Before the 27-year-old became the third-richest content creator, raking in $38 million in 2023—and challenging boxing legend Mike Tyson to a fight to be aired on Netflix—Paul was Disney’s nightmare employee.

Fresh off gaining internet fame from making six-second comedy videos on Vine, Paul was fired from the children’s show Bizaardvark, where he played stunt-pulling Dirk Mann. In a twisted take on art imitating life, Paul was booted by Disney in 2017 for causing a nuisance with his own stunts, lighting fires in empty swimming pools, brandishing a T-shirt gun at a reporter, and organizing dirt bike drag races outside his rental house.

“We’re not even that loud,” Paul told The Hollywood Reporter after the incidents. “Like, yes, we had a furniture fire get out of control in our backyard one time. But that didn’t harm a single person.”

Even as he garnered a following of 47 million across YouTube and Instagram with his prank videos and behind-the-scenes video blogs of his budding boxing career, trouble continued to follow Paul.  

On top of allegations of sexual assault and the use of racist slurs in YouTube videos, Paul threw raucous parties at the height of COVID and was charged with trespassing and unlawful assembly after being filmed with a stolen bottle of vodka in a looted mall. The charges were later dismissed. But following the mall incident, the FBI also raided his home with a SWAT team in August 2020. The U.S. attorney’s office in Arizona later said he would not face federal charges.

It’s hard to imagine, then, that this same guy would become the face of a venture capital fund that invested in the success of brands like Olipop and Fly By Jing. Or that he would become the founder of a newly birthed personal care brand of deodorant and body spray called W—a play on Gen Z streaming slang for “winning”—that launched this week at 3,900 Walmarts, with more products launching later this month across an additional 400 Walmart locations.

But like the name of his new brand suggests, Paul has continued to find wins despite a wave of “1,000 failures.” After surprisingly—but not inexplicably—snatching victory from the jaws of defeat over and over, Paul has learned to love the controversy.

“Other businessmen understand, and businesswomen understand that when you’re doing something amazing, everyone’s going to try and stop you,” Paul told Fortune. 

The ‘problem child’ grows up

Following the narrative of so many content creators in the mid-2010s, Paul phased out prank videos and turned to other means of making money. He dubbed himself “The Problem Child” and made a name for himself in boxing, where he earned a record of nine wins and one loss. In 2021, he cofounded venture capital fund Anti Fund alongside Geoffrey Woo, an entrepreneur who rejected Paul a decade earlier, when he pitched his content house Team 10. 

Woo told Fortune it’s a common strategy for influencers to try their hand at consumer brands and venture capital after squeezing the juice from YouTube.

“Content creators, or celebrities in general, think it’s a free money grab,” he said.

According to Amanda Russell, marketing consultant and author of The Influencer Code: How to Unlock the Power of Influencer Marketing, it really can be lucrative. Content creators like Paul already have built-in audiences, allowing their brands to scale quickly.

“It’s harder and harder for brands to break through,” Russell told Fortune. “Everything is a commodity now unless consumers have a connection with the product. People don’t really resonate with brands; they resonate with people.”

But Paul will tell you himself that just having his name attached to a venture doesn’t mean success. In 2016 his social media site Locker Room, which divided users into groups for just boys and just girls, shut down after getting only 500 downloads. In 2018, he was accused of scamming customers of his online platform Edfluence, which provided instructional videos on becoming an influencer, after users weren’t able to unlock the videos even after paying the initial $7 fee to do so. And in March 2023, he coughed up $400,000 to the SEC for promoting an alleged crypto scam. 

“You have to go through those moments where you lose money, your idea isn’t as good as you thought it was,” Paul said. “Those are the things that make you in the long run.”

Woodie Hillyard, W’s CEO, saw more of that Paul—the self-aware and humbled entrepreneur with an earnest hunger for success—when he met him a year and a half ago. During one of their first meetings, a group of kids approached Paul asking him for autographs. Hillyard recalled Paul being patient, asking each kid about their interest in school and what sports they liked.

“You just saw him connect with people on a human level, and it just made you realize that he’s a great guy,” Hillyard told Fortune. “People have the opportunity to grow up.”

While Hillyard sees a young business partner with smoothed-out edges and a calm demeanor, Paul, at least to the public, still leans into his troublemaking persona. In a recent promotional video for W, Paul calls himself “dumb and smelly,” asking a production assistant to apply deodorant to his hairy, sweaty pits.

“I don’t personally think I’m controversial. I tell the truth, and people don’t like the truth in today’s world because the truth hurts,” Paul said. “I wasn’t never afraid to ruffle any feathers or speak what’s on my mind.”

‘Content is king’

Don’t dismiss Paul’s bravado. Paul hasn’t succeeded in spite of his controversy, Russell argued. He’s found his professional footing because of it.

“The ones that try to please everyone are really for nobody,” she said. “The more you stand for something, the more that you create a cultlike following.”

Paul is hyperaware of his past delinquency. He’s used his continued relevance, even the infamy, to his advantage: “Content is king,” he said. “The most important thing is eyeballs and marketing and exposure.”

This strategy isn’t foolproof, as the Paul family knows. Older brother Logan Paul found meteoric success in his energy drink brand Prime, which was launched alongside boxer KSI. But after raking in over $1 billion in sales within two years of launching the company, the brand’s rapid growth became unsustainable. 

Gen Alpha lost interest in the drink and latched on to the next hyped-up product. And after getting hit with a lawsuit alleging it contains more caffeine than labeled and “forever chemicals,” Prime bottles are now sitting on discount shelves in U.K. retailers.

But Jake Paul has faith in his winning mentality in the face of adversity. He’s walked through the fires of serious controversies, criminal allegations, and failed businesses, and still comes out on the other side swinging.

“Everyone wants to see you go down, and you just continue to rise to the occasion and overcome and conquer and keep fighting,” Paul said. “And that’s really what I’ve done.”

“Some of my biggest losses were my biggest wins,” he added.