You are an entrepreneur who has achieved the impossible. You have disrupted an entire sector of the economy and practically invented a new one. Most startups fail, but you have built yours into a billion-dollar company—a genus so scarce that it’s called a unicorn. Your brand has become a transitive verb. What do you do now? Stop growing? Stop disrupting? Of course not. Winners don’t quit. They find new ways to win.
Brian Chesky, the co-founder and C.E.O. of Airbnb, was in SoHo the other day, standing near the cash register at the Housing Works Bookstore. In addition to being a forty-three-year-old multibillionaire, he is among the swolest of the swole C.E.O.s, with a swoop of dark curly hair and lats that make Jeff Bezos look like a featherweight. There was a steady rain, but Chesky walked outside in pleated slacks and a form-fitting T-shirt, risking his suède Celine sneakers. “Unlike a lot of tech companies, our business exists in the real world,” he said. “To launch something the right way, you need to get out into the community.”
He was starting what he called “the next chapter of the company, an evolution I’ve been thinking about for a long time.” (Wired: “Airbnb Is in Midlife Crisis Mode.”) Since 2007, travellers have been able to Airbnb a place to stay; now they can also Airbnb a Service (haircut, massage) or an Experience (cooking class, Jet Ski outing). Chesky was in SoHo to have an Experience.
He had just arrived from California, where he lives alone (when he’s not renting out his guest room on the app). Next, he was on his way to Paris, Berlin, Milan, Rome, Seoul, and Tokyo, sampling new wares along the way. The Experiences section of the Airbnb app was still in beta mode, and the New York selection was slim (“Make beats with a New York DJ”; “Catacombs by Candlelight”). Chesky was going on a walking tour of SoHo, focussed on architectural photography.
“I’m out in these streets in all kinds of weather,” the photographer Ethan Barber, who was leading the tour, said. “The only compromise I’ll be making today, because of the rain, is I’ll be shooting iPhone-only.” Walking backward, his glasses fogging, Barber headed to the first destination, a cast-iron building on the corner of Prince and Greene. He was used to leading groups, but this one was a private demo for Chesky. Chesky, however, travels with an entourage: press attachés, a couple of executives, and a guy named Chase, whose job is to fill Chesky’s social-media accounts with humanizing photos of the boss. A black S.U.V.—driver, plus private security—kept pace with the group.
Cartoon by Jared Nangle
Someone handed Chesky an umbrella; he waved it off, walked half a block, then changed his mind and took it. At the first stop, Barber pointed to the building—a French Renaissance landmark from 1883, now a Ralph Lauren store—and located his favorite spot to shoot from, marked by a wad of chewing gum ground into the sidewalk. Chesky stood next to the gum, finished tapping out a text, then held his iPhone in landscape mode and took a few snaps of the building while Chase took snaps of him.
“This could be cool,” Chase said, reviewing a moody black-and-white shot of Chesky. “Not for grid, but for Stories, maybe.”
Chesky went back to texting, and Barber moved along—to an Isabel Marant store on Broome and then to a former Isaac Mizrahi warehouse at 102 Wooster. Between texts, Chesky continued his pitch for the Airbnb redesign. “Most apps want you down here, in the phone,” he said, bending his neck down. “Our purpose”—head up, shoulders back—“is to get you out and about, making memories.”
The final stop was a walk-through of an artist’s foundation. Two women guiding the tour asked the guests to refrain from indoor photography. Everyone complied, except Chesky, who may or may not have heard the instruction. “I’m redoing my house, and I would be so into a wood floor like this,” he said, taking a video and sending it to his designer. “I want it to have that artist feel.”
Throughout the space, there were places for the artist to rest—a daybed, an East African headrest, a wooden platform holding two mattresses and a sculpture. Naturally, the discussion turned to how much the building might rent for on Airbnb. It wasn’t a serious idea, but it also wasn’t a radical one—Airbnb once offered an overnight stay at the Louvre, and another at the Musée d’Orsay. This building could be similarly enticing, the group mused, if not even more so. One of the curators said, with a tight smile, “Thanks, but it’s not available.” ♦
