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

Episode Date: May 21, 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.

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. Have you ever? Right to the relationship. Brian, you don't have to be filled pressure. No, but we've never talked about this. He just got here. Have you ever? Her husband has been trying to set me up before.

So. Yeah, I'm very, I'm very invested in Brian's love life. Craig Robinson. Hi. How you doing, dude? Good. Neesh, how you doing? I am good. I was going to say you look refreshed. Thank you. I am pretty refreshed. You look refreshed. You shouldn't be because you still have a little bitty kids. I know. I know. I should look worn out. I should stop calling them little bitty.

Yeah, they're not little bitty anymore. And they're almost as tall as me. Yeah. But yeah, you you're coaching doing, still doing all this stuff deep into the. I'm still coaching. 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. You sent, or Kelly sent a picture. Austin's starting to drive? Yes. Oh, this is a good story.

So you remember the green car? The green car that's like 100 years old. It's a 1999 GMC. You talk about an old man keeping a car forever. 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. Okay, way to go.

Yes. Brought everyone slow clap on that one. 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. 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.

They feel like they came after all the good stuff. It's right. They did. All the good stuff. They kind of did. They kind of did. They did. We'll have to spend some time talking about the stuff they missed.

Yeah. Well, I'm excited because today we have our first really sort of tech expert. Yeah, yeah. We're going to 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's 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. Oh, that's a huge compliment. And we're going to be talking a little bit about social media, tech. Loneliness. A loneliness. So we got a lot on our plate. So let's not waste any time. Let's get Brian out here. Well, let me give him a little bit of an minute.

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. And in 2007, Brian became Airbnb's first host. But you know what's cool about that? See, I want to hear about that because I don't know if I would be able to do that. He's still a host. I know. That's, 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. Here he comes. Hi, Brian. 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. 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? I have guests come and they can book on Airbnb and do they know it's you? Yeah, they definitely know it's me. And they typically- Do they have to pay more? It's actually free. It's a free. So it's kind of like, you know, if you kind of. If you kind of get lucky enough, I think you can stay with me.

And I have some really cool people I've had to stay with me. And when they come and stay, they stay. I have a two-bedroom house. It's not a big house. Really? Really? Really? Really?

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 Cheskeskes chips. Would tell us about Chesquish chips. Yeah, these are Chasua cookies. They've been in a family, bold family recipe. I got off Google two years ago. Well, why haven't you made us Cheskey's chips?

Well, you can book on Airbnb. Oh, man, I got a day and my guest for it. 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. What's the weirdest guests that you've had?

Can you say without insulting anybody? Or is everybody just really nice to, are they? on their best behavior. 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 stay with me, that they were reloading my page

like thousands of times. Oh my God. I thought to myself, I don't think it's a good sign, but maybe a little bit much, but it turned out to be an amazing person. Like concert tickets, right? Like this reload reloaded. And I'm like, these chips are not worth it. I've got to be out of see. They're pretty average baker.

That's great. Yeah, 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. Have you ever? Right to the relationship, Brian, you don't have to be filled pressure. No, but we've never talked about this. He's just got here. Have you ever? Her husband has been trying to set me up before, so.

Yeah, I'm very, I'm very invested in Brian's love life. So you've never met anybody that way. Have you found? No, no, I haven't. Most of the people have stayed are couples, actually. Oh, that's sweet. Yeah, it's. But now you've given the whole world an idea. Gee whiz. Wait, so Barack has actually tried to fix you up. Is he any good at it? We'll see, I guess. Remains to be seen. But, yeah, no, he's definitely very invested and he's provided a lot of relationship advice to me, actually. 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? Yeah, I'll tell the, I'm from upstate New York. My parents were social workers. My mom once told me growing up, like, I chose a job for the love and I paid, I could pay no money. So you should make sure that 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 pick 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 Design.

RISD. RISD. Yes. In Providence. And we have a Providence connection. We do. We do. I coached it Brown for those of you who didn't know that.

And RISD was right down the hill. And it was a wonderful place. I love Rizdy. 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 the 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. We have this idea. We said, what if we just turned our house into a bed and breakfast for a design conference? No way. 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 airbed and breakfast.com. And that's where the name Airbnb comes from. And what year was that? This is 2007. 2007.

And we ended 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 as surprising. 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, well, the old roommate, Nate is, and this leads to how I got to know President Obama. Well, that's 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 used in the marketplace. How do you get people 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. Oh, okay. And then Senator Obama was just nominated as you remember. And I remember sitting a home with my roommate show. And there was like the CNN on TV, GNC housing crisis. They move him from the basketball arena to the football stadium.

And they're like, wait, where are all these extra people going to stay? That's how we launched. We launched for 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 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 air beds aren't selling. Maybe there's money in breakfast because not for what sleeps on air beds, 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. And it was this box. We were like, well, what would a Barack Obama? It was so obvious. He had the iconic O, like Cheerios. We called the 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. Who were you selling these two? You know what's funny? No one wanted the airbeds. They were like, I'm that stag at a stranger's house. That's crazy.

I'm not sleeping out of airbed. See, now that makes sense. That would be my reaction. Exactly. You know, you talk about this air mattress. I'm like, I don't know if I'm going to rush to the air mattress. So you should have called me. I would have told you that early on.

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. Minor details. I know details. But we basically, I remember once a producer, 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 owes a day. So I basically got a media list. The media list 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 it spread all over the news.

And that's how we funded the company. It's a joke where we were like serial entrepreneurs. So you sold enough cereal to fund the company? To fund the company. Was there actual cereal in the boxes? Were true artistic integrity mattered to me. So we actually had the exact cereal that was photographed on the box inside. I didn't realize that that's how you funded the company.

You sold that much cereal that you got. About $35,000 of cereal. Wow, wow. So it only took $35,000. You only needed $35,000 to get the company going. 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, like, 26-year-olds are raising like $100 million for 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. Raman profitable means your company is profitable if everyone, the company only lives on ramen. So that was our goal. So the bar was low.

We slept on air batchuses. You know, we live 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 in 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. And we wanted to connect and travel different than our parents. And we wanted to have a more authentic way of traveling. We wanted to live like a local. And so this female totally new to us, even though it was weird to others.

Now, did you come to the idea of Airbnb through your experiences? I mean, you're in design school. You're not a tech person. He's an artist. And you're an artist. You know, and you come from social workers. When did you get that spark that I'm going to go into business? I mean, was it, did it just, was it just something that continued to roll on?

You were so far in once you got to San Francisco. It was actually probably a 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, 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? She's like, a real job is one that has health insurance. That sounds like a parent. That sounds like our mom. 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. You got to start somewhere. Yeah, yeah. And then one day, you know, when I quit my job, I remember going home for a 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 to mom.

And that's what I realized. When you're starting, it's mostly in your head until you manifest it. So now you've 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? I'm so excited about this because I never thought we get to this point. That very first weekend was about connection. It was about connecting with one.

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 Marsha who went to school here and we could bring the humanity out of everyone. And we thought, you know, what if you can Airbnb be more than an Airbnb? What if you can Airbnb be a chef to come to your house? What if you can Airbnb be a masseuse? What if you can Airbnb be 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.

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. I was blown away. 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. 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've 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 is a great

saying at Apple in the 1980s when they developed a 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 it 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, you know, 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? I remember when I first started Airbnb. 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 have never stayed other strangers, and designers don't start companies, tech companies. Yeah. 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 human. 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 history of humanity in the hands of young people and even children. Johnny Ive 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 Jobson. 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. 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 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. 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 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 one of the things we talked about is a lot of leaders and power, I don't think they have bad intentions. They're more like self-driving cars. 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 that consequences are 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 like 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 going to 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 are saying is true and then some things aren't.

and not take it personally and say, well, I'm going to 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. And money makes it so hard. It makes it really hard. And the amount of money, I mean, Brian, you were a billionaire. and you became a billionaire at such a young age.

And 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, 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 don't have bad intentions, but it just seems like people have gotten lost in the money. When I started Airbnb, there weren't a lot of billionaires in tech. There were hardly any.

And I kind of joke that if I wanted to make money, the last thing. it would have done and started a company called Air Bed and Breakfast. That's right. 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 going to 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 it, and I think it can distort, yeah, a sense of people's priorities. And having gone through this now, it's like, it's really difficult, but sometimes you have to get to the top of the mountain to realize that was never about that mountain top 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 because they want status. They want happiness. And I think I've, like, someone having like made a lot of money in my mid-30s, I can now say, like, it does provide a lot for you, but like, 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-delight 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.

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, 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 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 regularly people when you're no longer one of those people yourself? 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 going to 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 want to 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? Exactly. It actually started kind of long ago where I basically, if I 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

because 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 and devices. And I noticed, I've never had a dream worth a device is in my dream. There's something about that.

The real world is the real world. Yeah. But you've always been an intentional person. Even your relationship with Barack. I mean, you reached out. Yes. 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? Yeah, absolutely. Well, I thought to myself, Airbnb's a community. who's the most famous committee organized 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 like, and they'd give me another assignment and I'd do it and I'd give it to him and they'd 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, like, I have a circle of 10 to 15 really close. close friends. And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or called 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, like, 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. Well, it's rewarded. Yeah, you need to like have an idea and you just do things. It's actually important when you first have an idea not to overthink things. And so you just go.

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. Yeah. 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 got to actually think, like, if I do this, what are the second and 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. 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 the about you, but I did in doing my research that Brian grew up a hockey player, right? Yeah, that's right. Oh, sports. It all comes down to sports.

Okay. All right. It doesn't all come down to sports, but just let me finish. Being an athlete, you know, you're naturally, so you've been raised as a team player. Yes. 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? That's actually profoundly student insight. And I would, excuse me. Did you hear what he said? Okay, whatever. All right. It really is. No, you're right.

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 or 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 team you have like investors and shareholders you have like the public goods society you have your guest

your host or your buyers or sellers. You got to be a player, you got to be a player coach. And also you got to, you got to teach people. You got to like your jobs to make other people around you better. You stand the shoulders of others. I think that's really important. I mean, my dad, by the way, 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. 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 you think that will have on young entrepreneurs, their ability to become the next you because they have to go through that ramen phase.

And with this current market instability, it seems like it's. going to 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 a new startup. 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. 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 of purposes was kind of on hold. 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, like, prolonged kind of dry spell for fundraising. If you did not go to a prestigious school, if you weren't like purely a team of technical engineers, if you're not trying to create an AI company, just trying to create a business,

they will probably, that will be more difficult. Which is 99% of the people. And so I think that is, that environment needs, 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 want to 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, over abundance, can kind of help you perpetuate, like, bad strategies and be a little less discipline. 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, who was a 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. Yeah. It's kind of scary. Yeah, yeah. 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. Yeah.

They are just starting their lives. You know, one's in film, one's going to grad school to study mental health, maybe going to 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, you know, 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?

Somebody once told me a metaphor for where we are right now in the world, especially maybe in part of technology. That technology was like a train. And all you had to do was get on the train of progress and you can 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 the world, my advice to young people is to like dash into the future, to like, to like use these tools, to lean in, to not brace, seek out mentors. And maybe your mentor won't be a former president, but like my first mentors weren't either. There were people, there 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. That is, if everyone actually has a lot of. access. Yes, that's critical. 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. Yes. 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, you know, there are still fears that AI will replace real people, you know. 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 going to be jobless, homeless people who won't be able to afford to go to college. They won't be able to afford health care. They won't have health care 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 got to 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 want to go on a soapbox, but that's why it's not. You know, hope has to be paired with real action. I agree with you, Michoud 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.

I agree with that. Right. I think what we cannot do is be caught up in our own sort of social media and let our kids just sort of of get dragged up. We have to raise them. We have to be, I'm 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 teaching people how to use the tool. 100%. 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. 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. So as you're, go ahead. I don't want to flip it. a bit as your quasi big sister on the other half of your mentoring team. She just inserted herself. Just inserted herself. You know, I want to, how are you using these tools to find your life partner? What are you doing?

Oh, mech, come on. I mean, no. I want to know. And for those listening looking, you know, look, Brian. I come on podcast. That's what I did. is handsome, he's funny, he's whipsmart. As your new mentor brother-in-law,

you do not have to answer this question. Yeah, let's talk about this. 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. We're just meeting someone in real world, and that has still been, or having friends to find, make introductions at dinner tables. Yeah, yeah, yeah. We've got to, 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? 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. And I remember him saying something. You said, it's not a checklist. Yeah.

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. Yeah. 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, that was, I think it was like a really, really important piece of fee. piece of advice. Because I think, I think this also is a bit of a problem with dating in the world today. You know, one of my best friends is, when they went to me, Whitney Wolf heard, she started a dating at Bumble. One of the things that we've discussed, and I think where she's taking the company is, online dating, especially has become a world of judgment. You literally swipe right within millisecond, swipe right, swipe right, swipe left, swipe left, so left. If people say have a type, the question I'd have back is you met enough people in the world to know there's a type.

There you go. 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 we need to, 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 of people.

And so I think that, like, that's probably one of the things that we need to do more of. 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. So we have to be more intentional at not relying on social media as much. It's a tool, but like all tools, you can't abuse it and you can't only use one tool.

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. Yeah. It's just such 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 to the... Well, 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, you know, the best tool. You have to think purposely 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. Anything to add, Brian? 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, seeing 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 need to learn how to do is how to learn.

Yes. And some of the best ways to learn are from other people. And some of the best ways on from where people are, again, in the real world. You can still, AI can teach you a lot, but like, you need to have experience in the real world. 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 and 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 going to have a huge impact in 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, that's a huge surprise I've had, is so many people feel deeply honored when someone asks them to help or ask them for advice. Yeah. 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 an 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. Yeah. beautiful beautiful well Brian you have been incredibly gracious with your time and your insights and

taking abuse about your dating life from my sisters I don't think that was abuse no work in progress but we really appreciate you being here with this man and let me just say I'm so proud of the the person you have become thank you this journey of yours could have taken you in any number of crazy directions and a tribute to your parents for, you know, getting you started with a clear head and doing the best you can to 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. I can't wait to see the summer. Can't wait. Maybe with a date. Yes, See, here we go.

That's a good call. I usually don't let people bring dates. But if you get a date, then you'll, I can get a plus one. You can get a plus one. Okay. Man. Please.

I want to go to a wedding soon. Oh, God. Can't wait. You know, you can tell her to stop. You can. She's not the first lady. She's not.