The decision to adopt this nomadic lifestyle is partly a celebration of travel opening up after two years of subdued tourism. Airbnb was thrown into crisis in the early months of coronavirus, before enjoying record sales during the first quarter of this year. In the first three months of 2022, 102 million nights were booked on the website. Today, 4 million hosts rent out rooms or properties in over 220 countries and regions. The only places one cannot rent an Airbnb today are Iran, Syria, Crimea and North Korea, and – currently – Russia and Belarus.
However, Chesky’s commitment to personal travel is also a test of his idea that his employees and millions of other workers will be able to do their jobs from anywhere in the world.
“You can run a nearly $100bn (£82bn) company from a laptop in other people’s homes,” he says. “It’s possible – and if I can do it, a lot of people can do it.”
Last month, Chesky announced that Airbnb’s 6,000 staff would be able to work from anywhere – a vow that comes amid a heated debate about the future of the office. And last week, the company unveiled an overhaul of its app designed to send travelers to areas outside of major tourist hubs.
Chesky founded Airbnb in 2007 when, as a young graduate working as an industrial designer in San Francisco, he and his roommate Joe Gebbia couldn’t afford their rent one month. The pair bought three air mattresses and rented out space in their apartment to visitors in the city for a conference, marketing the idea as “Airbed and Breakfast”. They charge guests $80 a night (around £90 today); one of the meeting rooms in the firm’s San Francisco headquarters is modeled on the apartment that launched the business.
Chesky and Gebbia, along with former roommate Nathan Blecharczyk, decided to turn the idea into a company, and attracted Silicon Valley investors when they raised money by selling limited edition breakfast cereal boxes (‘Obama Os’ and ‘Cap’n McCains’) during the 2008 presidential election.
The founders were encouraged to “blitzscale” their way to world domination. Airbnb, as it became known, became relentlessly popular, but clashed along the way with hotel groups, city governments and critics who accused it of hollowing out communities and pushing up housing prices.
More has changed in the last two years than in the preceding decade, however. In the early days of the pandemic, travel slumped to an almost-total standstill. Airbnb was forced to refund millions of tourists, enraging its millions of hosts who were left with empty houses, while the company’s own revenues collapsed.
“We were doing $40 billion [in bookings] and we lost 80 per cent of it overnight. No one had really ever lost that much business and lived to tell about it,” says Chesky, who talks at the rapid clip of someone who has more to say than time in which to say it. “I never thought we were near death, but I did stare into the abyss.”
In May 2020, Chesky tearfully laid off thousands of staff over Zoom and borrowed billions in an attempt to hibernate through Covid. Yet within weeks, the unexpected started to happen: people ventured out of their homes and started traveling again. Instead of flying to urban hotels as before, they were escaping cities and staying in treehouses, mountain chalets and lake houses.
Many were doing so for weeks or months, no longer tethered to an office. Airbnb’s business rebounded enough that by the end of that year, the company pulled off the year’s biggest initial public offering. On the first day of Wall Street trading in December 2020, it was valued at more than $100 billion and Chesky was worth more than $10 billion. A clip of Chesky went viral when CNBC told him the latest stock price on live television, causing his eyebrows to virtually hit the ceiling.
Pandemic winners from Peloton to Netflix mistakenly believed the Covid-19 crisis had changed their worlds forever, for the better, only to now slip into reverse. But Chesky is steadfast in his belief that his industry is not going back.
“I think we’re probably experiencing, at the macro view, the biggest change to travel, maybe since the Second World War,” he says. “After the war, you had highways and you had mass transportation. The pandemic was either the biggest change since then or the second biggest change after the advent of the internet.
“When borders were closed and when people weren’t traveling for business and they weren’t going to big cities, they were forced to basically discover other things and a lot of people discovered the outdoors and other communities. Now the genie’s out of the bottle. I think people now realize there’s not 100 places to go, there’s 100,000 places to go.”
Airbnb’s overhaul this week – what it calls the biggest change to travel websites in 25 years – is a reflection of this shift. Instead of asking people to enter a destination and dates, users select from categories such as mansions, castles, national parks or vineyards, and scroll through Instagram-worthy homes instead of worrying about where they are. They are just as likely to end up in Portsmouth as Paris.
Chesky says the aim is partly to redistribute travellers, tackling claims that Airbnb contributes to overtourism. His decision by him is likely to be music to the ears of residents of places such as St Ives, which last week rebelled against tourists by starting to charge them to use its public lavatories. Airbnb has also been accused of spoiling parts of the Lake District where rental properties outnumber locals ten-to-one.
Chesky says he is seeking to avoid overloading rural hotspots. “My hope is they don’t all go to Cornwall, they don’t look all in one place. [Overtourism] is even worse if you think of small towns because you can overwhelm them faster, so this is our attempt at addressing it,” Chesky says.
“We want everyone to be distributed rather than everyone going into one small community.”
He argues that towns and villages should not shut themselves off to tourists completely, however. “My opinion is that outsiders and travelers are good, but it’s like a recipe. And you want most communities to be mostly locals, with some outsiders, and when there are too many outsiders there is no community.
“But when there’s no outsiders, I mean, think about those kinds of committees. They’re xenophobic; they’re not open to new ideas. Those aren’t really healthy communities either. I think you want a mix, I don’t know what the perfect ratio is.”
Chesky is already unpopular enough among the world’s hoteliers, whose businesses have been squeezed by Airbnb’s rise. He now predicts that coming out of the pandemic, hotels will be far worse hit than Airbnb by a collapse in business travel, much of which will become redundant due to Zoom.
“For many decades, business travel basically fueled almost all profits for hotels and airlines. All those economy seats are only possible because of the first class seats paying for them,” he says. “Your company pays for you to travel for business and you get to pocket your points. They’re like personal subsidies. That’s a racket that’s basically gone now.”
Chesky distances himself from much of the Silicon Valley set. He is a designer at heart, rather than a coder. He is close to Sir Jony Ive, the British creative mind behind the iMac and iPhone, and former Burberry chief Angela Ahrendts sits on the company’s board.
He has a fellowship of advisers including Barack Obama and former American Express boss Ken Chennault, whom he says have helped him manage the delicate balance between hosts, guests and the places people visit – although he says he would like Elon Musk’s help on dividing up time .
“He has five companies and six children, and I have one company and no children,” Chesky says. “So he’s beating me by like 11 to one. He’s going to go down as a historical figure like Steve Jobs or Henry Ford.”
Chesky is unmarried and admits his wandering lifestyle isn’t for everyone, especially those tied to physical workplaces or schools.
“When I do have a family, I’m not going to live nomadically. In fact, this is one of the reasons I’m doing it is because I’m at a point in my life where I can do this. When I tell people the world’s flexible, I am living an extreme version of that.”
But while he may not live on Airbnb forever, Chesky and his staff have largely said goodbye to the office. In the future, Chesky thinks many of his customers will not be tourists so much as workers on the go, no longer tied to a physical workplace from Monday to Friday.
“More and more of us have jobs that can be done from a laptop. And so the question is, does the laptop need to be tethered? Or can the laptop move with you?”