In 2007, Brian Chesky was a broke designer living in San Francisco, struggling to pay rent on an apartment he shared with his friend Joe Gebbia. A design conference was coming to town, hotels were fully booked, and the two friends saw an opening: what if they rented out a few air mattresses on their living room floor to attendees who needed a place to stay?
They built a simple website, bought three airbeds, and called the project Air Bed & Breakfast. Three guests showed up. They shared meals, conversations, and stories — and for Chesky, something clicked. This wasn’t just a way to make rent. It was a new kind of travel built around people, not properties.
Rejected by Investors, Saved by Cereal
Over the next year, Brian Chesky and his co-founders worked tirelessly to turn the idea into a company. But investors didn’t believe that strangers would stay in each other’s homes. They were rejected dozens of times. The team maxed out credit cards, struggled to keep the company alive, and at one point sold political-themed cereal (“Obama O’s” and “Cap’n McCain’s”) just to pay the bills.
Still, Chesky held on to one belief: people crave belonging. Travel wasn’t just about accommodations — it was about connection.
Y Combinator and the Power of “Doing Things That Don’t Scale”
Their turning point came in 2009 when Y Combinator accepted them. In YC, Chesky learned a lesson that shaped Airbnb’s approach forever: “Do things that don’t scale.” He and Gebbia flew to New York to meet hosts personally, take photos of their listings, and understand what users actually needed.
Growth followed — first slowly, then rapidly.
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Building a Global Community and Surviving Crisis
As Airbnb expanded worldwide, Brian Chesky faced challenges unfamiliar to most founders: regulatory battles, safety concerns, community trust, and a near-death moment during COVID-19 when global travel came to a standstill. Chesky made painful decisions — including layoffs — but navigated the crisis with transparency and empathy, rebuilding the company from its core mission outward.
In 2020, Airbnb went public in one of the decade’s most remarkable IPOs, a testament to resilience and reinvention.
A Designer CEO with a Human-Centered Vision
Through it all, Chesky remained anchored in his identity as a designer. He believes companies succeed not just through features, but through experiences that make people feel something. For him, design thinking isn’t a skill — it’s a philosophy.
Today, Brian Chesky continues to lead Airbnb into a new era of travel built around creativity, trust, and human connection. His journey proves that world-changing companies often start small — with a personal problem, a creative spark, and the persistence to push forward when everyone else says no.
Chesky’s journey is now studied in classrooms and boardrooms worldwide, not because it followed a perfect roadmap, but because it didn’t. His path shows that great founders aren’t defined by resources, luck, or early validation — they’re defined by creativity, resilience, and the willingness to redesign the world around them. And for Brian Chesky, what began with three air mattresses became a global symbol of what’s possible when you believe deeply in an idea before anyone else does.
