Part IThe Story
No Bell Ringing
There was no bell. On the morning of December 10, 2020, the company that two out-of-work designers had named after three inflatable mattresses began trading on the Nasdaq under the ticker ABNB. Its co-founder and chief executive, thirty-nine years old and, by his own later description, "by myself 24/7," watched it happen on a screen. The shares had been priced the night before at $68, well above the range of $56 to $60 that bankers had floated earlier that week. They rose 113 percent on the first day of trading. The offering raised roughly $3.5 billion. By the close, the market had assigned Airbnb a value of about $103 billion, more than Marriott ($43 billion), Hilton ($39 billion), and Hyatt ($8 billion) put together. Eight months earlier, in April, Silver Lake and Sixth Street Partners had bought $1 billion of its stock at an $18 billion valuation and lent it another $1 billion at interest rates between 9 and 11.5 percent. That was the price of credit for a travel company in a year when nobody traveled.
The company's official timeline says that Airbnb "rings the bell with hosts around the world who make Airbnb, Airbnb." Chesky remembers it more plainly. "There's no bell ringing," he told the podcaster Dax Shepard years later, "it's all on Zoom—the entire IPO." He called the weeks around the offering "one of the saddest periods" of his life. He had grown up the son of two social workers in upstate New York, and as a boy he had "desperately wanted to be successful," on the theory that success would deliver its own reward. "I had this image that if I got successful I'd have all these people around me, all these friends, I'd have all this love, all this everything, and my life would be fixed." What actually arrived was a $100 billion valuation, a fortune that Fortune's rough arithmetic put at $11.2 billion, the knowledge that "everyone in high school" now knew what he did, and an empty room. "I had done that," he said. "I had so isolated myself totally focused on working."
The difficulty is easy to state. His company sold belonging. It was the man who sold it who was lonely.
Every serious account of Brian Chesky eventually runs into that problem, and none of them settles it. Here was the founder who spent three years without a fixed address, sleeping in strangers' spare rooms as a matter of corporate principle. He built a $12 billion-a-year business on the claim that "anyone can belong anywhere," and then found himself, at the summit, alone. Thirteen years before the Zoom IPO he had driven into San Francisco with about $1,000 in his bank account, a rent bill he could not pay, and nowhere in particular to sleep. Someone took him in. The rest of the story keeps returning to that fact.
By the Numbers
The House That Strangers Built
$12.2BAirbnb revenue in 2025, up from $0.4B in 2014
5.5M+Hosts on the platform (May 2026)
2.5B+All-time guest arrivals
$380B+Earned by hosts, all-time
80%Share of business lost in eight weeks of spring 2020
$68 → $103BIPO price and first-day valuation, December 2020
31.9%Chesky's share of Airbnb voting power (10.7% economic)
Niskayuna, New York, is a suburb north of Albany that does not produce many art-school dropouts or many billionaires, and it was not expecting either from Brian Joseph Chesky. His parents, Deborah and Robert, were social workers, descendants of Italian and Polish immigrants who, in Brad Stone's phrase, "doted endlessly" on him and his younger sister, Allison. Their professional horizon was protective rather than ambitious. Whatever job he took, they told him, he should make sure it came with health insurance. "That was the extent of my perceived ambitions," Chesky said later, in a Stanford lecture hall, to an audience of students who had presumably been raised on larger dreams.
The boy himself was harder to classify. His first passion was ice hockey. His second, arriving in adolescence, was drawing, and the drawing quickly became something closer to redesign. He traced the toy and sporting-goods catalogs that came to the house, then redrew them and changed them. At seven, he has confirmed, he asked Santa Claus for poorly designed toys so that he could redesign them. When Game Boy and Game Gear came out he redrew the consoles. When Nike Airs arrived he went after footwear. He named Leonardo da Vinci as an inspiration. He watched friends of his parents remake their backyard and got interested in landscape architecture, and then in urban planning, which for a child in Niskayuna amounted to a fascination with how other people arranged the places they lived in. "I didn't know it was called design back then," he told Debbie Millman in 2026. Nobody around him knew either. "The closest thing to an entrepreneur I knew of," he said, "was Bob of Bob's Pizza."
His senior yearbook quote at Niskayuna High School, Class of 1999, read: I'm sure I'll amount to nothing. He thought it was funny. His father did not. "Nothing?! Nothing?!" Robert Chesky shouted when he saw it, a reaction his son was still quoting on Instagram eighteen years later, on the way to deliver commencement addresses at both his high school and his college.
The college was the Rhode Island School of Design, and his mother received the decision with a social worker's sense of the economics. "You somehow managed to pick the only job in the world that pays less than a social worker," she told him. "You'll get paid nothing."
At RISD he was an odd fit, an athlete at an art school. He captained the hockey team, which played under the name the Nads, and he designed its unofficial mascot, a figure called Scrotie whose anatomy needs no explanation. He was also, improbably, a competitive bodybuilder; a 2014 Fast Company profile still credited him with sixteen-inch biceps. He studied industrial design under the influence of Charles and Ray Eames and Walt Disney. That pairing explains a good deal of what came later. The Eameses believed a chair could carry a philosophy of living. Disney believed an experience could be engineered down to the texture of the pavement.
He met Joe Gebbia in 2000. "We were among the few kids at art school who played sports," Chesky wrote years later. "I ran the hockey team and Joe ran the basketball team. We had the hardest marketing challenge in the world—how do you get art students to a sports game?" They competed for the same thin audience and played ping-pong against each other "almost every day."
At his RISD commencement in 2017, accepting an honorary doctorate (the college president stumbled over the new title, "Dr. Brian Ches—uh, Dr. Brian Chesky"), he told the graduates what he had felt in their seats thirteen years earlier. "I had no sense of what I wanted to do. And I don't think anyone expected too much of me." The first of his three lessons, he announced, he had learned "from the Nads."
That was the register he worked in. He held sincerity and absurdity in the same hand and refused to let either go.
Shoes Off on Rausch Street
Chesky graduated in 2004 and moved to Los Angeles to work as an industrial designer at a firm called 3DID. He designed toys, guitars, and medical equipment. He sat in long commutes. The work that finally broke his patience was a toilet seat, the Pureflush, made for American Inventor, a reality competition produced by Simon Cowell. The British press later called it "a toilet seat for the seriously ill. Seriously." He cut his hours in 2007 to design furniture. He was, as he wrote later, "miserable."
Gebbia, meanwhile, was ahead of him, as Gebbia usually was in those years. Joe Gebbia was born in Atlanta on August 21, 1981, eight days before Chesky, the son of two independent health-food sales representatives. He grew up in Lawrenceville, Georgia, worked as a ball boy for the Atlanta Hawks, and ran his first business in grade school selling drawings of Teenage Mutant Ninja Turtles to classmates. At RISD a professor told him to keep a foundations project small and achievable. He built sixteen full-size chairs instead. He also invented CritBuns, foam seat cushions shaped like buttocks, made to keep art students' pants clean during hours-long critiques. His graduating class of 800 chose them as its senior gift, and then he sold them to real retailers. In a pizza shop in Providence in 2004, as Chesky was preparing to graduate, Gebbia "took a dramatic pause" and said: "Brian, I think we're going to start a company together... and there's gonna be a book about it."
"A book?" Chesky recalled. "I was just trying to figure out how to get a job so I didn't have to move back home with my parents."
There was eventually a book: Leigh Gallagher's The Airbnb Story. Gallagher is a senior editor at Fortune, and the book remains the most thorough reporting on those years. The invitation that made it possible came in a package. One day in Los Angeles, Chesky opened a box containing a CritBuns cushion and a note from Gebbia: Come to San Francisco. Gebbia "spent the next twelve months prodding me to come until, finally, he figured out a way." In August 2007 he invited Chesky to his twenty-sixth birthday party.
The apartment was on Rausch Street, in San Francisco's South of Market district. Chesky's description of walking in, written fifteen years later in a note to Airbnb employees, is the closest thing the company has to scripture, and it is worth quoting at length because nearly everything later can be found in it:
"You had to take your shoes off upon arrival. Along the walls were dozens of post-it notes with ideas written on them. Doors were turned on their side and converted into giant desks, and there was a wall of bookshelves with design books color coordinated. It felt like being back at the RISD design studio—ideas were overflowing, and as soon as I entered, I felt like I was in a space where something important was going to happen."
He slept that night on a brown leather couch in Gebbia's living room. In the morning he woke to find Gebbia's roommate, "a tall person in a crimson jacket and the longest fingers I'd ever seen," typing furiously on a laptop. This was Nathan Blecharczyk, two years younger and of a different species entirely. He had grown up upper-middle-class in Boston, attended Boston Latin Academy, and built a web-hosting business in high school. The business served spammers and was at one point listed on the Spamhaus Project's Registry of Known Spam Operators, and it made enough money to pay his Harvard tuition before he shut it down in 2002 to concentrate on computer science. He had found the room on Rausch Street through a Craigslist ad. (At Harvard he had worked on the business staff of the Crimson. The jacket may have been a coincidence.) Chesky "had no idea at this point the three of us would start a company together."
Five weeks later he moved in. He drove up from Los Angeles in a Honda Civic with his belongings and learned that his share of the rent was $1,200. He had about $1,000.
That autumn the Industrial Designers Society of America was holding its conference in San Francisco, and the event's website showed the nearby hotels sold out. The two designers owned three air mattresses. They built a simple website, AirBed & Breakfast, and offered the mattresses to conference-goers for $80 a night, with Pop-Tarts for breakfast. They expected twenty-something designers like themselves. Instead they got a father of five from Utah, a thirty-five-year-old woman from Boston, and a man from India: Kat, Michael, and Amol, as Chesky would name them. The hosts took their guests to the conference, introduced them to friends, and showed them a version of the city tourists rarely see. "The normal arc of a friendship that takes years to build," Chesky said later, "now took a few days when people were living with you in your home." One of the guests invited him to his wedding.
His later sentence about this period is the one that matters most. "Before we hosted Kat, Michael, and Amol," Chesky wrote, "Joe hosted me. He not only took me into his home, but he connected me to the startup community in San Francisco. Joe was the OG host."
The company began, then, with Chesky as the guest. He arrived with too little money, slept on someone else's couch, took off his shoes at someone else's door. He never quite stopped being that person, and it may be why he understood the product so well.
Cockroaches
"A number of people have told me that Airbnb is the worst idea that has ever worked," Chesky said in 2015, and laughed. In 2008 it looked mostly like the worst idea.
Blecharczyk joined in February 2008 as chief technology officer and coded the site in Ruby on Rails. They launched at South by Southwest in Austin that March and got two bookings. One of them was Chesky. The trip produced one thing of lasting value: Chesky met Michael Seibel there, and Seibel would later connect the founders to Y Combinator. They relaunched. Nobody noticed. "We actually launched three times," Chesky told a later SXSW audience. "No one noticed the first two times, so we launched again."
The third launch, on August 11, 2008, was timed to the Democratic National Convention in Denver, where Barack Obama would accept his party's nomination before a crowd of tens of thousands and where hotel rooms were as scarce as they had been in San Francisco the October before. TechCrunch wrote it up that day under the headline "AirBed And Breakfast Takes Pad Crashing To A Whole New Level," and the traffic crashed the site. The founders pitched small bloggers and let the story climb to the Denver Post and then to the New York Times. The convention produced 800 listings and 80 bookings. That same August, Airbnb launched its own payments system. By 2019 it would process roughly $70 billion a year in more than forty currencies. In 2008 it processed very little.
They needed $150,000 for about 10 percent of the company and pitched more than twenty investors. All of them said no. "Joe and I were designers," Chesky said, "and as far as they were concerned, designers didn't start companies. We didn't look like a tech founder." After the convention, Chesky and Gebbia each carried roughly $20,000 in credit-card debt.
The solution was cereal, and it is now one of the most retold stories in Silicon Valley. They bought 1,000 boxes of commercial cereal and repackaged them, with box art of their own design, as "Obama O's" and "Cap'n McCain's." The Obama boxes sold as collectibles for $40 each. The cereal raised somewhere between $20,000 and $30,000, enough to clear most of the debt. Chesky has called it his "low point," and he tells it as a joke on himself and on the industry's mythology: "At no point in the Facebook story was Mark Zuckerberg hot gluing hundreds of cereal boxes in his apartment."
The cereal did something the pitch decks had not. Paul Graham, a computer programmer who had co-founded Y Combinator and then made himself the most influential essayist on startups, was not buying the idea of strangers sleeping in strangers' homes. Then one of the founders showed him an Obama O's box and told him the story.
— Paul Graham to the Airbnb founders, as recalled by Brian Chesky at SXSW, 2013You guys won't die, you're like cockroaches.
Y Combinator admitted them to its winter 2009 batch in January. It gave them $20,000 for 6 percent of the company, along with a piece of advice Chesky has repeated in essentially every long interview since. Their biggest market was New York, with a princely hundred customers. Graham told them to go there. "It's better to have 100 people love you than a million people that sort of like you."
So they went to New York and knocked on doors. They visited their hosts one by one and photographed their apartments themselves, because the listings looked bad, camera phones were primitive, and nobody would trust a stranger's home they could not see properly. In March 2009 they shortened the name to Airbnb, to stop people from thinking the company only rented air mattresses. The site now offered apartments, whole homes, and vacation rentals, and it had 10,000 users and 2,500 listings. In April, Sequoia Capital put in $600,000 of seed money at a penny a share; the partner Greg McAdoo wrote the check for $585,000 of it. Jawed Karim, Keith Rabois, and Kevin Hartz joined through Youniversity Ventures.
Every venture firm that had passed in 2008 was now looking at the most expensive mistake in its history. The firms had not been wrong about the founders' profile; they were designers, not engineers, and designers did not start companies. They had been wrong to treat the profile as a verdict. Chesky would build an entire theory of hiring on that error: "I don't think you should ever hire somebody because they look like something else. You want a new thing."
The Homeless Entrepreneur
In the fall of 2010 Chesky took the title of chief executive officer. Of the three founders, he was the one with no prior business experience. Around the same time he moved out of the apartment on Rausch Street, and for the next three years he did not have a home.
The Mail & Guardian called him "the homeless entrepreneur" in 2013, and the label was literal. Chesky had decided that the best way to improve the service was to depend on it. He slept in strangers' spare rooms, on their couches, in their empty vacation homes, booking each one through Airbnb. The software industry has a phrase for this, eating your own dog food. When Chesky did it, it also meant living as a perpetual guest. The CEO of the company that promised belonging had arranged his life so that he belonged nowhere in particular.
Two images from these years show the company's growth. The first is the money. In November 2010, Greylock Partners and Sequoia invested $7.2 million at about 21 cents a share, split-adjusted. In July 2011, Andreessen Horowitz, Digital Sky Technologies, and General Catalyst, joined by the actor Ashton Kutcher and his partner Guy Oseary, put in $112 million at $3.21 a share and a valuation of about $1.3 billion. A company that could not raise $150,000 three years earlier was now a unicorn. Each night, by one count, it matched 10,000 travelers with 10,000 spare rooms.
The second is the office. A British profile in 2011 described a headquarters with a giant treehouse, half of a decommissioned airliner, and a weekly custom called Moustache Mondays, on which staff wore fake moustaches. It is the kind of detail that ages badly, and the writer seemed unsure whether to admire it or laugh at it. But the office came from the same impulse as the meeting rooms at 888 Brannan Street, the company's headquarters from June 2013, a few blocks from that first listing on Rausch. That building had been put up in 1917 to house a battery factory. Some of its meeting rooms reproduced actual Airbnb listings, one in Fiji among them, and one reproduced the war room from Dr. Strangelove. A designer was making the company's culture into something people could walk through.
The expansion came under direct attack. In 2011 a German company called Wimdu, heavily funded by the Berlin clone factory Rocket Internet, copied Airbnb's product almost wholesale and moved into Europe. The founders considered buying it and decided against it. In May 2011 they bought a smaller German imitator, Accoleo, opened their first international office in Hamburg, and began expanding across the continent. London followed in October 2011. Early in 2012 came Paris, Milan, Barcelona, Copenhagen, Moscow, and São Paulo. In March 2012 Airbnb bought CrashPadder, its largest British competitor, and with its 6,000 listings became the largest lodging site in the United Kingdom. Sydney and Singapore opened before the end of the year. Wimdu eventually merged with another rival, 9flats. Five years after its founding, Airbnb would put its European headquarters in Dublin.
Chesky later reduced this period to a sentence: "We need to be all over the world. We have to hire citizens of the world." He also recalled explaining the company to his grandfather, who replied with two words: "Of course!" Seventy years earlier, the old man pointed out, anyone traveling to another city stayed with a local family or in a boarding house. What sounded radical to Sand Hill Road was ordinary to anyone who remembered travel before the hotel chains. Chesky took the lesson seriously. "We're part of the era of the sharing economy," he said in 2013, "which is what comes after the era of mass production." In his telling the newest company in travel was reviving something very old.
Below the Waterline
The crisis that taught Chesky to be a chief executive arrived in the summer of 2011, and he handled it badly.
A host's home was vandalized by a guest. Chesky wrote blog posts describing the company's response. The host publicly contradicted his account. A story about a stranger who had wrecked a home became a story about whether the company could be believed. Chesky's response, which Gallagher reconstructs carefully, was to write a second public message, this one admitting the failure. The company expanded its customer-service team and created a fund for hosts who suffered similar damage. In May 2012 that fund became the $1 million Host Guarantee. In Gallagher's account, Chesky considered the episode a "rebirth" for Airbnb.
The lesson is less obvious than it sounds. The apology was not the remedy. The remedy was the money, the staff, and a written guarantee, things that would still exist after the news cycle moved on. Nine years later he would do the same thing at much larger scale.
He began to look, systematically and without embarrassment, for instruction. "Be shameless," he told an audience at the Oxford Union. "I was shameless to seek out people that could help me every step of the way." Fortune's list of the people he approached is long and odd: Warren Buffett; Disney's Bob Iger; Apple's Jony Ive; LinkedIn's Jeff Weiner; Salesforce's Marc Benioff; the investor Peter Thiel. There was a second list of people he could learn from only by reading, including Steve Jobs, Walt Disney, George Bernard Shaw, and Dwight D. Eisenhower. And there was George Tenet, director of the CIA from 1997 to 2004, who had signed off on the intelligence behind the 2003 invasion of Iraq. In 2015 Chesky asked him for lessons in management and got one.
In the President's Room at 888 Brannan, among wood paneling, leather club chairs, and a model ship on the coffee table, Chesky took a napkin and drew a boat for Fortune's Leigh Gallagher. She noted, a little dryly, that for a RISD graduate it was "a rudimentary-looking vessel." He drew a line of waves through the middle of the hull and two holes beneath it with water coming in.
"If you think about it, Airbnb is like a giant ship," he said. "And as CEO I'm the captain of the ship. But I really have two jobs: The first job is, I have to worry about everything below the waterline; anything that can sink the ship." Beyond that, he would choose two or three areas "that I'm deeply passionate about," where he could "add unique value." He had picked three: product, brand, and culture. "With the others I really try to empower leaders and get involved only when there are holes below the waterline."
The theory came from a spymaster, the drawing was crude, and the idea was sound. It would also prove, later, to be not quite enough.
In September 2013 he made the hire that best shows what he was trying to become. Chip Conley was born in Orange, California, in 1960 and earned a Stanford MBA in 1984. Three years later he founded Joie de Vivre Hospitality, starting with a single motel in San Francisco's Tenderloin, the Phoenix, and ran the company for nearly twenty-four years, building or managing about fifty boutique hotels. He sold it in 2010. He had written a book, Peak, applying Abraham Maslow's hierarchy of needs to business, and had given a TED talk on the subject. Chesky brought him in as Airbnb's first Head of Global Hospitality and Strategy. A young man whose company threatened hotels was hiring a hotelier to teach his hosts how to host. Conley became, in his own description and Chesky's, a mentor. He built bridges to the hotel and real-estate industries the company was disrupting, and he created the annual Airbnb Open, a convention for hosts. In 2018, after leaving his operating role, he would found the Modern Elder Academy in the Baja seaside village of El Pescadero. He called it "the world's first midlife wisdom school." He had spent his life helping strangers feel at home and ended up running a school for middle-aged people.
The professional managers Chesky collected so eagerly in these years would later become, in his own account, part of the problem. In 2015 none of that showed. Fortune ran a piece titled "How one young guy can create $25 billion," quoting the Kleiner Perkins partner Juliet de Baubigny: "I have never seen a moment in time when there is such unprecedented support for the founder-led company." TPG had invested $450 million at a $10 billion valuation in April 2014. In June 2015 a consortium including General Atlantic, Hillhouse, and Tiger put in $1.5 billion at $25.5 billion, more than the market value of Marriott. In May 2015 President Obama named Chesky a Presidential Ambassador for Global Entrepreneurship. Time put him on its 100 list. In June 2016 he and his co-founders signed the Giving Pledge.
Buffett's assessment, given to Gallagher, has been quoted often, and it is the best short description of the man:
"[Brian Chesky] feels it all the way through. I think he would be doing what he's doing if he didn't get paid a dime for it."
The Strangers Problem
The founding objection to Airbnb was a single sentence that Chesky repeats as though it still stings: Strangers will never trust one another. The company's answer was partly technical. It verified host identities. It insured homes up to $1 million. It built a review system in which both parties are rated and neither sees the other's review until both have been submitted or the window has closed. "Trust is everything," Blecharczyk told Newsweek. "The single most powerful thing is the review system... because everyone understands that this relationship is going to culminate in a review, it puts everyone on their best behavior going into this."
The deeper answer was that strangers did trust one another, often enough, and the business grew on that. Two million people were staying in Airbnbs on New Year's Eve 2016. By October 2019, two million were staying every night.
But trust between strangers is also a question of which strangers, and here the platform ran into the oldest problem in American hospitality. In 2016, reports showed that hosts were declining requests from guests whose names suggested they were Black. Airbnb's design had put a guest's face and name in front of the host before the host decided, and that made discrimination easy. That July, the company hired Eric Holder, the former attorney general, to help write an anti-discrimination policy. Guest photos were hidden from hosts until a booking was accepted. In February 2017 the company ran a Super Bowl advertisement, #weaccept, against the administration's travel ban. That same month Chesky added a third title, Head of Community, to co-founder and CEO. In August 2017, before the white-supremacist rally in Charlottesville, Airbnb canceled bookings and closed the accounts of attendees, citing the terms of service requirement that members "accept people regardless of their race, religion, national origin, ethnicity, disability, sex, gender identity, sexual orientation, or age."
That was the company acting on its stated values. It did not always manage to.
In November 2018 Airbnb announced it would remove roughly 200 listings in Israeli settlements in the occupied West Bank. Property owners sued in Israel and the United States, alleging discrimination based on place of residence. In April 2019 the company reversed itself and pledged to donate any profits from those listings to humanitarian organizations. In China, where Airbnb operated a local brand called Aibiying with Blecharczyk as chairman, government officials asked in 2019 for expanded data-sharing on guests. Sean Joyce, a former deputy director of the FBI who had joined Airbnb six months earlier, raised objections and then resigned. According to the Wall Street Journal, Blecharczyk responded that the company was not there to "promote American values." Airbnb kept its sponsorship of the 2022 Beijing Winter Olympics despite appeals from human-rights groups. In May 2022 it left China anyway, citing costly regulations and pandemic lockdowns. China had accounted for less than 1 percent of revenue.
Cities were the other kind of stranger. Airbnb's growth depended on homes, and homes are where cities keep their residents. Critics argued that every apartment converted to a short-term rental was one fewer for a tenant. Supporters, including the company, argued that the effect on housing costs was small and that the real problem was the supply of housing. Both sides found evidence. In Lisbon, a moratorium on short-term rentals failed to lower housing costs and mainly raised hotel prices. In Barcelona, all short-term rentals are scheduled to be banned in November 2028. New York prohibits rentals of under thirty days unless the host is present. Amsterdam caps rentals at thirty nights a year. Palma de Mallorca banned them outright.
Opposition took more personal forms too. Murray Cox is an Australian-American community activist who moved to Brooklyn in 2008, the same year Airbnb launched. In 2014 he began scraping the company's listings, alone. Working with a Canadian collaborator, Tom Slee, he compared his data with a public data release Airbnb had made for New York in December 2015 and found that more than 1,000 listings that violated the city's multiple-dwelling law had been removed shortly before the release. Their February 2016 report was titled "How Airbnb's Data Hid the Facts in New York City." Airbnb said the listings had been removed for violating policy, and it has since enforced a "one host, one home" rule in New York. Cox's site, Inside Airbnb, eventually covered eighty cities. It cost him roughly $10,000 a year to run, paid for by cities, researchers, and, inevitably, the hotel industry. Airbnb called his data "garbage." In February 2019 its representatives met with him anyway. He was, in his way, the company's founding sentence come back to haunt it: one man with a laptop and a theory about what was happening inside other people's homes.
Chesky's defense of the industry, offered at a travel conference in 2024, was candid about how little control he has: "When you build a platform that impacts hundreds of millions of people, it is impossible for there not to be unintended consequences." His 2016 statement to Vanity Fair is more revealing, because it treats the danger as internal rather than external.
— Brian Chesky to Vanity Fair, 2016If we don't grow past what we originally invented, what led to your success leads to your death.
He said it in a yurt in Topanga Canyon in September 2016, without cell service, while testing a three-day product called "The TV Writer's Journey." Professional television writers had designed it to show travelers what it was like to work in Los Angeles. The yurt belonged to one of the writers, and its toilet was an outhouse over a compost heap. The participants, simulating a writers' room, came up with a plot about a bride who steps through a space-time transporter on her wedding day into a parallel universe where she is a stand-up comic. A young woman in jean shorts who had signed up on a whim did not know who Chesky was. "What are the chances," the CEO of a $30 billion company asked her, "this could get made into a real TV show?" The reporter believed he meant it. The product, Airbnb Trips, launched that November. He also said, of the nights before it launched, that he sometimes woke with his heart pounding.
Eight Weeks
"My God," Chesky told GQ in 2021. "I thought the most interesting part of the Airbnb story was the early days. I never thought that I'd live through something that would be even crazier."
The signals came from China in late January 2020. By February the business there had fallen by something like 80 percent. "Normally, when a business drops eight per cent there's something seriously wrong," he said. In a meeting he remarked, "naively," as he later put it, that it would be very bad if the thing spread beyond China. Then the European numbers started to fall. He watched it move from east to west, "like a slow moving car crash."
He dates the reckoning to the Ides of March, Sunday, March 15, the day of an emergency board meeting at which Ken Chenault, the former chief executive of American Express, was among the directors. The company lost 80 percent of its business in eight weeks. Bookings fell as much as 96 percent in some cities.
On March 11, the World Health Organization had declared a pandemic, and Airbnb had decided to let guests cancel and receive full refunds, including the company's own fees. It was the right call for public health and a disaster for the hosts. They learned about it at the same time as everyone else. On March 30, Chesky sent them a letter. Its key passage is easy to read past:
"While I believe we did the right thing in prioritizing health and safety, I'm sorry that we communicated this decision to guests without consulting you—like partners should. We have heard from you and we know we could have been better partners."
Then came the remedy, as in 2011, in the form of money. Airbnb would pay hosts 25 percent of what their cancellation policies would normally have earned them on COVID-related cancellations with check-ins between March 14 and May 31, retroactively, about $250 million in total, "covered entirely by Airbnb." It would create a $10 million Superhost Relief Fund offering grants of up to $5,000 that did not need to be repaid. Employees had contributed $1 million of that from their own pockets. "Joe, Nate and I," he wrote, "are personally contributing the remaining $9 million."
In April came the expensive capital from Silver Lake and Sixth Street. On May 5 came the layoffs: about 1,900 people, roughly a quarter of the workforce in the Americas, Europe, and Asia. The severance included extended health coverage. Some reports said a year of it, which would have pleased his parents. The company published a public directory of departing employees so that other firms could hire them. Chesky's letter to the staff included a sentence he would later revisit: "I have a deep feeling of love for all of you."
He did not retract it. Four years later, on Adam Grant's podcast, he explained it. "The reason I used the word love is 'cause that's what I felt at the time. I wrote that letter fairly quickly... I wrote what I felt." He said he had reviewed the name of every departing employee. But he also gave up something the company had believed about itself since the treehouse and the moustaches. "It is true that a company is not a family. In fact, we had to make that pivot. We used to refer to ourselves as a family, and then we did have to fire people... and yeah, you don't fire members of your family." In a podcast that year he had put the question more starkly: "How does a company whose mission is centered around belonging have to tell thousands of people they can't be at the company anymore?"
The shutdown also produced surprises. Rural bookings surged as people fled cities for cabins within driving distance. Frontline Stays housed medical workers. Online Experiences gave hosts a way to earn money through a camera. Chesky said he opened his own home as an Airbnb during the pandemic to understand hosting better. He was, by then, a man with a home to open. The New York Times headline that July, "Airbnb Was Like a Family, Until the Layoffs Started," was accurate.
Four months later the company went public at $68 a share. Chesky told GQ he felt "39 years old going on 49."
The Steering Wheel
There is a version of the Airbnb story in which the IPO is the triumph. Chesky tells a darker one. In it, 2019 is the low point, earlier than the pandemic and worse in a way, because it was his own doing.
In 2019 Airbnb was the most famous startup in the world, with revenue of $4.8 billion and a net loss of $674 million. It had bought HotelTonight for $400 million in March and Urbandoor in August. It was pursuing luxury, business travel, experiences, a magazine with Hearst, a film division, and, Chesky had said in 2018, possibly an airline. By his own account he had followed the advice that well-meaning people had given him as the company grew: hire good people and give them room to do their jobs. "I woke up in 2019," he later said, "feeling like the car had no steering wheel."
The pandemic gave him a reason to take control back. He eliminated divisions, removed what he called "fiefdoms," and involved himself directly in daily operations. For two to three years he reviewed every detail of the work. To learn how, he went to the one founder he thought had faced a comparable crisis, Steve Jobs at Apple in 1997, near bankruptcy. Because Jobs was dead, he studied him through the people who had worked beside him: Jony Ive and Hiroki Asai, Apple's former creative director. "[Jobs] said you have to be in all the details of people's work," Chesky recalled. "I think there's a lot of leaders that don't understand their business—it's kind of like leading a cavalry, and you can't ride a horse. It makes no sense."
In September 2024, at a Y Combinator event, he was scheduled to speak off the record for thirty minutes. He talked for two hours about what had happened since the pandemic and how he now ran the company. Paul Graham, who had called him a cockroach sixteen years earlier, wrote afterward that most founders he spoke to considered it the best talk they had ever heard. "Ron Conway, for the first time in his life, forgot to take notes." Graham's resulting essay, "Founder Mode," argued that conventional management advice amounted, in practice, to "hire professional fakers and let them drive the company into the ground." He described founders who felt "gaslit from both sides": by advisers telling them to manage like professionals, and by employees when they did. The essay went viral, produced memes, and drew serious criticism. Some called founder mode a new name for micromanagement. Others pointed out that women founders were not given the same latitude to lead that way.
Chesky spent the following weeks clarifying. "I never called it founder mode," he said at the Skift Global Forum. Jobs, he argued, "didn't micromanage [his employees], he partnered with them." He said publicly that women founders had told him they could not operate in founder mode the way men could, and that this needed to change. His summary of the method to Patrick O'Shaughnessy was more careful than the meme: start hands-on, and give ground grudgingly, rather than the other way around.
By then the numbers supported him. Airbnb lost $4.58 billion in 2020 and $352 million in 2021. It earned $1.89 billion in 2022, its first profitable year as a public company, and $4.8 billion in 2023, the latter helped by a one-time tax benefit. Graham noted that its free-cash-flow margin was "among the best in Silicon Valley." The company that had been worth $18 billion during the April 2020 rescue was worth more than a hundred billion at times during the next two years.
Running beneath all this was a long admission. Chesky has acknowledged that Airbnb spent sixteen years failing to launch a second hit, because each time it tried to scale globally from the first day. Experiences, the product he had tested in the Topanga yurt, never became what he hoped. The new approach, which he calls Project Hawaii, uses teams of ten or twelve people, which he likens to Navy SEAL units, coached directly by the CEO and sequenced as crawl, walk, run, fly: pilot in one city, expand to ten, then industrialize. He says the first such project added roughly $200 million in its first year and $400 to $500 million in its second. It is Graham's advice from 2009, a hundred people who love you, applied by a public company with 8,200 employees.
In May 2025 Airbnb relaunched Experiences and introduced Services, through which guests can book chefs, massages, personal trainers, hair and makeup, and photographers through the app. Chesky now speaks of changing the company's "atomic unit" from a home to a person. He told The Verge he wanted to build something close to an everything app. That November he described the past: "If we don't grow past what we originally invented..." He had been saying it since 2016.
The AI period has drawn him further out. When Sam Altman was briefly ousted from OpenAI in November 2023, Chesky helped, in his words, "put the company back together." He calls himself "probably one of his closest confidants." He introduced Altman to Jony Ive, which eventually led to Ive taking over design at OpenAI. The same month, Airbnb bought an AI startup, GamePlanner.AI, for just under $200 million. "This is probably going to change the world more than the Industrial Revolution," Chesky said in 2024. The Oxford Union has a recording of him offering the opposite caution about partnerships: "never ever ever ever, or maybe not ever ever, but be very very careful about ever partnering with a large company. It almost never works." He tends to arrive at certainty and then revise it on the spot.
His daily schedule now reflects someone with the power to arrange things as he likes. No meeting begins before 10 a.m. He works out until about 9:30 p.m., does his best work between 10 p.m. and roughly 2:30 a.m., and has largely given up email, which he says he hated more than anything else about the job before the pandemic. "When you're CEO," he told the Wall Street Journal, "you can decide when the first meeting of the day is." He added, without visible irony: "If I had a girlfriend, that would probably change. But I don't, so I'll enjoy this." Whitney Wolfe Herd, who returned to run Bumble after stepping away, said he taught her that being a public-company CEO "doesn't have to be miserable." "He really taught me how to be a CEO again," she said.
The Top of the Mountain
Chesky borrowed his favorite image from Simon Sinek, with acknowledgment. In January 2018, at the company's tenth anniversary, he sent an open letter to the Airbnb community. It opened: "I am absurdly lucky even to be writing this email." A close adviser had phoned him with advice he could not forget: "institutionalize your intentions so that even as you grow, you can minimize what conflicts with your vision." Airbnb, he wrote, was "still young, and the cement hasn't hardened." It would have two defining traits: it would serve all its stakeholders, and it would have an "infinite time horizon." A vision, Sinek had told him, "is a mountaintop you never quite get to." Business, unlike sports, has no clock. "A 21st-century company should eventually become a 22nd-century company."
He is still using the mountain, but it has changed meaning.
Barack Obama, whom Chesky met late in the second term at a global entrepreneurship summit, became, he says, "really close," and then something close to a mentor, with a weekly standing conversation. In May 2022 Chesky pledged $100 million over five years to the Obama Foundation for the Voyager Scholarship. It gives students pursuing public service up to $50,000 in financial aid, a $10,000 stipend, free Airbnb housing for a summer of work and travel, and a $2,000 travel credit every year for a decade after graduation. Earlier he had committed the net proceeds of his CEO equity compensation to charitable causes. In the Armchair Expert conversation, the mountain is no longer something to climb toward. It is a place where people end up alone.
— Brian Chesky on Armchair Expert with Dax Shepard, 2025At the bottom of the mountain, you have hope. But the problem is when you get to the top of the mountain oftentimes you are at the top by yourself, disconnected.
He traced the isolation back through the company's own history. The three founders, he said, had been "like family." As CEO he felt guilty spending time with them instead of on the business. "Whenever I would make time with friends and family, the guilt was I wasn't working on the company." Working up to eighteen hours a day, he became the boss of his friends, and with that came "a power imbalance." The people working for him had families of their own. He had a company, which, as he had already admitted on a podcast, was not a family.
The founding group has since come apart. Blecharczyk became chief strategy officer in 2017 and still holds the job. He built the City Portal for regulators and the screening technology that enforces the 2022 party ban, and with his wife, a neonatologist, he still hosts guests himself. Gebbia stepped back from his operating role in July 2022 and remains on the board. When he announced it, Chesky wrote to employees that "to understand Joe is to understand the soul of Airbnb" and called him "the OG host." Gebbia joined Tesla's board that September. In February 2025 he joined the Department of Government Efficiency. That August, by executive order, he became the country's first Chief Design Officer, charged with making government websites feel, as he put it, like an "Apple Store." His appointment set off calls to boycott the company he co-founded, and in April 2025 he left the board of Airbnb.org, the nonprofit that houses refugees and people displaced by disasters, after controversy over comments about refugees and migration. He gave at least $2 million to a political action committee supporting Andrew Cuomo in New York's 2025 mayoral race, and Zohran Mamdani publicly accused him of promoting "vile and racist messages about immigrants." The cofounder who had once opened his door to a broke friend, and then to three strangers from Utah, Boston, and India, was now arguing in public about who should be let into the country. Chesky has not said much about it. The record suggests that the man who told the board of directors' story in terms of trust could not make his own partnership hold together through it.
Chesky is forty-five now. He sketches and keeps bonsai, which take decades of patient work to shape. In 2026 he told Debbie Millman that "artists and designers aren't just communicators. We can actually be change agents," and that "our canvas isn't necessarily 18 by 24 inches. It can be the whole world." The company he runs is in more than 220 countries and regions. It has paid hosts more than $380 billion, including about $15,600 to the typical American host in 2025. It has remitted more than $18 billion in taxes. It holds 9 million listings, more than any boy who redrew sneakers from a catalog could have imagined. He holds 31.9 percent of the votes that decide its future.
None of this resolves the problem the story keeps returning to: the man who sold belonging and was lonely at the top. It may not be a problem that resolves. What can be said is where it started. Before the investors, the cereal, the cockroaches, and the boat on the napkin, a doorway on Rausch Street led into a room full of post-it notes and doors laid sideways as desks. A sign said to take your shoes off. In the morning a stranger in a crimson jacket was typing in the corner, and on a brown leather couch, with his rent unpaid, a twenty-six-year-old from Niskayuna was asleep in someone else's home.
Part IIThe Playbook
What follows are twelve principles drawn from the record of how Brian Chesky built, nearly lost, and rebuilt Airbnb. None of them is presented as a universal law. A few are things he has had to unlearn, and at least one is still unsettled. They are offered as patterns that keep recurring in the evidence, with the cost of each made explicit.
The principles
- 1.Treat trust as a design problem, not a marketing problem.
- 2.Find the hundred before you court the million.
- 3.Become your own most demanding customer.
- 4.Be shameless in apprenticeship.
- 5.Draw the waterline, and know what lives above it.
- 6.Turn every apology into infrastructure.
- 7.Pay your partners before they ask.
- 8.Cut once, cut deep, and write the letter yourself.
- 9.Don't call the company a family.
- 10.Start hands-on and give ground grudgingly.
- 11.Shrink the problem until someone can love it.
- 12.Institutionalize your intentions before the cement hardens.
Principle 1
Treat trust as a design problem, not a marketing problem
The original objection to Airbnb, strangers will never trust one another, was a claim about human nature. The founders, trained as designers rather than engineers or marketers, treated it as a claim about interfaces. Trust, in their view, could be built from parts: identity verification, insurance up to $1 million, payments held by a third party, and above all a review system in which neither side sees the other's verdict until both have given theirs. Blecharczyk has called the bidirectional review "the single most powerful thing" the company built. It mattered less as a record of past behavior than as an incentive for present behavior. Because everyone knows a review is coming, everyone behaves.
The same approach explains the discrimination fix in 2016. When hosts were rejecting guests with names that suggested they were Black, the problem was partly that the interface had given hosts the information to act on prejudice before committing. Hiding guest photos until after acceptance was a design change aimed at a moral failure. It did not end discrimination, but it changed the decision hosts were being asked to make.
The broader lesson for operators is that the barriers to adoption that look most like psychology are often problems in how a decision is structured. When you change the order in which information arrives, or make the consequences visible ahead of time, people will often do things they swore they never would.
Tactic: Write down the single sentence of disbelief your product faces, then list every point at which a user gets information or makes a commitment, and redesign that order so good behavior is the easiest path.
Principle 2
Find the hundred before you court the million
Paul Graham's advice in early 2009, "It's better to have 100 people love you than a million people that sort of like you," is the most-quoted sentence in Chesky's career, and he has kept applying it at every stage. In 2009 it sent the founders to New York, where they had about a hundred customers, to knock on doors and photograph apartments themselves. Fifteen years later it drives Project Hawaii, which pilots a product in one city with a team of ten or twelve before expanding to ten cities and then industrializing. Chesky cites Paul Buchheit's handling of Gmail, which shipped only after a hundred Google employees loved it, as proof that intense affection in a small sample predicts mass adoption.
The principle is easy to accept and hard to follow, because the incentives push the other way. Investors want breadth, dashboards reward reach, and a million mild users look like progress. Chesky's admission that Airbnb spent sixteen years failing to launch a second hit "because it kept trying to scale globally on day one" is the evidence. He knew the principle, practiced it once, and then forgot it for a decade and a half.
Tactic: Before any launch, name the specific hundred people whose love would prove the product works, and do not expand until you can describe, user by user, why they would be upset to lose it.
Principle 3
Become your own most demanding customer
From 2010 to about 2013 the chief executive of Airbnb had no home and slept in listings booked on his own platform. It looks like a stunt, but it was mainly a way of getting information. No dashboard reports how a lock feels in the rain, what a check-in message sounds like at midnight, or how a stranger's hallway smells. During the pandemic he reportedly listed his own home on Airbnb to understand hosting better. He tested his own Experiences in a Topanga yurt without cell service, with an outhouse for a toilet.
The pattern runs from the first night of the company, when Chesky was simultaneously the guest who could not pay rent and the host who rented out the mattresses. Founders who use their product only in demos learn what the product is supposed to do. Founders who depend on it learn what it actually does.
The cost is real. Living in the product also means having no fixed place outside it, and Chesky's later talk of isolation suggests that this kind of immersion, kept up long enough, becomes a way of life. Use it on purpose and for a limited time.
Tactic: Schedule a recurring stretch, at least a week per quarter, in which you rely on your own product for something you actually need, with no special access and no staff smoothing the way.
Principle 4
Be shameless in apprenticeship
"Be shameless," Chesky told the Oxford Union. "I was shameless to seek out people that could help me every step of the way." The list is deliberately mixed: Buffett, Iger, Ive, Weiner, Benioff, Thiel, a former CIA director, a boutique hotelier, a former president, and, through books, Jobs, Disney, Shaw, and Eisenhower. The point is not the prestige of the names. Each was chosen for one specific problem. Tenet supplied a model for allocating a CEO's attention. Conley supplied the hotel industry's knowledge of hospitality. Ive and Asai supplied an account of how Jobs actually worked day to day, which Chesky could not get from the biographies.
He picks the person who has already solved the narrow problem he faces, whatever field they come from, and asks for a meeting. Most people find this slightly embarrassing, which is why few do it.
Tactic: For the hardest problem you face this quarter, identify the person alive who has solved its closest analog, in any industry, and ask for one specific conversation about that one problem.
Principle 5
Draw the waterline, and know what lives above it
The napkin drawing from 2015 gives the CEO two jobs. The first is to watch everything below the waterline, anything that could sink the ship. The second is to own two or three areas personally, chosen because the CEO cares about them deeply and can add something nobody else can. For Chesky these were product, brand, and culture. Everything else is delegated until it starts to leak.
The model held up well during growth and failed in 2019, when it left Chesky feeling that "the car had no steering wheel." That failure refines the principle rather than refuting it. A waterline only works if the captain can see below it, and that requires enough involvement in the delegated areas to recognize a leak before it becomes a hole. Founder mode, examined closely, is the waterline model with the delegated areas watched far more closely than before.
⚓
Two Theories of the Captain
How Chesky's management model shifted between 2015 and the post-pandemic company.
| Question | The 2015 waterline model | The post-2020 model |
|---|---|---|
| Default posture toward delegated areas | Empower leaders; intervene only on leaks Delegate | Review details; give ground grudgingly Engage |
| CEO's owned areas | Product, brand, culture | Effectively all product work, for two to three years |
| Organizational shape | Divisions and growing layers | "Fiefdoms" removed; fewer layers Simplify |
| How new products launch | Scale globally on day one | One city, then ten, then industrialize |
| Characteristic failure | "The car had no steering wheel" (2019) Risk | Accused of micromanagement; bottlenecked on one person Risk |
Tactic: Draw your own boat this week: list the three things that could sink the company and the two or three you will personally own, and identify which delegated area you could no longer evaluate yourself if asked tomorrow.
Principle 6
Turn every apology into infrastructure
The 2011 vandalism case was the first test of Chesky's judgment as CEO, and he failed it. His public account was contradicted by the host who had been harmed. The recovery is the instructive part. He wrote a second public message admitting the failure, and he backed it with things that would last: an expanded customer-service team, a fund for damaged hosts, and in May 2012 the $1 million Host Guarantee. In Gallagher's account, he regarded the episode as a "rebirth."
An apology made only of words fades quickly. One backed by a new policy, budget, or team keeps working long after the news has moved on, and it is evidence the apology was meant. Chesky's sense of what counts as making amends comes from industrial design: a remedy is something you build.
Tactic: Whenever you apologize publicly, attach at least one durable commitment, such as a policy, a fund, or a team, that would still exist if nobody remembered the apology.
Principle 7
Pay your partners before they ask
The March 30, 2020 letter to hosts is a model of how to handle a partner you have wronged. It names the decision (full refunds for guests). It defends the decision on its merits ("not a business decision, but based on protecting public health"). It apologizes specifically for the process rather than the outcome ("I'm sorry that we communicated this decision to guests without consulting you—like partners should"). Then it pays: $250 million, 25 percent of normal cancellation payouts, retroactive, "covered entirely by Airbnb," plus a $10 million relief fund, $9 million of it from the founders' own pockets.
The sequence matters. Defending the decision keeps the company's credibility. Apologizing for the process admits the real fault without reopening the decision. Paying makes the word "partners" mean something. For a two-sided marketplace, in which the supply side can leave, this is not generosity. It protects the business.
⏱
The Eight-Week Rebuild
Key decisions in Airbnb's 2020 crisis, in sequence.
Feb 2020
Business in China falls roughly 80%; decline spreads from Asia to Europe.
Mar 11, 2020
WHO declares a pandemic; Airbnb allows full guest refunds, including its own fees.
Mar 15, 2020
Emergency Sunday board meeting, the "Ides of March."
Mar 30, 2020
Letter to hosts: apology for the process, $250M in payouts, $10M Superhost Relief Fund.
Apr 2020
$1B equity at $18B valuation plus $1B debt at 9–11.5% from Silver Lake and Sixth Street; Online Experiences launched.
May 5, 2020
About 1,900 employees, roughly 25%, laid off with extended health coverage and a public alumni directory.
Dec 10, 2020
IPO priced at $68; first-day valuation about $103B.
Tactic: When a decision you would make again harms a partner, defend the decision, apologize for the process, and attach a payment big enough to cost you something.
Principle 8
Cut once, cut deep, and write the letter yourself
Chesky has described the right way to do mass layoffs, in Adam Grant's summary, as "cut deep": one decisive reduction instead of repeated rounds that keep the remaining staff afraid. Airbnb cut about a quarter of its workforce in a single action. The cut was severe but humane in its details: extended health coverage, a public directory to help departing employees find work, and a letter Chesky wrote himself. He says he reviewed every name.
What he says now about the letter is as useful as the letter. He believed other companies' formal termination notices were "pretty inhumane," as though "a human being didn't write" them. His own letter was emotional, written in a hurry, and contained a sentence ("I have a deep feeling of love for all of you") that he defends as sincere but recognizes landed oddly. The right lesson is not to avoid emotion. It is that a CEO's own voice in the worst moment is worth the risk of saying something imperfectly.
Tactic: If you must reduce headcount, make one cut sized to the worst plausible scenario, fund generous transitions, and write the announcement yourself.
Principle 9
Don't call the company a family
For more than a decade Airbnb described itself as a family, and the layoffs ended that. "It is true that a company is not a family," Chesky said in 2024. "We used to refer to ourselves as a family, and then we did have to fire people... and yeah, you don't fire members of your family."
The language of family promises unconditional belonging, and no company can make that promise. When the business requires conditions, the people who believed the language feel betrayed. Chesky's revised position is more honest and still warm: a team can have "a bond that can be deeper than a typical work contract," but it is a bond between people who chose to work together and can stop. His remarks about his co-founders, that they were once "like family" and became, under him, people with "a power imbalance," suggest he learned this privately as well as at the company.
Tactic: Remove family language from your values and onboarding materials, and replace it with a description of the actual commitment, including the conditions under which it ends.
Principle 10
Start hands-on and give ground grudgingly
The core of founder mode, without the viral framing, is a reversal of the usual order. Conventional advice says delegate early and step in when something breaks. Chesky's version, refined over two to three years of reviewing every detail after the pandemic, is to begin deeply involved and hand off control only as trust is earned. He models it on Jobs, who as Chesky describes him "didn't micromanage [his employees], he partnered with them," and the test is whether a leader can actually do the work he oversees: "It's kind of like leading a cavalry, and you can't ride a horse."
The criticisms are fair and should be kept in view. A CEO can become a bottleneck. The approach depends heavily on the CEO's own judgment. And, as Chesky himself said, it is not equally available to everyone, since women founders reported that they could not operate this way without penalty. The principle is strongest when read narrowly: leaders should keep enough expertise in the product to judge it directly, and should manage "through the work, not through meetings."
Tactic: For every team you oversee, make sure you could personally review and critique its most recent piece of work in detail, and if you can't, spend time inside that work until you can.
Principle 11
Shrink the problem until someone can love it
This is the second-act version of Principle 2. Airbnb's failed attempts at a second hit, including Trips, Experiences, luxury, and business travel, shared a habit: launching everywhere at once. Project Hawaii reverses it. A team of ten or twelve, coached by the CEO, takes a product through stages ("crawl-walk-run-fly") and earns the right to scale at each one. Chesky says the first such effort added about $200 million in its first year and $400 to $500 million in its second, and that the 2025 Services launch is built on the same method.
The underlying point is that a problem small enough for one team to understand completely can be made excellent, and excellence travels better than coverage. Chesky's "11-star experience" exercise, in which a team imagines a service so far beyond five stars that it becomes absurd and then works back to what can be built, is the same idea applied to ambition: overshoot in imagination, then cut back to something buildable.
Tactic: Take your most important new initiative and cut its launch scope to the smallest geography or segment where a single team could personally know every user.
Principle 12
Institutionalize your intentions before the cement hardens
In January 2018, on the advice of an adviser he did not name, Chesky wrote down what Airbnb intended to be "if Joe, Nate and I were gone tomorrow." The resulting commitments, an "infinite time horizon" and service to "all of our stakeholders," were not just slogans. They were an attempt to fix the company's values in place while it was "big enough where anything is possible, but not so big that change would be nearly insurmountable." Other choices reflect the same instinct to make intentions binding: committing the net proceeds of his CEO equity compensation to charity, setting aside $238 million of IPO shares for hosts, and keeping founder voting control.
The record shows both the value and the limits of this. Written intentions gave the company something to measure itself against in 2020, when the $250 million host payout matched the stakeholder language. They did not prevent the reversal in the West Bank, the compromises in China, or a co-founder's public departure from the company's stated values. Written principles make a company's choices legible. They do not make the choices for it.
Tactic: Write a one-page letter, addressed to the company as if its founders were gone tomorrow, stating what you intend it to be, and revisit it every year to record where you have kept it and where you have not.
Free playbook
Get The Business Model Playbook
58 business models, one visual page each: how the money flows, the metrics that matter, and who runs it. Free when you join the Faster Than Normal email.
Free. No spam. Unsubscribe anytime.
Part IIIQuotes and Maxims
In their words
— Brian Chesky, open letter to the Airbnb community, January 2018I am absurdly lucky even to be writing this email. Ten years ago we started Airbnb. Joe and I couldn't pay rent, so we created the first AirBed & Breakfast and invited three people we'd never met to stay in our home.
— Brian Chesky, note to Airbnb employees on Joe GebbiaBefore we hosted Kat, Michael, and Amol, Joe hosted me. He not only took me into his home, but he connected me to the startup community in San Francisco. Joe was the OG host.
— Brian Chesky, letter to hosts, March 30, 2020While I believe we did the right thing in prioritizing health and safety, I'm sorry that we communicated this decision to guests without consulting you—like partners should.
— Brian Chesky on Adam Grant's ReThinking, 2024It is true that a company is not a family. In fact, we had to make that pivot.
— Brian Chesky on Design Matters with Debbie Millman, 2026The world can be our canvas. Our canvas isn't necessarily 18 by 24 inches. It can be the whole world.
Maxims
- Disbelief is a design brief. When people say strangers will never trust each other, change the order in which they learn about each other.
- A hundred lovers beat a million likers. Small, intense devotion predicts large adoption better than broad, mild approval.
- Depend on what you sell. The founder who relies on the product learns what no dashboard reports.
- Ask anyone, shamelessly. Find whoever, in any field, has already solved your narrowest problem.
- Watch below the waterline. Delegate everything except what could sink you and the two or three things only you can do.
- An apology should leave something behind. Back every admission with a policy, a fund, or a team.
- Partners are paid, not praised. The word "partner" means as much as the check behind it.
- Cut once and write the letter. One deep cut, delivered in your own voice, does less damage than a series of small ones.
- A company is not a family. Describe the real bond, including how it ends.
- The summit is lonely by design. Decide in advance who will still be with you when you get there.
