The Key Decisions That Made Brian Chesky Successful

Brian Chesky is the co-founder and CEO of Airbnb, the platform that fundamentally changed how millions of people travel and experience the world.

At 26 years old, broke and desperate, he took the absurd idea of renting out air mattresses in his San Francisco apartment and turned it into a company worth over 100 billion.

But Chesky's story isn't really about building a massive business. Instead, it's about a founder who consistently broke every rule in the playbook and somehow kept winning.

He's a designer, not an engineer or MBA. He hand-folded cereal boxes to survive. He personally knocked on doors taking photos of apartments when the company was on the brink. And when everything crashed during a global pandemic, he leads by example.

Understanding Brian Chesky means understanding how a founder thinks when everything is on the line, and what really separates the companies that scale while keeping their soul from the ones that lose it.

In October 2007, Brian Chesky needed $1,150 to make rent.

He and his co-founder Joe Gebbia noticed a design conference had sold out all the hotels in San Francisco, so they inflated three air mattresses in their loft and listed them on a hastily built website they called "AirBed Breakfast."

Three strangers booked: Kat from Boston, Michael from Utah (a 45-year-old Mormon father of five), and Amol from India.

Brian was terrified. But something unexpected happened over that weekend.

They had genuine connection. They became friends. They hung out. They went to the conference together. They belonged to each other, even for just a few days.

This moment taught Brian something that most founders take years to learn, if they ever learn it: the feeling is what matters.

It wasn't about cheap housing or a scalable business model. It was about belonging.

Later, that feeling would become Airbnb's entire north star.

When investors rejected him, when revenue flatlined, when everything looked impossible, Brian could always close his eyes and remember that weekend.

He didn't have proof of a business model. He had proof that people yearned for connection in a way hotels could never provide.

The takeaway for founders: Don't overlook the moments that feel right even if they don't look profitable yet. The thing you can't quite explain to investors is often the thing that actually matters.

By fall 2008, Airbnb was dying. Brian and Joe had racked up $20,000 in debt each. Nathan, the third co-founder, moved back to Boston and gave up.

They'd been rejected by 15 investors. Revenue was essentially nothing. Brian had nothing in his kitchen but ketchup. They needed money fast.

Brian and Joe watched the news and saw the 2008 presidential election consuming everything. They realized hotels were sold out during the Democratic National Convention.

So they did something insane. They hand-folded presidential-themed cereal boxes using a hot-glue gun in their apartment.

They sold them for $40 each, each box costing maybe $4 to make.

They approached journalists and bloggers, got coverage, and ended up selling enough to make $30,000 in profit.

The money kept them alive.

But here's what mattered more: Paul Graham at Y Combinator saw that cereal box and realized these guys wouldn't die. "If you can convince people to pay $40 for a $4 box of cereal," he said, "you can probably convince people to sleep in other people's airbeds."

Paul funded them not because the business model was proven, but because Brian showed he had survivor instinct.

The takeaway for founders: When conventional paths close, doing unglamorous, desperate, weird things that don’t scale often tells investors and customers more about you than a polished pitch ever could. It shows what you actually believe about your idea.

Brian was in Y Combinator now, but the numbers were still flatlined.

Thirty bookings total. No growth.

Paul Graham asked him a simple question that changed everything: "Where are your users?" Brian said, "New York." Paul replied, "Then what are you doing in California?" So Brian and Joe flew to New York.

And Paul gave him advice that sounds almost too obvious but that most founders ignore: Do things that don't scale.

Instead of trying to build perfect algorithms from 3,000 miles away, Brian and Joe showed up in person.

They noticed the listings had terrible photos: grainy, dark, uninviting. So they went door-to-door offering to take professional photos for free. They didn't delegate this. They grabbed a cheap DSLR camera and knocked on hosts' doors themselves.

While they were there, they watched how hosts interacted with the website. They saw what was confusing. They saw the friction. They got what Joe called "enlightened empathy" by actually being alongside your customer.

Within a week, revenue doubled. Then doubled again. Not because of some clever algorithm. But because two founders showed up in person and did manual work that didn't scale.

The takeaway for founders: The unscalable thing in the early days is often the right thing. You don't win by building what scales. You win by building what your customers actually love. Once you understand what they love by being there with them, then you scale.

By summer 2011, Airbnb was a real company. Millions of users. Huge growth.

Then a host in San Francisco named EJ came home from a business trip to find her apartment ransacked.

Someone had stolen her grandmother's jewelry, her passport, her laptop, her entire life. The police suspected a guest. EJ wrote a blog post called "Airbnb: A Nightmare." It went viral.

Brian had a choice. He could hide behind legal liability because Airbnb is just a platform, not responsible for what guests do. Or he could go the other way.

He chose to go the other way. He published a blog post apologizing, admitting they "dropped the ball," and announcing a $50,000 Airbnb Guarantee covering any host's property damage or theft caused by a guest. He even made it retroactive.

This could have cost millions. It almost did.

But Brian understood something about trust that most leaders miss: in a crisis, you don't do less. You do more.

Brian says: "A crisis is a stage. It's a spotlight. It's your moment to demonstrate your values." Most leaders see a crisis and think, "How do I protect the company?" Brian saw it and thought, "How do I show what we actually stand for?"

After the guarantee launched, bookings surged. Not because of PR. But because hosts knew Airbnb would do the right thing even when it was expensive.

The takeaway for founders: The expensive, generous move in a crisis often wins more trust than a thousand cautious moves. People don't forget when you had a chance to protect yourself and chose to protect them instead.

In March 2020, Airbnb's business dropped 80% in eight weeks. Bookings collapsed. Revenue evaporated. They were burning $250 million a month.

A board member told Brian, "This pandemic is 10 times a 9/11." It's your defining moment as a leader, he said.

Brian made a series of decisions that violated almost every rule of conventional startup leadership.

First, he fully refunded all guests canceling due to the pandemic, even though it meant hosts wouldn't get paid. Hosts were furious. Brian had to admit he didn't consult them. But he did what he thought was right.

Then he laid off 25% of the workforce, which amounted to 1,900 people. But instead of the typical cold layoff, Brian gave laid-off employees 14 weeks of base pay plus one week for every year at the company. He covered a year of health insurance. He created a public directory of their skills so other companies could hire them.

Then Brian did the most controversial thing: he took back control. He decided he would personally review every product before it shipped. He reorganized the company functionally instead of divisionally. Brian believed this was what the moment required. He was obsessed with getting back to the core experience that made Airbnb special.

He also did something almost nobody expected: he went public. In December 2020, 8 months after Airbnb looked like it might die, it had an IPO that was one of the biggest in history. The stock more than doubled on day one. Airbnb's market cap closed at over $100 billion, more than Marriott, Hilton, and Hyatt combined.

The takeaway for founders: Conventional wisdom doesn't always work in a crisis. Sometimes you need to get your hands dirty. Sometimes you need to make the expensive, generous move. Sometimes you need to get back to the core of what made your company special. That's what separates founders who survive crises from founders who come out stronger.

Brian wasn't trying to disrupt anything. He was just trying to pay rent. In October 2007, he and his co-founder Joe Gebbia were $1,150 short each month on their San Francisco apartment. They noticed a design conference in the city had sold out all the hotels, so they listed three air mattresses for $80 each. But what changed everything wasn't the money. It was the feeling. Three complete strangers showed up, and instead of it being awkward or transactional, Brian felt something genuine. That weekend taught him belonging matters more than convenience.

Brian faced over 15 rejections from investors before Y Combinator. Every investor said the same thing: strangers will never stay with strangers, so go get a real job. But Brian didn't see rejection as a sign the idea was bad. He saw it as a sign that nobody else understood what he understood from that first weekend. He held onto conviction when everyone told him he was wrong. That conviction was the only thing keeping him going when he had nothing but ketchup in the kitchen.

Paul Graham told Brian something simple but earth-shifting. Do things that don't scale. Instead of trying to build algorithms and optimize conversion rates from California, Brian flew to New York and knocked on hosts' doors to take professional photos of their apartments. He didn't delegate this work to anyone. He did it himself with a cheap camera. Within weeks, revenue doubled, then doubled again. This taught Brian that in the early days, great founders don't build from a distance. They get their hands dirty.

In fall 2008, Airbnb was completely out of money. Nathan, the technical co-founder, had given up. Brian and Joe were $40,000 in debt with essentially no revenue. But instead of panicking, they hand-folded presidential-themed cereal boxes called Obama Os and Cap’n McCain and sold them for $40 each. They made about $30,000 in profits, which kept them alive. But the real value wasn't the money. Paul Graham saw that cereal box at their Y Combinator interview and said if you can convince people to pay $40 for a $4 box of cereal, you can probably convince people to sleep in other people's airbeds. That gesture showed Paul Graham what mattered: Brian had survival instinct and would do whatever it took.

At the first weekend, his fear was that strangers would think he was crazy. At the cereal box moment, his fear was that the whole thing would collapse. In 2009, his fear was that he'd never figure out product-market fit. In 2011, his fear was that one host's nightmare would destroy trust forever. In 2020, his fear was that Airbnb would die, period. But each time, instead of letting fear paralyze him, Brian used it as information. Fear told him what mattered most, and he moved toward it.

When a host's apartment got ransacked and the story went viral, Brian had a choice. He could hide behind legal liability or take responsibility. And he chose responsibility. He launched a $50,000 Guarantee that could have bankrupted the company, made it retroactive, and apologized publicly. He didn't do this to manage the PR crisis. He did it because he knew that in that moment, Airbnb's future was being decided. He demonstrated what the company actually valued through money and action.

When Airbnb's business dropped 80% in eight weeks, Brian made unconventional moves. He fully refunded guests to protect them, even though it meant hosts took the hit initially. He laid off 25% of the workforce but gave them 14 weeks of severance, a year of health insurance, and created a public directory to help them find new jobs. Then he did something most CEOs would never do. He personally reviewed every single product before it shipped. He went back to controlling the details because he knew that's what the moment required.

Founder Mode is the opposite of what most leadership advice tells you. Instead of delegating and empowering teams, Brian believes great leadership requires presence. He stays obsessively connected to the customer experience. He lives in Airbnb listings. He reviews products. He gets into the details. The idea is that if you disconnect from what your company actually does, you lose the thing that made it special in the first place.

Brian sees crises differently than most leaders. Instead of thinking about how to minimize damage, he thinks about how to demonstrate what the company really stands for. The EJ crisis showed Airbnb values hosts. The pandemic showed Airbnb values employees. The cancellations showed Airbnb values guests. Each crisis was a chance to prove something people didn't have to believe before. Brian says it plainly: a crisis is a stage and a spotlight, and it's your moment to demonstrate your values.

That first weekend in October 2007 became Brian's north star. He felt something genuine with Kat, Michael, and Amol that he couldn't articulate at the time, but he never forgot it. When investors rejected him, when the cereal boxes barely sold, when the business flatlined for a year, when a host's apartment got ransacked, when the pandemic hit, Brian always came back to that core memory. That weekend taught him what Airbnb was really about. It wasn't about bookings or growth. It was about belonging. Holding onto that when everything else was falling apart is what separated Airbnb from a thousand other ideas that died during those early years.

Most founders obsess over scale from day one. They want everything to be automated, systematized, and leverage-able.

Brian does the opposite.

When Airbnb needed proof of concept, he did not build a booking algorithm. He inflated air mattresses and hosted strangers.

When the company was dying, he did not hire a cereal company. He hand-folded boxes with a hot-glue gun.

When listings looked bad, he did not commission a photo shoot. He knocked on 300 doors in New York himself with a cheap camera.

In 2020, he did not delegate product decisions. He personally reviewed every ship.

The pattern is clear across each critical moment. Brian identified the thing that mattered most and did it himself, even if it could never scale. He knew Paul Graham's lesson well: most startups perish because they try to scale before they have figured out what they are scaling.

The takeaway for founders: In the early days, having 100 people who love you beats having 10,000 people who think you are fine. The unscalable move becomes the one that actually builds that love. Do not hire someone to do it. Do not build an algorithm for it. Get your hands dirty and stay there until you understand what people actually want.

Most leaders in a crisis focus on downside protection. They lawyer up. They hide behind technicalities. They try to contain damage.

Brian operates in the opposite direction. He sees a crisis as a stage where he can show the world what the company actually stands for.

EJ's apartment got ransacked, and Brian could have said the company operates as a platform and carries no liability. Instead, he launched a $50,000 Guarantee that could have bankrupted them.

The pandemic hit, and Brian could have quietly cut corners and hoped to survive. Instead, he gave laid-off employees 14 weeks of severance and covered a year of health insurance.

In both cases, the expensive and generous move becomes what people remember. That moves is what builds trust.

Brian says this explicitly: a crisis functions as a stage and your moment to demonstrate your values. Not to manage PR. Not to minimize lawsuits. To show people what you actually believe in. When you take that approach, people believe you.

The takeaway for founders: Do not ask yourself what the minimum required action is. Ask instead what it would look like if you actually put your values first. That move, the one that costs more than expected and proves more generous than necessary, becomes the one that builds the kind of trust that survives everything.

The default path for most founders leads toward drift. As the company grows, you end up in meetings. You look at dashboards. You lose touch with what it actually feels like to use your product. You become a corporate CEO rather than a founder anymore.

Brian refused to let that happen to him.

In 2009, he went door-to-door meeting hosts. In 2011, he moved into Airbnb listings for almost a year, staying in host homes to understand what the guest experience actually felt like. In 2020, during the pandemic, he stayed in 18 different Airbnbs over six months.

He did not do this for PR purposes. He did it because he knows that if he loses touch with that core feeling from October 2007, that moment when Kat, Michael, and Amol felt like they belonged, then Airbnb becomes just another corporate platform.

This approach to leadership is what Brian calls Founder Mode. It functions not as micromanagement. It functions as presence. It means staying connected to the thing that made your company special in the first place.

He says explicitly: great leadership involves presence rather than absence.

The takeaway for founders: Whatever the core experience is that your customers come for, do not outsource it. Do not delegate it. Do not lose touch with it as you grow. Live in it. Use it yourself. Let it inform every decision you make. The moment you stop caring about that core thing more than anything else becomes the moment your company stops being special.

Brian Chesky's story matters because it's proof that conventional wisdom breaks at the moments that matter most.

A designer, not an engineer, founded a travel company. He didn't have a compelling pitch or a massive network or family money. He had desperation, creativity, and an unwillingness to quit.

He succeeded by doing things that seemed insane. To name just a few: hosting strangers, hand-folding cereal, knocking on doors, spending millions to protect trust, staying detailed even as a billion-dollar CEO.

Throughout his journey, Brian has kept one eye on that first weekend in October 2007, and he never let the company become something that would've betrayed what he learned then.

For any founder, entrepreneur, or investor watching this: the question isn't whether you'll face moments where conventional wisdom suggests one path and your gut suggests another. You will. The question is whether you'll have the conviction to trust the thing you learned when you had nothing to lose.