This US entrepreneur quit a stable job, bought air mattresses to rent out his apartment with breakfast included and the idea became Airbnb, now an ₹83.74 billion business

Brian Chesky had what many people dream of. A secure, well-paying design job with benefits. But instead of staying on the safe path, he quit, moved to San Francisco with little money, and took a chance on an idea born out of struggling to pay rent.

What began as "Air Bed & Breakfast" soon evolved into Airbnb, a company that has grown into an ₹83.74 billion business and made Chesky one of the world's most successful entrepreneurs. AirBnb transformed the travel industry and making Chesky one of the world's most successful entrepreneurs.

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Brian Chesky left a comfortable career because he wanted something bigger

Before becoming an entrepreneur, Brian Chesky worked as an industrial designer in Los Angeles. In an interview with Startups.com, Chesky recalled experiencing what he described as a "weird feeling of mortality." The daily commute and office routine made him question whether that was really the future he wanted.

He said: "This is my life." Chesky explained that after studying at RISD, where students were encouraged to believe that designers could change the world, his corporate job felt like a major letdown.

Instead of continuing down that path, he resigned, packed a foam bed into his Honda Civic, and drove to San Francisco to live with his college friend Joe Gebbia.

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The idea for Airbnb came from being unable to pay rent

When Chesky arrived in San Francisco, money was running out. He reportedly had around $1,000 in his bank account while his share of the rent was even higher. Around the same time, a major design conference was bringing thousands of visitors to the city, and nearly every hotel room had sold out.

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Joe Gebbia suggested an unusual idea. Instead of looking for another job immediately, they would inflate a few air mattresses in their apartment and rent the space to conference attendees. They even planned to provide breakfast.

That simple idea became "Air Bed & Breakfast," the business that would later evolve into Airbnb.

Their startup almost failed before it became a success

The early years were anything but glamorous. Chesky and his co-founders struggled to convince investors that strangers would ever pay to stay inside someone else's home. They accumulated thousands of dollars in credit card debt and faced repeated investor rejections.

To keep the company alive, the founders even sold specially designed cereal boxes tied to the 2008 U.S. presidential election, raising enough money to continue building the business.

Eventually, Y Combinator accepted Airbnb into its startup accelerator, providing funding and mentorship that helped the company grow.

Brian Chesky personally visited hosts to understand the business

Rather than relying only on data, Chesky believed in learning directly from customers.

As Airbnb struggled to gain traction in New York City, he and Joe Gebbia traveled there and stayed with dozens of hosts to understand why bookings were low.

They discovered that many listings featured dark, low-quality photos that failed to attract guests.

Joe Gebbia later explained: "The photos were really bad. People were using camera phones and taking Craigslist-quality pictures. Surprise! No one was booking because you couldn't see what you were paying for."

The founders began taking professional photographs of hosts' homes themselves, a simple move that helped increase bookings and accelerate Airbnb's growth.

A design-first mindset helped Airbnb stand out

Unlike many Silicon Valley startups founded by engineers, Airbnb was built by designers.

Initially, that worked against Chesky. He admitted many investors viewed his background as a weakness rather than an advantage.

As he explained: "Our backgrounds were considered a liability when I got here. A lot of investors did not want to invest in us because of who I was."

Over time, however, that design-focused approach became one of Airbnb's greatest strengths, influencing everything from the user experience to the company's brand identity.

What began with three air mattresses in a San Francisco apartment has grown into one of the world's biggest travel platforms.

Airbnb now operates in countries around the globe, serving millions of guests and hosts. Brian Chesky, who once walked away from a secure design career and struggled to pay rent, has become one of the most successful entrepreneurs of his generation, with a fortune worth billions of dollars.