When Conan O’Brien signed his latest deal with TBS, he didn’t just agree to keep his late-night talk show on the air for another four years. In addition to hosting “Conan,” he promised to create digital content, podcasting, live tours, and other forms of entertainment.

It wasn’t just an attempt to make more money or keep O’Brien creatively fulfilled after more than two decades on the air, although it has proved to be both of those things too. It was also an acknowledgment that late-night television has changed. Instead of tuning into Jay or Dave or Johnny as part of an evening ritual, most Americans prefer to consume their comedy shows in easily digestible bites the next morning on YouTube.

“More and more with late-night TV, it’s going to be rare that someone starts watching and then watches for the entire show unless they fall asleep in front of the set,” says O’Brien. “It used to be late-night shows were the last thing people saw and Johnny Carson was putting the nation to bed at night and that was this titanic responsibility. I don’t have any illusions that I’m doing that. That’s not what these shows are anymore and you can’t waste time being nostalgic about it.”

Read Variety’s cover story about how Conan O’Brien and other top hosts are driving the podcast revolution

Instead, O’Brien and his company Conaco, LLC set about figuring out the best way to connect with the comedian’s younger and digitally savvy fans at a time when late-night viewership is shrinking and audiences are abandoning cable for streaming. They started a series of travel specials that have charted the globe, allowing the flame-haired comic to cracked wise with locals in Israel, Haiti, and South Korea. They put together a multi-city live tour, giving O’Brien a chance to do standup with the likes of Deon Cole, Laurie Kilmartin, and Marina Franklin. And they planted a flag in the fast growing world of podcasting with the November launch of “Conan O’Brien Needs a Friend,” an interview show that’s garnered critical raves and a massive audience.

“We want to stay ahead of the curve and be in all those spaces where our audience is going,” says Jeff Ross, executive producer of “Conan.” “We’d been doing things the same way for the last 20-something years and over the last year and a half we decided to shake it up and have some fun.”

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There’s another important stylistic difference between O’Brien and most of the late-night television gang. Unlike Seth Meyers or Stephen Colbert who routinely lampoon President Donald Trump, O’Brien steers largely clear of inside the Beltway zingers.

“Our sensibility is not political,” says Ross. “It’s more of a funny, sillier kind of thing. We sort of went the other way.”

Some of these projects, Ross admits, are loss leaders. Others, such as “Conan O’Brien Needs a Friend,” turn a profit. In fact, the podcast has been such a big hit that it’s galvanized Conaco to launch a spin-off interview show with O’Brien’s longtime sidekick Andy Richter, as well as to create a multi-episode series with O’Brien and master impressionist Dana Carvey. O’Brien’s team recently extended a co-production and distribution deal with podcasting company Midroll that will keep “Conan O’Brien Needs a Friend” recording for two additional years and at least 72 more episodes. The pact is in the mid-seven figures.

“Podcasting has been a big business success — a brand success – and you always feel hokey even saying that,” says O’Brien. “Because it can sound like [here O’Brien slips into an old timey, clipped, 1920s voice] ‘This has been a terrific move for Conaco enterprises gentleman.’ It’s not like everyone lights up our cigars and we’ve pulled off some caper. It’s funny because I never foresaw any of it.”

In fact, O’Brien had to be convinced by his team that he’d take to podcasting. For support, he insisted that his longtime assistant and occasional on-air foil Sona Movsesian serve as co-host. Producer Matt Gourley was later elevated to co-host, as well. Planning was minimal, although O’Brien and Movsesian did record test shows with Wanda Sykes and Jack McBrayer before officially premiering with an interview with Will Ferrell.

“We just sort of got together and riffed,” says Movsesian. “We just jumped into the deep end and saw what happened.”

Very quickly, O’Brien discovered he had a natural affinity for podcasting. He liked the fact that he could talk to his guests in a looser fashion without having to worry about cutting to commercial, landing a punchline, or giving them ample time to hawk their latest movie. And, though the conceit of O’Brien auditioning friends was just that, a conceit, he’s found himself getting closer to his guests. He was particularly moved by a sit-down with Ben Stiller, a former colleague from O’Brien’s stint writing for “Saturday Night Live,” who admitted to feeling insecure about his work and accomplishments.

“When he left the room, I thought that’s the best conversation that Ben and I have ever had,” says O’Brien. “The title of the podcast was meant to be just kind of a joke, but I swear to God, I’m getting closer to people. It’s been a gift.”

The host’s genuine enthusiasm for the format is part of the reason the show is working. Now that brand names are starting to advertise on podcasts and subscription services are launching, the platform has become much more lucrative. But not every celeb is cut out for this new kind of audio entertainment.

“I’ve heard a lot of podcasts done as a cash grab,” says Gourley. “He may joke that Sona and I are driving Bentleys and embezzling money from the show, but he’s not doing this to get rich. He’s doing it for the love of the game. He gets to be himself and play in this entirely new sandbox.”

The biggest obstacle confronting this spirit of persistent experimentation is time. Where O’Brien was once doing one job, hosting a late-night show, he’s now juggling three or four.

“He’s pretty maxed out,” says Ross. “Conan may do some other things, but we’re running out of time in the day.”

Other Conaco podcasts, such as “Frontier Tween” and “Smartr,” two scripted shows that the company will produce for subscription network Luminary, will feature different cast members. O’Brien’s involvement will be mostly limited to creative input.

In a nod to the changing way that late shows are being consumed, Conaco has begun to beef up the comic’s digital archive. In 2018, O’Brien’s team reached an agreement with NBC, his former broadcasting home, to make every episode of “Late Night with Conan O’Brien” available digitally. The pact, which spans some 2,725 episodes between 1993 and 2009, does not extend to O’Brien’s aborted run as the host of “The Tonight Show.”

Ultimately, O’Brien is hoping that these various “brand extensions” will overlap, foreseeing a time when he records a podcast with a guest who lives in a country where he’s doing a travel show, for instance. That kind of overlap between platforms happened recently when O’Brien enlisted Movsesian to fill in as a guest on “Conan.” It was an emergency booking. Kumail Nanjiani was forced to cancel at the last minute after shooting went over on “Silicon Valley.” The clip, in which the audience loudly chants along while urging O’Brien to buy his assistant a house, went viral. A subsequent episode of “Conan O’Brien Needs a Friend,” in which O’Brien and Nanjiani discussed the cancellation seen round the television universe, was among the show’s most popular.

“That was such a moment for us,” says O’Brien. “It’s a perfect example of cross pollination. When my producers came to me and said Kumail couldn’t come, they said there was a chance we can get so and so. I thought forget it. Lets have Sona. Her supreme talent in life is she’s always herself. Because I’ve grown so comfortable working with her on the podcast, I knew that she could do it.”

As for Movsesian, she’s not eager to repeat her turn on the late-night stage.

“It shouldn’t happen again,” she says. “I did well because the expectations were very low. When you put a random assistant on camera and they don’t throw up on themselves, you think they did a good job. People were being very kind.”