My whole life was chasing success because chasing success made me special, and special made me feel love. And a light bulb went off. I was lonely. I have an addiction, and that was to work. My happiest times in my life were when I was connected, and my most unhappy parts of my life were when I was lonely. But if there's one thing I'm great at, it's learning and learning how to become many different things. Loneliness is a subjective feeling. You have less connection than you need. That's all it is.
Welcome to the Midlife Chrysalis podcast with Chip Connley, where we explore how midlife isn't a crisis, but a chrysalis, a time of profound transformation that can lead to the most meaningful chapter of your life. Howdy, it's Chip Connley and this is the Midlife Chrysalis, and this is one of the episodes I've most been looking forward to.
For those who don't know my story, I joined Airbnb, the little tech company that most people had never heard of over 13 years ago, to be the in-house mentor to the founders and Brian Chesky, but also to very quickly learn that I was being mutually mentored by Brian. Brian was teaching me things while I was teaching him things. And I've got to say, at 52, with Brian being 31 and the average age in the company being 26, this is actually how I earned the term, the phrase, the modern elder. Someone who's as curious as they are wise. But I felt like there was a new definition of success for me, and that definition was defined by how can I help Brian and his co-founders be as successful as leaders as possible, and how can I help them build a company that can live far into the future. And at the time I joined the company, it was actually very small, and I spent seven and a half years there. Four years full-time, three and a half years part-time. Somebody who's listening to this episode, and I'm giving you the intro having already just shot, you know, we just recorded it, said, 'Chip, you sound like a proud papa.' And I do. I do feel like a proud papa. I'm proud that Brian is still, almost five and a half years after the IPO, still the CEO of this company that's a Fortune 500 company and hundred billion dollar company in valuation.
But I have to say that, you know, you're going to find in this episode that while we will talk about leadership and we will talk about tech a little bit, this is an exploration into Brian Chesky as a human and as a philosopher and as somebody who has evolved into his midlife. And I think it's one of the most transparent and authentic podcast episodes Brian has ever offered. And I guess that is a testament to the relationship we have. So I hope you enjoy it, and I will be with you at the end to express my three lessons I learned from this episode.
Brian.
Look at that hair. You got a lot of hair.
I know. I decided to finally grow it out.
Yeah. I like it. I like it. Thank you. Well, what can I say other than it was gosh almost exactly 13 years ago that we started spending some time together, and you came over to my house and wanted to convince me that I should be joining Airbnb, this little tech company that I was confusing with couch surfing. I didn't know what the hell you guys were doing. And I said I'll give you eight hours a week. You convinced me to run 15 hours a week, and within three weeks I was 15 hours a day, and I realized I'm fully committed to this. What was it like approaching me and people like George Tenet and John Donahoe, the CEO of eBay, who I did a call with today? You've got an amazing appetite for learning from people who have an expertise in a particular area, and you have complete chutzpah to ask them to help you. So tell us, go back to the time when you came to me, and why did you come to me?
Well, first of all, Chip, I want to start by saying it's so nice to see you. And every time when I look in your eyes, I have so many memories, including in this building that I'm in now. And even in this room we're in, I had meetings with you in this room, and I'm just, it's incredible. Let me start. Let me take that as two parts. The first is I had a lot of chutzpah. There's a lot of things I've struggled with in my life and I had to work on, and we'll probably talk about it, and that's not one of them. For whatever reason, I always had a nerve. I always was like shameless. I had this chutzpah to seek out the very best. And you know, when I was in ninth grade, that meant I sought out the seniors in high school, and when I was in college, I sought out the professors and got their time. And when I came to Silicon Valley, when I was not really very obscure, I sought out kids two years older than me, a little ahead of me. And you work your way up, and pretty soon I'm talking to you and these people. So, it's just a lifelong pattern I had. I realized like somebody once asked me, 'What is the main thing you've learned how to do since you started Airbnb?' I said, 'The main thing I learned how to do was learn.' I've learned a lot of things. I'm not sure what I'm an expert in. I'm a pretty good writer. I'm not the best writer in the world. I'm a pretty good speaker. I'm not a professional orator. I'm a pretty good business leader. I'm a good designer. I'm not Jony Ive. But if there's one thing I'm great at, it's learning and learning how to become many different things. And one of the ways I learned was I learned to go to the source. If you were to ask somebody, how do you learn something in 40 hours? They'd say they'd study it for 40 hours. Well, how do you learn 40 things in 40 hours? You can't spend 40 hours on everything. You have to basically be very efficient with your learning. And the most efficient way to learn I always found was to go to a source or authority. And for me that was seeking out. And I find that so many people, the biggest obstacle to their success is this voice in them saying I'm not deserving of this. And I always thought like it doesn't cost anything to get rejected. It doesn't cost anything for them to say no. And honestly I'm not going to take no as an answer, and I hope that doesn't offend the person. And I never took no from you. So, I heard about you because when I started Airbnb, somebody gave me your book. I think you wrote multiple books actually.
Yeah, it was Peak. They gave you a copy of my book, Peak: How Great Companies Get Their Mojo from Maslow.
Yes. Yeah. Okay. So, that was the book. And I remember reading it. It had a profound impact on me. And I took away from it a couple lessons. One was culture, but the other thing is hospitality. And I never thought what we did was hospitality. When we started, I thought I was an anti-hospitality company because I thought hospitality were hotels, and I thought we were anti-hotels. And then I realized that hospitality is just service with heart, and actually the boutique hotel movement was akin to my original mission, and that we actually had many hosts, hospitality professionals, and we had to teach them about hospitality. So that was the first reason I reached out to you. The second reason again is I was looking for mentors. I was looking for somebody that knew how to run a business. And what was different about you is I saw tech leaders, but the tech leaders didn't understand the business we were in. That we were not in the business of technology. We were in the business of hospitality, and that you were in the business of hospitality, but unlike people at Hilton and Marriott, you lived in Silicon Valley and you kind of were, you went to Burning Man, like you were of the Silicon Valley culture, that you were countercultural, and you were a Stanford grad, countercultural hospitality person that went against the big hotels. I used to say when I got into hospitality, I got into capital H hospitality, lowercase b business, and I felt like the industry we were disrupting was capital B business, and they had lost their sensibility in a new generation. And so that's why I sought you out. And the moment I met you, I honestly had an agenda, and I knew you were going to work here full-time, but I knew that you weren't ready. So I said, 'Fine, we'll go with eight hours.' And I knew you'd be full-time.
Yeah. You know what? I hope that's not total manipulation, but to be honest, I didn't know. And I was willing to take eight hours. I literally felt like when I met you at your house, this beautifully designed house, but I also love design. You have that koi pond. It was a beautiful house. And I think like a countercultural hospitality guy who's co-launched the boutique hotel movement and lives 12 blocks from me that wrote a book I read and likes design. I'm like, why? Like we're meant to meet and we're meant to work together. So that's why.
But it could have gone so badly. Let's, I mean, first of all, I didn't understand tech. And it turns out that I was a mentor and an intern at the same time because I was interning when it came to understanding tech and VC and millennials' travel habits. And I also could have had a really big ego, which I probably had a moderate-sized one because I'd run my own company for 24 years and 3,500 employees. And who am I to come in and be the mentor to Brian, but also report to a guy 21 years younger than me? So, I think in those first few months, we had to really get a sense of whether there was a rapport here and a mutual respect. And I have to say, because you had a real appetite for learning, there was a part of me that felt like you were upping my game to have an appetite for learning as well and to be as curious as I was, maybe wise. So, how was that though to have, did you ever have any worries that this former CEO in the hospitality business was gunning for your job?
No, because you did not seem like you wanted to be CEO of Airbnb. Maybe your reticence to work more than eight hours a week told me that the last thing on your mind, but also I don't think that you were motivated by power. I felt like you were motivated by other things. There were people in my past that I met with that might have been gunning for my job, and I might have been insecure and I might have avoided working with because it would have been a conflict, or my insecurity didn't allow me to let them in, and I never felt that with you. One other thing you said, like why did I take a chance on you? Well, you have to remember, and this is something I want everyone to remember, I went to the Rhode Island School of Design. And when I went to Rhode Island School of Design, I didn't go to MIT. I went and I thought I'd be an artist. When I met you, I met you I think like five years after I came to Silicon Valley, and I felt like I'm a tech founder, and five years ago I didn't know anything about tech. And if you're curious and a learner like me, then you can learn it because I can learn it. And frankly, I didn't want to build a tech company of only tech people. Especially because we weren't in the business of technology. Technology enabled us to be in the business of connection, belonging, and hospitality. And it was pretty weird to be in the business of hospitality and have no one at the company knew anything about hospitality. Like literally, we'd have a bunch of us young people. We were intuitive, but we had absolutely no experience about hospitality or all these different things. And it's like that'd be pretty weird to not have somebody. So I really had faith. And so I didn't think you wanted my job. I was pretty secure. I think you made me feel secure. And to be honest, I think what we had was a mutual mentorship.
Yeah. And I think that mentorships, like I learned from young people, and I've asked young people, they mentor me on social media. I've asked people younger than me to mentor me on AI. Like I think that if information and education only goes from one generation down, then the older generation stops learning. And I think that the mentorships that are the best are mutual. Like I'll give you another mutual mentorship. I have President Obama. President Obama, I have a relationship with. He started as my mentor.
Pretty good one. You're in good company.
He started as my mentor. But then not long after, you know, like ChatGPT launched and he was like, 'What is this?' And I started trying to help him understand AI. I introduced President Obama to Sam Altman. You know, and I would try to help him understand things. And he wasn't too proud to know, yes, I'm more accomplished. I'm older. I'm wiser and more balanced. I have more to teach you than you have to teach me. But it's a choice. It's a choice for him to say, I have the appetite of curiosity. And Leonardo da Vinci is my hero. Leonardo da Vinci might have been the most curious human of all time. And so I think that learning comes from curiosity, and that at any age we can choose to be curious, and that might be a recipe for youth.
So you were 26 when you and Joe started Airbnb, and then Nate joined you as a 24-year-old if I'm not mistaken. I was 26 when I started Joie de Vivre, my boutique hotel company. You're turning 45 this year, which is sort of now getting to the core of midlife. We'll come back to talking about midlife in a moment, but what advice at 44 now, 44 and a half, would you give to your 26-year-old startup founder that you've learned along the way?
That's such a good question. I think I will answer that question by prefacing that I think a lot worked out, so obviously so, like I shouldn't change too much, but I have learned some things. I had an impostor syndrome for a very long time, and I felt like, and it probably goes to a much deeper source, this, that maybe we get to, maybe we don't, why did I have an impostor syndrome? It probably had to do with my upbringing and all that. A lot of people do. I thought I was the only one that felt that. And it turns out that the best people often have that, and the best people are often the most ambitious people, and the most ambitious people often have something that was missing growing up, and that drove them, and hence there's some insecurity there. I think that's very common. And I would tell that person that was starting Airbnb that you don't need to be so afraid. It's going to be okay. I would remind myself of the wisdom my dad gave me. Things are never as good as they seem or as bad as they seem. I would tell that person that Airbnb is not a family. It's a high-performance team, because when people started resigning, my heart was breaking because that didn't make sense to me how you could leave a family. And it is like a family. We call the Airbnb family the Airfam, but it is not exactly a family. I couldn't make sense of that. And you don't fire family members. I would tell myself to not avoid conflict, as you know I was very conflict-averse, and that meant that I would avoid people that weren't succeeding, hoping they'd get the hint and resign, and of course they never did. And somebody once told me a pitcher never takes themselves off the mound, that the coach has to go onto the mound. And I was hoping the pitchers would take themselves off the mound. And what I thought was compassionate was cruel, which is I let them fail, hoping it would be self-evident to them, and eventually it was. And had I intervened, I would have either stopped it or helped them, and I didn't. And that came from insecurity, and it was probably ultimately a little bit selfish, and I didn't see that at the time. So I think I said differently, Chip, I think I was a very good founder, and I wouldn't give myself any advice as a founder, but I don't think I was innately a good CEO, and I would give myself advice as a CEO. Said differently, I had all the right instincts when I started Airbnb as a founder, how to build a product, do things that don't scale, be courageous, seek out mentors. I did not have all the right instincts to be a CEO, have hard conversations, be transparent, don't avoid conflict, etc., etc., etc. And so a lot of the things that made me a great founder, my insecurity, my impostor syndrome, my drive, became an Achilles heel when I became a CEO, because suddenly those things manifested organizationally. And my creativity and my ADHD was very good as a founder with three people. I remember one time we had lunch and you said everybody's like a murky aquarium. Well, that was probably my energy manifested organizationally. I don't think it's a murky aquarium anymore. And I think murky aquariums are great when you're three people. Actually, it's probably the best type of aquarium to have. It's probably really bad at 500 people.
So, you have evolved as a leader, and let's be clear for those who don't know it. So, you are, if I'm not mistaken, maybe the only creative who's a Fortune 500 CEO.
True. I think I'm the only, like the objective stat is I believe I'm the only person that went to design school in the Fortune 500. Some people might call themselves creative, but I'm probably the only person that professionally worked as an artist or designer in the Fortune 500.
Frankly, that was your upbringing. I mean, you know, there may be somebody who was doing that and then spent 15 years as a head of marketing or something, but...
Yeah, maybe. Maybe for the people watching, there's a lot of AI founders right now like Dario and Demis, and they were like chess prodigies and math prodigies, and I was like the art version. I'm not saying I was a prodigy, but I was like the precocious artist, and I won a national award when I was 16. And when I was 14, I was taking like college classes for art and design. So I was like the artistic track. I never thought that would lead to technology. I wanted to be like Van Gogh, Da Vinci, Norman Rockwell. Tech was accidental for me.
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So, and I remember when the first year you went to Burning Man, and you know, I was on the board of Burning Man. You said, 'This is what the world would be like if artists ruled the world.' And I just loved that line. It's a line I've used many times, Brian, since then. So, what was it about your upbringing, without, you know, you don't have to go too deep, but I mean, you and I have talked a little bit about this one-on-one, and you've been doing some really beautiful work and being very vulnerable as a CEO, or being vulnerable as a human lately, in terms of talking about your own, here's the guy who's, you know, the mantra for the company is 'belong anywhere,' who's acknowledged at times he feels a little lonely. Let's explore a little bit about the evolution of Brian just as a human, and who you are today versus who you were 13 years ago when I joined Airbnb.
I thank you for asking that question, and it's a, this, I'll have to be vulnerable now but also thoughtful about what I share. My childhood was, I experienced childhood was difficult for me. It was beautiful, but it was also difficult. And I often felt like I didn't belong. There's a lot of reasons why. One reason why, I won't go to all reasons. Here's a simple reason. I was developmentally, physically two years behind everyone else. In fact, my parents thought I had a growth hormone deficiency. They took me to endocrinologists because I was like the shortest, smallest person. And I hit puberty years after everyone else. And an endocrinologist said, 'You know, I'm like kind of normal size now, but I wasn't.' And they thought I'd be very small. And he said, 'No, he's just two, three years behind. There's just his growth plates. He's two years behind.' That made me like a little brother to my friends and to girls. Like I was the cute kid, but I wasn't the, you know what I'm saying? Like that's just one example. There were other things, but that's one of them. So I wasn't bullied. I was an outcast in school, but I wasn't on the in-group totally. I didn't totally belong. And so art and design became a bit of a refuge for me because I escaped. I escaped, and my coping mechanism was to escape and to escape into my mind of my imagination. It's why I fell in love with Walt Disney, because Walt Disney did the same thing as a child. In fact, Disney, the theme park Disneyland, there's a plaque that says, 'Here you leave the world of today and enter the world of tomorrow, yesterday, and fantasy.' I wanted to leave the world of today to any other world, but I couldn't physically do it. I didn't have a, I was a kid, so I did it with my mind. And art became a refuge. I also got love and attention from people by being special. And so I think that I developed a drive and ambition because I fell into a pattern of seeking probably conditional love from friends and society. And there's all sorts of reasons why that even happened, probably for a therapist to talk about. But I learned that if I perform and I'm special, I get love. And so that made me driven. It reinforced art and design. It wasn't totally unhealthy. It wasn't totally healthy. It's kind of in between. You know, there were some great things about it and there were some darkness about it. But that was my childhood. Me feeling like I don't belong, feeling like I have to be special for the world to love me. And the way to be special and the world to love me is I can escape into this world and be a special artist and I can get two for one. And that was what I did. And I was always a misfit. Like I was also an athlete. So I turned into a competitive bodybuilder because I was so small that I was insecure about my size. And I was introduced to bodybuilding. And bodybuilding gave me the ultimate power. If I could change my body, I could change my life. Suddenly my body would stop controlling me. It was a way for me to get control. But I was too muscular when I got to RISD. So I didn't look like the other artists. So I was kind of a misfit at RISD. But I was too artistic at the high school sports academy that I went to, Albany Academy, the sports academy, and I was an artist. And I was not hanging out with my friends drinking. I was doing nude figure drawing. And they were like, 'What is wrong with you?' So I was always like I had different feet in different worlds, and am I an artist? Am I an athlete? Am I this? Am I that? I got to Silicon Valley, Chip, by the way. I'm not an engineer. So I'm still a misfit. I'm a designer in tech. What am I doing as a designer in tech? I've always kind of, and so maybe a psychologist may say I created a company about belonging so I could finally fit in.
And how do you feel about, do you feel like a misfit today? And how are you doing with learning how to develop relationships?
I felt like a misfit until a few years ago, and I'd probably been lonely for much of my life, not all my life. And I'm generally a happy person, and people are surprised when I tell them this because I am generally happy and I'm positive and I'm optimistic.
Well, and you present as an extrovert.
Yes. And by the way, like my hero was Walt Disney, and so did he. And people said underneath the magic there was some occasional sadness and melancholy.
