Airbnb Is in Midlife Crisis Mode

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.

After the holiday, Chesky gathered his leadership team into a conference room. He handed the team copies of his memo à la Jeff Bezos and waited as his direct reports took it in. “Usually when I share ideas, people aren’t bought in,” he says. “But this time, there wasn’t a lot of feedback. People were really excited. And two years later, that document will now be executed with an exacting detail to what I wrote.”

This month, Airbnb will launch the first stage of its more than $200 million reinvention: a panoply of more than 10,000 vendors peddling a swath of services in 260 cities in 30 countries. It is also revitalizing an unsuccessful experiment the company began in 2016: offering bespoke local activities, or what it calls “experiences.” The next stage, launch date unspecified, involves making your profile on Airbnb so robust that it’s “almost like a passport,” as Chesky puts it. After that comes a deep immersion into AI: Inspired by his relationship with Altman, Chesky hopes to build the ultimate agent, a super-concierge who starts off handling customer service and eventually knows you well enough to plan your travel and maybe the rest of your life.

“Brian’s 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 as big of a company.”

That’s a stretch—Airbnb is nowhere near the size of those oligarchic powers. But Chesky was feeling the need for big changes; While impressive, Airbnb’s growth rate doesn’t suggest that the company will soon reach the trillion-dollar heights 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 done. Airbnb is very profitable. We've kind of, mostly, nailed vacation rentals. But we can do more.”

In early April, I visited Chesky at the company’s lavish San Francisco headquarters. The relaunch was five weeks away. The second floor—where signs warn employees not to bring visitors—had become a sprawling eyes-only command center. The walls were covered with dozens of large poster boards, each one featuring a city, that read as if a group of McKinsey consultants had tackled a fourth-grade geography assignment. Austin, Texas, was written up as “a funky come-as-you-are kind of place” with a handful of “first principles,” one of which was “Outlaw of Texas,” with pointers to food trucks and vintage markets. Another so-called principle was “Live and Alive,” referring to music venues and bat watching; a third was “Dam Lakes,” referring to various water sports. Other blindingly obvious notations included barbeque, tacos, and the two-step. The Paris poster painted a “revolutionary” city marked by slow living and enduring culture.

Chesky strode up and greeted me enthusiastically. Dressed in a slim T-shirt that exposed his swole physique, he bounced on his heels with a jittery energy that reminded me of the first time I met him, in January 2009. He had just joined Y Combinator’s famous program for startups, and he and his classmates were at a party at the home of YC cofounder Paul Graham. (Graham told me then that he thought Airbnb’s business plan was crazy but was impressed by their determination.) I mentioned to Chesky that I was headed to Washington, DC, for Barack Obama’s inauguration, and he and his cofounders immediately tried to convince me to use their service to sleep on someone’s couch. I declined, but somehow over the next 15 years they managed to sell the idea to 2 billion people, including me, and now the company has a market cap worth more than Marriott.

Chesky ushers me into a conference room to get a preview of the new Airbnb app. His engineers and designers have rebuilt the app from scratch, and he waves around a stick of lip balm as a talisman as he talks me through the redesign. Also in the room is his product marketing head, Jud Coplan, while his vice president of design, Teo Connor, Zooms in from London. While customers likely think of Airbnb as a travel company, its leaders view the operation as an achievement in design. Which makes sense; both Chesky and his cofounder Joe Gebbia were students at the Rhode Island School of Design.

Chesky explains that historically, people used Airbnb only once or twice a year, so its design had to be exceptionally simple. Now the company is retooling for more frequent access. Open the app, and you see a trio of icons that act as gateways to the expanded functions. Within minutes Chesky and his lieutenants are applauding the cheery, retro style of the icons—a house for traditional rentals, a hotel bell for services, and a Jules Verne-ish hot-air balloon representing activities. “We really thought deeply about the metaphor—what was the right visual to express an experience?” says Connor. Once they decided on the balloon, they drilled into how much fire should belch from the basket. The icons were drawn by a former Apple designer whose name Chesky would not divulge. “He’s a bit of a secret weapon,” he says.

A less-secret weapon is Chesky’s collaboration with the iconic, also ex-Apple, industrial designer Jony Ive. Chesky’s north star, it should be said, is Apple. “Steve Jobs, to me, is like Michelangelo or da Vinci,” he says. Despite never meeting 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 company and working with Jobs’ key collaborator, Chesky gets a taste of the famous Jobs/Ive dynamic. Ive himself doesn’t make that comparison, but he does praise Chesky’s design chops. “There are certain tactical things where I hope that sometimes I'm of use to Brian, just as 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 key part of the app is the profile page. “You need trust,” Chesky says—meaning a verifiable identity. Airbnb has been vetting the new vendors, which it calls “service hosts.” For months, Chesky says, an army of background researchers has been scrutinizing the résumés, licenses, and recommendations of chefs, photographers, manicurists, masseuses, hair stylists, makeup artists, personal trainers, and aestheticians who provide spa treatments such as facials and microdermabrasions. They’re all being professionally photographed.

For the next phase—turning Airbnb’s user profiles into a primary internet ID—Connor and her team have engaged in some far-out experimentation. She rattles off a list of technologies they’ve been exploring, including biometrics, holograms, and the reactive inks used to deter counterfeiting on official ID cards. But it’s far from easy to become a private identity utility (hello, Facebook), and even Chesky notes that getting governments to accept an Airbnb credential to verify identity is “a stretch goal.”

Now that a whole slew of people will have new reasons to chat with each other and coordinate plans, Airbnb has also enhanced its messaging functions. Fellow travelers who share experiences can form communities, stay in touch, 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 they employ a fuzzier term. “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 is that any for-profit company that can host advertising will, but whatever.)

This brings us to the services—the heart and soul of this reinvention. Those now on offer seem designed to augment an Airbnb stay with all the stuff that drives up your bill at a luxury resort, like a DIY White Lotus. It will be interesting to see how the company handles the inevitable cases of food poisoning or bad haircuts (and skeezy customers), but Airbnb can draw on its 17 years of experience with dirty sheets, all-night discos on the ground floor, or a host who is literally terrorizing you. Eventually, Chesky says, Airbnb will offer “hundreds” of services, perhaps as far-ranging as plumbing, cleaning, car repair, guitar lessons, and tutoring, and then take its 15 percent fee.

The other key feature of the company’s reinvention, of course, is Experiences. If the idea sounds familiar, that’s because Airbnb launched a service by that name almost a decade ago, with pretty much the same pitch: special activities for travelers, like architects leading tours of buildings or chefs showing people how to fold dumplings.

It flopped, although Airbnb never formally pulled the plug. Chesky’s excuses include tactical errors: After a big initial splash, the company didn’t follow up with more marketing, and it didn’t establish a strong flow of new experiences. But the big reason, he says, was that it was too early. Now the company has five times as many customers and an ecosystem to support the effort. “It was like our Newton,” says Chesky, referring to Apple’s handheld device that predated the iPhone. (Another Apple reference, for those keeping score.)

Chesky’s crew has arranged for more than 22,000 experiences in 650 cities, including a smattering of so-called “originals,” with people at the top of their field—star athletes, Michelin chefs, famous celebrities. In the pipeline is Conan O’Brien selling a perch behind a mic in his podcast studio. (Don’t expect it to air.) Taking a lesson from his earlier flop, Chesky has planned a steady cadence of these short-term promotional stunts, which, of course, is what 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 shows me how someone could take a trip to, say, Mexico City and book experiences instantly. “Fun fact—I’ve always dreamed of being a professional wrestler in Mexico. I want to be a luchador!” he tells me, then immediately regrets it. Regardless: In an Airbnb experience, he says, you can meet a real luchador, get in the ring with him, and learn some moves. Can you keep the mask?

“Probably,” says Chesky. In any case, you’d share the photos with others in your group. (But don’t call it a social network.)

Airbnb’s planned transformation tracks with another reinvention: that of its leader.

Chesky had originally taken the title of CEO over his two pretty-much equal cofounders because his personality was more forward facing—it wasn’t even formalized until 2010. But then, in 2011, the company had its first real crisis when a host publicly shared a horror story about how an Airbnb guest from deep, deep hell pillaged and trashed her home. What wasn’t stolen—the customer broke into a locked closet to grab a passport, cash, and heirloom jewelry—was ravaged and burned in the fireplace. “The death-like smell from the bathroom was frightening,” wrote the host. The story threatened to destroy the cheerful person-to-person vibe the company had cultivated. It didn’t help that Airbnb’s initial response was clueless and weak.

Chesky stepped up to become the face of the company and instituted overdue safety protocols. Over the next few years, Chesky cemented his alpha status. 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 remaking of the US government. When asked about it at a Q and A session with employees, 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 as I sat in meetings with over a dozen executives, the only time his name came up was when I mentioned it.

Chesky was totally in charge during the pandemic, when Airbnb lost 80 percent of its business in eight weeks. He laid off a quarter of the 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 some of 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 management types who haven’t built 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 with those words; it now sits on a shelf in his conference room.

Chesky, meanwhile, has been deep in the details, especially on this reinvention, itself kind of a classic founder 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 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 go animal with his underlings. Nonetheless, even during this lovefest of a 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 doesn’t make sense … We need to rewrite all the copy on this page … I think we need a better empty state … That title’s not clear …

The group shuffles out satisfied and a bit stunned that they got away so easy. But when I meet Chesky a day later to sum things up, he tells me that I’d just missed a spicier product review. Then he gets serious, explaining what the reinvention means to him. “I felt a little bit like the vacation rental guy,” he says. “Like we as a company are a little underestimated.” He brings up Apple again, saying that both companies embody the idea that a business relationship can generate emotion. “My ambition is kind of like the ambition of an artist and designer,” he says.

At that point Chesky gets a little woo. “Magic, in hindsight, is not technology,” he says as he reflects on Apple’s wizardry. What he’s realized is that magic lies in forging connections with those who offer you a bed, a microdermabrasion, a sparring match in a lucha libre ring. “The magic that is timeless is, like, the stuff you remember at the end of your life.”

He lets that sit for a minute. Then he puts a cap on that insight, sounding less like a CEO than a life coach. “I’ve never had a dream with a device in it,” he says. Leave it to the subconscious to highlight what matters. That said, his day dreams certainly involve a new kind of device. In his off hours he’s helping with a secret project headed by his friends Altman and Ive to create a device that Altman says is the next step beyond computers. (“This is not theoretical memo-swapping,” Altman tells me. “We’re hard at work on it, prototyping.”)

But that’s somewhere off in the future. In the realm of products that actually exist in the world, Chesky will have to face competition from dozens of domain leaders including Yelp, Instacart, DoorDash, Ticketmaster, Hotels.com, Tinder, OpenTable, and Craigslist, to name but a few. You can probably add Apple, Meta, and Microsoft, since Chesky wants Airbnb to be a universal credential and what certainly looks like a social network. Even Steve Jobs might have blinked at taking on that crowd all at once.

Correction: 5/14/2025, 3:10 pm EDT: The article has been corrected to reflect the year Joe Gebbia stepped down from daily duties.

Images styled by Jillian Knox.
Featuring: Liv Skinner, Liv Well and Francesca Lopez, Zinnia Wildflower Bakehouse

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