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

This episode is available on Youtube: https://youtu.be/ZYf-DfxJg1c Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time. But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it. Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too. In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how Airbnb.org is providing free housing to people in crisis—and why Brian wants to expand that effort to one million nights a year. What You'll Learn How an art school graduate with no business experience became the CEO of Airbnb Why Brian describes himself as “naturally a great founder but naturally a terrible CEO” How following conventional leadership advice created chaos inside Airbnb Why Brian believes "hire great people and get out of their way" can be a death sentence for startups How losing 80% of Airbnb's business during COVID forced Brian to reinvent his leadership style What studying Steve Jobs taught Brian about getting into the details How Barack Obama helped Brian understand and confront his loneliness Why reaching a $100 billion valuation left Brian feeling empty How Airbnb.org grew from helping people displaced by Hurricane Sandy into a global nonprofit—and an ambitious plan to provide one million nights of free housing annually How Brian thinks about Airbnb's future—and why he has no plans to stop building Timestamps: (00:03:23) - Airbnb goes public at a $100 billion valuation, but Brian wakes up feeling empty (00:06:05) - From art school to Silicon Valley: How Brian became an unlikely tech founder (00:10:37) - "I was a great founder and a terrible CEO": Brian's early leadership mistakes (00:13:21) - Why hiring experienced executives and getting out of their way didn't work (00:17:59) - The self-doubt and chaos of running a fast-growing company (00:23:41) - How Barack Obama helped Brian confront his loneliness and reconnect with old friends (00:33:55) - Why Airbnb's early success led to overconfidence and costly distractions (00:38:10) - COVID wipes out 80% of Airbnb's business—and forces Brian to change (00:40:05) - What Brian learned from Steve Jobs about hands-on leadership (00:47:44) - Why Airbnb's leadership overhaul drove away much of its executive team (00:50:54) - The 70 revisions of a single press release that helped Brian redefine excellence (00:52:12) - How Brian gets honest feedback from employees who might be afraid to disagree (00:57:38) - Why Airbnb is reconsidering some of its long-held beliefs about its business (01:00:48) - Airbnb's plans to provide free housing for people in crisis (01:05:09) - Why Brian hopes to keep building for the rest of his life Production Credits Our production is handled by Podcast Pointman. Follow How I Built This: YouTube → @HowIBuiltThis Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  It was a crucible moment. It was the first moment I had to be a good CEO. It was a life or death moment because 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.

• 0:26Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 0:38Guy Raz?

  I'm Guy Raz, and on the show today, how Brian Chesky went from an art school student with no business experience to the CEO of Airbnb, a company worth more than $100 billion, and why building Airbnb turned out to be a lot easier than learning how to lead it.

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• 1:41Guy Raz?

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• 2:23Guy Raz?

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• 3:04Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt.

• 3:33Guy Raz?

  About 10 years ago on this show, I interviewed Joe Gebbia, one of the three founders of Airbnb. And Joe told me the incredible story about how he and his friends, Brian Chesky and Nathan Blacharsky, turned a few air mattresses on the floor of a San Francisco apartment into a business that transformed the travel industry. It is one of my favorite stories we have ever told on this show. And today, we're picking up where that story left off. Now, I've interviewed plenty of founders who spent years, sometimes decades, struggling to get their ideas off the ground. Colin Engel, for example, who, by the way, grew up in the same small town as Brian Chesky, spent more than a decade trying to find the product

• 4:15Guy Raz?

  that would make iRobot a success, which, if you don't remember, it was a Roomba. But Airbnb wasn't really one of those stories. Sure, there were some very difficult early days. But once Airbnb found its footing, it took off, and it became one of the most successful startups of all time. Product market fit, timing, and great leadership, right? Well, not according to Brian. In fact, he now says Airbnb succeeded in spite of his leadership, not because of it. Brian's been CEO from the very beginning. He was just 26 when they started Airbnb, and today he's 45. And he's spent almost his entire adult life learning how to lead the company he created.

• 5:00Guy Raz?

  Brian grew up in upstate New York, the son of two social workers. Before Airbnb, he'd never run a company, and he'd never been to business school. So to help him run the company, he hired experienced executives and deferred to their judgment and watched as the company became increasingly sprawling and difficult to manage. But then came the pandemic. And here's what he told me the first time we spoke back in the summer of 2020.

• 5:26Speaker 00

  We spent 12 years building Airbnb, and then we lost 80% of the business in eight weeks.

• 5:31Guy Raz?

  All of a sudden, Brian had to figure out how to save the company he'd spent more than a decade building. What followed was a major transformation, not just in how he runs Airbnb, but in how he looks at leadership, success, and his own life.

• 5:50Guy Raz?

  I want to start on December 10, 2020. Airbnb goes public at an amazing value. I think by the end of the day, the company is worth over $100 billion, 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.

• 6:12Speaker 00

  The day after.

• 6:13Guy Raz?

  Yeah, why?

• 6:14Speaker 00

  Well, first of all, the IPO was a weird experience because it was on Zoom, because of 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 $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 in my house. It's still the pandemic. I'm still sheltering in place. I wake up, put on sweatpants, I get on a Zoom meeting. We just have like some meeting, we're in a meeting. And it was, it was, it was almost like, I felt like my whole life

• 6:56Speaker 00

  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. I don't feel that much happier than I did the day before. It was a rush, 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. But 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.

• 7:40Speaker 00

  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. I mean, 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 mountains do I even climb? And that began a whole nother journey, which is, 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.

• 8:22Speaker 00

  We started, it was 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.

• 8:33Guy Raz?

  I want to get back to that later on because I know that, 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 gonna start a company together someday. That's what he said, he told us, he told you. And they're gonna write a book about it. Do you remember that?

• 9:07Speaker 00

  Yeah.

• 9:08Guy Raz?

  He said this to you in Rhode Island the night before you graduated.

• 9:11Speaker 00

  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 they, it was really funny, because they, they had like pineapple pizza and all these like exotic types of pizzas. Yes, 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, it was a little random. Not that maybe we started a company together, but the prescience of they'll write a book about it, because there were a few books written about it.

• 9:52Speaker 00

  But I think, I want to give credit to Joe, because, 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. I don't know quite what it was. That's the 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 that I became, I went to Rhode Island School of Design as an artist.

• 10:22Guy Raz?

  Yeah.

• 10:23Speaker 00

  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 supposed to be in this party.

• 10:33Guy Raz?

  I think your dad, I read that your dad said to you, because he said, I want to be an artist, he was like, just make sure you get health insurance, please.

• 10:38Speaker 00

  Yes. And my high school yearbook quote, it's a very weird yearbook quote. My yearbook quote was, I'm sure I'll mount to nothing. It was half a joke.

• 10:46Guy Raz?

  Yeah.

• 10:47Speaker 00

  Because I thought all the yearbook quotes are kind of ridiculous, people are like taking themselves too seriously. But there had to 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, 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, we 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

• 11:32Speaker 00

  one of the greatest business models on the internet. And it turns out, I am now 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.

• 11:49Guy Raz?

  Yeah. You eventually, you go to LA for a couple of years, and, but Joe manages to convince you to come to San Francisco, where he's living, with Nate, his roommate. And eventually, he wants to fulfill this. He really, I mean, he says to you, we're gonna start a business.

• 12:03Speaker 00

  Yes.

• 12:03Guy Raz?

  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, you start this company, you be, 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 did they see you doing that?

• 12:27Speaker 00

  I saw myself as a leader of like five people, you know, maybe 10 people. I remember saying, everybody'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 have been the scale that Joe and Nate believed in me, that I, that was hard for me to see in myself.

• 12:46Guy Raz?

  We, 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 can hear that on our, 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. And if I think about where I was 30 years ago, I sucked at what I, 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 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

• 13:30Guy Raz?

  two designers in a tech city.

• 13:32Speaker 00

  Yes.

• 13:33Guy Raz?

  Trying to convince people that you know what you're

• 13:34Speaker 00

  A shot of water.

• 13:35Guy Raz?

  Doing, and you're trying to learn how to hire people, how to tell them what to do. And what do you, what do you remember about, about just learning those things? And, and how it kind of evolved in those first few years?

• 13:58Speaker 00

  Here's what I would say, guy. I think I was pretty much naturally a great founder, and I was naturally a terrible CEO.

• 14:06Guy Raz?

  Which is, which is a very classic story.

• 14:08Speaker 00

  I, 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, 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 on our belt.

• 14:52Speaker 00

  And then suddenly, you gotta be the 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 grownups that don't understand your stage.

• 15:17Guy Raz?

  Yeah.

• 15:18Speaker 00

  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.

• 15:40Guy Raz?

  That's really hard.

• 15:41Speaker 00

  Not, you know, being, becoming profitable.

• 15:45Guy Raz?

  Yeah.

• 15:45Speaker 00

  Expense management. This stuff is, this stuff is easy.

• 15:48Guy Raz?

  I, I interviewed a CEO many years ago, really excellent CEO, and he said, and, he said, the job of a CEO is not to have the answers, but to identify the people who do have the answers.

• 16:00Speaker 00

  I think that.

• 16:01Guy Raz?

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

• 16:08Speaker 00

  Yes.

• 16:08Guy Raz?

  Much, much older than you, right? And so, first of all, before we kind of dig into some of those experiences, because I know what will, what would eventually happen, right? What was that like for you to have? I mean, was it intimidating, you know?

• 16:21Speaker 00

  Yeah.

• 16:21Guy Raz?

  To have people who, who were coming in, they're like, Brian, I got it, here, you know, like, 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?

• 16:33Speaker 00

  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, 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

• 17:16Speaker 00

  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.

• 17:36Guy Raz?

  But you didn't know that at the time.

• 17:37Speaker 00

  I didn't know any of that.

• 17:38Guy Raz?

  So, they were making decisions, and probably some of the decisions were good.

• 17:41Speaker 00

  Yes.

• 17:41Guy Raz?

  But your instinct was to defer, because

• 17:44Speaker 00

  Completely defer.

• 17:44Guy Raz?

  You didn't want to seem like you were arrogant, like you were know-it-all.

• 17:47Speaker 00

  I was a little intimidated. And, yeah, 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.

• 18:04Guy Raz?

  Very normal.

• 18:04Speaker 00

  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.

• 18:17Guy Raz?

  Conflict averse, too?

• 18:19Speaker 00

  100% conflict averse. In 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. 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.

• 18:41Guy Raz?

  Right.

• 18:41Speaker 00

  And as a coach, I kept hoping the pitchers would take themselves off the mound. Like, you're getting five home runs, it's now obvious. No one ever comes to you and say, I'm 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're responsible if they're not doing a good job, because you're the one who 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, so I gravitated to people that weren't 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.

• 19:22Speaker 00

  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.

• 19:38Guy Raz?

  Yeah.

• 19:38Speaker 00

  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.

• 19:50Guy Raz?

  Yeah.

• 19:50Speaker 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 got to basically fix that thing. And so you might've hired someone, they've gone down the 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, there are people. And that direction is our direction, not your direction. Because I have to live with it long after you do.

• 20:28Guy Raz?

  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 day. Were you ever, did you ever think, maybe I'm not right, the right person to do this?

• 20:42Speaker 00

  Yeah, all the time.

• 20:44Guy Raz?

  All the time.

• 20:44Speaker 00

  All the time. I will, 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.

• 21:02Guy Raz?

  But what would you tell yourself?

• 21:03Speaker 00

  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 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? Um, I must not have this ability, but I'm going to just do my very best. Cause I don't, I don't know what to do. I don't, you know, I looked for like presidents and COOs. I hired those types of people. 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. And the company, to be clear, wasn't like, like do nose diving. It was still growing.

• 21:47Guy Raz?

  Yeah.

• 21:48Speaker 00

  But it was clearly not like, like it really, 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 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 no's.

• 22:32Speaker 00

  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 our motto of ships going in different directions because we have no leverage.

• 22:44Guy Raz?

  Yeah. I mean, it would take you years to discover that. And that is what like, that's what age and wisdom, right?

• 22:50Speaker 00

  Yeah.

• 22:50Guy Raz?

  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 described it, there's still chaos. What was the thing that kept you saying to yourself, no, I'm going to stay doing this? Right? Cause it's really, it is, I mean, there are, you've 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, was there a mentor who said, you, you should stay, you should keep doing this.

• 23:35Guy Raz?

  You're going to get better at this.

• 23:38Speaker 00

  Such a good question.

• 23:41Guy Raz?

  What do you remember? Cause I would've left. I would've 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 bullshit.

• 23:52Speaker 00

  A couple of things come to mind. The first is, um, my dad.

• 24:00Speaker 00

  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, I'm five eight. So I played ice hockey and I hit puberty late. And I went to this, 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, with this young little guy that was like five seven, it was a walk in Notre Dame. And that was my hero. I was the underdog. My said, my dad said, just, it's not the size of the dog in the fight. It's the size of the fight and the dog that matters. That he used to say that to me all the time. A hundred percent 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.

• 24:45Speaker 00

  Now, if the board or the world told me, please stop, I would've. If Joe and Nate said, Brian, I need to take you off the mound, I would've 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, not, um, beyond the IPO, my darkest actual professional moment was the pandemic hit. I remember Ken Chenault, CEO of Amex, was on our board. He was CEO of Amex during nine 11, 2008. He said, Brian, sometime in your career, you're going to have to deal with the nine and 11 or 2008. It was literally March 15th, Ides of March.

• 25:21Guy Raz?

  Wow.

• 25:21Speaker 00

  Ken calls me, said, remember nine 11? This is going to be 10 times the size of nine 11 for travel, as far as impact and it was. We lost 80% of our business in twelve weeks.

• 25:29Guy Raz?

  I remember, we interviewed you that time. You said, we spent 12 years building this business and we have lost 80% of it in a matter of weeks.

• 25:37Speaker 00

  Eight weeks. And I didn't, and people were asking, is this the end of Airbnb? Is Airbnb 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. If 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, I, I didn't mention this, the first question I asked about the IPO. The thing that really, I think, got me down was how lonely I was.

• 26:22Speaker 00

  The job of a CEO can be so lonely. See, being a founder, if you have co-founders, it's not lonely. In fact, when you're a co-founder, you have your friends, you're in it together, you're, no one's really in charge. You hire your friends. They are young, in your twenties. You go out drinking together, you hang out together. It feels kind of like a, like a college, like crew.

• 26:41Guy Raz?

  Yeah.

• 26:42Speaker 00

  And then you become CEO. You're not supposed to like socialize your employees as much. Your employees have families, so they're not going to hang out with you. You know, everyone's looking 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 to be the principal of your own high school. And you're like, wait a second. And everyone in the school's talking about you. And every time you walk in 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.

• 27:24Speaker 00

  And that I had to like reconnect with myself, my purpose, like why am I even doing this? I'm not doing this to be, to, 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 dollar company. Like it's just, it's, it's an idea. It's like a, 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.

• 27:54Guy Raz?

  You wrote him a letter, right? In the middle of this?

• 27:56Speaker 00

  A middle of this.

• 27:57Guy Raz?

  You reached out to him and, and asked?

• 27:59Speaker 00

  For help.

• 28:00Guy Raz?

  Yeah.

• 28:01Speaker 00

  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, um, he said like, he said, I remember him saying, like, I have 15, 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 were 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? Cause a lot of like celebrities lose their mind. A lot of rich people lose their mind to 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, 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.

• 28:46Speaker 00

  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 held 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. Cause 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 on you, just becoming too busy for things that

• 29:29Speaker 00

  seem unimportant, like relationships, which are the most important things.

• 29:33Guy Raz?

  That's the thing. I mean, here you are, and, and I remember we, 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. 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 backseat.

• 30:03Speaker 00

  I had no personal life.

• 30:03Guy Raz?

  It becomes much more complicated, right? And complex to try to build one when you are known and all of these things.

• 30:11Speaker 00

  I would walk down the street and I wasn't famous, but I would hear people say, that's the Airbnb guy.

• 30:17Guy Raz?

  Yeah.

• 30:18Speaker 00

  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, 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 about you. 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 want to learn about Airbnb. 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 two in your head and you stare at things,

• 31:02Speaker 00

  you can start to like, just kinda, like an artist has to step away from the canvas. And if you stare at something too long, you kind of start getting stuck in iterative. And, um, 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.

• 31:26Guy Raz?

  So what did you do?

• 31:29Speaker 00

  The first thing I did is I called 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 shit 15 years ago.

• 31:45Guy Raz?

  Yeah.

• 31:45Speaker 00

  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 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 with yourself, solitude. Then family, maybe call it five people. Then the next concentric circle is 15 people that 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,

• 32:30Speaker 00

  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 from people I'm working with. And the pandemic made it worse because I didn't live 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.

• 33:13Guy Raz?

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• 33:58Guy Raz?

  with Stripe's users processing a combined $1.9 trillion last year. So if you're already thinking about what's next for your business, see what's possible at stripe.com.

• 34:16Guy Raz?

  But how do you know, how do you know who to trust, right? Especially when people know the value of the company, what that means for you.

• 34:25Speaker 00

  Yeah.

• 34:25Guy Raz?

  You're well-known. You know, you are like, I met my, my wife when I was 24. 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.

• 34:50Speaker 00

  Yeah.

• 34:51Guy Raz?

  But you've got to now, but you're now known. And there are consequences in trusting people who violate that trust.

• 35:00Speaker 00

  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 it wouldn't be in my life, but I would assume good intent. Said differently, there are some people I met in Silicon Valley that said, no new friends. Cause only I can trust my old friends. The problem is when you don't have new friends and there are people, I bet you people watching their 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 going to take the risk. Now, maybe I'm not going to like, you know, send them my bank account information and like, you know,

• 35:43Speaker 00

  like, like, you know, I'm going to 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? A hundred percent. 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 I don't know who to trust. And my only answer is you got to give people a chance. Now, you know, one way to know how you can, like, there's some tactics you can do. If people are really, the more successful you get, the nicer everyone is to you.

• 36:26Speaker 00

  So you start to become a bad read of character because everyone's really nice to you. So we have to pay attention to how nice they are to other people. And so one of the things I used to do is I asked my assistant how nice people were to her. Cause there were people that were very obsequious and unkind to me. And they were really, they wouldn't treat her well.

• 36:44Guy Raz?

  But your default was to trust.

• 36:45Speaker 00

  My default was to trust.

• 36:46Guy Raz?

  Yeah. And just wherever the consequences land, they land.

• 36:50Speaker 00

  They land. And, and, and I think you're going to get hurt. It's like saying, I'll never date because I don't want to be in a relationship because I want to date because if I date, someone might break my heart. Well, what's worse, having your heart broken or like dying alone? I don't know. You pick your poison.

• 37:05Guy Raz?

  Yeah.

• 37:05Speaker 00

  So the same thing with fail. I don't want to start a company because it might fail. I don't want to like hire this person because it might not work out. I don't want to exercise, I might get hurt. I might, I might injure myself. I don't want to live my life because I might die. It's like, you're going to die anyway, might as well live.

• 37:20Guy Raz?

  I looked over the transcript from our interview in 2020 during COVID. And you said, at the time, you said that Airbnb had become stretched and sprawling. Those were your words, 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?

• 37:40Speaker 00

  Yes.

• 37:40Guy Raz?

  As, as you kind of began to rethink how you wanted to organize your life, your role, this company. What, what do you think, you know, why do you think that what, 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?

• 38:11Speaker 00

  Actually, it was a, I think, I actually think it's a very different thing that I also suffer from, which is hubris. I think that I see this a lot. You have a hit. So I had the good fortune of like Joe and I and Nate, we romanticized 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 be to both grow something and start something new at the same time.

• 38:51Guy Raz?

  Yeah.

• 38:52Speaker 00

  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 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,

• 39:35Speaker 00

  a little bit of overconfidence, and a little bit of indulgence. You know, it's like you have an abundance of money. You have an abundance of resources. Yes, you get pressured to expand. But a lot of what we do as founders is we, we, we, we always have the ability to suffer from hubris. We have a hit. And we go from like being, we have no money, you're really disciplined. You say no, 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 judgments are, judgment can go down. And you start thinking into everything, you have sloppy thinking, you get, you get sloppy. And you just start throwing money at things. And you see what sticks.

• 40:19Speaker 00

  And I don't want to 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 know how to manage, there's chaos. Everyone's got a new manager every few months. You're doing everything but nothing well.

• 40:46Speaker 00

  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, 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 kind of made it worse by perpetuating even more things. And it just, it just gets worse and worse and worse. And at some point, your castle becomes your prison. And you basically build this beautiful castle, and 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.

• 41:30Speaker 00

  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.

• 41:36Guy Raz?

  When do you remember, I mean, was it during COVID or before, when you, 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. And you've had mentors, right? And President Obama, right? Paul Graham and other people. When do you remember, or what was it, where you started to think, okay, I think that I'm, I think that I got this?

• 42:08Speaker 00

  After the pandemic.

• 42:09Guy Raz?

  After the pandemic. So 12 years in.

• 42:11Speaker 00

  Yeah, 13, 13.

• 42:14Guy Raz?

  And what was it? What, what was the, was it just an accumulation of things? Or was there, were there moments where a moment, or something, or a conversation where you thought, okay, this is, this is going to change everything?

• 42:27Speaker 00

  It was probably like three things. The first thing was maturity. I was like 38, 39. Like literally, like, I think I grew up with like pretty bad 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, a 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. 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.

• 43:09Speaker 00

  In other words, it was the first moment I had to be a good CEO, and it was a life or death moment. Because 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. The stakes were too high. And I, for better or worse, I'm good in a crisis. I, I realized I could rise to the occasion. So I think it was the stakes, the, 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,

• 43:44Speaker 00

  you know, this whole founder mode, this whole thing of like being in the details, being hands on, that only came from the crisis. 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? Steve Jobs. Around the same time, I met Hiroki Asai, who was this creative director at Apple. I hired Johnny Ive, 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.

• 44:26Speaker 00

  And so I studied, I first studied, how did this guy, 12 weeks from bankruptcy, where it was, take the company out of this tailspin? And basically, what I realized is he got all the details. He cut a bunch of projects. He made a lot of really hard decisions. And the single thing was, he simplified. He was present, leadership was present, not absence. He was 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.

• 45:10Speaker 00

  You know, we had to be very, very hands on. Basically, it was like, we're all in a foxhole. So now I'm running the company hands on for the first time in 15 years. Not telling 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. I'm like, no way.

• 45:28Guy Raz?

  And operating you the way you were meant, you had like?

• 45:32Speaker 00

  Like back off.

• 45:32Guy Raz?

  A bunch?

• 45:33Speaker 00

  Give us space now.

• 45:34Guy Raz?

  And then direct reports, and you got your information.

• 45:36Speaker 00

  Yeah.

• 45:36Guy Raz?

  Because the other things Steve Jobs would do is he would get his information from people.

• 45:40Speaker 00

  Skip level.

• 45:41Guy Raz?

  Right? He had a hun, he would gather 100 people.

• 45:43Speaker 00

  So here's something that a lot of CEOs do. They only talk to their directs.

• 45:48Guy Raz?

  Yeah.

• 45:48Speaker 00

  I don't want to name the person, but I was, I saw an interview of a CEO who appointed as his successor, somebody who failed. And they asked him, how come, you know, did you have a good relationship with him? 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 worked for him. I'm like, really? And now, this is 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 direct, the executive. They might feel threatened.

• 46:28Guy Raz?

  This started during, right after COVID. This is sort of the evolution.

• 46:31Speaker 00

  I pissed off a bunch of execs.

• 46:32Guy Raz?

  Yes. Because you were saying to them, I'm actually going to talk to the people who work for you.

• 46:36Speaker 00

  And they said, you're undermining me, you're going around me, you don't trust me. What are you trying to do?

• 46:41Guy Raz?

  Yeah, not everyone.

• 46:41Speaker 00

  Micro managing. Yeah, micro managing.

• 46:43Guy Raz?

  So what was your response?

• 46:47Speaker 00

  I said, we have to save this company. Because it was a crisis. So I was like, like, it's like, your feelings and your like, like, and how you feel has to come second to us saving this company.

• 46:59Guy Raz?

  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.

• 47:10Speaker 00

  And that was, that's what I did for 10, 12 years. And so I told them, I've tried this for 12 years, and look at where it got us. Look at where it got us.

• 47:16Guy Raz?

  Well, you, I mean, but the company was doing well.

• 47:19Speaker 00

  In 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 joked 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 by, by execution. Guess who won? The company that had great execution, because they compounded. And so we succeeded in spite often of my leadership during those wilderness years. And I said.

• 47:50Guy Raz?

  And that masked, you're saying that the business model that was just, it was lucky, it was really?

• 47:54Speaker 00

  Mass mismanagement, my own mismanagement, and mass 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 want to own it or? I remember saying to this person, it should never be either. That this is not about me just delgating 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 to do. I'm the detail, so I have the information. You see, the board, every board of a public company is an audit committee. The word audit is key, 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.

• 48:35Guy Raz?

  Right.

• 48:37Speaker 00

  AI is the ultimate skip leveling. I can know anything.

• 48:39Guy Raz?

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

• 48:44Speaker 00

  Yeah, to get information.

• 48:45Guy Raz?

  But how do you identify those people in an 8,000-person company?

• 48:50Speaker 00

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

• 49:24Guy Raz?

  They're not gonna wanna work for you.

• 49:25Speaker 00

  Or not gonna wanna work for me. So hopefully, I'm only ruling them like 10% of the time. If I'm overruling them 50% of the time, I'm wrong or have the wrong people. If I'm never overruling them, I'm adding no value. And like, so I should be overruling people only occasionally, because you should be doing things not obvious. And so, basically, to finish answering your question about being the details, I said, you know, you can call 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. 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.

• 50:08Speaker 00

  And I'm gonna tell you an idea, you're gonna tell it back to me. We're gonna partner in 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 have autonomy of the way to do your work, like I won't tell engineer how to code, but you're not gonna have autonomy over what direction to go. Because if everyone has time to go, what direction, then everyone goes in different directions. That's bad. So you'll have empowerment. And then 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 prove anything right away. You want resources, I'll give it to you.

• 50:50Speaker 00

  If somebody's blocking you, somebody illegal is saying you this, I clear the path. I like to joke to people that I'm actually like, like an offensive line. You're the running back, I'm the offensive line, I stand in front and I clear the path for your idea. 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.

• 51:09Guy Raz?

  This whole idea came to light when Paul Graham, his now famous associate, the founder mode. He saw 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. And I, I learned or discovered that that actually wasn't working. 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 pot as possible. How did you convince? I'm sure a lot of people left. I'm sure a lot of your direct reports were like, I don't wanna do this. I don't need this and I wanna work in a more...

• 51:47Speaker 00

  Almost the entire exec team left.

• 51:49Guy Raz?

  Wow.

• 51:49Speaker 00

  Eventually.

• 52:06Guy Raz?

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

• 52:18Speaker 00

  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 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 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.

• 52:50Guy Raz?

  There was a risk it could be wrong, though.

• 52:52Speaker 00

  Yes. Although, the data proved that founders, not all founders become great CEOs, but all the greatest CEOs were founders. From Sam Walton in Walt Disney, to Steve Jobs, to Jeff Bezos, to Larry Ellison. I mean, we could go, we could go down the list, 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 to say, give it a shot. By the way, I said, we did it in pandemic and it worked, so let's keep doing it. I also hired people from Apple. I hired people that worked for founders, is the other thing.

• 53:37Speaker 00

  If you've worked for a founder like Jeff Bezos, I work people that work for Jeff Bezos. I work for people that work for Steve Jobs, they needed no convincing.

• 53:43Guy Raz?

  They understand.

• 53:43Speaker 00

  They already understood. Whereas someone from Procter & Gamble, I didn't hire someone just picking a company, they would not understand, because that founder has been dead for 100 years.

• 53:53Guy Raz?

  So how do you...

• 53:53Speaker 00

  One more detail about being in the details. People probably think I'm in all the details right now, I'm not.

• 53:58Guy Raz?

  Yeah, you can't be. There's too many.

• 54:00Speaker 00

  So here's, here's the analogy. You aren't forever in all the details. That is not sustainable. You, 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 100 first time, it's muscle memory. And then you can let go and you can always, then you can watch them every 10 swings. At some point, it's just muscle memory. I remember the 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, let's just keep doing this until we get to excellence. It was like 70 like versions.

• 54:45Speaker 00

  And everyone was like, oh, we're never ever doing this again. And I said...

• 54:48Guy Raz?

  Was it a press release?

• 54:49Speaker 00

  It was one press release. So it's basically the idea is, if this room's perfect, I'm gonna start by making this glass perfect. Then I'm gonna make this little thing perfect. 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? 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, because there is excellence.

• 55:33Speaker 00

  And they don't understand that the way they got excellence was to be in the details.

• 55:37Guy Raz?

  How do you know? So here, we had Reid Hastings on the show a couple of months ago, maybe a year ago. And you know, they have a famous, Netflix has this famous model, right? About how...

• 55:46Speaker 00

  The call for that.

• 55:47Guy Raz?

  And so, it's sort of a version of a question I asked him, but it 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, although 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.

• 56:27Guy Raz?

  How do you create an environment where people are willing to say, I don't think so?

• 56:34Speaker 00

  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 like CEO whisperers, right? There are, there are some people that are willing, they've been...

• 56:47Guy Raz?

  You have them.

• 56:48Speaker 00

  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. Like co-founders, but also, I have people that have been around for about a decade. Or people that are, I have a few people that, they don't need this job. And literally, so like, they can afford to say, you're wrong. Say whatever and get fired, or not be afraid. So that's the first thing, is that. But I'll give you a trick I do. Not a trick, it isn't a 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 belonging there, and I won't say what it is, we'll unveil it. I came up with a tagline.

• 57:30Speaker 00

  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 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. 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, because it was London, it was last week.

• 58:12Speaker 00

  They came to me, sorry, I said, you have two weeks. They cut the time in half. They said, we're, we're already done 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 what you give permission to disagree is you actually change your mind. You might say, we're doing this, 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. You also have to, 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, oh yeah, it's great. 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.

• 58:57Speaker 00

  Well, maybe their opinion is right answer. So often, you give your opinion less, you have whispers that can tell you the truth. You, you can take the counter position, or you ask people like, what's my blind spot?

• 59:13Guy Raz?

  Like, let's say 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. What happens? What do you do? How do you do it? Do you try to prevent that from happening in the first place?

• 59:28Speaker 00

  Yeah. If a team's working on something for six months and I have to kill it, I feel as a leader that they've gone six months down a journey and haven't pulled the plug. This is why you should be in the details. Because you never, I like to say I want to be the beginning and end of the process. And in the middle, I check in. The reason companies' projects go in the wrong direction is because of one or two reasons. They start wrong, they're not set for success, or they're off an island without oversight. 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 something up for success. Do we have a clear vision of what we're trying to do? Are there the right people working on it?

• 1:00:12Speaker 00

  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 like a whole checklist of things to do. Okay, so at some point, the project's set for success. Now you have to create a rhythm. And the rhythm can be every day, every week, every month, but you have to establish a rhythm.

• 1:00:35Guy Raz?

  So how many projects could do the capacity to be involved with it at any given time?

• 1:00:40Speaker 00

  Couple dozen, maybe 20. But they're all, not 20 a day.

• 1:00:44Guy Raz?

  Yeah.

• 1:00:45Speaker 00

  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. Then other projects I have a weekly or bi-week rhythm. And other projects I have a monthly rhythm. And if I'm not meeting it monthly, then I'm really, I would call myself not involved.

• 1:01:04Guy Raz?

  All right, let me ask you a couple of questions about, specifically about Airbnb and about where it's heading, right? There are a lot of opportunities, right? And the company's core business model remains, right? It's the Kings 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 in Airbnb, I get, and 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.

• 1:01:47Speaker 00

  Yeah, it is.

• 1:01:47Guy Raz?

  They don't own buildings, they don't...

• 1:01:48Speaker 00

  People don't realize this, but Marriott's basically a loyalty program company.

• 1:01:51Guy Raz?

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

• 1:02:10Speaker 00

  Yeah, absolutely. I, there are three things I said I'd never do. The first is I said I'd never do advertising. Somebody once said in the design community, advertising is the price you pay for being unoriginal. 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 example, an exception, but even Apple and Disney and Nike, very inspirational companies have to do advertising.

• 1:02:43Guy Raz?

  You gotta remind people.

• 1:02:44Speaker 00

  I said we'd never do hotels.

• 1:02:46Guy Raz?

  You bought hotels tonight?

• 1:02:48Speaker 00

  We bought hotels tonight. And the reason why is because 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 or 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. BMBs are technically categorized 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 is the, is, well, I really pushed against the loyalty programs. I said, the best loyalty programs, people's loving your product.

• 1:03:25Guy Raz?

  Yeah.

• 1:03:26Speaker 00

  Again, I don't think Disney, Apple, or Nike, these three companies, they're talking about how to have a loyalty program. And I revisited that. So you see there's a pattern here, me saying I'll never do something and then having to become more practical, which is maybe another version of going from a founder or CEO, which is becoming less ideological. You want to have a company that's got a cult-like following, 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, but we aren't gonna do something out of the tube, or me never does. So if we were to do something, it would be very original, very cool, very different.

• 1:04:11Speaker 00

  And, and that's what I can say.

• 1:04:14Guy Raz?

  Okay, I know that you guys are going to, you have an initiative. You're gonna fund a million nights for free for people in distress or, you know, displaced by natural disasters. I think the plan is to put in half a million dollars, I said half a billion dollars...

• 1:04:30Speaker 00

  Yeah, 500 million dollars.

• 1:04:31Guy Raz?

  Into this, because this is part of a nonprofit, Airbnb.org, that actually, I think, started around Hurricane Sandy.

• 1:04:37Speaker 00

  It did.

• 1:04:37Guy Raz?

  Came out of that time. So tell me about, about this.

• 1:04:40Speaker 00

  This is 18 years in the making. In 2008, I emailed my co-founders. The subject line email was Airbnb.org. Airbnb hadn't even launched yet. And we already had the idea for Airbnb.org. And the base, we didn't quite know what it meant, but we kind of thought it was gonna be something around housing. In 2002, nothing happens for four years, because now we got, we got our hands full. 2012, Hurricane Sandy hits. A woman emails us, she said, I want to host one of the disaster evacuaries. I want to host for free. We had to change our system or ladder to do that. That began an effort of whenever there's a disaster, we would try to respond. We couldn't do many. We started responding to disasters. Now, some hosts opened their homes for free. A bunch of people would need to get paid.

• 1:05:23Speaker 00

  So we started raising money or using our own money to pay the hosts, so make sure the guests could stay for free. This happened, disaster after disaster after disaster. Then Afghanistan, tens of thousands of refugees needed housing. We housed 20,000 Afghan refugees. Russia 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.

• 1:06:07Speaker 00

  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 because they couldn't afford to stay overnight in New York, because of how expensive hotels were. My mom had an idea, you should provide medical stays, free stays for people getting medical treatment. So we eventually did that. And now we have medical stay treatment. So if you want to 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 a hospital and their parents aren't there. But we can put them in a house for free, near the hospital, and they can visit the

• 1:06:52Speaker 00

  child every day. And this obviously is really good for the child, but also really good for the parents. Domestic violence victims. What happens when you're a victim of death of violence? Where do you go? Shelter? That's not a very good living condition. What if you could be at home where our 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

• 1:07:37Speaker 00

  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? He said, I think in a few years, we could, we could house a million nights with the free housing, which would probably make us the largest organization in the world that provides free housing, bigger than Ronald McDonald House, which has gone on for like 40 or 50 years, bigger, I think, than any government. I said, well, what would that cost? It turned out it 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, initiative to shareholders? And I think we ultimately came to the conclusion that we're gonna do it.

• 1:08:19Speaker 00

  And I think it's good business to do good in the world, and I think that 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 a company ends up doing in its, in its lifetime.

• 1:08:35Guy Raz?

  Normally, I ask our founders 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? And, and he, you know, what would you do if you weren't working? And he answered the question three different times, started and stopped and started and stopped. Because I think it was a tough thing for him to think about back then. Obviously, he's moved on, he's still involved, is on the board. You're 45, I think, now, right? I mean, you've been doing this for a long time. You've had incredible professional success.

• 1:09:19Guy Raz?

  Can you, could you imagine 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?

• 1:09:43Speaker 00

  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, 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 surrounded by family, feeling he was most important, but he still cared about Apple. Leonardo da Vinci carried the Mona Lisa with him till he died.

• 1:10:27Speaker 00

  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 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 here. 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 we would, I hope I'd still be doing this because my heroes were doing it and I just love it.

• 1:11:10Speaker 00

  And I know, I know parents, my friends' parents, where some of them retired and some didn't. The ones that retired got older a lot faster than the ones that didn't. And so whether I'm doing this or not, I'm always going to be creating. I'm always going to 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 because I love it. It's because like, I have one of the largest canvases any artist or designer's ever been given in human history. And 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, that idea, people, what was luck was getting the shot.

• 1:11:54Speaker 00

  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 them in the door, in the club, I don't want to 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 want to live in that world is, or they want to 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.

• 1:12:37Speaker 00

  But I think I'm going to be doing this for a long time, you know? And, you know, one of my other heroes is Pablo Picasso, or at least he had a lot of good quotes, Pablo Picasso, by the way, painted till the end of his life. He had so many great quotes, but he said, "All children are born artists. The problem is remain an artist as one grows up." He also said, "It took me four years to paint like Raphael, but the lifetime to learn to paint like a child." I want to stay young the rest of my life. And the thing is, therefore, I want to have a childlike, not childish, but childlike quality. I want to remain an explorer. I want to learn. I want to grow. I want to keep making, every year of my life, I want to make at least one new friend. I want to keep creating till the end of my life. I want to keep connecting and helping people till the end of my life.

• 1:13:22Speaker 00

  I don't know how long that is, but I just want to just keep creating, keep painting on this giant canvas I've been given. And so long as I have this canvas, I'm not going to stop painting. Thank you. Thank you.

• 1:13:45Guy Raz?

  That's Brian Chesky, co-founder and CEO of Airbnb. By the way, if you haven't heard our original Airbnb episode with this co-founder, Joe Gebbia, who after finding out about his Italian roots now pronounces his name Gebbia, not Gebbia, or even if you have heard that episode, it's worth going back to. You'll find a link to it in the episode description. Just scroll down. And some exciting news. You can now watch How I Built This on YouTube. This conversation with Brian is the very first episode on our brand new channel. Just search How I Built This on YouTube and subscribe. We'll also put a link to our new YouTube channel in the episode description, so please check it out. Our show is produced by Podcast Point Man.

• 1:14:29Guy Raz?

  I'm Guy Raz and you've been listening to How I Built This.