Brian Chesky (co-founder of airbnb)
2023-08-24 02:16:43
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Welcome, welcome, welcome to Armchair Expert, Experts. on Expert. I'm Dan Rather.
I'm Monica Padman.
And tonight, on 60 Minutes, you're gonna learn all about Brian Chesky. Who is Brian Chesky, Monica?
Brian Chesky is the founder and CEO of Airbnb.
Uh-huh.
A company. we have partook.
Yo, God.
Many, many, many times. But guess what else?
What? It's my birthday.
Happy birthday. This is the 24th. August 24th, we celebrate the day of our Lord. on this wonderful day, some 36 years ago. A beautiful brown baby was brought home from the hospital into the loving arms of Ashok and Nirmi.
Yeah.
What she didn't know is that, eight years later, another little baby would be arriving and she wouldn't want to share the spotlight.
Happy birthday, buddy. Thanks. I'm so happy you were born and you're with us.
Me too. I thought I was gonna die yesterday.
Okay.
Because I realized I had been delinquent on my seizure medication. I was out.
Oh, and how long had you gone without it?
No, I just went to take it and I was like, I'm out. So I had to just go to bed and hope for the best.
And you made it.
I did, but I really caught myself. But for about 20 minutes, I thought, wow, what if I die tonight? Like really? And then it was weird. I was like, I wouldn't, I won't know.
Right.
How weird that I won't know.
See, you and I's brain work so differently. I would, my first thought would be like, if I don't have a seizure tonight, I don't know that I'm gonna take this anymore. Yeah, that's where my brain would go.
That's where I thought you were going. No.
I did too, right? It felt like a setup for that.
No, that's also not how it works. You have to like really taper off.
I regret not asking Brian his opinion on titrating your medicine without any medical supervision. This was a really, I don't think, well, I didn't know the founding or genesis story of Airbnb. And that's really fascinating.
He has quite a story.
He really has quite a story. And I really enjoyed talking to him. Yeah, me too.
Also, I guess, if you wanna go to hang out with Ashton and Mila.
Or Brian, he puts his own house up and you can stay with him. Yeah.
There's like all this cool stuff happening with Airbnb.
I wanna stay with Ashton and Mila. Me too.
I'm friends.
I know. I'm gonna sign up.
Let's sign up.
All right, please enjoy Brian Chesky. We are supported by ADT. ADT knows a lot can happen in a second. One second. your baby can't walk, then suddenly they can.
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It did. We always had ADT and-.
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Here I am. That little baby was protected by ADT.
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Wobby Wob, you built that yourself, using all the templates, yeah? I sure did. Yeah, easy peasy?
So easy.
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♪ He's an armchair expert ♪.
♪ He's an armchair expert ♪.
♪ He's an armchair expert ♪.
It's a brand new mic.
So I got a brand new, oh, that's good.
Yeah, what is yours? Oh, his is, so. these were just sent to us by Shure, and mine says Dan Rather, which is who I always identify as.
Mine says Miniature Mouse.
Miniature Mouse, which is her code name.
And Rob says Wobby Wob.
Oh, wow.
A very special gift, the armchair expert yellow. I'm riding high on these new microphones, so. I like this. But you asked what was the impetus twofold. Monica, and I liked to argue in my kitchen.
You drop a topic on us, and we're likely to be on the opposite sides of it.
It's annoying for most people around us, because they don't feel like arguing or debating.
They're not as passionate about these inane fucking topics, but we'll die over it. So that was one impetus, but then the other, really, from being in AA for so many years and hearing men share about their failures and how much I've learned from men's failures, and I thought, I'd like to host a show where we didn't talk about how you succeeded so much, but more about what have been your struggles. I think there's a lot more to learn from that than someone winning the fucking Super Bowl.
Yeah, totally.
That moment, there's nothing to really learn from. I'm not gonna get there. Yeah.
Not with that attitude.
No, well, that's true. We've already established. I don't have the attitude of a winner.
Well, yeah.
You couldn't be more in lockstep with what the ultimate thought is, which is, in general, on a Monday for a celebrity, okay, you're rich and you're famous. Did it fix anything? Generally, it doesn't fix much. You're at a curiously similar place in your life, right?
Totally.
I saw you talking, you were a guest at Stanford, and I was thinking of all those students there. You're it. You, Zuckerberg, whatever the handful of people, they're all trying to be you, and they have a fantasy of what being you will feel like. And it's probably a little inaccurate.
I think a lot of people growing up, they wanna be famous, they wanna be very wealthy, and a lot of people growing up wanna have status, and I've been thinking a lot about why that is. I grew up wanting to be very successful, and of course, there's nothing wrong with that, but I feel like a lot of us try to climb a mountain because we feel like when we get to the top of that mountain, something will be filled inside of us, and so long as we are climbing and looking up and knowing that only if I get there I'm gonna feel a certain way. Some of the saddest, most difficult periods in people's lives isn't when they fail, but when they get to the top of that mountain and realize they don't feel any different. And I felt that way after our IPO. I came to Silicon Valley literally with nothing.
Well, hold on, you had $1,050.. I happen to know your story.
Yeah, yeah, be careful, I know your story. Exactly. I had $1,000, and I had a piece of foam, rolled-up mattress that I had duct-taped in a ball in the back of an old Honda Civic.
And you were coming up from LA.
If I just go back a tiny bit more, I'm from upstate, New York. My parents were social workers, and I remember mom, she dedicated her life to service, and she said, I chose a job for the love, and I got paid. no money, so you should choose a job that pays you a lot of money.
So when I heard that, I thought, well, that is counterintuitive. My assumption from two social worker parents would be like, you've got to find.
something that gives you purpose. No, she's like, we were looking at those U.S. News reports of what jobs paid the highest. Anesthesiologist. Exactly, anesthesiologist, neurosurgeon, investment banker, and I'm like, I could do that or be an artist.
And my mom realized, oh my God, you picked the only job that's gonna pay less than a social worker. My parents were like many parents in the 80s, or even today, where I think it was like an age of ambition. I think the 80s was this idea of status and success, and I just struggled growing up. I always wanted to fit in, and I never quite did. When I was five years old, my dad got me involved in hockey.
We had this shared dream that I'd be Wayne Gretzky at age five, and by six, I realized I wasn't gonna get there.
Well, you were born in August instead of January.
Yeah, exactly. The odds were stacked against you. The odds were totally stacked against me. I actually went to a sports academy, like a military prep school, when I was 13 years old. And I remember having this feeling like I was living parallel lives, my extensible public life and my true life.
And the public life I was living was this life that everyone wanted to live growing up in upstate New York, which was to be a great athlete.
That's the road to status when you're young.
And that's the road to connection and belonging. And how do we feel together? How do we feel cool? How do we get status growing up? Sports is very tangible.
And the thing about sports, unlike, say, art, is it provides validation via the school. The other parents don't give you status, ensure you won when you're really good at music or drawing. Yeah. That comes much later. But sports is a thing people participate in.
It's quantifiable, you can measure it. There's a record. We know how good you are. Exactly.
And I think there's a lot of good things about sports, but I think that when it takes over your life and it's not meant to be what you're meant to do, I'm sure that's a lot of kids' stories. So I went to this military school. It was all boys. There was a girls' school across the street.
A sister school.
But the boys' school had 60 people per class. The girls' school had 20 people per class. Uh-oh. Those are not the odds you want. Let's say not that different from an all-boys' school.
And it was an intense experience for me. I had to get up really early and drive an hour each way. The other problem I had was, I remember I was 13,, 14.. I was pretty decent. I had an August birthday and I hit puberty really late.
Double whammy. You know, I remember ninth grade, I'm a hundred pounds. Tenth grade, I'm like 110 pounds. Like this trajectory is not working out so well. Around that time, I also had this other life, and that was a life of an artist.
When I was six years old, I asked Santa for poorly designed Christmas toys so I could redesign them. I loved industrial design before I even knew there was a term for it. When I was 10 years old, I was at a friend's house and his dad was like getting his backyard landscaped. His dad decided to do it himself. So he had all these architectural tools.
He had, like a T-square and a drawing triangle, and a compass and a protractor, all this like vellum paper. And so then suddenly I got into like landscape architecture when I was like 10 or 11.. I attempted to redesign the backyards of all my neighbor's homes. That was an unsuccessful consulting business.
No one wanted to hire a 10 year old.
So then from there, I got involved in architecture. I'm like a kid. I didn't even know these were really fields. And then I remember I asked my dad to buy some shares in Disney stock and we couldn't buy a lot. But the reason I wanted is, if you bought shares in Disney, you would get this thing called the annual report.
And the annual report, they would send this big glossy brochure with renderings of theme park drawings that hadn't come out yet. And what I realized is that so much of my life had these two parallel paths. The first was trying to fit into a world of other people's design. And in that case, that was like sitting still in a class, looking straight ahead. I probably had a lot of hyperactivity and impulsivity and I was very difficult with authority.
I was trying to fit in with athletics. I really struggled. And then I had this other life where, instead of trying to fit in, I was trying to almost escape to a world of my own design and imagination. And that was probably the closer thing to who I really was as a person.
Were you a kid that could sit in your room for hours by yourself?
Yeah, so I had unbelievable intensity around technical draughtsmanship. So I remember going to like the Norman Rockwell Museum in Stockbridge, Massachusetts. My parents are big Norman Rockwell fans. And I was able to, as a child, draw similar to that style, like very hyper-realistic. And I looked really small.
When I was 14, I looked like I was 12 and I could draw like a 22-year-old or something.
I just have to point out, you and I have absolutely opposite experiences in life.
Oh, really?
Which is I looked 16 and was 12.. I was 160 and 63 in ninth grade. Oh my God. But I had the athletic prowess of a 10-year-old. I was completely flipped.
People were underwhelmed by me. Not overwhelmed.
Well, you were babysitting kids your own age.
I was babysitting a child, my own age, and my dad was lying about it.
Are you serious?
Yeah, yeah, my dad's drinking buddy. He had a kid that was my age, but he wasn't from a broken, divorced home. So he hadn't grown up really fast. He was a little immature. They would have me watch him, but they told me, like, you gotta say, your two grades ahead, which worked when we were in different school districts.
And then we ended up in the same school district in the same class.
Oops, whoopsies.
Oopsies. Oh my God.
Okay, sorry, I interrupted you. But I was just struck by how completely opposite.
Yeah, no, it was really crazy. So I'm at this private school doing art and design the side. The problem is the private school is so small. We have like the same art teacher every single year, right? There wasn't big enough to have a department.
So my art teacher was the same woman from eighth grade to 11th grade. And what she focused on was pears. She had dedicated her life to painting a series of pears.
Still lifes of pears. Still lifes of pears.
Oh, pear the fruit. Pears. And at some point I just realized I need to break out. I need to do something else. And so I have this crazy period in my life where I'm 16 and I have, like a early life crisis.
16 was probably the loneliest, darkest period of my life, because I was finally hitting puberty. I was an adolescent. I didn't fit in. My whole dream was to be a hockey player.
Were the kids at the school cruel or were you just largely invisible?
More invisible. It was kind of like a little bit of a old money school. And my parents are social workers. The way you would have status, I would say, was either you came from money or you're athletic, or you were ingratiated by the administration.
10 of the 20 girls across the street.
I had none of the above. I was kind of known as the artist when that was not cool. I think maybe as an adult, there's something cool about it. When you're 14, I can assure you that does not provide any lifestyle perks at all. I remember I would go to do figure drawing.
Figure drawing is like new drawing and you do new drawing of women and you were like super cool. Then one day you'd have to do a new male figure drawing and your friends would- Think you were gay. Yeah, there was a lot of pretty funny stuff that would come up. Maybe it's 1998 and I was pretty lonely. I didn't have a lot of friends.
I didn't know if I was a hockey player, artist or something else. And I wanted to be something. Being myself wasn't an option. I had to be something that would give me cash and prize and tension. And that's kind of the way I grew up.
And I just felt pretty lost. And I had decided that I didn't want to be at that school anymore. And now it's 11th grade and I leave that school. And I transfer to this public high school.
Oh, Jesus Christ.
This sounds like a terrible idea. And like the end of 11th grade.
Senior year.
Yeah, yeah, yeah. So you have like the jocks. It's all sorted. You have the kids in black. You remember all those like late nineties movies?
Oh yeah. Like, you can't hardly wait. By then. those are like 11 or 12 years of cliques that had risen up. And I just go in and I'm like, who am I?
You kind of had to pick a group. Am I a hockey player? Am I the like really cool kid? Am I the drug kid? There really wasn't like a creative group.
But I go to this school and I meet and our teacher changes my life. Her name is Miss Williams.
Shout out Miss Williams. Shout out to Miss Williams.
By the way, I'd felt like a failure already at this point in my life, which was kind of weird. I didn't feel successful. I didn't feel like I had made anything in my life. I didn't know who I was. I didn't know what I wanted to do.
I was invisible. And Miss Williams, unbeknownst to me, saw my artwork and told my mom, she said, one day he's going to be like a famous artist. Which made a big difference because it alleviated my mom's concerns that I would live in her basement.
Yeah, famous artists make money.
Well, normally posthumously, but that's.
He didn't have to say that. Exactly. And she really wanted me to make money while I was alive. So that was like, okay, shit.
She didn't want money for your estate. Exactly. The grandchildren of the artist.
No, she's like, we gotta get paid now. But she gave me the confidence to follow my passion. At 16, I had this profound thought. I said, I'm going to decide to be happy the rest of my life. If I do what makes me happy, and I do with people I like, then I'll be happy the rest of my life.
And what would make me happy at that time was drawing and art. So I applied to the Rhode Island School of Design.
Which you guys were saying, RISD? RISD.
RISD. Very famous.
Yeah, I know they were saying it in this interview at Stanford, as if it was as popular as Stanford. When I heard RISD, I'm like, how the fuck are they spelling that? And then I realized it was an acronym.
Rhode Island School of Design.
But an acronym where we're choosing to make RISD its own word and then D stand alone. Yeah, yeah, yeah.
So it's a pretty unusual.
I have objections.
Yeah, yeah, I think we need to think about that, RISD.
For the dyslexics, it's hard.
Yeah, exactly. And when you submit there, you're just putting your portfolio forward. You send them a bunch of your artwork.
It was actually really funny because I remember I was gonna study for the SATs, as I thought, oh, I need to go to some Ivy League school and I'm gonna need really great SATs. Then I realized, wait, at art school, you don't need very high scores. So I totally changed my focus on a portfolio. And so you have to submit a portfolio and then they used to have this thing called a drawing test. Ooh.
I guess it's to make sure they were authentic drawings of yours. And so you had to get a certain type of piece of paper and you had to do these three drawings, I believe. One was of a bicycle and then there were two other drawings. And then you had to fold the drawings a certain way and you had to put them in this special size envelope. They were very specific instructions.
Oh my God. And you had to mail in the drawing test.
It's like early encryption.
Yeah, exactly. That was their authentication method. And I kind of decided I'm gonna go to RISD or I'm gonna go to college, but I'm not gonna go to any other art or design school. But I didn't really know what I wanted to do. And I got into RISD and got a scholarship.
They didn't give a lot of scholarships and this made a big difference because obviously RISD, even back then, was very expensive. So I decide to go to RISD. It's like this freeing period of my life. I gotta tell you one other story. It's 1999..
I had this fear of going to art school because I realized, wait a second, I'm kind of an artist, but I'm also kind of like sports.
Well, you don't like the cure. You're not emo. You're missing some of the components.
Yeah, I had other interests. And so I felt I wasn't sure if I was ready to go to basically what was essentially a graduate school, where I was like picking a narrow field. So I get to the Rhode Island School of Design. This is a beautiful campus, but there's no sports. I'm not gonna be able to fit in.
I don't know anything. I didn't fit into high school. Now I'm gonna go to art school. I don't fit in. There's no environment.
Man without a home.
And then I find out that they had only one sport. It was a club team. And the club team was a hockey team.
Get out.
But that's not the crazy thing. And I said, well, what's the hockey team's name? And they say, oh, you haven't heard of the RISD Nads?
Like gonads.
That's what happened in 1960..
What?
No, no, no. This story, this is where the story gets interesting. I have never talked about this publicly. If my team was here, they'd probably bust down the door and slap a man. So here's what happens.
I'm like the RISD Nads. They said, yes. In 1963, three art students decided to create a sports team and they decided to name the Nads. And the fans cheered. They go, go, Nads.
Oh, wonderful.
It's a fuck you to the sport. Totally. Yeah, participation.
So I joined the RISD Nads. Yeah. My freshman year was a co-ed hockey team. Fuck yes.
Here's where we start, considering that you live in a simulation.
Exactly. The story is gonna get a little weird. So I just wanna forewarn you. This is gonna get a little bizarre.
Do you mind if I take my pants off?
You know what? I went to RISD. Well, once it's called the Nads. Honestly, people would do that in crits. So it's freedom of expression.
That's what we used to call it back then. Actually, free speech used to be freedom of expression. It used to be a very progressive value. 20 years ago. At RISD, that was everything.
Like, I need to be able to speak.
It was just like a very different political environment. But anyways, halfway through my freshman year, these two seniors decide to go away to this thing called winter session. They go to Amsterdam and they just kind of disappear. And so me, my friend and my RA, who's like a year older than me, take the team over. And we have this vision to create an international sports franchise out of an intramural hockey team.
And we took over a team that had a perfect season, Owen 16..
Oh, wow.
Who are they playing against? There's a co-ed league?
Oh, yeah, yeah. So we weren't allowed in any like official leagues. So we had to create our own league. Instead of playing for the Stanley Cup, we played for this thing called the supportive cup. Okay.
And we would have United States Coast Guard, the Mass Maritime Academy, Clark College. And we had this co-ed cheerleading. They were called the jock straps because they support the NADs.
Oh, my God.
The whole thing's a bitch. Yeah, yeah. And the craziest part of the story is back in the late nineties, there was this mayor of Providence named Buddy Cianci. There was a whole podcast series about him called Crime Town. Yeah, yeah.
I believe I've heard it. I don't want to overgeneralize, but nearly everyone in Rhode Island was corrupt in the eighties, nineties, right?
Providence had the third largest coast in Oceania country after New York and Chicago. Apparently, the Crime Town podcast basically says that he runs for mayor in the seventies on anti-corruption, anti-mafia, but of course doesn't have enough votes. And then kind of joins the other side. Pivots. He is, you know, a mayor in the eighties until he goes to prison.
He gets out of prison in the nineties, develops a popular radio show and something remarkable happens. He gets reelected mayor and actually revitalizes the city of Providence. They call him the Prince of Providence. So he controls the police. You know, he's the mayor and he's maybe mobbed up.
and who knows. And I thought to myself, that's exactly who we need as a hockey coach. And so one of the members of our hockey team goes to city hall with a jersey that says Cianci 00.. And we said, mayor, we want you to be our coach. No.
And he decides to be our honorary coach. He comes to games in a stretch limousine with big seven foot Mounties and women in fur coats with cameras. And I remember the first thing he said is, I don't know shit about hockey, but I always find a way to win. And I thought this is the kind of leader that we need. We basically would hold parades.
We didn't need permits. You got the mayor behind you. And that was, to be honest, my first startup.
Sure. Absolutely. You have a vision. You're putting together a team. You're trying to execute.
You got some management duties. Although you did mention that they had a perfect record. Did the record suffer under your grand vision?
My grand vision, it got a little messier. We did win a few games here and there. A little more pageantry. Yeah, exactly. But we were more performance artists than athletes.
You know, we had this funny logo that people can Google, the RISD nads. And we had a mascot that you can imagine. It was like an inverted Mickey Mouse. So the whole thing was like pretty. Very genitalia centric.
Exactly, exactly. I would have loved it. RISD was basically an environment for pranks.
Yeah, this would have been a great school for me to go to.
Yeah, you would have loved it. I regret not going there. You would have loved this. But I remember feeling, when I got to RISD, two other feelings. The first feeling was anything is possible.
Because in my high school, the word disruptor is like cool. now, I guess. Yeah, no, no, no. Not cool in the 90s in high school.
I know, I spent a lot of time in the principal's office.
Being anti-authority does not provide a lot of value when you're like in high school. So at RISD, I remember a teacher said, you're a designer. Everything around you is designed by other designers. You can design the world you want to live in. And I thought to myself, that is a crazy thought that I can live in a world that I design rather than a world that other people design, that we inherit one world, but we can leave another.
It was totally different than anything I had heard growing up. But I also had this unfortunate realization. I was into painting and drawing. When I was at RISD, I felt like I was maybe born 100 years too late for what I wanted to do, because I loved illustration and painting and drawing. But I noticed that photography, even back then, was almost all magazine covers.
Even the late 90s were photography, not illustration. The market was smaller. There was a supposed thing that Jean-Michel Basquiat said to Madonna. He said something like, I envy you because you make music for everyone and I make art for rich people. And maybe he never said that, but I thought the story summed up how I felt.
I wanted to make something for somebody else. Halfway through my freshman year, you have to pick a major. Can you imagine? You're 17,. you have to decide, I'm going to art and design school.
Now you're 17 and a half. You're like, okay, what type of art and design? Are you kidding me? And so there's 18 majors. There's like architecture and graphic design and painting and ceramics, and jewelry and metal.
And then there's a teacher. He's a department head for this field called industrial design. And he says, industrial design is design of everything from a spaceship to a toothbrush and everything in between.
Yeah, I think Steve Jobs made industrial design kind of ubiquitous. But pre-Jobs, this isn't something your average person even thinks about.
No, I think that, like the late 90s, you might remember, Target had a bit of a design renaissance. The Volkswagen reissue was kind of interesting. But really, Steve Jobs and Johnny Ive, we'll come back to later because I know I work with him. They really created what I felt like was a design renaissance. And so I went into industrial design.
I ended up spending also a semester at MIT. I remember somebody once at RISD said, art is a question to a problem in the world and design is the answer. And I said, I want to be part of the answers. I love that art makes you think, but I want to try to help solve problems.
While we're saying cool shit, can I tell you one I read last weekend? There is a famous Michelangelo quote that he probably didn't say. But the question was, how did you make this perfect sculpture, David? And he said, it was very easy. I just took a piece of marble and I chiseled away every piece.
that wasn't, David. I mean, fuck me, isn't that? That would have hit me. I was reading, I was like, my God.
Steve Jobs had another quote about design. He said, design is the fundamental soul of a man-made creation that reveals itself through subsequent layers. And I think those quotes mean the exact same thing. That a lot of our design is a process of not inventing as much as discovery. That you're feeling and you're discovering and you're revealing something.
And it was always there and you're peeling back the essence. A lot of people think great design is simplicity, but I think that a lot of people misunderstand what simplicity is. They think simplicity is removing things. No, simplicity is about distilling something to its essence. And to distill something to its essence, you have to understand it so deeply.
The first principles, what's the history? How does glass bend? Why are we doing this? How do we make fewer parts? And that's what the Apple products were.
The design renaissance of that period.
Yeah, a Rolex is not simple, but there's nothing extraneous there.
It's very mechanical, utilitarian. I think that's a lot of what great design can be. It can be a lot of different things. But Apple, there was like a soul and a spirit to these products. They almost felt alive, sentient.
To be honest, they felt like they were gonna be friends to these people. that were quite lonely.
We should also get to that, because.
Yeah, that's where we're gonna land.
Yeah, yeah. So I'm at RISD.
Are you attracting any girlfriends at this point?
No, I like to joke that not only did I not have a date to go to prom, I ended up going with my friend and his date. My prom photo is one of my best friends, his date, and me holding him, holding her.
So.
That's my whole life.
I get it, I totally get it. So to answer your question, I was super cool. Okay.
Exactly. Sorry, I have a question. I've just been hanging onto and I really need to know. Yeah. What did the bicycle look like that you drew?
I think I drew from direct observation some mountain bike that I would have had, that I would ride around. But it was super realistic? Yeah, it was very realistic looking. Okay. And I was kind of a realist, surrealist artist that mostly worked in charcoal and graphite, somewhere between Rocco and Adali, where it was representative scenes, but with a little bit of surrealism and bending of time.
Okay. I think I was very strong technically, but I don't know if I was a great artist growing up, because I don't know if I yet had anything I wanted to say. I was kind of obsessed with the medium. I was obsessed with the technical ability to be able to do or say something and have a kind of mastery. Weirdly, I never really felt like an artist until I started a business.
And it's almost because I was so naive, because I didn't go to business school. I didn't know how to run a business, that I started approaching it more intuitively, less mechanically. No one taught me how to do anything. So I just started feeling it. That became how I started approaching business, that I approached it the way an artist or designer would, which seemed so counterintuitive.
But again, Apple and Steve was kind of like that, right? Steve used to say, he said to the intersection of technology to humanities. I loved Walt Disney growing up. And the man, Walt Disney, he was also like a futurist. He was a creative person, but he was also a technologist.
He had this TV show in the 1950s called Man in Space. Werner Von Braun was one of the original members of NASA Research, and they basically popularized space travel before the 60s. And so there was this long lineage of. what I felt like were technologists that were also creative.
Borderline sci-fi people.
Yeah, yeah, yeah. And Steve and Walt were kind of like my idols. Of course, I didn't think I could grow up ever being like them, but I'm like, I'll work for somebody like that or work at one of those companies. And so I graduate RISD, but of course I made this promise to my mom that I would get a job. that was a real job.
And of course a real job was one that had health insurance. So I get to Los Angeles, it's 2005.. I convince my friends from RISD to move across the country with me. We're living in West LA, Whitley Avenue, off Bundy and Wilshire. Okay.
What year? 2005,, 2006..
I had just left that area. 2007.. Yeah, yeah, I got my first house in six. I was at Santa Monica Boulevard in Euclid for 10 years.
I was at Santa Monica and Barrington.
We were all in the same area.
That's very close.
Similar area. You were on like the nicer side of the tracks. Yeah. I was on the West LA side, but it was still really cool. And I got this funny job as a industrial designer at this very, very small firm.
And we worked with like entrepreneurs, basically no budgets. And I was doing all these interesting projects for all these different entrepreneurs that have these crazy ideas. And I had to design and create the strategy and the website and the marketing and distribution. The more services your boss could sell, the better. And that's actually really good.
for being an entrepreneur. You get to try a lot of things. And one day my boss comes into work and he says, you're gonna be on a reality TV show. And I'm like, what? And it turns out that Simon Cowell had the American Idol back then.
That was like the hottest show on television. And he wanted to create an inventor show, which was a spinoff called American Inventor. It was basically a precursor to Shark Tank. And then each contestant would get $50,000 for an invention, an idea. And they have to hire an industrial designer to make a prototype.
And the best prototype would win and the winner would have their product manufactured. I basically was one of the designers that they hired.
Right, you're like the dancing coach in Dancing with the Stars.
Yeah, exactly. Yes, I was the dancing coach without as much status. And I ended up getting paired with a magician who had an invention for a better toilet seat. And, of course, as you know, on reality television, they often choose colorful personalities. Yeah, of course.
And this magician was a very interesting client.
Wild, would we say?
Very wild. Magicians are a breed. Yeah.
We've had a few of them. Yeah, they are.
But there's different, like Vincent, is also a magician.
Oh yeah, I would say he falls under that.
What do you want to say about them?
There's a vibe and there's a in your bedroom for a long time practicing. I think there's some perversion. No, I'm not saying that poorly. Well, there's some control. There's an intuitive perversion about tricking people and a giddiness about, yeah, there's a type.
Sorry, all magicians.
Exactly, exactly. So, but he had this idea to invent a better toilet seat.
I mean, there you go. That's a little perverse. That's your invention. is a toilet seat?
Exactly, a toilet seat. Yeah. And so here I am on national television, designing a toilet seat for a magician. And I thought to myself, I thought the RISD professor said I can design the world I want to live in, and now I'm designing a toilet seat for a magician. This is a little different than what I thought.
You know, the iPod was the most popular product in the world and I was making toilet seats. And I'm like, I'm going to design the iPod of toilet seats. It was called the Pure Flush. He wanted to call it Flush Pure. I thought that was a little bit unseemly as a name.
He insisted on the words pure and flush in them. So at least I convinced him that Pure Flush is better than Flush Pure.
I agree. It sounds like you're flushing purity down the toilet.
Yeah, exactly.
Which we would never want to do.
Whereas a Pure Flush is a pure toilet. He's like, Flush Pure, you apologize at the end.
What problem? was it? solving, shit streaks, or? I'm being sincere.
His mother apparently had some respiratory illness and he claimed that when you flush the toilet, there's this plume of bacteria that gets in the air. Oh yes, we've heard about this poop particles. Yeah, poop particles.
That get on your toothbrush.
There was articles about this. Yeah, yeah, I don't know anything about this, but it was like a sealed toilet seat with carbon filters.
Oh, fuck. Yeah. That sounds kind of cool.
I do want one.
It was also like a toilet seat as a device.
Yeah.
Not everything needs to be a device.
No, although as the owner of a Brondle and Totos are nice as well, I do love that my toilet seat is, I've got a remote and I spray, and it's one. I do like that.
Ours didn't have any of those features.
Right, it just had some air purification.
It just had air purification.
It was questionable whether that was necessary.
Who knows? But then I'm thinking to myself at one point, what's the difference between me and these people? Like they're building businesses and I am designing toilet seats.
You're carrying out their vision.
The difference was that they're pursuing their dream because they took a chance, and I hadn't yet. And not since the Rizzy Nads, I hadn't done anything audacious. I was now institutionalized. You know, the movie Shawshank Redemption. Do you remember the older inmate who leaves prison and he like, because they say what happened to Red, he got institutionalized.
He got so used to the institution, an entrepreneur has to change or challenge an institution. And when you get too used to or too conforming to an institution, you get what I would describe as institutionalized. And I remember my life was like, I'm driving in a car as a metaphor, and the road in front of me looks exactly like the road behind me. I could see the rest of my life in the distance. And I think for some people that would have been reassuring.
Stability, safety.
And for me, all I thought about was like,
you blew your one ride on planet earth.
Exactly. Yeah. There's no adventure. I can literally see the end of my life disappearing into a horizon. I might be 60 years from now, but the road disappears.
And I remember at that time, it's 2007, a biography about Walt Disney comes out by Neil Gabler. And I pick up the biography and I read it, and it changes my life because Walt Disney had moved from Kansas city to Los Angeles with nothing at the age of 22 or something. And to me, the Hollywood was actually Silicon Valley. because I felt like in 2007,, the gears of the world that were turning the world almost felt like they were in Silicon Valley. Google was rising and Facebook was growing.
YouTube had just come out. I discovered videos about Steve Jobs on YouTube. I watched all these keynotes. And the reason I only watched the keynotes? because I was interested in design.
I was actually more interested in Johnny Ive. I didn't even know who Steve Jobs was, to be honest.
Is Johnny Ive the guy that helped him design also?
Yeah, he's the British guy who says aluminium, not aluminum.
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Yeah, yeah. And he's one of the great industrial designers of the last hundred years. I mean, he maybe defined the function in the modern age. Most people give credit to Steve.
I've read his biography and I forget the order of events. He had designed some products that Steve himself had an emotional attachment to. Like. he already knew that guy could execute his dream.
Stay tuned for more Armchair Expert, if you dare.
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So at RISD, I had a friend named Joe Gabbia, and Joe ran the RISD basketball team. So we only had one sport. Joe comes to RISD the year after me. He's a basketball player. So he decides to start a basketball team.
Yeah, these bozos can have this stupid hockey thing. I can't get out.
So we were the RISD Nads. So he created a team called the RISD Balls. And their tagline was, when the heat is on, the balls stick together.
This whole school's just one big genius joke.
The whole thing was basically a prank. And so what ends up happening is we become kind of rivals because we're kind of competing for fans. But then we're friends too. By graduation, I remember Joe telling me, he says, Brian, I think one day we're gonna start a company together. We gotta team up.
And right after RISD, we did this weird internship where RISD created this little design firm. And this company hired us, Joe and I, named Con Air. Con Air is the hair dryer company. Right, right, right, sure. And the Con Air hired us to design a new hair dryer.
And Joe and I got carried away with the project and tried to design a new strategy.
Balls in a dildo.
I love where you're going.
It was called the Blow This.
Yes, exactly, exactly. But Joe and I basically tried to design like a new strategy for the company. And we also created this thing called the Soap Shirt. You put it on, you wash it off. Wait, what?
Yeah, yeah. So the last day of the internship, I have to present to the executive team and we do this presentation and no one says anything. At the end of the presentation, the CMO of the company, his name's Marty, he says, you drink too much coffee. And that was all he said.
That was the nicest thing he could muster.
Yeah, yeah, exactly. So fast forward to 2007,, Joe moves to San Francisco. And one day, I get a package in the mail and I open the package, and there's the design of a C-cushion in the shape of human buttocks with a handle on it. And so I want you to imagine like two half circles.
An imprint of a butt.
But an inverse imprint, like an extrusion of a butt.
Okay, so almost breasts.
Yes, and it was called Crip Buns. And it was actually this really cool product that's incredibly well designed that ended up in the Museum of Modern Art gift shop. So it was an art school thing where you just sit on the floor and you get charcoal on your butt. So he decides this like C-cushion. He writes me this letter.
In the letter, he basically describes that he had started a company manufacturing C-cushions. It was selling. And all of a sudden I realized, wait, Joe is like these people I'm working with. He's an entrepreneur.
This is like when you see a friend in a band and you're like, well, shit, I could be in a band.
In Joseph Campbell's Hero's Journey, he wrote a book called Hero of the Thousand Faces. And he said that basically every character in a movie, whether it's Star Wars or Hunger Games, a main character, leaves their ordinary world. They cross the threshold to a new magical world where they experience transformation. The person they were dies. They're reborn, going back to the world they came from, an elevated version of themself.
In order to go to this magic world, you need this thing called the call to adventure. And you initially refuse it. This was my call to adventure. Joe says, come to San Francisco. Let's start a company.
And I initially refuse it. I said, no, I'm not gonna do it.
Was that your ego? Like I, would be joining his thing.
I think it was fear. I had this inner desire to be an entrepreneur. I never knew an entrepreneur growing up. The only entrepreneur I know was like Bob from Bob's Pizza. One of my friends, his dad, had a bronze baby shoe company.
I did not think an entrepreneur was an available option to me. I don't even think I heard that word in my childhood,
the word entrepreneur.
I think a lot of kids, they only dream of what they're exposed to. And I think a lot of people tell you follow your passion, but I think that's very difficult, because what do? you haven't found it yet? And I think a better piece of advice may be follow your curiosity and you have to be very proactive and very curious. But luckily I was exposed through industrial design to entrepreneurs.
And so all of a sudden I had this moment in my life where I go into work and I quit my job. It's just totally impulsive. I don't have any money, obviously, we haven't saved anything. And I then go home and I tell my friends who have convinced to move across the country with me that I'm bailing. And I'm gonna go to San Francisco with basically $1,000 the bank, because I was making probably 45, $48,000 a year.
So I get $1,000 a week and I was kind of living paycheck to paycheck. So I probably had like $1,000.. I'm now 25, turning 26.. I'm sure, like you all have had a decision in your life and then everything after changes. It's almost like you went on a different tree branch and it's just this whole new world change.
You get off at an exit.
I never look back. And I get to San Francisco and Joe tells me we have a problem. The landlord has raised his rent 25%. Oh boy. And we could barely make rent before.
But it turns out that that weekend in October 2007, an international design conference is coming to San Francisco and all the hotels on the conference website they're promoting are sold out. And I remember we had an idea. Joe writes me an email. He says, what if we just turned our house into a bed and breakfast for the design conference? Wow.
If we do that, then we can pay our rent. And I said, this is an incredible idea. but how are we gonna be a bed and breakfast if we don't have beds? He opens his closet and in his closet he had a bunch of air mattresses. So he pulled the air beds of the closet.
We inflated them. We put them in the living room floor and one of the extra bedrooms and we realized it's not a bed and breakfast. It's an air bed and breakfast. Wow.
That's amazing.
Wow.
That's where the name comes from.
I did not know that. Air bed and breakfast.
You know, Airbnb was like the world's largest RISD project. that just never stopped. It started as a prank and it was almost like. this is completely absurd. So we build this website in three days.
It's air bed and breakfast. We used to say, come stay at Joe and Brian's original air bed and breakfast, established in 2007.. And we wanted to make ourselves sound old, even though we're reusing the year we were in. I'm, like, you know, most tech companies want to sound new. We want to sound old.
We're like, we're a bed and breakfast. We've been in operation for like four days. We even tried to like make a little bed and breakfast sign. We ended up hosting three people that weekend.
When I heard this story, my immediate curiosity was, so great, you come up with that plan and you design this website. Do you connect with the promoters of the conference to get on their website? Because I'm like, how do you reach these people?
There were these design blogs that cover the conference. Okay. I mean, I didn't really know anyone there, but Joe, because he had made Crip Buns, he had emailed all those blogs. they had written about his current product. And so we emailed the same people.
And people were charmed by this and it got an inordinate amount of activity.
And they needed a place to stay.
I remember one night, Joe says, before we go to bed, I'm going to email these design blogs. I wake up the next morning and all of a sudden four design blogs had covered us. They had a photo, a paragraph of text. At this point I said to Joe, we're like the Beatles.
Right, right, yeah.
I had no proportion. It's like if you're lucky enough to get on the news when you're younger, you're like, well, I'm a movie star.
I'm a movie star, yes. And so we ended up having these three people stay with us. This woman from Boston, a 30 year old guy from India, a mall serve, and then a 45 year old Mormon, father of five from Utah.
No kidding. What a rabbi.
It was the craziest thing in the world. There's something sacred about when you bring somebody into your home, something amazing happens. They're vulnerable. So they're putting their trust in you and you see their vulnerability.
Well, it's a huge leap of faith by both parties.
By both parties. And it's this commingled where you feel like your life is on display through your house. And they feel like an outsider's vulnerable that's entering your home. Two people could be in a highway. One cuts them off.
Another person looks at them and gives them middle finger and says, I hope you die. Those same two people in a different context, one could be taking care of the other. I think that we were so young and naive that we were so naive to believe this was a good idea.
Well, by the way, your youth is a huge component in this.
100%. When you're like 35, 40,.
you create a comfortable enough life for yourself. You don't want any kind of disruption to that. Totally.
I think that one of the best cures for loneliness and unhappiness is to thank other people, give gratitude and serve other people. It's counterintuitive that, like doing things for others, sometimes you get more emotional benefit out of it than they do. But I also think that when Joe and I, and then Nate, started Airbnb, I was naive because we had this idealistic vision that people are basically fundamentally good and we're 99.9% the same. And I think I was just young enough to believe that. And I remember telling the first person I told about this idea.
He said, I hope that's not the only idea you're working on. People said this will never work. Strangers will never stay with other strangers. 1.5 billion people later. That's how many times Airbnb's been used.
Airbnb is, I think, in as many countries and more countries than Coca-Cola. On a typical night. in 220 countries and regions around the world, we have the population of Los Angeles, 4 million people staying together from countries that never stayed together. And so we have data on how humans live. Yes, sometimes things go wrong.
But the thing that surprises me is how statistically infrequent those are and how things go right. I remember hearing a story in 2012,, and this summarizes it, I'll never forget. A guy named Sebastian comes up to me. He said, there's a word you never use in your website. That word is friendship.
Six months ago, the London riots broke out outside my room and I was very scared. And the next day, my mom called me to make sure I was okay. And he said, here's the interesting thing. Between the time the riots broke out and the time my mom called me, it was a 24-hour period of time. And in that window of time, seven of my previous Airbnb guests called me just to make sure I was okay.
He said, think about that. Seven of my guests called me before my own mother did. And I think that is not how it works every single time, but if we could just realize that the other is not so other. People are mostly fundamentally good, that we are statistically 99% the same. And we spend a lot of energy, both good and bad, trying to distinguish that 0.1%.
We might, at our best, call that diversity and celebrate it, or at our worst, say they're other and they're hateful. How could you hate someone who's 99.9% the same as you? And I think we live in this illusion, not that we think we're better than other people, but that we're separate from other people.
In AA, we call this terminal uniqueness. Yes.
What Airbnb has taught me by building a global travel community is in some larger sense, everything's connected. Every one of us is connected. I mean, obviously there's individuality that I think is really great. The sense of personal freedom and empowerment. in the United States in particular, that has allowed a lot of social economic mobility.
I'm probably a great case study of that. But the other side of the coin is that you don't want to do it alone. My high school yearbook quote was, I'm sure I'll amount to nothing. It was partly a joke, but behind every joke is probably some seriousness. But I also desperately wanted to be successful because I wanted what I thought was love.
Now it was conditional love. And it wasn't actually love, it was probably adulation.
Slash envy.
Yeah, yeah, exactly.
Slash. I can get close enough to get some of this.
Over the next 10 years, Airbnb took off. And we, probably alongside Uber and a couple other companies, became the startups of the 2010s. We made more money than we ever thought we could. Everyone I went to high school with knew what I did. And I felt like I'd achieved everything.
Then we go public at a hundred billion dollar valuation. Now I'm a designer that went to RISD, whose parents are social workers. And to me, a million dollars is a lot of money. A hundred billion dollars was a number. I had trouble.
Sure.
That's a made up number.
Yeah, at some point it's just like a made up number. And you'd think this is gonna solve every problem.
Oh, absolutely.
And I had this image that if I got successful, that I'd have all these people around me, have all these friends, I'd have all this love, all this everything and my life would be fixed. And the crazy thing is, Airbnb initially started as like a family. You know, I was single, I didn't have a family. So Airbnb became the family I did not have.
There's three of you that founded it?
Yeah, but as we got more successful, suddenly the people working for me had families themselves. And so you don't drink with them, you don't hang out nights and weekends. And then suddenly everything around you, you're paying a lot of money and there's like this power imbalance. And then suddenly I remember waking up feeling totally isolated.
Well, really quick, that is not unique to tech or you being a billionaire. It's just insanely isolating.
Anyone working at the top of their field, I would say.
Yeah, as you become the boss of everyone, immediately it's isolating. You're not on the team, you're the enemy.
No one told me, when I started on this journey, how lonely and isolating it would be. And that's okay. I mean, it was for me to learn, I guess.
And a lot of it's our own doing.
I had done that. I had so isolated myself, totally focused on working, continually feeling like I'm not enough, we're not enough, we need to be better. And I had this guilt whenever I would make time with friends and family. And the guilt was I wasn't working on the company and that was how I would see. connection was through the business.
And then, of course, the pandemic hits by myself 24, seven. We were preparing to go public and I always felt like we had made it. We're working on an IPO. All of a sudden we lose like 80% of our business in eight weeks. And then everyone's saying, is this the end of Airbnb?
Like there was a newspaper article, like can Brian Chesky save? for me? These are like actual articles. And I basically just hold up working probably 16, 18 hours a day physically by myself on Zooms. all day.
The team rises to the occasion. And not only we save the company, we go public. And there's no like bell ringing. It's all on Zoom.
Oh, no kidding.
The entire IPO and every single thing, all my memories are on a screen. By the way, I had this like weird side thought. I've never had a dream where I had a screen in a dream. I've never been on my phone in a dream. Oh my God, true.
Not me, every dream. I can't get my phone to work and I need to do it to save somebody or get out of somewhere or find my way out, and it will not work.
That's really unique, because a lot of people have described they don't have screen memories in their dreams. And yet we spend so much time on screens. And I think one of the things the screens do is they can press time, right? Because we tend to remember things spatially.
You have five major inputs and only one of them is being serviced. Your memories are made of the smells, the texture, what you were feeling on your skin, what the atmosphere was, what you were hearing. And this is just two of those.
Yeah, and they're like not even fully dimensional. We go from 30 billion to our company, down to 18 billion to then 100 billion. And one of the saddest periods of my life was after we went public and I'm the CEO of a $100 billion company.
Because you're where you were supposed to be when everything got fixed.
I mean, the bottom of the mountain, you have hope. You still believe in the story, and as long as I get to the top. Yes. But the problem is, when you get to the top of the mountain, oftentimes you're at the top by yourself. Of course.
You're disconnected. It was never the money, the status, the success that was gonna fill it. And of course, this stuff can provide a lot of benefits.
You're not asking anyone to feel bad for you.
No one should feel bad. And I do think people should achieve their dreams. Don't go into it knowing that just success is gonna fill some hole in you, because it's a very, very long lesson. So I'm like really isolated at this point. I don't know what to do.
And a couple characters enter my life. One of them was President Obama. I had met him at the very end of his second term as president.
After making the cereal?
Yeah, exactly. To fund the company, originally we were Airbed and Breakfast. The Airbeds weren't selling, so we decided to sell collectible breakfast cereal. We sold it for the Democratic National Conventions. So we sold Obama-themed breakfast cereal called Obama-Os, like Cheerios.
We called it the Breakfast of Change. And Cap'n McCain's, which was basically Cap'n Crunch, we called it a Maverick in every bite. And so I like to say we were cereal entrepreneurs. And I remember meeting President Obama.
Talk about a guy who probably experiences deeper than anyone can. Like President of the United States, especially if you're black, should heal everything. How could you not believe it's gonna heal everything?
And a revered one. A revered president, one that people love.
And so I met him because I was part of this global entrepreneur summit, kind of this honorary ambassadorship. You get to have your photo of the president. I remember the first time I met him, I said, hey, Mr. President, I am Brian Chesky of Airbnb. He goes, I know, you're stealing all my people.
And basically we were hiring all these people for our communications team because we had a lot of regulatory challenges. And the White House is not a big place. It's like 100 people or something. And so he kind of knew of us, but he was playful about it. Then, of course, they lift the embargo in Cuba and he goes to Cuba and he decides to bring all these business leaders into Cuba, except only one American business seemed to have any substantial business in Cuba, and that was us.
And the reason why was because in the late 80s, the fall of the Soviet Union, ironically, Fidel Castro said, we have to turn to entrepreneurship and be self-reliant because we don't have the subsidies of the Soviet Union. And so they basically turned homes into hotels. They call them casas particulares. They turned homes into restaurants. They call them paladars.
Those are the best restaurants in Cuba.
Exactly, and Cuba, ironically, has a culture of entrepreneurship, even though it's communist. And so I ended up getting to know President Obama. He leaves office. I ended up developing a really close relationship with him. And at one point, we ended up having a standing conversation every week where he would give me kind of assignments.
A lot of it was about leadership and trying to be intentional and thoughtful. as a leader. He becomes like this bit of a mentor to me. It's also surreal. I'm almost like, why is he spending so much time with me?
I still can't figure that out. But I remember getting to early 2021 and I write him a letter. I guess I describe myself as basically everything I just said. I asked him this question. I said, how did you not lose your shit as president?
How do you stay grounded? And he said, you're connected to your roots, and your roots are the relationships in your past. And he described this idea that you should have, you know, he picked an arbitrary number, like 15 friends, and you should be really close to them. And I started thinking, do I have 15 friends? And of course I thought I had all these friends.
And then I thought to myself, well, if I pinged any of them, would it be random that I just pinged them? And I realized it would be. And I couldn't just call a bunch of people, because I had been so isolated. And I had done it by not paying attention to friendships and relationships. So then I decided to reconnect with my college friends that I was living in LA with.
I reconnected my high school friends and I started spending time with them, taking trips. And it totally changed everything about my life. The irony of all of it was these were all the friends I had before I started Airbnb.
I'm sure the most fun you've had through this whole process was weekend one with the fucking air mattresses.
Exactly. And then I meet another person who also changed my perspective on this stuff. His name was Vivek Murthy.
Oh yeah, we know Vivek. We know Vivek, we've had him on.
Oh, you've had him on. He's so, so kind. I hired him as a consultant in 2020 because the pandemic had occurred and everyone was freaked out to stay in Airbnbs, because they're like, if I'm in an Airbnb, is this like a disease that lives on a surface? Will I get it? So we hired him to create this, what we called cleaning protocol.
And I remember having a conversation with him, and I'm gonna paraphrase the conversation. He said, do you know what the number one killer in America is? And I'm like, I don't know, is it heart disease? Is it cancer? He said, no, the number one killer in America is loneliness.
When I was first Surgeon General, he was Surgeon General under President Obama. He said, I was trying to pick like a signature issue and I think he was looking at like opioids and obesity. I think he was looking at a number of issues. He started noticing that there was this dark thread that was running through all these ailments, and that thread was loneliness. And he started describing that about half of Americans identify as lonely and that if you're chronically lonely, it is pernicious to your health.
He said it's worse than smoking a pack of cigarettes a day.
It's worse than smoking 15 cigarettes a day and it takes equivalent of 15 years off your life. I think it's because, if you look at our evolutionary history, humans were about 200,000 years old, modern homo sapiens, pre-civilization were hunter gatherers and we lived in a community. We lived in tribes of what, 50 to 150 people, probably why we can maintain about that many relationships. And we didn't have like DoorDash and Blue Cross, Blue Shield or Kaiser Permanente, and like an ambulance and a fire department. We only had the village, we had the tribe.
And so being isolated was a death sentence.
We've become so individualistic. We've become so self-sufficient and independent, but it's actually the depending on one another that is like the fabric of your life source.
We get energy in life from love, and that love, it has to come from within and from others. And I think that if you're isolated, it's very typical that you might push people away. And so I started learning about loneliness. You know, loneliness has been rising, I think, since the 1950s, but it had an inflection point about 10 to 15 years ago. And I started wondering why are people so sad?
Why are they so anxious? Why are half of teenagers having feelings of sadness and hopelessness? Why are one, in 14 years, having suicidal ideations? Why are men having a loneliness recession? The average American today spends 10 fewer hours a week with friends than 10 years ago.
Then you go deeper. A lot of things are digitized. The mall is now Amazon. The theater is now Netflix. The grocery store is now Instacart.
The office is now Zoom. And each one of these things is a step forward for humanity. But the aggregate means that a lot of us are spending time alone. Fewer people are in families. Fewer people go to the bowling alley or church.
Fewer people getting married.
Fewer people having kids. And I wanna be clear, I'm happy to be alive today, but I think we have to be careful. Technology likes efficiency, and human connection is often inefficient. No one tries to take human connection out of society, but as society grows and evolves so quickly, it's very easy for us to wake up one day and be isolated. And I think that social media used to be called social networking 20 years ago.
And most people don't realize this. language change, but it used to be. you had friends and then eventually your friends became followers and your friends became followers. There was less intimacy and there was less intimacy. Then you started performing, and the problem is your Instagram followers aren't coming to your funeral.
No one changed someone else's mind in the YouTube comments section.
They'll never help you move a couch in your apartment.
Yeah, and so none of these things are wrong. They're just ingredients. And as long as we balance these ingredients with physical community and physical relationships, then we're gonna be okay. But if we don't, and we are completely isolated, living digital lives, then we are gonna recreate the movie WALL-E. Do you remember the Pixar movie WALL-E?
We're on these self-driving pods, looking at screens, looking at everything, but seeing nothing and being totally disconnected from our own bodies. This is something that I've been thinking a lot about. And I'm not saying that we, Airbnb, are gonna solve this problem, but a question you have when you're in my position is what do you do with the rest of your life?
Yeah, yeah.
And I have a few choices. I could stop doing Airbnb and do something else. I could build a mega yacht. Yeah, yeah, yeah.
Be with some oligarchs.
I don't wanna do that. I could go on a philanthropy, but I like to make things rather than fun things. Of course, I'll do that. I could go to space. I don't really like heights.
Yeah, yeah, yeah. So space is not really a good opportunity for me. Given what's happening in the world, I wanna point Airbnb's product and community around, trying to make the world feel smaller and to bring people together. And so that's kind of what I wanna dedicate the next handful of years.
This might shock people. So your own house is on Airbnb.
I've had five people stay with me.
It sounds like a publicity stunt.
It started as a publicity stunt. I can tell you-.
It sounded like go nads. Yeah, go nads.
But now, five guests later, it's actually now becoming a part of my life. And maybe it started a little bit as a stunt, but I was reminded of why I started the company. They come as strangers and they leave as friends. I and my dog, Sophie Supernova, a two-year-old golden retriever, we're the host. People come.
The first night, I make them dinner. I make them my famous Chesky's chips, which are a chocolate chip recipe that's been in the family for many years after I got it off Google.
Many, many years.
Yeah, many, many years. We just talk late into the evening. I then take them on a tour of the office. It's added so much richness to my life.
Here's my only fear of that scenario. Have they not come as fans? That's not the healthiest dynamic for friendship.
Some of them come as fans. It's a good question.
Starts as a fan, but ends, they see you're human. They hear you taking a shit in the morning, they're like, oh God.
Exactly.
This guy shits.
Whatever, whatever.
It's hard to stay someone's fan when that happens.
You live with somebody, you're not just a fan much longer.
The veneer cracks quickly.
Honestly, maybe they kind of come because they have some big ambitions and if you leave with something fairly genuine at the end, it can be pretty special. But yeah, I've had a bunch of people stay with me. I also lived on Airbnb last year. I stayed in like 15 homes, hopping like city to city, and that was pretty amazing. It's been an incredible journey.
What's happening with you, romantically?
Not a lot.
Are you putting effort into it? Do you care?
I do care.
Because I'm going to argue, you know, the big thing that Obama left off this list of how he navigated the White House experience is he had these two girls that ultimately didn't give a fuck. he was president.
That's a really good point.
And he had a wife that didn't give a fuck. he was the president. You need some people in your life that don't give a fuck about what you do. I just got back from 15 days with an eight year old and a 10 year old. Like.
there ain't no break from that and there's no buying your way out of any of it.
I think that things in my life have happened in a different order than I expected. When I was in college, I probably thought by the age of 41, I'd have a family and maybe wouldn't be as far in my career. And of course I went on this complete rocket ship. A lot of what I've maybe been trying to do professionally is design the world that I wish to live in. And I think what I kind of been seeking my whole life in some way is seeking connection, seeking love, seeking to be a part of something and to be a part of other people and having them in my life.
I'm quite certain you would advise a young entrepreneur that having a great idea doesn't mean anything. No one's gonna knock at your door and go, excuse me, sir, do you have a brilliant idea I can realize for you? You're not ever gonna be sitting at home and someone's gonna knock on your door and go, Brian, I think I'm in love with you.
Oh, that's a really good point.
It's the exact same thing as being an entrepreneur. No one's gonna do that for you. No one's gonna show up magically.
You have to be out there. You have to put in the effort.
I don't mean to shame you about being single, by the way.
Yeah, because I definitely don't want us to end and it sound like that's the only way to have meaningful relationships or ones that don't involve fandom, because often that does still happen in relationships. So it's not like without that.
Yeah, I know people who have married a fan. I don't advise that, sure. Well, you'll see these rich guys around LA with a gal that's 25 years younger than them and 16 deviations more attractive. I think, you know- It also happens- That's not the greatest.
Yeah, it can happen even in regular dynamics. It's something to monitor in general. Yeah. And I think what President Obama was saying to you about the 15 friends is that it's buying the original people, who don't care if you're a billionaire.
I'm agreeing with that. I'm throwing one other thing that helps, which is, as you've already discovered, service leads to this self-love and this self-esteem. That's what the results of service is, right? And I will just say, if you've already discovered that, there is no greater act of service than having a fucking deal with these kids for 18 years. It's endless service.
So I'm only saying the apex of service is having these dependents.
I totally agree.
It is, but it's service, but they're connected to you. Your ego is, I don't wanna say, completely removed from your children.
It's not at all. But just the very act of doing many, many things all day long that you would otherwise choose not to has a very positive impact on the people that I know. As long as they're doing the work. Now there are a lot of people that have kids that don't do a fucking thing, and I don't think they get the rewards out of it either.
I totally agree. I mean, I think this is part of the next chapter of my life.
Is figuring out how to take your expertise and apply it to this issue of loneliness.
Well, that and personally not being alone and eventually having a family. That is absolutely something that I would like to do. Need a co-founder.
Yeah. Well, it sounds like you've kind of had a right sizing of your goals.
Yeah.
You reached the one. I think you're the second richest person we've talked to,
which is insane. Really?
He's got $12 billion.
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