Be a Different Kind of Leader with Brian Chesky

Summary

Podcast Summary: "Be a Different Kind of Leader with Brian Chesky"

Introduction

In this engaging episode of IMO with Michelle Obama and Craig Robinson, hosts Michelle and Craig welcome Brian Chesky, the co-founder and CEO of Airbnb. Released on May 21, 2025, the episode delves into Chesky's journey from a design student to leading a global community platform. The conversation spans topics such as entrepreneurship, the evolution of Airbnb, the impact of social media on society, the challenges of success, and advice for the next generation of leaders.

Brian Chesky’s Journey and the Birth of Airbnb

Brian Chesky shares the origin story of Airbnb, highlighting the serendipitous circumstances that led to its creation. In 2007, facing high rent in San Francisco and a sold-out design conference, Chesky and his roommate Joe Gebbia transformed their loft into a makeshift bed and breakfast, hosting three guests on air mattresses. This venture, humorously named "airbedandbreakfast.com," laid the foundation for what would become Airbnb.

“We end up having three people stay with us... these strangers came as strangers and left as friends.” [09:14]

Chesky recounts the challenges of launching the platform during the 2008 financial crisis, including the difficulty of balancing supply and demand. To keep Airbnb afloat, the duo innovated by creating Obama-themed cereal boxes, "Obama O's" and "Captain McCain's," which successfully funded the company’s early stages.

“And we think there's money in breakfast because not everyone sleeps on airbeds, but everyone eats breakfast.” [11:32]

Relationship with President Obama

A significant part of the conversation revolves around Chesky's relationship with former President Barack Obama. Michelle Obama notes the close bond they've developed over the years, with Chesky often seeking mentorship and advice from the former president.

“He’s the one who told me to reach back out to my old friends... Be more intentional.” [24:16]

Chesky emphasizes the profound impact Obama's guidance had on his leadership style, encouraging intention and responsibility in business decisions.

The Evolution of Airbnb: Beyond Accommodation

Chesky discusses Airbnb's expansion beyond just lodging, introducing "services and experiences." This initiative allows users to book not just stays but also services like personal chefs, masseuses, and more, aiming to enhance the platform's value and deepen user connections.

“What if you can Airbnb a chef to come to your house?... we have launched services and experiences.” [17:08]

Craig Robinson shares his positive experience with Airbnb's new services, highlighting the personal touch and quality they bring to user experiences.

Impact of Social Media and Technology on Society

A pivotal segment of the podcast addresses the role of social media and technology in modern life. Chesky expresses concerns about the overreliance on social media, likening it to a destination rather than a tool for connection.

“Social media has ceased to be a tool to connect us, and it's now a destination... it can potentially be replacing real in-person connections.” [19:53]

He warns against the dangers of technology overtaking human connections and emphasizes the importance of using tools intentionally to foster genuine relationships.

“We have all the tools to solve all the problems... they can become very dangerous.” [25:46]

Michelle Obama adds to this discourse, stressing that equity, equality, and justice must accompany technological advancements to ensure tools like social media serve the greater good.

Challenges of Success and Loneliness

Brian Chesky opens up about the personal struggles that accompany immense success. Despite achieving billionaire status at a young age, Chesky discusses the loneliness and isolation that often follow, contrasting his experiences with those of his middle-class friends who report higher levels of happiness.

“With success comes disconnection... I started realizing, ... the more success you get, the more isolated you get.” [26:48]

He credits President Obama for helping him navigate these feelings, encouraging a reconnection with friends and maintaining authentic relationships to combat loneliness.

Advice for Young Entrepreneurs and the Next Generation

Chesky offers heartfelt advice to young entrepreneurs facing economic instability and the daunting landscape of modern entrepreneurship. He encourages proactive mentorship seeking, rekindling old relationships, and embracing real-world experiences over digital interactions.

“One of the most important things you can do... rekindle old relationships... meet new people, it’s going to have a huge impact on your life.” [52:08]

Michelle Obama emphasizes the importance of purpose-driven work over mere financial gain, advocating for a broader mission that transcends profit.

“You have to think purposefully and intentionally about the use of that tool for young creators... it has to be something bigger than yourself.” [49:17]

Building a Human-Centric Technology Future

The conversation concludes with a shared vision for technology’s role in fostering human connections. Chesky underscores the responsibility of tech leaders to design tools that enhance societal well-being rather than contribute to division and isolation.

“We have to think about how to use technology to lift people up, to make sure that it helps parents, it helps young people...” [45:11]

Michelle and Craig echo this sentiment, advocating for intentional use of technology and balanced integration of digital and real-world interactions.

Closing Remarks

As the episode wraps up, Michelle praises Chesky for his openness and leadership, stressing the importance of maintaining humanity in technological advancements. Chesky humorously addresses his dating life, reinforcing the episode’s recurring theme of balancing personal connections with professional success.

“The real world is the real world.” [31:45]

Conclusion

This episode of IMO offers a deep dive into Brian Chesky’s entrepreneurial spirit, his thoughtful approach to technology, and his commitment to fostering genuine human connections. Through candid discussions and personal anecdotes, Chesky provides valuable insights into the challenges and responsibilities of modern leadership, making it a compelling listen for aspiring entrepreneurs and individuals interested in the intersection of technology and society.

Notable Quotes

• “If we could build a platform for trust, that people don't want to host strangers, but they'll host Mike or Marcia, who went to school here, and we could bring the humanity out of everyone.” [05:34]
• “It's a tool, but you can’t abuse it, and you can’t only use one tool.” [49:17]
• “The best success I've had with meeting people is the old fashioned way.” [46:34]
• “Being an athlete, you’ve been raised as a team player... that's why I take a more humanitarian look at technology.” [35:52]

Key Takeaways

1. Intentional Leadership: Leadership should be purposeful, focusing on societal impact over personal gain.
2. Human-Centric Technology: Technology should enhance human connections rather than replace them.
3. Overcoming Loneliness: Success can lead to isolation; maintaining authentic relationships is crucial.
4. Mentorship and Reconnection: Seeking mentors and rekindling old friendships are vital for personal and professional growth.
5. Purpose-Driven Entrepreneurship: Building businesses with a broader mission can lead to sustainable and meaningful success.

This episode serves as an inspiring guide for those looking to lead with empathy and integrity in the fast-evolving landscape of technology and business.

Transcript

[Michelle Obama]

You know, I have to say, Brian, if I'm a single girl out there and I find out that Brian Chesky is single, and I can, like, stay in his house.

[Craig Robinson]

Have you ever. You don't have to be feel pressured.

[Michelle Obama]

We've never talked about.

[Craig Robinson]

He just got here.

[Michelle Obama]

Have you ever.

[Brian Chesky]

Her and her husband have tried to set me up before, so, yeah, I'm.

[Michelle Obama]

Very invested in love life. Craig Robinson.

[Craig Robinson]

Hi.

[Michelle Obama]

How you doing, dude?

[Craig Robinson]

Good niche. How you doing?

[Michelle Obama]

I am good. You're looking. You.

[Craig Robinson]

I was gonna say you look refreshed.

[Michelle Obama]

Thank you. I am pretty refreshed. You look refreshed. You shouldn't be, because you still have little bitty kids.

[Craig Robinson]

I know.

[Michelle Obama]

I know. Not little bitty. I should stop calling them little bitty.

[Craig Robinson]

Yes.

[Michelle Obama]

They're not little bitty anymore, and they're almost as tall as me.

[Craig Robinson]

Yeah.

[Michelle Obama]

But, yeah, you're coaching, still doing all this stuff deep into the.

[Craig Robinson]

I'm still coaching and still parenting and all that kind of stuff. So I should look haggard. But I am always so excited to do this with you.

[Michelle Obama]

You sent or Kelly sent a picture. Austin's starting to drive.

[Craig Robinson]

Yes. Oh, this is a good story. So you remember the green car?

[Michelle Obama]

A green car that's like 100 years old?

[Craig Robinson]

It's a 1999 GMC.

[Michelle Obama]

You talk about an old man keeping a car forever.

[Craig Robinson]

Well, you know, I just. I'm my dad's kid. There's no need to get a new car when your old car is running perfectly well. We're finally getting rid of it.

[Michelle Obama]

Okay, Way to go. Yes, brah. Everyone, slow clap on that one.

[Craig Robinson]

We're finally getting rid of it. And the boys, Austin and Aaron, who are 15 and 13, heard about Avery and Leslie learning how to drive on that car, and they wanted to drive it before we got rid of it.

[Michelle Obama]

Oh, they're so sweet. They just really want to be a part of life. They always feel like they're missing out on something.

[Craig Robinson]

They feel like they came after all this stuff.

[Michelle Obama]

That's right. They did. And they kind of did. They kind of did.

[Craig Robinson]

They did. They did. We'll have to spend some time talking about the stuff they missed. Well, I'm excited. Cause today we have our first really sort of tech expert.

[Michelle Obama]

Yeah. Yeah. We're gonna be talking to Brian Chesky, who's a dear, dear friend. We will talk more about that. I love Brian. He and Barack have gotten close over the years, and he spent some time at our house. He's just a good dude. It's like if I had a Son. I would want my son to be Brian.

[Craig Robinson]

Oh, that's a huge compliment.

[Michelle Obama]

And we're gonna be talking a little bit about social media tech.

[Craig Robinson]

Loneliness.

[Michelle Obama]

Loneliness. So we got a lot on our plate, so let's not waste any time. Let's get Brian out here.

[Craig Robinson]

Well, let me give him a little bit of an okay.

[Brian Chesky]

Okay.

[Craig Robinson]

I know you know him, but our audience should hear a proper introduction. Brian Chesky is the co founder and chief executive officer of Airbnb.

[Brian Chesky]

And.

[Craig Robinson]

And in 2007, Brian became Airbnb's first host. But you know what's cool about.

[Michelle Obama]

See, I wanna hear about that. Cause I don't know.

[Craig Robinson]

Wait, listen, he's still a host.

[Michelle Obama]

I know. That's.

[Craig Robinson]

We will talk about that. We have to figure out how we can sign up for that. And since then, Brian has overseen Airbnb's growth to become a community of over 5 million hosts across 240 plus countries and regions. So without any further ado, welcome. Brian.

[Michelle Obama]

Brian.

[Craig Robinson]

Here he comes.

[Michelle Obama]

Hi, Brian.

[Craig Robinson]

Appreciate you.

[Brian Chesky]

Thank you. Thank you.

[Michelle Obama]

It's good to see you.

[Brian Chesky]

As always, thank you for having me.

[Michelle Obama]

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 at dinner somewhere with me poking you and prodding you on how life is. But I do wanna hear about you as a host. Yeah, I mean, do you open up your home often? Is this a regular thing that you do?

[Brian Chesky]

Yeah, they just come and they can book on Airbnb.

[Michelle Obama]

And do they know it's you?

[Brian Chesky]

Yeah, they definitely know it's me. And they do they have to pay more? It's actually free. It's a free. So it's kind of like if you kind of get lucky enough, you can stay with me. And I have some really cool people I've had stay with me and when they come and stay, stay, they stay. I have a two bedroom house. It's not a big house, so they stay in the guest room. And the first night I'll have a dinner made for them. I'm not much of a cook, but I am a little bit of a baker, so I make Chesky's chips.

[Michelle Obama]

Well, tell us about Chesky's chips.

[Brian Chesky]

Yeah, these are cha chu cookies. They've been in the family. Old family recipe I got off Google two years ago.

[Michelle Obama]

Well, why haven't you made us Chesky's chips?

[Brian Chesky]

Well, you know, you can book an Airbnb.

[Michelle Obama]

Oh, man, I gotta go stay in.

[Brian Chesky]

My guest room 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 just. I actually love hosting. You know, like, you know, I was. My roommate and I were the first host on Airbnb. And there's something wonderful about opening your home to the world.

[Michelle Obama]

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?

[Brian Chesky]

Everyone is absolutely 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.

[Michelle Obama]

Oh, my God.

[Brian Chesky]

And I thought to myself, this is. I don't think it's a good sign, but maybe. Maybe a little bit much. But it turned out to be an amazing person.

[Craig Robinson]

Like concert tickets, right?

[Brian Chesky]

Reload, reload. And I'm like, these chips are not worth it. I gotta be honest with you. Like, they're pretty average.

[Craig Robinson]

Baker, that's great.

[Brian Chesky]

Yeah.

[Michelle Obama]

But, you know, I have to say, Brian, if I'm a single girl out there and I find out that Brian Chesky is single, and I can, like, stay in his house.

[Craig Robinson]

Have you ever. Brian, you don't. You don't have to be feel pressured.

[Michelle Obama]

But we've never talked about.

[Craig Robinson]

He just got here.

[Michelle Obama]

Have you ever.

[Brian Chesky]

Her and her husband have tried to set me up before.

[Michelle Obama]

So, yeah, I'm very. I'm very invested in love life, but. So you've never met anybody that way, have you found. No.

[Brian Chesky]

No, I haven't. Most of the people have stayed are couples, actually.

[Michelle Obama]

Oh, that's.

[Brian Chesky]

Yeah, it's. It's.

[Craig Robinson]

But now you've given the whole world an idea. Gee whiz. Wait, so Barack has actually tried to fix you up?

[Brian Chesky]

Oh, yeah.

[Craig Robinson]

Is he any good at it?

[Brian Chesky]

We'll see, I guess. Oh, remains to be seen. But, yeah, no, he's. He's definitely very invested, and he's provided a lot of relationship advice to me, actually.

[Michelle Obama]

Well, we'll talk more about that. But just to help people get a sense of why you and why we have become so close. I mean, I don't know if most people know about how Airbnb got started, but you want to tell that story a little bit?

[Brian Chesky]

Yeah, I'll tell the. I'm from upstate New York. My parents are social workers. My mom once told me, growing up, like, I chose a job for the love, and I get paid no money, so you should make sure that you. You get a job that pays you a lot of money. And one day I said, mom, I want to be an artist. And she said, oh, my God, you picked the only job that's going to pay you less than a social worker. And I said, oh, I promise I'm going to get a real job. I ended up going to the Rhode Island School of Design.

[Craig Robinson]

Risd. Risd, yes.

[Brian Chesky]

In Providence. And we have a Providence connection.

[Craig Robinson]

We do. We do. I coached at Brown, for those of you who didn't know that. And RISD was right down the hill, and it was a wonderful place.

[Brian Chesky]

I love risd. I love Providence. It was such an amazing place because I always grew up thinking, like, you had to sit in class, sit still, like, follow the rules. And then at risd, they said, you're a designer. Everything around you was designed by someone else. You can design the world you want to live in. It made us very idealistic. I graduate risd, and I'm living actually here in Los Angeles. And my friend from risd, Joe, tells me, one day, brian, come to San Francisco. Let's start a company. I'm 25 years old, and my life is like, I'm in a car, and the road in front of me looks like the road behind me. That's the rest of my life if I stay on this track. And so I quit my job. I pack everything back of old Honda Civic, and I drive up to San Francisco. I get to San Francisco and Joe tells me, we have one problem. I said, what's that problem? He said, well, remember how I told you the rent is $1,000? Well, now it's been raised, and it's now $1,150. And I'm like, oh, I couldn't even afford the old rent check. It turns out that weekend, a design conference was coming to San Francisco. And we went on the conference website for this conference. All the hotels are sold out. And we had this idea. We said, what if we just turned our house into a bed and breakfast for design conference?

[Craig Robinson]

No way.

[Brian Chesky]

I didn't have any beds, though, because I just moved there. I didn't even bring a bed with me. Joe had three air mattresses in the closet. So we pulled the air beds out of the closet. We inflated them. We called it airbedandbreakfast.com and that's where the name Airbnb comes from.

[Michelle Obama]

And what year was that?

[Brian Chesky]

This is 2007.

[Michelle Obama]

2007.

[Brian Chesky]

And we end up having three people stay with us. Basically, what happened was we were able to pay our rent. But something I never expected happened, which is these three strangers came as strangers and they left as friends, which is not unsurprising. When somebody lives here for a week, you take them around the city. And Joe and I realize maybe there's a bigger idea here. I asked Joe, I said, who's the best engineer you know? He said, my old roommate. Natives. And this leads to how I got to know President Obama well before. But 2008, summer of 2008, we're trying to figure out how to launch Airbnb, and we got this chicken and egg problem they use in the marketplace. How do you get people to list their homes when there's no people traveling? How do you get people to travel when there's no homes? So we needed a big event. The biggest thing happening in the summer of 2008 was the election.

[Craig Robinson]

Oh.

[Brian Chesky]

And then Senator Obama was just nominated, as you remember. And I remember sitting at home with my roommate Joe, and there was, like, the CNN on tv, DNC housing crisis. They move him from the basketball arena to the football stadium. And they're like, wait, where are all these extra people gonna stay? That's how we launched. We launched at 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. So we're now totally broke. We're 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 airbeds, but everyone eats breakfast. And this is where even the next step of the connection to President Obama comes in. We came up with a Barack Obama themed cereal.

[Michelle Obama]

Yeah, that's right.

[Brian Chesky]

And it was this box. We were like, well, what would a Barack Obama.

[Craig Robinson]

I've seen that box.

[Brian Chesky]

What would a box of Barack Obama cereal. It was so obvious. He had the iconic O, like Cheerios.

[Craig Robinson]

Yes.

[Brian Chesky]

We called it Obama O's, the Breakfast of Change. And then we said, well, we got to be nonpartisan. 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.

[Michelle Obama]

Who are you selling these to?

[Brian Chesky]

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

[Michelle Obama]

See, now that makes sense.

[Brian Chesky]

That would be.

[Michelle Obama]

My reaction would be like, you know, you talk about this air mattress. I'm like, I don't know if I'm gonna rush to the air mattress. You should have called me. I would have told you that early on.

[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. Give me a break.

[Michelle Obama]

Minor details, minor details.

[Brian Chesky]

But we basically. I remember once a produ. 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, we don't get 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 could basically get the addresses of all the reporters. The mailing address. And we got 100 boxes. We mailed them to these reporters. They had opened the boxes. They were like, what is this? They put them on their desk in the newsroom. And then it spread all over the news. And that's how we funded the company. We had to joke. We were like serial entrepreneurs.

[Michelle Obama]

We sold enough cereal to fund the company. To fund the company.

[Craig Robinson]

Was there actual cereal in the boxes?

[Brian Chesky]

Where true artistic integrity mattered to me. So we actually had the exact cereal that was photographed on the box inside.

[Michelle Obama]

I didn't realize that that's how you funded the company. You sold that much cereal that you.

[Brian Chesky]

Got about $35,000 of cereal.

[Michelle Obama]

Wow. Wow. So it only took $35,000. You only needed $35,000 to get the company going?

[Brian Chesky]

Pretty much. And then 2009, we, like, joined this incubator called Y Combinator. We raised another 20,000. I mean, back then, that was like, a lot of money. Now now, like 26 year olds are raising, like $100 million for the AI companies. They have five employees. Back then, we were like, $20,000 is enough money to get us to ramen profitable. This was the thing. Ramen profitable means your company is profitable if everyone in the company only lives on ramen. And so that was our goal.

[Michelle Obama]

So the bar was. Bar was low.

[Brian Chesky]

We slept on air mattresses. You know, we lived the product. We only ate ramen, and eventually we got the company going. It was during the financial crisis 2009. People are losing their homes. Paul Graham, our first advisor and investor, said, make something people want. And we thought, what's better than making something people want? Making something they need. People need to make money because their home is about to get taken from them. And it happened during this new generation, the same generation that were the community mobilizers during President Obama's campaign. We were a new generation.

[Michelle Obama]

Yeah.

[Brian Chesky]

And we wanted to connect and travel different than our parents. And we wanted to, like, have a more authentic way of traveling. We wanted to live like a local. And so this feel totally new to us, even though it was weird to others.

[Michelle Obama]

Now, did you, did you come to the idea of Airbnb through your experiences? I mean, you're in design school. You're, you know, you're not a tech.

[Craig Robinson]

He's an artist.

[Michelle Obama]

You're an artist, you know, and you come from social workers.

[Brian Chesky]

Yes.

[Michelle Obama]

When did you get that spark that I'm gonna go into business? I mean, was it just something that continued to roll on? You were so far in once you got to San Francisco?

[Brian Chesky]

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 quota. Risd. Art is a question of the problem in 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?

[Michelle Obama]

Explain that.

[Brian Chesky]

She's like, a real job is one that has health insurance.

[Craig Robinson]

That sounds like our mom.

[Michelle Obama]

Yeah.

[Brian Chesky]

So I end up getting a real job of health insurance in Los Angeles. I'm like a designer. We have all these little clients. My first project was designing a toilet seat. So you gotta start somewhere.

[Michelle Obama]

Yeah, yeah.

[Brian Chesky]

And then one day 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 across the room saying, he's actually unemployed.

[Michelle Obama]

It's like, thanks, Mom.

[Brian Chesky]

That's What I realized when you're starting, it's mostly in your head until you manifest, it makes it real.

[Craig Robinson]

So now 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?

[Brian Chesky]

I'm so excited about this because I never thought we'd get to this point. You know, that very first weekend was about connection. It was about connecting with one another. And we always believe, if we could build a platform for trust, that people don't want to host strangers, but they'll host Mike or Marcia, who went to school here, and we could bring the humanity out of everyone. And we thought, you know, what if you can Airbnb more than an Airbnb? What if you can Airbnb a chef to come to your house? What if you can Airbnb a masseuse? What if you can Airbnb a makeup artist, a nail person, a personal trainer? And that's what we're doing. We've launched services and experiences, and I think this is just the beginning of the next chapter of Airbnb.

[Craig Robinson]

So I was telling me 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.

[Brian Chesky]

I think there's this whole world just waiting for people. And imagine you can hit a button 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.

[Craig Robinson]

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.

[Brian Chesky]

How do you think social media can play a constructive role in society?

[Craig Robinson]

And do you think we are spending.

[Brian Chesky]

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.

[Michelle Obama]

That's right.

[Brian Chesky]

Because what you what changed in the last 10 years, the2030s 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. And I 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.

[Michelle Obama]

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. 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? How are you here? Why are you talking in this way as compared to some of your peers?

[Brian Chesky]

I remember when I first started Airbnb, some one investor told me, I pitched them and they said, I love everything but you and your idea. And I said, what does that mean? They said, well, strangers that never stay there to strangers. And designers don't start companies. Tech companies.

[Michelle Obama]

Yeah.

[Brian Chesky]

So the answer to why am I different is I'm a designer. I think technologists start with the technology. They start with a solution and they search for a problem. I think a designer starts with a problem. They start with a solution for the world and they work backwards to the technology. When I came to Silicon Valley, the word technology might as well have been a definition, dictionary definition for the word good. That technology was progress. And every release of Technology was a forward step for humanity and so what we need is more technology. I think we probably should think of technology not as good or bad. It's on balance good. But I think we should think of it as a tool. Are tools good? A hammer can build a house. It can be used as a weapon. It depends on how you use it. We're putting the most powerful tools ever devised in the history of humanity in the hands of young people and even children. Jony I've is the person who designed the iPhone. I got to become friends with him. I know his children and he really did not allow his children to use the phone very much. I'm friends. I got to know Reed Jobs, Steve Jobs son, and Steve limited the use of his device. The people who invented these devices limit the use of these devices not because they think they're bad, but because so much of life must be experienced in the real world. And I think it's really important. And I think I also share your concern.

[Michelle Obama]

So what's gotten in the way of the use of this technology solely for good? What is keeping this country and some of the folks who've created these devices from sort of standing up and supporting some kind of limits? I mean, because it's difficult for parents, for schools, for communities to find ways to parent around these tools and it doesn't feel like the tech community is on the side of kids and families.

[Brian Chesky]

One of the conversations I had with President Obama when he was giving me advice, he told me something that I'll never forget. He said you should institutionalize your intentions so that even when you're a public company, you can, you know, make sure not to compromise your vision. And what he meant by that, I think was that you should be more thoughtful about what you're making, why you're making it, and the impact of what you're making is on people. And he, you know, one of the things we talked about is a lot of leaders in power. I don't think they have bad intentions. They're more like self driving cars.

[Michelle Obama]

Yeah.

[Brian Chesky]

It's not that they are trying to go somewhere bad. It's that they're not really thinking about where they're going. And if you're not intentional, you know, these tools get. You cannot invent a tool, put it in the hands of a billion people and it be used for reasons you totally intended. It's going to have unintended consequences. And it's not necessarily your fault that consequences were unintended. But the question is, once it's used, what do you do with that information, do you pivot or do you kind of, like, put your head in the sand? And I think it's really, really important for us to always take responsibility to imagine the kind of world we want to live in. Maybe imagine the kind of world you want your children to live in and say that we can design that world. And I think that's the role of a designer. The role of a designer is to assemble things, components or technology to better suit the needs of society. And you're constantly in a state of redesigning based on getting more information. And it's easy to get defensive. Well, those people are just attacking me, so I'm gonna defend. But at some point, you do have to look in the mirror and ask, well, is what they're saying true, and if it is true? And sometimes, usually what happens is some things they're saying is true and then some things aren't, and not take it personally and say, well, I'm gonna address the part that is true. And I think that is just what we need. And I do think there's a new generation of technology leaders that I do think are just seeing the impact that their forebears had, and they're starting to try and anticipate the needs a little bit more.

[Michelle Obama]

And money makes it so hard.

[Brian Chesky]

It makes it really hard.

[Michelle Obama]

And the amount of money, I mean, Brian, you were a billionaire, and you became a billionaire at such a young age. Mid 30s, mid-30s, and so many of your peers. And that's what you hear about in Silicon Valley. It seems like a lot of people are drawn to the industry not because of purpose or because even a love of technology. There are a lot of people that just want to get rich. And there was a time at which everybody was, you know, you start out at a startup company and you become, you know, if not a billionaire, then a millionaire. And that tends to be the driver. Can you talk a little bit about how that has kind of distorted some of the goals and the aims of people who, as you say, they aren't. They don't have bad intentions, but it just seems like people have gotten lost in the money.

[Brian Chesky]

When I started Airbnb, there weren't a lot of billionaires in tech. There were hardly any. And I kind of joked that if I wanted to make money, the last thing I would have done is started a company called Airbed and Breakfast.

[Craig Robinson]

That's right.

[Brian Chesky]

So when we came to Silicon Valley, it was much more passion projects because there wasn't as much money. We assumed we weren't Gonna be successful. And we just made something for ourselves that we loved. I think the values have changed a little bit because there's so much money that is so tempting. And I do think the money creates, as we talked about, this momentum, this, like, pressure, this, like, blinding, like, magnet. And I think it can distort, yeah, a sense of people's priorities. And having gone through this now, it's really difficult. But sometimes you have to get to the top of the mountain to realize it was never about that mountaintop. And you're not much higher than you ever were before. And I think it is true that, like, you know, I mean, why do people want money? I guess cause they want status, they want happiness. And I think I like someone having, like, made a lot of money in my, like, mid-30s. I can now say, like, it does provide a lot for you, but only to a point. And money just amplifies everything. And if you don't have a really great foundation, the money is going to actually potentially cause you big problems. And actually, I had a bit of a personal kind of crisis of my own in my mid to late 30s. Because my parents are social workers. I had more success than I ever thought. But the thing about being very successful in tech and making a lot of money and all this is no one ever told me how lonely it would become. And I started realizing, oh, you know, it was weird. Like, I had old friends that were middle class, and I'll be honest, a lot of them seemed happier than me at that point in my life. And I was like, I'm like, what is going on? And I realized, and actually President Obama helped me see this, that I was just becoming really isolated, that the more success you get, the more isolated you get. And I think people dream of success, but what they don't realize is a lot of with success comes disconnection, disconnection to your past, to yourself, to your friends. And I think a lot of what I've tried to do the last handful of years is to reconnect, to not live a life of isolation. I think it's made me like, a better friend, but also a better leader. Because how do you make things for regular people when you're no longer one of those people yourself?

[Craig Robinson]

I'm just so glad to hear you say that, because you remember our dad used to say the same thing. He used to say, if you're chasing money, you're gonna lose whatever little happiness you have. And he was a guy who had nothing, so nobody believed him because he didn't have money. So I really appreciate you being so open to talk about loneliness. And I wanna know someone in your shoes who, like, everybody's looking at Brian Chesky, okay? He's got money, he's happy, he's got a company. How did you combat that loneliness with all the expectations of being. You can't be unhappy.

[Brian Chesky]

Exactly. It actually started kind of long ago where I basically, if I were to just go back when I came to Silicon Valley, I came to Silicon Valley in 2007. That was a very important year for Silicon Valley. Cause two things happened. The first thing was the iPhone was created and announced. The second thing is that Facebook opened Beyond Schools. So 2007 was like this year of, like, a supernova energy, because suddenly social media was about to be on phones, and we all felt like it was about to make the world connected. And what I noticed over the course of a decade or a decade and a half was that pretty soon people were living on devices, and I think the products were starting to be used the way we didn't intend. Social media may be the most successful product in the world that was invented and actually uninvented in the sense that at one point, it was called social networking. Then your friends pretty soon became your followers. And when your friends became your followers, it no longer meant. It was about connection, it was about performing. And when you start performing for other people, you lose intimacy and you lose authenticity, which is not necessarily a bad thing, but it's not meant to fill the void of connection in your life. And I started thinking to myself, I said, I want Airbnb to be able to help combat loneliness, because we were about connection in the real world. We weren't about devices. We spend our whole lives on devices. And I noticed I've never had a dream where a device is in my dream. There's something about that. The real world is the real world.

[Michelle Obama]

Yeah, but you've always been an intentional person. Even your relationship with Barack. I mean, you reached out.

[Brian Chesky]

Yes.

[Michelle Obama]

You. Before you had even had any conversations or had any kind of mentoring discussions, you reached out to him because you wanted to be a different kind of entrepreneur. Can you talk more about that?

[Brian Chesky]

Yeah, absolutely. Well, I thought to myself, airbnb is a community. Who's the most famous community organizer in the world? I had this unbelievable experience where I got to, like many entrepreneurs, meet President Obama. I spent some time with him. And then after he left the presidency, I just was really shameless about reaching out to him, asking for advice, asking for mentorship. And he would meet with me and he'd give me advice and I would take it and I'd like, do all this work and I'd go and I'd like a teacher. I'd show him the assignment and said, and then he'd give me another assignment and I'd do it and I'd give it to him and then he would do another assignment. And at one point in 2018, we had a standing one hour call every week. And I basically had my day job during the day and then I had my night school with the former president where I would get these assignments. But it changed my life. By the way, he's the one who told me to reach back out to my old friends. He said, I have a circle of 10 to 15 really close friends. And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or call them, I have to get them up to speed in my life. So therefore I'm not maintaining those relationships. But I think the thing that President Obama taught me was to be more intentional. He literally said, so many leaders are like self driving cars. Use that analogy. They're not intentional, they're like a car, but they never put the destination in, so they're just driving somewhere. And he made me really be intentional about like, what do I want out of my life, out of the company. I ended up writing down a whole bunch of principles. I tried to institutionalize them for the company. I think it made a really, really big difference. And he kind of taught me a little bit how to think more deeply because I think as an entrepreneur there's an element of impulsiveness, spontaneity that's important.

[Michelle Obama]

Well, it's rewarded.

[Brian Chesky]

Yeah, you need to like, have an idea and you need to just do things and you. It's actually important when you first step in the ed not to overthink things. And so you just go and you go and you don't overthink. Because if you overthink and you're like, get stuck in business plans, nothing ever happens. And the entrepreneur has to do a thousand things a thousand times. The problem is when you never make the shift. And at some point you have to go from an entrepreneur to a CEO, and a CEO can't operate that way. A CEO has to realize, like, I'm responsible, I'm a steward for a community of hundreds of millions of people. Thousands of people's job depend on me. I gotta actually think like, if I do this, what are the second or third order consequences? We as entrepreneurs and tech folk, we're not trained to do that. And so I think it's hard to make that shift.

[Craig Robinson]

Can I make a reckless speculation here? Because I'm sitting here listening to Brian. So this is my first time listening to Brian, and I want to go back. And I'm. In my mind, I'm trying to figure out what makes him different. What do I see here that's making him different? The same questions you're asking. And can I even speculate that most people don't know this about you, but I did, in doing my research, that Brian grew up a hockey player, right?

[Brian Chesky]

Yeah, that's right.

[Michelle Obama]

Oh, sports. It all comes down. Okay, all right.

[Craig Robinson]

Make it make sense, but just let me finish. Being an athlete, you know, you're naturally. So you've been raised as a team player.

[Brian Chesky]

Yes.

[Craig Robinson]

Here's the reckless speculation. I'm not sure that your brethren in tech had that same experience. And could that be a reason why you take a more humanitarian look at technology when the others don't?

[Brian Chesky]

That's actually profoundly stood insight. And I would.

[Craig Robinson]

Excuse me, did you hear what you said?

[Michelle Obama]

Whatever. All right.

[Brian Chesky]

It really is. No, you're right. Thank you. So many people in our industry, they're so talented, they've got so many gifts. But I do think this is really interesting. They really struggle shifting from being a founder to CEO. And it's because being a founder is kind of a single player sport to some extent. And being a CEO is almost the definition of a team sport. And you also have stakeholders beyond your, like, your team. You have, like, investors and shareholders. You have, like the public good society. You have your guests, your host or your buyers or sellers.

[Craig Robinson]

You gotta be a player. You gotta be a player coach.

[Brian Chesky]

You gotta be a player coach. And also you gotta teach people. You gotta, like, your job's to make other people around you better. You stand on the shoulders of others. I think that's really important. I mean, my dad, by the way, he never, you know, it's funny, my dad never rewarded me for being talented, which I think was a good thing in hindsight. He only rewarded me for putting my best effort forward and being a good team player.

[Michelle Obama]

When you talk about the next generation of entrepreneurs, that brings to mind the current financial instability that we're experiencing. I just want to get your sense of what impact do you think that will have on young entrepreneurs, Their ability to become the next you? Because they have to go through that ramen phase. Right. And with this current market instability, it seems like it's gonna be harder for that next generation to get the foothold that you guys had. I mean, you guys were developing Airbnb in a pretty. You know, it was a pretty good market for that. Right. There was capital everywhere. People were investing, there was a hunger for this new technology, which is why how Silicon Valley came to be, because there was money out there for it. And right now we're hearing stories about new startups because of these tariffs. I mean, people. Some people can hold on, but other people are not only losing their businesses, but they're losing their homes in the process. So I'd love to get your take on that.

[Brian Chesky]

I mean, obviously, this is evolving week to week as of last week. And I know entrepreneurs. What they were telling me was that a lot of fundraising, for all intents and purposes, was kind of on hold.

[Michelle Obama]

Yeah.

[Brian Chesky]

So there was a whole bunch of people that were raising money. The deals are kind of on hold. A lot of limited partners and investors are just, like, hunkering down. And what we know about investors, they don't like uncertainty. I think people are going to sit this one out until things stabilize. And if they don't stabilize, we're going to be in for a very prolonged kind of dry spell for fundraising. If you did not go to a prestigious school, if you weren't purely a team of technical engineers, if you're not trying to create an AI company, just trying to create a business that will.

[Michelle Obama]

Be more difficult, which is 99% of people.

[Brian Chesky]

99% of people. And so I think that is that environment wants a good economy. Now, there is a silver lining. The economy was initially good when we started Airbnb, but then when we went to raise Money, it was 2009, during the financial crisis, and a lot of great companies have been started in a recession. And the one. I don't wanna say it's a good thing, but what it does is it teaches you a certain type of discipline. A tough economy teaches you a discipline that gets institutionalized into your culture, that a great economy, an economy of abundance, overabundance, can kind of help you perpetuate, like, bad strategies and be a little less disciplined. So I think the good news is a lot of great entrepreneurs are incredibly resourceful and they will find a way to work. But we absolutely need, like, a very stable economy. And I do think that, you know, I had the privilege of having a tech company and I had a lot of connections, and my co founder went to Harvard, was computer scientist. And so we probably got some opportunities that now everyone will get. And so the question is, how do we make sure More people have economic opportunity, and I think we're going to need a very healthy economy for that.

[Michelle Obama]

Yeah, it's kind of scary.

[Brian Chesky]

Yeah, yeah.

[Michelle Obama]

What would you tell young people out there now? And I'm not just talking about the entrepreneurs, but they're, you know, I mean, I have kids. They are just starting their lives. You know, they're one's in film, one's going to grad school to study mental health, maybe go into psychiatry. But I'm talking to so many young people who are deathly afraid of their futures in this climate. They're not just worried about jobs. They're worried about being able to become the next entrepreneur. They're wondering whether they'll have health care and housing, whether they'll be able to pay off their student loans. In your seat, what would you tell them right now? What advice would you give them?

[Brian Chesky]

Somebody once told me a metaphor for where we are right now in the world, especially, maybe in part, good technology. That technology was like a train, and all you had to do was get on the train of progress and you could ride it into the promised land. And now a lot of people feel like they're on the train tracks and the train is coming for them. I think there's a lot of fear, there's a lot of concern in the world. My advice to young people is to dash into the future, to use these tools, to lean in, to not brace. Seek out mentors, and maybe your mentor won't be a former president. But my first mentors weren't either. There were people that were three years ahead of me in my career. It is going to be profoundly different. And whether or not that different is better or not depends not on. I don't think it's depending on people like me. I think it's dependent on people in their 20s. The next generation is going to decide what happens. And so it is this generation. There is cause to be afraid, but there's also cause to be hopeful. This is their world. They're about to take it over or they're going to contribute to this world. And I think that new technology is going to level the playing field and allow a door to open for a new generation to step in.

[Michelle Obama]

That is, if everyone actually has access.

[Brian Chesky]

Yes, that's critical.

[Michelle Obama]

And that is just something that I want everybody to have in their minds, that for a tool this powerful, equity, equality, justice, fairness has to play out because we're in line for the opposite to happen right now. As you know, basic federal workers who are making up a huge percentage of Jobs and livelihoods for people are being laid off as there are still fears that AI will replace real people. It will replace teachers and accountants and bus drivers and truck drivers with no plan on how to stabilize or retrain or create another workforce. Those are gonna be jobless homeless people who won't be able to afford to go to college. They won't be able to afford healthcare. They won't have healthcare because there's no plan for that. And if you're of the wrong ancestry, if you speak the wrong language, if you're not the right color, if you didn't come from the right country, you know, there's no telling what can happen, right? So for that equity to happen, right. For that tool to really do what you say it's gotta do, the Constitution, democracy, all of that has to be in place. And the leaders who run this country have to value that. They have to understand that all ships have to rise. And I don't wanna go on a soapbox, but, you know, that's why it's not, you know, Hope has to be paired with real action.

[Brian Chesky]

I agree.

[Craig Robinson]

Yeah, I agree with you, Michelle. I don't think it's a soapbox. I think you're absolutely right. But hope has to also be paired with. For these 20 year olds to know, to go forward, we have to be intentional, to use you all's term, about training them as parents.

[Brian Chesky]

I agree with that. Right.

[Craig Robinson]

I think what we cannot do is be caught up in our own sort of social media and let our kids just sort of get dragged up. We have to raise them. We have to be thinking back to what you were saying about the founders that you talked to who didn't let their kids use their phones. But we have to be intentional about.

[Brian Chesky]

Teaching people how to use the tools 100%.

[Craig Robinson]

And that is why I'm so happy we're doing this and have you on here, because I don't know that parents are equipped.

[Brian Chesky]

It might be one of the defining things for the next generation is what is our relationship with these devices, with social media, how do we use it and how do we use technology to lift people up, to make sure that it helps parents, it helps young people and that people in positions of power like us, that we're not using, we're not closing the door behind us, that we're like keeping the door open and we're encouraging the next generation to walk through that door.

[Michelle Obama]

So as you're, I don't want to flip it a bit as your, you know, quasi big sister on the Other half of your mentoring team.

[Craig Robinson]

She just inserted herself. Just inserted herself.

[Michelle Obama]

You know, I want to. How are you using these tools to find your life partner? What are you doing?

[Craig Robinson]

Come on.

[Michelle Obama]

I mean, no, I want to know. And for those listening, looking, you know.

[Brian Chesky]

I come on podcasts. That's what I do.

[Michelle Obama]

Brian is handsome, he's funny, he's whip smart.

[Craig Robinson]

As your new mentor, brother in law.

[Brian Chesky]

Thank you.

[Craig Robinson]

You do not have to answer this question.

[Michelle Obama]

Yeah, let's talk about this.

[Brian Chesky]

I've not had a lot of success with the tools. If I'm being honest. The best success I've had with meeting people is the old fashioned way. Through other friends or just meeting someone in the real world and that has still been. Or having friends make introductions at dinner tables.

[Michelle Obama]

Yeah, yeah, yeah. Well, we've got it. Anyone out there who has good friends with good values? Because what's some of the best advice that Barack has given you about dating and finding a partner?

[Brian Chesky]

One time I was like, I met somebody and I was about to go on a date with. I went on a date with them, and I remember telling him, like, oh, my God, like, she checks all the boxes and like, this, this, this, this, this. And I remember him saying something, he said, it's not a checklist.

[Michelle Obama]

Yeah.

[Brian Chesky]

And I said, oh, interesting. And I'm like, yeah, it kind of makes a lot of sense. He's like, the right person is someone where they've got this, like, weird laugh or snort and you find it really funny. And it's like, in other words, it's not necessarily what you think you're looking for. And you're not dating a checklist. You're dating a real person, and the real person makes you feel a certain way. And I think that was. I think it was like a really, really important piece of feedback, piece of advice, because I think this also is a bit of a problem with dating in the world today. You know, one of my best friends is a woman named Whitney Wolfhard. She started a dating app, Bumble. And one of the things that we've discussed, and I think where she's taken the company is online dating especially, has come a world of judgment. You literally swipe right within milliseconds. Swipe right, swipe left, swipe right, swipe left. If people say have a type, the question I'd have back is, have you met enough people in the world to know there's a type?

[Craig Robinson]

There you go.

[Brian Chesky]

And I think your type is your predisposition based on the limited people and experiences you've already had so many people end up with people that aren't, quote, their type. And I think that. And this is similar to social media, we probably need to live in a world of curiosity, not judgment. Instead of swiping, we need to, like, discover and find what's really interesting to people. And so I think that, like, that's probably one of the things that we need to do more of.

[Craig Robinson]

So this is what happens when you have a good guess that you know, right. Because you guys have come up with these takeaways for the other Brian that I didn't have to say, okay, what are the takeaways for Brian? But I wrote some down here. First of all, there's too much reliance on social media. All right? So we have to be more intentional at not relying on social media as much.

[Michelle Obama]

It's a tool, but you can't like all tools. You can't abuse it, and you can't only use one tool.

[Craig Robinson]

Yeah, well said. And then here, this is what I like. Most of life, you have to do in the real world, not on your device. It's just such a simple but profound advice. And then finally, Mish, you said you have to be comfortable living with some obstacles, and we are trying to avoid that. Is there anything else that we need to share with Brian to help him get well?

[Michelle Obama]

I want Brian, people like Brian, young people, to understand that the future of this technology, as Brian says, is in their hands. And it's not just about the technology. It's not just about creating the best app and having the best tool. You have to think purposefully and intentionally about the use of that tool for young creators out there, for people who want to be the next tech giants. You can't just have a great idea. You have to have a broader purpose of the why. And it has to be greater than making money. It has to be something bigger than yourself. You have to be a team player. You have to think about the whole of it. That is as much a responsibility as anything, I think. And I think our politics, our democracy, having one that is healthy and vibrant, I think is so essential to ensuring that these tools aren't abused. You don't have one without the other. You can have these great tools, but in the wrong hands, without the wrong regulations, without the right safeguards, they can become very dangerous. And if everyone doesn't have access to them, if we aren't living in a society with equity, we are not going to achieve the utopian goals that these. The goods that these tools can offer. We will not do it. If everyone doesn't have equal access, but those were just some of my thoughts.

[Craig Robinson]

Anything to add, Brian?

[Brian Chesky]

I think on a personal front, I think I would just say like maybe two things. And there are two things that I learned in part from President Obama, which is number one, I think seek out mentors. And by the way, seeking out a mentor doesn't have to be like, can you be my mentor? It's just somebody doing something interesting and you are proactive in reaching out to them. Because I think for young people, the number one thing they you need to learn how to do is how to learn.

[Michelle Obama]

Yes.

[Brian Chesky]

And some of the best ways to learn are from other people. And some of the best ways to learn from people are again, in the real world. It can, you can still, AI can teach you a lot, but like you need to have experience in the real world. And, and I think that's really important. And the other thing is, yeah, like you can use social media, but like make sure you have real friends in the real world. And one of the most important things you can do, like one of the simple life hacks to make your life happy is to basically just rekindle old relationships. And if all that time you spent on social media, to the point if you trade some of that with in person connection with people from your past and then meeting new people, it's gonna have a huge impact on your life. And also when it comes to mentors, like a lot of people are afraid to ask other people for advice or help. What I've realized as a huge surprise I've had is so many people feel deeply honored when someone asks them to.

[Michelle Obama]

Help or ask them for advice. Yeah.

[Brian Chesky]

And I never, even before I was the founder of Airbnb, when I was totally broke, obscure 25 year old people wanted to help me when I reached out to them because it made them feel good and it gave them a sense of purpose. I think the vast majority of people, if they reach out to someone, someone will want to help them. They reach out to old friend, the old friend will want to reach back out to them. And that is the path for reconnection. It's a path for relationships and it's a path for purpose.

[Michelle Obama]

Yeah. Beautiful. Beautiful.

[Craig Robinson]

Well, Brian, you have been incredibly gracious with your time and your insights and taking abuse about your dating life from my sisters.

[Michelle Obama]

I don't think that was abuse.

[Brian Chesky]

No work in progress.

[Michelle Obama]

I don't think that was.

[Craig Robinson]

But we really appreciate you being here with us, man.

[Michelle Obama]

And let me just say, I'm so proud of the person you have become.

[Brian Chesky]

Oh, thank you.

[Michelle Obama]

This journey of yours could have taken you in any number of crazy directions. And a tribute to your parents for getting you started with a clear head and doing the best you can to stay. Stay sane in some unusual circumstances. So thank you. Thank you for sharing your insights so clearly and warmly. And I know we'll see you this summer at dinner.

[Brian Chesky]

I can't wait to see you this summer.

[Michelle Obama]

Can't wait. Maybe with a date.

[Brian Chesky]

Yes, that's a goal.

[Michelle Obama]

I usually don't let people bring dates, but if you get a date, then you'll.

[Brian Chesky]

I can get a plus one.

[Michelle Obama]

You can get a plus one.

[Craig Robinson]

Man it.

[Brian Chesky]

Please.

[Michelle Obama]

I want to go to a wedding soon.

[Craig Robinson]

Oh, God.

[Michelle Obama]

Big wedding.

[Craig Robinson]

You know, you can tell her to stop.

[Michelle Obama]

Can.

[Craig Robinson]

She's not the first lady anymore.

[Michelle Obama]

Sam.