Let's just say this isn't your typical Airbnb.
Hello.
I'm Emily Chang, and this is the circuit. When Brian Chesky said he was going to start renting his own home on Airbnb, I gotta be honest, I didn't quite believe it. Turns out he meant it, at least for now. This is the first time me or any journalist set foot in Cheskey's.
Home, and I had some questions.
Just what can a guest expect from a stay with the CEO of Airbnb Warriors game check? These are ten of stark cookies?
Really ten Stark cookies.
I was skeptical.
I know, chocolate chip cookies.
Check. But we also go deep on his journey from young art student to multi billion dollar entrepreneur to hoping for a family of his own, the exhilarating highs of it all, and the lonely lows. He says Airbnb's darkest moment may well be what saved it and him. Here's my conversation with Airbnb CEO Brian Cheskey, with a few cameos from Sophie, his favorite golden retriever. What's it been like playing host so far?
Oh my god, it's been it's been a lot of fun. I'm a co host. I got Sophie Supermo, she's a nearly two year old Golden Retriever, and it's been cool because I haven't really hosted that much since the early days. I was one of the first two hosts in two thousand and seven, and for the last maybe five years, I hadn't hosted. And last year I started living in Airbnb because I wanted to show people you can live
and work anywhere. And so the first six months of the year, I'm living on Airbnb, I'm traveling, I'm staying home to home. And I had a goal in my mind. I said before the end of the year, I want to be a host. And I only have this house.
This is like your primary house, it isn't your extra house.
I don't have a second house. And so if I had a second house, my instinct would have been to rent that one and not this one. But I had no other house, and I thought a little initially, oh this is a little crazy, like you, a little crazy. I'm a stranger in my house. And then I realized, wait a second, that's what like millions of people have to go through. And I put myself back in the shoes of my old self or a host, and I had to go through the journey of what's it going
to be like to let someone in my house? And what am I gonna what I'm going to ask them? How are going to my screen guest? And I started really looking at our verification program and our reservation screening and like is this really And I felt really good about it, And so then I started hosting.
Well thanks for having us our best behavior. But you know you're kind of busy. You're running a multi billion dollar company. Like what made you want to make time for this?
I think two things. I think number one again, I never wanted to be one of those CEOs that's kind of an ivory tower, just looking at data and spreadsheets all day. You know, when you build a product, When you first build a company, you make something, usually for yourself, you don't have any users, you talk to them, you're looking the product every day, and the one day you
wake up and you're running a giant corporation. If this happens, if you're so lucky, and the company becomes a series of numbers, And I think it's really important for business leaders to never reduce their customers to a number. You don't want to get emotionally detached. People aren't just numbers. They're people, and they make decisions, and they have to love your service. And if they love your service, they're
gonna tell other people about it. And that means that you need to be emotionally connected to what you're doing. I understand when hosts are complaining about something, or your customers complaining, what do they mean? Do you have a deep intuitive understanding what they're talking about. So that's that was like the main reason I did it. But then there was another reason I wasn't expecting, which is as fun is it really?
I mean, it's fun to you. You're giving people the full court press, like I feel, you're staying a couple of days, taking them out in the city.
And I'll be honest, I wouldn't intuitively have thought it would be fun. I didn't like grow up wanting to be a host. It was one weekend I I, you know, and so I kind of discovered hosting, and I guess this whole experience reminded me of how much fun it was. And if I wasn't the coo or bingb I would still host. That's how much. I've decided it's really fun. It's like, you have this nice house, don't you want to share it with people?
But these are strangers, right, These are people you don't know.
They arrive as strangers, and I'm really proud that they do usually leave as friends. I'm actually one of the guests I'm taking to a warrior's game because he's actually local. But wow, yeah, so I try to stay in touch with my guests.
Okay, it was crazy to think you were going to rent your house to a stranger, or that you were going to stay in some stranger's house, and now it's just what we do. Does the level of human openness to that idea still surprise you?
A lot of people ask me, like, what did you know that no one else knew in the early days, Like Paul Graham, er first investor, said, a founder usually has to have some insight that no one else has. Otherwise, why are you doing this? What do you know that no one else knows? Because if it's nothing, then someone would have already done this. And what I like to tell people is I think I'm less a visionary than expeditionary, in the sense that I didn't have a vision I
discovered something one week and I couldn't pay rent. I decided to let people in my house only to make money. For the most part, I thought it'd be fun, and I end up becoming friends these people, and it made me realize that like these homes are these private spaces that you'd never let anyone in. And if you were like an alien looking down on Earth and you realize all these there's all these houses that people live in, but then all these other people travel, but they don't
stand those things. They stay in these other spaces in these one district and they all stay together. You kind of look at that model and say, it seems a little inefficient, but you understand why there's no trust. And we thought, well, if we could solve a system of trust and make them not feel like strangers, this would be an idea to spread on the world. But you're right,
it's like so counterintuitive. It's so funny. I like to joke that people could imagine living on Mars easier than they can laugh and match I something's laying a stranger in their home. You just really think about it. I think we have trouble imagining sociological changes, sometimes harder than technological changes. We can all imagine things getting bigger, faster, kind of moving to more like to other locations, but it's hard to imagine changing behavior.
But Airbnb has actually been a big part of like maybe a major sociological change probably.
I mean, it's been now been used one point four billion times. And if you had told me when we first started that one point four billion people from two hundred and twenty countries and reagions will live together, that on a typical night we'd have nearly the population of Los Angeles staying together, people from the Middle East and Texas like cultures you wouldn't necessarily think mixing together coming together. I think we all would have said you were crazy.
Like I remember somebody I remember in the early days used to tell people this idea is going to be huge one day, thousands of people will do it, And I think that sums up what we thought. But I think that, like maybe Emily, the lesson is, you know, I think we're conditioned to think people aren't good. Yeah,
and some people aren't maybe at some basic level. But I guess I just maybe I was, maybe I was too naive to know the difference because I kind of it just was optimistic and I thought most people are fundamently good. We're probably actually ninety nine percent the same. And I know that can sound naive, but I actually think we probably have more data than almost any experiment in human history. There's never been an experiment where more
people have lived together. And yes, occasionally things happen that aren't unexpected, but that's not the parts that surprising me. This surprize of me is how similar people are. And I think that was one of the core insights that
we had. And it's like most tech comans have to understand laws of physics, we call these first principles, and we also have to know a different law, which is a law of human nature, like who are we at a very basic level, And if you can start to understand that, then you can start to design for people.
Well, I'm excited to learn a little bit more about who you are. We've talked so many times over the years about the business about new products, Miles Jones, and hopefully there'll be many more years for that. But what's a day in the life of Brian Cheskey outside the office?
Like what do you you do?
Aside from Airbnb?
There's like a few things I really like to do. I like to I try to exercise. When I first started air meanbi, I didn't really exercise a lot, and I noticed the markercise manage. I have Sophie and I like to go on adventures together. Last year I went to like eighteen different cities. I stayed in a franklaid right house in annab, Michigan. For example, lifelong desire I've had. I like drawing. I think I have some sketch books around the house. I could we could show my art later.
I guess the other thing is I like connecting with friends, so I like I like to learn, I like the draw I like to hang out with people I care about, and I like to travel. I guess those are the things I do.
You know, obviously the pandemic hit. Travel comes to a screeching hall. You're the majority of your revenue almost vanishes. Also, nobody wants to see other people right in that moment? Did it feel like you were standing on the edge of a cliff?
I remember asking my mom a question, she reminds me. I said to her at some point during the bath of pandemic, I said, do you think people ever want to travel again? I mean of course I thought they would, but I had no idea how long would take. I mean, I thought we had made it before the pandemic. You know, we had a business that was doing like, let's call it, thirty five billion dollars in sales. That's about similar. That's more than Starbucks. That's almost like the size of Nike.
If you told me in like the nineteen eighties growing up, we'd have a business that baby, like, you're totally crazy. I thought we're making work in IPO and then within a decade that happens to then lose eighty percent of it in eight weeks, and then you know, I mean you remember there were articles like is this the end of Airbnb? Will erbmbe exist? And I got to tell you, like that changed my life, and it changed my life
and the company for the better. You ever hear people say that they had a near death experience and they had this moment of clarity. Well, thankful, I've never had that, But I felt like I got that clarity from a business perspective.
How did you change as a person.
I like to joke that I'm forty one going on sixty one, because is that a good thing? We'll see my hair is a little greater, but I think I think it is a good thing. In this case, I think I really grew up there in the pandemic. I
really grew up. And the reason I grew up is because I think I felt my responsibility more like we all probably walk around every day with responsibility, but like you know, you don't feel your responsibility to feel the edges of it, like to you feel people depending on you. And in one moment, I had every stakeholder like depending on me. Employees are worried about their jobs. Investors were
they about their investment. Guests were worried about they can get their money back when they're traveling, you know, Hosts are worrying about like if they're going to ever be able to keep their home. And then communities worrying about how are we going to house all these nurses and firefighters and doctors. And they were all reaching out to me at the same time, and not in a low key
composed way, you know. It was like there was a lot of fear, a lot of concern, and I think in that moment it was like a total growing up experience, and it was almost like a bell rung in my mind. Head. And I remember my board member Ken Channel, who was a CEO of AMX. He was CEO during nine to eleven in the financial crisis to his night, so he's certainly been through crisis. And he basically said, I've been through two of the biggest crisis in my lifetime, and
this is ten times bigger than either of them. He said, this is your defining moment as a CEO, and I said, well, I'm going to be defined by this crisis, and it's going to be on our terms. I think before the pandemic was a little bit the nice guy that could be a little conflict of hers and that makes me want to appease people and like not want to make hard decisions.
Said yes to too many I said yes.
To too many things, and it was on me. You know, the CEO has to say no. Steve Jobs, you say, focusing is not about saying yes, it's about saying no. Well, I had to learn to say no to a lot of things, and some of them were pretty heartbreaking. But you have to make hard decisions. And that's I think what ended up happening is I just think I saw clarity. We made a lot of hard decisions. I grew up by feeling my responsibility. I got more disciplined, We got
more disciplined. And I think I had lessons that have now been sewed in my brain and I'm never going to forget them. You know, you don't go through something like that without it permanently changing you.
What are the lessons?
So the first thing I learned is who people really are. The good news is that the vast majority of people turned out to be great people, still good, still good. You can also learn a lot about yourself in a crisis, and I learned that the hardest thing to manage the crisis is your own psychology. And I learned how to manage my own psychology. I learned how to be focused like never before. I also learned how to run a
company totally differently. Because when you like never seen money before in your life, and like, one hundred thousand dollars is more my I ever see in my life.
We raised billions of dollars, and you personally made billions of dollars.
Yes, and we raised billions of dollars, and we have it in the bank account. And so it's easy to say yes to things. I learned to say no. I learned to be focused. I learn to focus the entire company and point them, every single person, to one direction. And I learned to stop apologizing about how I wan
run the company. I didn't realize until after the crisis that I spent five to ten years apologizing every step of the way or negotiating how I run into the company, because you hire people and they come from Google, Apple, Microsoft, Amazon, and they bring their way with them. And what I realized I was doing was trying to find some midpoint between how I wanted to run the company and how they wanted to run the company, which actually made everyone miserable.
I had to go into wartime mode. And the crazy thing was is as I took more command, more control, became more decisive, more bossy, so to speak. I think people were happier because they had quarity in direction. I think those are some of the lessons I leaned.
And then the tide turned, or maybe it's like the Titanic didn't hit the iceberg totally. You know, you go public, airbnbgost public. The end of twenty twenty, I'm interviewing you live.
That was television most memorable And Who've ever done your shares.
Double before the market even opens.
Yes, and.
You can't even speak like you're completely tongue tied. I actually want you to. I want you to watch it. Every time I watch it, I like, Yeah, it's such a moment when your opening price shares indicated to open right now at one hundred and thirty nine dollars a share, which is more than double what you priced that. I mean, are you at all concerned about froth? What do you think about that number and the potential that you're leaving billions of dollars on the table.
That's the first time I've heard that number. That is, that's a.
You know, when we in April we raised money and it was a debt financing, that price would have priced us around thirty bucks. So I don't know what else to say. It's that, that's a a that's a very that's that is I'm very humbled.
Wow.
And you know, we know that we're on a very long journey and we're going to be very very focused. Is obviously to is a very special day for everyone. But you know, the highest stock price, the higher expectations, the harder we're going to be working.
Obviously, Wow, I watched that in a long time. Wow, that actually makes me a little emotional.
What's going through your head in that moment.
I think that moment it was like my hard drive crash, and I think it's that like the pandemic happens March fifteenth, id's of March. We have a emergency board meeting. All of a sudden, I realized, like this is going to be a twenty four hour thing. And every day I would wake up, put on sweatpants, like go right to the computer. I would like shower at night. My schedule
is so crazy. I would leave my house and I probably work sixteen hours a day, seven days a week, and I'd probably never stop at any point to think about anything. It was just one day after day, and that moment I had to think about everything. The whole year was like you took a whole year and you made it like a fifteen second trailer and I was like, oh my god, and it just maybe at that moment it all hit me. This is just so crazy.
The interview went viral.
It did people could see it hit you. Yeah, yeah, yeah. My eyebrows went to the top of my head and I didn't know they went to high. That was but yeah, that was that was one of the most surprising moments in my life. I'm not usually speechless.
Yes, you're normally quite eloquent.
I did not know what to say. I guess I'm also thinking back now, I feel so lucky because I did not manage the crisis on my own, and I kind of felt like I had the wind in my back, as if like people were working with me and helping me, people I knew, and I kind of felt like I had a lot of benefit of the doubt that like maybe people were rooting for us, and maybe they weren't. Maybe they weren't, but it felt like people could have made it a lot harder if they wanted to, and
they didn't. Employees, like very few employees resigned after and then they could have, like they could have gone to work at Google or like who wants to work at a travel coming pandemic? You know, the board stuck by me. My founders gave me so much support. Hosts kept listing. They adn't take their listings down. I remember in the depths of my darkness, you know people who are writing
articles what air can be exists? I would get text me as former employees, I want airb me to still exist, and I remember asking like, well, why, like why other than having emotional attachment, like why do you want it to exist? I think the best answer I heard was because if you don't do what you're doing, no one else will. Like there's many sites that you know, you can get a house or you can travel on vacation,
but there was something a little different by Airbnb. There's not a lot of designers running companies that have this created spirit. There's this idea of like real the roots of airbb around connection to people living together that doesn't really exist anymore on any other platforms. So that was like pretty moving to me. And I mean twenty twenty was an intense and emotional year and that was the capstone.
Do you ever think about what would where Airbnb would be if the pandemic didn't happen.
Yeah, it's almost scary to think about. We wouldn't be here today. That's the crazy thing. Like your culture is often forged in your darkest moments. I think people think of culture as like, you know, the perks, the yoga, like the yoga, free food snacks, kombucha. No culture or the shared behaviors that you all have based on lessons you've learned together, and the lessons you remember most are during the moments of trials and tribulations of things that
forge you. We basically made like five years of progress in like six months, and I think we would have never reached the potential that we can now reach because the whole trajectory of the company change. There's really before the pandemic and after the pandemic. There's me before the pandemic and after the pandemic. Would have taken me a decade to get to this point without the pandemic, you know. I think that you have to rise to an occasion,
and you can't ask for an occasion like that. You can only hope that if it happens, you will rise, and you can't know until happens.
We've seen a lot of founder CEOs step back, whether it's Amazon, Google, Twitter, Pinterest, Slack. Yeah you're still here.
I think when I was starting out, I think it was afraid to run a giant company because it didn't seem fun. It didn't seem how many people go to work at a giant company. So I love working at this giant company. There's the thing that's most surprised me is I have more excitement today than I did when I was in y Combinator. The job today as a public company CEO is more fun really than the job as a private company ce you.
I feel like I often hear the opposite.
You often do, And there's maybe all sorts of lessons because you know, by the time you run a public company, you're negotiating everyone. You're trying to pee shareholders, you're trying to pease employees, You're negotiating. And I learned that if you can just listen to yourself and be true to you and not apology to who you want to be, the actually you might make everyone happier. Anyway, Like we stopped, I stopped obsessing over making money, and we end up
generating three half billion offree cash flow. There's a paradox there, and so I have more fun than I ever had. But I also think there's two other possible explanations. Only I think we're very long term oriented, and that means we tend to be relationship oriented. I'll give you one
data point. We did, like every financing round we did when we were raising money, we never took the highest price, and that's unusual because we always tried to get the most value out an investor, and a lot of people say that, but we try to do I don't try to win a negotiation because I'm like, listen, this is our first negotiation, but we might do another deal in ten years. So I want to think of have a
real relationship with you. And I think the other thing is you got to be like it's all about how fast you learn. I like teil entrepreneur. I think of the growth of your company. You have to grow faster than that. And if you don't grow faster in your company, then your company is going to be pulling you, and then you're going to eventually be holding it back as you have to basically be this beginner, constantly learning, constantly
absorbing every single thing. None of us. There's no manual to have be an entrepreneur, and the problem is if you were to write one, it would be outdated in the moments printed because the rules keep changing.
I think about Steve Jobs coming back to Apple, bringing it out of a death spiral, and I'm sure everyone would agree it mattered that he was there. Yeah, But does it ever feel like this immense responsibility that you have to stay or does it feel like a burden.
If I wasn't enjoying it, that probably would. But if people told me you have to stay, I would It wouldn't affect me. Not, it wouldn't affect me at all. I only want to keep doing this if I'm the best person to do this, and the interest to me is longer I do it, the more, I'd probably become the best person because I have both the history of the founder, being a founder that you can never replace.
And my biggest weakness was probably I was young and I didn't have a lot of experience, But now I have that too, So so long as I'm still the best person, I want to keep doing it. I think that our days just getting started. So Phase one product market, Phase two hyper growth. Phase three, become a public company and like generate profit and be a real company. Phase four reinvent yourself.
M do you ever get jealous, like looking at your co your peers who have left their companies and they're moving on with the next phase of their life.
Not even close. No, no, no, I don't love vacation all the time. I am a vacation company. I mean, I mean, I love traveling in the airbnb, but I don't. I like to live vicariously through my friends who like kind of leave the company. I like hearing what they do and pretend that I'm like them, but I also know that, like, I don't think I would be good at doing that. Somebody asking me, like, why are you
doing Analystic? You don't need to make more money, And I said, well, you wouldn't ask a painter or why are they still paying. You wouldn't ask a musician why they still make music. You wouldn't ask an athlete why they still play the sport. And I like to think of myself more as like an artist or designer. I mean, I know extensively I'm an entrepreneur and a business person, but I think of myself as kind of designing and making.
And the reason I like have more fun now is because now it's more creative than you used to be. There's a period where you start a company, it's creative, you're making stuff. Then you get successful, and the problem with being successful is now everything is breaking. You have all these responsibilities and you're just you're reacting all the time. And some people said it's like jumping off a cliff, assembling the airplane the way down and you're like an
emergency room triage doctor. And we're kind of past that point. We still have our challenges, but now we can have ideas. We have this giant community. It's been used a billion a half times. We handle one hundred, like over one hundred billion dollars to the platform both directions. We have like over one hundred million verified identities. We have a brand that's a nown verurban pop culture. We have one
of the most talented teams in the world. If I'm not having fun and if I can't imagine something new to do, then my god, how else am I going to find meaning in life? That's awesome?
Are you an artist designer first and CEO second? Is that what you would say?
Probably? Probably? I would like to be remembered as a designer first and an entrepreneur CEO second. And the reason why is I mean I'd like to either read a fine what a CEO could be as a person that came from a creative field, as a designer, or maybe more importantly redesigned what a designer could be. That a designer could design not just a thing, they could design a company. And I don't know it. I think you're
always what you were growing up. You know, there's something about what you were growing up that's always in your heart. And probably I approach problems more like a designer than a CEO, although I probably said.
The interest and how does that change the company? How is that mentality infused into the company? I mean, I get the sense you're very involved in the details.
Extremely is that a code or a bad thing? If you ask me or my employees, it depends. I have like books like this. Frankly i'd write book here right my favorite architect or Charles and ray Eames to the great industrial designers of twentieth century, Charles Emes said the details aren't the details, they make the product. And I am absolutely involved in the details. I think design is
not just how something looks, how fundamentally works. I think design, you know, is really about, like understand It's about simplifying something. And people think simplifying is removing things, and it's not. Simplifying is understanding something so deeply that you can get to the essence of something. And to understand something deeply you have to be very multip listenary. You have to have a very holistic view of everything. And so I think what we do is to make the content complex simple.
We think in terms of systems. I mean, the definition of design is really typically you would say it's a better way to assemble something to achieve a task, and some assembling people systems to achieve a task more efficiently. And I love almost like the Jigsaw puzzle, even like how we became profitable. I like, we kind of designed the p and L. You know, most people cut, We didn't cut. We designed. And you can never save as much money by cutting as by designing, because cutting you're
just like lopping things up. But designing says, well, instead of cutting all these expenses, what if we just thought about the whole operation differently, to have fewer parts, fewer components. And it really takes creativity to do that. And that's just one example. So I think of myself as a designer that way.
I mean, over the years, you've really emphasized the values of Airbnb, weather it's community or connectedness. What does it take to make something that people really love?
Oh, that's such a good question. When I joined y Combinator, the first day, they give you a T shirt. It's a great T shirt and it says make something people want. And if you get an exit, they send you a black T shirt and it says I made something people want. And that was something that always stuck with me, that
I just need to make something people want. And I think the way you make something that people want is first you have to care about people, and you have to understand people, and so I like to put myself in the shoes of the person. We did this thing ten years ago. I named a snow White after the movie snow White. Snow White was basically the of the storyboard and basically is a feature like animated film. Walt's one of my heroes. He basically this film was so long.
He had a storyboard, and I said, why don't work business to do that? Why don't businesses understand who their customer is, storyboard the experience, and then try to put themselves in the shoes of that person and imagine what are they going through? At what moments do they need be surprised and delighted? At what moment do they be reassured? And just every single opportunity is a detail that you could perfect. By the way those ads, you wouldn't believe
how many reviews I'm in with those. I review every song, every ad every photo, like we do reviews every single week. We look at like dozens and dozens of ideas and concepts to get the exact right idea.
Talk about being in the details, I mean, is your team like, should we invite Brian or not?
If they had the choice that you're presuming they have a choice. I like to say, only I can cancel the reviews just in case. Well, let's be cleeer. I don't intend to be in the details of everything forever, but you have to teach. It's like I'm a coach and I'm like trying to teach a level of detail and excellence. And I think people model themselves after the leaders. I think there's this idea that I think is a bit of a myth that great leaders hire great people
and empower them to do great work. And that sounds great, but they're missing something. And what they're missing is you've got to be in the details of the people. It's not micromanaging, it's auditing and understanding what they're doing. I have a board. They audit everything I do. They're aware. They're not telling me what to do, but they're aware. So I don't tell people what to do, but I'm aware of everything they do. And I want to lead by example because I want every single employee in the
company to be in the details. That's our culture to be in the details, because that teaches us sense of care craft, expertise that flows through everything. And by the way, I didn't do it this way for ten years.
There's a fine line between micromanaging being in the details in a good way in a bad.
Way, right, yeah, And I think that, like I think at micromanaging is like telling people exactly what to do. I don't tell those people what to do with the ads. I just look at work and I tell them what I'm feeling, what I'm not feeling, I'm brainstorming things, and then they'll come back with a totally different idea. I like to hold people to a really high standard, and so I expect so much of my team, but I like to tell them I never want you to do
something I don't think you can do. So if I'm telling you can do better, what I'm really saying is I believe in you, and I believe you can do more. And I think the role of a leader is to constantly be reaching for some ideal. You're reaching for a vision of a world as it could be. You're reaching for an ideal and then you're hopefully seeing potential people maybe they don't even see in themselves, and if you're a good leader, you will get that potential out of them.
And that is kind of the whole thing.
We've talked about the mostly good things that Airbnb has created. Bad things happen, bad things happen in airbnbs. I'm sure you remember the Bloomberg headline Airbnb is spending millions of dollars to make nightmares go away. How has Airbnb grown from those situations? And what's your sort of what's your sort of fourth star when dealing with the bad thing?
Yes, well, I think our first north star is to do anything we can for somebody if something bad happens. Actually, our first north star is to do everything we can to prevent it. And if something were to happen, I always like to say we should do more than it's expected of us, not what is expected or less than it's expected. And so, you know, I remember the first the indication.
Was like, oh, you're like sliding these things under the rug.
Oh no, we're not trying to slide anything on the rug. We're just trying to go above and beyond. We have a dedicated safety team within customer service, and I've instructed them very carefully that you should always do more than it's expected with you. I mean, we're in the service business. Something horrible happens, you need to go above and beyond
what service? And so we do spend millions of dollars, but we spend millions of dollars because we have an AIRBM guarantee called air Cover that protects you three million dollars against property damage, a million dollars of personal liability. You know, we try to do whatever we can to
go above and beyond. And I think I would always try to imagine, like what would like I expect somebody to do if something we're horrible and I were in that position, And I really try to make sure that that's the culture of the company, that we go above beyond. And so that's what we're focused on.
Tech is going through a tumultuous times. Oh yeah, people are getting laid off, tens of thousands of people getting laid off in waves. How do you think about how Amazon and Meta and other companies are handling these layoffs.
I haven't read all the letters. I like that they're like being pretty transparent. You know, we obviously had to go through a layoff. And I always felt like when I would read some of these corporate communications that like they weren't written from by people. They seem to be like written by committees. And I felt like maybe a bunch of lawyers HR people had stanned the edges off the person to the point where the person speaking wouldn't actually talk like that. And it's maybe the no fault
of anyone, except maybe they're like managing risk. And I took something off a shelf like a playbook. And I always thought I'd rather say the wrong thing, but people think I really said it. Then they say the right thing and you don't even think it was me, and I care. And so the first lesson I had in the pandemic was any communication I write, I don't have people write it for me. I might have someone like a couple of people look at it, but I'm going to write it.
You write your own stuff.
I write everything that comes from my name. I write everything. I don't have people writing drafts. And a lot of CEOs, a lot of CEOs don't write anything that they have their name on I think that's the first problem. We've got to write it yourself. The second thing is, I think when you do like a layoff, if you're going to cut, you need to cut once, and therefore you better cut deep enough try to avoid doing multiple layoffs.
I think multiple layoffs can be very difficult from a cultural standpoint, because if there's more than one, then people can't trust they'll ever they'll ever end, and the company is like in a paralyzed standstill if that happens. I think the next thing is that you should again, in any crisis, you always do more than it's expected. So I would recommend doing more severance than is even intuitive. And whatever a cost you, you're probably gonna win it
back in good will. And the employees staying are going to notice how you treat the ployees leaving, and whatever dollar you spend on a person leaving, you're gonna get more than that dollar back through the effort of the people staying. And that's what I got. And I also think it requires creativity, Like, for example, a couple people on our team, I co founder came and he said, why don't we take our recruiting team and make them like an outplacement to help get other people get jobs.
And someonel said, wait a second, if people are getting laid off, why don't we let them if they want, opt into a directory where other people could reach out to them. So we publish a directory. But no one wants to reach out to people if they think they were the bad people that got fired. So you had to give them dignity. So you have to write in your communication that these are great people. Others are lucky
to have them. And then the final thing is I used a word that no one ever used in the layoff, and the word is love. I said, I really feel love for all of you, and I just wrote what I felt at that moment I wrote it. I felt it. No one would ever written that for me. And I think the key is just whatever you feel, you say, like tak like a real person, not a CEO. And maybe in though.
Way, you started Airbnb at the depths of a financial crisis two thousand and nine, what's your advice to entrepreneurs now?
I think this is a great time to start a company. I think, by the way, if you look at the history of companies like Apple and Microsoft, I think we're starting a down economy. Google emerged during the dot com crisis. You know, we started during the Great Recession. I know Uber started kind of the wake of that, but you have less competition. And if your idea is really good and you can make it in a tough economy, you can definitely make it in a good economy. And I
think that you learn better lessons with constraints. When there's a free flow amount of money. There's just not enough constraints, And I think the discipline of being in a really difficult environment will teach you something. If you want to be an entrepreneur, you should try to. I think start a company to want to run for a long time, not start a company to sell it. If you run accountany for like ten years or twenty years, you're going to be through multiple recessions. So why don't you build
the muscle now. I like to tell people the best time to start a company is the moment you're ready and who cares about the economy. But if it's a bad economy, it's surprisingly easier usually unless you need a ton of capital to get started.
So what do you want the next phase of Airbnb to b? Say five years from now?
I'm in this very unfortunate place where I'm forty one years old and I've achieved more than I ever thought I would at this point in my life, my whole life. The biggest entrepreneur is Bob from Bob's Pizza Shop in my town, and so I didn't know I could do all this. So I think my motivation has changed, like when I was starting, like I think, like a lot of entrepreneurs were ambitious. We want to show the world we're going to make a dent in the world and
we can be successful. And that doesn't motivate me as much because if I haven't proved that by it now, I don't think I ever will, Like no amount of incremental money or status, or like showing my parents or my friends growing up, like it doesn't matter any Like I've already done whatever I'm going to do. And so at some point your motivation has to be something beyond yourself or you're done. And for me, it's two things. Number One, A pianner paints and I like to create
in design and I just love doing it. But I feel like at this point, again, we have this brand that the world knows about. I've been able to recruit some of the best people in the world. We have all this capital available, We've all these capabilities. It would be such a shame not to use that to solve a very important problem. And the problem that I'm most concerned about that I think we can help is that I think this is the loneliest time in human history.
It's probably the longest time in human history. It's so lonely that if people lived this isolated alone thousands of years ago before modern technology would be dead. Right. There's a reason loneliness hurts. It's because some.
People would say, like tech is connecting us all and making us less lonely.
I mean, loneliness has been rise in the United States in the nineteen seventies as far as I can tell, so it's definitely not all tech. But I do think that we need to have a reality check. And the reality check is every new piece of technology feels like an incremental step forward for humanity, but when you take out step back, you take the aggregate experience. We always have to ask ourselves are people happier and are they
better off? And I think life expectancies up. Fewer people today live in poverty, and every before there's so many great things and most of us don't want to live in an era before today, most people wouldn't choose them. At the same time, with all the technology reasons that we have, how good is the world and how good could it be? The average American spends ten more hours alone every week than ten years ago. So every year we spend more out more time alone. We're sleeping less,
exercising less, spending less time with friends and family. We're doing things in the digital world. And I'm not saying phones and digital world is bad. It's just it's like a recipe. We need to marry that with physical community and physical connection. And you know your Instagram followers aren't coming to your funeral. No one changed someone else's mind YouTube comment section. So we need to marry the best of the digital technology with the best of the physical world.
The promise of AI is going to be awesome if we can achieve it. But we should probably stop thinking about technology is a good or bad thing. We should think of technology as power and is It's like fire. Fire can cook food and it can burn something down. Nuclear power can light out a city or destroy a city. So this technology is power. Is power good depends who'se hands it's in. That's probably the simplest way to think
about it. We have all the technology available to us to solve this loneliness problem, to reconnect people, and to solve so many other problems, so long as we can cooperate and just have this real sensitive responsibility. And I think the designer in me, you know, we're trained to like have to just be constantly like thinking about the impact we have. And I'll be honest with you, Like when I started AIRBNBA, I wasn't that mindful of the impact or me would have on the world, on communities.
It just kind of grew and grew and grew. And now I've learned a very important lesson, which is, if you invent something and you put in the hands of one hundred million people, they're going to use it for ways you could never have imagined. And you have to be honest about that. And you have to be willing to adapt, to learn your lessons, to pivot, to navigate. And so I am an optimist. And the reason why is I think I'm optimistic ultimately about our ability to
learn lessons and guide towards good things. Although it can be a very windy road. I do think we eventually get there. I wish we got there a little faster together. I think everyone wishes that. But I am ultimately an optimist and I do think that. But I am concerned about the more technology that seems to be available, the more spent time we spent alone and we Therefore, the answer is not demonizing technology, because then we're putting fingers.
I think the answer is being very honest about what makes it happy and designing things that create those conditions. I went the next chapter, ebe I want to be less about housing, less about travel, and more about connection, more about bringing people together. Now it might still involve travel things, it might still involve housing things, but new things we're going to do are going to be a lot more about bringing people together.
All right, Well, here's to new.
Things, new things. Thank you, Thank you very much.
You've been doing this like fifteen years. Teen years is a long time.
This is a long time.
Does it ever a text standard? Does it ever get like lonely at the top?
Oh? Yeah, how does that feel like? Well, no one ever told me how lonely it would become. And one day I wake up and I have a life people around me, And it was the loneliness ever felt my life. This experience isn't shared. When you're in charge and you're around a lot of people that you pay, there's a power dynamic. Everyone's depending on you, and success that happens really quickly. You can be a little hard to deal with.
What makes us happy is knowing that we can have somebody we don't have, and it's like we're climbing, we're reaching. Then you realize, oh, I got It's not about what's outside me, is this in me. I got to look inside myself. I had this period of time leading probably up to the pandemic and even in the pandemic, where I had to look inside myself like what's going to make me happy? Like why am I doing this? And I also got really isolated a pandemic. I didn't really
talk to people. It was the loneliest ever felt, and I realized, like, this can't be the rest of my life. So I got really focused on like reconnecting with old high school friends, old college friends. And I mean it's so crazy, like coming from me. You can have all the money world, all the success in the world, but a thing that makes most people happy is just connections and relationships.
You talk about your parents and your family a lot. Do you want a family? Like do you want Oh?
Yeah, definitely, definitely. It's I mean, it's probably the one other than it's probably the one thing I haven't done, you know, like I've done a lot professionally. I got a dog that was a starting I wait to let me take care of something really like low key first. If you had told me in my twenties what my life would be like at forty one, I would have told you I have a family. Maybe I wouldn't be that far in my career and things happen in different order.
I now have like a huge public company and I don't have a family, and so it kind of makes sense though, like I did things in different order, and the last fifteen years has been work and all consuming Airbnb.
So is there like a goal for the next decade of Brian Chesky?
And as long as you're in a constant state of becoming and changing and growing, you're going to be okay. And I think for us, like we're in the tech industry, it means we're in the change industry. So we have to change and reinvent ourselves. And that's the one thing we haven't done. We haven't done the next thing yet. I don't want to feel like the best idea we had was in my twenties, my friends. I feel like there's more ahead of us.
You obviously you lived around the world in airbnbs. You've interacted with so many cities and people in different countries, and many of them welcomed Airbnb with open arms, and some are still resisting.
Yep.
Why do you think that is?
So? Every city's a community, and every community has many different stakeholders, and they have many different circumstances. Some cities need more tourism and they reach out to us. Other cities have been going through a housing affordability crisis and they're very very sensitive housing and take off the market. Other cities they really depend on short term stays, but they want them done a certain frequency. And so the lesson I've learned is you got to like, there's no
one size fits all. If the treat every city personally, you have to understand their needs. I mean, it's kind of like what designer would do and try to make a system for them that works.
People think Airbnb is driving up costs, enriching landlords, bringing in floods, of churists changing the character of a place. What do you say that people who are like, I hate what this is doing in my community.
Well, I never want Airbnb to do anything other than strength in a community. I also think it's really important and never presume that we're the good guys. I think we always have to be skeptical about is what we're doing. And so, for example affordable housing, a lot of cities said, you know, we want to have some basic restrictions on how Airbemy CANbus in our city. So we have like
we comply with registration systems for cities. We want to make sure that like cities say they want to be able to we have to collect our fair share taxes. You know, we all been instinct to be defensive. So you're doing something I know I'm not, and you have to ask, well, are we yeah, and how can we evolve it and do it differently? So it's constantly like adapting.
You know the airbnb is exacerbating the housing crisis or the people who think like, oh, this is gentrifying my neighborhood. I can't afford anything, there's not enough places for people to live. What's your response to that?
I started Airbnb and my co founder because we couldn't afford to make rent, and so our roots of air and B is in providing housing that is more affordable. The vast majority of our hosts are renting the home that they live in. But I also want people to know that we want to strengthen communities, and if that means that they need to change the way air and B exists in their city, will have that convers.
Thanks so much for listening to this episode of the Circuit. I'm Emily Chang. You can follow me on Twitter and Instagram at Emily Chang TV. You can watch full episodes of the Circuit at Bloomberg dot com and check out our other Bloomberg podcasts on Apple Podcasts, the iHeartMedia app, or wherever you listen to shows and let us know what you think by leaving us a review. I'm your host and executive producer. Our senior producer is Lauren Ellis,
Our associate producer is Lizzie Phillip. Our editor is Sebastian Escobar. Thanks so much for listening.