Every successful founder has a story that cracks people up. But most people keep their good parts to themselves. They enumerate the billion-dollar valuation, the magazine covers, the TED talks. What they omit is what comes before all that. The part where nothing worked. The part of the person who was heartbroken and broke, rejected and questioning everything they’d ever done.
Brian Chesky’s story is one of those stories. Today Airbnb is one of the most recognisable companies in the world. It spans more than 220 countries. From there, they read millions of articles every single month. The billionaire Brian is worth billions of dollars. But before any of this came to pass, Brian Chesky was a man so broke that he couldn’t pay rent, so inept at attracting investors that they didn’t believe in him and struggling to persuade people of his idea wasn’t absurd.
You are not the success story. Here’s the section that preceded it.
Who Is Brian Chesky? The Man Before the Money
Brian Chesky was born Aug. 29, 1981, in Niskayuna, a small town in upstate New York. He didn’t come from a lofty upbringing. His parents were social workers. They were not business people. They did not have ties to Silicon Valley. They had no money to invest in their son’s future startup. They were ordinary, hard-working folks who brought Brian up with a plain but sturdy set of principles, work hard, tell the truth and don’t give up.
Brian had creative and inquisitive tendencies from a young age. He was not the kid slumping in the back of the classroom doing nothing. He was the kid who wanted to create things. He was curious about the appearance of objects and their function. He drew a lot. He paid attention to design. These were not just hobbies. These interests would later develop into his entire worldview around business and products.
Brian attended the Rhode Island School of Design, or RISD. It’s one of the best design schools in the United States. Getting in is not easy. Brian did the work to get there and then worked even harder inside. He studied industrial design, the art and science of designing physical products. He learned to think about users and how to solve problems with his hands and creativity. He graduated in 2004. But the road ahead was not clear at all.
The Move to Los Angeles and Early Signs of Struggle
Brian moved to Los Angeles, after graduation. He became an industrial designer. On paper, this sounds great. He had a degree from a good school and worked in the field. But Brian was not happy. It didn’t feel as though the job was going anywhere. He wasn’t creating anything substantial and was not working on big problems. He was simply doing what was expected of him, and that wasn’t something he felt very good about himself for.
This restlessness is a feeling many have but few indulge in. Brian acted on it. In 2007, he had a big decision to make. He left his job and relocated to San Francisco. He saved a little bit of money, not enough to hang around for long, but some that would give him a little time to plan what his next move was going to be.
If you wanted to start a company, San Francisco was the place to be. When Brian came to San Francisco, he had little money. He hardly had enough to put toward the rent on the apartment he was sharing with his friend Joe Gebbia, also a RISD graduate. Things were genuinely tight. It was not a hyperbolic overstatement. They were on the verge of paying their basic bills.
The Cereal Box Idea, A Depression Disguised as a New Idea
Here is where the story gets a bit creative and a bit painful to read.
Brian and Joe needed money. Not startup money but just normal money to pay the rent. They had this idea to rent air mattresses, in their apartment, out to people who were coming to a design conference in San Francisco. The city’s hotels were also packed for the event. So, they thought they could charge people to sleep on air mattresses on the floor and feed them breakfast in the morning.
They called it “Air Bed and Breakfast.”
They made a simple website for it and had three paying guests stay with them. Brian and Joe each made about a thousand dollars. It was not a business for them till now, it was an ingenious answer to a private cash crunch. But it planted a small seed.
But, of course, this idea did not fly from there. People like to tell it in a way where this little experiment suddenly became Airbnb. That is not what happened. What ensued was a lengthy, grueling and humiliating run of defeat.
Brian and Joe designed another plan to raise money during that time. They designed custom cereal boxes tied to the 2008 presidential election. They produced Obama O’s and Cap’n McCain’s. They were selling these cereal boxes for forty dollars a pop. The boxes were humorous and inventive, and customers actually purchased them. They got something like thirty thousand dollars out of cereal. Because, breakfast cereal is thirty grand. That was the level at which they were working. Clever, yes. Sustainable, absolutely not.
Investors Said No. Over and Over Again.
With their cereal money and their air mattress idea, Brian and his co-founders, Joe Gebbia, who helped him come up with the name on that 2007 drive into San Francisco, and Nathan Blecharczyk, the technical co-founder who joined shortly after, began to attempt to raise real money for what would become Airbnb. What happened next was a master class in rejection.
They submitted an application to Y Combinator, perhaps the most renowned startup accelerator in Silicon Valley. In the initial submission, they were turned down. They tried again and eventually got in, but the rejection stung. A tiny fraction of applicants get accepted into Y Combinator. Getting turned away means that someone looked at your idea and decided, “No, we do not think this is worth our time or money.”
Then came the investor meetings.. Brian and his co-founders contacted seven angel investors. These are affluent individuals who fund early-stage ventures. Five of those investors failed to respond at all. Not a polite rejection. Just silence. Complete silence. The other two answered no. So seven attempts. Zero money raised. Five people who thought the idea didn’t even deserve a response.
Brian has discussed keeping a document, called the rejection deck. It contains a log of emails and replies from rejected investors. One investor said it was such a small market. One pointed out that people would never allow strangers into their houses. Others said the concept was simply strange. The overall sentiment among investors was that Airbnb was a solution in search of a problem.
These are not small rejections. These are people with backgrounds in business and investing saying to you, plainly and bluntly: Your idea is bad. Most people would have stopped. Most people would have interpreted that as a signal to go away. Brian did not stop. But it was difficult to keep going.
The Debt, the Doubt and the Dark Period
Meanwhile, Brian was racking up serious personal debt. He and his co-founders funded the business with credit cards. Not one credit card. Multiple credit cards. They were maxing them out and the debts were piling up as the company barely budged.
Brian has described how this period felt. He was auditioning in the past for a future interview. He was actually in trouble.. He also struggled with profound personal uncertainty. Doubt lingers at night, even when you’re resolute. You question whether those who reject you are correct.
There have been points in time when Brian has wondered about going back to a conventional job. He had a real skill set and industrial design is a true career. He could have returned to that world and had a comfortable, stable life. But somehow he felt compelled to keep going. He had not fully come to terms with it himself at the time.
The Company Was Not Growing, and That Was Its Own Kind of Failure
Even after they got into Y Combinator and found a few early users, Airbnb wasn’t growing like it needed to. The numbers were flat. People were signing up but weren’t actually using the platform in significant numbers. The listings were largely in New York, along with a handful of other cities. The product was rough. Not the best user experience.
Brian and his co-founders found that the sort of problem they had now was different. It was more than convincing to investors. It was about persuading everyday people to do something they had never done before. A stranger in your house, a stranger’s house on vacation, trusting that was not an inherent behaviour. It defied instincts that humans have for good reason.
They needed to go out and meet their users. They literally got on planes to New York and knocked on doors. They met with hosts. They photographed listings because the original photos were horrible. They would sit with people, ask them questions and listen. This was not glamorous work. It was slow and gruelling and extremely manual.
But it did teach them something essential. The product needed serious work and real growth would only come with truly knowing users at a deep level.
And the Lessons Of Failure He Burned Into Him Forever
Brian left those tough years with nothing to show for it. He left with something no business school could have taught. He learned that no is not a sentence. One person’s opinion at a single point in time. The investors who never replied were not the ones with foresight. They were only looking at the here and now, and the here and now was looking messy and uncertain. Brian learned to keep going no matter what.
He learned that real progress does not flow from dashboards and spreadsheets alone by sitting in New York apartments with hosts himself and taking photographs. It derives from a deep, personal understanding of people. That lesson informed how he built every segment of Airbnb afterwards.
The cereal box days helped him learn resourcefulness. When you have very little, you escape through clever means. Good survival instinct never abandoned him. Even as Airbnb grew into a billion-dollar company, Brian maintained that scrappy spirit. He had never believed that money solved any problems. He always thought that thinking was the way to solve problems.
It was the debt and the self-doubt that gave him resilience in a way comfort never would have. He had felt real fear. And he had emerged on the other side still standing. It gave him a kind of quiet confidence that is both unpretentious and unsalable.
What Happened Next Is a Story in Itself
The struggles didn’t last forever. Things started to change, slowly and then all at once. The product improved. The right people began to notice. That same idea that had been ignored by investors began spreading first between cities and then across countries.
But the full story of how Airbnb rose from near failure into a global empire deserves to be told on its own. It is a tale of daring decisions, unlikely rescues and a founder who never stopped acting as the designer he always was.
That story can be read here.
To know more about Brian Chesky and Airbnb, visit their website, Instagram, Facebook and X.
If you like more such business stories from around the world, keep on reading at Inspirepreneur Magazine.
