Hello.

How are you doing?

Thank you for having us.

We're going to be hosting Sophie.

Sophie, come.

She'll be co-hosting with us today.

She's such a good host.

And this is your house.

This is my house.

Love it.

Yeah, here we are.

This is the infamous Airbnb of all Airbnbs.

This is.

This is where it all happens.

I love your coffee table book game.

I'm, like, really into coffee table books.

Oh, yeah.

It's cool, right?

Yours are pretty good.

There's a lot of, like, cool design books here and, like, a lot of memorabilia.

Like, there's Obama O's.

This is literally how we funded the company.

We sold collectible breakfast cereal.

And you became cereal entrepreneurs.

Yes.

I think I've heard you say that.

You'll see that one's autographed by the actual President Obama.

Oh, wow.

And you handmade these, right?

We handmade these.

We designed these with a team.

And I literally hot glued this one myself.

Joe made me this one.

This is my IPO gift.

This would be my kid's favorite.

Chesky's charms.

Chesky's charms.

Chesky's chips.

Chesky's charms.

I love this house.

It's beautiful, honestly.

It's gorgeous.

And it's a nice balance because, you know, I live alone.

I don't want, like, a, you know, weird tech McMansion.

You know, the big super modern.

I'm not going to name names.

But, you know, people my age buying $100 million homes.

Yeah, yeah, yeah.

Not my thing.

What's it been like playing host so far?

Oh, my God.

It's been a lot of fun.

I'm a co-host.

I got Sophie Supernova.

That's true.

She's a nearly one-year-old, two-year-old golden retriever.

It's been cool because I haven't really hosted that much since the early days.

You're kind of busy.

You're running a multi-billion dollar company.

Like, what made you want to make time for this?

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.

People aren't just numbers.

They're people.

And that means that you need to be emotionally connected to what you're doing.

I understand when hosts are complaining about something or your customer is 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.

It was crazy to think you were going to rent your house to a stranger or that you were going to stay in some stranger's house.

And now it's just what we do.

Yeah.

Does the level of human openness to that idea still surprise you?

I think I'm less a visionary than an expeditionary in the sense that I didn't have a vision.

I discovered something.

One weekend I couldn't pay rent.

I decided to let people in my house only to make money for the most part.

I thought it would be fun.

And I ended up becoming friends with these people.

And it made me realize that, like, these homes are these private spaces that 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.

I think we have trouble imagining sociological changes, sometimes harder than technological changes.

We can all imagine things getting bigger, faster.

But it's hard to imagine us changing behavior.

But Airbnb has actually been a big part of, like, maybe a major sociological change.

Probably.

I mean, it's been now been used 1.4 billion times.

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 staying together.

People from the Middle East and Texas.

Like, cultures you wouldn't necessarily think mixing together.

I think we all would have said you were crazy.

It's like most tech companies have to understand laws of physics.

We call these first principles.

And we also have to know a different law, which is a law of human nature.

Like, who are we at a very basic level?

And if you can start to understand that, then you can start to design for people.

You know, obviously, the pandemic hits.

Travel comes to a screeching halt.

The majority of your revenue almost vanishes.

Also, nobody wants to see other people.

Right.

In that moment, did it feel like you were standing on the edge of a cliff?

I 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.

That's more than Starbucks.

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, I'd be like, you're totally crazy.

I thought we're making it.

We're working on IPO.

To then lose 80% of it in eight weeks?

I mean, you remember there were articles like, is this the end of Airbnb?

Will Airbnb exist?

I got to tell you, like, that changed my life.

And it changed my life and the company for the better. You ever hear people say, 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 from a business perspective.

How did you change as a person?

We'll see.

My hair is a little grayer.

But I think I really grew up during the pandemic.

I think I felt my responsibility more.

Employees worried about their jobs.

Investors 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 in 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 going to forget them.

What are the lessons?

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 wanted to run the company.

Because you hire people, and they come from Google, Apple, Microsoft, Amazon, and they bring their way with them.

And what I realized I was doing was trying to find some midpoint between how I wanted to run the company and how they wanted to run the company, which actually made everyone miserable.

It's like I had to go into wartime mode.

And the crazy thing was, as I took more command, more control, became more decisive, more bossy, so to speak, I think people were happier because they had clarity and direction.

And then the tide turned, or maybe it's like the Titanic didn't hit the iceberg.

You go public, Airbnb goes public.

It's the end of 2020.

I'm interviewing you live.

You can't even speak.

Like, you're completely tongue-tied.

I actually want you to watch it.

It's such a moment.

We just got indication on your opening price.

Shares indicated to open right now at $139 a share, which is more than double what you priced at.

I mean, are you at all concerned about froth?

What do you think about that number and the potential that you're leaving billions of dollars on the table?

That's the first time I've heard that number.

In April, we raised money, and it was a debt financing. That price would have priced us around $30.

So I don't know what else to say.

Wow.

I haven't watched that in a long time.

Wow.

That actually makes me a little emotional.

What's going through your head in that moment?

I think that moment, it was like my hard drive 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 going to be a 24-hour thing.

And I probably never stopped at any point to think of anything.

You took a whole year, and you made it like a 15-second trailer.

And I was like, oh, my God.

And maybe at that moment, it all hit me.

This is just so crazy.

Your interview went viral.

It did.

People could see it hit you.

Yeah, yeah, yeah.

My eyebrows went to the top of my head.

And I didn't know they went that high.

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.

Did you ever think about where Airbnb would be if the pandemic didn't happen?

That's the crazy thing.

Like, your culture is often forged in your darkest moments.

I think people think of culture as, like, you know, the perks, 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 forge you.

We basically made, like, five years of progress in, like, six months.

And you can't ask for an occasion like that.

You can only hope that if it happens, you will rise.

We've seen a lot of founder-CEOs step back, whether it's Amazon, Google, Twitter, Pinterest, Slack.

You're still here.

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.

The job today as a public company CEO is more fun than the job as a private company CEO.

I feel like I often hear the opposite.

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 ended up generating $3.5 billion in free cash flow.

There's a paradox there.

I like to tell entrepreneurs, I think of the growth of your company.

You have to grow faster than that.

And if you don't grow faster in your company, then your company is going to be pulling you.

And then you're going to eventually be holding it back.

Does it ever feel like this immense responsibility that you have to stay, or does it feel like a burden?

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, 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 is 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 generate profit and be a real company.

Phase four, reinvent yourself.

Extensively, I'm an entrepreneur and a business person, but I think of myself as kind of designing and making.

And the reason I have more fun now is because now it's more creative than it used to be.

Are you an artist, designer first and CEO second?

Is that what you would say?

I think you're always what you were growing up.

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.

And how does that change the company?

How is that mentality infused into the company?