At Home With the Billionaire CEO Behind Airbnb | The Circuit

Emily Chang 0:00 [gentle music] [knocking]

Emily Chang 0:05 Let's just say this isn't your typical Airbnb.

Brian Chesky 0:12 Hello.

Emily Chang 0:12 Hello.

Brian Chesky 0:12 How are you doing?

Emily Chang 0:13 Thank you for having us.

Brian Chesky 0:14 All right. Well, we're gonna be hosting. Sophie.

Emily Chang 0:16 Sophie.

Brian Chesky 0:16 Sophie, come. She'll be co-hosting with us today.

Emily Chang 0:19 [laughs] She's such a good host.

Brian Chesky 0:21 Yeah.

Emily Chang 0:21 And this is your house.

Brian Chesky 0:22 This is my house.

Emily Chang 0:26 Love it.

Brian Chesky 0:27 Yeah, here we are.

Emily Chang 0:28 This is the infamous Airbnb of all Airbnbs.

Brian Chesky 0:33 This is. This is where it all happens.

Emily Chang 0:35 I love your coffee table book game. I'm, like, really into coffee table books.

Brian Chesky 0:37 Oh, yeah. It's cool, right?

Emily Chang 0:38 And yours are pretty good.

Brian Chesky 0:39 There's a lot of, like, cool design books here, um, and, like, a lot of memorabilia. Like, there's, uh, Obama O's. This is literally how we funded the company.

Emily Chang 0:47 Right.

Brian Chesky 0:48 We sold collectible breakfast cereal.

Emily Chang 0:50 And you became cereal entrepreneurs-

Brian Chesky 0:51 Yes

Emily Chang 0:51 ... I think I've heard you [laughs]

Brian Chesky 0:53 You'll see that one's autographed by the actual-

Emily Chang 0:55 Oh, wow

Brian Chesky 0:55 ... President Obama.

Emily Chang 0:56 And you handmade these, right?

Brian Chesky 0:57 We handmade these. We designed these with a team, and I literally hot glued this one myself. Joe made me this one.

Emily Chang 1:06 Did he [laughs]

Brian Chesky 1:06 This is my IPO gift.

Emily Chang 1:08 This would be my kids' favorite.

Brian Chesky 1:09 Chesky's Charms.

Emily Chang 1:09 Chesky's Charms.

Brian Chesky 1:10 So you have Chesky's Chips, Chesky's Charms. I love this house. Like-

Emily Chang 1:14 It's beautiful, honestly. It's gorgeous.

Brian Chesky 1:16 And it's a nice balance 'cause, you know, I live alone. I didn't want to have, like, a, you know, weird tech McMansion. You know, the, the... I'm not gonna-

Emily Chang 1:21 Like super modern. Yeah.

Brian Chesky 1:22 I'm not gonna name names.

Emily Chang 1:23 [laughs]

Brian Chesky 1:23 But, you know, people my age buying $100 million homes-

Emily Chang 1:26 Yeah, yeah, yeah

Brian Chesky 1:27 ... not my thing.

Emily Chang 1:27 [laughs]

Emily Chang 1:31 What's it been like playing host so far?

Brian Chesky 1:33 Oh my God, it's been, it's been a lot of fun. Um, uh, I'm a co-host. I got Sophie, Supernova.

Emily Chang 1:38 [laughs] True.

Brian Chesky 1:39 She's a nearly one-year-old, a two-year-old golden retriever.

Emily Chang 1:42 Uh-huh.

Brian Chesky 1:42 It's been cool 'cause I haven't really hosted that much since the early days.

Emily Chang 1:46 You're kinda busy. You're running a multi-billion dollar company. Like, what made you wanna make time for this?

Brian Chesky 1:53 I never wanted to be one of those CEOs that's kind of an ivory tower, just looking at data and spreadsheets all day. When you first build a company, you make something usually for yourself.

Emily Chang 2:03 Mm-hmm.

Brian Chesky 2:03 People aren't just numbers, they're people, and that means that you need to be emotionally connected to what you're doing.

Emily Chang 2:08 Mm-hmm.

Brian Chesky 2:08 I understand when hosts are complaining about something or your customer's complaining, what do they mean? So that's like the main reason I did it, but then there was another reason I wasn't expecting, which was it's fun.

Emily Chang 2:20 It was crazy to think you were gonna rent your house to a stranger-

Brian Chesky 2:22 Yeah

Emily Chang 2:22 ... or that you were gonna stay in some stranger's house.

Brian Chesky 2:24 Totally.

Emily Chang 2:24 And now it's just what we do.

Brian Chesky 2:25 Yeah.

Emily Chang 2:26 Does the level of human openness to that idea still surprise you?

Brian Chesky 2:32 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.

Emily Chang 2:44 [laughs]

Brian Chesky 2:44 And I ended up becoming friends with these people. And it made me realize that, like, these homes are these private spaces that you, you never let anyone in, 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 that spread around the world.

Emily Chang 3:02 Mm-hmm.

Brian Chesky 3:03 I think we have trouble imagining sociological change is sometimes harder than technological changes.

Emily Chang 3:09 Mm-hmm. Mm.

Brian Chesky 3:09 We can all imagine things getting bigger, faster, but it's hard to imagine us changing behavior.

Emily Chang 3:13 But Airbnb has actually been a big part of, like, maybe a major sociological change.

Brian Chesky 3:18 Probably. I mean, it's been now w- been used 1.4 billion times.

Emily Chang 3:23 Mm.

Brian Chesky 3:24 And if you had told me when we first started that 1.4 billion people from 220 countries and regions would live together, that on a typical night we'd have nearly the population of Los Angeles-

Emily Chang 3:36 Mm

Brian Chesky 3:36 ... staying together, people from the Middle East and Texas-

Emily Chang 3:38 Oh

Brian Chesky 3:38 ... like cultures you wouldn't necessarily think mixing together, I think we all would've said, "You're crazy." It's like most tech companies have to understand laws of physics.

Emily Chang 3:46 Mm.

Brian Chesky 3:46 We call these first principles.

Emily Chang 3:47 Mm.

Brian Chesky 3:48 And we also have to n- 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.

Emily Chang 3:57 You know, obviously the pandemic hits, travel comes to a screeching halt. The majority of your revenue-

Brian Chesky 4:02 Oh, yeah

Emily Chang 4:02 ... almost vanishes. Also, nobody wants to see other people.

Brian Chesky 4:06 Right.

Emily Chang 4:07 In that moment, did it feel like you were standing on the edge of a cliff?

Brian Chesky 4:11 I thought we had made it before the pandemic. You know, we had a business that was doing, like, let's call it $35 billion in sales.

Emily Chang 4:17 Mm.

Brian Chesky 4:17 That's more than Starbucks.

Emily Chang 4:18 Mm.

Brian Chesky 4:19 That's almost, like, the size of Nike. If you had told me in, like, the 1980s growing up we'd have a business that big-

Emily Chang 4:23 Mm

Brian Chesky 4:23 ... I'd be like, "You're totally crazy." I thought we were making it. We're working on an IPO. To then lose 80% of it in eight weeks? I mean, you remember there were articles like, "Is this the end of Airbnb?"

Emily Chang 4:32 Mm.

Brian Chesky 4:32 "Will Airbnb exist?"

Emily Chang 4:34 Mm.

Brian Chesky 4:34 I gotta tell you, like, that changed my life, and it changed my life and the company for the better.

Emily Chang 4:39 How?

Brian Chesky 4:40 You ever hear people say, like, they had a near-death experience and they had this moment of clarity? Well, thankfully I've never had that, but I felt like I got that clarity-

Emily Chang 4:49 Mm-hmm

Brian Chesky 4:49 ... from a business perspective.

Emily Chang 4:50 How did you change as a person?

Brian Chesky 4:52 We'll see. My hair is a little grayer.

Emily Chang 4:53 [laughs]

Brian Chesky 4:54 But, um, I think I really grew up during the pandemic. I think I felt my responsibility more.

Emily Chang 4:59 Mm.

Brian Chesky 4:59 Employees were worried about their jobs. Investors were worried about their investment. Guests were worried about if they can get their money back when they're traveling. And they were all reaching out to me at the same time, and not in a low-key composed way. And I remember my board member, Ken Chenault, who's the CEO of Amex, he was CEO during 9/11 and the financial crisis of 2008, and he basically said, "I've been through two of the biggest crises of my lifetime, and this is 10 times bigger than either of them." He said, "This is your defining moment as a CEO." And I think I had lessons that have now been seared in my brain, and I'm never gonna forget them.

Emily Chang 5:31 What are the lessons?

Brian Chesky 5:32 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. I learned to focus the entire company and point them, every single person, to one direction. And I learned to stop apologizing about how I wanna run the company. 'Cause 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.

Emily Chang 6:04 Mm.

Brian Chesky 6:05 It's like 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 'cause they had clarity and direction.

Emily Chang 6:17 And then the tide turned, or maybe it's like the Titanic didn't hit the iceberg. You go public, Airbnb goes public-

Brian Chesky 6:23 Yes

Emily Chang 6:23 ... the end of 2020. I'm interviewing you live. You can't even speak. [laughs] Like, you're completely tongue-tied.

Brian Chesky 6:29 Yeah.

Emily Chang 6:29 I actually want you to, I want you to watch it. It's such a moment. We just got indication on your opening price. Uh, shares indicated to open right now at $139 a share, which is-

Brian Chesky 6:38 [laughs]

Emily Chang 6:38 ... more than double what you priced at. I mean, are you at all concerned about froth? Y- what do you think about that number and the potential, uh, that you're leaving billions of dollars on the table?

Brian Chesky 6:51 That's the first time I've heard that number.

Emily Chang 6:52 [laughs]

Brian Chesky 6:53 Um, that is, that's a, I, you know, when we- [laughs] In April we raised money, um, and it was a debt financing.

Emily Chang 7:03 Oh my God.

Brian Chesky 7:03 It, it, that price would've priced us around 30 bucks. So I, I don't know what else to say. It- it's that, that's a, this a, it's a very, that, that's, um-

Emily Chang 7:14 Wow.

Brian Chesky 7:16 I haven't watched that in a long time. Wow. That actually makes me a little emotional.

Emily Chang 7:23 What's going through your head in that moment?

Brian Chesky 7:25 Um, I think that moment, the, it was like my hard drive crashed, and I think it's that, like, the pandemic happens, we have this emergency board meeting. All of a sudden I realize, like, this is gonna be a 24-hour thing, and I probably never stopped at any point to think about anything. You took a whole year and you made it like a 15-second trail run. I was like, oh my God, and it just... And maybe at that moment it all hit me. This is just so crazy.

Emily Chang 7:52 The interview went viral.

Brian Chesky 7:54 It did. [laughs]

Emily Chang 7:55 People could see it hit you.

Brian Chesky 7:57 Yeah. Yeah, yeah. My eyebrows went to the top of my head.

Emily Chang 7:59 [laughs]

Brian Chesky 8:00 And, um, I didn't know they went that high. That was, that was one of the most surprising moments of my life. I'm not usually speechless. I mean, 2020 was an intense and emotional year, and that was the capstone.

Emily Chang 8:11 Do you ever think about where Airbnb would be if the pandemic didn't happen?

Brian Chesky 8:15 That's the crazy thing. Like, your culture is often forged in your darkest moments. Uh, but I think people think of culture as, like, you know, the perks, the yoga, free food, snacks. No, culture are 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, the things that forged you. We basically made like five years of progress in, like, six months, and you can't ask for an occasion like that.

Emily Chang 8:41 Mm-hmm.

Brian Chesky 8:41 You can only hope that if it happens you will rise.

Emily Chang 8:45 We've seen a lot of founder CEOs step back, whether it's, you know, Amazon, Google, Twitter, Pinterest, Slack. You're still here.

Brian Chesky 8:56 I think when I was starting out, I think I was afraid to run a giant company. But the thing that's most surprised me is I have more excitement today than I did when I was in Y Combinator.

Emily Chang 9:05 Hmm.

Brian Chesky 9:06 The job today as a public company CEO is more fun-

Emily Chang 9:10 Really?

Brian Chesky 9:10 ... than the job as a private company CEO.

Emily Chang 9:12 I feel like I often hear the opposite.

Brian Chesky 9:14 You often do because, you know, by the time you run a public company, you're trying to appease shareholders, you're trying to appease employees, you're negotiating. I stopped obsessing over making money, and we end up generating three and a half billion of free cash flow.

Emily Chang 9:24 Hmm.

Brian Chesky 9:25 There's a paradox there. I like to tell entrepreneur, think of the growth of your company, you have to grow faster than that, and if you don't grow faster than your company, then your company is gonna be pulling you, and then you're gonna eventually be holding it back.

Emily Chang 9:37 Does it ever feel like this immense responsibility that you have to stay, or does it feel like a burden?

Brian Chesky 9:44 I only want to keep doing this if I'm the best person to do this, and the interest in me is the longer I do it, the more I probably become the best person because I have both the history of the founder, of 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. I think that our day's just getting started. We're like phase one, have an idea, bring it to market, get product market fit. Phase two, hyper-growth. Phase three, become a public company and, like, generate profit and be a real company. Phase four, reinvent yourself. Ostensibly I'm an entrepreneur and a business person, but I, 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 it used to be.

Emily Chang 10:30 Are you an artist designer first and CEO second? Is that what you would say?

Brian Chesky 10:34 I think you're always what you were growing up. You know-

Emily Chang 10:38 Hmm

Brian Chesky 10:38 ... 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 set the intersection.

Emily Chang 10:46 Mm. And how does that change the company? How is that mentality infused into the company?

Brian Chesky 10:50 I have, like, books like this Frank Lloyd Wright book here, right?

Emily Chang 10:53 Mm-hmm.

Brian Chesky 10:53 My favorite architect, or Charles and Ray Eames, two of the great industrial designers of the 20th century. Charles Eames 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, it's how it fundamentally works.

Emily Chang 11:09 Mm-hmm.

Brian Chesky 11:10 It's about simplifying something.

Emily Chang 11:11 Mm-hmm.

Brian Chesky 11:12 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.

Emily Chang 11:19 Mm-hmm.

Brian Chesky 11:19 Even, like, how we became profitable, I like, I, we kinda designed the P&L.

Emily Chang 11:24 Hmm.

Brian Chesky 11:24 You know? Like, most people cut. We didn't cut, we designed.

Emily Chang 11:27 Mm-hmm.

Brian Chesky 11:27 'Cause cutting, you're just, like, lopping things off.

Emily Chang 11:30 Mm-hmm.

Brian Chesky 11:30 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.

Emily Chang 11:41 What's a day in the life of Brian Chesky outside the office?

Brian Chesky 11:44 I like to learn, I like to draw, I like to hang out with people I care about, and I like to travel.

Emily Chang 11:48 Mm-hmm.

Brian Chesky 11:49 I guess those are the things I do.

Emily Chang 11:51 I love your art.

Brian Chesky 11:54 Yeah. So this is all, this is my life before tech.

Emily Chang 11:56 Did you do these?

Brian Chesky 11:57 Yeah. So I did, I did this in, uh, freshman year RISD. This is, like, 1,000 triangles glued together to turn into a self-portrait.

Emily Chang 12:05 I didn't realize you were such an artist. I mean, I kne- knew you were a designer, but-

Brian Chesky 12:09 I feel probably, yeah, more a artist, uh, artist... I started as an artist, became a designer, then I guess a entrepreneur, in that order.

Emily Chang 12:21 Is this another one of yours?

Brian Chesky 12:22 Yeah. So this was, like, my big high school senior project. This is me basically hanging off a ledge of the Grand Canyon.

Emily Chang 12:30 [laughs] There's a lot going on there.

Brian Chesky 12:33 Probably highly symbolic to how I felt senior year of high school.

Emily Chang 12:36 Which was?

Brian Chesky 12:37 Like, "Oh my God," like, "my life is changing so much."

Emily Chang 12:40 Mm.

Brian Chesky 12:40 I was planning to go to art school. I thought I'd be an artist. I, at that point, I didn't even think I'd be a designer. Designer was, like, a leap.

Emily Chang 12:46 Yeah.

Brian Chesky 12:46 And I had to who- go the whole journey of realizing, like, I love drawing, and then I get to campus, and I realize I was born, like, 100 years too late for what I wanted to do. Freshman year of RISD, you have to pick a major, and the department head of industrial design came to pitch. And they said, "Industrial design is design of everything from a toothbrush to a spaceship and every single thing in between." And I thought to myself, "That's what I'm gonna do with my life."

Emily Chang 13:10 So Airbnb was the thing in between.

Brian Chesky 13:12 I guess we're between a toothbrush and a spaceship. [laughs]

Emily Chang 13:14 [laughs]

Emily Chang 13:17 Over the years, you've really emphasized and, you know, the values of Airbnb, whether it's community or connectedness.

Brian Chesky 13:23 Yeah.

Emily Chang 13:23 What does it take to make something that people really love?

Brian Chesky 13:27 When I joined Y Combinator, the first day, they give you a T-shirt. It's a gray T-shirt.

Emily Chang 13:33 Mm.

Brian Chesky 13:33 And it says, "Make something people want." And if you get an exit, they send you a black T-shirt.

Emily Chang 13:38 [laughs]

Brian Chesky 13:38 And it says, "I made something people want." And that was something that always stuck with me. And I think the way you make something that people want is you have to care about people.

Emily Chang 13:47 Mm-hmm.

Brian Chesky 13:48 And you have to understand people.

Emily Chang 13:49 Mm-hmm.

Brian Chesky 13:50 We did this thing 10 years ago. I named it Snow White after the movie Snow White. Snow White was basically the advent of the storyboard.

Emily Chang 13:56 Mm-hmm.

Brian Chesky 13:57 Walt Disney's one of my heroes. This film was so long, he had to storyboard it. And I said, "Why don't more businesses 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 just every single opportunity is a detail that you could perfect?"

Emily Chang 14:14 Talk about being in the details.

Brian Chesky 14:16 Oh, yeah.

Emily Chang 14:16 I mean, is your team like, "Should we invite Brian [laughs] or not?"

Brian Chesky 14:20 If they had the choice-

Emily Chang 14:21 [laughs]

Brian Chesky 14:21 ... but that, you're presuming they have a choice.

Emily Chang 14:23 [laughs]

Brian Chesky 14:24 I don't intend to be in the details of everything forever. It's like I'm a coach, and I'm, like, trying to teach a level of detail and excellence. I think there's this, like, 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 gotta be in the details of the people. It's not micromanaging. It's auditing and understanding-

Emily Chang 14:49 Mm-hmm

Brian Chesky 14:49 ... what they're doing.

Emily Chang 14:50 Tech is going through a tumultuous time.

Brian Chesky 14:51 Oh, yeah.

Emily Chang 14:52 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?

Brian Chesky 15:01 I always felt like when I would read some of these corporate communications that, like, they weren't written from, by people. They seemed to be, like, written by committees. And it felt like maybe a bunch of lawyers or HR people had sanded the edges off the person to the point where the person speaking wouldn't actually talk like that. Any communication, I write. A lot of CEOs don't write anything that th- they have their name on. The second thing is, I think when you do a, like, a layoff, if you're gonna 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 will ever end. And the company is, like, in a paralyzed standstill if that happens.

Emily Chang 15:44 You started Airbnb at the depths of a financial crisis, 2009.

Brian Chesky 15:48 Yeah.

Emily Chang 15:48 What's your advice to entrepreneurs now?

Brian Chesky 15:52 I mean, I honestly think [laughs] ...

Emily Chang 15:56 Hi, Sophie.

Brian Chesky 15:57 Sophie.

Emily Chang 15:58 She's like, "This is going on a really long time." [laughs]

Brian Chesky 16:01 Um-

Emily Chang 16:02 I get it. We've been talking a while. Hello. I think she likes me.

Brian Chesky 16:08 [laughs]

Emily Chang 16:10 [laughs] All right. What's your advice? Look, it's like-

Brian Chesky 16:15 Yeah

Emily Chang 16:15 ... banks are collapsing. Like, what's your advice to entrepreneurs right now?

Brian Chesky 16:20 I think this is a great time to start a company. If you look at the history of companies like Apple and Microsoft, I think we're starting in a down economy. Google emerged during the dot-com crisis. We started during the Great Recession. I like to tell people the best time to start a company is the moment you're ready. 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 the discipline of being in a really difficult environment will teach you something.

Emily Chang 16:46 So what do you want the next phase of Airbnb to be, say, five years?

Brian Chesky 16:50 I feel like at this point, we have all these capabilities. It would be such a shame not to use that to solve a very important problem.

Emily Chang 16:57 Mm-hmm.

Brian Chesky 16:57 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. If people lived this isolated, alone thousands of years ago before modern technology, we would be dead, right? There's a reason loneliness hurts. It's because-

Emily Chang 17:12 And the, some people would say, like, tech is connecting us all and making us less lonely.

Brian Chesky 17:15 Loneliness has been rising in the United States since the 1970s, 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. The average American spends 10 more hours alone every week than 10 years ago. We're sleeping less, exercising less, spending less time with friends and family. You know, your Instagram followers aren't coming to your funeral. No one changed someone else's mind in the YouTube comments section. So we need to marry the best of the digital technology with the best of the physical world. I want the next chapter of Airbnb, I want it to be less about housing, less about travel, but new things we're gonna do are gonna be a lot more about bringing people together.

Emily Chang 17:50 [upbeat music] This isn't bad.

Brian Chesky 17:57 Not bad at all.

Emily Chang 17:58 It's so beautiful.

Brian Chesky 17:59 Yeah, Sophie loves it here. I mean, look at this view of the city.

Emily Chang 18:01 It's amazing.

Brian Chesky 18:02 See, here we are, Dolores Park.

Emily Chang 18:05 I mean, you've been doing this for, like, 15 years.

Brian Chesky 18:07 Yeah.

Emily Chang 18:07 15 years. That's a long time.

Brian Chesky 18:08 That is a long time-

Emily Chang 18:09 Does it ever get-

Brian Chesky 18:09 ... in tech standards

Emily Chang 18:10 ... does it ever get, like, lonely at the top?

Brian Chesky 18:12 Oh, yeah. You can have all the money in the world, all the success in the world, but the thing that makes most people happy is just connections and relationships.

Emily Chang 18:20 You talk about your parents and your family a lot. Do you want A family? Like, do you want that for yourself?

Brian Chesky 18:25 Oh, yeah, definitely. It's probably the one thing I haven't done. I got a dog. That was a starting- [laughs]

Emily Chang 18:28 [laughs]

Brian Chesky 18:29 I'll be like, "Let me take care of-

Emily Chang 18:30 She's family.

Brian Chesky 18:30 "Let me take care of something really, like, low-key first." If you had told me in my 20s what my life would be like at 41, I would have told you I'd have a family and maybe I wouldn't be that far in my career. And now I have, like, a huge public company, and I don't have a family. And so I did things in a different order-

Emily Chang 18:46 Yeah

Brian Chesky 18:46 ... and the last 15 years has been work and all-consuming-

Emily Chang 18:49 Yeah

Brian Chesky 18:50 ... Airbnb.

Emily Chang 18:51 So what's the goal for the next 10 years of Brian Chesky?

Brian Chesky 18:55 I think I have to do things I haven't done before. As long as you're in a constant state of becoming and changing and growing, you're gonna be okay.

Emily Chang 19:02 Mm.

Brian Chesky 19:02 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.

Emily Chang 19:08 You obviously, you lived around the world in Airbnbs. You've interacted with so many cities and, and people in different countries.

Brian Chesky 19:15 Yeah.

Emily Chang 19:15 And many of them welcomed Airbnb with open arms-

Brian Chesky 19:19 Yeah

Emily Chang 19:19 ... and some are still resisting.

Brian Chesky 19:21 Yep.

Emily Chang 19:22 Why do you think that is?

Brian Chesky 19:24 So every city's a community, and every community has many different stakeholders, and they have many different circumstances. Some cities need more tourism. Other cities have been going through a housing affordability crisis, and they're very, very sensitive about housing getting taken off the market.

Emily Chang 19:37 Yeah.

Brian Chesky 19:37 And so the lesson I've learned is you gotta, like, there's no one-size-fits-all.

Emily Chang 19:41 Mm-hmm.

Brian Chesky 19:41 You have to treat every city personally, try to make a system for them that works.

Emily Chang 19:45 People think Airbnb is driving up costs, enriching landlords, bringing in floods of tourists, changing the character of a place. Like, what do you say to the people who are like, "I, I hate what this is doing in my community"?

Brian Chesky 19:59 Well, I never want Airbnb to do anything other than strengthen a community.

Emily Chang 20:02 Mm-hmm.

Brian Chesky 20:03 I also think it's really important to never presume that we're the good guys. Is what we're doing, like, good for the world?

Emily Chang 20:09 Mm-hmm.

Brian Chesky 20:09 And to constantly reevaluate. And so for example, affordable housing. A lot of cities said, "You know, we wanna have some basic restrictions on how Airbnb can be used in our city." So we have, like, we comply with registration systems-

Emily Chang 20:21 Mm

Brian Chesky 20:21 ... for cities. We wanna make sure that, like, cities say they wanna be able to-

Emily Chang 20:24 Mm-hmm

Brian Chesky 20:24 ... that we have to collect our fair share of taxes.

Emily Chang 20:26 Mm-hmm.

Brian Chesky 20:26 But I also want people to know that we wanna strengthen communities, and if that means that they need to, like, change the way Airbnb exists in their city, we'll have that conversation.

Emily Chang 20:36 Are you long SF, San Francisco?

Brian Chesky 20:39 I think I am ultimately. I think the city's, my God, has, had its fair share of challenges, and I think that I'm saddened that the tech community and the city haven't worked better together. That being said, this city is so resilient.

Emily Chang 20:53 Yeah.

Brian Chesky 20:53 And just when people said there was gonna be a massive exodus, there is a new kind of probably the word revolution is not an understatement to say what's gonna happen to AI, and a lot of it's happening right here.

Emily Chang 21:04 How do you think AI is gonna change Airbnb?

Brian Chesky 21:06 I think we can design some of the best interfaces for AI in the world, and I think what I ultimately wanna do is imagine one day the app is more like a concierge-

Emily Chang 21:14 Mm-hmm

Brian Chesky 21:14 ... that knows you. It can match you to the perfect Airbnbs. Can ... I think that's ultimately what it could do.

Emily Chang 21:19 All right. Well, you know what would make this world a little more perfect?

Brian Chesky 21:22 Tell me.

Emily Chang 21:22 Chocolate chip cookies.

Brian Chesky 21:23 All right. Let's do it.

Emily Chang 21:24 [laughs] Let's do it.

Brian Chesky 21:24 Sophie-

Emily Chang 21:25 I'm hungry

Brian Chesky 21:25 ... you want cookies? All right. She-

Emily Chang 21:26 [laughs]

Brian Chesky 21:27 That's exactly what she wants. The key to a good chocolate chip cookie is lots of brown sugar, lots of vanilla extract.

Emily Chang 21:35 Mm. Mm-hmm.

Brian Chesky 21:35 That's pretty much all you need to know.

Emily Chang 21:36 I have a chocolate chip cookie recipe, too, so I'm very excited to see-

Brian Chesky 21:39 We're gonna have a-

Emily Chang 21:39 ... what your secrets are

Brian Chesky 21:40 ... little bake-off. You see-

Emily Chang 21:41 Do you like baking in general? Is this, like, a thing of yours?

Brian Chesky 21:44 I do. It's like, it's a little, like, reminds me of, like, drawing. Drawing is like baking, and painting's like cooking. How many chips you put in?

Emily Chang 21:53 I like less chips than more.

Brian Chesky 21:54 Me too. Oh.

Emily Chang 21:56 I prefer more cookie than chip.

Brian Chesky 21:57 Does that seem good?

Emily Chang 21:58 That looks great.

Brian Chesky 21:59 So now we have dough. All right, so ready? We're gonna do, like, this piece. I'm gonna try that.

Emily Chang 22:04 Okay.

Brian Chesky 22:06 This is the test, isn't it?

Emily Chang 22:07 Mm. Mm.

Brian Chesky 22:09 It's pretty good, right?

Emily Chang 22:10 Mm-hmm.

Brian Chesky 22:11 All right.

Emily Chang 22:11 Yeah.

Brian Chesky 22:11 So now, yeah, we are-

Emily Chang 22:15 Mm.

Brian Chesky 22:15 Yeah. They're kind of... If you have those 16 chefs-

Emily Chang 22:18 You need help?

Brian Chesky 22:18 Yeah, yeah, yeah.

Emily Chang 22:18 All right. So we're gonna ask a couple real questions.

Brian Chesky 22:21 Yeah.

Emily Chang 22:22 What's overhyped?

Brian Chesky 22:24 Crypto was overhyped, and now it's not, but crypto was overhyped. I think AI is probably appropriately hyped, but there is a s- risk that people will have unrealistic expectations of what it can do going forward.

Emily Chang 22:38 Mm-hmm.

Brian Chesky 22:39 Like, the whole world has to move with the technology, or the technology will get ahead of itself, so.

Emily Chang 22:43 How, how much do you really want AI in your life? Like, would you want ChatGPT in your kitchen?

Brian Chesky 22:47 There is such a thing as too much technology in our life. Technology is not inevitably a solution to our problems. Technology is a tool. It's power, and power can make things better, and it can also make things worse. It can simplify our lives or add complexity.

Emily Chang 23:01 Mm-hmm.

Brian Chesky 23:02 It can bring us together or divide us, and the speed at which things are about to change is something that we have to be very careful about. 10 minutes.

Emily Chang 23:11 It's 10 minutes.

Brian Chesky 23:12 And it's ready.

Emily Chang 23:13 Yeah.

Brian Chesky 23:13 All right, let's see what they look like.

Emily Chang 23:14 Let's do it.

Brian Chesky 23:16 And here they are.

Emily Chang 23:17 Yum. Oh, my gosh. They look amazing.

Brian Chesky 23:19 And boom, there they are. Look at that.

Emily Chang 23:20 Okay. Shall we?

Brian Chesky 23:21 Let's do it.

Emily Chang 23:22 Okay. Cheers.

Brian Chesky 23:24 Cheers.

Emily Chang 23:28 Mm.

Brian Chesky 23:28 Mm.

Emily Chang 23:29 These are 10-star cookies. I was, I was skeptical.

Brian Chesky 23:33 I know. I know. It's, it... How can you believe greatness until you see it, you know? [upbeat music]