(2025-05-13) Levy Brian Chesky Lost His Mind One Night, and Now He's Relaunching AirBnb As An Everything App

Steven Levy: Brian Chesky Lost His Mind One Night—and Now He's Relaunching Airbnb as an Everything App. 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.... “I was so jacked up,” he says—turned his buzzing mind to his own company, Airbnb.... He wanted to bust the company he’d cofounded out of its pigeonhole of short-term home rentals. I guess this was made possible by (2023-09-09) Itamar Gilad On Linkedin Why Did Airbnb Kill Product Management.

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.

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.

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.

we’re going to be a platform, a community.’”

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.

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

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.

“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.”

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.

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.

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.

icons—a house for traditional rentals, a hotel bell for services, and a Jules Verne-ish hot-air balloon representing activities

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.”

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

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.

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.

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

It flopped, although Airbnb never formally pulled the plug... he says, was that it was too early.

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.

Chesky has planned a steady cadence of these short-term promotional stunts,

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

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

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.’

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

Chesky, meanwhile, has been deep in the details, especially on this reinvention, itself kind of a classic founder move

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

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.

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.”

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.

Jason Kehe, Wired Features Editor: The insane Amazonification of Airbnb

Do people still like Airbnb? Do people still use Airbnb? I mean, obviously they do, I’m one of them, but the last few times, I’ve ended up in the most generic-looking “homes” imaginable—in quotes because they never actually qualify. Homes are lived-in, individual, and that was always the promise of the app: to sleep in someone else’s bed. If I wanted fake comfort, I’d book a hotel.

So I was confused when Steven Levy, our most veteran writer, said he wanted to do a Big Story on, of all the companies to care about in 2025, Airbnb. But they’re so lame! I shouted. Then Steven explained why: The company was planning to “relaunch” as … something else. Something bigger. I had to admit to a certain curiosity. What did that mean?

I’ll tell you what it doesn’t mean: Airbnb is not returning to its humble, real-people roots. But of course it’s not. Ours is a world where being good at a single thing is not only not enough—it’s figured as immoral. To succeed obliges one to succeed more, lest society be deprived of the fruits of one’s genius. Right?

Kyle Chayka: Airbnb's relaunch and the texture era of design

The housing rental platform is becoming a high-touch lifestyle app, and crystallizing a new design trend in the process. But can any trend survive AI replication?

Airbnb recently rebooted itself. In its annual “summer release” on May 13, the co-founder and CEO Brian Chesky essentially announced a new era for the app.

Chesky has been presenting this as a kind of personal, mind-blowing epiphany, as recounted in a slyly mocking Wired profile, complete with glamorous CEO photo shoot. Chesky compared himself to Jack Kerouac.

Experiences have already failed for Airbnb once. It turns out it’s harder to productize and scale human-to-human interaction than renting out empty houses.

What’s more interesting than the pivot is the aesthetic. Airbnb has always been a design-forward company, its brand as prominent as its tech. After the relaunch, its icons are softly rounded pictographs,

As Chesky later posted on X, it’s an intentional shift away from generic geometric designs and toward texture and form

“Skeuomorphism” is the design strategy of making digital objects look like what they refer to in physical space. It was unfashionable for a while, but now it’s back.

Carly Ayres wrote an insightful newsletter, ”why everyone is suddenly so thirsty for designers,” about the shift: Flat design dominated the last decade. Its aesthetic—clean, quiet, systematized—mapped neatly to the metrics-driven culture of post-2010s tech.

Care is about intention, patience, and impact. It’s the opposite of scalability; scalability is when you don’t care, when you think that the same user experience should be applied to everyone on earth. Airbnb was a vector of that kind of scalability as it popularized the generic international minimalism of AirSpace, a flattening of aesthetic taste. Care, however, is against flattening. Airbnb now has to reinforce a sense of intimacy and specificity because it’s trying to promote (and sell) person-to-person interaction, IRL.

Which makes for a quandary: Do you need more design to show that you care, or less to show that it’s real? I’ll be watching for further examples of hyper-textured design, but I’ll also be slightly suspicious of it, looking for something that can’t be faked.

We’ll see more tech companies follow in Airbnb’s wake; a design entrepreneur on X already demonstrated how he used AI to replicate the skeuomorphic, rounded, animated icons, effortlessly whipping up a coffee machine. Care is also the opposite of automation.

Drew Austin: the Airbnb CEO was left behind by the 2020s vibe shift and is the last guy in Silicon Valley trying to do ZIRPy Uber-for-X stuff instead of pivoting to culture war and military drone technology."