For Nathan Fielder, the 43-year-old co-director and narrator, the documentary’s success reflects a major milestone in a career that started with little direction.

Growing up in Canada, Fielder was raised by two social workers, attended public school, and didn’t have cable television at home. As a teenager, he worked at a magic store—a job that offered an early glimpse into the awkward performances and carefully-constructed illusions that would later feature in his comedy.

He discovered improv in high school, where he was once paired with fellow student Seth Rogan. Still, Fielder didn’t immediately pursue a career in comedy. He initially planned to become a dentist, figuring he could “make a lot of money,” he told Grantland in 2014.

Instead, he graduated with a degree in business from the University of Victoria in 2005 and eventually became a broker. But that career didn’t last long: Fielder quit less than a year after finding the job “depressing,” according to a characterization in The New Yorker.

Fielder then began pursuing entertainment more seriously. He enrolled in a comedy program, worked as a junior producer on Canada’s version of American Idol, and eventually became a correspondent on a Canadian TV comedy show. 

The latter experience helped him land writing work at Comedy Central in the U.S.—and set him down a path to becoming a household name.

“I kind of feel as though I’m constantly figuring out new stuff, but I’m also—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 comedy style. 

In 2013, he launched Nathan For You, the 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 style today.

Again, in his subsequent show, The Rehearsal, he often put 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 try my hardest to do it, and that’s basically it,” Fielder added. “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 TV and film—and accumulate an estimated net worth of $5 million. The success of You Can See Everything is only expected to expand that—and even put him in the running for his first Academy Award nomination.

Fielder doesn’t regret taking risks—he uses them as an opportunity to learn a ‘whole new category of skills’

Fielder’s career has been defined by taking risks both in his comedy—and in himself. Even when a project doesn’t go as planned, he sees the experience as an opportunity to adapt by learning 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.’”