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.

The bankruptcy case, which hasn’t been reported in the news yet, provides an inside look at the business of being Bilzerian – the so-called King of Instagram who lives in Las Vegas, displays a famously over-the-top lifestyle and has donated piles of money to Nevada political causes and candidates. Bilzerian still has business ventures in operation and has said he is worth US$350mil (RM1.4bil), vastly higher than his holding company’s reported debts.

He could also cash in on his 5-acre Las Vegas compound, which he recently put up for sale at US$25mil (RM105mil). Famous for being famous, the often partying influencer has claimed huge winnings in poker and promoted himself as a playboy who flies in private aircraft, fires heavy guns and is always surrounded by beautiful women. Public records, however, show a different side of the story.

The bankruptcy proceedings have opened a window to his high expenses, extensive financial support from his family, legal batt.