IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky
Wed, 21 May 2025
This week Airbnb’s co-founder and CEO, Brian Chesky, joins Michelle and Craig at the table to discuss everything from boosting a business out of the startup phase to dating in search of deep connection. Brian shares stories about Airbnb’s early keys to success (hint: it has to do with breakfast cereal), the evolving responsibility of tech companies in the modern age and how young entrepreneurs can navigate the current tech landscape. Plus, Michelle presses Brian on the dating advice he received from a surprising source during the pandemic. Have a question you want answered? Write to us at imopod.com.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Chapter 1: How did Airbnb begin?
Thank you.
Thank you. Thank you for having me.
Welcome to IMO.
Yes.
I know, I know. I usually don't get to talk to you in an interview format. So let's pretend like it's just us at dinner somewhere with me poking you and prodding you on how life is. But I do want to hear about you as a host.
Yeah.
I mean, do you open up your home often? Yeah. Is this a regular thing that you do?
Yeah, guests come and they can book on Airbnb and-
Do they know it's you?
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Chapter 2: What unique challenges did Airbnb face at the start?
Would tell us about Chesky's chips.
Yeah, these are chashu cookies. They've been in the family, old family recipe I got off Google two years ago.
Well, why haven't you made us Chesky's chips?
Well, you know, you can book on Airbnb. Oh, man, I got to go. Okay. And then like Sophie, my golden retriever, may jump in bed with you. So if you're okay with dogs, leave the door open. She'll get in there. And I actually love hosting. My roommate and I were the first host on Airbnb. And there's something wonderful about opening your home to the world.
What's the weirdest guest that you've had? Can you say without insulting anybody? Or is everybody just really nice? Are they on their best behavior?
Everyone is absolutely on their best behavior, but... One guest did tell me that they wanted to stay with me so bad. I only found this out after they stayed with me, that they were reloading my page like thousands of times.
Oh my God.
And I thought to myself- I don't think it's a good sign, but maybe a little bit much. But he turned out to be an amazing person. Like concert tickets, right? Yeah, like reload, reload. And I'm like, these chips are not worth it. I got to be honest with you. They're pretty average bacon. That's great.
Yeah, but I have to say, Brian, if I'm a single girl out there and I find out that Brian Chesky is...
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Chapter 3: What role does social media play in our lives?
It was actually probably at RISD. The school was like very much like self-directed. You would like, I mean, first of all, like artists are all entrepreneurs, basically. I mean, they're sole proprietors, but you don't really work for somebody. There was this great quote at RISD. Art is a question of the problem of the world and design is the answer.
I started in art because I wanted to ask interesting questions about the world. And I kind of moved to design because I thought I really want to help people and try to design answers. And I thought to myself... I think this is for me. Like I kind of knew. And funny enough, my mom said, you got to get a real job one day. And I said, what's a real job?
Explain that.
She's like, a real job is one that has health insurance. That sounds like a parent. That sounds like our mom. So I ended up getting a real job of health insurance in Los Angeles. I'm like a designer. We have all these like little clients. Like my first project was like designing a toilet seat. So you got to start somewhere.
Yeah, yeah.
And then one day, you know, when I quit my job, I remember going home for Christmas and one of our family members asked, what are you doing? And I remember telling them, oh, I'm an entrepreneur. And I could hear my mom cross the room saying, he's actually unemployed.
It's like, thanks, mom.
And that's what I realized. When you're starting, it's mostly in your head until you manifest it and you make it real.
So now you've got... You got this place now, Airbnb, which I have gone from being a hotel guy to an Airbnb guy, just so you know. Tell us what's new, what's going on at Airbnb these days.
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Chapter 4: How does technology impact human connection?
So I was telling Mish, I got a chance last night to experience the services part. A chef... came to the Airbnb that we were at and we had this wonderful six-course meal with a French chef and his sous chef. And he made... a wonderful meal that was capped off with my favorite dessert because my birthday's coming up. And it was a lemon meringue pie made with lemons that he grew in his own garden.
So I've had a little taste of this and I was blown away.
I think there's this whole world just waiting for people. And imagine you can hit a button.
Yeah.
Chapter 5: What makes Brian Chesky's leadership style different?
And you can get anything you want in your life. And we vet everyone. And I think there's millions of people that can participate in this.
Now that we've launched this podcast, we've been getting some great questions from listeners. And a listener who just ironically named Brian has a question. And we now have our listeners ask the actual question. So let's take a listen to Brian's question. How do you think social media can play a constructive role in society?
And do you think we are spending way too much time online? There was a great saying at Apple in the 1980s when they developed the Macintosh. They said, never trust a computer you can't throw out the window. In fact, that's why they put a handle in the back of the computer. The reason why is they said a computer is a tool and it doesn't dominate us. We dominate it.
As long as we're in control of technology, then it's going to be wonderful. But when the technology starts to overtake our lives and be in control of us, it ceases to be a tool. And I think there's a real risk that social media has ceased to be a tool to connect us. And it's now a destination. And it can potentially be replacing real in-person connections.
I think that is potentially very dangerous. If social media is like a car... we're about to put a jet engine on the back of that car in the form of AI.
That's right.
Because what changed in the last 10 years, the 2030s are going to change so much more quickly. And the question becomes, should we be concerned or excited? And I guess it's in our hands. We have all the tools to solve all the problems that I could imagine us solving. We also have all the tools to further divide us. Now you do think,
a lot of the polarity and division and anger and resentment in the world, I think a lot of it comes from people feeling isolated, people feeling lonely, people feeling like they're falling behind, that the world's progressing without them. And I think we need to think these products as tools in service to us to make us happier, to make us more connected.
Brian, you speak differently, not just as an entrepreneur, but as a person in tech, sort of the Silicon Valley crew. Because one of the things that I worry about as a mother, as just a human being, is that it feels like we're moving away from connection. Yeah. So to hear you talk about what moves you, what moved you to start Airbnb, that it all starts with that connection. Why are you different?
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