As a professional poker player Dan Bilzerian is used to making large bets.
In 2014 he told US shock jock Howard Stern he'd won $50 million playing poker in the previous 12 months and had once lost $3.6 million in one game.
He's also shown a willingness to gamble away from the tables, challenging Supreme Court lawyer Tom Goldstein to a drag race a few years back and pocketing more than half a million dollars (AUD).
But his latest wager is going to test him like never before.
For reasons that remain unclear, the 35-year-old has bet fellow high-stakes poker player Bill Perkins $800,000 he can ride a bike from Los Angeles to Las Vegas in less than 48 hours.
That's more than 500km on two wheels - a brutal stretch for a man who says he hasn't ridden a bike in 18 years.
But when you're Dan Bilzerian there's always someone ridiculously famous willing to give you a hand.
After inheriting great personal wealth from his father - a successful corporate raider on Wall Street - Bilzerian has been living the dream.
He's earnt a reputation as the King of Instagram by posting images of himself - most often with guns and scantily-clad women - to an audience of more than 16 million followers.
He's also very well-connected.
Bilzerian woke a few weeks back to a message from popular UFC commentator Joe Rogan alerting him to the fact none other than Lance Armstrong was happy to give him some one-on-one training ahead of his ride.
The disgraced drug cheat can do with any good publicity he can get these days, so teaming up with Bilzerian must have seemed like a good idea.
Bilzerian was more than willing to accept the hand. He'll face steep climbs and desert conditions en route from California to Nevada, which he must tackle before the end of March, according to the rules of the bet.
Despite the challenge, Bilzerian's overall fitness has seen bookmaker Ladbrokes open him as a $1.75 favourite to win.