Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

Brian Chesky 0:00 I think I was naturally a great founder, and I was naturally a terrible CEO.

Guy Raz 0:04 [upbeat music]

Guy Raz 0:08 I wanna start on December 10th, 2020. Um, Airbnb goes public at a amazing value. I think by the end of the day, the company's worth over $100 billion, right? You are gonna 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.

Brian Chesky 0:29 The day after.

Guy Raz 0:30 Yeah. Why?

Brian Chesky 0:32 Well, first of all, the IPO was a weird experience 'cause it was on Zoom 'cause of the pandemic. And so there was 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 $100 billion public company, never imagining I'd be CEO of a 10-person company. And I woke up the next day, and no one's at my house. It's still the pandemic. You're still sheltering in place. And I wake up, put on sweatpants, again on a Zoom meeting. We just have, like, some meeting. We're in a meeting. And it was almost like m- I felt like my whole life had built up to wanting t- 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 gotten 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 kinda cri- created a little bit of a, a inner crisis because I think so much of my life, starting with childhood, was wanting to be special.

Guy Raz 1:47 Hmm.

Brian Chesky 1:47 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, wanting... You know, having this sense. I think a lot of people that are really successful, they want the world to love them. Um, and I think, you know, m- maybe, maybe, maybe that's not love. Maybe that's adulation, and it's kinda like a drug, and you need more and more and more of it, and it wears off very, very quickly. And the inner crisis is when you get to the mountaintop 'cause you spend your whole life trying to climb the mountaintop, and you realize, "This is not gonna change how I feel inside. What do I do now? There's n- what other mountain is there even to climb?"

Guy Raz 2:20 Yeah.

Brian Chesky 2:21 And that began a whole 'nother journey, which is, "Well, what do I want out of my life? Why am I even doing this?"

Guy Raz 2:28 Hmm.

Brian Chesky 2:29 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. It... We didn't try to become successful. We started... It was somewhere along the way, it got so successful.

Guy Raz 2:42 Yeah.

Brian Chesky 2:42 We started getting on magazine covers.

Guy Raz 2:44 Yeah.

Brian Chesky 2:44 And we started believing the hype, and it, that was a little bit of an addiction.

Guy Raz 2:49 I wanna get back to that later on 'cause I know that, that you made some conscious decisions about your life and how to live it. But to get to that moment, I wanna go back many, many years. Um, when I interviewed Joe on the show 10 years ago-

Brian Chesky 3:05 Yeah

Guy Raz 3:05 ... 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 gonna start a company together someday." That's what he, he said, he told us, he told you. "And they're gonna write a book about it." Do you remember that?

Brian Chesky 3:23 Yeah.

Guy Raz 3:24 He said this to you in Rhode Island-

Brian Chesky 3:26 Yeah

Guy Raz 3:26 ... the night before you graduated.

Brian Chesky 3:28 Yeah. Um, it... We were in Rhode Island 'cause we went to Rhode Island School of Design. Um, there was a, like... In Providence, there's, like, you know, it's very much a college town.

Guy Raz 3:35 Yeah.

Brian Chesky 3:36 And like a lot of college towns, there's, like, a main street with all the bars and restaurants called Thayer Street. And on Thayer Street, there was a restaurant, I think a pizza shop called Antonio's Pizza, if I re- recall correctly. And they... It was really funny 'cause they, they had, like, pineapple pizza and all these, like, exotic types of pizzas. It's... I, I can't believe I remember this. And we're sitting by the window, and he kinda says this out of nowhere. And to me it was, it was a little random. Not that maybe we'd start a company together, but the prescience of they'll write a book about it 'cause there were a few books written about it. But I think I wanna give credit to Joe because, um, 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-

Guy Raz 4:20 Yeah

Brian Chesky 4:20 ... to somebody is believe in them and see something in them. He saw something in me. I don't know quite what it was. That's a thing for him to answer. Um, 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 that I became s- I went to Rhode Island School of Design as an artist.

Guy Raz 4:38 Yeah.

Brian Chesky 4:39 I became CEO of a $100 billion tech company. The metaphor was like as if Silicon Valley's a nightclub and the doorman was, like, looking away and I snuck in. It's like I wasn't-

Guy Raz 4:48 Yeah

Brian Chesky 4:48 ... supposed to be in this party.

Guy Raz 4:49 I think your da- I, I read that your dad said to you, 'cause you said, "I wanna be an artist." He was like, "Just make sure you get health insurance, please."

Brian Chesky 4:54 Yes. In my high school-

Guy Raz 4:55 Yeah

Brian Chesky 4:55 ... yearbook quote, it's a very weird yearbook quote. My yearbook quote was, "I'm sure I'll amount to nothing."

Guy Raz 5:00 [laughs]

Brian Chesky 5:01 It, I... It was half a joke-

Guy Raz 5:02 Yeah

Brian Chesky 5:03 ... 'cause I thought all the yearbook quotes were kinda 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 gonna 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?

Guy Raz 5:18 Yeah.

Brian Chesky 5:18 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 we had a conversation, Joe and Nate. We kinda realized it was completely impractical for this company not to have a business model. And so then I worked with a team, and we designed this business model that turned out to be one of the greatest business models on the internet And it turns out I am, uh, now a, a, an avid 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.

Guy Raz 6:05 Yeah. You eventually, you go to LA for a couple years.

Brian Chesky 6:08 Yeah.

Guy Raz 6:08 And, but Joe manages to convince you to come to San Francisco-

Brian Chesky 6:10 Yeah

Guy Raz 6:10 ... where he's living-

Brian Chesky 6:11 Yeah

Guy Raz 6:11 ... with Nate as his roommate. And eventually he, he wants to fulfill this. He really s-

Brian Chesky 6:16 Yeah

Guy Raz 6:16 ... I mean, he says to you, "We're gonna start a business."

Brian Chesky 6:18 Yes.

Guy Raz 6:18 So he sees something in you-

Brian Chesky 6:20 Yeah, yeah

Guy Raz 6:20 ... which you don't see in yourself. Did you see yourself as a leader? 'Cause early on, I mean, Nate, Joe, you, 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, or, or did they see you doing that?

Brian Chesky 6:40 I saw myself as a leader of, like, five people. You know, maybe 10 people. I remember saying, "Airbnb's gonna be huge one day. Thousands of people will do this." So I saw, I saw, I believed in myself at a very small scale. It might even been the scale that, uh, Joe and Nate believed in me that I, that was hard for me to see in

Brian Chesky 6:58 myself.

Guy Raz 6:58 We told the story of how you guys, you know, sold these cereal boxes at the Democratic Convention, and how that really ins-

Brian Chesky 7:06 Yeah

Guy Raz 7:06 ... sort of helped get you into Y Combinator, and it's an, an amazing story, and people can hear that-

Brian Chesky 7:10 Yeah

Guy Raz 7:11 ... on our, on the earlier, uh, story we told with Joe. Um, but I wanna jump ahead a little bit. I mean, you, you are now almost 20 years since-

Brian Chesky 7:20 Yeah

Guy Raz 7:20 ... you started, right? And I think about, you know, I've been doing this for 30 years, and if I think about where I was 30 years ago, I sucked at what I-

Brian Chesky 7:28 Yeah

Guy Raz 7:28 ... at what I do. And so part of it is you just do it, and you're gonna suck less over time. And when you think about the, 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-

Brian Chesky 7:44 Yes

Guy Raz 7:44 ... trying to convince people that you know what you're-

Brian Chesky 7:46 Fish out of water

Guy Raz 7:47 ... doing, and you're trying to learn how to hire people, how to tell them what to do. And w- what do you, what do you remember about, about just learning those things and how it kind of evolved in those first few years?

Brian Chesky 8:08 Here's what I would say, Guy. Um, I think I was pretty much naturally a great founder, and I was naturally a terrible CEO. And I-

Guy Raz 8:16 Which is, which is a very classic story.

Brian Chesky 8:18 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 tried 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 were like, we had decades under our belt. And then suddenly you gotta 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 to, 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.

Guy Raz 9:28 Yeah.

Brian Chesky 9:29 Y- that's counterintuitive. You have to hire people just a little bit ahead of you that are smart, hungry, and you gotta stay really close to them. You gotta stay really close to the company. So said differently, so much of the CEO job is, is counterintuitive. And how do you, 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.

Guy Raz 9:51 That's really hard.

Brian Chesky 9:52 Not, you know, being, becoming profitable.

Guy Raz 9:56 Yeah.

Brian Chesky 9:56 Expense management. This stuff is, this stuff is easy.

Guy Raz 10:00 I, I interviewed, um, a CEO many years ago, a really excellent CEO, and he said in, he said, "The job of a CEO is not to have the answers, but to identify the people who do have the answers."

Brian Chesky 10:11 I like that.

Guy Raz 10:12 And, and as you grew, I mean, you, you alluded to this, you were given the advice to start hiring people with more experience.

Brian Chesky 10:19 Yes.

Guy Raz 10:19 Much-

Brian Chesky 10:20 Much more

Guy Raz 10:20 ... probably much older than you, right? And so first of all, before we kinda dig, dig into some of those experiences, 'cause I know we'll, what, what eventually happened, right? What was that like for you to have, I mean, was it intimidating, you know?

Brian Chesky 10:32 Yeah, yeah.

Guy Raz 10:33 To have people who, who were coming in, they were like, "Brian, I got it here. You know, like, I, I have 20 years of experience in the, in the hospitality industry, and this is actually how it's done." And, and you probably deferred, right?

Brian Chesky 10:44 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, that the solution was some engagement. My intuition's telling me this thing. That doesn't mean you're wrong, but now let's talk about it. Let's work through it together. And it, 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 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.

Guy Raz 11:44 Hmm.

Brian Chesky 11:45 And they have never done that.

Guy Raz 11:46 But you didn't know, know that at the time.

Brian Chesky 11:48 I didn't know any of that at the time.

Guy Raz 11:48 So they were making decisions, and probably some of the decisions were good.

Brian Chesky 11:51 Yes.

Guy Raz 11:51 But your instinct was to defer because-

Brian Chesky 11:54 Completely defer

Guy Raz 11:55 ... you didn't wanna seem like you were arrogant, like you were a know-it-all.

Brian Chesky 11:57 I was a little intimidated And yeah, I, I, I, I felt cautious about being a boss. I felt a little shy about, like, 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.

Guy Raz 12:14 Very normal.

Brian Chesky 12:15 I want-

Guy Raz 12:15 Yeah

Brian Chesky 12:15 ... people to like me, especially people that seem older and more experienced. I don't wanna tell them what to do. I want them to like me. And so I, um, would be a little bit, um, overly deferential.

Guy Raz 12:28 Conflict-averse, too?

Brian Chesky 12:29 100% conflict-averse. And conflict-averse to the point that if somebody wasn't working out, I would not take action. Take action doesn't necessarily mean fire them. Take action might mean having a really hard conversation about how things aren't going really well.

Guy Raz 12:42 Mm.

Brian Chesky 12:43 And if they aren't fixable, yes, then you have to make a change. And somebody years later told me, "A pitcher never takes themself off of the mound."

Guy Raz 12:51 Right. [laughs]

Brian Chesky 12:51 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 say, "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 their very best, and you are responsible if they're not doing a good job, 'cause you're the one that convinced them to do the job in the first place.

Guy Raz 13:12 Mm.

Brian Chesky 13:13 And I would just avoid people that weren't being successful, because I was conflict-averse, and I would 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 do the job and I'm not empowering them, or maybe this is a crutch.

Guy Raz 13:32 Mm.

Brian Chesky 13:32 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 wanna go in five different directions, it's one team.

Guy Raz 13:48 Yeah.

Brian Chesky 13:49 Right? So, like, if, if, 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.

Guy Raz 14:00 Yeah.

Brian Chesky 14:00 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 gotta 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.

Guy Raz 14:37 W- W- When you would go home at night, right, in the, you know, in that time, during that time, and you'd go... you'd, like, lay in bed and you're done with the, the day, did you ever think, "Maybe I'm not right- the right person to do this?"

Brian Chesky 14:51 Yeah, all the time.

Guy Raz 14:52 All the time.

Brian Chesky 14:53 All the time. I w- I lived in this almost prison where I felt like I don't know if I'm ever gonna have the capacity to be a great CEO, but I also saw failure after failure of what happened to a company when the founder left.

Guy Raz 15:10 But what would you tell yourself when-

Brian Chesky 15:12 I was like, "I don't know how to get out of this," and I, I said to myself, "I don't... I think I need to run this company long term. I don't know if I'm ever gonna 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? Um, I must not have this ability, but I'm gonna just do my very best, 'cause I don't, I, I don't know what to do." I don't n- you know, I looked for, like, presidents and COOs. I hired those types of people. Um, they didn't, you know, that didn't, 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." Um, and the company, to be clear, wasn't, like, like, n- nosediving. It was still growing.

Guy Raz 15:55 Yeah.

Brian Chesky 15:56 But it was clearly not, like, like, in the mid-2010s or the late 2010s, there was this period where we're growing, but it's really clear the company is 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 you told me about big companies was becoming us. You know, there's, like, meetings about meetings.

Guy Raz 16:24 Yeah.

Brian Chesky 16:24 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 noes, 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, 'cause we have no leverage.

Guy Raz 16:50 Yeah. I mean, it would take you years to discover that, and that is what, like, that's what age and wisdom, right-

Brian Chesky 16:56 Yeah

Guy Raz 16:56 ... bring. Who... 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 gonna stay doing this," right? 'Cause it's really, it is... I mean, there are, you've mentioned examples of founders who are still CEOs. Jen Hsiang 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, was there a mentor who said, "You, you should stay. You should keep doing this. You're going to get better at this"?

Brian Chesky 17:44 That's such a good question.

Guy Raz 17:47 What do you remember? 'Cause I would've left. I would've said, "You know what? I wanna just do a design job."

Brian Chesky 17:51 Yeah.

Guy Raz 17:52 Not just. "I wanna do something. I wanna be a brand ambassador. Let me bring somebody else to deal with all the bullshit."

Brian Chesky 17:58 A couple things come to mind. The first is, um, 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, I'm, I'm pretty short, 5'8". So I played ice hockey, and I hit puberty late, and I went to this mil- this military sports academy for hockey. And w- 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.

Guy Raz 18:25 [laughs]

Brian Chesky 18:26 Some people might be too young to know what that was. It was this young-

Guy Raz 18:28 Yeah

Brian Chesky 18:29 ... little guy that was, like, 5'7" that was a walk-on at Notre Dame, and that was my hero. I was the underdog. My dad said, "Just ma- It's not the size of the dog in the fight, it's the size of the fight in the dog that matters." That... 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 mound," I would have gone off the mound, but they never did. In fact, they told me, even in my darkest hours, "I believe in you," including during the pandemic. My darkest moment, my, my, um, beyond the IPO, 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 gonna have to deal with a 9/11 or 2008." It was literally March 15th, ides of March.

Guy Raz 19:25 Wow.

Brian Chesky 19:25 Ken calls me, said, "Remember 9/11? This is gonna be 10 times the size of 9/11 for travel as far as impact," and it was. We lost 80% of our business in weeks.

Guy Raz 19:33 12... Right. I remember. We interviewed you that time.

Brian Chesky 19:35 Yeah. It was-

Guy Raz 19:35 You said, "We spent 12 years building this business, and we have lost 80% of it in a matter of weeks."

Brian Chesky 19:41 Eight weeks. And I didn't... And people were asking, "Is this the end of Airbnb? Is Airbnb gonna 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.

Brian Chesky 20:13 One other thing, though, that really got me down, and I, I, I didn't mention this 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. You... 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 kinda like a, like a college, like, crew.

Guy Raz 20:45 Yeah.

Brian Chesky 20:46 And then you become CEO. You're not as exposed to, like, socialize your employees as much. Your employees have families, so they're not gonna hang out with you. You know, everyone's looking at you every direction, and you feel like the walls are caving in, and you feel like the whole... Everyone's just staring at you, evaluating you. It's like imagine, like, you're a high school student, and all of a sudden someone told you you'd be the principal of your own high school. And you're like, "Wait a second." And everyone in school is talking about you, and every time you walk into a room, everyone's, like, 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, like, reconnect with myself, my purpose, like why am I even doing this? I'm not doing this to become a $100 billion company because I realized that I wasn't any happier as a $100 billion company than a $20 billion company. Like, it, it, it's just, it's, it's an idea. It's like a, it's like a drug. It's a rush, and then it wears off. And so then you gotta go back to, like, what do I want out of 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.

Guy Raz 21:57 You wrote him a letter, right, in the middle of this.

Brian Chesky 21:59 I wrote him a letter.

Guy Raz 21:59 You, you, you reached out to him and, and asked-

Brian Chesky 22:02 For help.

Guy Raz 22:03 Yeah.

Brian Chesky 22:04 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." [laughs] And, um, he said, like, he said, uh, I remember him telling, like, "I have fift- I have at least 15 friends that I could call at any moment, and I don't need to catch them up to what I'm going in my life, and many of them are just 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?" 'Cause a lot of, like, 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, he said, "The way I didn't lose my mind is I stayed grounded, and the way you stay grounded is you stay connected to your roots, and the way you stay connected to your roots is you stay connected to people in your roots." And he had these, like, high school friends. He had this guy named Bobby. He's a fisherman. He's, like, 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 kinda 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 on my life. And I'm like, "Okay, those are dormant relationships," 'cause I'd put my whole life on hold. I realized that I wasn't very vulnerable around my employees.

Guy Raz 23:07 Hmm.

Brian Chesky 23:08 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 f- lack of vulnerability, not wanting to let people in, and just allowing walls to cave on, on you, just becoming too busy for things that seem unimportant, like relationships, which are the most important thing.

Guy Raz 23:35 Well, that, well, that's the thing. I mean, here you are, and, and, and I remember we, we spoke at that time, and you said, "I'm staring at a green dot all day."

Brian Chesky 23:41 Yeah.

Guy Raz 23:41 I remember you, you saying that. I mean, you started so young, right? And you're grinding for so long. You're just, it's, this is it. This is your life. And you get to a point where you're well-known. You have money, and but you have focused on this, and so your personal life takes a back seat.

Brian Chesky 24:05 I had no personal life.

Guy Raz 24:06 It becomes much more complicated, right, and complex to try to Build one when you are known and all of these things

Brian Chesky 24:14 I would walk down the street and I wasn't famous, but I would hear people say, "That's the Airbnb guy."

Guy Raz 24:20 Yeah.

Brian Chesky 24:20 And it was weird because like it wasn't, "That's Brian Chesky, 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, like literally people call me the Airbnb guy. And so I started losing a s- and, and, and if all you do is Airbnb, you're the Airbnb guy and there's nothing else, then, then, 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, 'cause I didn't do anything, I didn't read anything, I, I didn't know anything about Airbnb. I was probably an uninteresting person to talk to unless you wanted to [laughs] learn about Airbnb. And, and, and, 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 like too in your head and you stare at things, you can start to like just kinda, like an artist has to step away from the canvas.

Guy Raz 25:09 Mm.

Brian Chesky 25:10 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 separate, separation of identity.

Guy Raz 25:27 So, so what did you do?

Brian Chesky 25:30 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, um, I said we should do a annual trip because the first thing, uh, we'd do Zooms but we'd have had no new experiences so all we're doing is talking about shit 15 years ago.

Guy Raz 25:46 Yeah.

Brian Chesky 25:46 So we started traveling together, we started doing trips together, and that was like completely changed my life. A lot of people think, oh, I'm in a relationship, I'm in a happy marriage, I'm not lonely. Well, actually loneliness I learned, 'cause we hired the surgeon general of the United States, um, to help f- 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 with yourself."

Guy Raz 26:09 Mm-hmm.

Brian Chesky 26:09 "Solitude. Then family, maybe call that 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, you know, 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 of 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 'cause I didn't leave 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.

Guy Raz 27:02 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.

Brian Chesky 27:12 Yeah.

Guy Raz 27:13 You're well known. You know, you are... Like I met my, my wife when I was 24.

Brian Chesky 27:20 Mm.

Guy Raz 27:20 I'm 52, right? So how do you know who to trust when your, 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.

Brian Chesky 27:38 Yeah.

Guy Raz 27:39 But you've gotta now, but you're now known, and there are consequences in trusting people who violate that trust.

Brian Chesky 27:48 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."

Guy Raz 28:07 Mm-hmm.

Brian Chesky 28:07 'Cause, uh, on-

Guy Raz 28:08 Yeah

Brian Chesky 28:08 ... only people I can trust are my old friends. The problem is when you don't have new friends, and there are people it m- I bet you people watching, they're parents, when you get to a certain age you stop making new friends. But when you stop making new friends and you stop letting new people in your life, you stop growing, you stop learning. And so I decided I'm gonna take the risk. Now maybe I'm not gonna like, you know, send them my w- bank account information and, you know, like-

Guy Raz 28:31 No

Brian Chesky 28:31 ... like, you know, I'm gonna like ease into it, but I decided to take the conscious effort to say the risk of a few people violating my trust is better than the risk of living alone the rest of my life. And did a few people violate my trust? Yes. Was it irreparable? No. Was it worth taking the risk? 100%. And so that's what I did. I think what happens with a lot of people that become wealthy, for example, is the world gets small because they're like, "I don't know who to trust," and my only answer is you gotta give people a chance. Now, you know, one way to know how you can f- like there's some tactics you can use. The more successful you get, the mo- nicer everyone is to you.

Guy Raz 29:12 Yeah.

Brian Chesky 29:12 So you start to become a bad read of character 'cause everyone's really nice to you. So we have to pay attention, how nice are they to other people?

Guy Raz 29:18 Mm-hmm.

Brian Chesky 29:18 And so one of the things I used to do is I ask my assistant how nice people were to her. 'Cause there were people that were very obsequious and unctuous-

Guy Raz 29:26 Mm-hmm

Brian Chesky 29:26 ... to me and they were really, they wouldn't treat her well.

Guy Raz 29:30 But your default was to trust.

Brian Chesky 29:31 My default was to trust.

Guy Raz 29:32 Which makes sense. Yeah.

Brian Chesky 29:33 And-

Guy Raz 29:33 And just wherever the consequences land, they land.

Brian Chesky 29:36 They land.

Guy Raz 29:37 Yeah.

Brian Chesky 29:37 And, and, and, and I think you're gonna get hurt. It's like saying, "I'll never date 'cause I, I don't wanna be in a relationship 'cause I'll only date, 'cause if I date someone might break my heart." Well, what's worse, having your heart broken or to like dying alone?

Guy Raz 29:49 Right.

Brian Chesky 29:49 I don't know, you pick your poison.

Guy Raz 29:51 Yeah.

Brian Chesky 29:51 So same thing with fail. I don't wanna start a company 'cause it might fail. I don't wanna like hire this person 'cause it might not work out. I don't wanna exercise, I might get hurt. I might, I might injure myself. I don't wanna live my life 'cause I might die. It's like you're gonna die anyway, might as well live.

Guy Raz 30:07 I looked over the transcript from our interview in 2020 during COVID, and you said, um, at the time you said That Airbnb had become stretched and sprawling, those were your words, um, that we were trying to do too many things, and I think, I think that's the time where you started to understand all of the things that would follow, right?

Brian Chesky 30:26 Yes.

Guy Raz 30:26 As, as you kind of re- began to rethink how you wanted to organize your life, your role at this company. What, what do you think, you know, why do you think that w- that happened in the first place when you reflect on it? I mean, you obviously started to recognize some of these challenges. Do you think you were, again, was it, was it connected to trying to please investors, employees, not having enough confidence in how you, you know, your decision-making? Why had it gotten to that point?

Brian Chesky 30:57 Actually, it was a, I think, I actually think it's a very different thing that I also suffer from, which is hubris.

Guy Raz 31:04 Hmm.

Brian Chesky 31:05 I think that I see this a lot. You have a hit. So I had the good fortune of, like, y- Joe and I, and we romanticize how hard it was, but in the grand scheme of things, it took off within a year and a half. That's not that long, and it became a phenomenon, and before you knew it, hundreds of million people were doing it. It was almost as if it was too easy, and we thought, "Well, everything else must be this easy." That's hubris, saying, "I can do anything, therefore, I can do everything," and we miscalculated how hard it would d- be to both grow something and start something new at the same time.

Guy Raz 31:37 Yeah.

Brian Chesky 31:38 We didn't build the foundation in place. We didn't have the right leaders or structure or support, and we just quickly, without enough rigor or discipline, I think we forgot how hard it was to f- to create the first thing. Said differently, I think we iterated, like, 30 versions of our website before we figured out how to make Airbnb work, and then we just expected everything else to just work, and we, like, would fund teams and we'd fund employees, expecting them to come up with the next great thing, and we had many good employees, but not many of them could have started Airbnb, and so asking them to start the next Airbnb, it was just too much to ask people. So I think it was actually, at one point, a little bit of hubris, a little bit of overconfidence, and a little bit of indulgence. You know, it's like you have an abundance of money. You have abundance of resources. Yes, you get pressure to expand, but a lot of what we do as founders is we always have the ability to suffer from hubris.

Guy Raz 32:38 Mm-hmm.

Brian Chesky 32:38 We have a hit, and we go from, like, being... When you have no money, you're really disciplined. You say no.

Guy Raz 32:44 Yeah.

Brian Chesky 32:44 You have constraints. You live in reality, and you're really thoughtful in principle, and the first time you go on a rocket ship, your judgment starts to, your judgment can go down, and you start thinking you can do everything. You have sloppy thinking. Um, you get, you get sloppy, and you just start throwing money at things, and you see what sticks, and I don't wanna call any companies out today, but you can see this. When companies have fast success, they try to expand too quickly into other things, and they just don't stick. It's really low quality, and that happened to us, and that, I think, is the adolescence of a company. You go through what we call growing pains. You basically, the company outgrows you. You don't know how to manage. There's chaos. Everyone's got a new manager every few months. You're doing everything but nothing well. Um, the company is, like, getting diluted. Suddenly, like, you know, it becomes wayward. There's more bureaucracy set in. You know, things get calcified. You know, and there's this other thing that happens where the more dysfunctional the company gets, the more you think, "Well, I must be the problem, so I'll step away," when actually, the best leadership is presence, not absence, so now you've kinda made it worse by perpetuating even more things, and it just, it just go, it gets worse and worse and worse, and at some point, your castle becomes your prison, and you basically built this beautiful castle, and then you've locked yourself in the top of it, and you're like, "I don't know how to get out of it," and that, that, then you have to basically figure out, "Okay, I created this, this beautiful thing that's I'm now stuck inside of. How do I fix it?" And that can get really, really difficult, and that's the journey I had to do for, like, five, six years.

Guy Raz 34:20 When do you remember, I mean, was it during COVID or, or before when you s- when you started to really understand what it meant to be a good leader? I know you studied Steve Jobs. You've talked about him, and you really have studied him deeply, um, and you've had mentors, right? I mean, President Obama, right, Paul Graham, and other people. But when do you remember or what was it where you started to think, "Okay, I think that I got this"?

Brian Chesky 34:49 After the pandemic.

Guy Raz 34:50 After the pandemic, so we're talking 12 years in.

Brian Chesky 34:53 Yeah, 13. 13. Um-

Guy Raz 34:56 And what was it? What, what was the, was it just a, an accumulation of things, or was there m- wh- were there moments, or a moment, or something or a conversation where you thought, "Okay, this is gonna change everything"?

Brian Chesky 35:08 It was probably, like, three things. The first thing was maturity. I was, like, 38, 39. Um, like, literally, like, I think I grew up with, like, pretty bad AD- ADD, ADHD, and I wouldn't say I grew out of it, but, like, I became more mature somehow, and I started, like, being more predictable, not the most predictable, but less of a procrastinator, little more mature, a little more decisive, a little less impulsive, so that was the first thing, just some maturity, and I think related to that was just 12 years of experience.

Guy Raz 35:40 Mm-hmm.

Brian Chesky 35:40 Some point you figure it out, or you're never going to, and that's, like, a good amount of time. I think the second thing was it was a crucible moment. In other words, it was the first moment I had to be a good CEO, and it was a life or death moment. 'Cause before that, it was a nice to have to be CEO. Well, we could grow faster, be less chaotic, but at that moment, either I'm a great CEO and the company survives, or I'm a bad CEO and the company dies, so it became life or death.

Guy Raz 36:06 Mm-hmm.

Brian Chesky 36:06 The stakes were too high, and I, for better or worse, I'm good in a crisis. I, I, I realized I could rise to the occasion, so I think it was the stakes that the moment... Like, you know, sometimes you have to rise to the moment. I think that's the second thing. And I think the third thing was, um- You know, this whole founder mode, this whole thing of, like, being in the details, being hands-on, that only came from the crisis.

Brian Chesky 36:31 I hadn't-- I had no notion I should do that. In fact, even Steve Jobs, I didn't think about after he died for like eight, nine years. It was only when we were-- people thought we were going out of business. I said, "Well, who else was almost going out of business?"

Guy Raz 36:46 Hmm.

Brian Chesky 36:47 Steve Jobs. Around the same time, I met Hiroki Asai, who was this creative director at Apple. I hired Jony Ive at, um, to... who was an industrial designer for Steve Jobs to work as a consultant for me, and they told me all these Steve Jobs stories, and that's when I really started studying him. I didn't-- I knew a little bit about him. I didn't know a lot about him. And so I studied... I first studied how did this guy, twelve weeks from bankruptcy, where it was, take the company out of this tailspin? And basically, what I realized is he got in all the details, he cut a bunch of projects, he made a lot of really hard decisions, and the single thing was he s- simplified. He was present, leadership was present, not absence. He was d- dictatorial, which seems like not something you should do. He said no more than he said yes. He was brutal about everyone going the same direction. He was exacting with standards, and he paid attention to every pixel, every word, and I did every... I decided-- And I, and I only did that to navigate the crisis, because in the crisis, I had to look through all of our expenses. You know, we had to be very, very hands-on.

Guy Raz 37:52 Yeah.

Brian Chesky 37:52 Basically, it was like we're all in the foxhole. So now I'm running the company hands-on for the first time in fifteen years. Not telling you what to do, but, like, we're in the foxhole together. We get out of the tailspin, and then I think a bunch of employees thought, "Okay, let's go back to operating the way we were," and I'm like, "No way."

Guy Raz 38:09 And operating you the way you were meant you had like-

Brian Chesky 38:12 Like, back off

Guy Raz 38:13 ... a bunch of-

Brian Chesky 38:13 Give us space now.

Guy Raz 38:14 And then direct reports, and you got your information.

Brian Chesky 38:17 Yeah.

Guy Raz 38:17 'Cause the other thing Steve Jobs would do is he would get his information from people deep in the co-

Brian Chesky 38:21 Skip level.

Guy Raz 38:21 Right. He had a hund- He, like-- He would gather

Guy Raz 38:23 a hundred people-

Brian Chesky 38:23 So here's something that a lot of CEOs do. They only talk to their directs.

Guy Raz 38:28 Yeah.

Brian Chesky 38:29 I don't wanna name the person, but I was-- I saw an interview of a CEO who a- appointed as his successor somebody who failed. And they asked him, "How come... You know, did you have a good relationship?" He said, "Yes." Then you go, "How come you didn't know-- What'd you miss?" He goes, "Well, I didn't talk to the people that he worked, that, that worked for him." I'm like, "Really?" And now this is a, one of the biggest companies in the world. At really big companies, these really corporate people, often they only talk to their own executive suite, and so it's called managing up. What I do is I skip level. I talk two, three layers down. Now, initially, you do that, you might piss off the dire- the executive. They might feel threatened.

Guy Raz 39:08 This started during, right after COVID.

Brian Chesky 39:10 Yeah.

Guy Raz 39:10 This, this was sort of the evolution of this.

Brian Chesky 39:11 I pissed off a bunch of execs.

Guy Raz 39:13 Yes. Because you were saying to them, "I'm actually gonna talk to the people who work for you."

Brian Chesky 39:16 And they said, "You're undermining me, you're going around me-"

Guy Raz 39:18 Of course.

Brian Chesky 39:19 "... you don't trust me. Um, what are you trying to do?" Yeah, not everyone-

Guy Raz 39:22 You're micromanaging.

Brian Chesky 39:22 Yeah, micromanaging. And-

Guy Raz 39:24 So what was your response?

Brian Chesky 39:27 I said, "We have to save this company," 'cause it was a crisis. So I was like, like, I was like, "Your feelings and how you feel has to come second to us saving this company."

Guy Raz 39:38 But they're saying, "Well, you what? You don't trust me? I'm telling you what you need to know. You, this is a waste of your time. You don't need to know this. You're the CEO. You've got to focus on big picture stuff. Let me do the details."

Brian Chesky 39:48 And that wa- that's what I did for ten, twelve years. And so I told them, "I tried this for twelve years, and look at where it got us. Look at where it got us."

Guy Raz 39:55 Well, you, I mean, but the company was doing well.

Brian Chesky 39:58 In sp- probably in spite of my leadership, not because of my leadership, is what I said. The company was chaotic. I mean, we had the curse of having too good of a business model. I joke that we had the curse of having too good of a business model. eBay versus Amazon. eBay had this great business model, so they didn't have to be great at execution. Amazon had this horrible business model, low margins. They lived and died by execution. Guess who won? The company that had great execution, 'cause they compounded. And so we succeeded in spite, often, of my leadership during those wilderness years, and I said, "We tried and failed."

Guy Raz 40:28 And that masked, you're saying, the, the business model-

Brian Chesky 40:30 Yes

Guy Raz 40:31 ... that was just l- it was lucky. It was really good.

Brian Chesky 40:33 Masked mismanagement.

Guy Raz 40:33 Mm-hmm.

Brian Chesky 40:34 My own mismanagement. It masked my own mismanagement. But the other thing I told execs, I remember one exec said, "Is this your job or is this my job?" She's like, "Do you wanna own it?" Or I remember saying to this person, "It should never be either," that this is not about me just delegating to you. This is not about you just, me telling you what to do. Like, the whole point is I'm not in the details telling people what to do. I'm in the details so I have the information. You see, every board of a public company has an audit committee.

Guy Raz 41:03 Yeah.

Brian Chesky 41:03 The word audit is key. It means they know every detail. If the board audit committee knows every detail, why wouldn't the CEO know every detail? And by the way, with AI, now you can. You can just prompt and find anything.

Guy Raz 41:13 Right, right.

Brian Chesky 41:13 And it's... AI is the ultimate skip leveling. I can know anything.

Guy Raz 41:17 And skip leveling, for people who don't know, it means literally going two, three levels down.

Brian Chesky 41:21 Yeah, to get information.

Guy Raz 41:23 And talk, right.

Brian Chesky 41:23 Because as you s-

Guy Raz 41:23 But how do you identify those people in an eight thousand person company?

Brian Chesky 41:27 So the way I did it is I picked key projects, and I would have the full chain of command in the room.

Guy Raz 41:32 Hmm.

Brian Chesky 41:32 Like, this project I care about, so I'm gonna have the person doing the work and all the managers in a line in the room. And then that way, you don't h-- the person doesn't have to wait to get all the managers' approval. I'll listen to everyone's opinion in the room, then I'll make the final decision. So a junior person doesn't have to go up the chain of command. The chain of command can disagree with them, and I can rule, overrule the entire chain of command. Now, usually I don't, and if I'm overruling the chain of command every time, either I have the wrong people or, um-

Guy Raz 42:01 They're not gonna wanna work for you

Brian Chesky 42:02 ... or they're not gonna wanna work for me. So hopefully I'm only overruling them, like, ten percent of the time. If I'm overruling them fifty percent of the time, I'm wrong or have the wrong people. If I'm never overruling them, I'm adding no value. And like-

Guy Raz 42:14 Yeah

Brian Chesky 42:14 ... and so I should be overruling people only occasionally, because you should be doing things not obvious. And so I basically, the final, to finish answering your question about being in the details, I said, "You know, you can call it micromanagement. I don't wanna, like, I don't wanna, like, put spin on the ball and pretend like it is what it is. I don't even know what you mean by that." I call it being in the details.

Guy Raz 42:36 Yeah.

Brian Chesky 42:36 I'm not gonna tell you what to do, but you're not gonna tell me to back off. We're gonna be in the foxhole together. And the idea is that we're gonna play ping-pong, and now you're gonna... I'm gonna, I'm gonna tell you an idea, you're gonna tell it back to me. We're gonna partner, and one plus one equals three. That together we're gonna come up with the best answer, and if you don't wanna collaborate, then you don't work here. In other words, I'll give you empowerment, but not autonomy. You'll have autonomy of h- of the way to do your work, like I won't tell an engineer how to code, but you're not gonna have autonomy over what direction to go.

Guy Raz 43:09 Hmm.

Brian Chesky 43:09 Because if everyone has autonomy to go in what direction, then everyone goes in different directions. That's bad. So you'll have empowerment, and this, people get this confused, empowerment and autonomy. People think everyone wants autonomy. I think people want empowerment. Empowerment means when I'm in the details, I can approve anything right away. You want resources? I'll give it to you. If somebody's blocking you, somebody in legal's saying you this, I clear the path. I like to joke to people that I'm actually like, like a offensive line. You're the running back, I'm the offensive line. I stand in front, and I clear the path for your idea.

Guy Raz 43:40 Hmm.

Brian Chesky 43:40 And if you have an idea, I'll put the weight of the company behind you. That is empowerment. That's not possible with total independence autonomy.

Guy Raz 43:47 I, this whole idea came to light when Paul Graham wrote his famous, now famous essay about the founder mode.

Brian Chesky 43:52 Yes.

Guy Raz 43:53 He saw a, a talk you gave at Y Combinator talking about this thing. It was a private talk, but you were basically saying, "I was told my whole career, hire great people, get out of the way."

Brian Chesky 44:03 Yeah.

Guy Raz 44:03 "And I, I learned or discovered that that actually wasn't working."

Brian Chesky 44:06 Right.

Guy Raz 44:07 "So this is what I decided to do. I decided to get into the details, really go deep, and just have my fingers in every pie-"

Brian Chesky 44:15 Yes

Guy Raz 44:15 ... as possible." How did you convince... I'm sure a lot of people left. I'm sure a lot of-

Brian Chesky 44:21 Yeah, a lot of people left

Guy Raz 44:21 ... your direct reports were like, "I don't wanna do this. I don't need this, and I wanna work in a more-"

Brian Chesky 44:24 Almost the entire exec team left.

Guy Raz 44:25 Wow.

Brian Chesky 44:26 Eventually.

Guy Raz 44:27 So how did you convince people that this is actually the way to go? How do you do that? When, when there's a, when conventional wisdom is, "No, no, this is how companies, big companies have to operate."

Brian Chesky 44:40 Well, the good news is you don't have to convince everyone. You just have to convince the people that are willing to stay, and you have to convince enough people to join. And a whole bunch of people were turned off by this. They left or they didn't want to work for me. And th- and I said, kinda similar to how in the early days not everyone wanted to use Airbnb, I said, "I don't need everyone to work for me. I just need 10 people on my executive team to work for me." So as long as I can convince 10 people to work this way and give it a shot, the way we'll really convince them is we'll deliver results. And if we keep delivering results, then it also, the way I'm gonna convince them is give this a try.

Guy Raz 45:12 There was a risk it could be wrong, though.

Brian Chesky 45:14 Yes. Although the data proved that founders, not all founders become great CEOs, but all the greatest CEOs were founders, from Sam Walton and Walt Disney to Steve Jobs to Jeff Bezos to Larry Ellison. I mean, we could go, we could go down the list. You know, m- we can go down the list. There's almost no exception to the rule that the best CEOs have that founder mode mentality, and they never lose that, and I think that's really, really important. And so the way I was able to convince people was just to say, "Give it a shot." By the way, I said, "We did it in the pandemic and it worked, so let's keep doing it."

Guy Raz 45:53 Hmm.

Brian Chesky 45:54 I also hired people from Apple. I hired people that worked for founders. There's the other thing. If you've worked for a founder like Jeff Bezos, I hired people who worked for Jeff Bezos, I worked with people that worked for Steve Jobs, they need no convincing.

Guy Raz 46:04 They understand.

Brian Chesky 46:05 They already understood. Where someone from, um, Procter & Gamble-

Guy Raz 46:09 Hmm

Brian Chesky 46:09 ... I didn't hire someone just picking a company, they would not understand because that founder has been dead for 100 years. People probably think I'm in all the details right now. I'm not.

Guy Raz 46:17 Yeah. You can't be.

Brian Chesky 46:18 I can't.

Guy Raz 46:18 There's too many.

Brian Chesky 46:19 So here's, here's the analogy I make. You aren't forever in all the details. That is not sustainable. It's like, this is a kinda cheesy analogy, you're like a golf instructor, and you watch their swing, and if somebody develops a bad swing, it's really hard to fix it. So you watch them 100 times, and at some point, the 101st time, it's muscle memory, and then you can let go, and then you can always, then you can watch them every 10 swings. At some point, it's just muscle memory. I remember the f- first time I went back into founder mode, we had to do a press release. We did like 70 iterations of the press release because it just, we couldn't get to excellence, and I said, "Well, we'll just keep doing this until we get to excellence." It was like 70, like, versions. And everyone was like, "Oh, we're never, ever doing this again." And I said-

Guy Raz 47:06 It was a press release?

Brian Chesky 47:07 It was one press release.

Guy Raz 47:08 S- okay.

Brian Chesky 47:09 So it's basically the idea is if this room's perfect-

Guy Raz 47:11 [laughs] Yeah

Brian Chesky 47:11 ... I'm gonna start by making this class perfect.

Guy Raz 47:13 Yeah.

Brian Chesky 47:13 Then I'm gonna make this little thing perfect.

Guy Raz 47:15 Yeah.

Brian Chesky 47:15 And so I said, "We're gonna make the whole company perfect by starting with one little thing." And people were like, "This is crazy. Why are you doing this?"

Guy Raz 47:22 Yeah.

Brian Chesky 47:23 I was trying to teach where the bar was. And now I just read it once because I've instituted the muscle. So to be very clear, founder mode is a way to teach people by staying in the details, by letting go only after it's muscle memory. And then you still see everything, but you do eventually let go. And so the mistake people make is they see people who have let go, 'cause there is excellence, and they don't understand that the way they got excellence was to be in the details.

Guy Raz 47:55 Hmm. How do you know... So here, we, we had Reed Hastings on the show a couple months ago, maybe a year ago, and, uh, you know, they, they have a famous, Netflix has this famous model, right? About how the-

Brian Chesky 48:03 Right, culture

Guy Raz 48:04 ... culture. And so it's, it's sort of a version of a question I asked him, but really applies here, which is there was a lot of friction. I can't imagine how much friction there was when you were kinda transitioning to this model. But when you have this model, right, and you have a vision of something, how do you make sure that people feel comfortable pushing back? Because you, even Steve Jobs, even God isn't right all the... Well, maybe God, but you can't be right all the time, and you have to know that, right? But you have a vision, you have an idea that you feel really strongly about How do you create an environment where people are willing to say, "I don't think so"?

Brian Chesky 48:51 Okay. Great question. A few things. The first thing is you have these, like, people that are willing to tell you the truth. Like, some people call it, like, CEO whisperers, right? There are, there are some people that are willing... They've been-

Guy Raz 49:05 Do you have them?

Brian Chesky 49:06 Yes, and most of them have been with me more than 10 years. So it's hard for someone who hasn't been with you for a long time. So it's good to keep some people around a long time. My co-founders, but also I have people that have been around for about a decade, um, or people that are s- they're, I have a few people that they don't need this job, and literally so that-

Guy Raz 49:24 Mm-hmm

Brian Chesky 49:24 ... like they can afford to, to-

Guy Raz 49:25 To say, "You're wrong"

Brian Chesky 49:26 ... say whatever and get fired or not be afraid. So that's the first thing, um, is that. But I'll give you a trick I do. Not a trick as in I manipulate them, but something I did recently. I was in London last week, and I was talking with my team, and we came up with a new tagline for the company. Our tagline used to be "Belong Anywhere," and I won't say what it is. We'll unveil it. I came up with a tagline, and I then texted my CMO and my two creative leads, said, "This is it. This is the tagline. We're doing it. I don't care what anyone says. We're doing it." And I, I felt certain. And I was like, and then I slept on it, and I realized they might not agree with me, but I'm so certain that I probably sucked all the oxygen out of the room. So the next day, I, I sent them a message and I said, "I realized I got really excited. You have two weeks. I want you to come up with a better tagline. I think there's a better tagline."

Guy Raz 50:19 Hmm.

Brian Chesky 50:19 So I actually took the opposing position. I don't think this is the tagline. I think there's a better tagline. Two weeks later, they came back to me, or a week later, 'cause I, it was London, was last week. A w- they came to me... Sorry, I said that you have two weeks.

Guy Raz 50:31 Yeah.

Brian Chesky 50:34 They cut the time in half. They said, "We're, we're already down with the process, and we actually think the original tagline is the right one." But in other words, you, you can take the counter position. You give them permission to disagree, and sometimes when you give permission to disagree is you actually change your mind. You might say, "We're doing this," they say, "Actually, maybe do this." And if they keep agreeing with you every time you change your position, now you know they're not comfortable.

Guy Raz 50:58 Yeah.

Brian Chesky 50:58 You also have to, um, you know, you have to ask people their opinion. Sometimes you ask their opinion before you give yours. So if I see something, if I say, "This is great," everyone in the room's gonna be like, "Oh yeah, it's great."

Guy Raz 51:08 Yeah.

Brian Chesky 51:09 So I'll ask them, and they don't even know what the right answer is. If the right answer is my opinion, they just have to give their opinion. Well, maybe their opinion's the right answer. So often you give your opinion last, you have whisperers that can tell you the truth, you can take the counter position, um, or you ask people like, "What's my blind spot?"

Guy Raz 51:29 W- like, let's say you're, you're reviewing a project. Like a team's been working on something for six months and you don't like it, and you gotta kill it. H- what happens? What do you do? How do you do it? Do you, do you, do you try to prevent that from happening in the first place?

Brian Chesky 51:44 Yeah. If a team's been working on something for six months and I have to kill it, I failed as a leader that they've gone six months down a journey and I've had to pull the plug. This is why you should be in the details. Because you never... I like to say I wanna be at the beginning and end of the process.

Guy Raz 51:57 Hmm.

Brian Chesky 51:58 And in the middle, I check in. The reason comp- projects go in the wrong direction is because of one of two reasons. They start wrong, they're not set for success, or they are off an island without oversight. I- in the wrong direction as in something you're unhappy with. If those two things aren't true, then you'll never, ever have that problem. So the first thing is you have to set somebody up for success. Do we have a clear vision of what we're trying to do? Are the right people working on it?

Guy Raz 52:26 Hmm.

Brian Chesky 52:27 Is there a clear, directly responsible individual? Do we have all the resources? Do we have total alignment on what we're gonna do? Do we have the right process? Are we trying to do something too big or too small? And this is, this is like a whole checklist of things you do. Okay. So at some point, the project's set up for success. Now you have to create a rhythm, and a rhythm can be every day, every week, every month.

Guy Raz 52:47 Yeah.

Brian Chesky 52:47 But you have to establish a rhythm.

Guy Raz 52:49 So how many projects could... Do you have the capacity to be involved with at any given time?

Brian Chesky 52:55 A couple dozen, maybe 20. But they're all... Not 20 a day.

Guy Raz 52:59 Yeah.

Brian Chesky 52:59 Um, probably 20-ish, and at different rhythms. So maybe there's two projects, two or three at a time where I have a daily rhythm, and then other projects I have a weekly or biweekly rhythm, and every other project I have a monthly rhythm. Um, and if I'm not meeting it monthly, then I'm really, I would call myself not involved.

Guy Raz 53:17 All right. Let me ask you a couple questions about, specifically about Airbnb and about where it's heading, right? Um, there are a lot of opportunities, right? And I, and, and the company's core business model remains, right? It's bookings and obviously there's some, you know, I know independent hotels and things like that. I fly United a lot, so I get to board early and I get other perks. If I'm not staying at an Airbnb, I get, and I, I book through Chase, I get the edit or whatever. A lot of people use Marriott because of loyalty points. Is there something about those models that's interesting to you that you think... I mean, Marriott is basically a loyalty points company.

Brian Chesky 54:00 Yeah.

Guy Raz 54:00 They don't own buildings. They don't-

Brian Chesky 54:01 People don't realize this, but Marriott's basically a loyalty program company.

Guy Raz 54:04 Right. And it's, it's what works for them, right? We know these loyalty programs work. I think they were started with casinos back in the '70s or '80s. Is, is that interesting? Is that something that I know at times has been discussed, but is that s- a potential, you know, growth area?

Brian Chesky 54:24 Yeah, absolutely. There are three things I said I'd never do. Um, the first is I said I'd never do advertising. Somebody once said in the design community, "Advertising's the price you pay for being unoriginal."

Guy Raz 54:37 Hmm.

Brian Chesky 54:38 And so I'm like, "We don't do advertising." And then we started doing advertising, and it turns out when you sell something, no matter how original you are, and Tesla's an exam- uh, exception, but even Apple and Disney and Nike, very Inspirational companies have to do advertising

Guy Raz 54:53 You gotta remind people

Brian Chesky 54:54 I said we'd never do hotels. And then our-

Guy Raz 54:56 You bought hotels tonight

Brian Chesky 54:58 We bought hotels tonight. And the reason why is 'cause our customers told me, and I realized this is my ideology. And actually, the only reason I was even anti-hotels was because Airbnb was like competition. I'm like the Red Sox, you're the Yankees, and I wasn't seeing it clearly, and people like hotels. And I had to be honest that actually, half the hotels in the world are independents. BnBs are technically categorized as hotels. It's in our freaking name. And a lot of our guests, more than half of them, do occasionally stay in hotels, so why don't we have them? And the third thing I said, I really pushed against the loyalty program, is I said, "The best loyalty program is people just loving your pr- your product."

Guy Raz 55:33 Yeah

Brian Chesky 55:34 Again, I don't think Disney, Apple or Nike, these three companies we were talking about, had a loyalty program, and I've revisited that. So you see there's a pattern here of me saying I'll never do something and then-

Guy Raz 55:44 Yeah

Brian Chesky 55:45 ... having to become more practical, which is maybe another version of going from a founder to CEO, which is becoming less ideological. You wanna have a company that's got a cult-like following-

Guy Raz 55:56 Mm

Brian Chesky 55:57 ... but it's not ideological, where it's so impractical, it's actually a cult, then you're gonna get in deep trouble. So you have to have this practicality. And so I can't say too much except to say that we are looking at this type of program, um, but we aren't gonna do something out of the tube. Airbnb never does. So w- if we were to do something, it would be very original, very cool, very different and, um, and that's what I can say.

Guy Raz 56:22 Okay. I know that you guys are going to... You have an, an initiative. You're gonna fund a million nights for free for people in distress or, you know, displaced by natural disasters. I think your... The plan is to put a half a million dollar... Sorry, half a billion dollars-

Brian Chesky 56:38 Yeah, $500 million

Guy Raz 56:39 ... into this, because this is part of, um, a nonprofit, Airbnb.org, that actually I think started around Hurricane Sandy-

Brian Chesky 56:44 It did

Guy Raz 56:44 ... or came out of that time.

Brian Chesky 56:46 Yeah.

Guy Raz 56:46 So tell me about, about this.

Brian Chesky 56:48 This is 18 years in the making. In 2008, I emailed my co-founders. The subject line of the email was Airbnb.org. Airbnb hadn't even launched yet, and we already had the idea for Airbnb.org. And the base... So we didn't quite know what it meant, but we kinda thought it was gonna be something around housing. In 2000 tw- nothing happens for four years, 'cause now we got, we got our hands full. 2012, Hurricane Sandy hits. A woman emails us. She said, "I wanna host one of the disaster evacuees. I wanna host for free." We had to change our system to allow her to do that. That began an effort of whenever there's a disaster, we would try to respond. We couldn't do many, but we started responding to disasters. Now, some hosts opened their homes for free. A bunch of people would need to get paid, so we started raising money or using our own money to f- pay the hosts to make sure the guests could stay for free. This happened disaster after disaster after disaster. Then Afghanistan.

Guy Raz 57:43 Hmm.

Brian Chesky 57:44 Tens of thousands of refugees needed housing. We housed 20,000 Afghan refugees. Russian invades Ukraine. There's millions of refugees. We housed 100,000 refugees for free. LA fires broke out. We provided 70,000 free nights in LA. And so now what people don't realize is we have this nonprofit, Airbnb.org, where we house people for a natural disaster every other day, about 170 disasters a year. We house thousands of people. Medical stays. My mom in 2011 had cancer, breast cancer. Thankfully, she's okay now. She was living in Albany, and she'd take the Amtrak train to Sloan Kettering in New York City every day. And apparently, she's told me there were other people that would go every day on the train, and they'd go every day on the train 'cause they couldn't afford to stay overnight in New York-

Guy Raz 58:32 Hmm

Brian Chesky 58:32 ... 'cause of how expensive the hotels were. My mom had the idea, you should provide h- medical stays, free stays for people getting medical treatment. So we eventually did that, and now we have medical stay treatment. So if you wanna get treatment, or let's say a child's sick in a children's hospital in Mexico City. This is where we launched it. Parents want to stay with the children, but they couldn't afford to stay in hotels. So now the child's alone in the hospital and their parents aren't there. But we could put them in a house for free near the hospital, and they can visit the child every day, and this obviously is really good for the child, but also really good for the parents.

Guy Raz 59:03 Hmm.

Brian Chesky 59:04 Domestic violence victims. What happens when you're a victim of domestic violence? Where do you go? A shelter? That's not a very good living condition. What if you could be at a home where a family could take care of you? So we started realizing whether it's natural disasters, refugees, medical stays, or domestic violence, there's a lot of people that need housing. And my parents taught us simple, simple, "Brian, just be useful in life. Be of service to someone else." In fact, one of my favorite designers is Charles Eames. He said, "The role of a designer is that of a very thoughtful host anticipating the needs of his guest." So therefore, let's be of service to others. Let's take the one thing we know how to do really well, provide housing, and let's house people in need. That's our superpower. And we decided to do that. We are able to scale it, and so I asked our leader, "What's the biggest possible scale we could pull off operationally?"

Guy Raz 59:57 Hmm.

Brian Chesky 59:57 He said, "I think in a few years we could h- house a million nights worth of free housing, which would probably make us the largest organization in the world that provides free housing, bigger than the Ronald McDonald House, which has been going on for, like, 40 or 50 years. Bigger, I think, than any government." I said, "Well, what would that cost?" It turned out it would cost about half a billion. I said, "Well, it's not my money. It's the company's money. We're a public company. Could we do that responsibly in the interest of shareholders?" And I think we ultimately came to the conclusion we're gonna do it, and I think it's-

Guy Raz 1:00:28 Hmm

Brian Chesky 1:00:28 ... good business to do good in the world, and I think that, um, that's what we're gonna do. We're gonna try to house a million nights for free a year over the next five years. And you know, I think this is gonna be one of the most important things the company ends up doing in its, in its lifetime.

Guy Raz 1:00:42 Um, normally I ask our founders on, on the show, founders on the show how much of their journey do they attribute to luck and/or success. I'm not gonna ask you that question. You can answer that question, but I, I looked back on my interview with Joe 10 years ago, and I asked him, I said, "Can you imagine a time when you aren't involved with the company?" You know? And, and he, you know... Or, "What would you do if you weren't working?" And, and he, he answered the question three different times. Started and stopped, and started and stopped. Um, because I think it was a tough thing for him to think about back then. And obviously he's moved on. He's still involved, he's on the board. You're 45, I think, now, right? I mean, you've been doing this for a long time.

Brian Chesky 1:01:24 19 years.

Guy Raz 1:01:24 You've had incredible professional success. Can you, could you imagine, um, a, a, a future where you're not here? Does that, is it a part of that appeal to you? Does it scare you? I don't know. What do you, what do you think? I mean, where are you going to be in 10 or 20 years from now?

Brian Chesky 1:01:45 I'll answer that with, like, a story of my heroes. Leonardo da Vinci, Steve Jobs, Walt Disney, Sam Walton, Vincent van Gogh, though he died early. I could... Frank Lloyd Wright. What do they all have in common? All five or six of them worked the last week of their life. Walt Disney was dying of lung cancer, laying on his hospital bed, looking up at the ceiling tiles while his brother was rubbing his cold toes. He was plotting out Disney World. I know numerous people that visited Steve on his deathbed, and he was, he was survi- he was surrounded by family, family was most important, but he still cared about Apple. Leonardo da Vinci carried the Mona Lisa with him till he died. It was never even on display. Now, some people could hear that and say, "That's really grim. You're working the last week of your life." But if you love it, it's not grim at all. They would've loved it. And it doesn't mean you're not available for your family. I think the most important thing at the end of my life is I have family surrounded by me. But I hope not long before that I'm still doing something I love.

Guy Raz 1:02:51 Here.

Brian Chesky 1:02:51 I hope so. Now, who knows? With AI, if I'm like 100 years old, I probably shouldn't be running a tech company. So it's really about how long I live. But I hope that if I live longer than 20 years more, and I hope that I would, I hope I'd still be doing this. Because my heroes were doing it, and I just love it. And I know parents, my friends' parents, where some of them retired and some didn't. The ones that retired got older a lot faster-

Guy Raz 1:03:18 Yeah

Brian Chesky 1:03:18 ... than the ones that didn't. And so whether I'm doing this or not, I'm always gonna be creating. I'm always gonna be building. And I'm not doing it anymore for adulation. I'm certainly not doing it for money. Can't spend what I have. I'm doing it 'cause I love it. It's because, like, it's, I, I have one of the largest canvases any artist or designer's ever g- been given in human history, and it's, it's, it was probably a bunch of luck. I don't think getting from 2016 to here was luck, but I think Joe and Nate, the idea, people... What was luck was getting the shot. There are so many people as talented as me or more talented that never got the shot. I got the shot. What wasn't luck was then I got, I gave myself the training. Now I have the skill. That was just hard work. But getting in the door, that was pure luck. Getting in the door was luck. Now that I'm in the door, in the club, I don't wanna leave, because I feel like I have, like, 20 years of ideas. And whether it's all these problems I see in the world, all these ideas, all these dreams, I just envision a more creative, magical world than the one we live in. Now, whether or not people wanna live in that world is, or, or they wanna participate in creating that world is, is up to them, and it's not up to me. It's up to me to convince people that this is compelling. But I think I'm gonna be doing this for a long time, you know. And, you know, one of my other heroes is Pablo Picasso, and, or at least he had a lot of good quotes, Pablo Picasso.

Guy Raz 1:04:46 Mm.

Brian Chesky 1:04:46 By the way, he painted till the end of his life. He had so many great quotes, but he said, "All children are born artists. The problem is to remain an artist as one grows up." He also said, "It took me four years to paint like Raphael, but a lifetime to learn to paint like a child." I wanna stay young the rest of my life. And the thing is, therefore I wanna have a childlike, not childish, but childlike quality. I wanna remain an explorer. I wanna learn, I wanna grow, I wanna keep making new... Every y- every year of my life I wanna make at least one new friend. I wanna keep creating till the end of my life. I wanna keep connecting and helping people till the end of my life. I don't know how long that is, but I just wanna just keep creating, keep painting on this giant canvas I've been given. And so long as I have this canvas, I'm not gonna stop painting.

Guy Raz 1:05:34 Thank you.

Brian Chesky 1:05:35 Thank you.