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Jay Shetty PodcastJay Shetty Podcast

Airbnb Founder: The Number 1 Thing People Get Wrong About Happiness and Success | Brian Chesky

Today, Airbnb co-founder and CEO, Brian Chesky joins us on the podcast. In this episode, Brian is honest, vulnerable, insightful, and most of all human.

Brian CheskyguestJay Shettyhost
Sep 11, 20231h 40mWatch on YouTube

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Transcript

0:00 – 2:44

Intro

Brian Chesky 0:00 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."

Speaker 0:07 Airbnb CEO, his name is Brian Chesky. He's a badass in this business. You're worth $30 billion.

Brian Chesky 0:13 The problem with success is it tends to amplify things. No one ever told me how lonely it 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?

Jay Shetty 0:27 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.

Speaker 0:54 The best-selling author and host.

Jay Shetty 0:55 The number one health and wellness podcast.

Speaker 0:57 On Purpose with Jay Shetty.

Jay Shetty 1:01 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. In 2007, Brian and Joe Gebbia became Airbnb's first hosts. Since then, Brian has overseen Airbnb's growth to become a community of over 4 million hosts who have welcomed more than 1 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.

Brian Chesky 2:14 Well, thank you for having me.

Jay Shetty 2:15 Uh, thank you for being here.

Brian Chesky 2:15 Really excited to be here. This is awesome.

Jay Shetty 2:17 I'm, 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.

Brian Chesky 2:36 We try every day.

Jay Shetty 2:37 So congratulations. It's been a joy watching it from afar, and I'm excited to build this relationship with you.

Brian Chesky 2:42 I'm excited to talk about this.

Jay Shetty 2:43 Yeah.

2:44 – 6:05

What Makes You Happy?

Jay Shetty 2:44 Well, let's dive into it. I want to start off with my first question, which is what makes you happy today, and how does it differ from what made you happy 16 years ago?

Brian Chesky 2:55 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 with 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 to the top of the mountain? You've achieved it. And what I've realized is at th- 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..." or, "Why don't you s- 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 d- business person. You know, y- you're, 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. N- 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. 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 gonna 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, 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, 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 turn, 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. Like, how much more is gonna make you happy? And so just doing things I love with people I care about, that's what makes me happy today.

Jay Shetty 5:54 That's beautiful. That's... I, I can see that it's true for you too. I, 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

6:05 – 9:03

The Journey Of Starting A Business

Jay Shetty 6:05 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.

Brian Chesky 6:28 Right.

Jay Shetty 6:29 And it sounds like you've been excavating that internal part for some time.

Brian Chesky 6:34 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 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, and it's like 1,000 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 also 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 gonna actually manifest in, like, not actually dealing with things. If you can't... If you're not decisive, there's gonna be an element of bureaucracy. If you, like, get overwhelmed and you get paralyzed, there's gonna be inaction in the company. And so you learn so much about yourself. And I, through this process, I probably learned more about myself than I even have about business, and it's been an incredible journey. And, um, yeah, it's, it's like incredible lessons. And, and the company's like a mirror about you, right? Like, when you see a company, it's like I 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 1,000 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. A company is like that, but it's like 100,000 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 the, what they... And, and that's the thing that's, like, so crazy.

9:03 – 13:40

Founding A Company With Friends

Jay Shetty 9:03 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.

Brian Chesky 9:14 Yeah.

Jay Shetty 9:15 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 change for 16 years, but here you are still building it together.

Brian Chesky 9:40 Think about how many stories you 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 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, and 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 gonna hire, what we're gonna call, what markets we're gonna go into, what's the prioritization, like, who we're gonna raise money for. 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 gonna supersede our friendship and our relationship, that we're never gonna 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. 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 at the right time with the right idea." And I say, "Well, maybe," but there's something I was much luckier about. And what I was most lucky about, w- what, 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 test. 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 gonna find people that are perfect complements to you. I'd say a couple things. Number one, you want to have a team with people that you are friends with or could see yourself becoming friends with, that you have a deep love and respect for, that you're gonna 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 in the same belief system. If you have different values, eventually those are gonna 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 on 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, Joe and Nate, you know, were included in things. And th- I wanted to always make sure that people referred to us together. We thought of us as a, uh, as a, as a unit. When we-- When I, like, went public, you write a founder's letter, and a lot of people write the 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 and they're not fighting, and they have a mutual love and respect for one another, that's gonna permeate the company, just like it permeates the health of a child. And Joe and I, and I [chuckles] kind of thought of ourselves as parents and the company as a child. I'd never have 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 o- respect for one another, that is gonna be a role m- a model that other people throughout the organization are gonna copy. And that's what I've learned from that.

Jay Shetty 13:39 I think, I think

13:40 – 16:17

Your Success Depends On Others

Jay Shetty 13:40 what you're saying is very, very true, and it's remarkable that you've been able to hold onto that. I mean, I remember just comparing it to something very minuscule, 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 gonna fight over girls."

Brian Chesky 13:53 Yeah.

Jay Shetty 13:53 "Like, we're not gonna fight over women."

Brian Chesky 13:55 Yeah.

Jay Shetty 13:55 And then there'd always be the guy who-

Brian Chesky 13:56 Yeah

Jay Shetty 13:56 ... who trades the friendship-

Brian Chesky 13:57 Yeah

Jay Shetty 13:58 ... for, for a girl, and then, like, the whole thing's lost.

Brian Chesky 14:00 And that's a short-term decision.

Jay Shetty 14:01 Yeah, it's a very-

Brian Chesky 14:02 And, and-- And I understand why people make short-term decisions. They make trade-offs. They wanna 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 with me, and, like, you know, like being the only one in power is actually quite lonely. Having been in that, a little bit of that position, I 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 to be able to share that with Joe and Nate, and now to be able to share that with the people that I get 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'd had 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 a, like, a giant Fortune 500 company. Did over sixty billion dollars last year in, 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. 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. And that's what I got with Joe and Nate, and I think I believed in what I think

16:17 – 18:27

The Vision That Started Airbnb

Brian Chesky 16:17 I saw. They saw potential in me. What I saw maybe was potential in this idea.

Jay Shetty 16:23 Mm.

Brian Chesky 16:24 That if people could experience what we experienced that first weekend when we hosted 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 than 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 sociolo- sociological changes. We can all imagine technological changes. We can imagine things getting bigger, faster, but it's hard to imagine us living differently.

Jay Shetty 16:54 Mm.

Brian Chesky 16:55 And I don't think that we were visionaries per se. 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 the last fifteen years, one and a half billion people, um, 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 LA 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 ninety-nine percent the same. I think that Joe and Nate believed in me and my potential to, to be in this company. I think we collectively believe 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

Jay Shetty 18:25 Mm-hmm. How special. I mean,

18:27 – 20:19

People Are 99% The Same

Jay Shetty 18:27 that's-- That is something that I definitely got a mini version experience of. I just finished a 40-city world tour-

Brian Chesky 18:35 Really?

Jay Shetty 18:35 ... for my second book, and we probably met about 100,000 people on the way out of the vans

Brian Chesky 18:41 Oh my God

Jay Shetty 18:42 And much, much smaller than the one billion, uh, bookings. But I would agree with those two sentiments so strongly. They were 99% the same, and people are o- overall good.

Brian Chesky 18:55 If people believed everyone was basically the same, then how could you hate someone else? 'Cause to hate someone else is to hate yourself.

Jay Shetty 19:01 Mm-hmm.

Brian Chesky 19:01 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.

Jay Shetty 19:20 Mm-hmm.

Brian Chesky 19:21 And I think that the best way to understand that somebody is similar to you is to walk in their shoes-

Jay Shetty 19:27 Mm-hmm

Brian Chesky 19:27 ... 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. 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 a YouTube comment section. But if it's hard to live with somebody or to walk in their shoes and not change your mind, how, how could you not change your mind about something?

Jay Shetty 19:57 Mm.

Brian Chesky 19:57 '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 pos- How'd you even have your opinions in the first place?

Jay Shetty 20:08 Mm.

Brian Chesky 20:08 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.

20:19 – 26:37

Our Human Desire Is To Belong

Jay Shetty 20:19 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 wanna be lonely at the end of a journey. You never wanna 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, 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?

Brian Chesky 21:16 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. If I were to think about my journey with loneliness, I think I grew up as a little bit of a lonely, isolated kid. Um, I was interested in art and design, um, but I also played sports. I didn't really feel like I fit in growing up. I, um, 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.

Jay Shetty 21:57 Even as a hockey player?

Brian Chesky 21:58 Even, oh, as a hockey player at an art school, like, kind of like-

Jay Shetty 22:01 [laughs]

Brian Chesky 22:01 I went to, like, a military, like, private school. Uh, and then I went to a art college, and, like, I kinda had a foot in each and not fully, like, like... And I would-- I had, you know, maybe issues with authority. I didn't really fit in. Um, it turned out to be a huge benefit to being a tech founder. But of course, who doesn't wanna fit in, uh, 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, 5,800, 150 people, and to not be part of that 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. 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 25, 20-- turning 26, I s- started with my two co-founders, and we became the family. We became a family that I hadn't had for 10 years since I really-- 10 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 lived together. We all, like, waked up-- woke up around the same time, around 8:00 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. 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, 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, a sil- 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. And no one ever told me how lonely it 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, uh, 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 twenty-four/seven, you know, like, 16, 18 hours a day for an entire year of 2020. I, you know, help with a team. 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 $100 billion valuation. And remember, if you told me, like, a million dollars is more money I ever imagined growing up. My parents are social workers. I- that- it was, like, an unfathomable amount of money. And I remember after going public is like, oh my God, there's this, like, amazing exultation. It was amazing. Like, I'd gone to the m- 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, and I just don't really have m- 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 kinda re- went down the list and I said, "When's the last time I talked to these people?" And I realized that m- almost every single person on the list, if I were to ping, I'd have to catch them up on my life. I couldn't just dive into something 'cause I had not maintained those relationships. And it was just something that, like, started, you know... And I, I, I started noticing I started feeling more isolated. I would have more negative ruminations and stuff, and I didn't know at the time that I was lo- isol- lonely. I knew I was isolated, but I didn't know that that also meant loneliness. And I thought, I, I have all these people around me. How could I possibly feel this way?

26:37 – 28:29

On Forging An Eye-Opening Friendship With Former President Barak Obama

Brian Chesky 26:37 And there were a couple people that, like, entered my life that, like, gave, gave me some awareness and consciousness, one at the p- deeply personal level and one more at the professional level. At the personal level, um, 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. Um, and then he, um, 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 kinda told me, like-- I kinda 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. 'Cause 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. So one of the most important things I decided to do was renew the relationships that were in that invite list of 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. 'Cause 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 spent-- started spending more time with my sister and other people in my life. I ended up getting, like, a dog, a golden retriever, um, named Sophie Supernova. And the

28:29 – 34:59

The Silent Killer: Loneliness

Brian Chesky 28:29 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 n- mon- need money for, and I didn't even need to have success to achieve. Relationships, many of them I had before I started. You know, the, as you know, I think you had Robert Waldinger on your show, and, you know, he, um, I actually met him last week for the first time. He is, as people listening here 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, they 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.

Jay Shetty 29:45 Exactly.

Brian Chesky 29:46 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 wanna 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 as, 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, um, is the now and former surgeon general of the United States, Dr. Vivek Murthy. We hired him during the pandemic because a lot of people were afraid to, like, you know, um, 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 kinda 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 can take 15 years off your life." And not only that, but about half of Americans are lonely. Um, 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... I- maybe 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, the Earth, and that loneliness is disconnection from each other, 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 and started asking, well, Airbnb's 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 'cause most of them didn't even live in the same city as me. I started realizing, you know, when you get to my age, you're 41, you have a public company, you have a couple 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 wanna... of course, I wanna, 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, and I, I, I want all that to happen, but that can't be enough-

Jay Shetty 33:05 Mm

Brian Chesky 33:05 ... that there's gotta 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 gotta be something greater. And I have, like, the, one of the biggest canvases in the world of any designer ever, and what I wanna design is not products, I wanna design connections between people. 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 wanna design for ourselves. 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.

Jay Shetty 34:17 Mm-hmm.

Brian Chesky 34:17 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. 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.

Jay Shetty 34:48 Thank you for coming to my TED Talk. [laughs]

Brian Chesky 34:50 [laughs]

Jay Shetty 34:50 That was, like... That was a, that was a masterclass on loneliness. Uh, and I, and I mean that, and it's beautiful to see how it can

34:59 – 40:15

The Importance Of Connection

Jay Shetty 34:59 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-

Brian Chesky 35:13 They're awesome

Jay Shetty 35:13 ... 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, "Eh, it wasn't it," throw it away-

Brian Chesky 35:23 Right

Jay Shetty 35:23 ... 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."

Brian Chesky 35:30 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.

Jay Shetty 35:39 Yes.

Brian Chesky 35:39 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 gonna fully do that.

Jay Shetty 35:47 Mm.

Brian Chesky 35:47 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 in giving to other people... You know, Steve Jobs, one of my heroes, used to say-

Jay Shetty 35:58 Mine too

Brian Chesky 35:58 ... um, oh, I get to work now with Jony Ive.

Jay Shetty 36:00 Wow.

Brian Chesky 36:00 He started a firm called LoveFrom, 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 the fundamental soul of a man-made creation that reveals itself through subsequent layers. 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.

Jay Shetty 36:39 Mm.

Brian Chesky 36:40 I just wanna do the thing to the purest, best of my ability, and to feel like I give to others. And this is the other thing is it's 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. I was-- parents are social workers. 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.

Jay Shetty 37:23 Mm-hmm.

Brian Chesky 37:24 And I think, ultimately, like, I think me as a l- I as a leader, I never saw someone 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 Rhode Island School of 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 board- room? We can run the boardroom."

Jay Shetty 37:46 Mm-hmm.

Brian Chesky 37:47 But of course, like, designers, the people never thought started companies. And there's an old saying, "Art is a question of the problem in 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 Air Bed and Breakfast, air beds instead of beds for Air Bed and Breakfast. And, 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, and 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. And I find that a lot of companies, they get really cold as they get big, that when 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're, like, putting your love into it. You're intuitive. No startup is data-oriented, 'cause there is no data. If you have an idea, there is no data. So you go off your intuition. You do something 'cause 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, identify as creative? Almost none. Okay, how many boards? There's 12 members on average of a Fortune 500 board. That's, like, probably 6,000 member-- so the Fortune 500. How many boards have, like, creative people? Not, 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, a company with, like, a sense of a spirit-

Jay Shetty 39:53 Mm-hmm

Brian Chesky 39:53 ... a, a sense-- You know, our logo is like an inverted heart. It was meant to be this idea almost of this, like, beating heart-

Jay Shetty 40:02 Mm

Brian Chesky 40:02 ... 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.

Jay Shetty 40:10 But you can.

Brian Chesky 40:11 But we can, or we'll die trying.

Jay Shetty 40:12 [laughs] You've, you've sparked a lot

40:15 – 42:06

The Difference Between Loneliness And Solitude

Jay Shetty 40:15 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 f- the first thing that came to mind is it's really incr- There's a beautiful statement by Paul Tillich, who's a, 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.

Brian Chesky 40:41 Oh, yeah.

Jay Shetty 40:41 And when you said we're disconnected from the earth, we're disconnected from each other, but really we're disconnected from ourselves-

Brian Chesky 40:46 Yes

Jay Shetty 40:46 ... it's because of a lack of solitude.

Brian Chesky 40:48 Yes.

Jay Shetty 40:49 And when I lived as a monk, being comfortable being alone was the first lesson of the day-

Brian Chesky 40:54 Wow

Jay Shetty 40:54 ... because the idea was that if you can-

Brian Chesky 40:56 And how do you learn how to do that?

Jay Shetty 40:57 Well, there's, there's many technique, techniques. One of the first techniques is if you just sit with yourself for long enough, [laughs] you start to see so much in yourself that what you-- 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 incomp- and complexity.

Brian Chesky 41:30 There, there's a great, um-- One of the late great mythologists of the 20th century you probably know is Joseph Campbell.

Jay Shetty 41:36 Of course. I love Joseph Campbell.

Brian Chesky 41:36 He had this great quote, "The cave you fear to enter lies the treasure that you seek."

Jay Shetty 41:42 Mm-hmm.

Brian Chesky 41:42 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.

Jay Shetty 41:51 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

42:06 – 49:49

Lessons From Steve Jobs

Jay Shetty 42:06 Steve is a, is a hero of yours. Same with me. I feel like I've studied everything he's ever said or written.

Brian Chesky 42:11 Yeah.

Jay Shetty 42:11 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. 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."

Brian Chesky 42:51 Wow.

Jay Shetty 42:52 For a-- "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.

Brian Chesky 43:04 Oh, wow.

Jay Shetty 43:05 And what I-

Brian Chesky 43:05 I didn't know that story.

Jay Shetty 43:06 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.

Brian Chesky 43:17 Yeah.

Jay Shetty 43:17 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.

Brian Chesky 43:46 Mm.

Jay Shetty 43:46 Whereas people who had networks who were correlated were less likely to be creative and entrepreneurial.

Brian Chesky 43:51 There were fewer unknown discoveries.

Jay Shetty 43:53 Exactly.

Brian Chesky 43:53 And I, 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 had a cross-enrollment product development program. Then I went to Los Angeles as an, a designer at a firm. Then I s- went to Silicon Valley with very little and, like, th- 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.

Jay Shetty 44:31 Mm-hmm.

Brian Chesky 44:31 And every single one of them I've used, every single experience, but I could never have reversed engineered how to get there. And it is amazing that, like, you know, Steve used to say the best engineers were also poets.

Jay Shetty 44:44 Mm-hmm.

Brian Chesky 44:45 And he was really saying that, like, creativity is about connecting dots. It's about having disparate experiences and you bringing them to- together, and if you haven't had a lot of different experiences, if you d- aren't very multidisciplinary, you're not gonna be a... I mean, Einstein was, like, a violinist. Right? I think a lot of the greatest scientists have leaps of the imagination. They're not just em- using empirical information. And a lot of the be- 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. I mean, we need more creativity.

Jay Shetty 45:20 Mm-hmm.

Brian Chesky 45:20 You know, whenever you see two bad options, you don't like it-

Jay Shetty 45:23 [laughs]

Brian Chesky 45:23 ... the right answer is the third option.

Jay Shetty 45:24 Yeah.

Brian Chesky 45:25 The third option is one you haven't come up with yet that requires novel-

Jay Shetty 45:28 [laughs]

Brian Chesky 45:28 ... innovative, imaginative thinking. Where does it even come from?

Jay Shetty 45:31 Mm-hmm.

Brian Chesky 45:31 Where does creativity come from? If creativity, you know, but I, I don't know if Einstein ever said this, but there's a quote attributed to him that is that, "Logic can take you to, from A to Z, but imagination can take you anywhere."

Jay Shetty 45:43 Mm.

Brian Chesky 45:44 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 f- first following your passion, but following your curiosity with a deep 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.

Jay Shetty 46:17 Mm-hmm.

Brian Chesky 46:18 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-

Jay Shetty 46:29 [laughs]

Brian Chesky 46:30 ... 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 weren't social workers, I don't think I would have had this focus on service 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 gonna singer, to be a musician. I did not think I was gonna be an astronaut, politician. And so I'm like, "I don't know who I'm gonna 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-

Jay Shetty 47:10 Yeah

Brian Chesky 47:10 ... 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, and I thought, "One day I will 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, but it, 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 Gi- you mentioned The Giving Pledge. If you asked my teachers in high school to predict which of their students would be a signatory of The Giving Pledge, I do not think I would have been the top of their list. I f- don't think that takes anything away from the teachers. I think it just means that maybe that potential's 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. 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, 100,000 decisions later with enough resilience, creativity, curiosity, and determination, you wake up one day and you're like, "Oh my God, look where I am now."

Jay Shetty 48:26 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.

Brian Chesky 48:39 Yes.

Jay Shetty 48:40 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 the, 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.

Brian Chesky 49:02 Wow.

Jay Shetty 49:02 Those were 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- 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

Brian Chesky 49:30 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-

Jay Shetty 49:44 Correct. It's the and

Brian Chesky 49:45 ... has made, has made you who you are. Not one of them, but all of them. And I think

49:49 – 51:10

Try More Things, Have More Experiences & Avoid Seeking Status

Brian Chesky 49:49 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 in the future.

Jay Shetty 50:01 [laughs]

Brian Chesky 50:02 Like, growing up, status to me was, like, um, I don't know, it was, like, being an investment banker or something-

Jay Shetty 50:08 Yeah, same. Same

Brian Chesky 50:08 ... 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, but you tend to be good at things you're interested in. You should th- seek, seek out whatever you're curious about, whatever you're interested in, and then you want to get to the fr- a frontier in some way. 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 s- 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 a 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 e- 'Cause y- anyone can do it at any scale, you know, and you can do it in your humble way, like, on the side or something small, or you can do it in a really big way. But it feels the same, no matter what the scale.

Jay Shetty 51:06 You just told us what you'd say to your younger self.

51:10 – 52:36

What Would Your Younger Self Tell You Now?

Jay Shetty 51:10 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"?

Brian Chesky 51:21 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 Meet My Friends, I said, "This will be huge. One day thousands of people will do this." Like, that was my s- 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 c- my college self, did not think I could run, like, a Fortune 500 company, you know... You know, for, for every $1,500 spent in the world, $1 spent on Airbnb. Did I think I could lead an organization that's facilitating that? No, I did not think of it. And so that would be probably the thing I would be, like, surprised in a very positive way.

Jay Shetty 52:10 Mm-hmm.

Brian Chesky 52:10 But the other thing I would probably say is, "Wow, I'm 41 years old and I s- 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 l- looked at my life now or my recent life and identified a little bit of

52:36 – 56:10

Avoid The Biggest Thing People Regret

Brian Chesky 52:36 isolation. And I think the lesson is a couple 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, 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 time, just repeating ourselves, and you just compulsively just keep doing something. And, like, many people have addictions, and I probably had one, and it was probably work. And, um, and I think I'd have to, I would hope my childhood self would rem- 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.

Jay Shetty 53:32 Thank you for that. Thank you for opening up and going there.

Brian Chesky 53:34 Yeah.

Jay Shetty 53:34 And I felt that. W- what is a thought that you say you have too often?

Brian Chesky 53:39 I wonder what they'll think. Speaking of Dr. Waldinger, Robert Waldinger-

Jay Shetty 53:43 I love Robert. Yeah, he's a good friend.

Brian Chesky 53:44 But I m- met him last week for the first time, and you've had him on your show, right?

Jay Shetty 53:47 Yeah. We've spent a lot of time together. I love him.

Brian Chesky 53:49 Something he told me last week that really stood out to me, he said, "One of the biggest regrets that people have in their life is having lived their life 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 'cause you have to fit in. 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 mis- 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.

Jay Shetty 54:22 Sure.

Brian Chesky 54:22 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, and maybe, just maybe, the person that most matters what I th- what they think is yourself, right? That you just listen to your own voice, not other voices. And I j- I think if I can do that, w- you know, artists will call it the 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. G- And the crazy thing is the more success you get, the more you start kind of performing for an audience.

Jay Shetty 55:06 Mm.

Brian Chesky 55:07 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.

Jay Shetty 55:16 Mm.

Brian Chesky 55:16 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.

Jay Shetty 55:26 Mm.

Brian Chesky 55:26 I need to be careful about changing that brand. It stands for something. And yet I, as a person, am 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- struggle with because I know a part of me, I think I'm like a people pleaser, and one of my ch- challenges historically be is, like, some people, like, I'm like, I don't always like interpersonal conflict. I like to appease people and 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.

Jay Shetty 56:09 I want to just

56:10 – 58:21

Being Misunderstood Is Ok

Jay Shetty 56:10 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 we're 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, and you were-

Brian Chesky 56:31 Thank God.

Jay Shetty 56:32 Yeah.

Brian Chesky 56:33 Thank God. You know why? When I f- when we first came with 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 vi- we call it the vision for a reason. 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 it 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.

Jay Shetty 57:36 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 it was... 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."

Brian Chesky 57:59 Oh.

Jay Shetty 58:00 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.

Brian Chesky 58:10 Yes.

Jay Shetty 58:10 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-

Brian Chesky 58:18 Totally

Jay Shetty 58:18 ... how will you ever know? What, what do you think

58:21 – 1:01:03

How To Understand Who You Are

Jay Shetty 58:21 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?

Brian Chesky 58:30 I think that we tend to have an outdated image of ourselves.

Jay Shetty 58:33 Mm-hmm.

Brian Chesky 58:34 And that makes sense, right? Like think about it. 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.

Jay Shetty 58:43 Mm-hmm.

Brian Chesky 58:44 And so I still see myself a little bit like that person. And people s- most people see me today, and a lot of people are gonna 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, you, 'cause 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. 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.

Jay Shetty 59:29 Mm-hmm.

Brian Chesky 59:30 Um, 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 [snaps finger] 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.

Jay Shetty 59:52 Mm-hmm.

Brian Chesky 59:52 And it turns out that success and status h- to some extent have benefits and, you know, but it, it's not, it's certainly, to say it's not everything is 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, m- I almost feel like in a way my life's just beginning. And so it's just beginning, and 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?

Jay Shetty 1:00:28 Mm-hmm.

Brian Chesky 1:00:28 Like, is this my story or is this, is this the end of the s- the middle of the story or the beginning of the story?

Jay Shetty 1:00:33 Mm.

Brian Chesky 1:00:33 And what am I meant to do next? And I'm, I'm kind of learning a lot more about myself every year.

Jay Shetty 1:00:39 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 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?

Brian Chesky 1:00:57 Right.

Jay Shetty 1:00:57 Like, how unmeaningful and unfulfilling would it be? And the fact that you're asking those questions at this point-

1:01:03 – 1:03:46

How Do You Want To Be Remembered?

Brian Chesky 1:01:03 Maybe one other thing can I ask?

Jay Shetty 1:01:04 Please. Oh, of course. You can add whatever you want.

Brian Chesky 1:01:06 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 cri- how do I want to be remembered? Even if no one will remember me, and I think anyone can do that. How do you want to be remembered by history, even if it's just a dev- intellectual device? 'Cause maybe not a lot of people will remember. That's okay, but live your life as if you'd be remembered. And what I realized is 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?

Jay Shetty 1:02:12 Mm.

Brian Chesky 1:02:12 And maybe that is the other version of my question in my life. At this point, you know, how can I help? With everything I have that... I mean, I've, 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? And I, I hope that what I do provides me happiness.

Jay Shetty 1:02:37 Mm.

Brian Chesky 1:02:37 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 cliché, 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.

Jay Shetty 1:02:49 Mm.

Brian Chesky 1:02:49 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.

Jay Shetty 1:03:00 Mm.

Brian Chesky 1:03:00 And the real joy is seeing them use it.

Jay Shetty 1:03:03 Absolutely. I think, uh, 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, the act of-

Brian Chesky 1:03:16 Interesting, yeah

Jay Shetty 1:03:17 ... and it was so counterintuitive to everything I'd learned growing up in London because it was always 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 ha- when anyone gets to a point of getting everything, all they can do is give it away-

Brian Chesky 1:03:37 Yes

Jay Shetty 1:03:38 ... in the right- in a way that fuels-

Brian Chesky 1:03:39 Yes

Jay Shetty 1:03:39 ... them to a mission that is aligned with their purpose, not just, not just, you know, wherever it goes.

Brian Chesky 1:03:45 Exactly.

Jay Shetty 1:03:45 But in a meaningful

1:03:46 – 1:09:36

Work Can Be An Addiction

Jay Shetty 1:03:46 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.

Brian Chesky 1:03:56 Yeah, totally.

Jay Shetty 1:03:57 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?

Brian Chesky 1:04:14 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 just incredible and positive to a point. But if you're not careful, it can become all-consuming.

Jay Shetty 1:04:45 Mm.

Brian Chesky 1:04:46 And the thing about a tech company or a star- a startup is, like... It's like imagine you, you, like, again, you have a three-person band that's now a 30,000-person band or, you know, or a 3 million pers- It just, it, there's always more you can do. 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.

Jay Shetty 1:05:16 Mm.

Brian Chesky 1:05:17 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 ch- do anything differently?

Jay Shetty 1:05:27 Mm.

Brian Chesky 1:05:28 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 I, and having that. And so I think it's just old habits and habits that have been rewarded, so but you gotta be very careful about those habits.

Jay Shetty 1:05:50 Mm.

Brian Chesky 1:05:51 I think that, I think that's what it is, and I also just... Yeah, I don't know. What do you think?

Jay Shetty 1:05:56 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-

Brian Chesky 1:06:02 Yeah

Jay Shetty 1:06:02 ... 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?

Brian Chesky 1:06:17 I think that's a big insight.

Jay Shetty 1:06:19 Yeah.

Brian Chesky 1:06:19 And maybe that's what I'm still trying to discover.

Jay Shetty 1:06:21 Yeah. I would say that you sound so clear-

Brian Chesky 1:06:23 Yeah

Jay Shetty 1:06:23 ... that if you actually had clarity, then I don't think it would be hard.

Brian Chesky 1:06:27 Yeah.

Jay Shetty 1:06:27 But it's hard to have clar- that's the hard, the hardest thing in life-

Brian Chesky 1:06:30 The hardest thing is to have clarity

Jay Shetty 1:06:30 ... is to have clarity.

Brian Chesky 1:06:31 That's a good point.

Jay Shetty 1:06:32 And so when you have clarity, it will be so much more easier for you to create. You can't create something if you don't have clarity.

Brian Chesky 1:06:37 That's a great point.

Jay Shetty 1:06:38 And so that would be my-

Brian Chesky 1:06:39 Yeah, I love that

Jay Shetty 1:06:40 ... hypothesis, at least. And that's what I was gonna ask you, my, what at least are those sprinklings of those clues? Let's, let's go with that word. What is, 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.

Brian Chesky 1:07:06 Yeah.

Jay Shetty 1:07:06 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?

Brian Chesky 1:07:13 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, 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.

Jay Shetty 1:07:55 Mm.

Brian Chesky 1:07:56 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 a intense curiosity. I was drawn to certain types of people. Um, and I had action. You know, it's like i- if you can't follow your passion, you follow your curiosity. Where does it take you? And, you know, like, you're not gonna start a company by, like, never, like, starting, and you're not gonna build a personal life you're, you want by not starting either. And so you just go on that journey, and you w- you will, you will... I think you will find what you want if you start and you keep moving.

Jay Shetty 1:08:40 Yeah, that feels right.

Brian Chesky 1:08:42 Something like that.

Jay Shetty 1:08:42 I, 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-

Brian Chesky 1:08:51 Yeah

Jay Shetty 1:08:52 ... into the future because-

Brian Chesky 1:08:53 No, that's great

Jay Shetty 1:08:54 ... 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-

Brian Chesky 1:09:03 Right

Jay Shetty 1:09:03 ... but that each one of your experiences-

Brian Chesky 1:09:05 Totally

Jay Shetty 1:09:06 ... has, has made you make better decisions.

Brian Chesky 1:09:07 And I think that the, 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.

Jay Shetty 1:09:20 Yeah.

Brian Chesky 1:09:20 And that would be fu- be fun to check in in a handful of years and see what played out.

Jay Shetty 1:09:24 Yeah. Yeah, definitely. Definitely. And it's so, it's so interesting that you keep quoting this. It, it... I've never met someone who loves quotes as much as I do, so it's, [laughs] uh, it's fun hearing them back from you and how they've played out in your life. What, what,

1:09:36 – 1:11:47

What Keeps You Up At Night?

Jay Shetty 1:09:36 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?

Brian Chesky 1:09:44 I don't know if I sleep that well, and I... Not to use another quote, but-

Jay Shetty 1:09:49 [laughs]

Brian Chesky 1:09:49 ... Pablo Casals 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.

Jay Shetty 1:09:55 Mm.

Brian Chesky 1:09:55 What keeps me up at night is... You know, like, like, people ask me in the professional context, "So what keeps you up at night at 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. 2009, Airbnb takes off. So, so we start 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 from anything I ever intended to start.

Jay Shetty 1:10:30 Mm.

Brian Chesky 1:10:31 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 Bolinas, 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 w- the company we set out to start is unrecognizable what 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. Cost is rising. Growth is slowing." It, it's starting to feel like a corporation.

Jay Shetty 1:11:00 Mm.

Brian Chesky 1:11:02 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.

Jay Shetty 1:11:12 Mm.

Brian Chesky 1:11:12 And that's, like, a really bad time to do that. But I had this image in my head of this kinda company that I wanna 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 a service, but a community. I was starting to come to the 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

1:11:47 – 1:14:51

How Airbnb Navigated The Covid-19 Pandemic

Brian Chesky 1:11:47 in February 2020 that our China business has collapsed by 80% because this thing called COVID. We're like, "What's COVID?" 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 have today. There's something about almost losing everything, and everything I had, I, 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 thin- percent 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 Airbnb to exist." And you say, "Why?" And they tell you, as if they're giving the eulogy before you're even dead, and how they, how you want to be remembered. And you start to ask yourself, "I don't know what's gonna happen, but how do I want to be remembered?" And at that point, we stepped into action, and we basically rebuilt the company from ground up. And this is to, 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 Jony Ive, who was, um, 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, um, I remember one time, I remember I went to Steve's house. I never met him, but, and, and I saw these books on the shelf from Robert Oppenheimer, and I asked his, like, wife, like, "What is with the Robert Oppenheimer books?" But as I started studying, I realized that- It was this idea that you, almost like Robert Keppen and 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 sun of a solar system, but your job is to like emit f- light and bring decision-making in to pull in this 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. Creative and analytical. Technology and humanities. That we'd have one flow. We wouldn't be metrics-oriented, we'd be basically idea-oriented, and we'd measure the results in that we would just... just really specifically ran a company. And that was basically the way I found ourselves out of a crisis. And so, so the lesson of the story is through that, I was able to get a lot of clarity-

Jay Shetty 1:14:28 Mm

Brian Chesky 1:14:28 ... through this crisis. I w- 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.

Jay Shetty 1:14:40 Yeah. Uh, that, that, that's exactly where I think we're headed, that you have, you have an opportunity to avoid the crisis-

Brian Chesky 1:14:46 Yes

Jay Shetty 1:14:47 ... in order to not be in that.

Brian Chesky 1:14:48 Not everyone needs that crisis.

Jay Shetty 1:14:49 No, you don't. It

1:14:51 – 1:17:52

How Do You Process Your Thoughts and Ideas?

Jay Shetty 1:14:51 sounds like, do you s- do you still, when you present ideas, they're so visual, you see them.

Brian Chesky 1:14:56 Totally.

Jay Shetty 1:14:56 I feel like you can see everything-

Brian Chesky 1:14:57 Yes

Jay Shetty 1:14:57 ... when you're talking about it, and I can, I can see it with you. Like, I, I feel like-

Brian Chesky 1:15:00 Everything in my head-

Jay Shetty 1:15:01 Yeah

Brian Chesky 1:15:02 ... 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 a, 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. 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 o- 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.

Jay Shetty 1:16:13 And do you see yourself in that, or is that happening and you're observing it?

Brian Chesky 1:16:18 You know, you might have 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. Like, you know, and that's kind of what the pandemic was. I ki- I described it almost as like a monastery [laughs]

Jay Shetty 1:17:07 [laughs]

Brian Chesky 1:17:07 If it w- except with Zoom. [laughs]

Jay Shetty 1:17:09 [laughs]

Brian Chesky 1:17:10 But if, but if you didn't know I was on Zoom, you'd just think I was meditating all day, right?

Jay Shetty 1:17:14 Yeah.

Brian Chesky 1:17:14 Like, I'd just be sitting in one chair.

Jay Shetty 1:17:16 Yeah.

Brian Chesky 1:17:16 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 design 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.

Jay Shetty 1:17:45 Wow. [laughs]

Brian Chesky 1:17:47 I'm just kind of... You're making me think of all this now.

Jay Shetty 1:17:50 You're making me think too.

Brian Chesky 1:17:51 [laughs]

Jay Shetty 1:17:51 I love it.

1:17:52 – 1:20:53

Finding Purpose And Clarity In Life

Jay Shetty 1:17:52 No, and, 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.

Brian Chesky 1:18:08 Yeah.

Jay Shetty 1:18:08 And that-

Brian Chesky 1:18:08 Sometimes people don't know why they're doing it.

Jay Shetty 1:18:10 Correct.

Brian Chesky 1:18:11 They, they started it for a reason. Maybe the reason was extrinsic, "I want to be rich and successful," but 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?"

Jay Shetty 1:18:25 Mm.

Brian Chesky 1:18:26 And you know the number of people that forgot why they're doing it?

Jay Shetty 1:18:30 Mm.

Brian Chesky 1:18:31 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.

Jay Shetty 1:18:39 Mm.

Brian Chesky 1:18:40 And that's when you don't look inside yourself.

Jay Shetty 1:18:42 Mm.

Brian Chesky 1:18:43 And if you're not careful, you will basically be on a super highway going somewhere not knowing why you're going there, and you wa- may wake up and end up in a destination that wasn't where you intended.

Jay Shetty 1:18:55 Mm-hmm.

Brian Chesky 1:18:55 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 we'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, 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. The problem is we don't know what we want maybe, or we, we pursue things we 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

Jay Shetty 1:19:54 Mm

Brian Chesky 1:19:55 But in a weird way, they also seem like the most possible to change. And so that, that's something that I've, 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, and you can get fused by appeasing people. And you... Like, the-- I think that happened to me. 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.

Jay Shetty 1:20:35 Mm.

Brian Chesky 1:20:36 A lot of leaders get confused, and I totally see how that happens. Um, and I think finding your way back home is key.

Jay Shetty 1:20:44 I- I would be intrigued to see if you closed your eyes now or, or whenever you chose to, to see what you saw

1:20:53 – 1:24:32

You Can Lose Yourself While Pursuing Success

Jay Shetty 1:20:53 when you looked at your personal life. You're talking about your professional life as being all these thousands of decisions moving down.

Brian Chesky 1:20:58 And you say like, like kind of that period of self-reflection, right?

Jay Shetty 1:21:01 Yeah. Like-

Brian Chesky 1:21:02 I think I saw somebody who was kind of almost punishing myself and romanticizing suffering because I thought in, in some extent I maybe believed that I was gonna 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 kinda 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 am I Airbnb? And like, you know, like they get really... One is an icon. That's a noun and verb, you know, is ubiquitously around the world, and 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. It had a face. It was 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 famous, I mean iconography.

Jay Shetty 1:22:14 Mm.

Brian Chesky 1:22:15 Icon is short for an iconography, and iconography is for, for a symbol for something. And of course people are much more than symbols. And I started seeing that. I started becoming an, a symbol and a thing, and I stopped listening to myself. And, 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 and, uh, but no one gives you pressure for yourself and your personal life.

Jay Shetty 1:22:45 Mm.

Brian Chesky 1:22:45 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-

Jay Shetty 1:23:05 Mm

Brian Chesky 1:23:05 ... 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 live in that world.

Jay Shetty 1:23:14 Mm-hmm.

Brian Chesky 1:23:15 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 intended doing 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.

Jay Shetty 1:23:34 Mm.

Brian Chesky 1:23:34 That, that reconnection, that path back home.

Jay Shetty 1:23:37 I love what you were saying about the iconography and how the human meshes with the iconography, and you described earlier the iconog-

Brian Chesky 1:23:43 And maybe everyone does that. I just did it in a bigger... Sorry to cut.

Jay Shetty 1:23:46 No.

Brian Chesky 1:23:46 I just did it in a bigger way. Like, it, you can totally get how like I and Brian and Airbnb, they start to inmer- 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-

Jay Shetty 1:23:58 Mm-hmm

Brian Chesky 1:23:59 ... are merging, and as those two things merge, you lose who you really are.

Jay Shetty 1:24:03 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.

Brian Chesky 1:24:20 Yes.

Jay Shetty 1:24:20 Brian didn't ever have iconography. Like, there wasn't a, there wasn't like a mission list and a-

Brian Chesky 1:24:27 No

Jay Shetty 1:24:27 ... value list like before when Brian existed before. And so if you were to

1:24:32 – 1:28:17

How Do You Want To Define Family?

Jay Shetty 1:24:32 draw the iconography of Brian, the person not the Airbnb, I, I'm intrigued as to what that would look like if you started to design that.

Brian Chesky 1:24:42 I see a child. I see like a, a childlike curiosity and energy and love-

Jay Shetty 1:24:49 Mm

Brian Chesky 1:24:51 ... that I think I've always held onto.

Jay Shetty 1:24:53 Mm.

Brian Chesky 1:24:55 I also see the world f- 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, what 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.

Jay Shetty 1:25:21 Mm.

Brian Chesky 1:25:21 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 wanting to treat those around me like family, and what I mean by that is I'd try to do anything for them.

Jay Shetty 1:25:42 Mm.

Brian Chesky 1:25:43 Um, 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 idea. Uh, m- I mean, that's what I-- That mean that's the iconography

Jay Shetty 1:25:57 Mm-hmm. Mm.

Brian Chesky 1:25:58 I would hope that iconography is true to some extent. I guess as I think about it even deeper, I, I, I've used the word loneliness, connection, and community, but maybe at some deeper level, the deepest word is family

Jay Shetty 1:26:12 Mm.

Brian Chesky 1:26:12 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-

Jay Shetty 1:26:29 Mm

Brian Chesky 1:26:29 ... to your, like, close friends and to other people and just try to, like, e-re-expand that circle-

Jay Shetty 1:26:36 Mm

Brian Chesky 1:26:37 ... that's kinda what I would want. You know, if I design the world around me, then I better design it with other people in it.

Jay Shetty 1:26:46 And as you see that, do you, do you see the child or are you the child as you visualize that?

Brian Chesky 1:26:53 You know, it's funny, I kind of see both. I see-

Jay Shetty 1:26:56 Like, are you seeing the child sitting there or are you seeing the vision through the eyes of where you would be?

Brian Chesky 1:27:01 I feel like this timeless image of myself.

Jay Shetty 1:27:03 Mm-hmm.

Brian Chesky 1:27:03 Like, I, 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 can also see this, like, grown-up-

Jay Shetty 1:27:14 Mm

Brian Chesky 1:27:14 ... 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.

Jay Shetty 1:27:27 Mm.

Brian Chesky 1:27:28 It's almost like I have this image. You know, like, when you're like, you sit with the family at the dinner table-

Jay Shetty 1:27:34 Mm-hmm

Brian Chesky 1:27:34 ... where you're like, like, as a kid with your parents, your siblings, whatever. My image is that, but it's a very big table with a lot of people. And, you know, it ju- and, and that's not just, uh, uh, my close family that I might have. It's, you know, maybe, like, the, the broader people in my life-

Jay Shetty 1:27:52 Mm

Brian Chesky 1:27:52 ... 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 [both laughing] .

Jay Shetty 1:28:00 I love it.

Brian Chesky 1:28:01 Very well designed, and I have a design aesthetic that's-

Jay Shetty 1:28:04 Great

Brian Chesky 1:28:04 ... 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, and so yeah.

Jay Shetty 1:28:13 Beautiful.

Brian Chesky 1:28:13 [laughs]

Jay Shetty 1:28:14 Yeah. I saw, if, if you're okay with it, I want to share-

1:28:17 – 1:32:16

Marrying The Wisdom Of Older People & The Curiosity Of A Child

Brian Chesky 1:28:17 Yeah

Jay Shetty 1:28:17 ... 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 the now is protecting, but the childlike is that-

Brian Chesky 1:28:29 Yeah

Jay Shetty 1:28:29 ... 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-

Brian Chesky 1:28:38 Oh, it's really great

Jay Shetty 1:28:39 ... because 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.

Brian Chesky 1:28:46 I've always wanted to believe that I can have the wisdom of my grandparents and the curiosity of a child-

Jay Shetty 1:28:52 There you go

Brian Chesky 1:28:52 ... in one, that I have a foot... You know, Walt Disney, one of my other idols, used to in the, 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 past is my roots. I think I, I oscillate between the two.

Jay Shetty 1:29:23 Mm.

Brian Chesky 1:29:24 You know, culture and technology, massive scale, one of the big- become one of the biggest in the world with, like, the i- de- desire to always be a startup and always be close-knit. It's like these two-

Jay Shetty 1:29:39 Paradoxes

Brian Chesky 1:29:40 ... two paradoxes, competing forces.

Jay Shetty 1:29:42 Mm.

Brian Chesky 1:29:43 Yeah, and I, 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 I 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 a f- like you run a giant company is you learn scale.

Jay Shetty 1:30:05 Mm.

Brian Chesky 1:30:06 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 you 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, then you've gotta, like, make sure you have a legal corporation. You gotta now find a lawyer. You gotta interview the lawyers, and, and then you gotta, like, actually decide what 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 fifteen 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, a founder's different than a professional manager. A professional manager never saw it small.

Jay Shetty 1:31:01 Mm.

Brian Chesky 1:31:01 And as a founder, not only did you see it small, you created what was small. 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. 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 start, "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 powers of ten.

Jay Shetty 1:31:32 Mm.

Brian Chesky 1:31:33 Zoom out to space.

Jay Shetty 1:31:34 Mm.

Brian Chesky 1:31:34 Zoom in with a microscope. And that is just a way to think about things. And you are 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, they're, 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. In 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.

Jay Shetty 1:32:07 Mm-hmm.

Brian Chesky 1:32:07 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.

Jay Shetty 1:32:15 Yeah, it's

1:32:16 – 1:36:56

At The Core We’re All Connected

Jay Shetty 1:32:16 that balance between recognizing what's possible through scale, but at the same time being able to be embracing of your own insignificance.

Brian Chesky 1:32:25 Yeah.

Jay Shetty 1:32:26 It's like you see the significance, but yet you recognize-

Brian Chesky 1:32:29 Yeah

Jay Shetty 1:32:29 ... it's insignificant.

Brian Chesky 1:32:30 Yeah, yeah.

Jay Shetty 1:32:31 And that paradox is where-

Brian Chesky 1:32:32 It's so fascinating

Jay Shetty 1:32:33 ... yeah. The paradox is the only thing that's fascinating.

Brian Chesky 1:32:35 Yeah.

Jay Shetty 1:32:35 Like, you know, the human mind is a para- like 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.

Brian Chesky 1:32:43 Yes.

Jay Shetty 1:32:44 Right? Like the ocean and the sun are doing their own thing-

Brian Chesky 1:32:46 Yes

Jay Shetty 1:32:46 ... yet they're connected, yet-

Brian Chesky 1:32:47 Totally

Jay Shetty 1:32:47 ... they're doing their own thing.

Brian Chesky 1:32:48 And I think the more you start to see wider and wider scale, you sort of see you're right, that more and more things are connected.

Jay Shetty 1:32:54 Mm-hmm.

Brian Chesky 1:32:55 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.

Jay Shetty 1:33:01 Mm-hmm.

Brian Chesky 1:33:02 And so you s- but then you realize they're actually in some deeper way related, and y- that you spend the rest of your life kind of in that discovery.

Jay Shetty 1:33:09 Yeah. And y- 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.

Brian Chesky 1:33:21 Mm.

Jay Shetty 1:33:21 What connects it is that it's serving. The sun is serving.

Brian Chesky 1:33:24 Yeah.

Jay Shetty 1:33:24 The water is serving, the trees are serving, the trunk of the tree-

Brian Chesky 1:33:28 Yes

Jay Shetty 1:33:28 ... the leaves you talked about, the flowers, they're serving. Everything is giving a service.

Brian Chesky 1:33:32 Everything's interdependent-

Jay Shetty 1:33:34 Correct

Brian Chesky 1:33:34 ... on everything else, that we tend to have this illusion 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.

Jay Shetty 1:33:55 Mm-hmm.

Brian Chesky 1:33:55 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 gonna bond us is that we're actually so connected. 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.

Jay Shetty 1:34:35 Mm-hmm.

Brian Chesky 1:34:36 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."

Jay Shetty 1:34:52 [laughs]

Brian Chesky 1:34:53 And I'm like, "Well, okay." Like, I really do f- and, and it's like, and so, "Well, what, what do you find fascinating?"

Jay Shetty 1:34:59 Yeah. Yeah, I often say to people similarly that if you don't find someone interesting, it's because you're not interested.

Brian Chesky 1:35:07 Yeah.

Jay Shetty 1:35:07 Like you're not interested enough. There is something interesting about every person you meet. There's-

Brian Chesky 1:35:10 There is something interesting about everyone and everything, and that is what the cur- that, 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 'cause they're abstract, but if somebody's obsessed with basketball, then teach, uh, physics through basketball, through biology through basketball, teach history through basketball, the history of... So you just, you find something you're interested in. 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 an interest in how we should account for all the money we're making, what technology platform we should be on to enable Airbnb, 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've stuck.

Jay Shetty 1:36:05 Mm.

Brian Chesky 1:36:06 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's 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.

Jay Shetty 1:36:38 Yeah. And the house-

Brian Chesky 1:36:39 It's pretty wild.

Jay Shetty 1:36:40 It is pretty wild.

Brian Chesky 1:36:41 And it's just getting started, hopefully.

Jay Shetty 1:36:42 It's just getting started. Brian, uh, this is without a doubt the most unique episode of On Purpose I think we've ever had-

Brian Chesky 1:36:50 Really?

Jay Shetty 1:36:50 ... in four years. And-

Brian Chesky 1:36:51 No way

Jay Shetty 1:36:51 ... and I don't just say stuff like that. You can check with these guys. And, uh-

Brian Chesky 1:36:54 [laughs]

Jay Shetty 1:36:55 But

1:36:56 – 1:40:46

Brian on Final Five

Jay Shetty 1:36:56 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-

Brian Chesky 1:37:11 Yeah

Jay Shetty 1:37:11 ... I'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?

Brian Chesky 1:37:22 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. That's kind of a long sentence, but-

Jay Shetty 1:37:43 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?

Brian Chesky 1:37:52 Anything that involves chasing status, not because it's bad, but because it's actually a horrible way to even get it.

Jay Shetty 1:38:00 Mm, love that answer. Yeah. Question number three: How would you define your current purpose?

Brian Chesky 1:38:06 To try to help- Bring the world together, even if it's in the end a small way

Jay Shetty 1:38:12 Question number four, if you were being remembered after you were physically gone, what would you hope to hear?

Brian Chesky 1:38:21 We miss him.

Jay Shetty 1:38:23 Uh, 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?

Brian Chesky 1:38:32 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-

Jay Shetty 1:38:51 Mm

Brian Chesky 1:38:51 ... and to step in someone else's shoes. And the more different, the better.

Jay Shetty 1:38:56 Well said. Brian Chesky, everyone. Brian, that was, uh, 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, 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, I truly had a, a special internal experience myself.

Brian Chesky 1:39:37 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?

Jay Shetty 1:39:53 Absolutely. Thank you so much.

Brian Chesky 1:39:55 Thank you.

Jay Shetty 1:39:56 I'm so grateful for you.

Brian Chesky 1:39:56 Well, thank you for having me today. [laughs]

Jay Shetty 1:39:57 Thank you so much.

Brian Chesky 1:39:58 It's been great.

Jay Shetty 1:39:58 Such a 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 were 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.

Brian Chesky 1:40:24 Thank you, Jay.

Jay Shetty 1:40:25 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.

Speaker 1:40:37 Look, am I hesitating on this because I'm scared of making the choice, 'cause I'm scared of doing the work? Or am I sitting with this because it just doesn't feel right yet?

Episode duration: 1:40:46

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