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- Conan O’Brien, who has built a $200 million fortune through television and his Team Coco media ventures, said it’s important to seize opportunities even if you don’t feel ready for them, drawing on his own experiences as a former comedy writer who was given the chance to become a late-night TV host. O’Brien used a boat metaphor to describe how he “grabbed” his breakthrough despite being unprepared for the role that launched his more than three-decade career.
During a July taping of his SiriusXM podcast Conan O’Brien Needs a Friend, veteran comedian Conan O’Brien shared candid advice about seizing career-defining opportunities, drawing from his own unlikely journey from behind-the-scenes writer to late-night television icon with an estimated net worth of $200 million.
The moment came when an audience member named Billy, a former NBC sales employee, recounted meeting O’Brien at a 1993 cocktail party on the top floor of 30 Rock. “Everyone in the room goes, he is the next big thing?” Billy recalled, asking O’Brien whether he had ever envisioned himself in front of the camera during his writing days.
O’Brien’s response revealed the serendipitous nature of his breakthrough. “I did think about it, but I knew it had to be the right way,” he explained. “But I knew what I wasn’t. I knew I was not a stand-up. I knew that I had something to offer, but I didn’t know where it fit in in the firmament.”
The opportunity arose during what O’Brien described as a “seismic shift in late night” when David Letterman departed NBC for CBS in 1993. The network turned to Saturday Night Live executive producer Lorne Michaels to select a replacement. O’Brien, then writing for The Simpsons after his Emmy-winning stint at SNL from 1988 to 1991, emerged as an unexpected choice.
“Insane events took place that could not have been thought of,” O’Brien said. “Nowadays, they’d never have picked me. Ever. Ever. They would have said, ‘OK, you know, the world is filled with hilarious people who’ve been making things on YouTube for years, and there’s so many possibilities.’ Back then it was, ‘Oh no, who will host the show if Dave’s not hosting it?'”
The selection proved transformative for O’Brien, who urged the audience not to flinch from daunting opportunities.
“When your moment comes, you may not be ready, but you have to take it—and then figure it out on the way,” he said, then later used a vivid metaphor to illustrate his philosophy around taking chances.
“A steel boat is leaving the port, and it’s leaving, leaving, leaving, and you know you have to be on that boat, leap. Now there’s a good chance when I landed on that boat, I hit my chest against the edge of the boat, hit my jaw, fell in the water, almost drowned, grabbed a rope, got dragged along, looked like an idiot, pulled myself up, bleeding, but I got on the boat.”
Despite initial critical skepticism and threats of cancellation, O’Brien’s Late Night became a 16-year success story. He eventually took over The Tonight Show after Jay Leno moved to primetime briefly, though his tenure there was short.
Still, his career resilience proved financially rewarding: when NBC controversially ousted him from The Tonight Show in 2010, he received a $45 million settlement. He quickly rebounded with Conan on TBS, earning an estimated $12 million-$15 million annually until the show ended in 2021.
O’Brien’s business acumen extended beyond television. In 2022, he sold his digital media company Team Coco, which includes his hit podcast and YouTube empire with over 8 billion views, to SiriusXM for $150 million.
“I still wake up some mornings and go, wait a minute, what? I’m at The Simpsons? I’m a writer in a dark room, and then that happened? And it worked? Not right away, but it worked? That’s crazy,” O’Brien said during the July taping.
For this story, Fortune used generative AI to help with an initial draft. An editor verified the accuracy of the information before publishing.
This story was originally featured on Fortune.com
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