Airbnb CEO: “Airbnb Was Worth $100 BILLION & I Was Lonely & Deeply Sad!”

Airbnb CEO: “Airbnb Was Worth $100 BILLION & I Was Lonely & Deeply Sad!”

The Diary of a CEOOct 9, 20231h 37m

Brian Chesky (guest), Steven Bartlett (host)

Childhood, identity, and using creativity as an escape and a way to belongIndustrial design as training for entrepreneurship and tech leadershipWork addiction, conditional love, and the emotional cost of successLoneliness of leadership and the importance of intentional relationshipsFounders vs. professional managers, creativity vs. data-driven incrementalismCOVID-19 crisis, layoffs, and how principles shape company cultureAirbnb’s future vision: from booking spaces to building global community and combating loneliness

In this episode of The Diary of a CEO, featuring Brian Chesky and Steven Bartlett, Airbnb CEO: “Airbnb Was Worth $100 BILLION & I Was Lonely & Deeply Sad!” explores airbnb’s Brian Chesky: Success, Loneliness, and Redesigning Human Connection Brian Chesky, co-founder and CEO of Airbnb, traces his journey from a sensitive, outsider child obsessed with drawing imaginary worlds to leading a $100B company and confronting deep loneliness at the top.

Airbnb’s Brian Chesky: Success, Loneliness, and Redesigning Human Connection

Brian Chesky, co-founder and CEO of Airbnb, traces his journey from a sensitive, outsider child obsessed with drawing imaginary worlds to leading a $100B company and confronting deep loneliness at the top.

He explains how his industrial design training shaped Airbnb’s product and culture, why creativity and first-principles thinking beat data-only decision-making, and how great companies are defined by crises like COVID-19.

Chesky reflects on work as an addiction that brought status but not love, the emotional toll and responsibility of laying off 25% of Airbnb during the pandemic, and the hollow realization that life felt the same after a blockbuster IPO.

Looking ahead, he wants to shift Airbnb from just homes and travel to a global community that combats loneliness by designing richer human connection, grounded in purpose, relationships, and intentionally designed culture.

Key Takeaways

Design your life and company from first principles, not inherited templates.

Chesky’s industrial design background taught him to consider an object end-to-end: materials, manufacturing, cost, audience, marketing. ...

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Start by obsessing over 100 people who love you, not a million who kind of like you.

Airbnb began as a way for three people to sleep on airbeds during a design conference, not a grand plan to host millions. ...

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Success will not heal your inner wounds; you must address them directly.

Chesky frames his work as an addiction that was rewarded because it was productive. ...

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Fight the default of isolation: relationships must be actively designed and maintained.

Chesky warns that entrepreneurship, by default, isolates you: employees become less like friends as the company grows, people assume you’re too busy to contact, and you respond only to inbound work. ...

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In crises, make principle-based decisions and treat people with dignity; that *is* your culture.

When COVID-19 wiped out 80% of Airbnb’s business in eight weeks, Chesky chose to treat the moment as the company’s defining test. ...

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Culture is built by daily behavior and leadership example, not by posters and slogans.

Chesky insists that culture is “the shared way you do things”—who you hire, fire, promote, and how leaders behave in real decisions. ...

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Aim to build a company that reinforces human connection in an increasingly lonely world.

Chesky wants to shift Airbnb’s center of gravity from “spaces” to “people,” with richer profiles, strong identity and trust layers, and the app acting like a “global host” that connects you to places, experiences, and other people. ...

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Notable Quotes

Don’t focus on the mountaintop. Focus on the first step.

Brian Chesky

What I wanted was love and what I was actually attracting was adulation. And adulation is like a cup with a hole at the bottom.

Brian Chesky

Bad companies are destroyed by a crisis. Good companies survive a crisis. But great companies are defined by a crisis.

Brian Chesky (quoting Andy Grove and applying it to Airbnb)

In the long run, the culture is the most important thing you will ever design because it’s the engine that designs everything else.

Brian Chesky

If your goal was to be public so you could say you’re a public-company CEO, you’ll find your life is pretty much exactly the same the day after the IPO.

Brian Chesky

Questions Answered in This Episode

You’ve described adulation as a ‘cup with a hole at the bottom.’ Practically, what daily habits or boundaries have you put in place now to keep from slipping back into chasing that feeling through work or public praise?

Brian Chesky, co-founder and CEO of Airbnb, traces his journey from a sensitive, outsider child obsessed with drawing imaginary worlds to leading a $100B company and confronting deep loneliness at the top.

Get the full analysis with uListen AI

When you restructured Airbnb to run like a startup again—flattening divisions and centralizing product decisions—what specific tradeoffs or internal resistance did you face, and what would you do differently if you had to implement that redesign a second time?

He explains how his industrial design training shaped Airbnb’s product and culture, why creativity and first-principles thinking beat data-only decision-making, and how great companies are defined by crises like COVID-19.

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During the COVID-19 collapse, were there any principle-based decisions you *almost* made differently because the numbers looked too scary—and, looking back, do you think sticking to principles ever cost Airbnb in ways you still wrestle with?

Chesky reflects on work as an addiction that brought status but not love, the emotional toll and responsibility of laying off 25% of Airbnb during the pandemic, and the hollow realization that life felt the same after a blockbuster IPO.

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You want Airbnb to help combat loneliness by acting like a ‘global host.’ What’s one concrete product feature or system you *won’t* build in pursuit of that goal because, although it might boost engagement, you believe it would ultimately make people feel more isolated?

Looking ahead, he wants to shift Airbnb from just homes and travel to a global community that combats loneliness by designing richer human connection, grounded in purpose, relationships, and intentionally designed culture.

Get the full analysis with uListen AI

Given your belief that founders bring qualities professional managers often can’t, how are you practically designing succession at Airbnb so that the company preserves its creativity and heart if, or when, you eventually step back?

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Transcript Preview

Brian Chesky

You lose 80% of your business in eight weeks, and I knew there were questions. Is this the end of Airbnb? Will Airbnb exist? Brian Chesky. Founder and CEO... Of the $100 billion company... Airbnb, one of the most successful and most disruptive companies in the world. Airbed-and-breakfast was just a way to keep paying rent before we came up with the big idea. We did not think airbed-and-breakfast would be a company where four million people a night would use. Don't focus on the mountaintop. Focus on the first step. A lot of breakthrough ideas don't seem breakthrough at the time, they seem crazy. People tend to overestimate what they can do in a year, and underestimate what they can do in 10 years. 10 years is a profoundly long period of time if you're disciplined and focused. And you can have a small idea, a small dream, and you can build something vast.

Steven Bartlett

Airbnb is gonna IPO. And then disaster strikes.

Brian Chesky

The Coronavirus... Emergency. Stay at home... Stay at home. You lose 80% of your business in eight weeks, and I knew there were questions. Is this the end of Airbnb? Will Airbnb exist? We had to make some incredibly difficult decisions. So I write this letter to the entire company. Here's what I said.

Steven Bartlett

Is it hard for you to read that?

Brian Chesky

Yeah. Yeah, no, now I get a little emotional reading that.

Steven Bartlett

Why? (instrumental music plays) Brian, I'm a firm believer that our external world can change and evolve and look different, but it tends to be the case that our internal world is much more stubborn, which is who we are at our core. And I also believe that who we are at our core is often shaped by our earliest experiences. That's been supported by a lot of the psychologists I've sat here with. To understand you, the way you think and who you are, I think it's best to first understand that early experience, and how it shaped the internal Brian that remains regardless of how everything else in your life has changed.

Brian Chesky

Well, yeah, thank you for having me on. I, um, I came from a pretty normal, nondescript background. But in parallel to sports and all the regular things kids had, I had this other interest. It was the thing that most defined me, and that was that I was an artist. I would be drawing and drawing, and I have these pads of paper. And I go through hundreds and hundreds of pages, almost compulsively drawing, um, both trying to learn how to mimic an environment and reproduce it in reality, and when I was, you know, 10, I could probably draw like an adult and by the time I was in high school, I could, you know, draw like, you know, probably akin to a professional artist. I love to design worlds. I wanted to design an escape. And at the age of 17, I, I decide I'm going to design school. So I've already taken like 100 opportunities in life, and now I'm like, "Okay, I'm gonna do this. I'm not gonna be like a politician, a doctor, a lawyer, a astronaut, I'm gonna be a d- some, an artist or a designer." Halfway through freshman year, they have to, they tell you to declare a major. What kind of artist and designer? I'm like, "I'm still 17. And I gotta tell you what type of artist and designer?" This guy comes in and he pitches an department called Industrial Design. It just sounded cool, Industrial Design. And I was like, "What is industrial design?" And I remember him saying something like, "Industrial design is the design of everything from a toothbrush to a spaceship, and everything in between." To design a physical object, you have to understand three dimensions. You can't just design an object, you have to understand how to make the object. If you were a graph designer, you didn't really have to know how to make anything. I guess you had to know how to print it. But you had to know manufacturing. What kind of materials is it? Are the materials sustainable? Where do you manufacture it? Well, how much is it gonna cost? Because h- like, how much it's gonna cost, like, has implications on how you design it. Well, how much it's gonna cost depends on who is the audience. How are you gonna market it? You see, when an architect designs a building, no one, like, blames the architect if the office building doesn't get leased out.

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