When Dan Bilzerian posted a video of himself wake surfing off a megayacht along Italy’s Amalfi Coast, he offered some guidance.

“Someone asked me the other day what advice I’d give to a 20 yr old and my answer was, try everything,” the Las Vegas social-media celebrity wrote last year.

A few months later, behind the scenes of his macho persona, Bilzerian did something that contradicted the wealthy, freewheeling and successful image he has long tried to cultivate: A holding company he owns filed for bankruptcy.