Brian Chesky ON: The Crisis of Disconnection and Loneliness & How to Tap Into Your Creative Potential

How far are you willing to go to pursue your passion and achieve success? Do you sometimes find yourself sitting in silence and getting in your own thoughts? When we're driven by our passion, we become creative, motivated, and enduring every hardship that comes our way. Today, Airbnb Co-founder and Chief Executive Officer Brian Chesky sits down with Jay for an honest and eye-opening conversation about the other side of success. Brian talks about how crucial it is to choose your group wisely for the people you surround yourself with can make a big difference, sharing success with others keeps you from feeling all alone in your victories, and the need for balance between focusing on your goals and creating a community where you can thrive. Mental health is another important point of discussion as well as the outdated perceptions we have of ourselves that potentially blocks personal growth. In this interview, you'll learn: How to be wise in choosing your people How to keep valuable friendships How to deal with success How to overcome loneliness How to be of service to others How creativity can solve problems Join us in this engaging conversation as we navigate the twists and turns, seeking wisdom and connection for personal growth. With Love and Gratitude, Jay Shetty What We Discuss: 00:00 Intro 02:16 Choose the people you want to surround yourself with 05:33 Going in a journey that will help you learn something new about yourself 08:47 Never allow arguments to win over your friendships 13:28 Share your success or else it might feel so isolating 18:24 To truly understand someone is to try to walk in their shoes 20:35 That feeling where you don’t fit in anywhere 28:29 Loneliness has led to a lot of mental health issues 34:59 Worry less about what people think, focus on what you can share with others 39:42 There are two words that define being alone - loneliness and solitude 41:40 Creativity is about bringing different experiences together 49:00 Try more things, have more experiences, and avoid seeking status 50:41 What would your younger self tell you now? 55:37 We are who we think other people think we are 57:48 The tendency to make an outdated perception of ourselves 01:00:32 How do you want to be remembered? 01:03:15 Singular focus is good for success but it has limitations 01:09:03 What keeps you up at night? 01:14:19 How do you process your thoughts and ideas? 01:17:38 Finding a shared value and having clarity about what you want to do 01:20:13 Losing yourself while pursuing your passion 01:24:00 How do you want to define family? 01:27:47 The wisdom of older people and the curiosity of a child 01:32:16 Even though things are interconnected, it doesn’t mean they’re all the same 01:36:12 Brian on Final Five Episode Resources: Brian Chesky | Instagram Airbnb See omnystudio.com/listener for privacy information. 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.

• 0:00Jay Shetty?

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• 0:44Jay Shetty?

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• 1:30Jay Shetty?

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• 2:12Jay Shetty?

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• 2:25Brian Chesky?

  He said something to me, he said, Brian, do you know what the number one killer in America is? I don't know, is it like heart disease, is it cancer? And he goes, no, the number one killer in America is loneliness.

• 2:33Speaker 02

  Airbnb CEO, his name is Brian Chesky. He's a badass in this business. You're worth thirty billion dollars.

• 2:39Brian Chesky?

  The problem with success is it tends to amplify things. No one ever told me how lonely you would get. It's almost like I had to go on this entire journey to realize I had everything I needed before I even started the journey. If I die, will I die Brian Chesky or the Airbnb guy just died?

• 2:53Jay Shetty?

  This is without a doubt the most unique episode of On Purpose I think we've ever had. Before we jump into this episode, I'd like to invite you to join this community to hear more interviews that will help you become happier, healthier, and more healed. All I want you to do is click on the subscribe button. I love your support. It's incredible to see all your comments and we're just getting started. I can't wait to go on this journey with you. Thank you so much for subscribing. It means the world to me.

• 3:19Speaker 02

  The bestselling author and host.

• 3:21Speaker 03

  The number one health and wellness podcast.

• 3:23Speaker 02

  On Purpose with Jay Shetty.

• 3:27Jay Shetty?

  Hey everyone, welcome back to On Purpose, the number one health and wellness podcast in the world, thanks to each and every one of you that come back every week to become happier, healthier, and more healed. And you know, that's my goal here, to create a community where we can all come together, feel connected by ideas and visions and thoughts that help us in our daily lives. And today's guest is someone who's achieved incredible success, but also someone who I believe is carrying ideas and insights that can be really useful to us on our journey to whatever success may mean to you. I'm talking about the one and only Brian Chesky, who's the co-founder and chief executive officer of Airbnb.

• 4:08Jay Shetty?

  In 2007, Brian and Joe Gabia became Airbnb's first hosts. Since then, Brian has overseen Airbnb's growth to become a community of over four million hosts who have welcomed more than one billion guests across 200-plus countries and regions. Brian is a signatory to the giving pledge. And is committed to donating the net proceeds of his CEO equity compensation to community, philanthropic and charitable causes, something that I'm so passionate about and so excited to dive into. Brian, welcome to On Purpose.

• 4:40Brian Chesky?

  Well, thank you for having me. Really excited to be here. This is awesome.

• 4:43Jay Shetty?

  I'm truly honored. I think there's very few, as I was just saying to you offline, and I want to repeat what I said. I think it's hard to build something that matters. It's hard to scale something that matters. And it's hard to build and scale something that matters and keep making it matter. And you seem to be doing all those things.

• 5:02Brian Chesky?

  We try every day.

• 5:03Jay Shetty?

  Congratulations. It's been a joy watching it from afar. And I'm excited to build this relationship with you.

• 5:08Brian Chesky?

  I'm excited to talk about this.

• 5:09Jay Shetty?

  Yeah. Well, let's dive into it. I want to start off with my first question, which is,

• 5:14Jay Shetty?

  what makes you happy today? And how does it differ from what made you happy 16 years ago?

• 5:20Brian Chesky?

  I think that I'll start with what I thought would make me happy. And I'll tell you what does make me happy and how they're different. When I started this company like 15 years ago, I started my co-founders. I was totally broke. I had no status, had no power, no money, nothing. And I felt like what would make me happy was climbing a mountain and becoming incredibly successful. And the challenge is that, well, what do you do when you get the top of the mountain? You've achieved it. And what I've realized is, at this point, like I'm 41 years old. And a lot of people ask me like, why don't you just retire? Like, why don't you,

• 6:01Brian Chesky?

  or why don't you do it all over again? And for me, I would tell them because the fun is just starting. But the fun of just starting isn't to like, get the next billion people. I kind of think of myself maybe more than a business person. You know, you're kind of who you are growing up. And I was a designer growing up. And I kind of think of Airbnb as like, one of the world's biggest canvas. Almost never has a designer been given so much responsibility, so much opportunity. And what I love is, you know, like a musician wants to play music, a painter wants to paint, a builder wants to build, a climber wants to climb.

• 6:45Brian Chesky?

  And as an entrepreneur, I want to create and connect things and, um, and try to like defy the notion of what a business person could be or what a designer could be. Because I never met someone like me growing up. And I'm not saying anyone's going to try to be like me. But if I can remind people that there's, leadership comes in many different faces, many different flavors, and that a creative person, you know, can run a company and can run a really big company, a Fortune 500 company, then that's, that's the very beginning. And I, I feel like what makes me happy now is working with people I love. Like the, one of the great things about success is you can choose the people you surround yourself with.

• 7:29Brian Chesky?

  And I get to like work every single day with people I love on ideas that I'm obsessed over. And I'm just so obsessed, like I think my motivation's changed. I think when I started, my motivation was about myself becoming something. And once you achieve that, your motivation often turns outward. It's about, it's starting to be about giving to other people, to letting them experience a small part of what I was able to experience. And it becomes just about the work. See, when you're not successful, you get validation when people praise you. But eventually, like you do it for yourself, that you're not doing it for status or success. Because at some point, you've gotten all of it.

• 8:13Brian Chesky?

  Like how much more is going to make you happy? And so just doing things I love, of people I care about, that's what makes me happy today.

• 8:20Jay Shetty?

  That's beautiful. That's, I, I can see that it's true for you too. I, I can see that it, it's, it's real for you as you're saying it, which is such a special place to be. And it was interesting when you were talking about this idea of climbing a mountain. I've often thought that There's one journey in life that we take that's upwards, up a mountain. And then there's another journey we all have to take that's inwards to the valley. And that's a journey that not everyone gets to take or everyone thinks about taking because we're so busy trying to get up that we don't often get to go in.

• 8:54Brian Chesky?

  Right.

• 8:55Jay Shetty?

  And it sounds like you've been excavating that internal part for some time.

• 9:00Brian Chesky?

  You can learn a lot about yourself through this journey. And you're right, the biggest journey I've probably embarked on is the one inside of myself. The brightest days of my life and the darkest days of my life have been in the last 15 years. The highs are incredibly high, the lows can be incredibly low. The amount of stress can be unrelenting. The rewards are like hard to even grapple with. When you go on a journey like this, you learn a lot about yourself. And you start to also learn like what's important to you. Starting a company, you know, one of my first investors said, Brian, starting a company is like jumping off a cliff and assembling the airplane on the way down. Maybe another way of saying it is like playing a video game.

• 9:45Brian Chesky?

  And it's like a thousand levels. And each level gets harder. In each level, you learn something about yourself. You do something that's uncomfortable. In each step of the game, you learn something. And the problem with success is it tends to amplify things. I mean, that can be good, but it all can still can amplify holes you have in yourself. People that are a little bit paranoid get very paranoid. People that are a little deceitful become like completely fraudulent liars. People that are a little narcissistic become like egomaniacs and stuff. And so the stuff can tend to amplify tendencies inside of yourself. And so if you're afraid of conflict, that's going to actually manifest in like not actually dealing with things.

• 10:28Brian Chesky?

  If you can't, if you're not decisive, there's going to be an element of bureaucracy. If you're like get overwhelmed and you get paralyzed, there's going to be an action in the company. And so you learn so much about yourself. And I, through this process, I probably have learned more about myself than I even have about business. And it's been an incredible journey. And yeah, it's like incredible lessons. And the company is like a mirror about you, right? Like when you see a company, it's like a walk in your house. And by walking your house, I can step a little bit in your mind. Because the house, you bought the house, you furnished the house, you made a thousand decisions. And it would take a while for me in conversation to understand you, but I walk in this house and I can understand the thousand decisions you made.

• 11:12Brian Chesky?

  A company is like that, but it's like a hundred thousand decisions or a million decisions. And so by seeing the company, you can like see into the person's mind, everything they do. And not even everything they do, but everyone they surround themselves with and the culture they create. And what they, and that's the thing that's so crazy.

• 11:29Jay Shetty?

  I'm intrigued. You said something there that really stood out to me. You said that the happiest thing and the best thing about being successful is that you get to choose the people you worked with. You obviously built this with friends.

• 11:40Brian Chesky?

  Yeah.

• 11:40Jay Shetty?

  And that's how it started. It started in a place of being around people you love with. What was the biggest point of challenge in building something with people you love as you grow it? And what is it that you experienced? And what was the biggest lesson that you took away that actually kept it going? Because I can imagine as you're describing highs and lows, all of this changed for 16 years. But here you are, still building it together.

• 12:06Brian Chesky?

  Think about how many stories you've heard of founders. It's like a band. They come together and then eventually the band breaks up. And people don't stay together. They resent each other. Maybe things end very ugly. It's like a band, except like it's become so much bigger than the band because it's not just the three of you. Imagine a band that starts with three people and ends as 3,000 people. And that amount of pressure, the amount of spotlight, the money, the changes in like people's status and positioning. It can do a lot to break people up. But also unlike a band where maybe, not to say you just have to agree on like where you perform and what you sing. With a company, you have to agree on like who we're going to hire, what we're going to call, what markets we're going to go into. What's the prioritization, like who are we going to raise money for?

• 12:50Brian Chesky?

  I can go down the list of like the thousands of things you have to agree to. And With Joe, Nate and I, I often say it's really good to start a company with friends. Not everyone has friends to start a company with, but you want that reservoir of goodwill. And we made a decision. The decision was that no one decision is going to supersede our friendship and our relationship. That we're never going to have, we'll debate, we'll argue, but we'll never allow a situation where winning an argument is the most important thing. Because if you think about a company as 100,000 decisions, it could also be 100,000 arguments. And if you get stuck on the first debate, or you like, somebody won the debate, okay, great, you have 99,999 more things to discuss.

• 13:34Brian Chesky?

  And so, the lesson I learned is, I mean, first of all, Jay, I was lucky. And a lot of people, when I say I was lucky, they think, oh, you were at the right place, the right time, with the right idea. And I said, well, maybe. But there's something I was much luckier about. And what I was most lucky about, what made me most fortunate was I met Joe and Nate. That we had this unbelievable chemistry. One time, we had to do like some personality tests. It was like one of those core wheels. And we took this like personality test to see about our chemistry. And they plotted our like personalities, and they formed a perfect equilateral triangle. Not always you're going to find people that are perfect complements to you. I'd say a couple of things. Number one, you want to have a team with people that you are friends with, or could

• 14:18Brian Chesky?

  see yourself becoming friends with, that you have a deep love and respect for, that you're going to probably spend more time with your co-founders than your spouse or your family, if it goes well. If it doesn't go well, then maybe not. But that's the best case scenario. That people that have shared values. Because you can debate anything, so long as you're trying to climb the same mountain and the same belief system. If you have different values, eventually those are going to become irreconcilable conflicts. But you probably also want complementary skills. The worst case is people with different values and same skills. Right? We do the same job, we step in each other's toes, and we're trying to go in a different direction. And so, I think, and then I think the final thing is just this mutual love and respect, and never losing sight. You know, one of the things I tried to make sure of is like, even as CEO, I wanted to try to make sure that like,

• 15:03Brian Chesky?

  Joe and Nate, you know, were included in things and we, I wanted to always make sure that people referred to us together. We thought of us as a, as a, as a unit. When we, when I like, when in public, you write a founder's letter and a lot of people write letter and they just sign the name of the CEO. I made sure that it was from all of us and was representing all of us. I feel like they are the heart and the soul of the company. And it's like, you know, parents, like, you know, not every child has the fortune to have multiple parents. Not every company has the fortune to have multiple founders, but if they're together, they're not fighting, they have a mutual love and respect for one another, that's going to permeate the company, just like it permeates the health of a child. And Joe and Nate and I kind of thought of ourselves as parents of the company as a child. I'd never have

• 15:47Brian Chesky?

  had kids, but you know, there's something about that. And I think who you are and that relationship permeates every single thing. If the founders fight, the employees fight. If they have respect for one another, that is going to be a role, a model that other people throughout the organization are going to copy. And that's what I've learned from that.

• 16:05Jay Shetty?

  I think, I think what you're saying is very, very true. And it's remarkable that you've been able to hold on to that. I mean, I remember just comparing it to something very miniscule, but I think a lot of people will be able to relate to. It's like, I think with your bros at college or at school, you'd always be like, we're not going to fight over girls, but we're not going to fight over women. And then there'd always be the guy who, who trades the friendship for, for a girl. And then like the whole thing's lost.

• 16:26Brian Chesky?

  And that's a short-term decision.

• 16:27Jay Shetty?

  Yeah.

• 16:27Brian Chesky?

  And, and I understand why people make short-term decisions. They make trade-offs. They want to win. But as long as you think about the arc of your life and that life is only like who you're with and that you don't want to be alone at the end of your life, and you certainly don't want to be alone at the end of a journey. If I'm climbing a mountain, I want friends by my side that can like provide supplies at me and like, you know, like being the only one in power is actually quite lonely. Having been in that little bit of that position, I've now can tell people that you want to share it because otherwise it's incredibly isolating and lonely. And you know, like, if you get all the credit, you could also get all the blame and it can be very difficult to, and so be able to share that with Joe and Nate. And now to be able to share that with the people that I get

• 17:09Brian Chesky?

  to pick to surround myself with. That, I mean, that is one of the most fulfilling things. And, you know, great relationships get better with age and they give you energy. They make you better. They hold your negative tendencies in check and they pull out like creative ambitions in you. They see potential in you that maybe you don't see in yourself. I did never imagined that I could be CEO of any company. I didn't think I could be CEO of a pizza shop, let alone be CEO of like a giant Fortune 500 company that over $60 billion last year in bookings. Like, that's completely crazy. And I've learned a lot of lessons from this journey. One is I think we all were born with like unknown potential.

• 17:54Brian Chesky?

  And I think the other thing is sometimes the best people in your life will be people who see potential in you that you didn't see in yourself. And I often wonder like, why did Joe and Nate even agree to like, let me be the CEO? Why did Joe tell me one day in 2007 to pack everything in the back of an old Honda Civic and drive up to San Francisco? Why did he think that was a good idea? And years later, he's told me. And he told me that we went to college together at RISD and he saw something in me. And it's possible he saw something in me that I didn't even yet see in myself. And this is like the hero's journey. Somebody might believe in you. They might see something in you.

• 18:39Brian Chesky?

  And that's what I got with Joe and Nate. And I think I believed in what I think I saw. They saw potential in me. What I saw maybe was potential in this idea. That if people could experience what we experienced that first weekend, when we host three guests, that this would be an idea that would spread around the world. I think we have an easier time imagining living like this on Mars and living differently on this planet. But which of those two do you think is more likely to happen in the near term? It's really hard for us to imagine sociological changes. We can all imagine technological changes. We can imagine things getting bigger, faster, but it's hard to imagine us living differently. And I don't think that we were visionaries per se.

• 19:24Brian Chesky?

  I think we were expeditionaries. And I think we discovered something. One of my first investors, Paul Graham, he said, what do you know? What, what unique knowledge do you know that has allowed you, afforded you the ability to start this company that no one else has? What do you know that no one else understands? And I think That we discovered something. We discovered that like, people are fundamentally good. You know, you read the newspaper. I think Chief Justice Earl Warren said, I don't turn to the front page of the newspaper. It's filled with man's failures. I go to the sports page. It's filled with man's successes. I think we live in an abundance of data reinforcing that people aren't good. And we have probably as much data as almost anyone, because in

• 20:08Brian Chesky?

  the last 15 years, one and a half billion people have used Airbnb, one and a half billion guest arrivals, in nearly every country in the world, more countries, I think, than Coca-Cola, nearly the population of L.A. every night living together. And it's only reinforced what I think we naively believed in the beginning, these two simple ideas, that people are basically good, they're 99% the same. I think that Joe and Nate believed in me and my potential to be in this company. I think we collectively believed in the potential of each other. And I think also that this idea would be one that could spread around the world if only we could figure out how to communicate it to people.

• 20:51Jay Shetty?

  How special. I mean, that's, that is something that I definitely got a mini version experience of. I just finished Forty City World Tour.

• 21:00Brian Chesky?

  Really?

• 21:01Jay Shetty?

  For my second book. And we probably met about 100,000 people on the way.

• 21:06Brian Chesky?

  Oh, my God.

• 21:07Jay Shetty?

  And much, much smaller than the 1 billion bookings. But I would agree with those two sentiments so strongly, that we're 99% the same, and people are overall good.

• 21:21Brian Chesky?

  If people believed everyone was basically the same, then how could you hate someone else? Because to hate someone else is to hate yourself. And I think that we spend a lot of energy in society celebrating the 0.1% that makes us different. I think there's a good part of that. We call that diversity and heritage and culture. But there's a dark side of believing that we're like, all very different. And that's, that we believe that people are the other, and that therefore, it's harder to have empathy with somebody who isn't us. And I think that the best way to understand That somebody is similar to you is to walk in their shoes and to like just, you know, there's an old saying, it's hard to hate someone up close. And I think there's something weird that's happening where the more digitally connected we seem to get, the more, the less physically connected we sometimes get.

• 22:04Brian Chesky?

  And I wonder if that has a way of like confusing us about people that we might argue about on the internet. No one else, no one's ever changed the most mind in YouTube comment section. But if it's hard to live with somebody or to walk in the shoes and not change your mind, how, how could you not change your mind about something? Cause that would suggest that like you've experienced all of life up to that point and that you feel your opinions are fully formed and that no new data could ever change your mind about anything. How could that pass? How'd you even have your opinions in the first place? Based on probably experiences. And so how could you not change your experience, your opinion by new experiences with new people? And that's kind of the, kind of the simple way we think about it.

• 22:45Jay Shetty?

  Yeah, I'm so glad you raised this idea of, you talked about the incredible friendship that you have with your co-founders. But at the same time, you brought up this idea of loneliness and you said, you never want to be lonely at the end of a journey. You never want to be lonely at the end of building something big. And I think in the world today, we are seeing loneliness proliferate. And it's the loneliness of not, that we're not around people. It's not loneliness that we're not surrounded by people. It's that we're surrounded by people, but we don't feel understood. We don't feel seen. We don't feel heard, that we feel that we have to be someone apart from ourselves, even around the people that we're closest to. And so the idea of loneliness is expanding away. People are feeling disconnected from each other.

• 23:27Jay Shetty?

  Yet you're talking about 16 years ago, you and a bunch of friends feeling so close to each other. When have you felt lonely in your life? And what have been your next thoughts and steps that you've taken from that point?

• 23:42Brian Chesky?

  I think loneliness, which is like the darkness or the absence of connection. And love and connection have in hindsight been some of the driving forces in my entire life.

• 23:57Brian Chesky?

  If I were to think about my journey with loneliness, I think I grew up as a little bit of a lonely, isolated kid. I was interested in art and design, but I also played sports. I didn't really feel like I fit in growing up. I kind of felt like an outsider. I went to the Rhode Island School of Design, where a lot of people who felt that way would come together. But even at RISD, I didn't feel like I fit in there.

• 24:23Jay Shetty?

  Even as a hockey player?

• 24:24Brian Chesky?

  Even as a hockey player at an art school, like, kind of like, I went to like a military, like, private school. And then I went to art college. And like, I kind of had a foot in each and not fully like, like, and I had, you know, maybe issues of authority. I didn't really fit in. It turned out to be a huge benefit to being a tech founder. But of course, who doesn't want to fit in it growing up? Like, so much of our desire is to belong. Because I think to belong is a deeply human trait. You know, we're tribal. We grew up to be in tribes of like fifty, hundred, hundred fifty people. And to not be part of the tribe and not belong in a prior era would be a death sentence. And I think that ultimately today, we're probably living in one of the loneliest times in human history.

• 25:08Brian Chesky?

  If people were as lonely in yesteryear as they are today, they'd probably perish. Because like, you just couldn't survive without your tribe. And I think that, you know, for me, I didn't realize that this was a thing that I've been, I was fighting throughout my life. And so when I was twenty five, twenty, turning twenty six, I started with my two co-founders. And we became the family. We became a family that hadn't had for ten years, since I really, ten years since I left the house. And then suddenly, we were a family, the three of us. And we're just hanging out together. We live together. We all like, wake up, woke up around the same time, around eight AM. We'd work till midnight. And then we'd do it the whole, the next day, we'd go grocery shopping together. We'd like, go to the gym together, it was very communal. Then we hired people that were basically our friends.

• 25:52Brian Chesky?

  We wouldn't hire anyone we didn't like. And then we didn't have a lot of work-life, like, boundaries. Everyone was young. We were, we didn't have families. We'd go out, like, drinking together and hang out together and dinner. And that became like a family. It became like a community. And that was incredible. And it was this deep, rich connection. And those were some of the closest friendships I ever had. But then something happens. We go on a rocket ship. And then I go from being a founder to a CEO. And I was one of three founders. And then I became one CEO, an individual role. And as I became a CEO, I started leading from the front at the top of the mountain. But then, you know, the higher you get to the peak, the fewer the people there are with you.

• 26:36Brian Chesky?

  And no one ever told me how lonely you would get. And I wasn't prepared for that. And I had this guilt about not working because so much of my life was about being successful. Probably, probably if I were to dig deep, because I thought that would make people love me. And that was probably adulation, but I probably didn't know it back then. And I probably thought that by being successful, I'd feel really different. And I remember I got to this point where I was already feeling pretty isolated. And then the pandemic happened and I'm living by myself in a house. And I'm finding myself on Zooms 24/7, like 16, 18 hours a day for an entire year of 2020. I, you know, help with a team.

• 27:20Brian Chesky?

  We navigate out of a crisis. People were predicting we'd like, some people were that we would go out of business. We stared into the abyss and we like got in a foxhole. We turned the company around. We took it public and the day of our IPO, we reached a hundred billion dollar valuation. And remember, if you told me like a million dollars is more money I ever imagined growing up. My parents are social workers. That was like an unfathomable amount of money. And I remember after going public is like, oh my God, there's this like amazing exaltation. It was amazing. Like I'd gotten to the mountain and then I wake up the next day and my life is exactly the same. I'm alone. I wake up, I put on sweatpants, I go on to IMAC and I have like 10, 12 hours of Zoom meetings.

• 28:04Brian Chesky?

  And I just don't really have much of my like life outside of work. My work was my life. And then I remember having a 40th birthday party and I had to make a list of people to invite. And never in my life have I tried to like make a list of who my friends are. But when you have to make invitations, you have to make a list. And I made a long list of people. And then I kind of went down the list and I said, when's the last time I talked to these people? And I realized that almost every single person in the list, if I were to ping, I'd have to catch them up in my life. I couldn't just dive into something because I had not maintained those relationships. And it was just something that like started, you know, and I started noticing I started feeling more isolated.

• 28:48Brian Chesky?

  I would have more negative ruminations and stuff. And I didn't know at the time that I was lonely. I knew I was isolated, but I didn't know that that also meant loneliness. And I thought, I have all these people around me. How could I possibly feel this way? And there were a couple of people that like entered my life that like gave me some awareness and consciousness. One at a deeply personal level and one more at the professional level. At the personal level, I ended up actually becoming friends and a person who became a mentor to mine was the former President of the United States, Barack Obama. And it was like a kind of a crazy story where I, you know, I like many people met him in the White House.

• 29:29Brian Chesky?

  And then he, we keep in touch after the White House and he became a bit of a mentor to me. We developed a relationship and initially it was a purely professional relationship. But by 2021, after we went public, he kind of told me, like, I kind of told him what I was feeling. And I, he said, I think you're kind of lonely and you probably need to renew friendships. And he described that he had like these 10 or 15 friends. Most of them, he was friends with before his presidency and they kept him grounded and rooted. And your roots come from your past and your past is often your relationships. Because I kept asking him like, how didn't you like lose your mind? He's like, it's hard to lose your mind when you have deep connections and relationships to others. And this is around the time I was like totally realized I hadn't maintained relationships.

• 30:12Brian Chesky?

  So one of the most important things I decided to do was renew the relationships that were in that invite list, those people that I hadn't really kept in touch with. And so I rekindled relationships with my college friends and I committed that we'd take like one or two trips a year because the problem is if you don't see your friends, you only text them, the only things you can talk about are like the same old stories from 20 years ago, or you can talk about other things in your life, but you have no shared experience. And Zoom and phone calls and text messages are not shared experiences. You can only talk about an experience you had. And so I did that with my college friends. I did it with my high school friends. I started spending more time with my sister and other people in my life. I ended up getting like a dog, a golden retriever named Sophie Supernova.

• 30:54Brian Chesky?

  And the crazy thing, Jay, is I can tell you, like the ride of Airbnb and having all the success and money and power and all this stuff, it can be amazing. I'm not saying it's not amazing, but I actually think I probably, it's almost like I had to go on this entire journey to realize I had everything I needed before I even started the journey. That the thing that probably gave me the greatest life satisfaction was a thing that I didn't even need money for and I didn't even need to have success to achieve. Relationships, many of them I had before I started.

• 31:26Jay Shetty?

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• 32:10Jay Shetty?

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• 32:52Brian Chesky?

  Well, I think you had Robert Waldinger on your show and, you know, he, I actually met him last week for the first time. He is, as people listening are probably realize, he was a Harvard professor who's run the longest study on human happiness. It started before he was even alive. It's an 85 year study and the question was, what's the secret to happiness? And of course, I don't think they thought there was a silver bullet answer and of course it is and it's relationships. And I think that that's what I've learned, that like, as I've reconnected, I've felt like this light and this love permeate me and I think it's made me a better leader. Cause one of the things Robert told me is 50% of CEOs are lonely. Now, somebody listening say, oh, poor CEOs. Well, I would say, I don't think I want society to be led by a bunch of lonely people.

• 33:37Jay Shetty?

  Exactly.

• 33:38Brian Chesky?

  I don't want society to be led by a bunch of lonely people because lonely people are less trusting of other people, they're more paranoid, they're less resilient, they will typically have less empathy because they will push people away. I don't think they're as connected, they make worse decisions. And so, we do not live in a world where people are lonely and we especially don't want to live in a world where leaders are lonely. And so, this has been one of the defining things in my life. So, I think the first part of the answer is for me to deal with my own sense of isolation and loneliness. And again, Jay, I thought loneliness was something that like, people's grandparents experienced in their life. I didn't think it was something the young person experiences. And the other person I met is the now and former surgeon general of the United States

• 34:23Brian Chesky?

  with Dr. Beck Murthy. We hired him during the pandemic because a lot of people were afraid to like, you know, go into Airbnbs and they were worried about like germs on surfaces. And so, we hired him to do this like, you know, basically create cleaning and sanitation protocols. But I remember having a conversation with him. And he said something to me, he said, Brian, do you know what the number one killer in America is? I'm kind of paraphrasing the conversation and I said, I don't know, is it like heart disease? Is it cancer? And he goes, no, the number one killer in America is loneliness. And I said, loneliness? What are you talking about? And he said, yeah, being chronically lonely is worse for your health than smoking a pack of cigarettes a day. And it can take 15 years off your life.

• 35:04Brian Chesky?

  And not only that, but about half of Americans are lonely. Two out of three teenagers by some studies are lonely. And it's not just that they're lonely. It's that this is leading to a lot of mental health issues. You know, one in four teenagers have suicidal ideations. You know, that's not just teenagers. You see like, you know, like there's a crisis with men and boys. There's a crisis with like one in three seniors are lonely. This is like, so I started realizing this is like a really big crisis. It's, it may be a way to say it's a crisis of disconnection. And I started realizing like, you know, global warming, maybe you could say that's disconnection with the earth. And that loneliness is disconnection from each other.

• 35:45Brian Chesky?

  And maybe loneliness at the most fundamental level starts with disconnection from yourself, that you're running away from something. And that sometimes trying to be successful and climbing a mountain is running away from something. You know, because you think that what you are isn't enough. And if you become more, you'll be, you'll become something. And that is the problem because of course, we never fully leave our history and our psychology. And so then I started learning about loneliness at the intellectual level. I started asking, well, Airbnb is a global community. We have hundreds of millions of people. Some of the best ways to connect with other people are through travel. I was using travel and Airbnb to like, connect with my friends because most of them didn't even live in the same city as me.

• 36:27Brian Chesky?

  I started realizing, you know, you get to my age, you're 41, you have a public company, you have a couple of choices. You can just stop and say like retire. You can do something new or you can just say, my work is just getting started. And for me, like, I want to, of course, I want to like, keep getting a return for shareholders and make sure like, if people give me money, they feel like it was a good decision. If employees put their trust in me, it was a good career decision. And, and I, I want all that to happen, but. That can't be enough, that there's got to be something more. The artist in me, the designer in me, wants to solve a problem. The problem can't just be a stock price. It's got to be something greater. And I have like the, one of the biggest canvases in the world of any designer ever. And what I'm gonna design is not products, I'm gonna design connections between people.

• 37:12Brian Chesky?

  And so I started learning about loneliness. I started realizing that modern life seems to be making people lonely. And there's all sorts of theories. Maybe it's that like, you know, everything is digitized now. The mall is now Amazon, the theater is now Netflix, the grocery store is now Instacart. The office is now Zoom. And I'm a proponent of all these things. I use all these services and I love them. But, you know, the problem is, it's like ingredients. We evolved, I think, to be in physical proximity with one another. And as we spend more time online, we seem to be spending less time together. And I think we have to be very, very careful as a society, what kind of future we want to design for ourselves.

• 37:52Brian Chesky?

  So I guess for me, loneliness and its solution, which is reconnection, has been both a personal mission and now a bit of a professional mission. And a product or a service can't help with that, but a community can. And if Airbnb can go from a travel service to a travel community, if we can be in the business of trust, where you understand one another, and we can help you connect with people in your life or meet other people, that to me would be where the next chapter is. And there's something about like solving your own problem, then wanting to like, you know, trying to spread it to others is, I think, one of the most fulfilling things.

• 38:34Brian Chesky?

  They always say, the best way to start a business is solve your own problem. And I think that's what I've been trying to do.

• 38:39Jay Shetty?

  Thank you for coming to my TED Talk. That was like, that was a, that was a masterclass on loneliness. And I, and I mean that. And it's beautiful to see how it can so deeply correlate with what you've already built. And I think that's what, as I'm watching you and as people are listening and watching, I want you to take this away that You're not neglecting or negating any experience you've had. You're actually collecting.

• 39:05Brian Chesky?

  They're awesome.

• 39:05Jay Shetty?

  And bringing them all together and saying, look, actually, it's additive. I think a lot of us have this tendency in the material world to build something, go, ah, it wasn't it. Throw it away and then go try and build something else. And actually, what you're saying, actually, I built this thing. It's great, but actually it could be so much better and it's just the beginning.

• 39:22Brian Chesky?

  Exactly. And I also think that like, I'm not saying it never would have mattered and don't try to be a tech founder and don't try to achieve success. I'm just saying they're ingredients.

• 39:31Jay Shetty?

  Yes.

• 39:31Brian Chesky?

  And that if you do it alone and you don't have relationships and you do something to fill something in you, it's not going to fully do that. But if you do it because you love it and you get to do it with people you love and you can do it out of a sense of gratitude and giving to other people. You know, Steve Jobs, one of my heroes, used to say, um, I get to work now with Johnny I. He started a firm called Love From, Love From Me To You. And that was the theory that Steve said, that Steve said the best way to show your love for the species is to put your heart and soul into something and give them to them. Steve said that design is a fundamental soul, the manmade creation that reveals itself through subsequent layers.

• 40:10Brian Chesky?

  And I think that ultimately, my motivation has gone from um, more extrinsic to more intrinsic. That at this point in my life, I'm less worried about what people think. I don't really feel like I have to prove anything to people. Either I already have or I never will at some point. And I think at some point, it just becomes about the thing. I just want to do the thing to the purest, best of my ability and to feel like I give to others. And this is the other thing, it's just amazing to be able to buy things and have things. Those experiences are awesome. But the things that probably give me most joy is like sharing things with others or giving things. I totally get now, I never understood like why people like giving away things. I didn't really understand it. It was not intuitive to me growing up.

• 40:55Brian Chesky?

  I was a parent of social, I was kind of middle class. And now I realize there's, I don't want to say a selfishness to it, but you get something. You get something from giving. It's not just this moral obligation. You actually get something. And what you get is this sense of love and connection by giving something. And by giving love, you kind of get it back in return. And I think ultimately, like. I think me as a leader, I never saw something like me growing up. Like I went to design school and like no, there was this weird thing, Jay, where I get to RISD, the non-school design, and there was this obsession about getting design in the boardroom. And Joe and I were like so like audacious, we thought, why should design be in the boardroom? We can run the boardroom.

• 41:38Brian Chesky?

  But of course, like designers, the people never thought started companies. And there's an old saying, art is a question, the problem of the world, and design is the answer. And Joe and I wanted to seek answers to problems in the world. And one answer was, we can't pay rent, so we created this thing called Airbend and Breakfast, airbeds instead of beds, for Airbend and Breakfast. But ultimately, you know, I think a business person, I am a business person ostensibly, but I think a business person's goal is to make money and a designer's goal is to solve a problem. And of course, I'm doing both. I probably sit at the intersection, but I don't get out of bed every day to make money. I get out of bed every day to like design something amazing. And of course, I can pay money, I can fund it. And that's just a kind of motivation and that probably can keep me going for a really, really long time.

• 42:21Brian Chesky?

  And I find that a lot of companies, they get really cold as they get big. That you start something for love, you're the customer, you talk to the customers, and at some point, the company grows. And you start with the head and the heart. You like putting your love into it, you're intuitive. No startup is data oriented, because there is no data. If you have an idea, there is no data. So you go off your intuition, you do something because you believe in it. And then at some point, you get so big, the company gets financialized, there's a lot more data, and you start making decisions with the heart and now with the head and one side of your head. And you look at the Fortune 500, how many CEOs in the Fortune 500 are truly like, have any creative background whatsoever, identifies creative? Almost none.

• 43:03Brian Chesky?

  Okay, how many boards, there's 12 members on average of a Fortune 500 board, that's like probably 6,000 members in the Fortune 500, how many boards have like creative people? Not many. How many executive teams have it? And so I guess the question is like, there's nothing wrong with the scientific method, there's nothing wrong, it's great. But we need to, we talk about diversity a lot in corporate America. There's a type of diversity we need, a diversity of artists and scientists of head and heart. You need all those things to solve the biggest problems today. And if Airbnb could be viewed as like a design-driven company, like the world's biggest RISD project that just never stopped, you know. A company with like a sense of a spirit.

• 43:45Brian Chesky?

  A sense, you know, our logo is like an inverted heart. It was meant to be this idea, almost of this like beating heart. Like this lifeblood that would flow through the community. And I'm not saying we do all that. That might be an ideal that we've never gotten to.

• 44:02Jay Shetty?

  But you can.

• 44:03Brian Chesky?

  But we can or will die trying.

• 44:04Jay Shetty?

  Yeah. You've sparked a lot of thoughts for me that I'd love to share with you that you've reminded me of so many things. My mind is connecting so many dots with what you're sharing. The first thing that came to mind is it's really, there's a beautiful statement by Paul Tillich, who's a writer who said that it's fascinating that there are two words in the English language for being alone, yet we only use one of them. And he said, the two words are loneliness, which is the word we use, and the other is solitude.

• 44:32Brian Chesky?

  Oh, yeah.

• 44:33Jay Shetty?

  And when you said we're disconnected from the earth, we're disconnected from each other, but really we're disconnected from ourselves. It's because of a lack of solitude.

• 44:40Brian Chesky?

  Yes.

• 44:40Jay Shetty?

  When I lived as a monk, being comfortable being alone was the first lesson of the day.

• 44:46Brian Chesky?

  Wow.

• 44:46Jay Shetty?

  Because the idea was that you could.

• 44:48Brian Chesky?

  And how do you learn how to do that?

• 44:49Jay Shetty?

  Well, there's, there's many techniques. One of the first techniques is if you just sit with yourself for long enough, you start to see so much in yourself that what connects back to what you said at the beginning. If you're able to explore and take an expedition into the darkest parts of yourself, if you're able to go into the inner sky and extrapolate all of the feelings, the messages, the emotions, the things you like, the things you don't like. Now, when you sit opposite another human, you can see the complexity and the simplicity of them as well. The challenge is we've never looked at our own darkness and complexity.

• 45:22Brian Chesky?

  There's a great, one of the late, great mythologists of the 20th century, you probably know is Joseph Campbell.

• 45:28Jay Shetty?

  Of course, I love Joseph Campbell.

• 45:29Brian Chesky?

  He had this great quote, "The cave you fear to enter lies the treasure that you seek." And I think that so many of the things we do in life are to run away from things, to avoid opening that closet to see what that monster is. But that's where the treasure is.

• 45:43Jay Shetty?

  Exactly. And so being trained to sit with that monster with the discomfort of what that actually looks and feels like. And what you were just saying now about this heart and this head, or the design and the art and the creative and the entrepreneurial, I think is so powerful because, so you mentioned Steve is a, is a hero of yours. Same with me, I feel like I've studied everything he's ever said or written. And one of the things I love, this was an interview that Mark Zuckerberg was doing with Prime Minister Modi from India. And he said this on stage to Modi, I believe this was in San Fran, and Mark said to him, he said, when he was struggling with the direction of Facebook, now Meta, in 2009, which is five years old, Facebook is, right? He went to his mentor, his mentor happened to be Steve Jobs. And he said to Steve, he said, what do I do? I'm struggling.

• 46:28Jay Shetty?

  I don't know which direction Facebook should go in. Now, if you think about 2009, Steve Jobs is undoubtedly one of the most connected humans on the planet, has access to money, tech, everything you could possibly ask for. And Steve says to him, I want you to go and live in an ashram in India.

• 46:43Brian Chesky?

  Wow.

• 46:44Jay Shetty?

  For, I want you to go live there and I promise you, if you go there, you'll figure out the direction of Facebook. And Mark said he actually went to that monastery, that ashram. And he said in that ashram, that's where he decided that at that time, Facebook was about connecting people.

• 46:56Brian Chesky?

  Oh, wow. I didn't know that story.

• 46:57Jay Shetty?

  Yeah. And what I find fascinating, the reason why I like to share that story is I'm always fascinated by what a tech entrepreneur thinks, as much as what I'm fascinated, what a monk thinks, because it's that cross pollination, it's that extreme of diverse thought where those two things don't collide, they don't have the same agenda, we're not living in an echo chamber. When you're talking to an artist and an entrepreneur, there's no echo chamber, you've broken it open now. And so for me, MIT did a study on that, where they found that the most innovative employees inside an organization were people who didn't know people who knew the same people. There were people who knew people who had random connections. So their network chart was completely uncorrelated, whereas people who had networks who were correlated

• 47:41Jay Shetty?

  were less likely to be creative and entrepreneurs.

• 47:43Brian Chesky?

  Fewer unknown discoveries. And I feel like in my own life, like Steve has a saying, you can't connect the dots looking forward, you can only connect them looking backwards. I grew up playing ice hockey, I played team sports, I went to a military high school, a design college, where I first studied fine art, then design. Then I went to MIT for a semester, we did a cross enrollment product development program. Then I went to Los Angeles as a designer at a firm. Then I went to Silicon Valley with very little and like got thrust into the technology industry. And it turns out that like, I did not know how any of these experiences would add up together. And they all came to me and every single one of them have used every single experience,

• 48:26Brian Chesky?

  but I could never have reversed engineered how to get there. And it is amazing that like you, Steve used to say, the best engineers were also poets. And he was really saying that like creativity is about connecting dots. It's about having disparate experiences and bringing them together. And if you haven't had a lot of different experiences, if you aren't very multidisciplinary, you're not going to be able, I mean Einstein was like a violinist. I think a lot of the greatest scientists have leaps of the imagination. They're not just using empirical information. And a lot of the greatest artists, they have an organized minds. Sometimes they have a fascination with numbers and you know, so you start to, you start to bring things together and I think that is exactly what we probably need in this world.

• 49:10Brian Chesky?

  I mean, we need more creativity. You know, whenever you see two bad options, you don't like it. The right answer is the third option. The third option is one you haven't come up with yet. There requires novel, innovative, imaginative thinking. Where does it even come from? Where does creativity come from? If creativity, you know, but I don't know if Einstein never said this, but there's a quote attributed to him that is that logic can take you from A to Z, but imagination can take you anywhere. I love that quote. Don't know if he said it, but I believe it. But where does that come from? Where does imagination and creativity come from? I think it comes from a sense of openness. It comes from curiosity. It comes from maybe not first following your passion, but following your curiosity with a deep.

• 49:53Jay Shetty?

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• 50:36Jay Shetty?

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• 51:56Brian Chesky?

  Intensity and being curious about so many different things and trusting that you can be curious about something and learn about something, not knowing if it will ever be useful. And have the trust to say that every single thing you'll do in your life, you'll do with accumulation of every single experience you've had before. And that the more places you've gone, the more people you meet, the more things you learn, it will all come to you. And you might not know ahead of time how it will be useful. And honestly, if I hadn't gone to military school, I probably wouldn't have been so organized. If I didn't go to design school, we probably wouldn't have been as creative and innovative in our thinking. If I hadn't played team sports, I probably wouldn't have understood about camaraderie. If my parents were social workers, I don't think I would have had this focus on service

• 52:41Brian Chesky?

  and connecting people. And I could never have imagined any of those things being useful. Because growing up, I didn't know what I wanted to be. I wasn't athletic enough to be a famous athlete. I wasn't handsome enough to be an actor. I wasn't enough singer to be a musician. I did not think I was going to be an astronaut politician. And so I'm like, I don't know who I'm going to be. I don't know what I am. And like the word entrepreneur was a word I'm not even sure I heard of growing up. It was like, to me, it was an obscure French term. I didn't know what it meant. And I saw Walt Disney as a kid on television. I thought, one day I'll work for him, not thinking I would start a company just like him. And I never imagined that was possible. I guess we're all born with unknown potential, as I said before.

• 53:22Brian Chesky?

  But you have to live experiences as many as you can. You put them together. And I hope my story inspires people, not for the remarkableness of it, but the ordinariness of who I was before. To say that like, if I joined the, you mentioned the giving pledge. If you ask my teachers in high school to predict which other students would be a signatory of the giving pledge, I do not think I would have been the top of their list. I don't think that takes anything away from the teachers. I think it just means that maybe that potential is in so many of us, and it's also maybe a little bit random and anything is possible. And you, like, the story you tell yourself might not be accurate.

• 54:01Brian Chesky?

  And I, I, I hope that my story inspires people from the ordinariness of where it came from. That I was just like everyone else, but like, you know, a hundred thousand decisions later, with enough resilience, creativity, curiosity, determination. You wake up one day, you're like, oh, my God, look where I am now.

• 54:22Jay Shetty?

  What I really value about that perspective is, as you were defining creativity in so many brilliant ways, one thing that came to my mind was, creativity is being able to connect the dots where everyone else sees anomalies.

• 54:35Brian Chesky?

  Yes.

• 54:36Jay Shetty?

  And so if you look at your journey, just as a series of random dots, they're all anomalies. Social working, hockey player, design student, like, they're just random things. But you're able to actually paint this tapestry where you're going, well, actually, everything that I do today. And I've, I've often felt that in my own life, that I lived as a kid growing up in London. My favorite subjects at school were art and design, philosophy and economics. Those are my favorite things in the world. Spent my entire life being immersed in that world. When traded it in to go to Cass Business School to study management science with a focus on behavioral science, because I thought it gave me a career, only to give it all up, the safe job to go live as a monk.

• 55:14Brian Chesky?

  Right.

• 55:14Jay Shetty?

  To then come back to the real world, go back into the world of business, because I just had to pay the bills and survive. Went into consulting, then came out and do media now. And I completely agree with everything you've just said.

• 55:26Brian Chesky?

  And probably the thing that makes you so unique is like, you were a monk. And you are an entrepreneur and you lived in London and you lived in New York. And like the accumulation of all those experiences together.

• 55:40Jay Shetty?

  Correct. It's the end.

• 55:41Brian Chesky?

  Is made is made you who you are, not one of them, but all of them. And I think that like the one advice I would give my college self is to try more things and have more experiences and don't seek status. And part of the reason why one should not seek status is because we can't even predict what industries will be around the future. Like growing up, status to me was like, um, I don't know. It was like being an investment banker or something or something. And I don't know. It was like fields that may not even totally exist in their current form in the future. So, you know, I like to say like, you should do things you're good at. You tend to be good at things you're interested in. You should seek out whatever you're curious about, whatever you're interested in. And then you want to get to the frontier in some way.

• 56:23Brian Chesky?

  At some point you'll learn everything and you'll get to the edge of all that's known about that subject. And that is an uncomfortable period where you peer off the ledge of a cliff. And that is where you enter a frontier. And if you can then peer over the edge of cliff and then get a little bit further and extend our understanding, give us a little bit more land. That is how you like add to, as Steve Jobs said, that's how you give your love back to the species and create something for other people. And I think, I think it's amazing that like anyone can do that, you know? You can do it because anyone can do it at any scale, you know? And you can do it in your humble way, like on the side, something small, or you can do it in a really big way. But it feels the same, no matter what the scale.

• 57:03Jay Shetty?

  You just told us what you'd say to your younger self. If you met your younger self now, let's do this exercise. What do you think your younger self would say to you? What would it be proud of? And what would your younger self say? We need to reconnect with this.

• 57:17Brian Chesky?

  The first thing my younger self would say is, oh my God, how did you do all this? And I would be totally perplexed. When I started me and my friends, I said, this will be huge. One day, thousands of people will do this. Like that was my, my sense of what was possible. It's hard to dream of something you've never been exposed to. And it's hard to imagine becoming something when you didn't have any data that you could ever do anything like that in your past. And so I do not think my younger self, let's say my, my college self, did not think I could run like a Fortune 500 company, you know? You know, for every $1,500 spent in the world, $1 spent on Airbnb. Did I think I could lead an organization that's facility on? No, I did not think of it.

• 58:01Brian Chesky?

  And so that would be probably the thing I would be like surprised in a very positive way. But the other thing I would probably say is, wow, I'm 41 years old. And I live alone. And I probably thought by now I would have a family. And I've always wanted to have one. And I think that for all the like, attention adulation I get, I think I would have maybe looked at my life now or my recent life and identified a little bit of isolation. And I think the lesson is a couple of things. One, I think that things have happened in a different order than I imagined. It's hard to predict. I thought I wouldn't, I didn't think I'd be this far along in my career.

• 58:44Brian Chesky?

  And I probably think, I probably thought I'd be further along and have something different in my personal life. And I also would probably, I would hope the college me would tell myself now, you don't have to keep proving something to anyone. Because you've proven more to me than I ever thought was possible. And I think that like, part of me, and this is probably true of a lot of people, we have this tape loop of like, whatever we thought of ourselves as a child, like it's just frozen in times, repeating ourselves. And you just compulsively just keep doing something. And like, many people have addictions and I probably had one that was probably work. And, um, and I think I'd have to, I would hope my childish self would, or my younger self would remind me that, you know, maybe there'd be a wisdom that like, the happiest periods of my life were with other people.

• 59:28Jay Shetty?

  Thank you for that. Thank you for opening up and going there. And I felt that. What is a thought that you say you have too often?

• 59:35Brian Chesky?

  I wonder what they'll think. Speaking of Dr. Waldenker, Robert Waldenker.

• 59:39Jay Shetty?

  I love him. Yeah, he's a good friend.

• 59:40Brian Chesky?

  But I met him last week for the first time and you've had him on your show, right?

• 59:44Jay Shetty?

  Yeah, we've spent a lot of time together. I love him.

• 59:45Brian Chesky?

  Something you told me last week that really stood out to me, you said, one of the biggest regrets that people have in their life is having lived their lives worrying what other people think. And I kind of understand why, like, from a like evolutionary standpoint, like, you kind of have to care what people think because you have to fit in. And if you don't fit in, you don't belong. You're isolated. If you're isolated, it's a death sentence when there's, the only thing you have is the village. But it turns out that like, that is not true anymore, that like, it's okay to be misunderstood. And that it doesn't, maybe it doesn't matter what people think, or maybe it doesn't matter what they think today. And that some of the greatest things I've ever done, I was at least temporarily misunderstood. And maybe it only matters what a few people think.

• 1:00:27Brian Chesky?

  And maybe, just maybe, the person that most matters, what I, what they think is yourself, right? That you just listen to your own voice, not other voices. And I, I think if I can do that, you know, artists will call that artistic integrity. Right? You had Rick Rubin on the show, he talks about like, the best way to make a popular song is to make something you like. And that's about it, not make something for somebody else. And, um, and that's, that's something I, I have to continue to do. And the crazy thing is, the more successful you get, the more you start kind of performing for an audience. And you have to be very careful about performing for and appeasing an audience. And once you become something, people expect you to be that thing.

• 1:01:12Brian Chesky?

  You know, imagine like you having to be something forever. But what if you change? What if you grow? What if you want to do different things? And that's a challenge I have, right? The Airbnb brand means something. I need to be careful about changing that brand. It stands for something. And yet, I as a person, I'm not meant to be the same person every year. I mean, how could I be? I learn, I grow, I change, I have new experiences. And so having the permission to continue to change and evolve and not be so self-conscious of what, what people think. That's something that I always cha, I struggle with because I know a part of me, I think I'm like a people pleaser. And one of my challenges historically be is like, some people like, I'm like, I don't always like interpersonal conflict.

• 1:01:56Brian Chesky?

  I like to appease people, make them happy, and that's got a good side. And it also can be a bit of a prison over time. And the bigger you get, the, the, the higher the walls get.

• 1:02:05Jay Shetty?

  I want to just point out something you said that was so subtle, but so powerful for everyone who's listening and watching. I've never heard it put that way, but the idea that. We often think it doesn't matter what people think. And you said, it doesn't matter what they think today. And, and that was so subtle, but so powerful. Because I think when we live in a world where like, oh, it doesn't matter what anyone else thinks. It's, it can be negligent. But the idea that it doesn't matter what they think today about what I'm thinking.

• 1:02:27Brian Chesky?

  Thank God.

• 1:02:29Jay Shetty?

  Yeah.

• 1:02:29Brian Chesky?

  Thank God, you know why? When I, when we first came by the idea, one of my first investors said, don't worry about people stealing your idea. If it's any good, everyone will dismiss it. We tend to believe things were good in hindsight. Some of the most revolutionary people and ideas were revolutionary because they were misunderstood in their time. That if you have to be at some point in your life, willing to be misunderstood. And the solitude you can have are two things, I think. Number one, to not be so attached to it. To realize that ultimately you can't predict the outcome. Just do what you believe, follow your heart. And if it's true, whatever has happened is meant to be. But the other thing you can do is to escape into the future. To say, to have this, we call it a vision for a reason.

• 1:03:12Brian Chesky?

  You envision something that people don't see yet. And say, I'm willing to be misunderstood to try to follow this thing. And if I believe in enough, eventually other people might see it. And if you are able to be misunderstood just for a little bit, that's what it feels like to truly revolutionize something and change something.

• 1:03:32Jay Shetty?

  There's a beautiful statement, which is probably my favorite, which you've just encapsulated so well. It's from Charles Horton Cooley. He wrote it in 1896 or something like that. So he said this early, and when you hear it, you're like, wow, that was said yesterday. He said, the challenge today is, I'm not what I think I am. I'm not what you think I am. I am what I think you think I am.

• 1:03:55Brian Chesky?

  Oh.

• 1:03:57Jay Shetty?

  And he said, we live in this perception of a perception of ourselves. So we don't even know what we look like. We, we are who we think other people think we are. And that's twice removed from yourself. And that distance we create from our understanding of ourselves versus what we think someone thinks of us.

• 1:04:14Brian Chesky?

  Totally.

• 1:04:15Jay Shetty?

  How will you ever know? What, what do you think is something you are still trying to understand about yourself? Or if you think you misunderstand a part of who Brian is, what are you still trying to understand?

• 1:04:26Brian Chesky?

  I think that we tend to have an outdated image of ourselves. And that makes sense, right? Like, think about, I'm 41 years old. So my image of myself is the average of the last 41 years. And if the average of the last 41 years, the median is 20 years old. And so I still see myself a little bit like that person. And people, most people see me today and a lot of people are going to see me for the first time right now and that's their impression. And that's a delta. And I often wonder like, sometimes I, you know, I probably have had a little bit of imposter syndrome, like what do people see in me and why do they follow me? And like, I, because they do, like at some point you're a leader and you're a leader because people choose to follow you and you don't like impose yourself on them. They ultimately believe in something.

• 1:05:10Brian Chesky?

  And I think I'm still trying to like, maybe come to terms with that. Like, what does this all mean? I think I'm still trying to understand what will make me happy, especially at a personal level. I think I've found what will make me happy at a professional level. I, I was really lucky that I discovered something that I love very early on. I found a perfect harmony between what I was good at, what I loved and what kind of society valued and those things just clicked into place and I was able to find it. But I think I've been on a lot longer journey to figure out like, what will make me happy like in a larger sense of the word?

• 1:05:48Brian Chesky?

  And it turns out that success and status to some extent have benefits and, you know, but it's not, it's certainly, to say it's not, everything's an understatement. I think I'm still trying to, I'm still trying to learn that. And maybe I'm trying to figure out, you know, at this age, with so much, so many resources, like, I almost feel like in a way, my life's just beginning. And so it's just beginning, then, and I can't connect the dots, looking forward. It's a discovery of who am I and who am I meant to become? Like, is this my story or is this the end of this, the middle of the story, the beginning of the story? And what am I meant to do next?

• 1:06:32Brian Chesky?

  And I'm, I'm kind of learning a lot more about myself every year.

• 1:06:35Jay Shetty?

  That's a brilliant mindset. That's, that's so empowering and I'm hoping for everyone who's listening and watching, that is so phenomenal to hear from you because.

• 1:06:47Jay Shetty?

  That is the journey of life, like the questions you just laid out. Like if you weren't asking those questions, how boring would life be? Like, how unmeaningful and unfulfilling would it be? And the fact that you're asking those questions at this point.

• 1:06:59Brian Chesky?

  Maybe one other thing can I add?

• 1:07:00Jay Shetty?

  Oh, of course, you can add wherever you want.

• 1:07:02Brian Chesky?

  So, over a year ago, it was February, Russia invaded Ukraine. We got word that there would be like millions of refugees. And when this broke out, I remember my co-founder Joe calling me up and him telling me something. He said, "When a crisis of this scale happens, we should ask ourselves one question." And that question is, "How can we help?" And I always wanted to believe that if I was like a CEO during World War II, I would have like been helpful. And I want, I always try to use, that's the other device I use. I try to think about how I'll be viewed in the future, but I also want to, I always think in a crisis, "How do I want to be remembered?" Even if no one will remember me. And I think anyone can do that.

• 1:07:47Brian Chesky?

  How do you want to be remembered by history? Even if it's just an intellectual device, because maybe not a lot of people remember. That's okay. But live your life as if you'd be remembered. And what I realized was one of the most important things. And then we ended up helping provide housing for over 100,000 refugees. And it was an incredible team effort. But it came from this basic idea of, "How can I help?" And maybe that is the other version of my question of my life. At this point, you know, how can I help? With everything I have that, I mean, I've hired some of the most talented people in the world. We have enormous amounts of resources. We have this incredibly advanced technology. I have this pretty big megaphone. What do I do with that?

• 1:08:29Brian Chesky?

  And I, I hope that what I do provides me happiness. And I've noticed that the things that make me happy are like, kind of helping and giving others. I don't mean to sound cliche, but like, you start to realize like, what provides happiness and value for you? And so that's kind of something that I keep thinking about. And that's what I love about like entrepreneurship and creativity and design, is you make something, maybe initially for yourself, but then for other people. And the real joy is seeing them use it.

• 1:08:59Jay Shetty?

  Absolutely. I think, I was really fortunate. When I, when I lived as a monk, service was trained as the highest act. Service was like imprinted in us as the highest act, that the act of giving, the act of serving others.

• 1:09:12Brian Chesky?

  Interesting, yeah.

• 1:09:13Jay Shetty?

  And it was so counterintuitive to everything I'd learned growing up in London, because it was all about getting and achieving and giving and serving were never part of even our vocabulary, let alone being a part of life. And I realize now, and I see that today, that when everyone, when anyone gets to a point of getting everything, all they can do is give it away.

• 1:09:33Brian Chesky?

  Yes.

• 1:09:34Jay Shetty?

  In the right, in a way that fuels them to a mission that is aligned with their purpose, not just, not just, you know, wherever it goes.

• 1:09:41Brian Chesky?

  Exactly.

• 1:09:41Jay Shetty?

  But in a meaningful way. You talked a bit about, which I loved about the, you know, the younger self saying back to you that, you know, you thought that things would happen in a different order.

• 1:09:52Brian Chesky?

  Yeah, totally.

• 1:09:53Jay Shetty?

  When you think about that, being single or being, in, in your words, like being lonely, you're such a mastermind at so many things. What's the thought that blocks that? What's the worry that comes up? The anxiety that stops you from masterminding that part of your life?

• 1:10:10Brian Chesky?

  I've been able to look inside myself to know a number of things. I think that I grew up feeling a little bit like an outsider. I wanted to feel like anyone, like I belong. And I found through achievement that, you know, I would feel these feelings that I thought were like love and, and I would feel better, you know, and all that. And I think it's this incredible and positive to a point, but if you're not careful, it can become all consuming. And the thing about a tech company or a start, a startup is like, it's like, imagine you, you like, again, you have a three person band that's now thirty thousand person band, you know, or three million person. It just, it, there's always more you can do.

• 1:10:54Brian Chesky?

  It can, if you're not careful, become like a one dimensional addiction. And I think that it's like the thing that made me successful was my singular focus. But I have to be careful that the thing that could then turn against me is my singular focus. And so I think it's like what I, the way to live my life in the next 20 years can't exactly be what I did in my last 20 years. The last 20 years worked out pretty well, so why would I do anything differently? But of course, if I don't do anything differently, then I'll be 50 or 60 and nothing will have changed. And so I think it's really about like, Seeking community. The word community means harmony, to live in harmony, in balance, and having that.

• 1:11:39Brian Chesky?

  And so I think it's just old habits and habits that been rewarded. So, but you gotta be very careful about those habits. I think that's what it is. And I also just, yeah, I don't know. What do you think?

• 1:11:52Jay Shetty?

  When I listen to you and being with you for the time that we're spending together, and obviously it's the first time we've met.

• 1:11:58Brian Chesky?

  Yeah.

• 1:11:59Jay Shetty?

  You're someone who has extreme clarity about what you want, who you are, what you're working on, what you're struggling on. And my question would be, or my hypothesis is, does that clarity exist around what you want in the personal space?

• 1:12:14Brian Chesky?

  I think that's a big insight.

• 1:12:15Jay Shetty?

  Yeah.

• 1:12:15Brian Chesky?

  And maybe that's what I'm still trying to discover.

• 1:12:17Jay Shetty?

  Yeah, I would say that you sound so clear.

• 1:12:19Brian Chesky?

  Yeah.

• 1:12:20Jay Shetty?

  That if you actually had clarity, then I don't think it would be hard. But it's hard to have clarity. That's the hardest thing in life.

• 1:12:26Brian Chesky?

  The hardest thing is to have clarity. That's a good point.

• 1:12:28Jay Shetty?

  And so when you have clarity, it will be so much more easy for you to create. You can't create something if you don't have clarity.

• 1:12:33Brian Chesky?

  That's a great point.

• 1:12:34Jay Shetty?

  And so that would be my hypothesis at least. And that's what I was gonna ask you. What at least are those sprinklings of those clues? Let's go with that word. What are the clues of what you think could develop into clarity around what you're looking for in a personal way? You've talked about so prolifically about what you want professionally, which is this using Airbnb as this phenomenal platform to build community and connect people and, you know, eradicate loneliness, which I love. Like, I love that. That's phenomenal clarity. And it's so inspiring. And I could get behind that today, right? Like, that's... So what do you need to get behind yourself in the personal space?

• 1:13:09Brian Chesky?

  I feel like I'm professionally like a 60-year-old in a 41-year-old's body and personally like a 25-year-old in a 41-year-old's body. Because I'm like, I have a foot in the future and a foot in the past. Or like, I'm in totally different time scales professionally and personally. And it kind of makes sense, right? Where I am, a whole bunch of my life maybe was a little more on hold or done in a different order than I imagined. So the question is like, how do I get clarity? When I started Airbnb, before we started Airbnb, I didn't know I wanted to start a tech company and I wanted to be like about bringing, helping bring people together. And I was gonna start with these two people and I was gonna be a technology founder and I was gonna marry art and science and do all this stuff. I couldn't have known any of that.

• 1:13:52Brian Chesky?

  But there were some things I did professionally that are probably clues to what should be done personally. The first thing is I had endless curiosity. I had role models, heroes, people I looked up to and, you know, both, you know, well-known people and lesser-known people. I had an intense curiosity. I was drawn to certain types of people. Um, and I had action. You know, it's like, if you can't follow your passion, you follow your curiosity, where does it take you? And, you know, like, you're not going to start a company by like, never like, starting and you're not going to build a personal life you're, you want by not starting either. And so you just go on that journey and you, you will, you will, I think you will find what you want if you start and you keep moving.

• 1:14:37Jay Shetty?

  Yeah, that feels right.

• 1:14:38Brian Chesky?

  Something like that.

• 1:14:39Jay Shetty?

  I'm excited to see you, you know, I'm excited to hear about how you take that short moment of clarity that we've gained into the future because

• 1:14:49Brian Chesky?

  No, that's great.

• 1:14:50Jay Shetty?

  I really, I really, really feel that you've found in your life that you've always been exactly where you're meant to be. Not in the luck sense, like you said, of the right timing.

• 1:14:59Brian Chesky?

  Right.

• 1:14:59Jay Shetty?

  But that each one of your experiences

• 1:15:01Brian Chesky?

  Totally.

• 1:15:02Jay Shetty?

  has made you make better decisions.

• 1:15:04Brian Chesky?

  And I think that maybe the, the like, exciting thing is like, what if I can't connect the dots looking forward? But I will realize in hindsight, wow, everything just fell into place. Like this thing led to that thing, led to that thing.

• 1:15:16Jay Shetty?

  Yeah.

• 1:15:16Brian Chesky?

  And that would be fun, it'd be fun to check in in a handful of years and see what played out.

• 1:15:20Jay Shetty?

  Yeah, yeah, definitely, definitely. And it's so, it's so interesting that you keep quoting this. I've never met someone who loves quotes as much as I do. So it's, uh, it's fun hearing them back from you and how they played out in your life. What, what if anything today, apart from everything we've talked about, we've talked about so many things. What if anything today keeps you up at night? Or do you sleep pretty well?

• 1:15:41Brian Chesky?

  I don't know if I sleep that well and I, not to use another quote, but Pablo Casado had a saying, the older you get, the stronger the wind gets and it's always in your face. And I think that could be true of companies. What keeps me up at night is, you know, like, like people ask me in the professional context, what keeps you up at night in the company? Like, is this something happening? What keeps me up at night is something not happening. What keeps me up at night is the idea that we grow into something that I like, was meant to disrupt. Two thousand nine, Airbnb takes off. So we started in 2007, 2008, it takes off by 2009. I go on a 10 year journey. It's now late 2019 and I remember having a dream, a bad dream, that I woke up and I was running a company that was unrecognizable

• 1:16:25Brian Chesky?

  from anything I ever intended to start. It was like I was in a wilderness for 10 years and I just, and I came back and I remember going on a hike in Bellinas, California, where Joe had like a summer house. And we went on a hike, Joni and I. And I told them about this dream and they said, well, what did you find? I said, I was horrified because the company we set out to start is unrecognizable we have today. And they go, what do you mean? I go, well, people are complaining that it's big, it's bureaucratic, it's slow moving, people are more complacent, costs is rising, growth is slowing. It's starting to feel like a corporation. And I didn't know what to do. I felt like we needed to like, not blow it all up, but change it all, like take the house back to the studs. But the problem was we're about to go public.

• 1:17:08Brian Chesky?

  And that's like a really bad time to do that. But I have this image in my head of this kind of company that I want to have. This image was to build the most creative place on earth, to build the world's biggest startup, to build a company that was like felt small, that was completely focused not on a product or service, but a community. I was starting to come to conclusion by 2019 that you can't be big and have a soul. Like at some point, those things were at odds, that the problem was being big. And I didn't know what to do. And all of a sudden, we get word in February 2020 that our China businesses collapsed by 80% because this thing called COVID. We're like, what's COVID?

• 1:17:51Brian Chesky?

  And then within eight weeks, you lose 80% of your business. And I've never had a near death experience, but it's been described to me as your life flashes before your eyes. And I had a near business death experience. And then suddenly, everything became clear to me. If I was sitting in this chair three years ago, I would not have been clear. I don't think I would have the clarity I had today. There's something about almost losing everything. And everything I had, at least at that time, I thought was the professional. That gives you clarity. Imagine your house is on fire. And someone says you can take 20% of the things out of your house. Suddenly, you have to make that choice. And you get really clear about what's important. People start telling you, I want everything to exist. You say, why? And they tell you.

• 1:18:34Brian Chesky?

  It's as if they're giving you the eulogy before you're even dead. And how you want to be remembered. And you start to ask yourself. I don't know what's going to happen, but how do I want to be remembered? And at that point, we stepped into action. And we basically rebuilt the company from the ground up. And this is, again, bring it back one more time to Steve Jobs. I met two people at that point in my life who changed my life. One was Johnny Ive, who was Steve's partner in design. And the other was Hiroki Asai, who was Steve's creative director. And they told me about the way Steve ran the company. And actually, a funny, even further aside is, I remember one time. I remember went to Steve's house. I never met him.

• 1:19:17Brian Chesky?

  But and I saw these books on the shelf from Robert Oppenheimer. And I asked his wife, what is with the Robert Oppenheimer books? But as I started studying, I realized that it was this idea that you, almost like Robert, kept the whole bomb in his head. That this idea that the leader collects all the information. And that you're the center, that it's not a pyramid. You're not top down, you're inside out. You're the son of a solar system. But your job is to emit light and bring decision making in, to pull in the shared consciousness. And I started realizing there was a whole new way to run a company. A company that wasn't divisions. Think about what that sounds like, divisions. We are divided, but totally integrated. As small, lean, elite as possible.

• 1:19:59Brian Chesky?

  Creative and analytical technology and humanities that we'd have one.

• 1:20:05Jay Shetty?

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• 1:20:50Jay Shetty?

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• 1:21:32Jay Shetty?

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• 1:22:02Brian Chesky?

  Flow. We wouldn't be metrics oriented. We'd be basically idea oriented and we'd measure the results in that we would just, there's this really specifically ran a company. And that was basically the way I found ourselves out of a crisis. And so the lesson of the story is through that I was able to get a lot of clarity through this crisis. I was forced to answer and ask all these questions that I never had to do before. But I hope on the personal side, I don't need a crisis to answer those questions.

• 1:22:33Jay Shetty?

  Yeah, that's exactly where I think we're headed, that you have. You have an opportunity to avoid the crisis.

• 1:22:40Brian Chesky?

  Yes.

• 1:22:40Jay Shetty?

  In order to not be.

• 1:22:41Brian Chesky?

  Not everyone needs that crisis.

• 1:22:43Jay Shetty?

  No, you don't. It sounds like, do you, do you still, when you present ideas, they're so visual, you see them. I feel like you can see everything you're talking about and I can, I can see it with you.

• 1:22:53Brian Chesky?

  Everything in my head, I, my mind is like a three dimensional model. And all my ideas, think of it like a tree. The trunk of the tree is your very first principles, your root ideas. And then they have branches and the branches have branches and those branches have leaves. Or it's like a space, a three dimensional space. It's multi dimensional and colorful. And this is what we call the model, your model of the world that you want to live in. And as you gain more information, you keep changing the model in your head. I kind of describe my mind running Airbnb as imagine a chessboard. And there's, you have to see a few moves ahead. Now imagine like a die, a thousand sided die, each playing a separate game of chess, all simultaneously, anticipating and understanding relationships.

• 1:23:38Brian Chesky?

  As hard as that is, if you can start to organize all the ideas in your mind, but not be rigid, continually changing and orienting it like, you know, this is how I tend to see things in three dimensions, spatially. It's really rich, vivid colors. And that's just how I think, you know, I think other people will think in abstract thoughts or numbers, some think in terms of language. But that's how I do it, you know, and it probably doesn't surprise you, given my background.

• 1:24:07Jay Shetty?

  And do you see yourself in that or is that happening and you're observing it?

• 1:24:11Brian Chesky?

  You know, you might've hit on something. There have been times where I'm trying to design a world that other people want to, I want other people to live in. And I think it's like I want to vicariously live through them. It's like I want to design this house. That's the nicest house in the world for everyone to live in. But I'll be in the workshop designing the house. And sometimes I have to stop to say, maybe I should step inside that house. And I think that, I think that's a crux of it, actually. And to answer your question, I sometimes see myself in the house. And sometimes I see myself just kind of almost like a monk or, you know, in a, in a technical and design monastery.

• 1:24:55Brian Chesky?

  Like, you know, and that's kind of what the pandemic was. I described it almost like a monastery, except with Zoom. But, but if you didn't know I was on Zoom, you'd just think I was meditating all day. Right? Like, I'd just be sitting in one chair. And so that's a great thing is I, I think that sometimes, many times, we as leaders, especially tech founders, I think that many tech founders basically designed the kind of world they want to live in because the world they grew up in was inadequate in some way and did not make them happy. And I think the challenge of those tech leaders is to make sure that they step inside that world and live that world themselves. And when you don't do it, then sometimes you start to like, forget why you do things and you get disconnected.

• 1:25:39Jay Shetty?

  Wow.

• 1:25:40Brian Chesky?

  Just kind of, you're making me think of all this now.

• 1:25:43Jay Shetty?

  You're making me think too. I love it. No, and, and that resonates so deeply and strongly because I also think that without purpose, tech entrepreneurs also can sometimes, not even just tech entrepreneurs, entrepreneurs in general, or anyone can build something that they monetize that they would never want to live in too.

• 1:26:01Brian Chesky?

  Yeah. Sometimes people don't know why they're doing it.

• 1:26:04Jay Shetty?

  Correct.

• 1:26:04Brian Chesky?

  They, they started it for a reason. Maybe the reason was extrinsic, I want to be rich and successful. Maybe it was intrinsic, maybe there was something, but even so. Then you find yourself waking up one day asking, why am I still doing this? And you know, the number of people that forgot why they're doing it? The number of people that are self-driving cars? There's a destination that's in the car, they're driving towards it, but they don't even know what that destination is. And that's when you don't look inside yourself. And if you're not careful, you will basically be on a superhighway going somewhere, not knowing why you're going there. And you may wake up and end up in a destination that wasn't where you intended.

• 1:26:49Brian Chesky?

  I think this, having this clarity is so important. Who am I? What do I value? Like, what do I want to do in this world? It's like taking the time to reflect. And I think the best businesses are really introspective by introspective leaders. Like when we started the company, we were really clear, here's our mission. And it wasn't just like a mission statement. It's like, here's exactly what you're trying to do. And now what changes? Here are our values. Here's the kind of people I want to like work with. Well, what do they all have in common? They're curious, they're optimistic, they're kind of creative. They tend to like hosting other people. Okay, those become what we call values. What are the shared lessons? What are the shared stories? And the more you can start to be really reflective, you're right. The more you're clear about what you want, the more you get it. Our problem isn't in life, probably, that we don't get what we want.

• 1:27:33Brian Chesky?

  The problem is we don't know what we want, maybe. Or we pursue things unconsciously wanting that are counterproductive to what will make us happy. And if we can just wrap our arms around that, some of the hardest things to change are our own thoughts. But in a weird way, they also seem like the most possible to change. And so that's something that I've seen, like, some of the loneliest people I've met are some of the richest people I've met. Some of the most isolated people I've met are some of the most successful people I've met. Some of the most confused people I've met are the most powerful. Because at some point, the power and success can be confusing. You know, you had a purpose, but you also have all these demands and these stakeholders. You can get fused by appeasing people. And you, like, I think that happened to me.

• 1:28:18Brian Chesky?

  Like, I think I started Airbnb and I had a really clear vision. And I think I got into a wilderness where I kind of got confused. And a lot of founders have described becoming confused. A lot of leaders get confused. And I totally see how that happens. And I think finding your way back home is key.

• 1:28:37Jay Shetty?

  I would be intrigued to see if you close your eyes now or whenever you chose to, to see what you saw when you looked at your personal life. You're talking about your professional life as being all these thousands of decisions, moving.

• 1:28:51Brian Chesky?

  And you say like, kind of that period of self-reflection, right?

• 1:28:54Jay Shetty?

  Yeah, like.

• 1:28:55Brian Chesky?

  I think I saw somebody who was kind of almost punishing myself in romanticizing suffering. Because I thought, in some extent, I maybe believed that I was going to give everything to the company. And it was like this selfless act, but it became so selfless that I then could start to lose a sense of myself. I mean, you know how weird it is? I always kind of joked like, if I die, will I die Brian Chesky? Or the Airbnb guy just died, you know, like, and like, am I Brian or my Airbnb? And like, you know, like, they get really, one is an icon. That's a noun and verb you know ubiquitously around the world.

• 1:29:37Brian Chesky?

  The other is a person that not a lot of people know, really know. And when you, it's very careful, I started becoming the company. And this company started becoming me. And I think seventy percent of that was good. Because that meant the company, I think, was a person, had a face, is humanistic, it was in the details. But when you become a company, you cease to be a person and then you lose a sense of yourself. And then you become an icon, and by icon, I don't mean fame, I mean iconography. Icon is short for an iconography, and iconography is for a symbol for something. And of course, people are much more than symbols. And I started seeing that I started becoming a symbol and a thing.

• 1:30:23Brian Chesky?

  I stopped listening to myself. And by the way, like you get pressure from shareholders to like drive a stock price. You get pressure from, you know, employees to make it a better work environment. You get pressure from hosts, but no one gives you pressure for yourself in your personal life. If you don't create that own pressure, you will like, that will be the like, that's the one person that may not put their hand up. Hey, everyone else will. And if you don't listen to yourself. And I think that's been part of the second chapter of my life is like, kind of designing the world I want to live in and then living in that world and choosing to actually live in that world. And you'd be, I mean, you've interviewed so many people. So, but I'm so surprised how many leaders don't actually

• 1:31:07Brian Chesky?

  live in that world. I, I tend to think that like some, yeah, some of the most successful people are people that they get so disconnected from what they intend to do when they started. And so reconnecting, I mean, so much of this, I guess I tend to see everything through that lens, but so much of it is about reconnecting, that, that reconnection, that path back home.

• 1:31:30Jay Shetty?

  I love what you were saying about the iconography and how the human meshes with the iconography. And you described earlier, the

• 1:31:36Brian Chesky?

  And maybe everyone does that. I just did it in a bigger, sorry to cut, I just did it in a bigger way. Like, you could totally get how like, I and Brian Airbnb, they start to merge. But I bet you even people who don't have a giant company, who they really are, and the person they're like supposed to be are merging. And as those two things merge, you lose who you really are.

• 1:31:56Jay Shetty?

  I mean, it's method acting. It's literally method acting. It's like, we are all pretending to play a role, only to believe that that role that we pretended to be is now us and has replaced us. And it's, and it's even harder, I'll tell you why, because when you built Airbnb, it had iconography.

• 1:32:13Brian Chesky?

  Yes.

• 1:32:13Jay Shetty?

  Brian didn't ever have iconography. Like, there wasn't a, there wasn't like a mission list and a value list, like before, when Brian existed before. And so, if you were to draw the iconography of Brian, the person, not the Airbnb, I'm intrigued as to what that would look like if you started to design that.

• 1:32:36Brian Chesky?

  I see a child. I see like a, a childlike curiosity and energy and love.

• 1:32:44Brian Chesky?

  That I think I've always held on to. I also see the world like through this idea of family and community. And I think when people hear the word family, they think of like their parents, their siblings, their children. And I think I see like, you know, I asked like my co-founder Joe, I asked him like, what would Airbnb, would success be for Airbnb? He had this crazy audacious idea. He said to redefine the word family. And I, I've, I've realized that like so much of my life has been trying to do that. I see this like childlike person of curiosity and wonder that I've never left that sense of wonder, that I'm open to be vulnerable and guided by love and like treating, I, I,

• 1:33:28Brian Chesky?

  wanting to treat those around me like family. And what I mean by that is I'd try to do anything for them.

• 1:33:38Brian Chesky?

  And, and I hope, I hope that my friends, if they ever heard this, they would feel like that resonates and that's not just a pure ideal.

• 1:33:49Brian Chesky?

  I mean, that's what I, that means that's the iconography. I would hope that iconography is true to some extent. I guess as I think about it even deeper, I, I've used the word loneliness, connection and community, but maybe at some deeper level, the deepest word is family. And what bonds, bonds family is love. And like, I think that like, as families have gotten smaller and smaller, we've gotten more, more and more isolated. And if we could re-expand that word, and maybe that's like too idealistic, but like just even a little bit to your like close friends and to other people and just try to like re-expand that circle. That's kind of what I would want.

• 1:34:35Brian Chesky?

  You know, if I designed the world around me, then I better design it with other people in it.

• 1:34:40Jay Shetty?

  As you see that, do you, do you see the child or are you the child? As you visualize that.

• 1:34:47Brian Chesky?

  Yeah, it's funny. I kind of see both. I see.

• 1:34:49Jay Shetty?

  Like, are you seeing the child sitting there or are you seeing the vision through the eyes of where you would be?

• 1:34:55Brian Chesky?

  I feel like a timeless image of myself. Like, I'm like, young and old at the same time. Like, it's not just one age. I'm like, I can see the child of me, and I could also see this, like, grown up that I always, like, that is protecting. And so I have, like, both sides. The protector, offering security and bringing people together, and the child, who is vulnerable and seeks love and wants to just be open and totally curious. It's almost like, I have this image, you know, like, you're like, you sit at the family, the dinner table, where you're like, like, you're a kid, where your parents, your siblings, wherever.

• 1:35:31Brian Chesky?

  My image is that, but it's a very big table with a lot of people. And, you know, and that's not just my close family that I might have. It's, you know, maybe like, the broader people in my life that I have around me. That's, I think, the image I have. And I think that's in a space that's very well designed.

• 1:35:54Brian Chesky?

  Very well designed. And I have a design aesthetic that's like, fairly modern, but also whimsical. I don't like the cold. I don't like coldness of modernism. I like it to be like, colorful. And so, yeah.

• 1:36:08Jay Shetty?

  I saw, if you're okay with that, I want to share something that came for me. To me, the clarity is that it's not even the merger often. What you said so beautifully was like, I see my younger self and I see where I am now. And now is protecting, but the childlike is that love, that joy, that that community, the family. And it's like, they're hand in hand. Like, it's not a merger of the two. It's not an integration. It's a hand in hand.

• 1:36:32Brian Chesky?

  Oh, it's really great.

• 1:36:33Jay Shetty?

  There's a wisdom that you have today that you didn't have then. And there's a wisdom you had then that you don't have now. And it's just hand in hand and walking together.

• 1:36:40Brian Chesky?

  I've always wanted to believe that I can have the wisdom of my grandparents and the curiosity of a child.

• 1:36:45Jay Shetty?

  There you go.

• 1:36:46Brian Chesky?

  In one, that I have a foot, you know, Walt Disney, one of my other idols, used to, in the front of Disneyland, he says, here you leave the world of today and enter the world of tomorrow, yesterday, and fantasy. He said, I have a foot in the future and a foot in the past. And I think that's partly what I have. A foot in the future. And that future is one of maybe curiosity and looking forward and futurism and technology. And then I have also a foot in the past. The foot in the path is my roots. I think I oscillate between the two. You know, culture and technology, massive scale. Want to become one of the biggest in the world with like, that I desire to always be a startup and always be close knit.

• 1:37:31Brian Chesky?

  It's like these two paradoxes, competing forces.

• 1:37:37Brian Chesky?

  Yeah, and I think that that is a tension that it's, I think it's a really interesting tension. Now you're making me think about all this. Like, I'm sure I've never, some of this stuff I've never really, not only have not talked about it, some of the stuff I'm kind of never really thought about that until now. I'm just really thinking about it. One of the things when you're like, you run a giant companies, you learn scale. When you start a company, you're tiny. You have to do everything. You have to like, you know, like things you don't even think about, like you have an office, which is your apartment and you need to like buy a coffee maker and go buy the coffee and you need to like, have a name for your company and actually need to check if that name's trademarked and you gotta buy a domain name and you gotta like have a story for the company and like,

• 1:38:19Brian Chesky?

  then you've got to like, make sure you have a legal corporation, you have to have a lawyer, you gotta interview the lawyers and then you gotta like, actually decide where you're gonna make and you say, well, how do I make things? Like, and I could go down the hundred thousand things, you're in the tedious details. And then if you go on a rocket ship that I go on, 15 years later, you know, a billion and a half times has been used, you end up at some massive scale, a scale that's bigger than you've ever imagined. But as a founder, you never let go of those details. You know, it's like a founder is different than a professional manager. A professional manager never saw it small. And as a founder, not only did you see it small, you created what was small.

• 1:38:58Brian Chesky?

  And so as you see the full scale, you tend to zoom out and zoom in and zoom out and zoom in. And it's actually a really helpful skill in life.

• 1:39:10Brian Chesky?

  Whenever you need a different perspective, you can zoom in or you can zoom out. And I tend to do both. I go in and say, well, what about this? What about this? What about this? And go into the smaller and smaller detail. And then I go back to the present scale. It's like a satellite map. It's like the power is a 10. Zoom out to space, zoom in with a microscope. And that is just a way to think about things. And you're constantly doing that when you run a company. You see the big picture and you say, what does this mean? You dive right in and you zoom out. And a lot of leaders, they struggle. They can only do that medium altitude. They can't see the fullest picture. Or they get stuck and they can't access the smallest of details.

• 1:39:53Brian Chesky?

  And the entire universe exists in the smallest detail. And that's what you discover when you zoom in and zoom out. You start to realize the relationships. And it allows you to both run something large and still connect with somebody at the most intimate human level and not lose your mind along the way.

• 1:40:09Jay Shetty?

  Yeah, it's that balance between recognizing what's possible through scale, but at the same time, being able to be embracing of your own insignificance.

• 1:40:19Brian Chesky?

  Yeah.

• 1:40:19Jay Shetty?

  So you see the significance, but yet you recognize

• 1:40:22Brian Chesky?

  Yeah.

• 1:40:23Jay Shetty?

  it's insignificant.

• 1:40:24Brian Chesky?

  Yeah.

• 1:40:24Jay Shetty?

  And that paradox is where

• 1:40:25Brian Chesky?

  It's so fascinating.

• 1:40:26Jay Shetty?

  Yeah. The paradox is the only thing that's fascinating.

• 1:40:28Brian Chesky?

  Yeah.

• 1:40:29Jay Shetty?

  You know, the human mind is a paradox. All of these, everything that we see that's magical about the world is a paradox. That everything's connected, but everything's doing its own thing.

• 1:40:37Brian Chesky?

  Yes.

• 1:40:37Jay Shetty?

  Right? Like the ocean and the sun are doing their own thing, yet they're connected, yet they're doing their own thing.

• 1:40:41Brian Chesky?

  And I think the more you start to see why I want to scale, you sort of see, you're right, that more and more things are connected. But because everything's connected doesn't mean they're all the same. And the more you learn about the details of things, the more you realize how different everything is. And so you, but then you realize they're actually in some deeper way related. And that you spend the rest of your life kind of in that discovery.

• 1:41:03Jay Shetty?

  Yeah. And you know what I've observed that is the connecting force, at least up until now in my life? Is that everything that we've just talked about, everything in the universe that we see is serving uniquely. What connects it is that it's serving. The sun is serving. The water is serving. The trees are serving. The trunk of the tree, the leaves you talked about, the flowers, they're serving. Everything is giving a service.

• 1:41:26Brian Chesky?

  Everything's interdependent on everything else that we tend to have this illusion.

• 1:41:32Brian Chesky?

  That we're separate from one another. And I, I think that even like loneliness might be a, a reality, which is the way you perceive the world, but aloneness may be a illusion that you're not as alone and separate as you think you are. And I think that's a really good thing to remind yourself and that we are like so much more connected to everything else. And that I think so much of creativity is just first embracing the fact that everything is connected in some way and it's your job to discover and make connections and find relationships and similarities. And by the way, that's a great way to connect with people, to know that like, wow, what makes them so fascinating is they're really different from me in some of these ways. But what is going to bond us is that we're actually so connected.

• 1:42:15Brian Chesky?

  And there are almost no humans on this planet that you don't have some fundamental connections to. And if you don't see them, you have to keep looking. And then once you keep looking, that becomes the bond, that becomes the thing that you share between them. And how do you do that? With curiosity and interest. Fascinating. Just be fascinated all the time. And it's almost like that's contagious. If you're fascinated, I'm fascinated. Somebody once said that to me, a director who I was doing a film shoot and he said, if you're fascinated, I'm fascinated. And I'm like, well, okay, like I really do, and it's like, and so what, what do you find fascinating?

• 1:42:53Jay Shetty?

  Yeah. Yeah, I often say to people similarly that if you don't find someone interesting, it's because you're not interested.

• 1:43:00Brian Chesky?

  Yeah.

• 1:43:01Jay Shetty?

  Like you're not interested enough. There is something interesting about every person you meet.

• 1:43:03Brian Chesky?

  There is something interesting about everyone and everything. And that is what the, that is, I think, what curiosity is. And like, you know, you find the game within the game. You find like in school, like I, I think so many people in school, like they're not interested in subjects because they're abstract. But if somebody's obsessed with basketball, then teach physics through basketball, treat biology through basketball, teach history through basketball, the history of, so you just, you find something you're interested in. And I think the great thing about starting a company is I had no interest in learning about accounting. I had no abstract interest in learning about leadership and management and organization. I had no abstract interest in understanding like technical architecture, but I had the interest in how we should account for all the money we're making, what technology platform we should be on to enable Airbnb.

• 1:43:48Brian Chesky?

  And through something I was already interested in Airbnb, I was able to learn all these other things. But if I had to learn them abstractly, the way we're taught in school, I don't think anything would have stuck. And so. Airbnb became that model, this world. And I have learned almost everything through this world that I've been generally constructing, co-constructing with my coworkers and with the community. And it's just like, I like to joke that Airbnb is like the world's biggest RISD project that just never stopped. And we just kept building it and kept building it and kept building it and kept building it. And the bigger we build, the more I learn and the more I discover. And yeah, I've seen so much of the world through the creation of this really big house, so to speak.

• 1:44:32Jay Shetty?

  Yeah.

• 1:44:32Brian Chesky?

  It's pretty wild.

• 1:44:33Jay Shetty?

  It is pretty wild.

• 1:44:34Brian Chesky?

  And it's just getting started, hopefully.

• 1:44:36Jay Shetty?

  It's just getting started. Brian, this is without a doubt the most unique episode of On Purpose I think we've ever had.

• 1:44:43Brian Chesky?

  Really?

• 1:44:43Jay Shetty?

  In four years.

• 1:44:44Brian Chesky?

  No way.

• 1:44:45Jay Shetty?

  And I don't just say stuff like that. You can check with these guys. And, uh, but we end every episode with a final five. These are five questions I ask pretty much 90% of them to all guests. And these are your final five, Brian. They have to be answered in one word to one sentence maximum. And I will probably destroy that pattern, but we'll try. So Brian, these are your final five. The first question is, what is the best insight advice that you've ever heard or received or read?

• 1:45:15Brian Chesky?

  It's better to have 100 people love you than a million people that just sort of like you. And so do things that don't scale. And if you do, maybe people love something you love so much, they'll tell everyone about it and you might end up with millions of people after all. It's kind of a long sentence, but.

• 1:45:36Jay Shetty?

  It's a great sentence. It's beautiful. It's perfect. Second question, what is the worst insight advice you've ever heard, read, received, or come across?

• 1:45:45Brian Chesky?

  Anything that involves chasing status. Not because it's bad, but because it's actually a horrible way to even get it.

• 1:45:53Jay Shetty?

  Love that answer. Yeah. Question number three, how would you define your current purpose?

• 1:45:59Brian Chesky?

  To try to help bring the world together, even if it's in the end a small way.

• 1:46:06Jay Shetty?

  Question number four, if you were being remembered after you were physically gone, what would you hope to hear?

• 1:46:15Brian Chesky?

  We miss him.

• 1:46:16Jay Shetty?

  A fifth and final question, I ask this question to every guest who's ever been on the show. If you could create one law that everyone in the world had to follow, what would it be?

• 1:46:25Brian Chesky?

  Sometimes people ask me, if you could impose one thing on the world, what would it be? And I'd say, everyone would have a passport and everyone would walk in someone else's shoes. And I think if they were to do that, there'd be like such a greater awakening in the world. So maybe everyone was forced to live someone else's life and to step in someone else's shoes. And the more different, the better.

• 1:46:49Jay Shetty?

  Well said. Brian Chesky, everyone. Brian, that was, as I said, the most unique. I think it's really interesting, something that came to my mind and heart. And since this has been such an intuitive conversation, I feel I should share it. You know, in our professional life, we have business partners. But in our personal life, I don't think we often think about having human partners. And I really appreciate you dancing with me today, going there with me today, and being human partners for each other. And you definitely did that for me today. You brought out of me things I didn't know that I haven't gone to for a while. So thank you so much for inspiring me and enlightening me in so many ways. I truly had a special internal experience myself.

• 1:47:30Brian Chesky?

  Well, I think I've learned about myself through this process. It's amazing the amount of time you can go through in your life without stopping and taking a look at things. And when you do, my God, like that just changes your perspective on everything, doesn't it?

• 1:47:47Jay Shetty?

  Absolutely. Thank you so much. I'm so grateful for you.

• 1:47:50Brian Chesky?

  Well, thank you for having me today.

• 1:47:51Jay Shetty?

  Thank you so much. Such an honor, such a pleasure. And everyone who's been listening and watching, if you're with us, then make sure that you... I want you to let me know what was your favorite moment. There are so many great moments, but grab a screenshot of where you found your favorite moment so we can see all the seconds and minutes so that everyone can go listen to it. I love seeing what deeply connects and penetrates through to our community because this is all in service of you. So thank you for everyone who's been listening and watching, and thank you, Brian.

• 1:48:18Brian Chesky?

  Thank you, Jay.

• 1:48:19Jay Shetty?

  If you loved this episode, you will also love my interview with Charles Duhigg on how to hack your brain, change any habit effortlessly, and the secret to making better decisions.

• 1:48:30Speaker 05

  Look, am I hesitating on this because I'm scared of making the choice? Because I'm scared of doing the work? Or am I sitting with this because it just doesn't feel right yet?

• 1:48:40Speaker 06

  Now, more than ever, we need someone on our side. But Rob Whitman? Whitman's votes drove up costs, cut Medicaid, and risked 350,000 Virginians' health care to pay for tax breaks for himself and his donors. He's not on our side. Shannon Taylor will fight corruption, cut taxes, and bring down costs. This November, vote for Shannon Taylor. She's for us. Paid for by HMP, the House Majority PAC dot com. Not authorized by any candidate or candidate's committee.