Brian Chesky has helped Airbnb bounce back from many obstacles — and built his Silicon Valley legacy along the way.

The now-43-year-old CEO majored in industrial design at the prestigious Rhode Island School of Design and also dabbled in hockey and bodybuilding in his 20s.

After graduation, an idea he hatched with his San Francisco roommate Joe Gebbia blossomed into tech unicorn Airbnb, which has positioned Chesky as one of Silicon Valley's key players.

As of August 2024, Airbnb is worth nearly $73 billion. It had its first profitable year in 2022, and has become synonymous with short-term rentals across the US.

Still, the company's stock fell a record 14% in the second quarter of 2024, and Airbnb noted in its earnings call that travelers aren't booking as many stays.

Chesky owns an estimated 11% of the short-term rental giant. His current net worth is $7.9 billion, according to Forbes, which also ranked him as one of the most eligible billionaires in the world alongside Kim Kardashian and Elon Musk.

Here's how Brian Chesky, an upstate New York native, became one of the richest young tech founders in America.

Chesky grew up in Niskayuna, New York, north of Albany. He was into hockey, and he also liked to draw and design new versions of Nike sneakers, which turned into an interest in art.

Chesky's high school yearbook quote was, "I'm sure I'll amount to nothing." He thought it was funny — his dad didn't.

In 1999, Chesky attended Rhode Island School of Design, where he served as captain of the hockey team and studied industrial design.

At RISD, Chesky met Joe Gebbia, with whom he would eventually cofound Airbnb. 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," Fortune reported.

He eventually moved to San Francisco and in with Gebbia, but the two unemployed grads soon ran out of cash.

Then, 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 — a "designer's bed and breakfast."

The roommates ended up housing three people that weekend, offering up air mattresses and floor space, as well as Pop-Tarts for breakfast.

A few months later, Gebbia and Chesky were joined by their engineer friend, Nathan Blecharczyk. Together, the three guys started what was then called Airbedandbreakfast.com in August 2008. Chesky "gravitated naturally to the role of leader," Fortune wrote in 2015.

Since then, Airbnb has not only shortened its name but has listings in more than 220 countries worldwide. The company has served an estimated 1.5 billion guests since its 2008 launch.

In 2015, Chesky was named as one of the most influential people alive in Time 100. Apple's former design chief, Jony Ive, wrote at the time that Chesky's "audacity is fabulous."

Chesky is not married, though he was previously in a relationship with artist Elissa Patel. He has two golden retrievers named Sophie and Sandy.

Fast forward to February 2020, when cancellations began rolling in due to a mysterious virus. Chesky and his team were three weeks away from filing for Airbnb's IPO.

The early days of the pandemic seemed grim. 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.

Airbnb laid off 1,900 employees, about 25% of its full-time staff. 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.

He reflected on the firings during an appearance on The Diary of a CEO podcast with Steven Bartlett in 2023.

"This is how I want to be remembered. I only remember that when I'm in peril, we're in our darkest hour, I'm not just worrying about how we will survive, I'm trying to call CEOs of other companies to see if they can hire our people," Chesky said.

But then travelers burned out from lockdown turned to Airbnb over traditional hotels. Bookings bounced back by as much as 127% between April 2020 and May 2020.

Airbnb went public on December 10, 2020, under the Nasdaq ticker symbol ABNB. 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.

Between 2020 and 2022, when interest rates were relatively low, many people bought homes to use as investment properties, planning to rent them out on Airbnb and other short-term-rental sites to help cover their mortgages or simply make extra money.

Demand for travel and experiences surged— so much so that Airbnb recorded its first profitable year in 2022, with a $1.9 billion profit. (It lost $352 million in 2021.)

Chesky and Airbnb's two other cofounders publicly signed the Giving Pledge in 2016, a philanthropic initiative started by Warren Buffett, Bill Gates, and Melinda French Gates. By doing so, they promise to donate more than half of their wealth within their lifetimes.

In 2022, Chesky personally donated $100 million to the Voyagers Scholarship run by former President and First Lady Obama, which awards $50,000 in tuition for college juniors pursuing public service. Airbnb provides housing to recipients for summer internships and post-grad travel.

When Russia invaded Ukraine in February 2022, Chesky announced the company would work to house 100,000 refugees with free two-week stays.

In November 2022, Chesky listed a guest room in his home on Airbnb, featuring 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 told outlets he would make cookies and go to the gym with guests.

Countless other real-estate firms conducted mass layoffs due to the cooling housing market. In March 2023, Airbnb cut 30% of its recruiting staff, representing 0.4% of its total headcount of 6,800.

In August — amid protests from locals — Barcelona said it would push to fully ban and eliminate all of its registered short-term rental listings by 2028. Elsewhere, cities like New York, Tokyo, and Vancouver now require hosts to live in the units they're renting out.

During its Q2 earnings call, Airbnb told investors that its marketing costs would grow faster than revenue in Q3.

"Kicking up marketing spend at a moment when demand is softening tends to be the ultimate backbreaker for an internet stock in our experience," analysts from RBC wrote in a note.

This story was originally published in 2016. It was last updated in September 2024.