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.

I remember the day my dad saw my yearbook photo. He saw this and yelled, "Nothing?! Nothing?!" I thought it was funny... he 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. Now, off to Rhode Island School of Design. ✈️ 🎓See you soon Dad! #RISD

A post shared by Brian Chesky (@bchesky) on May 31, 2017 at 11:06am PDTMay 31, 2017 at 11:06am PDT

"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.

—Bill Gross (@Bill_Gross) February 16, 2016

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 in 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. Airbnb has a market cap of $89 billion as of March 2025.

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 donate more than half of their wealth within their lifetimes. The pledge is a philanthropic initiative started by Warren Buffett and Bill and Melinda French Gates.

But after getting 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 Feburary, 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.

Forbes also 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 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."