“You Can See Everything,” the documentary chronicling disgraced Theranos founder Elizabeth Holmes, is shaping up as a box-office hit. The film took in $15 million during its first week of limited release and could earn as much as $25 million in its second week as it expands to thousands more theaters globally.

For Nathan Fielder, the 43-year-old codirector and narrator, the documentary’s success marks a major milestone in a career that began with little direction. Its expansion also gives Fielder’s work a reach beyond the television series that established his reputation, bringing his experimental approach to a wider film audience.

Fielder grew up in Canada, raised by two social workers. He attended public school, and there was no cable television at home. As a teenager, he worked at a magic store—a job that offered an early glimpse of the awkward performances and carefully constructed illusions that would later surface in his comedy. He discovered improv in high school, where he was once paired with a fellow student, Seth Rogan.

Comedy, however, was not his initial ambition. Fielder first planned to become a dentist, figuring he could “make a lot of money,” he told Grantland in 2014. Instead, he graduated with a business degree from the University of Victoria in 2005 and eventually took a job as a broker. The career did not last: Fielder quit less than a year in after finding the work “depressing,” according to a New York magazine profile of the comedian.

He then turned to entertainment more seriously. Fielder enrolled in a comedy program, worked as a junior producer on Canada’s version of American Idol, and later became a correspondent on a Canadian television comedy show. That experience helped him land writing work at Comedy Central in the U.S.—and set him on the path to becoming a household name.

“I kind of feel as though I’m constantly figuring out new stuff, but … maybe there’s a benefit, in a way, to just doing that,” Fielder said in a recent interview with The A24 Podcast. “Because when you fail, you fail really hard. It’s really bad, but then you figure out a new way of doing things, too, sometimes.”

Fielder built a career by embracing discomfort

Fielder’s willingness to experiment has shaped both his broader career and his comedic style. In 2013, he launched Nathan for You, a Comedy Central series in which he offered struggling businesses outlandish advice, including the now-famous “Dumb Starbucks” stunt. The show ran for four seasons and established the deadpan, cringe-inducing style that has become his signature.

In his subsequent series, The Rehearsal, Fielder often placed himself in awkward social situations, blurring the line between his on-screen persona and his real-life discomfort.

“I’ll put myself in situations that are genuinely hard for the real me to do. And I’ll just my hardest to do it, and that’s basically it,” Fielder said. “Then I don’t have to pretend, really, I’m bad at something, I’m just actually trying my best.”

The approach has helped Fielder build a career spanning television and film—and accumulate an estimated net worth of $5 million. The success of You Can See Everything is only expected to expand that fortune, and could even put him in the running for his first Academy Award nomination.

Fielder doesn’t regret taking risks

Fielder’s career has been defined by risk-taking, both in his comedy and in the projects he pursues. Even when a project does not go as planned, he views the experience as an opportunity to learn skills he can carry into whatever comes next.

“I think I dive into a lot of situations really quickly because I get passionate, and I want to do something,” Fielder said in 2015. “It’s a whole new thing that you’re trying to figure out, and you don’t know how to deal with something, but when you go through it, you now have a whole new category of skills you can use for the future.”

“I don’t have any regrets in my life because of that,” Fielder added. “I notice how I change after doing something, that I go, ‘Crap. I should have done this differently.’”

This story was originally featured on Fortune.com.