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Brian Chesky

👤 Person
1017 total appearances

Appearances Over Time

Podcast Appearances

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And they're like, wait, where are all these extra people gonna stay? That's how we launched. We launched the Democratic National Convention. We got like 80 bookings. I thought we were huge. And then next weekend for Senator McCain, we had two bookings, not as popular. And then the following week, no bookings. And I realized if only there were political conventions every week, we'd have a business.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we're now totally broke. We're like worse than broke. We're actually in debt. We don't know what to do. And our name is Airbed and Breakfast. And I'm like, the airbeds aren't selling. Maybe there's money in breakfast because not everyone sleeps on airbags, but everyone eats breakfast. And this is where even the next step of the connection to President Obama comes in.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we're now totally broke. We're like worse than broke. We're actually in debt. We don't know what to do. And our name is Airbed and Breakfast. And I'm like, the airbeds aren't selling. Maybe there's money in breakfast because not everyone sleeps on airbags, but everyone eats breakfast. And this is where even the next step of the connection to President Obama comes in.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we're now totally broke. We're like worse than broke. We're actually in debt. We don't know what to do. And our name is Airbed and Breakfast. And I'm like, the airbeds aren't selling. Maybe there's money in breakfast because not everyone sleeps on airbags, but everyone eats breakfast. And this is where even the next step of the connection to President Obama comes in.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

We came up with a Barack Obama themed cereal. Yeah, that's right. And it was this box. We were like, well, what would a box of Barack Obama cereal? It was so obvious. He had the iconic O, like Cheerios. Yes. We called it Obama O's, the breakfast of change. And then we said, well, we got to be nonpartisan.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

We came up with a Barack Obama themed cereal. Yeah, that's right. And it was this box. We were like, well, what would a box of Barack Obama cereal? It was so obvious. He had the iconic O, like Cheerios. Yes. We called it Obama O's, the breakfast of change. And then we said, well, we got to be nonpartisan.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

We came up with a Barack Obama themed cereal. Yeah, that's right. And it was this box. We were like, well, what would a box of Barack Obama cereal? It was so obvious. He had the iconic O, like Cheerios. Yes. We called it Obama O's, the breakfast of change. And then we said, well, we got to be nonpartisan.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we created Captain McCain's because he was a captain in the Navy, a maverick in every bite. So we make these cereal boxes. And that actually is how we funded the company. So the breakfast took off.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we created Captain McCain's because he was a captain in the Navy, a maverick in every bite. So we make these cereal boxes. And that actually is how we funded the company. So the breakfast took off.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

So we created Captain McCain's because he was a captain in the Navy, a maverick in every bite. So we make these cereal boxes. And that actually is how we funded the company. So the breakfast took off.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

You know what's funny? No one wanted the airbeds. They were like, I'm not staying at a stranger's house. That's crazy. I'm not sleeping on an airbed.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

You know what's funny? No one wanted the airbeds. They were like, I'm not staying at a stranger's house. That's crazy. I'm not sleeping on an airbed.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

You know what's funny? No one wanted the airbeds. They were like, I'm not staying at a stranger's house. That's crazy. I'm not sleeping on an airbed.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Well, funny enough, years later, President Obama said, yeah, I don't think we ever gave you permission for our likeness. And I was like, I was 26. Yeah.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Well, funny enough, years later, President Obama said, yeah, I don't think we ever gave you permission for our likeness. And I was like, I was 26. Yeah.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Well, funny enough, years later, President Obama said, yeah, I don't think we ever gave you permission for our likeness. And I was like, I was 26. Yeah.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

But we basically, I remember once I was pitching a producer about our website, like a TV producer. And I remember him saying, send me, he says, I can't take this call right now. And I said, can I send you an email? And he goes, I get like 800 emails a day. And I remember that in my mind, like these are producers, they get all these emails. And I said, you know what you don't get?

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

But we basically, I remember once I was pitching a producer about our website, like a TV producer. And I remember him saying, send me, he says, I can't take this call right now. And I said, can I send you an email? And he goes, I get like 800 emails a day. And I remember that in my mind, like these are producers, they get all these emails. And I said, you know what you don't get?

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

But we basically, I remember once I was pitching a producer about our website, like a TV producer. And I remember him saying, send me, he says, I can't take this call right now. And I said, can I send you an email? And he goes, I get like 800 emails a day. And I remember that in my mind, like these are producers, they get all these emails. And I said, you know what you don't get?

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

800 boxes of Obama O's a day. So I basically got a media list. Media lists are, I don't know if they still have them, but you can basically get the addresses of all the reporters, the mailing address. And we got a hundred boxes. We mailed them to these reporters. They had opened the boxes. They were like, what is this?