Brian Chesky’s Big Bet: How the OpenAI Shakeup Spurred Airbnb’s $200 Million Transformation
According to Brian Chesky, Airbnb’s radical reinvention traces its origins straight back to the 2023 OpenAI leadership coup. On November 17 that year, OpenAI’s board ousted CEO Sam Altman—Chesky’s close friend—and Chesky sprang into action immediately. He publicly defended Altman on X, hopped on urgent calls with Microsoft’s CEO, and threw himself into the center of Altman’s fight to reclaim his role at the AI firm. Five days later, Altman won back his position, and Chesky, still thrumming with adrenaline (“I was completely jacked up,” he recalls), turned his restless mind to his own company: Airbnb.
It was the start of Thanksgiving weekend. Chesky’s extended family had already held their annual turkey gathering a week early, leaving the Airbnb CEO with no holiday plans. He was entirely alone in his sprawling San Francisco apartment, save for his golden retriever, Sophie.
Still wired from the catharsis of the high-stakes corporate rescue, Chesky began typing. His goal: yank the company he co-founded out of its narrow niche as a short-term home rental platform. Chesky often points to Amazon as a blueprint: the retail giant launched as nothing more than an online bookstore before growing into the everything store it is today, and Chesky had long believed Airbnb could follow the same expansion path. For years, though, other priorities blocked the way: untangling systemic safety issues, fighting restrictive regulation, surviving the existential threat of a global pandemic. Now, the company risked being stamped with the term ambitious entrepreneurs fear more than any other: mature.
The OpenChaos had emboldened Chesky to map out his full new vision. If home rentals are just one service Airbnb can offer, why stop there? Chesky’s plan: turn Airbnb into a one-stop platform for booking nearly any local service. While existing apps are siloed into individual niches—food delivery, home maintenance, ride-hailing—Chesky argues Airbnb’s decades of experience curating attractive listings, vetting hosts, and managing crises makes it more trustworthy than competitors, positioning it to become the go-to option for almost anything a user needs.
Moving from room to room—typing frantically at his dining table, on the couch, in bed, and occasionally at his office desk—Chesky mapped out a full redesign of the Airbnb app. The platform now counts 2 billion total users, and Chesky wants them to open the app not just when planning a vacation, but any time they need a portrait photographer, a personal trainer, or a private chef to cook a meal at home. To pull this off, Chesky says Airbnb will need to dramatically strengthen its identity verification processes. He even envisions users relying on their Airbnb profile as a trusted credential, on par with a government-issued ID. If he can successfully transform Airbnb into a full marketplace for in-person services, Chesky believes he will catapult the company from its current nearly $10 billion annual revenue into the exclusive pantheon of global tech giants.
Over the following days, Chesky poured all these ideas into an Evernote document. “I was just moving from room to room pouring out this stream-of-consciousness manifesto, like Jack Kerouac writing On the Road,” he says, referencing the beat classic typed in one frenetic burst on a single roll of teletype paper. “I dug up all my old ideas from 2012 to 2016,” Chesky told me. “I basically said, ‘We’re not just a vacation app—we’re going to be a platform, a community.’” By the end of the first week, he had written roughly 10,000 words, “incomprehensible to anyone but me.” He set to refining the text, and by the time Thanksgiving weekend wrapped, he’d distilled the entire vision down to a tight 1,500-word memo.
After the holiday, Chesky gathered his leadership team in a conference room. Following the Jeff Bezos playbook, he handed out copies of his memo and gave his direct reports time to read it through fully before discussion. “Usually when I share new ideas, people aren’t bought in right away,” he says. “But this time, there wasn’t a lot of pushback. People were really excited. And two years later, we’re executing this exactly, down to the fine details of what I wrote that weekend.”
This month, Airbnb will launch the first phase of its more than $200 million reinvention: a roster of more than 10,000 vendors offering a wide range of services across 260 cities in 30 countries. The launch also revives a failed 2016 experiment from the company: offering customized local activities, branded once again as “Airbnb Experiences.” The second phase, which has no confirmed launch date yet, will build out Airbnb user profiles to be so comprehensive and verified that they are “almost like a passport,” in Chesky’s words. After that, the company will go all-in on artificial intelligence: inspired by his friendship and collaboration with Altman, Chesky hopes to build the ultimate AI agent—a super-concierge that starts by handling customer service, and eventually learns user preferences well enough to plan entire trips, and even other parts of their daily life.
“Brian has been badly underrated as a tech CEO,” Altman says of his friend. “He’s not usually mentioned in the same breath as Larry Page or Bill Gates, but I think he is on a path to build just as big a company.”
That is an ambitious goal—Airbnb is nowhere near the size of those tech behemoths. But Chesky saw a clear need for big change: while Airbnb’s performance is impressive, its current growth rate does not put it on track to reach the trillion-dollar valuations of Google and Microsoft. “I’m 43 and at a crossroads, where I can either be almost done or just getting started,” he tells me. “There’s a scenario where I’m basically finished. Airbnb is very profitable. We’ve kind of, mostly, nailed vacation rentals. But we can do more.”
In early April, I visited Chesky at Airbnb’s sprawling San Francisco headquarters. The relaunch was five weeks away. The second floor, marked with signs warning employees against bringing unauthorized visitors, had been converted into a top-secret, restricted-access command center. Walls were lined with dozens of large poster boards, each dedicated to one city, laid out like a cross between a McKinsey strategy exercise and a fourth-grade geography project. Austin, Texas, was described as “a funky come-as-you-are kind of place,” with a list of “first principles” that included “Outlaw of Texas,” pointing readers toward local food trucks and vintage markets. Another principle was “Live and Alive,” referencing the city’s famous music venues and bat-watching cruises; a third, “Dam Lakes,” highlighted area water sports. Other unsurprising highlights included barbecue, tacos, and two-step dancing. The poster for Paris framed the city as “revolutionary,” defined by slow living and enduring culture.
Chesky strode over to greet me enthusiastically. Dressed in a slim T-shirt that showed off his muscular build, he bounced lightly on his heels with the same jittery energy I remembered from our first meeting back in January 2009. He had just joined Y Combinator’s iconic startup accelerator, and he and his cohort mates were at a party at YC co-founder Paul Graham’s home. (Graham told me back then that he thought Airbnb’s business plan was crazy but was deeply impressed by the founders’ determination.) I mentioned to Chesky that I was headed to Washington, DC, for Barack Obama’s inauguration, and he and his co-founders immediately tried to convince me to book a couch through their service. I declined, but somehow over the next 15 years they sold the idea to 2 billion people—including me—and today Airbnb has a larger market capitalization than Marriott.
Chesky led me into a conference room for a first preview of the new Airbnb app. His engineers and designers have rebuilt the app from scratch, and he twirled a stick of lip balm like a lucky talisman as he walked me through the redesign. Joining us in the room was head of product marketing Jud Coplan, while vice president of design Teo Connor joined the call from London. While most customers think of Airbnb as a travel company, its leadership frames the business as fundamentally a design achievement. That makes sense: both Chesky and co-founder Joe Gebbia are graduates of the Rhode Island School of Design.
Chesky explains that historically, most users only opened the app once or twice a year, so its design was intentionally kept extremely simple. Now, the company is retooling it for far more frequent use. When users open the new app, they will see three core icons that act as gateways to the expanded functionality. Chesky and his team immediately highlighted the cheerful, retro style of the icons: a house for traditional home rentals, a hotel bell for new services, and a Jules Verne-inspired hot-air balloon for Experiences. “We really thought deeply about the metaphor—what was the right visual to express an experience?” says Connor. Once they settled on the balloon, they spent weeks iterating on how much flame should belch from the basket. The icons were drawn by a former Apple designer whose identity Chesky declined to share. “He’s a bit of a secret weapon,” he says.
A less secret weapon is Chesky’s collaboration with legendary former Apple industrial designer Jony Ive. It is no secret that Apple is Chesky’s north star. “Steve Jobs, to me, is like Michelangelo or da Vinci,” he says. Though he never met Jobs, “I feel like I know him deeply, professionally, in a way that few people ever did, in a way that you only possibly could by starting a tech company as a creative person and going on a rocket ship,” Chesky says. By hiring Ive’s LoveFrom firm and working closely with Jobs’ longtime key collaborator, Chesky gets to experience a version of the famous Jobs-Ive creative dynamic. Ive himself does not make that direct comparison, but he does praise Chesky’s natural design instincts. “There are certain tactical things where I hope that sometimes I'm of use to Brian, just as a fellow designer,” Ive says. “But the majority of our work has been around ideas and the way we frame problems and understand opportunities.”
Another core piece of the new app is the user profile page. “You need trust,” Chesky says—trust that relies on fully verifiable identity. Airbnb has been vetting all new vendors, who the company calls “service hosts.” For months, Chesky says, an army of background researchers has been scrutinizing the resumes, licenses, and recommendations of chefs, photographers, manicurists, masseuses, hair stylists, makeup artists, personal trainers, and aestheticians offering spa treatments such as facials and microdermabrasions. Every service host also gets a professional headshot for their profile.
For the next phase—turning all Airbnb user profiles into a trusted primary internet ID—Connor and her team have experimented with cutting-edge technology. She rattles off a list of tools they’ve explored, including biometrics, holograms, and the reactive inks used to deter counterfeiting on official government ID cards. But becoming a private trusted identity provider is far from easy (just ask Facebook), and even Chesky notes that getting governments to accept an Airbnb credential as valid ID is “a stretch goal.”
With so many new users connecting to coordinate services and activities, Airbnb has also upgraded its in-app messaging features. Travelers who join the same experiences can form communities, stay in touch, and even share videos and photos. “I don’t know if I want to call it a social network, because of the stigma associated with it,” says Ari Balogh, Airbnb’s CTO. So the team uses a softer label. “We think of it as a connection platform,” he says. “You’re going to see us build a lot more stuff on top of it, although we’re not an advertising system, thank goodness.” (My own observation: any for-profit company that can host advertising eventually will, but we shall see.)
This brings us to the new services—the heart and soul of this reinvention. The offerings launching now are largely designed to enhance an Airbnb stay with all the premium perks you’d find at a luxury resort, like a real-life White Lotus. It will be interesting to see how the company handles inevitable missteps: cases of food poisoning, bad haircuts, or inappropriate customers. But Airbnb already has 17 years of experience handling similar problems, from dirty sheets to all-night parties in the unit below to hosts that make guests feel unsafe. Eventually, Chesky says, Airbnb will offer “hundreds” of services, ranging from plumbing and house cleaning to car repair, guitar lessons, and tutoring, with Airbnb taking a 15% cut of every booking.
The other key pillar of the reinvention, of course, is Experiences. If the idea sounds familiar, that’s because Airbnb launched a service by that same name with almost the exact same pitch almost a decade ago: special activities for travelers, led by local experts, like architects leading private building tours or chefs teaching guests to fold dumplings.
The first iteration flopped, though Airbnb never formally pulled the plug. Chesky blames early tactical errors: after a big initial splash, the company didn’t follow up with ongoing marketing, and never built a steady pipeline of new experiences. But the real problem, he says, was that it was too far ahead of its time. Now the company has five times as many customers and a full ecosystem to support the effort. “It was our Newton,” says Chesky, referencing Apple’s pre-iPhone handheld device that pioneered the concept but failed commercially. (Another Apple reference, for anyone keeping score.)
Chesky’s team has now lined up more than 22,000 experiences across 650 cities, including a small set of high-profile “Originals” led by top talent: star athletes, Michelin chefs, A-list celebrities. One upcoming offering will let fans take a seat behind the mic in Conan O’Brien’s podcast studio. (Don’t expect your appearance to air.) Learning from the earlier flop, Chesky has planned a steady cadence of these short-term promotional stunts— which the Conan experience ultimately is. “We’re going to have thousands of originals and maybe one day hundreds of thousands—a regular drumbeat of some of the biggest iconic celebrities,” Chesky says.
He walked me through how a user visiting Mexico City could book an experience instantly. “Fun fact—I’ve always dreamed of being a professional wrestler in Mexico. I want to be a luchador!” he told me, then immediately laughed off the comment. Regardless: In an Airbnb experience, he says, you can meet a real luchador, get in the ring with him, and learn some moves. When I asked if you get to keep the mask, Chesky replied, “Probably.” In any case, you’d share your photos with others in your group. (But don’t call it a social network.)
Airbnb’s planned transformation tracks with a second reinvention: that of its leader.
Chesky only formally took the CEO title over his two roughly equal co-founders in 2010; he got the role originally because his personality was more suited to being the company’s public face. Then, in 2011, the company faced its first major public crisis when a host shared a viral horror story about an Airbnb guest who robbed and completely ransacked her home. What wasn’t stolen—the guest broke into a locked closet to grab a passport, cash, and heirloom jewelry—was ravaged and burned in her fireplace. “The death-like smell from the bathroom was frightening,” the host wrote. The story threatened to destroy the warm, person-to-person vibe the company had cultivated, and Airbnb’s initial response was clueless and weak.
Chesky stepped up to become the face of the company and implemented long-overdue safety protocols. Over the next few years, Chesky cemented his position as the clear leader. In 2022 his cofounder Joe Gebbia stepped down from daily duties, though he still sits on the board. (Recently Gebbia has been in the news for his very public participation in DOGE’s effort to restructure the US government. When asked about it at an internal employee Q&A, Chesky said that Gebbia was free to have his own opinions, but they are not the company’s. Chesky did not attend Trump’s inauguration.) The third cofounder, Nathan Blecharczyk, is still with the company, though it’s notable that during my meetings with more than a dozen Airbnb executives, his name only came up when I brought it up.
Chesky was fully in charge during the pandemic, when Airbnb lost 80 percent of its business in eight weeks. He laid off a quarter of the company’s staff. Now that bookings surpass pre-2020 levels, he thinks the company is stronger. And he learned a big lesson: “The pandemic was the turning point of the company,” he says. “My first principle became ‘Don’t apologize for how you want to run your company.’ Most of all you should not apologize for being in the details. The number one thing people want to do is keep you out of the details.”
When Chesky shared these views at a Y Combinator event in 2024, Paul Graham was inspired to write an essay called “Founder Mode.” Graham used Chesky’s story to argue that only the person who created a company knows what is best, and the worst mistake is to listen to career managers who have never built a company of their own. The essay struck a nerve; people were stopping Chesky on the street and yelling “Founder mode!” Someone dropped off a baseball hat for him embroidered with those words; it now sits on a shelf in his conference room.
Chesky, meanwhile, has been deep in the details of this reinvention, itself a classic “founder mode” move. “I did review work before the pandemic, but people kind of hated it. There were negative associations to a CEO reviewing everything; it’s considered micromanaging.” Also, his idol Steve Jobs was famous—infamous?—for his unsparing criticism. Chesky contends that once he went all-in on dishing out criticism, with no sheepishness, people seemed happier. But even if they weren’t, he’d do it anyway. Curious to see how this worked, I arranged to attend a Chesky product review.
Gathered in a conference room, the design and engineering teams presented near-final app tweaks affecting how hosts set up their services. Chesky seemed fairly pleased with what he was seeing—so much so that he apologized to me afterward that I didn’t get to see him lay into his team. Nonetheless, even during this largely positive product review, Chesky babbled a constant stream of minor corrections. The cursor is oddly centered … Those visual cues are a little confusing … We need a subtle drop shadow here … The next line doesn’t seem centered vertically … That address input is pretty awkward … That button looks oddly short, is it supposed to be that short? … That shimmer, do we think we need it? Get rid of it … That top module
