Dan Bilzerian branded himself as the "King of Instagram", even though at the time of this writing, his is ranked as the 140th most followed account on the site (he's coming for you, Brazillian singer Ivete Sangalo!). He is also an actor, entrepreneur, venture capitalist, millionaire, playboy, former high-stakes poker player, recreational weed magnate, two-time Navy SEAL runner-up, and possibly the most suspiciously lucky man to have ever walked the Earth.

If you've managed to come this far in life without knowing who this man is, please turn back now. The extravagant lifestyle he projects is pure elitist entertainment. He has the kind of rabid and toxic fanbase that's normally associated with wild racoons, and he has spawned so many other fake-it-til-you-make-it copycats on social media that it's hard to tell what's real anymore. However, if you were to look at Dan's life under even the world's least powerful microscope, there are so many batshit crazy details that will quickly send you down a rabbit hole of bemused skepticism. The man really is the Forrest Gump of douchebaggery.

It's important to note just how much I tried to give this guy a fair shake when starting to write this article, but there are just so many cartoonishly asinine aspects of this man's life that it was hard enough to narrow it down to the greatest hits, let alone resist the temptation to make fun of him. It's really difficult to not dunk on this guy when he keeps lowering the rim all the time. I mean, just look. At. Him! He looks like a villain in a poorly rendered PS2 game. He's a walking pair of tactical cargo shorts. He looks like if the Smirnoff Ice Challenge was a person. He looks like Zangief's little brother. Okay, got a lot of it out of my system. Let's begin. 

His Entire Poker Career May Have Been a Bluff

Dan Bilzerian attended the University of Florida to study Business and Criminology ... an interesting choice in majors for the son of a Wall Street felon. It was during this time that his brother, Adam, taught him how to play poker, and Dan quickly got himself hooked. As Dan likes to tell it, his online poker habit caused him to be broke by sophomore year, so he sold two of his guns for $750 and tried his luck one more time. Most recovering gambling addicts would call this hitting rock bottom.

But apparently not for Dan. He claims to have used that $750 to play poker on a gambling boat, and turned into $10,000 in a week. He then flew to Vegas and allegedly turned it into $187,000. He began to enter professional tournaments, and even competed in the 2008 World Series of Poker Main Event, placing 180th and winning $36,000. Dan eventually soured on the idea of being on the professional circuit and stuck to private high stakes cash games instead. In November of 2013, he posted that he had won $10.8 million in a single night. For all of 2014, he claims to have won over $50 million on playing private cash games. 

Of course, there's no reason to be suspicious when a man who was doing moderately okay on the professional poker circuit suddenly becoming a multi-millionaire playing private cash games ... around the same time he was finally given access to his trust fund set up by his white-collar criminal father, right? Or that a man who craves the spotlight this much "wins" the bulk of his net worth off-camera, and with no one willing to admit to having lost to him? 

And surely there's nothing to read into this: around the same time professional poker players like Doug Polk started posting videos analyzing the few games Dan actually played on camera, and determined he really wasn't a skillful enough player to be able to pull off such massive wins, Dan decided that poker really wasn't his thing anymore. Convenient, like James Bond's gadgets level convenient.

Instagram Probably Had To Install Extra Servers to Contain This Much Ego

Dan Bilzerian started posting pictures of his life to Instagram in 2012. His earliest posts are rather bland compared to what his feed is today, but once his wealth really took off so did the craziness of his behavior. He admits it himself that once he had all this money, he decided to just cross everything off his bucket list. The result of which, as you can tell from his Insta feed, answers the question: what would happen if a can of AXE suddenly became sentient and won the lottery?

His online persona is emblematic of the alpha bro mindset: wild parties...

Hot girls...

Extravagant locations...

Expensive cars and private jets... 

Celebrities...

And even the occasional exotic animal. 

There are also lots of pics of him firing off big guns and working out, because ALPHA! There's nothing inherently wrong with any of this. If that's how he wants to spend his money, that's his business. That's his image, that's his brand, more power to him. It's just hard to look at some of these posts and not have every question because a lot of them are just baffling. 

Why is he playing chess with his buddy with what looks to be $950,000 in cash stacked up around the table? Why would he even need that much cash at home? What did they say at the bank when he made that withdrawal? He didn't attempt this at the drive-thru teller window, did he? Is his accountant just out of frame freaking the hell out about what that money could be earning in a high yield mutual fund? And finally, assuming this money is the wager on this match, why is he taking a damn phone call when there's almost one million dollars on the line?!? Focus, man, FOCUS! 

It's one thing to have more money than you know what to do with, but it's another thing to demonstrate that to such a degree that these will be the photos Dateline NBC will zoom in on slowly when they cover your inevitable bankruptcy.

Mel Freaking Gibson?!? Who's helping/hurting whose reputation on this one? Without looking at the caption on Instagram, you'd never be able to guess in a million years what these two are talking about in this photo. Answer: stem cell research! What?!? Why does everything taste like copper right now? Anyone else smell burnt toast? And, of course this happened.

He Once Threw a Porn Star off a Roof, and Blamed Them

In April of 2014, Dan Bilzerian took part in a photo shoot at his house for Hustler magazine with adult film star Janice Griffith. At some point during the photo shoot, it was decided to get a shot of Dan throwing Griffith off the roof of his house into the pool below. Janice missed the target by this much, and broke their foot on the side of the pool. Here is video of the incident: 

Now, it is important to note that Griffith agreed to being thrown off the roof, but maybe not for it to also include the kind of weird crotch groping you rarely see outside of a prom limo. Nevertheless, Griffith asked Bilzerian for $85,000 for pain and suffering, which he flatly refused to pay. 

Once lawyers got involved, Dan's attorney responded with a letter that is exactly what you'd expect from the kind of lawyer that would accept Dan Bilzerian as a client. The letter pinned the blame for the incident on Hustler magazine, as well as Griffith for the injury, pointing out that Janice had grabbed Dan's shirt as he threw, causing the toss to fall short of the pool. The letter included many epically assholish quips, including "...like your client, the facts of the claim won't, quite, fly."

But Hustler's lawyers took it one step further, stating the injuries were an "act of God", which is a pretty flimsy legal argument, or one hell of a compliment to Dan Bilzerian's ego.

Hero Complex in Las Vegas

On October 1, 2017, a man named Stephen Paddock opened fire on the crowd attending the Route 91 Harvest Music Festival in Las Vegas from his suite on the 32nd floor of the Mandalay Bay Hotel. 60 people were killed, 411 were wounded, and 867 people were injured in the resulting panic. It was the deadliest mass shooting committed by an individual in American history. 

Dan Bilzerian was there that night and made it out safely ... then he tried to make his way back in. He decided he needed to become the mythical "good guy with a gun." The only problem was he was missing the gun. He did, however, have his gun permit and fake police credentials on him. So, he first tried to find a gun in an open police truck near the stage, and when he struck out there, he tried begging a nearby officer to give him one of his. That officer, understandably responded by saying, "Get the f--- away from me right now!" Dan even uploaded the footage himself! Check out the exchange at the 4:49 mark here.

Dan Bilzerian/YouTube

For a guy like Dan, hearing that cop tell him "I don't know who you are!" must've cut to the bone.

It's honestly impossible to know how to react to seeing him get rejected like that. It's objectively hilarious considering what we know about Dan Bilzerian as a person, but it's also taking place in the middle of a horrific tragedy. It's sorta like watching a circus clown frantically putting a bunch of balloon animals in front of a crashing plane. Yes, this is a deadly serious situation, but did you see that clown?!? Please tell us when it's okay to laugh at that part.

Ignite International Brands, Ltd.

In 2018, Bilzerian founded Ignite International Brands, Ltd., a company that handles the branding, marketing, licensing, sales and distribution of a wide range of cannabis products, and aims to position itself as the world's first global cannabis brand. In an industry that has seen a growth rate of 38% this past year alone, Ignite and it's CEO Dan Bilzerian have managed to pull off what many market watchers thought was impossible: take a $50 million loss selling weed.

Many blame the company's woes on poor management and organization. After all, Ignite is currently on its fifth president since it was founded. Its most recently ousted COO, Curtis Heffernan, filed a lawsuit for wrongful termination and defamation after blowing the whistle over the company's outrageous spending habits, namely Dan Bilzerian's expense account.

What kind of expenses has Dan allegedly been charging to the company? Well, for starters, there's a $15,000 ping pong table, $50k for a bed frame, a Star Wars gun set valued at $65,000, a $75,000 paintball field, a six-figure trip to London, and $200,000 per month rent on the $65 million mansion he's been bragging about owning. The company also allegedly spent $26,000 to boost Dan's Instagram followers. Ignite's financial reports even listed "transportation for hot models" as a write-off. Just to be clear, on a corporate financial report, it was apparently necessary to point out that the models were hot.

"Alright, now let's do a goofy one for the quarterly shareholders report!"

This kind of reckless spending is like something you'd see in a porn parody of The Wolf of Wall Street, yet Ignite has managed to stay in business due to Dan Bilzerian brokering new (and oddly secret) investments in the company, and even putting his own money back into the company himself. This money has to be coming from somewhere, which brings us to...

So, Back To His Dad …

Dan's father was Paul Bilzerian, a notorious corporate raider back in the eighties who was convicted of fraud charges and sent to prison when Dan was just ten years old. Paul was also slapped with a $1.5 million fine, and after losing a civil suit brought on by the SEC, he was ordered to pay back $33.1 million in profits from his crimes plus interest. That tab is now up to $62 million, with only $3.7 million paid so far, and the federal government has spent $8.6 million in their efforts to collect on it over the years. 

Why has the government had such a hard time getting the money out of Paul Bilzerian? Because he hid all of his money in a tangled web of trusts, offshore accounts and shell companies that the feds have been trying to unravel for 30 years. He's also declared bankruptcy twice to try to get out of paying, and since 2007 has been living in Saint Kitts, a country beloved by corporate criminals for its ethics-optional tax laws. In 2019, he renounced his American citizenship, finally giving his cramping middle finger for Uncle Sam a rest.

Lake Co. Police

"How dare you enforce laws I don't like?!"

The Heffernan complaint also notes that Paul was involved in Ignite's management meetings. Further, Paul Bilzerian is also legally forbidden from being in control of any publicly traded company in the United States, which may explain why Ignite is only listed through the Canadian Stock Exchange. Plus, In 2018, Dan, Paul, and Dan's brother Adam flew to Armenia to obtain citizenship there, and so Dan could join the Armenian Armed Forces. The Bilzerian family is proud of their Armenian heritage, and it's admirable that they wish to reconnect with their ancestral homeland. Surely, it's just a coincidence that Armenia does not have an extradition treaty with the United States.

What Next?

Given his track record, it would be incredibly easy to root for Dan Bilzerian's downfall. That is an understandable impulse. But there is a huge difference between wanting him to crash and burn and expecting him to. The fact remains, this guy's story is definitely not gonna have a happy ending. He will be studied in business schools for years as an example of what not to do, or at the very least, be the inspiration for an episode of Law & Order: SVU.

The downward spiral has already seemingly begun. The guy seems to take more and more pleasure lately in taunting his haters and feeding on negative attention. There's just one problem with playing to the haters: it's simply not a sustainable business model. In order to maintain the supply of hate flowing in his direction, he has to keep upping the ante on his own dickishness to keep up with his demand. Eventually he will cross a line he will not be able to uncross.

Kathy Hutchins/Shutterstock

It's also impossible to know where that line might be, because the guy has already buried the bar he's set for himself.

It's important to not get your hopes up waiting for the inevitable schadenfreude, because given the way this man has behaved so far, he seems like exactly the kind of guy who'd take as many people down with him as he possibly can. Looking at the events of this man's life is like watching a NASCAR race: It's fast-paced, action-packed, has way too many bizarre corporate sponsorships, and a crash could happen at any second. Don't get lower-level seating for this one. 

Top image: Kathy Hutchins/Shutterstock

Want More Cracked in Your Life?

Get the One Cracked Fact daily newsletter! With exclusive content & links to the best from Cracked every day, it’s the only email you need. 

Forgot Password?