He revolutionized travel. Can Airbnb’s founder redesign your entire life?

When Barack Obama became president of the United States, the company was barely a speck on the map. By the time he left office in 2017, Airbnb was both a verb and noun. It had become such a ubiquitous part of American life that when he escaped Washington and took a trip to Hawaii, he found himself checking into an Airbnb instead of a hotel. The next time he Airbnb’d was a few years later, when the Obamas celebrated their wedding anniversary by retracing their honeymoon with a stop in Carmel, California.

“Michelle was happy, and as a consequence, I was happy," Obama tells me.

His review? “I think I gave it five stars," he says. “I was very satisfied."

The former president is one of the hundreds of millions of people who have used Airbnb billions of times for family vacations and weekend getaways all over the planet. And if you close your eyes and imagine the dream Airbnb, it might look something like the house in the Dolores Heights neighborhood of San Francisco where I went to meet Brian Chesky, the co-founder and chief executive officer of the company and one of the tech industry’s most influential figures.

As it happens, this is Chesky’s home. He shares it with Sophie and Chloe—his golden retrievers. It has Aesop products in the bathrooms, tastefully curated bookshelves around a fully stocked bar and spectacularly panoramic views of the city. He occasionally rents his guest bedroom on Airbnb, promising freshly baked chocolate chip cookies for guests. (His trick: Double the vanilla extract.) When he gives me a tour one sunny afternoon in March, he proudly shows off his own framed drawings on the walls and flips through a notebook full of sketches.

Over the past few years, Chesky had been sketching out a new direction for Airbnb. And for the past several months, the hospitable billionaire has been preparing for what he anticipates will be the most important day in the company’s history. The day has become known inside the company as M13, as in May 13, when he would take the stage to announce that Airbnb is expanding from homes into services and experiences.

“Basically," Chesky says, “it’s the Airbnb of anything."

From now on, you can Airbnb more than just the physical space of a traditional Airbnb. You can Airbnb a Michelin-starred chef to make dinner in your kitchen, and you can Airbnb a glam team to do your hair and makeup for that dinner party. While in Paris, you can Airbnb a tour of Notre-Dame with the architect who helped restore the cathedral. In Tokyo, you can Airbnb a matcha tasting with a tea farmer. In Mexico City, you can Airbnb time in the ring with a lucha libre wrestler. And then you can Airbnb the massage you’ll need the next day.

In other words, Airbnb is going from the business of home-sharing and short-term rentals to the business of everything.

It’s the sort of bet that only Brian Chesky could have made—and not just because he’s a restless leader who stays up late making big plans while also obsessing over every last little detail. It’s also because he believes only a founder has what it takes to find the way to the future.

ONE NIGHT LAST FALL, Chesky, 43, was invited to speak at an event hosted by Y Combinator, the famed accelerator that incubated successful tech companies like DoorDash, Coinbase and Airbnb. He wasn’t on the official program and didn’t bother telling anyone inside his own company before he drove to Sonoma. He figured nobody outside the room of young entrepreneurs would hear his talk. But what he said would soon echo across Silicon Valley.

The ideas that came pouring out of him that night had been rattling around his brain for the past five years. During that time, he’d become convinced that the conventional wisdom for how to run a company wasn’t all that wise. In fact, most of it was simply wrong. Chesky felt that he’d been given the right advice for how to start a company. When he tried to scale that same company, he was told to hire great people and trust them to do their jobs. But the more he thought about it, the less he thought it worked. And it definitely wasn’t working for him. So he came up with another way.

The following week, Y Combinator co-founder Paul Graham published an essay that came up with a name for Chesky’s management philosophy: founder mode.

What exactly is founder mode? After the talk, Chesky sketched out 116 bullet points that he eventually whittled down to roughly a dozen core principles. At his dining room table, he reached for the reading glasses he’s needed since turning 40 and began reciting them off his phone.

“Don’t apologize for how you want to run your company," he said.

Live in the details, he went on. Stay small. Stay flat. Stay functional. Have as few people and as few layers as possible for as long as possible. Hire your direct reports—and their direct reports. Speak for yourself. Review all the work. Lean into a crisis. Rethink everything from board structure to marketing strategy. Focus the company around product releases. And founders shouldn’t just be chief executive officers. They should also be chief product officers.

Long before he put any of this in writing, his closest friends lived through the rough drafts. The only part of founder mode they didn’t recognize was the name.

“I was actually just calling it Brian mode," says Whitney Wolfe Herd, the founder and CEO of the dating platform Bumble.

Wolfe Herd met Chesky at a strange time in her life. The first time they had dinner, she had just stepped down as the CEO of Bumble. Over the next year, he would coach her to trust her instincts and operate with the conviction that she had when she first decided to build something from nothing. “He always said to me that being a public-company CEO doesn’t have to be miserable," she says, “and I thought he was crazy." But she came around. By the time she returned to Bumble this year, she felt like an entirely different person. “He really taught me how to be a CEO again," she says.

As he was mentoring other founders, he was going full founder mode himself.

When you open the new Airbnb app, you’ll find three icons across the top navigation bar: homes, experiences, services. The design of each was personally approved by Chesky—right down to the hue of the hot-air balloon for experiences. Before he picked the button that you’ll scroll past without a second thought, he looked at no fewer than 100 options. Should it even be a hot-air balloon? Or a surfer? Should it be in color? What color? Blue? No, red. But how red?

Chesky applies the same analytical rigor and maniacal attention to every detail in his life, including the black shirts in his closet. On the day we met, he wore a black shirt with frayed sleeves that looked almost as though the beefy former competitive bodybuilder had ripped them himself. (“No, this comes ripped," he clarified. “It’s a Rick Owens.") The unveiling of the new Airbnb was months away, but he was already thinking about which black shirt to wear.

“There’s going to be a really big decision I have to make: short sleeve or long sleeve?" he says. “And then the second decision is what shade of black. And then the third decision is what sheen of black. And then the fourth decision is how thick…."

Of course, there are control freaks and micromanagers in every industry, and the cult of the founder is especially alluring in tech. But in all the fervor over founder mode, Chesky says people got one part very wrong. “It’s not about being an asshole," he said. “I would argue that if you want to do something for the long term, people have to enjoy the experience of working for you."

When I asked him for names that personify founder mode, the first he mentioned were Steve Jobs and Walt Disney. “I don’t want to ever put myself on the same level," he said. “I’m more like a disciple. I’m more like a painter who studies Michelangelo. I’m not ever saying I’m going to be Michelangelo, but I believe in that school of thought."

He goes on to say that he admires Jobs and Disney as creatives who “sat at the intersection of art and technology" and that he doesn’t identify as an entrepreneur or a business person. “I think of myself as a designer," he said. “I’m a designer who has been afforded one of the biggest canvases in the world."

As he considered why founders seemed to be miserable running their companies—too much bureaucracy, way too many meetings—he realized that he was thinking about it all wrong.

“Maybe it’s not a cultural issue. Maybe it’s quite literally a design flaw," he says. “And so founder mode was my attempt to redesign a modern company."

THE FIRST THING Chesky remembers attempting to design was an American metropolis.

“I tried to redesign the city of St. Louis when I was 7," he says.

The son of two social workers, Chesky grew up in Niskayuna, New York, tinkering with his sneakers and hockey equipment. As he got older, he asked Santa for poorly designed toys so he could take a crack at improving them. By the time he was 11, he was asking neighbors if he could redesign their backyard decks. (“No one commissioned me," he says.) As a teenager, he convinced his father to buy Disney stock so he could get his hands on the company’s annual reports to study architectural renderings of theme parks.

After graduating from the Rhode Island School of Design, he took a job in Los Angeles as an industrial designer. Inspired by Walt Disney taking a chance and moving to Hollywood nearly a century earlier, Chesky moved to San Francisco and lived with his RISD buddy Joe Gebbia. They were scrambling to pay rent when Gebbia sent him an email on September 22, 2007, with a plan “to make a few bucks."

With a design conference coming to town, they realized other broke designers would need a place to crash, so they bought three air beds and welcomed their first guests. Chesky still has the receipt—a memento of the best $55 he ever spent. Before long, Chesky, Gebbia and Nathan Blecharczyk started a company they called AirBed & Breakfast.

By now, the origin story of Airbnb is the stuff of Silicon Valley lore. The startup went from three air beds to billions in sales over the next decade—and never has a company made so much money from bachelorette parties.

And then it was all nearly wiped out in a matter of weeks. In the early days of the pandemic, when Airbnb’s business cratered, Chesky laid off nearly 2,000 employees, or 25 percent of the workforce, and made decisions that felt existential for the company. The crisis and the uncertainty of that year had a profound effect on Chesky and the way he plans to run the business for the rest of his life.

“It’s like when you have a near-death experience," he says. “Luckily, I’ve never had one. But when you have one, I guess your life flashes before your eyes—and you have clarity."

He decided to run the company his way, which meant no longer doing things he was supposed to do just because he was supposed to do them. Like dealing with email. “It was the thing about my job that I hated the most before the pandemic," he said. To him, emails were too inefficient—just one more part of his life that needed a redesign. During the pandemic, he learned to overcommunicate and relied on texts and phone calls. He rarely bothers with email anymore.

Like many CEOs, he sets aside time to work out every day. Unlike most CEOs, he works out from 8 p.m. till 9:30 p.m. Then he keeps working. “If I had a girlfriend, that would probably change," he says. “But I don’t, so I’ll enjoy this." A night owl, he says his creativity peaks from 10 p.m. until he falls asleep sometime before 2:30 a.m. And he doesn’t schedule meetings before 10 a.m. “When you’re CEO," he says, “you can decide when the first meeting of the day is."

He’s also one of the few CEOs who picked up a roommate during the pandemic: his mother. She was already planning to move across the country in March 2020. Then she moved in with him. He was upstairs saving his company. She was downstairs making sandwiches and quiches and soufflés.

“I’d be on calls and she’d literally be like, ‘The food is getting cold!’ " he said.

When I told him it sounded like a scene from Wedding Crashers, he cut me off and quoted Will Ferrell’s character, Chazz: “ ‘Ma! The meatloaf!’ Yeah, that was a little bit of me." Now his parents live down the street.

In all the fervor over founder mode, Chesky says people got one part very wrong. ‘It’s not about being an asshole,’ he said.

As he reoriented Airbnb, Chesky implemented Apple-style product releases, consulted with former Apple design mastermind Jony Ive and hired former Apple marketing executive Hiroki Asai. But the world’s most valuable company wasn’t the only one that influenced him.

In 2023, Chesky was celebrating Thanksgiving with his family a week early when he learned through a group chat that Sam Altman had just been fired as the CEO of OpenAI. He dropped everything to help one of his closest friends navigate the boardroom drama and return to the company a few hectic days later. The following week, Altman delivered a handwritten thank-you note to Chesky.

“I definitely don’t know everything you did," Altman wrote. “But I feel pretty certain that without you, we would have lost the company."

The coup at OpenAI turned out to be a crucial moment in Airbnb history, too. In the immediate aftermath, Chesky was at home by himself over Thanksgiving. “I’ve got all this pent-up energy," he remembers. “I basically open my laptop and I write, like, 10,000 words of where Airbnb is going." That feverish document became the road map for the expansion beyond homes into services and experiences—and nine more categories that will be rolling out in the next few years, Chesky says. Before he decided to rewrite the app and rebuild the entire company, he first had to decide whether it would all be worth it. He says he subjects his own ideas to greater scrutiny to “make sure I’m not buying into my own hyper-delusion," asking himself: Is this truly something that people want?

He’s been asking himself that question since his first day at Y Combinator, when he received a T-shirt with a useful mantra: MAKE SOMETHING PEOPLE WANT. He believes so many people will want services on Airbnb—both tourists and locals—that it could be even bigger than the company’s short-term rental business.

It’s still a risky move. You don’t need a wild imagination to picture all the ways getting a massage from a stranger at home could go horribly wrong. Chesky says Airbnb has rigorous safety measures to protect users, vetting everyone offering services on the platform before stamping them with the company’s seal of quality.

When asked how he would characterize Airbnb today—a hospitality company? a travel or tech company? a lifestyle company?—his answer reminded me of something Wolfe Herd said about how his mind works: “You ask him a question, and he’ll have, like, quotes from Leonardo da Vinci."

In this case, he cited ancient Greeks and Japanese samurais before quoting a Hindu maxim: “Guest is god."

“We’re in the business of human connection," he said. “There’s an ancient history of people-to-people hospitality. I think that’s what Airbnb is about."

WHEN I ASKED CHESKY who else I should talk to for this article, he rattled off names of people who could describe him in “excruciating detail," including other founders, colleagues—and Barack Obama.

In 2022, Chesky donated $100 million to Obama’s foundation to launch a scholarship program for college students interested in public service. They’re known as Obama-Chesky Voyagers. The two met when Obama was in office, and he now calls Chesky “a genuine friend." He says he actually remembers hearing about Airbnb in 2008, though he wouldn’t get a chance to use the product for a while. “During my presidency," he explains, “Secret Service was a little bit strict." But even before his presidency, he was intrigued.

‘I definitely don’t know everything you did,’ Sam Altman wrote to Chesky in a note thanking him for his guidance after being fired as CEO of OpenAI. ‘But I feel pretty certain that without you, we would have lost the company.’

“What they were trying to do with Airbnb was consistent with my basic view of politics and the American people: that people were basically good, could trust each other and work together despite different backgrounds," Obama says.

When he went browsing for places on Airbnb, Chesky acted as his personal concierge, researching homes so he could make an informed decision—and impress his wife.

“It’s just one more debt that I have to Brian," Obama says.

It turns out Chesky was repaying a debt of his own. In late 2017, they were chatting and Obama asked about his vision for Airbnb and where he wanted to take the company. Chesky wrote up a manifesto with his most audacious thoughts. They talked about it—and kept on talking. “When you’re on the phone with Brian," Obama tells me, “you can hear him tapping away because he’s taking notes." For a while, they had a standing weekly call to discuss Chesky’s homework. “It was almost like night school with the president of the United States," Chesky said.

Those conversations and the essays he wrote for Obama ultimately shaped the letter he would write in the Form S-1 that Airbnb filed to go public in 2020.

On that first day of trading, the company became more valuable than Marriott, Hilton and Hyatt combined. Still, for every person who checks into an Airbnb, there are nine who choose hotels. Chesky isn’t one of them. Even as a CEO whose company pays for his personal security detail, he says he’s almost always in Airbnbs on the road. “The only time I’m in a hotel is if I’m at a conference, like Sun Valley," he said.

When he opened the app to show me some of his favorites, he scrolled through what can only be described as Airbnb porn. Then he told me about an especially memorable place in St. Barts once owned by Mikhail Baryshnikov. It’s where he took his parents and sister on a family trip back in 2011, when he decided to really splurge for the first time in his life.

That is, when he suddenly had the means, his most extravagant purchase counted as putting money back into the company he founded.

“The amount of money I’ve spent on Airbnb—I’d be embarrassed if it wasn’t Airbnb," he says.