Airbnb reimagined (Part 1), w/CEO Brian Chesky

Primary Topic

This episode delves into Airbnb's innovative initiatives under CEO Brian Chesky, exploring new frontiers beyond traditional lodging.

Episode Summary

In this episode of "Masters of Scale," host Bob Safian interviews Airbnb CEO Brian Chesky about the company's shift towards creating unique experiences with iconic stays, like the Barbie Malibu Dream House, and their ventures into AI integration. Chesky shares insights from Airbnb's recent earnings and discusses his partnership with Apple's Jony Ive. The episode also covers Chesky's perspectives on the benefits and challenges of Airbnb being a public company. Additionally, Chesky discusses personal anecdotes about his journey from a bodybuilder to a CEO, revealing how physical discipline shaped his business acumen.

Main Takeaways

  1. Airbnb is expanding its offerings to include not just homes but immersive experiences with iconic stays.
  2. The company is exploring AI to enhance user interactions and streamline operations.
  3. Brian Chesky finds unexpected joy in earnings calls, appreciating the discipline they bring to his role as CEO.
  4. Chesky discusses the personal impact of leading a major company, highlighting the importance of mental and physical health.
  5. The episode reveals Airbnb's strategic shift to maintain relevance and top-of-mind presence in the competitive travel market.

Episode Chapters

1: Introduction

Bob Safian introduces the episode and the guest, Brian Chesky, discussing the context of Airbnb's evolution and current endeavors. The chapter sets the stage for a deep dive into Airbnb's new strategies. Bob Safian: "That's Brian Chesky, co-founder and CEO of Airbnb, who's about to take us into a deep, revealing look into the Airbnb of today and of tomorrow."

2: New Directions at Airbnb

Chesky talks about recent initiatives and the collaboration with Jony Ive, emphasizing Airbnb's push into creating memorable stays and experiences. Brian Chesky: "Airbnb going beyond homes and truly entering this new creative place."

3: The Role of a Public Company CEO

Chesky reflects on his experience with Airbnb's public status, discussing both the challenges and unexpected benefits of being a publicly traded entity. Brian Chesky: "I actually kind of weirdly enjoy earnings calls."

4: Iconic Stays and Brand Expansion

This chapter focuses on Airbnb's strategic marketing through iconic stays, enhancing brand awareness and tapping into new market segments. Brian Chesky: "From X-Men mansion to Ferrari Museum to Princess Purple rain house."

5: Personal Insights and Leadership

Chesky shares personal stories from his life, drawing parallels between his experiences as a bodybuilder and his leadership at Airbnb. Brian Chesky: "If you can change your body, you can change your life."

Actionable Advice

  1. Embrace changes and use them to fuel personal and professional growth.
  2. Integrate technology wisely to enhance business operations and customer experiences.
  3. Maintain physical and mental health to manage the stresses of leadership.
  4. Cultivate strong relationships both personally and professionally to support your endeavors.
  5. Keep innovating to stay relevant in a rapidly changing industry.

About This Episode

As Rapid Response begins a twice-weekly cadence, Airbnb co-founder and CEO Brian Chesky returns to reveal how the company’s new Icons initiative points toward a surprising new chapter ahead. Host Bob Safian gets Chesky to open up about the mental struggles of being a high-profile CEO, plus the inside story behind Airbnb’s recent ad campaign targeting hotels. The pair cover so much, we’ve split the episode into two parts. Part 2 drops this Friday exclusively in the Rapid Response podcast feed. Make sure to subscribe so you don’t miss out!

People

Brian Chesky

Companies

Airbnb

Books

None

Guest Name(s):

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Content Warnings:

None

Transcript

Bob Safian
Hi, it's Bob Safian. You've been hearing me as the host of rapid response in this feed for a few years now with short, newsy interviews alongside the deeper dives of masters of scale. Well, I'm excited to share that rapid response is expanding into its own feed. We'll be putting out shows twice a week, focusing on the urgent issues that business leaders are dealing with in real time. So search for rapid response in your podcast player and subscribe to make sure you get all our episodes.

I'll see you on the other side. The pandemic, you know, hit. People were predicting, this is the end of Airbnb. Is Airbnb gonna exist? And so my darkest moment.

Brian Chesky
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, this is 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's 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 Airbnbs new initiatives 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 hes 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 two 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.

Erika Flynn
Hi listeners, it's Erika Flynn, VP of alliances in audience development at. Wait, what? The company behind masters of scale. My day to day consists of nonstop communication, not only with my immediate team, but with our current partner relationships and with incoming leads from possible future partners. Which is why I rely on the ease of Grammarly to keep my communication clear and efficient.

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Join me and over 70,000 teams who trust Grammarly to work faster, hit their goals, and keep their data secure. Visit Grammarly.com to learn more. That's Grammarly.com dot 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. It's good to be here with you as well.

Brian Chesky
I'm excited to be back. So first of all, welcome to New York, or welcome back to New York. I know you grew up, you grew up in New York, upstate New York. Yeah. You've had a busy month.

Bob Safian
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 at this point? I stay with my sister apart. Yeah, I stay in my sister's apartment in Tribeca.

Brian Chesky
The whole original premise of Airbnb was the experience of staying with a close friend in the city. Well, when I have close friends, if they're willing to still have me, then I'll still do that too. Yeah, sister counts in that regard. Sister counts. She's one of my closest friends.

Bob Safian
Now, I have to say, you're here in New York for earnings. Earnings cannot be the most fun part of this job. It's definitely, 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 CEO's never go public.

Brian Chesky
Stay private as long as you can. And I had like, and so therefore, 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 CEO's. A lot of people said, you particularly will not like being a public company CEO. And I'm like, why me particularly?

Maybe it had something to do with me being a designer, having gone to RISD and like, 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 earnings 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 audited financials, 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 when you're a private company and you're really big, there's always a sense that you're like 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 super fair. I do think the market is like, I'm never going to figure out the markets, but it's not that bad as you're talking.

Bob Safian
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 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. Well, the good thing for you, I tend to be an oversharer, and that might not be what my team, but I think for you and everyone else that works. So last summer you launched this Barbie Malibu BTS. That kind of went crazy when the movie went crazy nuts, right? And now you've announced eleven icon locations, right?

From X Men mansion to Ferrari Museum to Princess Purple rain house. 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 100%. So basically the quick version of story, just to give some more background icons is ten years ago, I remember I was with my co founder roommate.

Brian Chesky
So 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 you would have gone. We get to an Ikea, we're walking down the hallway, and we see a bedroom, like, you know, those Ikea, like, showroom bedrooms. I remember saying to him, like, wouldn't it be funny if we put this on Airbnb? It would, like, as a joke.

And we started, like, talking about it internally, like a joke. Like, we're going to, like, list a night at the Ikea. Well, somebody in our australian team, unbeknownst to me, hears about this idea and reaches out to, like, some marketing executive in IKea. And they one day tell me, like, hey, we got the IKea, this Ikea, in, like, 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? I remember this. I'm like, I didn't think there were any more blockbusters. And she's like, actually, it turns out there's one left in Bend, Oregon.

So we put on Airbnb. It went all over the Internet. It got thousands of press articles, probably got millions and millions of dollars with the press. So then last year, the Barbie movie's coming out. I think it was Mattel and Warner brothers that reached out to us and they said, could we do a promotion with Barbie?

Cause they were gonna do a bunch of these 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 as if it was a Barbie Malibu dream house. That is your way to the last detail.

To the last detail. As Charles Eames said, the details aren't the details. They make the design. And Walt Disney would look at 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. So anyways, this Barbie house we put on Airbnb, it gets more pressed than the IPO, and we're like, what the hell? The universe is telling me that the world wants this? So there's not necessarily a strategy behind it. There's just a feeling that there's an opportunity.

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 gotta 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. It was 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. So we huddled together. And probably my favorite concept that the team came up with is the up house and the up house. The up house was one of my favorite movies. And I said, if we're going to build this uphouse, you better make sure, like, it is down to the last detail.

Because people have been to Disneyland and their expectation is that 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 their graphic design. It's that level of detail. So we do that.

We design this house. It takes like 100 people to do. We assemble like fabricators, like prop designers. We had to assemble like a team of 100 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. No, they're supported by the ground. And so if you lift a house, it collapses.

There's no structural integrity. So we ended up working with structural like engineers to figure out how can you construct a house that's 40,000 pounds? Okay, 40,000 pounds that can be lifted 50ft in the air, 50ft five stories in the air and above it we'll have 8000 balloons. Now, you can't be helium balloons. Obviously, the physics doesn't actually work out that you'd need like the biggest helium balloons in the world.

And if they deflate you, 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 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 house can withstand before the rocking becomes dangerous and the props basically just dismantle. We found land in New Mexico where they filmed Oppenheimer, and that's basically. 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, eleven of them. Given the response of Barbie, I knew if we put out icons number one, we remain top of mind. Now, everyone knows Airbnb, but, like, our competitors spend four or $5 billion a year on, like, 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 travel.

So you have to remain top of mind. The second thing is, like, we're in every country in the world, with only a few exceptions, but, like, 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's pretty amazing.

Like, it's a noun and a verb. It's one of only brands that is like Xerox or Kleenex. Right. It's like it means something. The problem is it's a noun, 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? Right. It becomes narrow. 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. Yeah. I mean, as you're talking about the uphouse, clearly it costs you a lot of money. It was expensive.

Bob Safian
And when I think about the other things that you and I have talked about, pandemic and ipo and whatever, eleven listings on a service the size of Airbnb can seem kind of modest. Why spend all that money on just that? But as you're talking about it, this is a strategic decision, investment in brand and awareness and sort of the reputation and perception of what Airbnb is and could be. There's two things. Number one, while we don't spend nearly as much as our competitors in marketing, so, like, travel is just to back up.

Brian Chesky
So travel is an industry where people spend a lot of marketing. Our competitors, like some of the biggest OTA, spend almost 40% of their revenue on marketing. So it's like, that's a lot. It's a very marketing driven industry. We spend 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 on Instagram or TikTok or Snap, how does this perform? And our theory is this will be some of the best Roi that we'll ever do for marketing.

So that's kind of number one because. You get so much earned media. Basically everyone. 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 brings me back to Walt Disney.

Before Walt Disney built Disneyland, he built a, like, small train set in his backyard. And no one can understand, like, why a guy that had this huge Hollywood studio, he was like, one of the famous people in the world is like, spending all his time on this little train set. He had Salvador or Dali come to this train 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. I mean, they're like, they're Disney like experiences, right? You're not going into the theme park business, or are you thinking about, like, how do you do theme park business in an Airbnb way? Yeah, it's a little bit like, I think you could think of it as like, we launched experiences, like, a long time ago. It got some traction, never really captured the public's imagination like a 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 4000 tickets a year, so clearly these would be sold out and they're going to be a low price.

And we'll start with 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 going to start very high end with icons and then we're moving to mass. It won't be a theme park. I think it's going to reinvent the company and it's going to be the beginning of the next chapter of Airbnb and we're going to launch it next year. Next year, next year.

Bob Safian
Oh, I can't wait to be back here again. I can't wait to tell you about. 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. So I'll confess that when I first heard about Airbnb's icons initiatives, 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. And 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 hints to share about that. After the break, we'll dig into the head to head ad campaign he's launched against hotel, the obsession about his biceps and his bodybuilding regimen, and more. Stay with us.

Jodine Dorset
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Bob Safian
Heard Airbnb's Brian Chesky talk about why he's invested heavily in creating just eleven low revenue stays called icons. Now we talk about how he's recently gone on the offensive to compete against big hotels, 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.

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? Because 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. Yeah, let me talk to you about that campaign. So first of all, for like the last ten or twelve years, we've been the receiving end of a lot of contrast of Airbnb versus like hotels. It's possible there's been billions of dollars spent and that we've been on the receiving end on the last decade or dozen years. Most team that I have today on the marketing and creative side was actually at Apple and shiat day during the golden age of Apple, I hired someone named Hiroki Asai.

Brian Chesky
He was the creative director at Apple. He brought in these two great creative directors, Scott Trottner, Eric Rumbaum. Turns out Scott Tratner and Eric Rumbaum 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 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. You know, 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 those family trips and those group trips you do in 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 end 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 totally destroying them.

That became the genesis of this campaign. And it's been just, the punchline is it's been the highest performing campaign we've ever done. It's, you know, I think great marketing is education. You're educating people about some indisputable truth. It is an indisputable truth that, like, 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 of yourself.

Those are just indisputable troops. You can't argue with them whether you want those or not. Separate. So when icons was announced, there was nearly as much social coverage of your biceps as of the house.

I wasn't expecting that. I've had these biceps the whole time. Yeah. For some reason, people notice them. I know you and I haven't talked about this before, but I understand you did bodybuilding when you were younger.

When I was 19, I was a competitive bodybuilder, yeah. So what's your routine like? Is it like, is it an outlet for you, for frustration? Is it like meditation? It's all the above.

But I started bodybuilding when I was 1617 years old. So I kind of joke I wasn't a tech founder that 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 100, 2125 pounds. I was just super skinny. I remember there was a program and I was listed 135 pounds.

All the other players are like 180 pounds. So I started weightlifting, and I remember telling my friends when I was 17, they were kind of 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 7th most muscular teenager in the country. I competed in what basically the teenage mister America was 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. Even like a lot of therapists, they might say, start with your body.

It's like trying to start with your thoughts, 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 somebody has this flash of insight, and anyone who's done this knows it's not one idea, it's 100,000 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. The amount of stress can drive you crazy, and it's driven a lot of people crazy. And I think, 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 have 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. You have a lot of energy and a lot of passion. And I know from your team that you're always going. Always. 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?

Bob Safian
Like the next thing? 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, you know, that could either sound inspiring or, like, a lunatic. You're a lunatic sound.

Yeah. But 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. Like, the part I like is the climbing. And so, like, I don't do all this for the result. I do it for the process.

Brian Chesky
And so I'm a little bit of a lunatic, but I also, 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 of. It's not a bad thing. It's not a bad thing to have a little gratitude. And I enjoy those moments. 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 an AI? And, like, someone's ahead of us. So all of us in Silicon Valley, like, that one person in Silicon Valley, 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 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 y'all gotta, like, we gotta be connected to, like, 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 five years or ten years, that's a little bit of an issue.

Potentially, you may be possibly disconnected from your roots in your past. And the other thing, I'll just say, like, being a CEO, like, can be, like, such a fun and rewarding job. It can also, if you're not careful, be, like, at times, a little bit close. Like, to an inescapable nightmare you can never escape. And the difference is your team.

Like, 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 ten or 20 people. But, you know, that sounds completely counterpart. Because the canvas is so much bigger. The canvas so much bigger.

But also, I have such a great team, and it doesn't mean that I don't have to deal with, like, some of the nitty gritty, but, like, there's so many intelligent, competent people that can absorb so much complexity that I feel like today I can almost feel like Mickey Mouse and fantasia, you know? Like. Like you can, like. Like, in other words, it's fulfilling. You're like, we should do this.

And it happens. And when you don't have the team, the right team in place, and so 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, like, 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, nine out of ten 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? Another bomb landed today.

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 have, like, you're in rhythm and you're on top of things and you're rowing in the same direction, then suddenly most of surprises are good.

Someone'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 gonna 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. You know, and unfortunately, our corporate adolescence was about as awkward as my real adolescence. It was very awkward, very painful.

And I think that a lot of companies, they'll go through adolescence and that adolescence is like, I can describe it. So you have an idea and you get to product market fit. That's kind of like you enter childhood. It's 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 the wonderful childhood. And then, of course, you enter adolescence, 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 a world class founder to a pretty crappy CEO. 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 in that, that's what I would describe as corporate adolescence. And 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, like, awkward adolescence. But if you can get to the other side, and I think, like my series of podcasts for you, I think was the journey from crisis to recovery to kind of growing up on the other side of that is the most creative you can ever imagine. I've had a number of people I've looked up to, but in the last 25 years, the one I would have 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, he. Certainly grew up as a leader. 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 ten year run from 2001 till 2011. When he passed. That was a run unlike we've ever seen 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 like 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 ten years, there's a real chance that we could have our own version of like at least having. What I think we can do is I think we, in our future, we will have a whole bunch of new things coming out. And I spent 15 years like trying to perfect this one thing. It's worked out pretty well. It's a pretty good idea that my friends and I had in my mid twenties, but now we're ready to do the next thing.

Bob Safian
I don't know how much do we have more time? I can keep going. If we did this for 12 hours on hour twelve, I'd have more energy than right now.

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 two 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 chat GPT gets all wrong, that people are missing, and how he personally orchestrates the inner workings of Airbnb. Its part confessional, part braggadocio, and totally absorbing. I hope you'll join us. I'm Bob Safian. Thanks for listening.

Jeff Berman
Hi everyone, it's Jeff Berman, CEO of wait what? And co host of the Masters of Scale podcast. Like many of you, my to do list changes by the minute. Whether I'm working with partners or hashing out legal documents or brainstorming with our team, there is never a shortage of tasks that require attention and constant communication. Like Masters of Scale co host Reid Hoffman.

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Grammarly has 14 years of experience and a business model that never sells our data security has been a priority since day one and continues to be integral to Grammarly's values. Today, join me and over 70,000 teams who trust Grammarly to work faster, hit their goals, and keep their data secure. Visit Grammarly.com to learn more. That's Grammarly.com dot rapid response is a wait. What?

Bob Safian
Original I'm Bob Safian. Our executive producer is Eve Tro. Our producer is Alex Morris. Assistant producer is Masha Makutonina. Mixing and mastering by Aaron Bastanelli theme music by Ryan Holiday our head of podcast is lital Milad.

For more, visit rapidresponseshow.com.