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

26:12And I just don't really have much of my life outside of work. My work was my life. And then I remember having a 40th birthday party and I had to make a list of people to invite. And never in my life have I tried to like make a list of who my friends are. But when you have to make invitations. You have to make a list. And I made a long list of people. And then I kind of went down the list and I said, when's the last time I talked to these people? And I realized that almost every single person in the list, if I were to ping, I'd have to catch them up in my life. I couldn't just dive into something because I had not maintained those relationships.

26:49And it was just something that like started, you know, and 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 lonely. I knew I was isolated, but I didn't know that that also meant loneliness. And I thought, I have all these people around me. How could I possibly feel this way? And there were a couple people that entered my life that gave me some awareness and consciousness. One at the deeply personal level and one more at the professional level. at the personal level I ended up actually becoming friends and a person who became a mentor to mine was the former president of the United States Barack Obama and it was like a kind of a crazy story where I you know I like many people met him in the White House and then he we keep in touch after the White House and he became a bit of a mentor to me we developed a relationship and initially it was a purely professional relationship but by 2021 after in public, he kind of told me, I kind of told him what I was feeling.

27:54And he said, I think you're kind of lonely and you probably need to renew friendships. And he described that he had like these 10 or 15 friends. Most of them he was friends with before his presidency. And they kept him grounded and rooted. And your roots come from your past and your past is often your relationships. Because I kept asking him, like, how did 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, those people that I hadn't really kept in touch with.

28:29And so I rekindled relationships with my college friends. And I committed that we'd take like one or two trips a year. Because the problem is if you don't see your friends, you only text them. The only things you can talk about are like the same old stories from 20 years ago. Or you can talk about other things in your life, but you have no shared experience. In Zoom, in phone calls and text messages are not shared experiences. You can only talk about an experience you had. And so I did that with my college friends. I did it with my high school friends. I started spending more time with my sister and other people in my life.

28:58I ended up getting a dog, a golden retriever named Sophie Supernova. And the crazy thing, Jay, is I can tell you, the ride of Airbnb and having all the success and money and power and all this stuff, it can be amazing. I'm not saying it's not amazing, but I actually think I probably, it's almost like I had to go on this entire journey to realize I had everything I needed before I even started the journey. That the thing that probably gave me the greatest life satisfaction was a thing that I didn't even need money for and I didn't even need to have success to achieve. Relationships, many of them I had before I started.

29:35I couldn't be more excited to share something truly special with all you tea lovers out there. And even if you don't love tea, If you love refreshing, rejuvenating, refueling sodas that are good for you, listen to this. Radhi and I poured our hearts into creating Juni sparkling tea with adaptogens for you because we believe in nurturing your body and with every sip, you'll experience calmness of mind, a refreshing vitality, and a burst of brightness to your day. Juni is infused with adaptogens that are amazing natural substances that act like superheroes for your body to help you adapt to stress and find balance in your busy life.

30:14Our super five blend of these powerful ingredients include green tea, ashwagandha, acerola cherry, and lion's mane mushroom. And these may help boost your metabolism, give you a natural kick of caffeine, combat stress, pack your body with antioxidants, and stimulate brain function. Even better, Juni has zero sugar and only five calories per can. We believe in nurturing and energizing your body while enjoying a truly delicious and refreshing drink. So visit drinkjuni.com today to elevate your wellness journey and use code ONPURPOSE to receive 15 % off your first order. That's drinkjuni.com and make sure you use the code ONPURPOSE.

31:00I 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 or 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 of 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.

31:33And I think it's made me a better leader. Because one of the things Robert told me is 50 % of CEOs are lonely. Now, somebody listening to say, oh, poor CEOs. Well, I would say, I don't think I want society to be led by a bunch of lonely people. Exactly. 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.

32:05And we especially don't want to live in a world where leaders are lonely. And so this has been one of the defining things in my life. So I think the first part of the answer is for me to deal with my own sense of isolation and loneliness. And again, Jay, I thought loneliness was something that like people's grandparents experienced in their life. I didn't think it was something the young person experiences. And the other person I met is the now and former Sergeant 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, go into Airbnbs and they were worried about like germs on surfaces.

32:43And 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 to me. He said, Brian, do you know what the number one killer in America is? I'm kind of paraphrasing the conversation. And I said, I don't know, is it like heart disease? Is it cancer? And he goes, no, the number one killer in America is loneliness. And I said, loneliness? What are you talking about? And he said, yeah, being chronically lonely is worse for your health than smoking a pack of cigarettes a day and can take 15 years off your life.

33:13And not only that, but about half of Americans are lonely. Two out of three teenagers by some studies are lonely. And it's not just that they're lonely is that this is leading to a lot of mental health issues. You know, one in four teenagers have suicidal ideations. You know, that's not just teenagers. You see like, you know, like there's a crisis with men and boys. There's a crisis with like one in three seniors are lonely. This is like, so I started realizing this is like a really big crisis. It's, it may be a way to say it's a crisis of disconnection. And I started realizing like, you know, global warming, maybe you could say that's disconnection with the earth and that loneliness is disconnection from each other.

33:54And 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 in 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 Of course, we never fully leave our history and our psychology. And so then I started learning about loneliness at the intellectual level. I started asking, well, Airbnb is a global community. We have hundreds of millions of people.

34:27Some of the best ways to connect with other people are through travel. I was using travel and Airbnb to connect with my friends because 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 of choices. You can just stop and say, like, retire. you can do something new or you can just say my work is just getting started and for me like i want to of course i want to like keep getting a return for shareholders and make sure like if people give me money they feel like it was a good decision if employees put their trust in me it was a good career decision and and i i want all that to happen but that can't be enough that there's got to be something more the artist in me the designer in me wants to solve a problem the problem can't just be a stock price.

35:11It's got to be something greater. And I have like the, one of the biggest canvases in the world of any designer ever. And what I'm going to design is not products. I'm going to 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.

35:41But the problem is it's like ingredients. We evolved, I think, to be in physical proximity with one another. And as we spend more time online, we seem to be spending less time together. And I think we have to be very, very careful as a society what kind of future we want to design for ourselves. So I guess for me, loneliness in its solution, which is reconnection, has been both a personal mission and now a bit of a professional mission. And a product or a service can't help with that, but a community can. And if Airbnb can go from a travel service to a travel community, if we can be in the business of trust where you understand one another and we can help you connect with people in your life or meet other people, that to me would be where the next chapter is and there's something about like solving your own problem and 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 thank you for coming to my ted talk that was like that was uh that was a master class on loneliness uh and i mean that and it's beautiful to see how it can so deeply correlate with what you've already built.

37:02And 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. They're awesome. And bringing them all together and saying, look, actually it's additive. I think a lot of us have this tendency in the material world to build something, go, ah, it wasn't it, throw it away and then go try and build something else. And actually what you're saying, actually I built this thing, it's great, but actually it could be so much better and it's just the beginning.

37:31Exactly, 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. 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. But if you do it because you love it and you get to do it with people you love and you can do it out of a sense of gratitude, and giving to other people. You know, Steve Jobs, one of my heroes, used to say, I get to work now with Johnny Ive. He started a firm called Love From, Love From Me To You.

38:04And that was the theory that Steve said. Steve said the best way to show your love for the species is to put your heart and soul into something and give them to them. Steve said that design is a fundamental soul, the man-made creation that reveals itself through subsequent layers. And I think that ultimately my motivation has gone from 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.

38:40I 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, it's just amazing to be able to buy things and have things, those experiences are awesome. but the things that probably give me most joy is like sharing things with others or giving things. I totally get now. I never understood like why people like giving away things. I didn't really understand. It was not intuitive to me growing up. I was parents of social workers, kind of middle class. And now I realize there's, I don't wanna say a selfishness to it, but you get something.

39:11You 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, by giving love, you kind of get it back in return. And I think ultimately, I think me as a leader, I never saw something like me growing up. I went to design school and there was this weird thing, Jay, where I get to RISD, the Rundown School Design, and there was this obsession about getting design in the boardroom. And Joe and I were so audacious. We thought, why should design be in the boardroom? We can run the boardroom. But of course, designers, people never thought started companies.

39:51And 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. Airbeds instead of beds for air bed and breakfast. But ultimately, 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.

40:21I get out of bed every day to design something amazing. And of course, I can pay money. I can fund it. And that's just a kind of motivation. And that probably can keep me going for a really, really long time. And I find that a lot of companies, they get really cold as they get big. That you start something for love. You're the customer. You talk to the customers. And at some point, the company grows. And you start with the head and the heart. You like putting your love into it. You're intuitive. No startup is data-oriented because there is no data. If you have an idea, there is no data. So you go off your intuition.

40:51You do something because you believe in it. And then at some point, you get so big, the company gets financialized. There's a lot more data. And you start making decisions with the heart and now with the head. And one side of your head. And you look at the Fortune 500. How many CEOs in the Fortune 500 truly have any creative background whatsoever, identify as creatives? Almost none. Okay, how many boards? There's 12 members on average of a Fortune 500 board. That's like probably 6 ,000 members of the Fortune 500. How many boards have creative people? Not many. How many executive teams have it?

41:25And so I guess the question is, there's nothing wrong with the scientific method. There's nothing wrong. It's great. But 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 a design-driven company, like the world's biggest RISD project that just never stopped, a company with a sense of a spirit, a sense where a logo is like an inverted heart. It was meant to be this idea almost of this beating heart, like this lifeblood that would flow through the community.

42:06And I'm not saying we do all that. That might be an ideal that we've never gotten to. But you can. but we can or we'll die trying yeah you've you've sparked a lot of thoughts for me that i'd love to share with you that you've reminded me of so many things my mind is connecting so many dots with what you're sharing the first thing that came to mind is it's really there's a beautiful statement by paul tillich who's a writer who said that it's fascinating that there are two words in the english language for being alone yet we only use one of them and he said the two words are loneliness which is the word we use and the other is solitude.

42:41And when you said we're disconnected from the earth, we're disconnected from each other, but really we're disconnected from ourselves. It's because of a lack of solitude. When I lived as a monk, being comfortable, being alone was the first lesson of the day. Wow. Because the idea was that - And how do you learn how to do that? Well, there's many techniques. One of the first techniques is if you just sit with yourself for long enough, you start to see so much in yourself that 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 incompletes there's a great um one of the late great mythologists of the 20th century you probably know is joseph campbell of course he had this great quote, the cave you fear to enter lies the treasure that you seek.

43:42And 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. 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 it's so powerful because so you mentioned Steve is a is a hero of yours same with me I feel like I've studied everything he's ever said or written and one of the things I love this was an interview that Mark Zuckerberg was doing with Prime Minister Modi from India and he said this on stage to Modi I believe this was in San Fran and Mark said to him he said when he was struggling with the direction of Facebook now Meta in 2009 which is five years old Facebook is right he went to his mentor his mentor happened to be steve jobs and he said to steve he said what do i do i'm struggling 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 wow for i want you to go live there and i promise you if you go there you'll figure out the direction of facebook and mark said he actually went to that monastery that ashram and he said in that ashram that's where he decided that at that time facebook was about connecting people oh wow and what i know that story yeah and what i find fascinating the reason why i like to share that story is i'm always fascinated by what a tech entrepreneur thinks as much as what i'm fascinated what a monk thinks because it's that cross-pollination it's that extreme of diverse thought where those two things don't collide they don't have the same agenda we're not living in an echo chamber when you're talking to an artist and an entrepreneur there's no echo chamber you've broken it open now.

45:30And so for me, MIT did a study on that where they found that the most innovative employees inside an organization were people who didn't know people who knew the same people. There were people who knew people who had random connections. So their network chart was completely uncorrelated. Whereas people who had networks who were correlated were less likely to be creative and entrepreneurial. There were fewer unknown discoveries. And I feel like in my own life, like Steve has the saying, you can't connect the dots looking forward. You can only connect them looking backwards. I grew up playing ice hockey.

46:03I 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 a designer at a firm. Then I went to Silicon Valley with very little and like got thrust into the technology industry. And it turns out that I did not know how any of these experiences would add up together. And they all came to me. And every single one of them I've used, every single experience, but I could never have reversed engineered how to get there. And it is amazing that, like Steve used to say, the best engineers were also poets.

46:45And he was really saying that creativity is about connecting dots. It's about having disparate experiences and bringing them together. And if you haven't had a lot of different experiences, if you aren't very multidisciplinary, you're not going to be able to. I mean, Einstein was like a violinist. I think a lot of the greatest scientists have leaps of the imagination. They're not just using empirical information. And a lot of the greatest artists, they have an organized mind. Sometimes they have a fascination with numbers. So you start to bring things together. And I think that is exactly what we probably need in this world.

47:18I mean, we need more creativity. You know, whenever you see two bad options, you don't like it, the right answer is the third option. The third option is one you haven't come up with yet that requires novel, innovative, imaginative thinking. Where does it even come from? Where does creativity come from? If creativity, you know, I don't know if Einstein ever said this, but there's a quote attributed to him that is that logic can take you from A to Z, but imagination can take you anywhere. I love that quote. Don't know if he said it, but I believe it. But where does that come from? Where does imagination and creativity come from?

47:50I think it comes from a sense of openness. It comes from curiosity. It comes from maybe not first following your passion, but following your curiosity with a deep intensity. I'm Radhi Dvlukia and I'm the host of a Really Good Cry podcast and I have the opportunity to talk to Logan Ury. Logan is a dating expert, a behavioral scientist, a best-selling author, and someone who is seriously changing the way we think about love and dating. In our conversation, we talk all things dating, that Logan has studied and tested from what to put in your dating profile, the pictures you should and shouldn't be using to the conversation starters that actually work.

48:25And the huge no-nos that people probably do not realize are reducing their chances of success on apps. Whether you're single, dating, or just trying to be more intentional in love, Logan offers the kind of clarity we all need. Relationships do require work and the best relationships are people who really work on them together. They're so focused on if I find the perfect person, then I'll have the perfect relationship instead of understanding really that they can choose someone great and then build that relationship together. They don't need to keep searching for perfection. Listen to A Really Good Cry on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

49:01And being curious about so many different things and trusting that you can be curious about something and learn about something, not knowing if it will ever be useful and have the trust to say that every single thing you'll do in your life, you'll do with accumulation of every single experience you've had before. And that the more places you've gone, the more people you meet, the more things you learn, it will all come to you. And you might not know ahead of time how it will be useful. And honestly, if I hadn't gone to military school, I probably wouldn't have been so organized. If I didn't go to design school, we probably wouldn't have been as creative and innovative in our thinking.

49:36If I hadn't played team sports, I probably wouldn't have understood about camaraderie. If my parents were social workers, I don't think I would have had this focus on service 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 going to have a singer to be a musician. I did not think I was going to be an astronaut politician. And so I'm like, I don't know who I'm going to be. I don't know what I am. And the word entrepreneur was a word I'm not even sure I heard of growing up.

50:10To me, it was an obscure French term. I didn't know what it meant. And I saw Walt Disney as a kid on television. I thought one day I'll work for him, not thinking I would start a company just like him. And I never imagined that was possible. I guess we're all born with unknown potential, as I said before, but you have to live experiences as many as you can. You put them together. And I hope my story inspires people, not for the remarkableness of it, but the ordinariness of who I was before. To say that, like, if I joined the giving pledge, if you ask 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.

50:52I don't think that takes anything away from the teachers. I think it just means that maybe that potential is in so many of us. And it's also maybe a little bit random and anything is possible. And you, like, the story you tell yourself might not be accurate. And 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, determination, you wake up one day, you're like, oh my God, look where I am now. 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.

51:40Yes. And so if you look at your journey just as a series of random dots, they're all anomalies. Social working, hockey player, design student, like they're just random things. But you're able to actually paint this tapestry where you're going, well, actually, everything that I do today. And I've often felt that in my own life that I lived as a kid growing up in London. My favorite subjects at school were art and design, philosophy, and economics. Those are my favorite things in the world. Spent my entire life being immersed in that world. When traded it in to go to Cass Business School to study management science with a focus on behavioral science, because I thought it gave me a career, only to give it all up, the safe job to go live as a monk, 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.

52:24went into consulting, then came out and do media now. And I completely agree with everything you've just said. 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. Correct, it's the end. Has made you who you are, not one of them, but all of them. And I think that like the one advice I would give my college self is to try more things and have more experiences and don't seek status. And part of the reason why one should not seek status is because we can't even predict what industries will be around the future.

53:02Growing up, status to me was like, I don't know, it was like being an investment banker or something or something. I don't know, it was like fields that may not even totally exist in their current form in the future. So I like to say, you should do things you're good at, but you tend to be good at things you're interested in. You should seek out whatever you're curious about, whatever you're interested in. And then you want to get to the frontier in some way. At some point, you'll learn everything and you'll get to the edge of all that's known about that subject. And that is an uncomfortable period where you peer off the ledge of a cliff.

53:35And 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 it's amazing that like anyone can do that. You know, you can do it because anyone can do it at any scale, you know, and you can do it in your humble way, like on the side, something small, or you can do it in a really big way, but it feels the same no matter what the scale.

54:07You just told us what you'd say to your younger self. If you met your younger self now, let's do this exercise. What do you think your younger self would say to you? What would it be proud of? And what would your younger self say? We need to reconnect with this. 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 meeting my friends, I said, this will be huge. One day thousands of people will do this. Like that was 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.

54:48And so I do not think, My younger self, let's say my college self, did not think I could run like a Fortune 500 company. For every$1 ,500 spent in the world,$1 spent on Airbnb. Did I think I could lead an organization that's facilitating? No, I did not think I did. And so that would be probably the thing I would be surprised in a very positive way. But the other thing I would probably say is, wow, I'm 41 years old and I live alone. then 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 attention, adulation I get, I think I would have maybe looked at my life now or my recent life and identified a little bit of isolation.

55:38And I think the lesson is a couple of things. One, I think that things have happened in a different order than I imagined. It's hard to predict. I didn't think I'd be this far along in a career, and 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 part of me, and this is probably true of a lot of people, we have this tape loop of whatever we thought of ourselves as a child, it's just frozen in times repeating ourselves.

56:15and you just compulsively just keep doing something. And like many people have addictions and I probably had one that was probably work. And I think I'd have to, I would hope my childhood self 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. Thank you for that. Thank you for opening up and going there. I felt that. What is a thought that you say you have too often? I wonder what they'll think. Speaking of Dr. Waldengar, Robert Wong. I love him, yeah, he's a good friend. But I met him last week for the first time.

56:46And you've had him on your show, right? Yeah, we've spent a lot of time together. I love him. Something he told me last week that really stood out to me said one of the biggest regrets that people have in their life is having lived their lives worrying what other people think. And I kind of understand why from an evolutionary standpoint, you kind of have to care what people think because you have to fit in. And if you don't fit in, you don't belong. You're isolated. If you're isolated, it's a death sentence when the only thing you have is the village. But it turns out that that is not true anymore.

57:14that like it's okay to be misunderstood and that it doesn't, maybe it doesn't matter what people think, or maybe it doesn't matter what they think today. And that some of the greatest things I've ever done, I was at least temporarily misunderstood. And maybe it only matters what a few people think. And maybe, just maybe the person that most matters what I, what they think is yourself, right? That you just listen to your own voice, not other voices. and I think if I can do that artists will call that artistic integrity you had Rick Rubin on the show he talks about 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 that's something I have to continue to do and the crazy thing is the more success you get the more you start performing for an audience and you have to be very careful about performing for and appeasing an audience.

58:13And once you become something, people expect you to be that thing. You know, imagine like you happen to be something forever. But what if you change? What if you grow? What if you want to do different things? And that's a challenge I have, right? The Airbnb brand means something. I gotta be careful about changing that brand. It stands for something. And yet I, as a person, I'm not meant to be the same person every year. I mean, how could I be? I learn, I grow, I change, I have new experiences. and so having the permission to continue to change and evolve and not be so self-conscious of what what people think that's something that i always struggle with because i don't know part of me i think i'm like a people pleaser and one of my challenges historically be is like some people like i'm like i don't always like interpersonal conflict i like to appease people make them happy and that's got a good side and it also can be a bit of a prison over time and the bigger you get the higher the walls get.

59:10I want to just point out something you said that was so subtle, but so powerful for everyone who's listening and watching. I've never heard it put that way, but the idea that we often think it doesn't matter what people think. And you said, it doesn't matter what they think today. And 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 can be negligent. But the idea that it doesn't matter what they think today about what I'm thinking. And - Thank God. Yeah. Thank God. You know why? When we first came by the idea, One of my first investors said, don't worry about people stealing their idea.

59:40If it's any good, everyone will dismiss it. We tend to believe things were good in hindsight. Some of the most revolutionary people and ideas were revolutionary because they were misunderstood in their time. That if you have to be at some point in your life willing to be misunderstood. And the solitude you can have are two things, I think. Number one, to not be so attached to it. To realize that ultimately you can't predict the outcome. just do what you believe, follow your heart. And if it's true, whatever has happened is meant to be. But the other thing you can do is to escape into the future, to say, to have this, we call it a vision for a reason.

1:00:17You 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. There's a beautiful statement, which is probably my favorite, which you've just encapsulated so well. It's from Charles Horton Cooley. He wrote it in 1896 or something like that. So he said this early. And when you hear it, you're like, wow, that was said yesterday. He said, the challenge today is, I'm not what I think I am.

1:00:54I'm not what you think I am. I am what I think you think I am. and he said we live in this perception of a perception of ourselves so we don't even know what we look like we we are who we think other people think we are and that's twice removed from yourself and that distance we create from our understanding of ourselves versus what we think someone thinks of us totally how will you ever know what what do you think is something you are still trying to understand about yourself or if you think you misunderstand a part of who brian is? What are you still trying to understand? I think that we tend to have an outdated image of ourselves.

1:01:34And that makes sense, right? Like think about I'm 41 years old. So my image of myself is the average of the last 41 years. And if the average of the last 41 years, the median is 20 years old. And so I still see myself a little bit like that person. And people, most people see me today. And a lot of people are going to see me for the first time right now. And that's their impression. And that's a delta. And I often wonder, like, sometimes I, you know, I probably have had a little bit of imposter syndrome, like, what do people see in me? And why do they follow me? And like, I, because they do, like, at some point, you're a leader, and you're a leader, because people choose to follow you, and you don't, like, impose yourself on them, they ultimately believe in something.

1:02:14And 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 found what will make me happy at a professional level. I was really lucky that I discovered something that I love very early on. I found a perfect harmony between what I was good at, what I loved and what kind of society valued. And those things just clicked into place and I was able to find it. But I think I've been on a lot longer journey to figure out like what will make me happy like in a larger sense of the word and it turns out that success and status to some extent have benefits and you know but it's not it's certainly to say it's not everything's an understatement I think I'm still trying to I'm still trying to learn that and maybe I'm trying to figure out, you know, at this age with so much, so many resources, like I almost feel like in a way my life's just beginning.

1:03:19And so it's just beginning then when I can't connect the dots looking forward, it's a discovery of who am I and who am I meant to become? Like, is this my story or is this the end of this, the middle of the story, the beginning of the story? and what am I meant to do next? And I'm kind of learning a lot more about myself every year. That's a brilliant mindset. 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?

1:03:58Like how unmeaningful and unfulfilling would it be? And the fact that you're asking those questions at this point. Maybe one other thing can I add? Oh, of course, you can add wherever you want. So over a year ago, it was February, Russia invaded Ukraine. We got word that there'd 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.

1:04:39And I want, I always try to use, that's the other device I use. I try to think about how I'll be viewed in the future, but I also want to, I always think in a crisis, how do I want to be remembered? Even if no one will remember me, And I think anyone can do that. How do you want to be remembered by history, even if it's just an intellectual device? Because maybe not a lot of people remember. That's okay. But live your life as if you'd be remembered. And what I realized 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.

1:05:09But it came from this basic idea of how can I help? And maybe that is the other version of my question of my life. At this point, how can I help? with everything I have. 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 hope that what I do provides me happiness. And I've noticed that the things that make me happy are kind of helping and giving others. I don't mean to sound cliche, but you start to realize what provides happiness and value for you.

1:05:46And so that's kind of something that I keep thinking about. And that's what I love about entrepreneurship and creativity and design is you make something maybe initially for yourself, but then for other people. And the real joy is seeing them use it. Absolutely. I think I was really fortunate 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 interesting yeah 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 when anyone gets to a point of getting everything all they can do is give it away in a way that fuels them to a mission that is aligned with their purpose, not just wherever it goes, but in a meaningful way.

1:06:47You 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. Yeah, totally. When you think about that being single or being, 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 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 and all that.

1:07:37And I think it's this incredible and positive to a point, but if you're not careful, it can become all-consuming. And the thing about a tech company or a startup is like, it's like imagine, again, you have a three-person band that's now a 30 ,000-person band or a three million person. There's always more you can do. It can, if you're not careful, become a one-dimensional addiction. And I think that it's like the thing that made me successful was my singular focus. But I have to be careful that the thing that could then turn against me is my singular focus. And so I think it's like the way to live my life in the next 20 years can't exactly be what I did in the last 20 years.

1:08:24The last 20 years worked out pretty well, so why would I do anything differently? But of course, if I don't do anything differently, then I'll be 50 or 60 and nothing will have changed. and so I think it's really about like seeking community the word community means harmony to live in harmony in balance and I and having that and so I think it's just old habits and habits that been rewarded so but you got to be very careful about those habits I think that I think that's what it is and I also just yeah I don't know what do you think when I listen to you and being with you for the time that we're spending together and obviously it's the first time we've met.

1:09:03You'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? I think that's a big insight. And maybe that's what I'm still trying to discover. Yeah. I would say that you sound so clear that if you actually had clarity, then I don't think it would be hard, but it's hard to have clarity. That's the hardest thing things to have clarity. That's a good point. And so when you have clarity, it'll be so much more easier for you to create.

1:09:35You can't create something if you don't have clarity. That's a great point. And so that would be my hypothesis at least. And that's what I was going to ask you, what at least are those sprinklings of those clues? Let's go with that word. What are the clues of what you think could develop into clarity around what you're looking for in a personal way? You've talked about so prolifically about what you want professionally, which is this using Airbnb as this phenomenal platform to build community and connect people and, you know, eradicate loneliness, which I love. Like, I love that. That's phenomenal clarity.

1:10:06And 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? 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 timescales 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, how do I get clarity?

1:10:39When I started Airbnb, before we started Airbnb, I didn't know I wanted to start a tech company and I wanted to be about helping bring people together. And I was going to start with these two people and I was going to be a technology founder and I was going to marry art and science and do all this stuff. I couldn't have known any of that. 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 both well-known people and lesser-known people. I had an intense curiosity.

1:11:15I was drawn to certain types of people, and I had action. It's like if you can't follow your passion, you follow your curiosity, where does it take you? and you know like you're not going to start a company by like never like starting and you're not going to build a personal life you want by not starting either and so you just go on that journey and you you will you will i think you will find what you want if you start and you keep moving yeah that feels right something like that i'm excited to see you you know i'm excited to hear about how you take that short moment of clarity that we've gained into the future because no that's 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.

1:12:01Not in the luck sense, like you said, of the right timing, but that each one of your experiences has made you make better decisions. And I think that maybe the 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. and that would be fun. It'd be fun to check in in a handful of years and see what played out. Yeah. Yeah, definitely. Definitely. And it's so, it's so interesting that you keep quoting this. I've never met someone who loves quotes as much as I do.

1:12:32So it's, uh, it's fun hearing them back from you and how they played out in your life. What, what if anything today, apart from everything we've talked about, we've talked about so many things. What if anything today keeps you up at night or do you sleep really well? I don't know if I sleep that well. And I, not to use another quote, but Pavel Caso had a saying, the older you get, the stronger the wind gets, and it's always in your face. And I think that could be true of companies. What keeps me up at night is, you know, like people ask me in the professional context, what keeps you up at night in the company?

1:13:02Like, 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 we started in 2007, 2008, it takes off by 2009. I go on a 10-year journey. It's now late 2019. And I remember having a dream, a bad dream, that I woke up and I was running a company that was unrecognizable from anything I ever attempted to start. It was like I was in a wilderness for 10 years and I came back. And I remember going on a hike in Bolinas, California, where Joe had like a summer house.

1:13:40And we went on a hike, Joni and I. And I told them about this dream. And they said, well, what did you find? I said, I was horrified because the company we set out to start is unrecognizable we have today. And they go, what do you mean? I go, well, people are complaining that it's big, it's bureaucratic, it's slow moving, people are more complacent, cost is rising, gross is slowing. It's starting to feel like a corporation. And I didn't know what to do. I felt like we needed to like not blow it all up, but change it all, like take the house back to the studs. But the problem was we're about to go public.

1:14:12And that's like a really bad time to do that. But I had this image in my head of this kind of company that I want to have. This image was to build the most creative place on earth, to build the world's biggest startup, to build a company that felt small, that was completely focused not on a product or service, but a community. I was starting to come to the conclusion by 2019 that you can't be big and have a soul. At some point, those things were at odds, that the problem was being big. I didn't know what to do. and all of a sudden we get word in February 2020 that our China business has collapsed by 80 % because this thing called COVID.

1:14:54We'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 had today There's something about almost losing everything And everything I had, at least at that time I thought was the professional That gives you clarity Imagine your house is on fire And someone says you can take 20 % of the things out of your house Suddenly you have to make that choice And you get really clear about what's important People start telling you, I want Airbnb to exist You say, why?

1:15:38And they tell you It's as if they're giving the eulogy before you're even dead and how you want to be remembered. And you start to ask yourself, I don't know what's going to happen, but how do I want to be remembered? And at that point, we stepped into action and we basically rebuilt the company from the ground up. And this is 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 Johnny Ive, who was Steve's partner in design. And the other was Hiroki Asai, who was Steve's creative director. and they told me about the way Steve ran the company.

1:16:13And actually, a funny even further aside is I remember one time, I remember I went to Steve's house, I never met him, and I saw these books on the shelf from Robert Ammonheimer and I asked his wife, what is with the Robert Ammonheimer books? But as I started studying, I realized that it was this idea that you, almost like Robert Kepernan, the whole bomb in his head, that this idea that the leader collects all the information and that you're the center, that it's not a pyramid. You're not top down, you're inside out. You're the son of a solar system. But your job is to emit light and bring decision-making in to pull in this shared consciousness.

1:16:51And 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. And that we would just, there's this really specific we ran a company. And that was basically the way I found ourselves out of a crisis. So the lesson of the story is through that I was able to get a lot of clarity through this crisis.

1:17:29I 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 yeah that's exactly where I think we're headed that you have an opportunity to avoid the crisis yes in order to not be not everyone needs that crisis no you don't it sounds like do you still when you present ideas they're so visual you see them I feel like you can see everything you're talking about and I can see it with you. Everything in my head, 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.

1:18:11And 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 chess board and 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.

1:18:54Like, you know, this is how I tend to see things in three dimensions, spatially. It's really rich, vivid colors. And that's just how I think. You know, I think other people will think in abstract thoughts or numbers. Some think in terms of language, but that's how I do it. You know, and it probably doesn't surprise you given my background. And do you see yourself in that or is that happening and you're observing it? You know, you might've hit on something. There have been times where I'm trying to design a world that I want other people to live in. And I think it's like I want to vicariously live through them.

1:19:30It'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'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 technical design monastery. Like, you know, and that's kind of what the pandemic was. I described it almost like a monastery, except with Zoom. But if you didn't know I was at Zoom, you'd just think I was meditating all day, right?

1:20:15Like I'd just be sitting in one chair. And so that's a great thing. 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 forget why you do things and you get disconnected. connected. Wow. I'm just kind of, you're making me think of all this now.

1:20:50You're making me think too. I love it. No. 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 into. Yeah. Sometimes people don't know why they're doing it. Correct. 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?

1:21:27And you know the number of people that forgot why they're doing it? The number of people that are self-driving cars, there's a destination that's in the car, they're driving towards it, but they don't even know what that destination is. And that's when you don't look inside yourself. And if you're not careful, you will basically be on a super highway going somewhere not knowing why you're going there. And you may wake up and end up in a destination that wasn't where you intended. I think having this clarity is so important. Who am I? What do I value? What do I want to do in this world? It's taking the time to reflect.

1:22:04And I think the best businesses are really introspective by introspective leaders. 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 it changes. Here are our values. Here's the kind of people I wanna like work with. Well, what do they all have in common? They're curious, they're optimistic, they're kind of creative. They tend to like hosting other people. Okay, those become what we call values. What are the shared lessons? What are the shared stories? And the more you can start to be really reflective, you're right, the more you're clear about what you want, the more you get it.

1:22:36Our 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 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. But in a weird way, they also seem like the most possible to change. And so that's something that I've seen. 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. So most confused people I've met are the most powerful because at some point the power and success can be confusing.

1:23:17You know, you had a purpose, but you also have all these demands and you stakeholders and you can get fused by appeasing people. And you like, 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. A lot of leaders get confused. And I totally see how that happens. and I think finding your way back home is key. I would be intrigued to see if you close your eyes now or whenever you chose to see what you saw when you looked at your personal life.

1:23:55You're talking about your professional life as being all these thousands of decisions moving. And you say like kind of that period of self-reflection, right? Yeah. I think I saw somebody who was kind of

1:24:08almost punishing myself and romanticizing suffering because I thought, you know, to some extent I maybe believe that I was going to give everything to the company. And it was like this selfless act, but it became so selfless that I then could start to lose a sense of myself. I mean, you know how weird it is. I always kind of joked, like if I die, will I die Brian Chesky or the Airbnb guy just died, you know, like, and like am I Brian or am I Airbnb? And like, you know, like they get really, one is an icon. That's a noun and verb you know ubiquitously around the world. The other is a person that not a lot of people know, really know.

1:24:48And when you, it's very careful that I started becoming the company and this company started becoming me. And I think 70 % of that was good because that meant the company I think was a person, had a face, is humanistic, it was in the details. But when you become a company, you cease to be a person and then you lose a sense of yourself and then you become an icon. And by icon, I don't mean famous, I mean iconography. Icon is short for an iconography and iconography is for a symbol for something. And of course, people are much more than symbols. And I started seeing that I started becoming a symbol and a thing and I stopped listening to myself.

1:25:33And by the way, you get pressure from shareholders to drive a stock price. You get pressure from employees to make it a better work environment. You get pressure from hosts. But no one gives you pressure for yourself and your personal life. If you don't create that own pressure, 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 kind of designing the world I want to live in and then living in that world and choosing to actually live in that world. You've interviewed so many people but I'm so surprised how many leaders don't actually live in that world.

1:26:15I tend to think that some of the most successful people are people that they get so disconnected from what they intend to do when they started And so reconnecting, I mean, so much of this, I guess I tend to see everything through that lens, but so much of it is about reconnecting that, that reconnection, that path back home. I love what you were saying about the iconography and how the human meshes with the iconography. And you described earlier the. And maybe everyone does that. I just did it in a bigger, sorry to cut. No. I just did it in a bigger way. Like you could totally get how like I and Brian Airbnb, they start to emerge.

1:26:52But I bet you even people who don't have a giant company, who they really are and the person they're like supposed to be are merging. And as those two things merge, you lose who you really are. 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 even harder, I'll tell you why, because when you built Airbnb, it had iconography. Yes. Brian didn't ever have iconography. Like there wasn't a, there wasn't like a mission list and a value list like before when Brian existed before.

1:27:30And so if you were to draw the iconography of Brian, the person, not the Airbnb, I'm intrigued as to what that would look like if you started to design that. I see a child. I see like a childlike curiosity and energy and love. that I think I've always held on to. I also see the world through this idea of family and community. And I think when people hear the word family, they think of their parents, their siblings, their children. And I think I see... My co-founder Joe, I asked him, what would success be for Airbnb? He had this crazy audacious idea, he said, to redefine the word family. and I've realized that like so much of my life has been trying to do that I see this like childlike person of curiosity and wonder that I've never left that sense of wonder that I'm open to be vulnerable and guided by love and like treating or wanting to treat those around me like family and what I mean by that is I try to do anything for them 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 I mean that's the iconography I would hope that iconography is true to some extent I guess as I think about it even deeper I've used the word loneliness connection and community but maybe at some deeper level the deepest word is family and what bonds, bonds family is love.

1:29:15And like, I think that like, as families have gotten smaller and smaller, we've gotten more, more and more isolated. And if we could re-expand that word, and maybe that's like too idealistic, but like just even a little bit to your like close friends and to other people and just try to like re-expand that circle. That's kind of what I would want. you know, if I design the world around me, then I better design it with other people in it. And as you see that, do you, do you see the child or are you the child? As you visualize that? Yeah, it's funny. I kind of see both. I see. Like, are you seeing the child sitting there or are you seeing the vision through the eyes of where you would be?

1:30:02I feel like a timeless image of myself. Like I, I'm like young and old at the same time. Like I can see the child of me and I can also see this like grown up that I always like that is protecting. And so I have like both sides, the protector offering security and bringing people together and the child who is vulnerable and seeks love and wants to just be open and totally curious. It's almost like I have this image, you know, like you said at the family, the dinner table where you like, like you as a kid with your parents, your siblings or whatever. My image is that, but it's a very big table with a lot of people.

1:30:44And that's not just my close family that I might have. It's maybe the broader people in my life that I have around me. That's, I think, the image I have. And I think that's in a space that's very well designed. Very well designed. And I have a design aesthetic that's fairly modern, but also whimsical. I don't like the cold. I don't like coldness of modernism. I like it to be like colorful. And so, yeah. I saw, if you're okay with that, I want to share something that came for me. To me, the clarity is that it's not even the merger often. What you said so beautifully was like, I see my younger self and I see where I am now.

1:31:27And now it's protecting, but the childlike is that love, that joy, 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. Oh, it's really great. 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. I've always wanted to believe that I can have the wisdom of my grandparents and the curiosity of a child. There you go. In one. That I have a foot. You know, Walt Disney, one of my other idols, used to, in the front of Disneyland, he says, here you leave the world of today and into the world of tomorrow, yesterday, and fantasy.

1:32:04He 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 oscillate between the two you know culture and technology massive scale become one of the biggest in the world with like desire to always be a startup and always be close-knit. It's like these two paradoxes, competing forces. Yeah, and I think that is a tension that I think it's a really interesting tension.

1:32:50Now you're making me think about all this. Some of this stuff I've never really, not only have I not talked about it, some of the stuff I've never really thought about until now. I'm just really thinking about it. One of the things when you run a giant company is you learn scale. When you start a company, you're tiny. You have to do everything.

1:33:13Things you don't even think about. You have an office, which is your apartment, and you need to buy a coffee maker and go buy the coffee, and you need to have a name for your company. You actually need to check if that name's trademarked, and you've got to have a story for the company. Then you've got to make sure you have a legal corporation, you have to interview the lawyers, and then you've got to actually decide what you're going to make. And you say, well, how do I make things? And I could go down the 100 ,000 things in the tedious details. And then if you go on a rocket ship that I go on, 15 years later, a billion and a half times it's been used, you end up at some massive scale, a scale that's bigger than you've ever imagined.

1:33:51But as a founder, you never let go of those details. It's like a founder is different than a professional manager. A professional manager never saw it small. And as a founder, not only did you see it small, you created what was small. 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 say, well, what about this? What about this? What about this? And go into the smaller and smaller detail. and then I go back to the present scale.

1:34:30It's like a satellite map. It's like the powers of 10. Zoom out to space, 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 it mean? You dive right in and you zoom out. And a lot of leaders, they struggle. They can only do that medium altitude. They can't see the fullest picture or they get stuck and they can't access the smallest of details. And the entire universe exists in the smallest detail. And that's what you discover when you zoom in and zoom out. You start to realize the relationships.

1:35:07And 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. Yeah, it's that balance between recognizing what's possible through scale but at the same time being able to be embracing of your own insignificance. Yeah. It's like you see the significance, but yet you recognize it's insignificant. Yeah. Paradox is where. It's so fascinating. Yeah. The paradox is the only thing that's fascinating. Yeah. You know, the human mind is a paradox. All of these, everything that we see that's magical about the world is a paradox.

1:35:42Everything's connected, but everything's doing its own thing. Yes. Right? Like the ocean and the sun are doing their own thing, yet they're connected, yet they're doing their own thing. And I think the more you start to see why I want to scale, you sort of see you're right, that more and more things are connected. But because everything's connected doesn't mean they're all the same. And the more you learn about the details of things, the more you realize how different everything is. And so you, but then you realize they're actually in some deeper way related and that you spend the rest of your life kind of in that discovery.

1:36:10Yeah. And you know what I've observed that is the connecting force, at least up until now in my life, is that everything that we've just talked about, everything in the universe that we see is serving uniquely. What connects it is that it's serving. The sun is serving. The water is serving. The trees are serving. The trunk of the tree, the leaves you talked about, the flowers, they're serving. Everything is giving a service. Everything's interdependent on everything else that we tend to have this illusion that we're separate from one another. And I think that even like loneliness might be 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.

1:36:56And 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.

1:37:26And if you don't see them, you have to keep looking. And then once you keep looking, that becomes the bond, that becomes the thing that you share between them. And how do you do that? With curiosity and interest. Fascinating. Just be fascinated all the time. And it's almost like that's contagious. If you're fascinated, I'm fascinated. Somebody once said that to me, a director who I was doing a film shoot. And he said, if you're fascinated, I'm fascinated. And I'm like, well, okay. Like I really do. And it's like, and so what, what do you find fascinating? Yeah. Yeah. I often say to people similarly that if you don't find someone interesting, it's because you're not interested.

1:38:07Yeah. Like you're not interested enough. There is something interesting about every person you meet. There is something interesting about everyone and everything. and that is, I think, what curiosity is. And you find the game within the game. You find in school, I think so many people in school, they're not interested in subjects because they're abstract. But if somebody's obsessed with basketball, then teach physics through basketball, teach biology through basketball, teach history through basketball. So 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.

1:38:40I had no abstract interest in learning about leadership and management and organization. I had no abstract interest in understanding 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 have stuck. And so Airbnb became that model. this world. And I have learned almost everything through this world that I've been generally constructing, co-constructing with my coworkers and with the community.

1:39:21And it's just like, I like to joke that Airbnb is like the world's biggest RISD project that just never stopped. And we just kept building it and kept building it and kept building it and kept building it. And the bigger we build, the more I learn and the more I discover. And yeah, I've seen so much of the world through the creation of this really big house, so to speak. Yeah. And that's pretty wild. It is pretty wild. And it's just getting started, hopefully. It's just getting started. Brian, this is without a doubt the most unique episode of On Purpose I think we've ever had. Really? In four years.

1:39:51No way. Don't just say stuff like that. You can check with these guys. But we end every episode with a final five. These are five questions I ask pretty much 90 % of them to all guests. and these are your final five, Brian. They have to be answered in one word to one sentence maximum and I will probably destroy that pattern, but we'll try. So Brian, these are your final five. The first question is, what is the best insight advice that you've ever heard or received or read? It's better to have a hundred people love you than a million people that just sort of like you. And so do things that don't scale.

1:40:33And if you do, maybe people love something you love so much, they'll tell everyone about it, and you might end up with millions of people after all. It's kind of a long sentence. 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? Anything that involves chasing status. Not because it's bad, but because it's actually a horrible way to even get it. Love that answer. Yeah. Question number three, how would you define your current purpose? To try to help bring the world together, even if it's in the end a small way.

1:41:13Question number four, if you were being remembered after you were physically gone, what would you hope to hear? You miss him. Our 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? Sometimes people ask me, if you could impose one thing on the world, what would it be? And I'd say everyone would have a passport and everyone would walk in someone else's shoes. And I think if they were to do that, there'd be like such a greater awakening in the world. So maybe everyone was forced to live someone else's life and to step in someone else's shoes and the more different, the better.

1:41:56Well said. Brian Chesky, everyone. Brian, that was, as I said, the most unique. I think it's really interesting, something that came to my mind and heart. And since this has been such an intuitive conversation, I feel I should share it. You know, in our professional life, we have business partners, but in our personal life, I don't think we often think about having human partners. And I really appreciate you dancing with me today, going there with me today and being human partners for each other. and you definitely did that for me today. You brought out of me things I didn't know that I haven't gone to for a while.

1:42:30So thank you so much for inspiring me and enlightening me in so many ways. I truly had a special internal experience myself. 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 absolutely thank you so much thank you grateful for you well thank you have me today thank you so much such an honor such a pleasure and everyone who's been listening and watching if you're with us then make sure that you i want you to let me know what was your favorite moment there are so many great moments but grab a screenshot of where you found your favorite moment so we can see all the seconds and minutes so that everyone can go listen to i love seeing what deeply connects and penetrates through to our community because this is all in service of you.

1:43:22So thank you for everyone who's been listening and watching. And thank you, Brian. Thank you, Jay. If you love 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. Look, am I hesitating on this because I'm scared of making the choice because I'm scared of doing the work? Or am I sitting with this because it just doesn't feel right yet? This is an iHeart Podcast. you