I think I was naturally a great founder and I was naturally a terrible CEO.
I want to start on December 10th, 2020. Airbnb goes public at an amazing value. I think by the end of the day, the company's worth over a hundred billion dollars, right? You are going to become extremely wealthy. This is an extraordinary moment, an amazing achievement. And you've described that as one of the loneliest moments of your life.
Well, first of all, the IPO was a weird experience because it was on Zoom because it was the pandemic and so there's no bell ringing. There was no like celebrating with your family, your friends, all the early people that helped you build a company. It was just a bunch of boxes on a Zoom and it felt really amazing. And I went to bed CEO of a hundred billion dollar public company never imagining I'd be CEO of a 10-person company and I woke up the next day and no one's in my house. It's still the pandemic, still sheltering in place and I wake up, put on sweatpants again, on a Zoom meeting. We just have like some random meeting and it was almost like I felt like my whole life had built up to wanting that moment, not necessarily an IPO, but being really successful. And then I think what happened was I had this crisis of realizing, okay, now that I've gone it, my life really isn't any different, and I don't feel that much happier than I did the day before. It was a rush. Like, and then the rush is over and I'm back to regular life. And it kind of created a little bit of an inner crisis because I think so much of my life starting with childhood was wanting to be special.
And I don't know if I even realized I was doing it. And maybe a lot of my ambition came from like wanting to get validation, wanting to be special, having this sense. I think a lot of people that are really successful, they want the world to love them. And I think, you know, maybe that's not love. Maybe it's adulation and it's kind of like a drug. You need more and more and more of it and it wears off very, very quickly and the inner crisis when you get to the mountaintop because you spent your whole life trying to climb the mountaintop and you realize this is not going to change how I feel inside. What do I do now? What other mountain is there even to climb?
And that began a whole another journey which was, well, what do I want out of my life? Why am I even doing this?
And to be honest, we didn't start this company to be successful. I joke that if I tried to make money I wouldn't have been inflating air mattresses. We didn't try to become successful. We started it, somewhere along the way it got so successful.
We started getting magazine covers.
And we started believing the hype and that was a little bit of an addiction.
I want to get back to that later on because I know that you made some conscious decisions about your life and how to live it. But to get to that moment, I want to go back many, many years. When I interviewed Joe on the show 10 years ago, telling us a story about Airbnb, he told us a story about how the night before you graduated from RISD, you went out for pizza and he said, and this is a quote, he said, 'We're going to start a company together someday.' That's what he said, he told us, he told you, and they're going to write a book about it. Do you remember that?
He said this to you in Rhode Island the night before you graduated.
Yeah. We were in Rhode Island because we went to Rhode Island School of Design. There was a, like in Providence, there's like, you know, it's very much a college town and like a lot of college towns there's like a main street with all the bars, restaurants called Thayer Street and on Thayer Street there was a restaurant, I think a pizza shop called Antonio's Pizza if I recall correctly. And it was really funny because they had like pineapple pizza and all these like exotic types of pizzas. I can't believe I remember this. And we're sitting by the window and he kind of says this out of nowhere and to me it was a little random, not that maybe we start a company together but the impression of they'll write a book about it because there were a few books written about it. But I think I want to give credit to Joe and my co-founders because I think he saw something in me maybe I didn't see in myself and one of the greatest gifts you can give to somebody is believe in them and see something in them. He saw something in me, don't know quite what it was. That's a thing for him to answer. And I feel like along the way, the only reason I'm here is because some people saw something and took a bet on me because the fact I went to Rhode Island School of Design as an artist.
I became CEO of a hundred billion dollar tech company. The metaphor was like as if Silicon Valley is a nightclub and the doorman was like looking away and I snuck in. It's like I wasn't supposed to be in this party.
I think your dad, I read that your dad said to you because you said I want to be an artist, he was like, 'Just make sure you get health insurance, please.'
Yes. And my high school yearbook quote, it's a very weird yearbook quote. My yearbook quote was, 'I'm sure I'll amount to nothing.' It was half a joke.
Because I thought all the yearbook quotes are kind of ridiculous. People were like taking themselves too seriously. But there had to have been a little bit of truth to that, that like I was going to be an artist and that was probably not a path to a lot of money and success. Like I like to joke that I went to like one of the only schools in America where it was uncool to make money, you know, because the cool kids at RISD were artists, not commercial, and you didn't do it for money. It was like pure. And so I had to go through this weird journey of even getting around the idea of making money. You know, originally I was actually of the three of us the one most opposed to having a business model and wanting to make money. I liked the purity of it being, you know, not a business model. And then I think I had a conversation with Joe and Nate. We kind of realized it was completely impractical for this company not to have a business model. And so then I worked with the team. We designed this business model that turned out to be one of the greatest business models of the internet. And it turns out I'm now an avowed supporter of capitalism because I've realized having given money to nonprofits that there is something unique about the innovation model of a corporate company that you can't do as a nonprofit.
Yeah. You eventually you go to LA for a couple years and but Joe manages to convince you to come to San Francisco where he's living with Nate as his roommate and eventually he wants to fulfill this. He really, I mean he says to you we're going to start a business. So he sees something in you which you don't see in yourself. Did you see yourself as a leader? Because early on, I mean Nate, Joe, you start this company, you're the CEO. I mean this is a decision that the three of you make. Did you see yourself in that role or did they see you doing that?
I saw myself as a leader of like five people, you know, maybe 10 people. I remember saying everybody's going to be huge one day. Thousands of people do this. So I believed in myself at a very small scale. It might have been the scale that Joe and Nate believed in me that was hard for me to see in myself.
We told the story of how you guys, you know, sold these cereal boxes at the Democratic convention and how that really sort of helped get you into Y Combinator and it's an amazing story and people could hear that on the earlier story we told with Joe. But I want to jump ahead a little bit. I mean, you were now almost 20 years since you started, right? And I think about, you know, I've been doing this for 30 years. If I think about where I was 30 years ago, I sucked at what I do. And so part of it is you just do it and you're going to suck less over time. And when you think about the first, let's say, five years, right here you are, you're a designer. Joe's a designer. Nate is a tech guy, but you're two designers in a tech city.
Trying to convince people that you know what you're doing. And you're trying to learn how to hire people, how to tell them what to do. And what do you remember about just learning those things and how it kind of evolved in those first few years?
Here's what I would say, Guy. I think I was pretty much naturally a great founder and I was naturally a terrible CEO.
Which is a very classic story.
I don't know an exception. I'm sure there are exceptions, but I don't know a person, especially a founder, that just becoming a CEO is completely intuitive. See, there's something about being a founder that's intuitive. It's possible people are born good founders. It's also possible we're not born good founders, but we spent our whole life being founders. Maybe that's the real answer is that like when you're a child, you're making things, you're building things, you're practicing being a founder. And so the moment you found a company, it's probably not the first time you try to make something. So I probably had 20 years experience as a founder starting as a child designing, disassembling Christmas toys, convincing my friends to like when I used to sell things to my friends. Joe and I had 20 years experience as founders. So by the time we were founders, we had decades under our belt and then suddenly you got to be this CEO. And the problem with being a CEO is it's so counterintuitive. Like for example, people tell you to hire great people and trust them and get out of their way to do their job. That is what you do once you're very mature. That is a death sentence to a young company. What you actually need to do is not hire big grown-ups that don't understand your stage.
That's counterintuitive. You have to hire people just a little bit ahead of you that are smart, hungry, and you got to stay really close to them. You got to stay really close to the company. So, said differently, so much of the CEO job is counterintuitive. And how do you create a culture where people do what you want them to do when you're not in the room? Like, that's the hard stuff.
Not, you know, becoming profitable. Yeah. Expense management. This stuff is easy.
I interviewed a CEO many years ago, really excellent CEO, and he said the job of CEO is not to have the answers, but to identify the people who do have the answers. And as you grew, I mean, you alluded to this, you were given the advice to start hiring people with more experience.
Much probably much older than you, right? And so, first of all, before we kind of dig into some of those experiences, because I know what eventually happened, right? What was that like for you to have, I mean, was it intimidating, you know?
To have people who are coming in, they're like, 'Brian, I got it here, you know, like I have 20 years of experience in the hospitality industry and this is actually how it's done.' And you probably deferred, right?
Yeah. I mean many of them are old enough to be my parents or almost old enough to be my parents. Like some of them were more than 20 years older than me. They had way more experience. And the hard part for me was sometimes my intuition would tell me one thing and they'd tell me another. And what do I do when my intuition and their experience collide? Usually I deferred and that was usually a mistake. It doesn't mean I was right, but it might have been that the solution was some engagement. My intuition is telling me this thing. It doesn't mean you're wrong, but now let's talk about it. Let's work through it together. And by not working through it, I knew the company so well that it's just really hard for somebody with experience at someone else's company to know what to do at your company. One of the reasons why is they usually come from big companies and they have trouble applying their big scale to a small company. They also come from companies where they didn't build it, they managed it and now they have to build it and they have never done that.
But you didn't know that at the time.
I didn't know any of that.
So, they were making decisions and probably some of the decisions were good, but your instinct was to defer because you didn't want to seem like you were arrogant, like you were a know-it-all.
I was a little intimidated and yeah, I felt cautious about being a boss. I felt a little shy about wanting to tell people what to do. You know what it was? I think I was a little bit of a people pleaser. I wanted people to like me. I think that's normal, by the way.
I want people to like me, especially people that seem older and more experienced. I don't want to tell them what to do. I want them to like me. And so I would be a little bit overly deferential,
100% conflict averse, averse to the point that if somebody wasn't working out, I would not take action. Take action doesn't necessarily mean firing them. Take action might mean having a really hard conversation about how things aren't going really well.
And if they aren't fixable, yes, then you have to make a change.
And somebody years later told me, a pitcher never takes themselves off of the mound, right? And as a coach, I kept hoping the pitchers would take themselves off the mound. Like, you give up five home runs. It's now obvious. No one ever comes to you and says, 'My arm's tired.' Most people think they're doing a good job. Whether you think they're doing a good job or not, they think they're doing a good job and they're doing the very best. And you are responsible if they're not doing a good job because you're the one that convinced them to do the job in the first place. And I would just avoid people that weren't being successful because I was conflict averse and I'd gravitate to people that were being successful. The other mistake I would make is I'd sometimes do their job for them, not realizing well the fact that I'm doing their job for them means maybe they can't do the job and I'm not empowering them or maybe this is a crutch and now they're successful because I am helping them. But that is actually ultimately perpetuating something that's unsustainable. And the other thing you do is you don't say no enough. Like if five execs want to go in five different directions, it's one team.
Right. So like if five of us get in a car and one says let's go to Tahoe, the other says let's go to like Reno, the other says let's go to LA. The right way is one way and one way has to be your way.
So you have to have one way. And if you hire people and they take you in the direction you don't believe in or it's the wrong direction, they'll eventually leave having built their own people that follow them down that direction. Now you've got to basically fix that thing. And so you might have hired someone, they've gone down a path for two years. Guess what happens? They leave. You might spend five or 10 years fixing or correcting that decision that person made. So I like to tell people they're not your people. Because when you leave, they're our people. And that direction is our direction, not your direction because I have to live with it long after you do.
You know, during that time, and you go, you like lay in bed and you're done with the day, did you ever think maybe I'm not the right person to do this?
All the time. I lived in this almost prison where I felt like I don't know if I'm ever going to have the capacity to be a great CEO, but I also saw failure after failure of what happened to a company and the founder left.
But what would you tell yourself?
I was like, I don't know how to get out of this. And I said to myself, I think I need to run this company long term. I don't know if I'm ever going to be a great CEO. I think the limit of the company's potential is the limit of me. A company can't grow faster than a CEO's learning curve. And so I just said like, how did these greats before me do it? I must not have this ability, but I'm going to just do my very best because I don't know what to do. I looked for like presidents and COOs. I hired those types of people. That wasn't really successful. I never got to the point where I told the board like, 'You need to find someone to replace me.' And the company to be clear wasn't like doing nose-diving. It was still growing.
But it was clearly not like in the mid-2010s or the late 2010s, there was this period where we're growing, but it's really clear the company's chaos. And I just didn't know how to manage the chaos. I didn't know how to manage excellence, how to align everyone and get them all to go in one direction. And it just felt like sand falling through your fingers. And all the things told me about big companies was becoming us. You know, there's like meetings about meetings and then like people are going in many different directions. And what ends up happening, and this is happening with a lot of AI companies now, is they just have too many people doing too many things and there's too many yeses, not enough nos. And the job of a CEO is to say no probably more than to say yes. And to make sure that we're a captain on one ship. We're not presiding over an armada of ships going in different directions because we have no leverage.
Yeah. I mean it would take you years to discover that and that is what age and wisdom bring. I mean when you're sitting there saying I don't know if I'm the right person, you're also withstanding a lot of pressure that is coming from you and maybe just, I don't know, the general sense that you had around you. The company's growing but you know as you describe it there's still chaos. What was the thing that kept you saying to yourself, 'No, I'm going to stay doing this.' Right? Because it really is, I mean there are mentioned examples of founders who are still CEOs. Jensen Huang is another great example. But there are so many examples who are not operationally involved. You are still here almost 20 years later. So what was it or who was it? Was there a person, was there a mentor who said you should stay, you should keep doing this, you're going to get better at this?
That's such a good question.
What do you remember? Because I would have left. I would have said, you know what? I want to just do a design job. Not just I want to do something, I want to be a brand ambassador. Let me bring somebody else to deal with all the...
A couple things come to mind. The first is my dad. My dad taught me growing up never to quit. He said, 'I don't care how talented you are.' I'm not very tall. I'm pretty short. I'm 5'8. So I played ice hockey and I hit puberty late. And I went to this military sports academy for hockey. And my dad and I both knew I wasn't the biggest. I wasn't the most talented. In fact, my favorite movie as a kid was Rudy. Some people might be too young to know what that was. It was this young little guy that was like 5'7, a walk-on at Notre Dame. And that was my hero. I was the underdog. My dad said, 'It's not the size of the dog in the fight, it's the size of the fight in the dog that matters.' He used to say that to me all the time. 100% or nothing. Never quit. Never quit. Never quit. So, first of all, that's ingrained in me. I don't even know how to quit. That seems like defeat. Now, if the board or the world told me, 'Please stop,' I would have. If Joe and Nate said, 'Brian, I need to take you off the mountain,' I would have gone off the mountain. But they never did. In fact, they told me even in my darkest hours, 'I believe in you.' Including during the pandemic. My darkest actual professional moment was when the pandemic hit. I remember Ken Chenault, CEO of Amex, was on our board. He was CEO of Amex during 9/11, 2008. He said, 'Brian, sometime in your career, you're going to have to deal with a 9/11 or 2008.' It was literally March 15th, the Ides of March.
Ken calls me. He said, 'Remember 9/11? This is going to be 10 times the size of 9/11 for travel as far as impact.' We lost 80% of our business in 12 weeks.
Right. I remember we interviewed you at that time. You said we spent 12 years building this business and we have lost 80% of it in a matter of weeks.
Eight weeks. And people were asking, is this the end of Airbnb? Is it going to exist? And it was that moment that the board rallied behind me and my co-founders rallied behind me. I think it was the people who believed in me that told me to keep going. It was me feeling like I can't quit. And it was me just believing that we're just starting, that this is a book and they had written a book about us and it was like 14 chapters. I'm like, really, you've only written the first chapter. That 14-chapter book is really just chapter one because we have so much longer to go. One other thing though that really got me down, and I didn't mention this in the first question you asked about the IPO, the thing that really I think got me down was how lonely I was. The job of a CEO can be so lonely. See, being a founder, if you have co-founders, is not lonely. In fact, when you're a co-founder, you have your friends, you're in it together. No one's really in charge. You hire your friends. They are young in your 20s. You go out drinking together. You hang out together. It feels kind of like a college crew.
And then you become CEO. You're not supposed to socialize with your employees as much. Your employees have family, so they're not going to hang out with you. Everyone's looking at you in every direction and you feel like the walls are caving in and you feel like everyone's just staring at you, evaluating you. It's like imagine you're a high school student and all of a sudden someone told you to be the principal of your own high school and you're like, 'Wait a second.' And everyone in school's talking about you and every time you walk into a room, everyone's preparing for you to enter that room and it's all like a production, a performance. It's very, very hard to wrap your head around that. And I didn't realize at the time that so much of the emptiness that I felt was just loneliness and that I had to reconnect with myself, my purpose. Like why am I even doing this? I'm not doing this to become a hundred billion dollar company because I realized that I wasn't any happier as a hundred billion dollar company than a $20 billion company. It's just an idea. It's like a drug. It's a rush and it wears off. And so then you got to go back to like what do I want in my life? And I said, 'Well, first I need to have more friends. I need to reconnect with my friends.' In fact, it was President Obama who became a mentor to me.
You wrote him a letter right in the middle of this. You reached out to him and asked for help.
Yeah.
I just like I wrote this long letter for help. And he basically told me, 'Brian, I think it's pretty simple. You're really lonely.' And he said, I remember him saying like, 'I have at least 15 friends that I could call at any moment and I don't need to catch them up to where I'm going in my life.' And many of them are his high school friends. In fact, I asked him, I said, 'How did you become basically like the most famous person alive and not lose your mind?' Because a lot of celebrities lose their mind. A lot of rich people lose their mind and get really powerful. And one of the things he told me, and I'll never forget this, is he said, 'The way I didn't lose my mind is I stayed grounded.' And the way you stay grounded, you stay connected to your roots. And the way you stay connected to your roots is you stay connected with people in your roots. And he had these like high school friends. He had this guy named Bobby. He's a fisherman. They've been friends since high school. And I had a friend named Bob, but I didn't talk to my friend Bob for like a decade. And so I kind of realized I thought I had all these friends, but then I realized if I called any of them, I'd have to get them up to speed in my life. And I'm like, 'Okay, those are dormant relationships because I put my whole life on hold.' I realized that I wasn't very vulnerable around my employees. I was closed off. I wanted to look strong. I didn't want to admit that I was vulnerable. I didn't want to admit I don't have the answer. I didn't want to admit I'm struggling. I didn't want to admit like, hey, I don't know if I'm really good at this. I need your help. And so, I wouldn't let people in. And so, a lot of this was loneliness. And a lot of loneliness was just a lack of vulnerability, not wanting to let people in, and just allowing walls to keep on you. Just becoming too busy for things that seem unimportant, like relationships, which are the most important.
Well, that's the thing. I mean, here you are. And I remember we spoke at that time and you said, 'I'm staring at a green dot all day.' I remember you saying that. I mean, you started so young, right? And you're grinding for so long. This is it. This is your life. And you get to a point where you're well known, you have money, but you have focused on this and so your personal life takes a back seat.
It becomes much more complicated, right, and complex to try to build one when you are known and all of these things.
I would walk down the street and I wasn't famous, but I would hear people say, 'That's the Airbnb guy.'
And it was weird because like it wasn't 'That's Brian Chesky,' it was 'That's the Airbnb guy.' And the weird part about that is at one point me and Airbnb started like blurring together. Like I'm literally people call me the Airbnb guy. And so I started losing... and if all you do is Airbnb, you're the Airbnb guy and there's nothing else, then maybe you are just the Airbnb guy. There's nothing else of value. At one point I had nothing to talk about but Airbnb because I didn't do anything. I didn't read anything. I didn't know anything about Airbnb. I was probably an uninteresting person to talk to unless you wanted to learn about Airbnb. And paradoxically that made me a worse leader because it was almost like I was just staring at the painting for too long. And if you just get too in your head and you stare at things, you can start to like just kind of like an artist has to step away from the canvas.
And if you stare at something too long, you kind of start getting stuck and iterative.
And I think that was a really big thing for me to realize I can dedicate my life to something, but that doesn't make me that, and that this company is separate from me. There has to be some separation of identity.
The first thing I did is I called up a bunch of, in the middle of the pandemic, my high school and college friends and I just started doing Zooms with them. Then I said we should do an annual trip because the first thing we do Zooms but we'd have had no new experiences. So all we're doing is talking about 15 years ago.
So we started traveling together. We started doing trips together. And that completely changed my life. A lot of people think, oh, I'm in a relationship, I'm in a happy marriage and not lonely. Well, actually loneliness I learned because we hired the Surgeon General of the United States to help during COVID and he actually studied loneliness. He said, 'Brian, the way to think about loneliness is concentric circles. First, you have to have a relationship yourself, solitude. Then family, maybe call it five people. Then the next concentric circle is 15 people you can confide in, 10 to 15. Then it's 150. You might call this your workplace, your community. And then there's the cosmos, your country, your community, something much bigger than anything you can ever fathom. If you have any disconnection to any of those rings, there is an element of disconnection that makes you lonely.' And I think so much of the unhappiness today in the world is people feeling disconnected to one of those rings. And I was disconnected to almost all those rings. If I really ask myself, I was just connected to this Airbnb, mostly this idea at this point. I was even disconnected to people I'm working with. And the pandemic made it worse because I lived in my house for two years. I worked 100 hours a week. It was the best thing for Airbnb for the short term. But by the end of it, man, I was in a pretty rough, tenuous place.
But how do you know? I mean, how do you know who to trust, right? Especially when people know the value of the company, what that means for you. You're well known. You know, I met my wife when I was 24. I'm 52, right? So, how do you know who to trust when your entire adult life up until that point is so focused on work? Understandably, you're building something and then you have to consciously decide to focus on the things that you neglected.
But you've got to now, but you're now known and there are consequences in trusting people who violate that trust.
I did something that might be unpopular or counterintuitive, which is I just decided to give everyone the benefit of the doubt, trust them, and let people tell me who they really were. And if they violated my trust, then they wouldn't be in my life, but I would assume good intent. Said differently, there are some people I met in Silicon Valley, they said, 'No new friends.'
