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The rise of Airbnb CEO Brian Chesky, who got his start renting out air mattresses on his floor and is now headed toward a highly anticipated IPO

The rise of Airbnb CEO Brian Chesky, who got his start renting out air mattresses on his floor and is now headed toward a highly anticipated IPO
  • Brian Chesky didn't take a traditional route into the tech world: he's a former hockey player who studied industrial design in college.
  • He and cofounder Joe Gebbia had the idea for Airbnb in 2007: When a design conference came to town and all the hotels were booked up, they decided to rent out their apartment for those who needed a place to stay.
  • Airbnb, then called Airbedandbreakfast.com, officially launched in August 2008. Now, 12 years later, Airbnb is headed toward an initial public offering.
  • Chesky, Airbnb's CEO, is worth an estimated $3.1 billion these days.

Brian Chesky didn't know much about tech before starting Airbnb.

The now 39-year-old CEO majored in industrial design in college, and dabbled in hockey and bodybuilding in his 20s. But now, he's grown an idea that stemmed from overbooked hotels into a multi-billion-dollar startup, and has become one of Silicon Valley's key players.

On Monday, Airbnb publicly revealed its paperwork for an initial public offering, slated to be one of the most highly anticipated IPOs of the year.

Here's how the 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 Nike sneakers, which turned into an interest in art.

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

Source: Fortune

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Chesky's high school yearbook quote was "I'm sure I'll amount to nothing." 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!"

 

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

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

Source: Fortune

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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."

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."
Airbnb cofounder Joe Gebbia. Airbnb

Source: Fortune

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In his early 20s, Chesky was a competitive bodybuilder. He was described in a 2014 profile as still having "16-inch biceps."

In his early 20s, Chesky was a competitive bodybuilder. He was described in a 2014 profile as still having "16-inch biceps."
Brian Chesky, on the left. Kevork Djansezian/Getty

In a 2014 Fast Company profile, Chesky is described as an imposing figure: "A former hockey player and bodybuilder with 16-inch biceps, the CEO commands attention. His boomerang grin and slant nose work to sharply focus his attention on you. Rather than turn his head toward me, he physically picks up his chair and pivots it directly so we're eye to eye."

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

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

Source: Forbes

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But shortly thereafter, he moved to San Francisco and in with Gebbia. The two unemployed grads soon ran out of cash. 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 "designers bed and breakfast."

Source: Fortune

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

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

Source: Fortune

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

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

Source: Fortune

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Since then, Airbnb has not only shortened its name, but has listings in more than 191 countries worldwide. The company has served an estimated 800 million guests since its 2008 launch. Airbnb was last valued at $18 billion, making it one of the most valuable startups in the US.

Since then, Airbnb has not only shortened its name, but has listings in more than 191 countries worldwide. The company has served an estimated 800 million guests since its 2008 launch. Airbnb was last valued at $18 billion, making it one of the most valuable startups in the US.
Glassdoor/Airbnb

Source: Airbnb, Business Insider

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Now 39, Chesky's net worth stands at $3.1 billion. It's unclear how much of a stake Chesky owns in Airbnb, but it's estimated at just under 15%.

Now 39, Chesky's net worth stands at $3.1 billion. It's unclear how much of a stake Chesky owns in Airbnb, but it's estimated at just under 15%.
Chris Weeks/Getty

Source: Forbes

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

In 2015, Chesky was named to the Time 100 as one of the most influential people alive. Apple's former design chief, Jony Ive, wrote at the time that Chesky's "audacity is fabulous."
Brian Chesky, Chief Executive Officer of Airbnb smiles during a session at the annual meeting of the World Economic Forum (WEF) in Davos January 23, 2014. REUTERS/Denis Balibouse
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Chesky is not married, though he was previously in a relationship with artist Elissa Patel. Chesky has a golden retriever named Sir Richard Parker who hangs out at Airbnb headquarters and accompanies him on road trips.

Sir Richard Parker @airbnb.

A post shared by Brian Chesky (@bchesky) on May 10, 2015 at 10:08am PDT

 

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

In 2016, Chesky, as well as Airbnb's two other cofounders, all publicly signed the Giving Pledge, a philanthropic initiative started by Warren Buffett and Bill and Melinda Gates. By doing so, they promise donate more than half of their wealth within their lifetimes.
From left: Airbnb cofounders Brian Chesky, Nathan Blecharczyk, and Joe Gebbia. Airbnb
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Up until 2016, Chesky was still renting out his couch in his San Francisco apartment on Airbnb. 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.

Up until 2016, Chesky was still renting out his couch in his San Francisco apartment on Airbnb. 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, co-founder and CEO of AirBnb, attends the Reuters Global Technology Summit in San Francisco Thomson Reuters
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While he remains CEO, Chesky handed over daily operations of the company to Blecharczyk in 2014. These days, Chesky remains focused on Airbnb's future moves.

While he remains CEO, Chesky handed over daily operations of the company to Blecharczyk in 2014. These days, Chesky remains focused on Airbnb's future moves.
Airbnb CEO Brian Chesky Kimberly White/Getty Images for Fortune

Source: Vanity Fair

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Airbnb announced in September 2019 that it planned to go public in 2020.

Airbnb announced in September 2019 that it planned to go public in 2020.
Mike Windle/Getty

Source: Business Insider

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But its IPO was a question mark for much of 2020 after the coronavirus pandemic hit: in early March, Airbnb's revenue plummeted 80% due to virus-related travel restrictions. Airbnb 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.

But its IPO was a question mark for much of 2020 after the coronavirus pandemic hit: in early March, Airbnb's revenue plummeted 80% due to virus-related travel restrictions. Airbnb 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.
AP

Source: Business Insider, Business Insider

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Airbnb laid off 1,900 employees, about 25% of its full-time staff, and hundreds of contractors. The move was met with frustration from employees who said they felt betrayed by the decision, but Chesky was also praised for his handling of the layoffs: employees were given generous severance packages and Chesky offered to help find them jobs elsewhere.

Airbnb laid off 1,900 employees, about 25% of its full-time staff, and hundreds of contractors. The move was met with frustration from employees who said they felt betrayed by the decision, but Chesky was also praised for his handling of the layoffs: employees were given generous severance packages and Chesky offered to help find them jobs elsewhere.
Employees at Airbnb's headquarters. Gabrielle Lurie/Reuters
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Over the past few months, things have started to turn around for Airbnb as people have begun to rethink how they travel. Though the pandemic decimated Airbnb's business in the first several months of the year, the company is forging ahead with its IPO.

Over the past few months, things have started to turn around for Airbnb as people have begun to rethink how they travel. Though the pandemic decimated Airbnb's business in the first several months of the year, the company is forging ahead with its IPO.
Mike Cohen/Getty Images for The New York Times

Source: Business Insider, Business Insider

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