BRIAN CHESKY: The pandemic, you know, hit. People were predicting this is the end of Airbnb. Is Airbnb going to exist? And so, in my darkest moment, you were the first podcast I ever did and you were the first person I ever told the story to. And I just really appreciate that like you and I have been on this journey. The next podcast I did was the recovery, the comeback. Then the next one was the IPO. And I would describe this as the next chapter of Airbnb — Airbnb going beyond homes and truly entering this new creative place.  

BOB SAFIAN: That’s Brian Chesky, co-founder and CEO of Airbnb, who is about to take us into a deep, revealing look into the Airbnb of today and of tomorrow. We’ll start with his approach to Airbnb’s earnings releases, the most recent of which he announced just a couple days ago. And then we’ll dig into Airbnb’s new initiative around Icon stays, inspired by the Barbie Malibu Dream House. And surprise, that program offers a hint about how Airbnb will be moving into new creative places. 

We’ll also talk about what he and Apple’s longtime designer Jony Ive have been collaborating on, how he’s applying AI to Airbnb. Plus, Brian talks about his biceps and his bodybuilding regimen, and more. It’s so jam-packed, our session will unfold in two parts. Part 2 will release on Friday, available only through the new Rapid Response feed, so please subscribe on Apple, Spotify, wherever you get your podcasts. I’m Bob Safian, former editor in chief of Fast Company, founder of the Flux Group and your host. This is Rapid Response.

[THEME MUSIC]

I’m Bob Safian, and I’m here with Brian Chesky, the founder and CEO of Airbnb. Brian, it’s good to be here with you in person.

CHESKY: It’s good to be here with you as well. I’m excited to be back.

SAFIAN: So first of all, welcome to New York or welcome back to New York. I know you grew up in New York.  

CHESKY: Upstate New York. 

SAFIAN: Yeah. You’ve had a busy month. You were in LA for an event, Then you come here to New York to do an earnings release. Where do you stay when you’re in New York? Do you have a regular place?

CHESKY: At this point, I stay with my sister. I stay at my sister’s apartment in Tribeca. You know, the whole original premise of Airbnb was the experience of staying with a close friend in the city. Well, you know, when I have close friends, if they’re willing to still have me, then I’ll still do that too.

SAFIAN: Yeah. A sister counts in that regard. 

CHESKY: I think a sister counts, and she’s one of my closest friends. 

Running a public company vs private

SAFIAN: Now I have to say, you’re here in New York for earnings. Earnings cannot be the most fun part of this job.

CHESKY: I will tell you, I do prefer launching new products than delivering the quarterly financial results. But I will tell you something — before I went public, I was forewarned by so many CEOs never go public, stay private as long as you can. And so I had a lot of caution about going public. I mean, when everyone tells you, and by the way, they didn’t just tell me, like, “people don’t like being public company CEOs.” A lot of people said, “you particularly will not like being a public company CEO.” And I’m like, “why me particular?” Maybe it would have something to do with me being a designer, having gone to RISD and why would a person like that enjoy the scrutiny of being a public company.

So I’ll tell you, having been public now for a little over three years and having done maybe a dozen or so earning calls, I actually kind of weirdly enjoy earnings calls. And I think being a public company CEO, I don’t want to diminish its difficulty, but I think it’s easier to be a public company CEO than a late stage private company CEO. Because when you’re a late stage private company, it is like you’re a public company. You have to have audit financials. You have an audit, you have an audit committee, you have a lot of scrutiny in the company. So you have a lot of the downsides of being public. But you don’t have the upsides, meaning like when you’re a private company and you’re really big, there’s always the sense that you’re hiding something. We’re not getting the full story. And so I think once we went public, it was like this pressure valve just released. And earnings calls I find are actually really good disciplines to brush up on the story, and I do find that the analyst and the investors are like super fair. I do think the market is like, you know, I’m never going to figure out the markets, but it’s not that bad. 

SAFIAN: As you’re talking, I was thinking, I had a discussion with Michael Dell when he took Dell private. And he said that one of the upsides for him of going private was that he wouldn’t have to share everything — that like not all of his competitors would know everything about what he was doing in the same way that he felt like he had to when he was public. 

CHESKY: Well, the good thing for you is I tend to be an oversharer. So that might not be what my team likes, but I think for you and everyone else that works.

Introducing Icons, Airbnb’s newest category

SAFIAN: So, last summer, you launched this Barbie Malibu Beach House that kind of went crazy when the movie went crazy. 

CHESKY: Went completely nuts. 

SAFIAN: Right? And now you’ve announced 11 Icon locations, right? From X Men Mansion to Ferrari Museum to Prince’s Purple Rain House, right? It almost seems like this opportunity, this idea sort of presented itself to you? Like the Barbie house kind of opened your eyes to things? 

CHESKY: A hundred percent. So basically the quick version of the story just to give some more background to Icons is ten years ago, I remember, I was with my co-founder and roommate. And we’re living at this apartment that we started the company in and we need to get some furniture. And of course, back then, IKEA would have been the place we would have gone. 

We get to an IKEA, we’re walking down the hallway and we see a bedroom, like, you know, those IKEA showroom bedrooms. And I remember saying to him, “Wouldn’t it be funny if we put this on Airbnb?” Like as a joke. And we started talking about it internally like a joke like, “we’re gonna’ list a night at IKEA.” Well, somebody in our Australian team, unbeknownst to me, hears about this idea and reaches out to some marketing executive in IKEA and they one day tell me like, “hey, we got this IKEA in Sydney, Australia on Airbnb.” So it gets listed on Airbnb and it becomes like a bit of a sensation.  

Then one day, somebody on our team says, “we have an idea to list Blockbuster on Airbnb. ”And I’m like, “Blockbuster?”

SAFIAN: I remember this.

CHESKY: I’m like, “I didn’t think there were any more Blockbusters.” It turns out there’s one left in Bend, Oregon. So we put it on Airbnb. It went all over the internet. It got thousands of press articles, probably got millions and millions of dollars worth of press.

So then last year, the Barbie movie is coming out. I think it was Mattel and Warner Brothers that reached out to us and they said, “can we do a promotion with Barbie?” ‘Cause they were going to do a bunch of these like Barbie marketing activations. And so we said, “sure.” So we found a house in Malibu, in the hills of Malibu that looked a little like the Barbie house. And we basically, like to the last detail, really like every corner of the space, we recreated it as if it was a Barbie Malibu Dream House.

SAFIAN: That is your way — to the last detail.

CHESKY: To the last detail. As Charles Eames said, “The details aren’t the details. They make the design.” And Walt Disney would look at like the back of a trash can. And I do think that everything is just an accumulation of details. I think that’s a good characteristic of design. But, so anyways, this Barbie house we put on Airbnb, it gets more press than the IPO. And we’re like, “what the hell?” The universe is telling me that the world wants this. 

SAFIAN: So there’s not necessarily a strategy behind it. There’s just like a feeling that there’s an opportunity here. 

CHESKY: At this point, it was purely a feeling. In hindsight, we backed into a strategy and sometimes things start with a strategy. Sometimes things start with, like, “we need more engagement and we need blah, blah, blah.” But I got to tell you, Bob, sometimes I honestly think the best ideas start with a vision. They start with an idea. They start with a feeling, and then you validate them by reverse engineering a strategy to make sure what you’re doing actually makes some sort of modicum of business sense. 

So it’s October and I rally the team together. This is only like six, seven months ago. And I said, “we need to create a platform for Barbies. I want to be able to come to Airbnb and see a whole series of Barbies on the homepage. But I don’t just want them to be stays. Because I want them to be experiences. In fact, I want all these to feel like they’re experiences, not stays. Because this is going to be a bridge to where we’re going. We’re going to eventually relaunch experiences.” And I said this can be the way to do that. 

Recreating the house from “Up”

So we huddle together. And, you know, probably my favorite concept that the team came up with is the Up house. And the Up house, Up was one of my favorite movies.

And I said, “if we’re going to build this Up house, you better make sure it is down to the last detail because people have been to Disneyland and their expectation is that it is done to the level of Disneyland craft and it can’t look like a Disneyland knockoff.” 

You know, you open the mailbox and there’s brochures and they’re graphic designed. It’s that level of detail. So we do that, we design this house. It takes like a hundred people to do. We assemble like fabricators, prop designers. We had to assemble like a team of a hundred people to build this house. Then I have this thought. I said, “wait a second, I know we’re going to build a house. But if it doesn’t go in the sky, it’s not really the Up house.” And the problem is, most houses aren’t constructed to be lifted in the air. 

SAFIAN: No, they’re supported by the ground, right?

CHESKY: And so if you lift a house, it collapses. There’s no structural integrity. So we ended up working with structural engineers to figure out how can you construct a house that’s 40, 000 pounds that can be lifted 50 feet in the air? 50 feet, 5 stories in the air. And above it, we’ll have 8, 000 balloons. Now, you can’t be helium balloons. Obviously, the physics doesn’t actually work out. You’d need, like, the biggest helium balloons in the world. And in fact, they deflate. You’d like, fall to your death. So you can’t do that.

So we ended up creating a steel structure. And then we found the biggest crane in the world, or one of the biggest cranes in the world. And these cranes are basically used for windmills, those like wind farms. And we had to work with safety experts to figure out how the house doesn’t rock and we had to work with meteorologists because it turns out about 11 miles an hour is the amount of wind that a house can withstand before the rocking becomes dangerous and the props basically just dismantle. We found land in New Mexico where they filmed Oppenheimer. It kind of looks a little like Venezuela, so where the film takes place. And so that’s just one of the Icons. We do this for like 11 of them. 

Given the response of Barbie, I knew if we put out Icons, number one: we’d remain top of mind. Now, everyone knows Airbnb, but like our competitors spend 4 or 5 billion dollars a year on performance marketing to stay top of mind and everyone knows of them too. So we’re in an industry where even if people know you, people only come to your app once or twice a year, not like Instagram because you’re travel. So you have to remain top of mind.

The second thing is: we’re in every country in the world, with only a few exceptions. But this was the best way to reach certain audiences. We want to reach the community in India? Who’s the biggest Bollywood star? Let’s work with one of them. So it really works. 

And the third thing is the Airbnb brand on the one hand is pretty amazing. Like it’s a noun and a verb. It’s one of the only brands that is like Xerox or Kleenex, right? It means something. The problem is: It’s a noun and a verb that means a B and B, a place to stay. It’s almost like if Nike meant running shoes, how do you sell basketball shoes?

SAFIAN: Right? It becomes narrow. 

CHESKY: It becomes narrow. So it turned out that by building this platform for Icons,

It kept us top of mind. It allowed us to reach all these segments, and it became a gateway to people thinking about Airbnb, not just for stays, but experiences. And that allows us to pave the way for the next few years.

The ROI of Icons

SAFIAN: Yeah, I mean, as you’re talking about the Up house, clearly it costs you a lot of money, you know? 

CHESKY: Yeah. 

SAFIAN: It’s expensive. And when I think about the other things that you and I have talked about, you know, pandemic and IPO and whatever, like 11 listings on a service the size of Airbnb can seem kind of modest. 

CHESKY: Yes. A hundred percent.

SAFIAN: Like why spend all that money on just that? But as you’re talking about it, like this is a strategic decision, investment in brand and awareness, the reputation and perception of what Airbnb is and could be. 

CHESKY: There’s two things. Number one: while we don’t spend nearly as much as our competitors in marketing. Just to back up. So travel is an industry where people spend a lot on marketing. Our competitors, like some of the biggest OTA spend almost 40 percent of their revenue on marketing.

So I was like, “that’s a lot.” It’s a very marketing-driven industry. We spent about half what our other competitors spend on marketing, but we still spend over a billion dollars a year in marketing, right? So this is a very marketing-driven industry. So it turns out that If you consider this a marketing expense, this is some of the highest ROI marketing you can do. So it’s just like, versus Google AdWords or TV ads or digital ads and Instagram or Tik Tok or Snap. How does this perform? And our theory is that this will be some of the best ROI that we’ll ever do for marketing. So that’s kind of number one.

SAFIAN: Because you get so much earned media basically?

CHESKY: Basically. I mean, we’ve had nearly 10, 000 articles written about us and it’s almost twice as much coverage as the IPO. What’s an IPO worth? People say it’s tens of millions of dollars of free marketing. This was way more than that. This I think also was a brand repositioning for us a little bit. 

But there’s another reason that we did it. And it kind of brings me back to Walt Disney. Before Walt Disney built Disneyland, he built a small train set in his backyard. And no one can understand why a guy that had this huge Hollywood studio, he was like one of the most famous people in the world, is spending all of his time on this little train set. He has Salvador Dali come to this set. And what he was doing was practicing. He was building the muscle at a small scale for something that was going to be unleashed to the world and eventually what was unleashed was Disneyland. Icons helped us build some muscle for something that we will unleash that will reach millions of people. 

SAFIAN: I mean, they’re Disney-like experiences, right? But you’re not going into the theme park business. Or are you thinking about how do you do the theme park business in an Airbnb way?

CHESKY: Yeah. I think you could think of it as like, we launched Experiences a long time ago. It got some traction, never really captured the public’s imagination like our core business. And I think one of the lessons was it was different, but not quite different enough. It didn’t quite have enough magic. So we said, “let’s start with something completely unscalable. That’s pure magic.” And by the way, they’ll be guaranteed to be sold out. There’s about 4, 000 tickets a year. So clearly these would be sold out and they’re going to be a low price.

And we’ll start with like the craziest of magic and just really then figure out how can we take that magic and then bring it to millions of people. And so we’re gonna’ start very high end with Icons, and then we’re moving to mass. It won’t be a theme park. I think it’s gonna’ reinvent the company and it’s gonna’ be the beginning of the next chapter of Airbnb and we’re gonna launch it next year. 

SAFIAN: Next year? Oh, I can’t wait to be back here again then, hearing about it. 

CHESKY: And I told the team one thing I said, “if we can make a 40,000 pound house float in the sky, we can do anything.”

SAFIAN: So I’ll confess that when I first heard about Airbnb’s Icons initiative, I thought it was a bit of a gimmick. But as Brian explains, it reinforces the brand’s relevance and currency by tapping into culture and celebrity. I also love how it emerged organically, unplanned, that Brian pulled on a thread Airbnb had explored before and leaned into it as an opportunity. And the fact that it unlocks the way to a new, expanded purview for the company, well, Brian has a few more new hints to share about that. 

After the break, we’ll dig into the head-to-head ad campaign he’s launched against hotels, the obsession about his biceps and his bodybuilding regimen, and more. Stay with us.

[AD BREAK]

Before the break, we heard Airbnb’s Brian Chesky talk about why he’s invested heavily in creating just 11 low-revenue stays called Icons. Now, we talk about how he’s recently gone on the offensive to compete against big hotel chains, what his exercise regimen teaches him about business, and how he manages the mental health toll of leadership — what he calls the “inescapable nightmare.” Let’s jump back in. 

Inside the ad campaign taking shots at hotels

So you’ve talked about sort of this long time message of Airbnb being around experiences and being local, feeling like you’re having a local experience.You’ve started running ads against hotels. That is sort of, I don’t know, directly going against the traveler marketplace. What is that about? ‘Cause it’s almost like you’re making fun of their reliability. Like it’s reliable, but it’s reliably maybe something you don’t want. 

CHESKY: Yeah. Let me talk to you about that campaign. So first of all, for the last 10 or 12 years, we’ve been the receiving end of a lot of contrast of Airbnb versus hotels.  It’s possible there’s been billions of dollars spent that we’ve been on the receiving end of in the last decade or dozen years. 

Most of the team that I have today on the marketing and creative side was actually at Apple and Chiat Day during the golden age of Apple. I hired someone named Hiroki Asai. He was the creative director at Apple. He brought in these two great creative directors, Scott Trattner, Eric Grunbaum.

Turns out, Scott Trattner and Eric Grunbaum created the Mac versus PC campaign. And I’ve always kind of wanted to do like an Airbnb versus hotel campaign. But I didn’t want to punch down, well actually punch up. They’re much bigger than us. I wanted it to be something that was endearing and lovable. And I didn’t want to do a campaign that said we’re better than hotels in every way.

In fact, If you need to stay one night and you’re on a business trip, I think hotels are better. And we have hotels in Airbnb, so it’s not like that’s blasphemy for me. Like, we own Hotel Tonight, and if you need a hotel, if you need a place tonight, get a hotel. 

But it turns out that 80% of our trips are two or more people. And if you’re traveling with a group, If you’re traveling with your family, it’s almost always better than a hotel. For every person who stays in Airbnb, eight or nine people stay in a hotel. And if we can get one of those people to stay in Airbnb, we will double the size of our company. And so how do we do that? We do that by not convincing them we’re better all the time, but convincing them that for those family trips and those group trips, just do an Airbnb. 

So now we have a concept. So then how do we make that concept an ad? I told our team, I said, “I want to explore a concept around Pixar-level 3D animation. And let’s find an iconic voiceover artist.” We ended up finding Claire Danes. She does it. And just make it kind of playful and fun, humorous. Making fun of them a little bit but not like totally destroying them, like just light and that became the genesis of this campaign. 

The punchline is it’s been the highest performing campaign we’ve ever done. I think great marketing is education. You’re educating people about some indisputable truth. It is an indisputable truth that it is just cheaper and you don’t have to go to bed at the same time and you can all sit around the kitchen.You can have a pool to yourself. Those are just indisputable truths. You can’t argue with them. Whether you want those or not, separate. 

Brian Chesky on his biceps and bodybuilding

SAFIAN: So when Icons was announced, and there was nearly as much social coverage of your biceps as of the house. 

CHESKY: I wasn’t expecting that. I’ve had these biceps the whole time.

SAFIAN: Yeah. 

CHESKY: Some reason people notice.

SAFIAN: I know you and I haven’t talked about this before but I understand you did bodybuilding when you were younger. 

CHESKY: I was 19. I was a competitive bodybuilder. 

SAFIAN: Yeah. So what is your routine like? Is it an outlet for you for frustration? Is it like meditation?  

CHESKY: It’s all the above, but like I started bodybuilding when I was 16, 17 years old. So I kind of joke. I wasn’t like a tech founder that had a midlife crisis. I had an adolescent crisis. So the reason I started bodybuilding is I was the same height I am now and I was 120/125 pounds. I was like, super skinny. I remember there was a program and I was listed 135 pounds and all the other players were like 180 pounds. So I started weightlifting And I remember telling my friends when I was 17, they were kind of like playfully teasing me that I was super skinny. I said, “Well, I’ll be the most muscular teenager in the country in two years.” And two years later, I was the seventh most muscular teenager in the country. I competed in basically the teenage Mr. America called the NPC Teenage Nationals and Collegiate Nationals. 

And I learned two lessons from bodybuilding that I brought to tech. The first lesson I learned is if you can change your body, you can change your life. It was almost like you can change your life and you can start inside out. The body is almost the most fundamental place. I mean, even like a lot of therapists, they might say, “start with your body.” It’s like trying to start with your thoughts, like start with your body. Start with something fundamental. 

The second thing about bodybuilding that it taught me, and this is really good for tech — you can’t get in shape in one workout. It’s just consistency. And I think there’s this narrative in Silicon Valley, in tech and business that like somebody has this flash of insight. And anyone who’s done this knows it’s not one idea. It’s a hundred thousand ideas and you don’t build a company in a day, just like you don’t get in shape in a day. And I think it teaches you that discipline and it’s very methodical and it’s actually very measurable. 

And yes, I think it’s an outlet. Like the amount of stress can drive you crazy and it’s driven a lot of people crazy. And I mean, no one talks about when you start a company, you grow it, no one talks about the mental health toll. The amount of people I know that’ve had like panic attacks. They’ve had to stop. They’ve kind of lost it like they’ve gone through really dark periods. No one talks about it. It’s a lot and you need an outlet. 

And I think maybe there’s two answers. One is health and fitness and the other is like good relationships. You can’t be alone. You need to lean on people. And if you have good relationships and you also have really good health, then you’re going to be healthy, both mentally and physically.Then you can totally sustain this. But if you don’t have good relationships and you’re not exercising, you’ll probably crack.

Reflecting on wins or moving on to the next

SAFIAN: You have a lot of energy and a lot of passion. And I know from your team that you’re always going. 

CHESKY: Always. 

SAFIAN: Do you take moments to step back and think about the progress you’ve made and reflect on it? Or is your impulse always the next hill, like the next… 

CHESKY: Kind of always the next hill. But you know, we launched Icons last week. Everyone was celebrating. And I went home that night and I started working on like next May. But that could either sound inspiring or dark. 

SAFIAN: Like you’re a lunatic!

CHESKY: A lunatic.

SAFIAN: Yeah. 

CHESKY: The way I’ve explained this is like, if I’m a rock climber, the part I like isn’t standing on top of rocks. The part I like is the climbing. And so I don’t do all this for the result. I do it for the process. And so I’m a little bit of a lunatic. But I love the act. But I will say, and you’re right about this and people close to me have said this,that you do also have to stop and take stock in what you’ve done and have some appreciation.  

SAFIAN: It’s not a bad thing. It’s not a bad thing to have a little gratitude and enjoy these moments.  

CHESKY: I do sometimes. I do sometimes do that. To be honest, it’s not my inclination to do that. My inclination Is to always push the boundaries. But it’s the inclination of the people I love around me to do that and to get me to stop.  

My fellow CEO friends aren’t like, “can you believe what you’ve done?” They don’t say that. None of us do. We’re like, “can you believe how far we are behind at AI?” And like, “someone’s ahead of us.” So all of us in Silicon Valley, like none of my peers are like, “yeah, this is amazing.” All of us are just egging each other on and someone’s always ahead of you and if they’re not ahead of you, you think they’re ahead of you. 

And then you hang out with your high school friends and college friends and they’re like, “this is so crazy. Do you remember when you were in high school and all you ever wanted was to like prove your mom wrong that you could get a job with health insurance?” And I’m like, “oh my god I guess I did that.” So that perspective is really, really important. 

And I think the positive Silicon Valley is we’re never complacent and we’re always reaching for the next thing. But obviously that comes at a cost and we’ve got to be connected to our roots a little bit. I’ve encountered a number of people in Silicon Valley that are not in touch with anyone in their past. If you meet somebody and not one of their friends they’ve had for more than 5 years or 10 years, that’s a little bit of an issue, potentially. You are maybe possibly disconnected from your roots and your past.

And the other thing I’ll just say, like being a CEO can be such a fun and rewarding job. It can also if you’re not careful, be at times a little bit close to an inescapable nightmare you can never escape. And the difference is your team. Imagine if you have an amazing team and you can really count on them and you can really trust them. Then it is like the most rewarding thing. I mean, I feel like I have more fun today and this sounds completely crazy, but I feel like my job today is more creative, more entrepreneurial than it was when we were 10 or 20 people. But that sounds completely counterintuitive.  

SAFIAN: Because the canvas is so much bigger? 

CHESKY: The canvas is so much bigger. But also I have such a great team. And it doesn’t mean that I don’t have to deal with some of the nitty gritty, but there’s so many intelligent, competent people that can absorb so much complexity that today I can almost feel like Mickey Mouse in Fantasia. You know, like in other words, it’s fulfilling. You’re like, “we should do this!.” And it happens. And when you don’t have the right team in place, it’s like you’re in a car and you turn left and nothing happens. And when you have a team and they can’t do their job, you end up kind of doing their job. That gets very intense.

And then what happens is, you start getting surprises. And one measure of how good a company is, is what percent of the surprises are good versus bad. So when we were going through our adolescence, our growing pains, 9 out of 10 surprises were bad. Every day was a surprise. It was never a good surprise. I remember saying at one point, like, “why don’t I get good surprises?”

SAFIAN: “Another bomb landed today.” 

Exploring corporate adolescence

CHESKY: Yeah, and the surprises are basically just like, you’re reacting, you’re on defense. Things are happening to you, versus you doing things. And once you’re in rhythm and you’re on top of things and you’re rowing in the same direction, then suddenly most of the surprises are good. Somebody’s like, “hey, guess what? We’ve been working on this thing” and I’m like, “I didn’t even know you were working on a thing.” “Yeah, and like we were onto something” and you’re like, “oh my god, this is going to change everything” and that happens all the time now. 

And that’s what happens when you cross corporate adolescence. And when you started interviewing me, I was in adolescence. And unfortunately, our corporate adolescence was about as awkward as my real adolescence. It was very awkward, very painful. And I think that like a lot of companies, they’ll go through adolescence and that adolescence is like I can describe it like, so you have an idea. And you get to product market fit. That’s like you enter childhood. It’s like really fun. Everything’s wonderful. You’re like a hot company. You get interviewed by Bob and you think you’re the man. And that’s like the wonderful childhood. 

And then of course you enter adolescence. Yeah, you’re successful. But now you’re having trouble managing executive team, costs are rising, growth is slowing. You’re having trouble pivoting to the next thing.

Most of us, we all started as good founders. You don’t really have to learn to be a good founder. You just become a founder. And if you’re super determined and creative and resilient, you can be a good founder. But no one’s born being a good CEO. And I don’t think anyone ever started as a good CEO. So at one point, you go from being like a world class founder to a pretty crappy CEO. And almost nobody has ever gone from world class founder to world class CEO without having first been a crappy CEO because it’s just like a totally different job. And that’s what I would describe as corporate adolescence. It’s a painful period. And unlike adulthood, most people make it out of adolescence. Most companies probably don’t actually make it out of that awkward adolescence. But if you can get to the other side and I think like, my series of podcasts with you, I think was the journey from crisis, to like recovery to kind of growing up. On the other side of that is like the most creative you can ever imagine. 

I’ve had a number of people I’ve looked up to. But like, you know, in the last 25 years, the one I would’ve looked up to by far would be Steve Jobs. And what I liked about him was he had that moment of truth from 1997 to maybe 2000/2001.

SAFIAN: Yeah he certainly grew up as a leader.

CHESKY: People should recall he came back to Apple and I don’t think anyone would have described him as a good CEO. Do people think he was a good CEO at NeXT? I don’t know. But I think a lot of people would say that he learned to go through the adolescence at NeXT. He learned to become a CEO. And then by the time the iPod launched, he had a 10 year run from 2001 till 2011, when he passed that was a run unlike we’ve ever seen in this industry, hit after hit after hit after hit. And it was like this creative momentum. And it was like the company remained a startup. 

And I’ve always dreamed of being able to have an era like that. And I don’t want to say we’re for sure entering that period. But I do feel like the next 10 years, there’s a real chance that we could have our own version of, at least having what I think we can do is in our future we will have a whole bunch of new things coming out. And I spent 15 years trying to perfect this one thing. It’s worked out pretty well. It was a pretty good idea that my friends and I had in my mid-twenties but now we’re ready to then do the next thing. 

SAFIAN: I don’t know how much, do we have more time?

CHESKY: I can keep going. If we did this for 12 hours, on hour 12, I’d have more energy than right now. 

SAFIAN: Brian is indeed just getting started. It’s like our conversation is business-therapy for him, talking about his dreams, addressing his challenges, honing his strategic plans by talking through them. Yes, there is a Part 2 of my chat with Brian, and it will release on Friday, available only through the new Rapid Response feed. So please subscribe on Apple, Spotify, wherever you get your podcasts. As we continue on, Brian’s filter keeps receding. We talk about how he’s partnering with legendary Apple designer Jony Ive, what ChatGPT gets all wrong that people are missing, and how he personally orchestrates the inner workings of Airbnb. It’s part confessional, part braggadocio, and totally absorbing. I hope you’ll join us. I’m Bob Safian. Thanks for listening.