Instagram's favorite millionaire playboy, Dan Bilzerian, sits down with the King of Media, Howard Stern, to talk about what it's really like to live the life of the man touted to be the next Hugh Hefner.

Typically, the professional poker player-turned-actor announced his interview through an Instagram post on Monday. In the hour-long interview, Dan revealed some of his most personal stories ranging from his high school life, his father, and his "girls".

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Although widely known for his awesome skills in the poker table, Dan advises those aiming to become a professional poker player like himself to not push through their plans.

He says that the game destroys your value of money, even claims that the "highs aren't as highs as the lows are low." He revealed to have lost US$3.6 million on three separate occasions, but won a net of US$50 million this year. Confessing that gambling was the only thing that gave him a rush after going through the military, he admits that he wants to stop.   

Growing up, Dan has never been a stranger to a lavish lifestyle. His dad, Paul Bilzerian, was once valued at US$400 million.

Their lives took an unexpected turn in 1989 when his dad was indicted for some white collar crime charges. Determined to help his dad get out of jail, Dan put up a third of his own trust fund money as contribution.

However, this valiant effort only served to anger his father. Paul claimed that Dan acted without thinking, which ended up with him handing over so much to the government. His father did not talk to him for eight months after this incident.

In 1999, Dan was kicked out of the state of Utah for bringing an M-16 to his high school. The gun was discovered in the trunk of his car by school administrators after Dan himself bragged about his weapon to his schoolmates. The school officials then asked him to leave the high school and the state. However, his record has long been expunged and he's now welcome back into Utah.

His ejection from Utah led him to join the military. After completing 510 days of SEAL Training, he was once again kicked out two days before graduation for a "safety violation." Dan claims that the real problem involved his commanding officers disliking his aversion to authority. He finished off receiving an honorable discharge after four years in the military.

Surprisingly, Dan reveals he was not much of a playboy in high school and during his days in the military. In fact, he claims to barely hook up with girls in his younger days. He thinks his present preoccupation with the ladies is his way of making up for lost time. Although he's been in situation where a lot of girls were present in the room, he claims that the most amount of girls he has ever been physically intimate with at one time was four.

Although it may not be common knowledge, Dan is a strikingly intelligent guy. He scored 94 out of 99 on the military intelligence test and 1340 on his SAT. He has also experienced two heart attacks, one large one and one minor one. Both attacks happened 24 hours apart from each other.

TagsDan Bilzerian, playboy, poker, The Howard Stern Show