m but still a tidy profit nonetheless. (Bonus points as it was the closest you’ll ever get to free money: McGregor, a boxing novice, taking on a guy with a record of 49-0.)

The Atlantic rowing trip?

Bilzerian told chat-show host Larry King of his wish to row across the Atlantic Ocean – provided he can find someone to bet against him. “I’ve got to be paid something, right?” he said of the challenge. Otherwise three months rowing across the sea isn’t enough of an incentive. “My ego’s not that big anymore. I don’t need to prove anything.” Well, if Perkins isn’t game, maybe it’s time to go double or nothing on that coin toss…

Read our exclusive interview with Dan Bilzerian