The rise of Airbnb CEO Brian Chesky, who got his start renting out air mattresses on his floor

He was into hockey, and he also liked to draw and design new versions of Nike sneakers, which turned into an interest in art, according to a 2015 Fortune profile.

He thought it was funny — his dad didn't.

"Earlier this year, he was happy to find out I'd be speaking at both my high school and college as the commencement speaker," Chesky wrote on Instagram in 2017. "See you soon Dad!"

The '04 grad served as captain of the hockey team and studied industrial design.

Right before graduation, Gebbia reportedly pulled Chesky aside and said: "Before you get on the plane, there's something I need to tell you. We're going to start a company one day, and they're going to write a book about it," per Fortune.

After graduating from RISD, Chesky moved to Los Angeles to work as an industrial designer, for which he made $40,000 a year, according to Forbes.

The two unemployed grads soon ran out of cash, said Leigh Gallagher, author of the book, "The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions … and Created Plenty of Controversy." When a design conference came to town in October 2007 and caused all the hotels to sell out, Gebbia pitched Chesky the idea of renting out their space to those who couldn't find a place to stay. Guests could sleep on air mattresses on their living room floor.

"They thought they were going to get hippie backpackers, and instead, they got lots of people just like them who wanted those air mattresses," Gallagher said in an interview with the "Knowledge at Wharton" show. "They had people sending their resumes and their LinkedIn profiles, so they thought, 'We might be on to something.'"

Together, the three guys started what was at the time called Airbedandbreakfast.com in August 2008.

"I think they came along at the right time, because it was the Great Recession," Gallagher said. "People were looking for a cheap way to travel, and they just struck a chord with millennials, who were a massive market that at the time was not really being spoken to by the traditional hotel industry."

The company says it has served an estimated 2 billion guests since its 2008 launch. As of May 2025, Airbnb's market cap was $78 billion.

Apple's former design chief, Jony Ive, wrote at the time that Chesky's "audacity is fabulous."

"The service that Brian and his partners imagined," the Apple executive said, "is soaringly ambitious and utterly practical."

"Bringing people together is something of a passion for Brian," Ive said. "With Airbnb, he's helped create millions of personal connections. That's an achievement that even the best hotels in the world should envy."

By doing so, they promise to donate more than half of their wealth within their lifetimes. The pledge is a philanthropic initiative started by Warren Buffett and Bill Gates and Melinda French Gates.

But after being caught flouting a San Francisco law that requires hosts to register with the city, Chesky was forced to take the listing down.

Chesky and his team were three weeks away from filing for Airbnb's IPO.

Airbnb's revenue plummeted 80% due to COVID-related travel restrictions. The company burned through its cash reserves and opted to raise $2 billion in debt and equity financing to stay afloat. Its valuation, previously $31 billion, slipped to $18 billion.

Employees said they felt betrayed, but Chesky was also praised for his handling of the situation. Workers were given generous severance packages, and Chesky offered to help find them jobs elsewhere.

Bookings bounced back by as much as 127% between April 2020 and May 2020.

Barron's called it a "blockbuster" IPO. On its first day of trading, the company was valued at $86 billion, more than hotel rivals Marriott, Hilton, and Intercontinental combined.

When Russia invaded Ukraine in February 2022, Chesky tweeted that "Airbnb and Airbnb.org are working with our Hosts to house up to 100,000 refugees fleeing from Ukraine, for free," and appealed for hosts from neighboring countries, including Poland, Germany, Hungary, and Romania, to join the effort.

The room had a queen-sized bed and a piece of Airbnb history: the novelty cereal boxes that Chesky sold in 2008 to fund the early days of the company. Chesky said he would make cookies and go to the gym with guests.

"I live here, so I'll be here," Chesky said in a video posted to his X account, which showed him taking photos of his home. "I did it 15 years ago, and I'm going to do it again."

Airbnb recorded its first profitable year in 2022, with a $1.9 billion profit. It lost $352 million in 2021, per the Wall Street Journal.

In March 2023, Airbnb cut 30% of its recruiting staff, which represented just 0.4% of its total headcount of 6,800. "We're going to continue to grow, but we're going to grow modestly," CFO Dave Stephenson said in a February earnings call.

In 2023, Forbes ranked him as one of the most eligible billionaires in the world alongside Kim Kardashian and Elon Musk.

"Why would Airbnb just offer homes? Why couldn't we offer significantly more things? And that's the future of this company," Chesky told Skift CEO Rafat Ali during the 2024 Skift Global Forum. "We're going to take the Airbnb model, and we're going to bring it to a lot of different categories."

Altman said Chesky, along with venture capitalist Ron Conway, helped him navigate challenges at OpenAI.

"They stopped me from making several mistakes and made none themselves," Altman wrote in a blog post. "They used their vast networks for everything needed and were able to navigate many complex situations. And I'm sure they did a lot of things I don't know about."

"I am reasonably confident OpenAI would have fallen apart without their help; they worked around the clock for days until things were done," he said.

Chesky said in a 2025 "Rapid Response" podcast episode that difficult deadlines and regular progress checks are more important than demanding a return to the office.

"I have a simple rule: we basically ask people to come to San Francisco one week a month," Chesky told host Bob Safian. "Some people come for just two or three days. Some people come for the full week."

"I have not found a huge value in people being in the office all the time," Chesky said. "What I want is, for the most part, people coming to the San Francisco office, but I can't get everyone to move here to San Francisco, and I can't get them to fly here every week."

But he said people have gotten the definition twisted.

On an episode of The Verge's "Decoder" podcast, the Airbnb CEO explained what he thought people were misunderstanding about it.

"First of all, people don't know what founder mode is," Chesky said on the podcast. "They think it means swagger. I remember a tweet that said, 'I'm going founder mode on this burrito.' I don't know what that means. That wasn't the message."

"If I could summarize founder mode in a couple sentences, it's about being in the details," he said. "It's that great leadership is presence, not absence."

In a recent interview with Fortune, Chesky said that while meetings are a key part of how he gets work done, the traditional one-on-one format often misses the mark.

"Almost no great CEO in history has ever done them," he said, arguing that one-on-ones tend to serve the employee's agenda, not the company's.

"When an employee owns the agenda, you become like their therapist," Chesky said.

He added that topics raised are often ones managers would prefer not to address, or ones that could benefit others if discussed in a larger meeting.

He said that one-on-ones can still be appropriate in certain circumstances, such as when a team member is dealing with a personal issue and needs privacy.

In a podcast with Michelle Obama and Craig Robinson, Chesky said there is a "silver lining" for business leaders during tough economic times.

"And the one, I don't want to say it's a good thing, but what it does is it teaches you a certain type of discipline," said Chesky, who started Airbnb during a financial crisis. "A tough economy teaches you a discipline that gets institutionalized into your culture."

He added that in the long run, the economy needs to stabilize because entrepreneurs he has spoken with recently told him "a lot of fundraising, for all intents and purposes, was kind of on hold."

"A lot of limited partners and investors are just like hunkering down. And what we know about investors, they don't like uncertainty," he said.

Chesky said he does some of his best work while the rest of the world sleeps, because as a single man with his dog at home, he can afford to go all in.

The 43-year-old told The Wall Street Journal that his creative peak hits around 10 p.m. and often stretches until he goes to bed at around 2:30 a.m.

Before diving in, he said he also tends to stick to the nightly routine of a 90-minute workout starting at 8 p.m.

"When you're CEO, you can decide when the first meeting of the day is," Chesky told the Journal.

On May 13, the company launched Airbnb Services with "10 categories in 260 cities," including chefs, massages, spa treatments, personal training, beauty services, and more.

"People choose hotels for their services. People choose Airbnbs for the space," added Chesky. "Now, we're giving you the best of both worlds—amazing homes with services that make them even more special."

Along with Services, Airbnb also relaunched Experiences and redesigned its app.

Airbnb is leaning into France as US demand softens.

Chesky announced a new three-year partnership with the Tour de France on May 22 to promote listings and experiences along the 3,339-kilometre race route.

Chesky told Reuters that France has become Airbnb's second-largest market, where local travelers make up roughly 70% of bookings and are experiencing "very healthy" growth, potentially outpacing the US, where consumer sentiment has taken a hit from trade policy uncertainty.

Chesky also hinted at more global luxury brand partnerships.

"Wealthy people like to spend money on experiences more than even things," he said.