Some nights, Brian Chesky wakes up with his heart pounding. It’s a familiar feeling—one that he’s had since the early days of Airbnb, the online lodging company he co-founded nearly 10 years ago. Back then, his fears were not unlike those that plague most entrepreneurs: he worried about running out of money, building a product no one wanted, his company going bust. There is little danger of that now. Airbnb, worth $30 billion, operates in every place in the world except Iran, Syria, Sudan, Crimea, and North Korea. Roughly 100 million people—including Beyoncé, Kendall Jenner, and Gwyneth Paltrow—have used the site. And Chesky, at 35 years old, is a billionaire and one of the most powerful C.E.O.’s in Silicon Valley.

Still, in the quiet dark hours, when there are no e-mails, no meetings, no calls or other distractions, the chest tightening returns and wakes him. Only now his anxieties, while just as existential, are more open-ended and philosophical. “If we don’t grow past what we originally invented, what led to your success leads to your death,” Chesky told me. It was a bright morning in late September, and Chesky and I were sitting in a yurt in Topanga Canyon, west of Los Angeles. There was no cell-phone service, leaving Chesky uncharacteristically out of touch with Airbnb headquarters, in San Francisco. “It’s a Friday. God knows what’s happening right now,” he said. Already that week, news had leaked that Google Capital was leading a new round of investment in the site, the city of Barcelona had threatened Airbnb hosts with new enforcement measures, and Britain’s top property court had ruled that one London woman was breaking the law by renting out her apartment on Airbnb.

Chesky had intentionally cut himself off from the world to focus on a service that he believes is the future of his company. Airbnb Trips, officially launched in November, offers travelers a series of excursions and adventures—and pushes Airbnb well past its couch-surfing origins. Chesky had invited me to tag along as he personally tested an experience called “The TV Writer’s Journey.” He and a small team of Airbnb executives had recruited some professional television writers to design a three-day tour that would give travelers a taste of what it is like to live and work in L.A. This is sort of the Airbnb version of the NBC studio tour—offbeat, unpolished, and probably not for Grandma. (The yurt was home to one of the writers; its toilet was an outhouse over a compost heap.) It was day two, and travelers were simulating what happens in a TV writers’ room.

“I like the idea that there is this alternative universe,” a young woman in jean shorts said. She’d signed up for the trip on a whim and had no idea who Chesky was—other than that he was a big science-fiction fan who watched Stranger Things on Netflix and 11.22.63on Hulu. The plot they’d hatched was arguably wilder than those of the two shows. It involved a woman using some kind of space-time transporter on her wedding day to enter a parallel universe where she was a stand-up comedian—sort of Runaway Bride meets Doctor Strange meets Inside Amy Schumer. “What are the chances this could get made into a real TV show?,” Chesky asked in all sincerity. Inside the yurt, for a few hours at least, he was just another guy on a trip.

THE BIG PICTURE

Chesky (bottom, center) poses in a conference room at Airbnb headquarters. Photograph by Art Streiber.

Two years ago Chesky quietly pulled back from his day-to-day duties running Airbnb’s home-rental business to focus on building these new excursions. If the service takes off, it could be what transforms Airbnb from a one-trick Web site into a platform (in Silicon Valley parlance) that eventually will allow individuals to sell all sorts of services, such as guided tours, musical outings, even car rides, which could put Airbnb in competition with Uber. The first batch of Airbnb Trips will include lessons from a samurai master in Japan, training with long-distance runners in Kenya, and surfing with a local pro in Malibu.