As Brian Chesky tells it, the reinvention of Airbnb started with the coup at OpenAI. On November 17, 2023, the board of OpenAI fired company CEO Sam Altman. His friend Chesky leapt into action—publicly defending his pal on X, getting on the phone with Microsoft’s CEO, and throwing himself into the thick of Altman’s battle to retake OpenAI. Five days later Altman prevailed, and Chesky—“I was so jacked up,” he says—turned his buzzing mind to his own company, Airbnb.
Thanksgiving weekend was beginning. The Chesky extended family had already held their turkey get-together a week earlier, and the Airbnb CEO had no holiday plan. He was completely alone in his sprawling San Francisco apartment except for Sophie, his golden retriever.
Still wired out of his mind from the cathartic corporate rescue, Chesky began to write. He wanted to bust the company he’d cofounded out of its pigeonhole of short-term home rentals. Amazon, he was fond of pointing out, was first an online bookstore before it became the everything store. Chesky had long believed that Airbnb should expand in a similar way. But things kept getting in the way—dealing with safety issues, fighting regulation, coping with the existential crisis of a global pandemic. The company was in danger of being tagged with the word that ambitious entrepreneurs dread like the plague: mature.
Now Chesky was emboldened to lay out his vision. Home rentals are simply a service, so why stop there? Airbnb could be the platform for booking all sorts of services. While other apps cover specific sectors—food delivery, home maintenance, car rides—Chesky figured that Airbnb’s experience in attractively displaying homes, vetting hosts, and responding to crises could make it more trustworthy than competitors and therefore the go-to option for virtually anything.
In a frantic typing spree at the dining room table, on the couch, the bed, and at times in his office, Chesky specced out how he would redesign the Airbnb app. Its users—now at 2 billion—would open up the app not only at vacation time but whenever they needed to find a portrait photographer, a personal trainer, or someone to cook their meals. Chesky reasoned that Airbnb would need to significantly strengthen its identity verification. He even thought he could get people to use the app as a credential, something as respected as a government-issued ID. If he could transform Airbnb into a storefront for real-world services, Chesky thought, he’d catapult his company from a nearly $10-billion-a-year business into one that boasted membership in tech’s pantheon.
Over the next few days, Chesky spilled these thoughts into an Evernote document. “I was basically going from room to room just pouring out this stream-of-consciousness manifesto, like Jack Kerouac writing On the Road,” he says, referring to the frenetically produced single roll of teletype paper that catalyzed the beat movement. “I dusted off all my ideas from 2012 to 2016,” Chesky tells me. “I basically said, ‘We’re not just a vacation app—we’re going to be a platform, a community.’” By Friday he had around 10,000 words, “incomprehensible to anyone but me.” He began to refine it, and by the time the weekend was over, Chesky had distilled his document down to 1,500 words.
