Most great business ideas start in garages, dorm rooms, or tech labs. Brian Chesky’s idea? It started with an air mattress. What began as a way to make a little extra rent money turned into Airbnb, one of the biggest hospitality companies in the world. But the journey wasn’t easy—Chesky had to navigate skepticism, near-bankruptcy, and even a global pandemic to turn his vision into reality.
From aspiring artist to accidental entrepreneur
Brian Chesky was born in 1981 in Niskayuna, New York. Unlike most tech founders, he didn’t grow up obsessed with computers or coding. Instead, he loved art and design, which led him to study industrial design at the Rhode Island School of Design (RISD).
After graduating, Chesky moved to San Francisco with his college friend Joe Gebbia. They were both struggling to pay rent when they noticed that a big design conference was coming to town, and all the hotels were fully booked. That’s when they had a simple but crazy idea: What if they rented out air mattresses in their apartment to visitors who needed a place to stay?
They called it “Air Bed & Breakfast”, and within days, they had three guests sleeping on their floor, paying $80 a night. The experience showed them that people were willing to pay for something more personal than a hotel—a real home, hosted by real people.
From cereal boxes to Silicon Valley
Chesky and Gebbia knew they had something special, but turning an air mattress rental into a real business was another challenge. They brought in a third co-founder, Nathan Blecharczyk, a tech-savvy engineer, to help build a proper website.
But even with a working platform, investors weren’t interested. Venture capitalists didn’t think strangers would ever trust each other enough to stay in each other’s homes. Meanwhile, Chesky and his team were running out of money.
Desperate for funds, they came up with a creative way to survive: they designed and sold limited-edition cereal boxes—“Obama O’s” and “Cap’n McCain’s”—during the 2008 U.S. election. The gimmick brought in $30,000, just enough to keep Airbnb alive a little longer.
Their persistence paid off. In 2009, they finally caught the attention of Paul Graham, the legendary startup mentor behind Y Combinator. He saw their potential, invested in them, and helped them refine their ideas. That was the turning point—soon after, Airbnb started taking off.
Disrupting the hotel industry
As Airbnb grew, it challenged the entire hospitality industry. Hotels had been the only real option for travelers, but now, Airbnb was offering something completely different: unique homes, personal experiences, and often, cheaper prices.
By 2011, the company was expanding internationally. Within a few years, Airbnb wasn’t just for cheap stays—it was becoming a premium travel brand, offering everything from budget-friendly apartments to luxury villas.
The struggles of success
Despite Airbnb’s meteoric rise, Chesky faced major challenges. Cities started pushing back, arguing that Airbnb was driving up housing prices and violating hotel regulations. The company also faced trust issues—what if guests trashed a home? What if hosts were unsafe? Chesky responded by introducing a $1 million host guarantee and strict safety policies.
Then, in 2020, the COVID-19 pandemic nearly crushed Airbnb overnight. Travel stopped. Bookings disappeared. The company lost 80% of its business in just a few weeks. Chesky had to make painful decisions, including laying off 25% of Airbnb’s workforce.
But instead of giving up, he adapted. He shifted Airbnb’s focus to local travel and long-term stays—catering to people who wanted a change of scenery while working remotely. The strategy worked, and by 2021, Airbnb was not only surviving but thriving again.
A new kind of CEO
Chesky is different from the typical tech billionaire. He still lives in Airbnb homes instead of owning a house, and he’s deeply involved in the company’s design and culture. His leadership has made Airbnb one of the most influential brands in travel, proving that the best business ideas don’t always come from business school—they come from solving real problems in creative ways.
From renting out an air mattress to running a multi-billion-dollar company, Brian Chesky’s journey shows that the craziest ideas can sometimes change the world.
