Brian Chesky

Garry Tan says Y Combinator vets a founder in a 10-minute interview that ends in an up-or-down decision. The firm now gets 80, maybe 90,000 applications a year for about 800 spots, an acceptance rate under 1 percent. Maybe 8 to 10 percent of applicants get an interview, sometimes less. Paul Graham figured out that a half hour or an hour was unnecessary. Five minutes would probably do, and five minutes feels rude, so the interview stayed at 10 minutes.

The limit works like the old 140-character cap on Twitter. In the window, Tan wants a real person, a problem, and a plain account of how the technology solves it, plus why the idea is worth building. If a little time is left, he wants to know

Brian Chesky says Airbnb.org is going to try to provide a million nights of free housing a year, for five years, for people in crisis. The nonprofit's leader put the biggest operable scale at a million nights in a few years, which Chesky thinks would pass Ronald McDonald House and any government. The cost he was given was about half a billion dollars of the company's money. He says a public company had to be able to do that responsibly for shareholders, that doing good is good business, and that this may be one of the most important things Airbnb does.

The idea is older than the company. In 2008 he emailed his co-founders with the subject line Airbnb.org, before Airbnb had launched, already

Brian Chesky says the pandemic was the first moment he had to be a good chief executive, because it was life or death. Before that, being better at the job was a nice-to-have that might have made Airbnb grow faster and feel less chaotic. In the crisis, either he was a good chief executive and the company survived, or he was a bad one and the company died. Guy Raz, earlier in the episode, quotes him from 2020 saying Airbnb lost 80% of the business, and Chesky puts that drop at eight weeks. He was about 38 or 39, about 12 or 13 years in, and he says he is good in a crisis.

Hands-on work, which he calls founder mode, came only from that crisis. He had not thought about Steve Jobs for eight or

Brian Chesky says the chief executive job can be lonely in a way founding was not. With co-founders he had friends, nobody was really in charge, and it felt like a college crew. As chief executive he was less able to socialize with employees, the walls felt like they were caving in, and a lot of the emptiness after the IPO was loneliness. He was not happier running a $100 billion company than a $20 billion company. The rush wore off, and he decided he needed more friends.

He wrote Barack Obama a long letter asking for help. Obama told him the problem was simple: he was really lonely. Obama said he had at least 15 friends he could call without catching them up, many from high school, includi

Brian Chesky says hiring great people, trusting them, and getting out of their way is what a mature company does, and it is a death sentence for a young company. A young company should not hire big grownups who do not understand its stage. It should hire people just a little ahead who are smart and hungry, and the founder has to stay close to them and close to the work.

The hard part of the job is a culture where people still do the desired work when the leader is out of the room. Becoming profitable and managing expenses are easy next to that.

He usually deferred when an executive's experience collided with his intuition, and he calls that a mistake. Many of those executives were old enou

Brian Chesky calls it a failure of leadership when a team spends six months on a project and he has to kill it. They should never have gone six months down a journey without him pulling the plug.

He wants to be at the beginning and the end of the process and to check in during the middle. Projects head the wrong way for one of two reasons: they start wrong and are not set up for success, or they sit off on an island without oversight. Setting a project up for success means a clear vision, the right people, one directly responsible individual, enough resources, total alignment, the right process, and a scope that is neither too big nor too small. After that he sets a rhythm. He can stay invo

Brian Chesky gets honest pushback at Airbnb by keeping people who can afford to tell him the truth, then by taking the opposite side of his own idea so the team has room to disagree.

Most of the people willing to tell him the truth have been with him more than 10 years, including his co-founders and a few who do not need the job and can risk getting fired. In London last week, he and the team landed on a new company tagline. He texted his CMO and two creative leads that the line was final and he did not care what anyone said. After sleeping on it, he saw he had sucked the oxygen out of the room. The next day he told them they had two weeks to find a better tagline and said he thought a bett

Brian Chesky talks to employees two or three layers below his direct reports so he hears from the people doing the work, not only from the executives above them.

Right after COVID, executives called the move undermining, going around them, and micromanaging. Feelings had to come second while the company was in crisis and had to be saved. Letting executives own the details had already run for 12 years, and the company was doing well probably in spite of his leadership, not because of it. The company had the curse of a business model that was too good. eBay had a great business model and did not have to be great at execution. Amazon had a horrible business model and low margins, lived by exec

Brian Chesky says fast success made Airbnb sloppy because the company forgot how hard the first product was to create. The team iterated 30 versions of the website before Airbnb worked, then expected everything else to work. Teams got funding, and employees were expected to invent the next great thing. Many good employees could not have started Airbnb, so asking them to start the next Airbnb was too much. Money, resources, and pressure to expand fed hubris, overconfidence, and indulgence. With no money, founders stay disciplined, say no, live inside constraints, and stay principled. The first time they ride a rocket ship, judgment can go down. They start thinking they can do everything, thin

Brian Chesky asks his assistant how nice people are to her, because success makes everyone nicer to him and he becomes a bad read of character. Some people were very obsequious with him and would not treat her well.

He kept letting new people in on purpose. Stopping new friends means stopping growth and stopping learning. He would ease in rather than hand over something like a bank account. The risk of a few people violating his trust was better than the risk of living alone the rest of his life. A few people did break his trust. It was not irreparable, and taking the risk was 100 percent worth it. His default was to trust and let the consequences land wherever they landed.

Refusing to dat

Brian Chesky says a company cannot grow faster than its chief executive's learning curve, and he believed the limit of Airbnb's potential was the limit of him. In the mid-2010s or the late 2010s Airbnb kept growing and was clearly chaos at the same time. He did not know how to manage the chaos, how to manage excellence, or how to align everyone in one direction. It felt like sand falling through his fingers.

He wondered all the time whether he was the right person for the job. He felt almost imprisoned and did not know if he would ever have the capacity to be a great chief executive. He had watched failure after failure when a founder left. He did not know how to get out, so he told himself

Brian Chesky says he was naturally a great founder and naturally a terrible chief executive. He calls that a classic story. He does not know a founder for whom becoming a chief executive felt completely intuitive, though he is sure exceptions exist.

Founding felt intuitive. He leaves open whether people are born good founders, then treats a lifetime of practice as the real answer. A child makes things, builds things, and practices being a founder, so founding a company is probably not the first attempt to make something. He puts his own practice at 20 years, starting as a child: designing, taking Christmas toys apart, and selling things to friends. By the time Airbnb was founded, he and co-

Brian Chesky says he felt lonely the day after Airbnb went public because the rush ended and his life felt no different than the day before. Guy Raz sets that day as December 10, 2020, when Airbnb finished worth over $100 billion. Chesky went to bed as chief executive of a public company, never having imagined he would lead even a 10-person company. He woke to an empty house, still sheltering in place, put on sweatpants, and sat through a random Zoom meeting. Regular life was back, and the gap set off an inner crisis.

The listing happened on Zoom during the pandemic, with no bell and no gathering of family, friends, or early people who helped build Airbnb, only boxes on a screen. From child

To go public, you write a securities document called In S One. It is a 300 page page turner that will not compete with American literature as Sunday night reading. They were going to file it late march, put it on the shelf, and have been dusting it off.

People got in a car and drove to a remote destination within about 200 miles, staying at Airbnb. That produced a major surge in bookings in non urban areas, small towns, and rural communities, with people staying longer.

They took 1/4 of a $1,000,000,000, under $50 million, and sent it to hosts. They did not loan it; they just sent it to hosts. The hosts would have needed even more, but it was the most they could do.

Air bed and breakfast made collectible breakfast cereal for the Democratic Republican National Conventions in 2008. Joe and he made Obama owes from Cheerios and Captain McCain's, and they were literally hot gluing the cereal boxes in the kitchen.

When he was a kid, his dad used to say things are never as good as they seem and as bad as they seem. If that is true, things were not as good as they seemed in January, and they are probably not as bad as they seem in July.

For the last five months, a weekly Q and A has been the point of connection. No matter what question people ask, he uses a Mac and stares into the little green light next to the camera every week, telling them everything he can.

They did 14 weeks severance plus a week for service. They felt this is a health crisis and people need health insurance, so they made sure everyone had at least one year of health insurance even after never getting laid off.