Dan Bilzerian, famous for being a womanizing bro, revealed the secrets of life as the Most Interesting Man on Instagram in an hour-long interview with Howard Stern.

Bilzerian was hungover when he showed up for the interview, and spoke about it with a post on Instagram, writing, “I’m on a strict drug and alcohol regiment to keep my mind limber for the @sternshow in an hr.”

Dan Bilzerian Got His First Gun At 6-Years-Old

Bilzerian, 33, is the son of a millionaire, but, in his interview with Stern, he insisted he made his own fortune playing poker. Bilzerian bosted to Stern that he won $50 million playing poker once and has lost up to $3.6 million in a game.

A gambler from an early age, Bilzerian was honorably discharged from the Navy before he graduated – he claims it was because of his attitude, not his performance. His exit from the military mirrors his earlier expulsion from high school, where he was asked to leave during his senior year after it was discovered that he had a machine gun in his car parked in the school parking lot. Not only did he get kicked out of school, the stunt also earned him 3 weeks in jail.

According to Bilzerian, he received his first firearm at age 6, and he frequently posts photos of himself surrounded by nearly naked women and guns.

Bilzerian is not shy when it comes to his infamous playboy antics, telling Stern that he once slept with 4 women at once, but he also admitted that he wasn’t popular with the ladies until after his time in Navy SEAL training, when he enrolled in college.

Bilzerian Suffered Two Heart Attacks At 25

However, Bilzerian’s hard-partying life hasn’t always yielded enviable results. At 25, Bilzerian suffered his first heart attack caused by a mixture of cocaine, ecstasy, alcohol and 200 milligrams of Viagra (way above the suggested dosage). He had another heart attack 12 hours later.

During the chat, Bilzerian also admitted that he doesn’t play poker too frequently anymore because the highs and lows can get very extreme, and that he recently bought a slightly used private jet.

“I’m pretty smart with my money,” Bilzerian said when asked if he is ever worried he’ll use up his entire fortune with his lavish lifestyle.

Of course, Bilzerian and Stern spoke at length about Bilzerian’s string of women. During the interview, Bilzerian said that he only slept with one woman the night before, and he doesn’t even know her name. While most women Bilzerian sleeps with are models or Playboy Bunny-esque women, Bilzerian charmingly informed Stern, "I did f–k a fat chick once, and that cured me."

As for marriage, Bilzerian doubts he’ll get married any time soon, saying, “I am a gambler, but I don’t want to bet half my net worth that I’ll love her forever.”

Article by Olivia Truffaut-Wong

Olivia Truffaut-Wong was born and raised in Berkeley, California, where she developed her love of all things entertainment. After moving to New York City to earn her degree in Film Studies, she stayed on the East Coast to follow her passion and become an entertainment writer. She lives on a diet of television, movies and food.