On with Kara Swisher - Airbnb’s CEO on Nomadic Life, Loneliness… and Cleaning Fees

Episode Date: October 20, 2022

Airbnb CEO and co-founder Brian Chesky took the company public, laid off 25% of its staff and navigated worker demands for flexibility – all during the pandemic. Oh, and his mom moved in (and made him quiche every day). In this conversation with Kara, Brian discusses the challenge of being professionally successful and, sometimes, personally lonely. They talk about how the pandemic may have permanently changed how we work, travel and live. And Kara gets answers about the company’s lack of transparency on those dreaded cleaning fees.  Before the interview, Kara and Nayeema talk about billionaires owning social media networks. They discuss Georgia congresswoman Marjorie Taylor Greene, who seems to be riding the MAGA train to amass power in the Republican party. And they reflect on the story of Iranian rock climber Elnaz Rekabi, who caused a stir on social media this week in the midst of the nation’s anti-government protests.  … oh yes, and they dispense some dating advice. If you want advice – it doesn’t have to be about dating – call 1-888-KARA-PLZ! You can find Kara and Nayeema on Twitter @karaswisher and @nayeema. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Ready, set, grow. Go to ConstantContact.ca and start your free trial today. Go to ConstantContact.ca for your free trial. ConstantContact.ca It's on! So allegedly he did it. Just kidding. This is On with Kara Swisher and I'm Kara Swisher. And I'm Naima Raza. You're more likely to have a Twitter tantrum than a public. I guess a Twitter tantrum is a public.

No, I don't have those either. I don't have those either. You'll never hear about that. No, I don't have tantrums. I'm a professional Twitterer. I'm a professional Twitterer. But anyway, our guest today is Airbnb co-founder and CEO Brian Chesky. Yes, I've interviewed him many times over the years.

He is one of my favorites, which is a low bar, as I said to him on stage. One of your favorites. I thought that was Elon Musk, Cara, by the way. He's always good for news, right? There you go. Since we last spoke, it seems another billionaire has come in with a bid for a social network. Yay. Kanye West is apparently in talks to buy Parler, the right-wing social media site.

What do you think about that? Well, I don't think it's going to happen, allegedly. Let's put allegedly next to that one. I don't think it's going to happen. I think it's a marketing ploy. But I tweeted a photo earlier this week of Elon, Kanye West, and Donald Trump with each of the logos, each holding their Twitter, Parler, and true social logos, and asked folks for caption contents. I got hundreds and hundreds of replies. I was really surprised.

My personal favorite was two men and a baby. But there was lots and lots of them, and they were very funny. But is this really, I mean, this is three billionaires owning social networks. Is it really that different? Rich people have always owned the media. And I'm not talking about Murdoch. That's true. Bloomberg, but Jeff Bezos of the Washington Post, Sheldon Adelson of Las Vegas Journal.

It's not even a U.S. phenomenon. Like in Pakistan, the key paper, Dawn, is owned by two very wealthy family houses, for example. And you see that in the Philippines with the Yap family, et cetera. So what's happening here? Why you seem to be riveted by this. I am riveted by it because they're buying into businesses that are terrible. Those are all great businesses or were in their day, right? And Rupert Murdoch is a terrific business person, whatever you want to say about him being Uncle Satan.

That's you, Cara. You want to say that. They are great businesses. They're buying out of ego and into businesses that don't make money. And now the only one with a possible chance of making money here and not very much Elon Musk, because he's a very good business person. The other two, and Kanye has made amazing products, various things, but he always, as John Herman wrote in New York Magazine, he always crashes it into a wall, essentially. Donald Trump, let's just not speak of his business acumen. And so it's this trio of billionaires owning social networks, thinking this is how they're going to influence people.

And I think they're on the wane. I think these things are on the wane. Why do people who already have influence need to own a social network to have influence? I mean, I'm curious with Kanye, yay, for example, having been booted from Twitter and Instagram, right? This is why he's saying what he's, you know, saying that this is why he wants to buy Parler. I mean, Parler has become very small in recent months. It's fewer than a million monthly active users, I think, now in early 2022 at least. And it was above 5 million the year before, right after January 6th, et cetera. It was very popular. Do you see him being a game changer?

I mean, look, Jay-Z and Tidal, like when you have a celebrity affiliation, can that not be a booster, a multiplier for the business? No, no, no. It has to be a great business. It has to be a product that people like. I mean, my son likes his sneakers, I guess. Those worked. But it's because he was doing it with real businesses. This is not a real business.

There's just not enough of an audience. There's just not. And they don't get to yell at each other, at libs. There's no lib owning at scale. Yeah, there's no friction. As John Herman wrote, lib owning at scale. There's no friction. And so good luck. I's no friction. As John Herman wrote, lib owning at scale. There's no friction. And so good luck.

I think people come and look like it's like Trump social. People come and look, they screenshot, and then they take it to Twitter where there's other people to talk to about it. Yeah. All right. Let's get to our two newsmakers this week. All right. The first is Georgia Congresswoman Marjorie Taylor Greene.

And we want to talk about Elnaz Rakabi, the Iranian rock climber who caused a stir on social media this week. But let's start with Marjorie Taylor Greene. And we want to talk about Elnaz Rakabi, the Iranian rock climber who caused a stir on social media this week. But let's start with Marjorie Taylor Greene. Cara, your favorite, your other favorite, other than Brian Chesky. No, I would say not. But Marjorie Taylor Greene seems to be living large these days, according to Robert Draper's reporting in his new book, Weapons of Mass Delusion, when the Republican Party lost its mind. There's an excerpt of it published in the New York Times Magazine this week. Yeah, it was crazy. She was bragging on. I think, honestly, the way she bragged, I think she's in trouble, the way she was trying to say she had

so much power. She told him that to please the base House Minority Leader Kevin McCarthy was going to give her, quote, lots of power and lots of leeway. And also the quote, if he doesn't, they're going to be very unhappy about it. It's a weird threat from a tiny little lady who I understand is very fit, seems very fit. But in any case, it was ridiculous. If she has to say it, she doesn't have power. Just FYI. She denied it was a threat. She said it was, quote, reality, which is shocking because she embraces so many conspiracy

theories outside of reality. But Kevin McCarthy, who, if the GOP wins the House, will be the House majority leader, a very powerful person. He's denied that he's offered her some special position, but he's a little bit flip-floppy. Well, there's no reason to cut her right now, but there's no way they're putting any power in this woman's hands. I mean, you know, Halloween's coming up. She's like one of those things that scare us in the dark, that kind of thing. And one of the things that she does is constant racism and anti-Semitism. Are you kidding? And yet she's attendant. Are we just not two people who are outside of this world thinking she's irrelevant or scary and that she's super ascendant and

relevant in the party? She's not ascendant. She's loud. I mean, that's what Drag Race reported. I know, but he's selling a book. I'm sorry, but he's selling a book. And so here's what I think. There are people who are legislatively enabled that have power because of the things they do. Republicans and Democrats, really strong legislators, right? And they're making things happen for good or bad, whatever you agree with. But, you know, Obamacare, big legislation, all kinds of different things. You can think of dozens and dozens of them. She is internet enabled, essentially.

Internet, you know, instead of doing that, she's done no legislation, none. She's just, you know, all she's run is her mouth. But it doesn't matter because she doesn't, she hasn't done anything. She gives speeches. What occurs after she gives speeches? There's a 30% group of people who seem lost, and she appeals to them. They may grow in size. That is her only thing, is influence.

Well, but here's the thing. It's not just that she's talking. She's fundraising. She's a fundraising powerhouse. She's a brand. She's very effective in the rallies, if you see her. You know, she knows how to walk that stage. She can rile people up. I mean, these are not, this is not nothing. She's able to activate a population. It's something that a lot of this dodgier, older GOP who don't know how to connect with this digital age might find useful to them. I'm not saying she's going to be a legislative powerhouse. I think your theory is very interesting. She's definitely not a legislative powerhouse. She's internet-enabled is what she is.

But she's internet-enabled, but is that not the future in some way of politics? No. I think people are going to move away from these social networks. I think she's good at fundraising. That is absolutely true. And then she uses the internet for marketing. And she's borrowing from Donald Trump. Carrie Lake does the same thing. So did Donald Trump, I was going to say. I get it. I think he was powerful. Yes, I do. Yes, I do. Yes, I do. He is the witch from The Wizard of Oz, and she's a flying monkey. That's what she is. She's a flying monkey. All right, let's move on to our second newsmaker of the day. This is Iranian rock climber Elnaz Rakabi. And she was competing at an international competition

in Seoul earlier this week and doing so without wearing the mandatory headscarf of the team. Good for her. And so when social media people thought she was doing the protest, it looks like she was. She was unreachable. Friends couldn't contact her. And then she posted a statement on Instagram that seemed kind of forced upon her. She seemed like a hostage. That was the speculation. And of course, this is while the anti-government protests are ongoing in Iran. They've passed a month now after the death of Masa Amini for not wearing her headscarf. But, you know, just the language of how it was translated, and this might be a translation, but she's like, it was inadvertent and alongside the team based on prearranged schedule. So it's not like generally Insta

story chat, you know. Yeah, I don't think you forget to wear your headscarf, do you? Well, she said it fell off while climbing. I don't know, gravity. But on Wednesday morning, she returns to Iran. I don't know. It was gravity. It was probably a gravity protest.

Gravity is angry at Iran, so they pulled the scarf off. My headscarf fell off, you know, 30 years ago. I haven't seen it, so there you go. Did you wear one a lot? Did you wear one? I've worn one in Saudi or like to enter mosques, but I've never worn it socially. To wear it respectfully, you know. But this kind of thing is ridiculous.

But on Wednesday morning, she returns to Iran. She lands straight into a happy interview with state TV. It didn't actually look that happy. She was covering her head and she was quite low-key, and then she was kind of rushed off by a man. It's what a wonder. What do you make of that, Cara? I make that she's being forced by the government to do this for PR. I think they probably threatened her family would be my guess.

I mean, that would be my guess. I think she's probably realized she's screwed if she protests. And, you know, speaking of Liz Cheney, she didn't make that step, right? She didn't make that step of just stepping out and saying, no, no, thank you. So what do you think? What do you make of it? Yeah, a slightly different cost than Liz Cheney, I think. Slightly different costs.

I mean, and there have been, you know, female athletes and Iranian women who have kind of chosen to live in exile. And that's a tricky thing. You know, your family's still there. So there's a lot of ways that the government can hurt you if you're not there. But the striking thing to me in this is the role of these individual stories and galvanizing and focusing our attention in the social media age. I think whether it's Brittany Griner, the WNBA star in Russia, or Lujain Al-Hathloul, the Saudi woman who was

arrested for driving, or Masa Amini, who's the woman that, of course, whose death sparked these current protests. There's something about this one-person social media eye that is getting people to care. You know, it's getting people to notice. And I think it's a story. But I think it's really hard to know. The reporting is so cloudy. BBC is probably, for me, the best source on this. They seem to be taking the position that this was. I think they're using words like censured and forced to describe her apology. At least some of their reporters are

on Twitter. But I think anything that sustains the attention on Iran is probably an effective strategy. I agree. It seems like the Iranian government is paying attention. Yeah, this is really a tech war. And I think one of the things I always say is repressive regimes, autocrats love the internet. They love this stuff because it is a tech war, all the tech stuff. The Iranians are cutting off the internet. That's a typical move of any of these repressive regimes. They're using video and location data to track down. There's always this flip side to all these things. Yeah, like food delivery services. Yeah. And then they have their own, you know, PR campaign on the internet and watching what people say and do. And that's very common, including tweets. There was someone arrested in Saudi Arabia because of this. So it's a very sophisticated war. And even though the protesters can use these tools too, the government has the upper hand here.

The internet is a tool of repression as well as expression. Expression as well as expression. It is, but this feels like a Gen Z protest, like a generation that will not give up. And I think we're even seeing, you know, we see that here in the U.S. Gen Z feels fundamentally different. Let's see what they can do in Iran, but we'll keep paying attention. We will. All right, let's take a quick break and come back for the interview.

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that Silicon Valley is full of like engineer CEOs, Elon Musk, Mark Zuckerberg, Sundar Pichai, Parag Agarwal, and commercial CEOs, people like Mark Benioff or Susan Wojcicki. And Brian is more of this artist designer CEO, which we saw with Steve Jobs. And I guess Adam Masseri maybe from Instagram is this technically. Like, Do you think that makes a difference? You've covered so many of these titans. Does that make a difference? I think he has a viewpoint. He looks up from his computer a little bit, and he has a sensibility of the world.

He surrounds himself with techies, but I think he does have more of a vision about what it is, and he's able to change when there are problems. And I think a lot of techies do dig in for some reason that they're right, and the numbers show this and that. And, you know, he reminds me, he's not, I'm not going to compare him to Steve Jobs, but Steve Jobs talked about the mix of art and science constantly or art and technology, mostly art and science. And I think he's right. I think the reason why Apple inspires so much as a technological product is because it has art in it. And same thing with Airbnb.

It's beautifully rendered. It's beautifully done. And it has a soul. The office is beautiful. Oh, my it. And same thing with Airbnb. It's beautifully rendered. It's beautifully done. And it has a soul. The office is beautiful. Oh my God, that office in San Francisco. They aren't going to it anymore. I know. But it's a beautiful place. It's a beautiful place. They spent a lot of money on it and that was sort of a waste of money now. But it's a different company. Now they've had their share of problems, you know, and lots of them, including fighting with cities, whether they're degrading cities, rentals, this and that. But he's- Yeah, push up from the hotel lobby.

Also, yes, yes, exactly. And I just really like him. And I liked him from the minute I met them. I met them, I bought them coffee, they didn't have any money, the founders in a coffee shop in San Francisco. And the idea was just so great, the idea of community. And I really, that very much appealed to me, the idea of community. And I really, that very much appealed to me, the idea of staying in other people's houses, not being afraid for people. And certainly there's been abuses. Absolutely. I'm not undercutting that. But they do move to correct when there are. And they're very thoughtful about it. And so the minute I really, really liked him was when we were, during that time when there was, people had, I think it was an orgy and

wrecked someone's apartment. It got tons of press. We wrote about it at our website. And this woman wrote a letter and they didn't fix it fast enough and they certainly didn't respond correctly. And then later they did. But I said, is this going to be a problem, orgies? And he goes, they've been having orgies in hotels for decades. And I just love that answer. I thought it was the best answer. It's slightly different to have an orgy in a hotel room and in someone's home, Carol. I understand. But nonetheless, it was so funny.

I didn't know that's what you meant by community. Yes, right. Yeah. Listen, I have no problem with orgies, as long as they clean up afterwards. Anyway. All right. Let's play the conversation with Brian Chesky. So I'm very excited to do this interview.

I like Brian Chesky, and I cannot say that about most of the people I cover. It's a low bar, Brian, let me just say. And you'll see your mothers here. Everyone say hi to Brian's mom. So we're going to talk about a lot of things. Let's start talking about remote work now. You and I have talked a lot about this at the beginning of the pandemic when things were going really badly for Airbnb,

and you had to do layoffs and really cut back in the growth that was happening. Since then, things went better for you because people were renting places and going to other places. What's the state of the economy from your perspective right now? I mean, certainly from where we sit, this is the most disruptive the economy has been since I started Airbnb with my two co-founders. And we started Airbnb in 2008. In fact, we launched August 2008. I don't think I could have picked a worse month to start it. August 2008. I don't think I could have picked a worse month to start it. That being said, business is going quite well. And part of the reason why is our model is pretty resilient.

So when the pandemic occurred, initially, we lost 80% of our business in eight weeks. And people were predicting- Because they weren't traveling. People weren't traveling. But then something pretty incredible happened. After months of people being stuck in their home, they said, I want to get out of my house. And they couldn't cross borders. They weren't traveling for business. They weren't going to cities. So they got in cars and they traveled like a tank of gas away to an Airbnb. And they started working out of it and they started working with other friends. So they started booking bigger homes, which meant revenue started driving up. And it was a incredible recovery for our business. And

we've seen a pretty large recovery ever since then. I mean, this business is now bigger than it ever was in the past. And most travel companies haven't recovered yet. So, but it's changed. Your business is totally different. It's not people going to France and staying somewhere. Now that's back to starting to come back. But like a really interesting thing is when we started Airbnb before the pandemic, 80% of our business was either somebody crossing a border or going to a city. Right. And now the majority of our business is something much different. More than a half of our business are longer than a week stays. And about a fifth of our business is longer than a

month. So it's a totally different business now. I mean, we're not just a travel company. We're kind of a travel and housing company now. Housing company. Yeah. I'll get to Adam Newman in a minute. But when you're thinking about what that means, how do you plan for that? So people are now with remote work. You had built a beautiful headquarters, which you had, is now what? It's still an office that people come in and, you know, I still go in every, like, well, every week or two. I go in for a couple of days. Right.

All right. But things are very different in terms of offices. So how do you plan for that first as a manager? And then also, what is the trend and how does it affect you if people aren't going into offices, if they're not living the way they used to? How do you adjust your business for that? Yeah. I mean, first of all, we took an approach

that was a little different than a lot of companies. You know, a lot of companies were rushing to return their employees to work. And I tried to take a step back and ask, how do I think employees are going to work in the future? And the inspiration I looked to was young companies. Because young companies 20 years ago, companies that were young 20 years ago, because young companies 20 years ago, companies that were young 20 years ago, popularized remote, like open floor plans, on-site perks. And I noticed something. All the young companies were much more remote. And then I thought to myself, where are all the talented people going to be in the future? And I thought, as much as there's a lot of talented people in Silicon Valley, the best people will now be everywhere. And so a company that limited its

talent to a community around his office was going to be at a disadvantage. So we basically created a number of principles. We said you can live and work anywhere, any of 160 countries around the world. If you move anywhere in the country, we're not going to reduce your pay. And we also are going to bring you together very intentionally about a week, a quarter. And so that's what we're basically trying to figure out now is how do we organize the entire company? And what I've learned is you notice all these CEOs like basically saying like, how do I know they're doing any work if I can't see them? Right.

Well, I think there's a, I think that's a bit of an old school way to think about running a company. So what we try to do is just get really organized. The more flexibility you give the employees, the more organized you need to be about what everyone's doing because you can't manage by walking around and seeing them. But you can track everyone's work online. And so I ultimately think that the future is flexibility, the best people live in everywhere, and that people are going to demand flexibility as much as compensation. And if you require people to live in your office, you're going to probably be at a disadvantage. Disadvantage, meaning they'll quit. Oh, big time.

Yeah. Big time. So they'll quit. Oh, big time. Big time. So they like that. They like that idea. But right now, a lot of people are trying to force people back to work. I think that's the word a lot of workers are using. But they feel like, I've talked to especially banking people, you know, tech companies have tried it. Apple tried it.

And everybody didn't work very well. Some people are trying to limit pay if they're somewhere else. If you live in San Francisco, you get more. If you live somewhere else, you don't. How do you look at that? You just said you're not going to limit pay. Most companies do location-based pay. So if you live in San Francisco and you move to Mississippi, it's got a cheaper standard of living, so you would reduce their pay. And for us, that was a little tricky because I was living on Airbnb. And so if I'm living in California for one month, do I get a different paycheck than if I go another month in Florida?

And it started to feel a little old-fashioned. And I made the, came to the conclusion that eventually wages at a national basis, at least for people that do jobs on laptop, will probably converge. And maybe over time there could be like a housing stipend. If you live in a very expensive city, you might get a little bump to live in San Francisco because housing is more expensive. But I ultimately think people are going to want to live anywhere. They're going to want flexibility.

And your paycheck changing based on where you're working is going to be a very odd thing. So that's the bet that we made. So we do one flat base pay if you live anywhere in the country. And the other thing we decided is we want do one flat base pay if you live anywhere in the country. And the other thing we decided is we want to create a model for other companies. So we are allowing people to live in any of 160 countries. Now, the problem with this, and the reason no one does this, is there's a lot of paperwork. It's a huge administrative overhead, and most HR, finance, legal departments

don't want to deal with this. So we said, well, it's in our interest that more companies do this because they'll stay in where it being these. So we're trying to make it really easy. I'm not going to lie. That's why we're doing it. You're a business genius. Exactly. Oh my God. He's amazing. Let's convince everyone to do this, make it really easy in the open source solution. So that's what we're trying to do. You're trying to do, which is to give, to limit the paper. It's another business for you. Yeah. I mean, what we're trying to do is make it easier for employees to be able to work anywhere in the world and for companies to be able to manage and figure out where... Without having to deal with all the jurisdictions. And if we can make it easier for ourselves,

we shouldn't make this proprietary. Why don't we open source it? And so that's what we're trying to do. All right. So when it comes to the business and when companies are doing this, you think it's going to be what you're doing more than anybody else, but for laptop-based people, not people that have to be... I think that if I could predict, I think like half the working population in the United States essentially probably has a job that is a laptop approximate job. So if you work in a hospital, you can't obviously do that. But I think this is where the world's going. And if you want to predict the future, look to what young people are doing, look to what next generation's doing. And so I think the common mistake people do is they look at what the most powerful people do, thinking the most powerful people lead the way in the future.

Well, most powerful people are usually old people. And old people aren't defining the future, it's young people. And so the old companies 20 years ago didn't define the future of the office. So why would that be suddenly true today? And so I think these older companies that are rooted in finance are probably going to be a little bit more legacy than the young companies. So what do you do then, though, with, I think, a legitimate idea of mentorship and, like, a law firm was asking me about this. They want these partners want to be able to talk to the associates and that the really smart ones will come in. That's what they said, essentially, the smart ones will come in, the more aggressive ones that we want. Is there a negative toward not having that, where everybody's, you know, in their little apartment, lovely Airbnb, here I am in Rome,

but you're by yourself, you're in these pockets. Do you see any? Yeah, and to be super clear, I think pure remote is probably not good. I think that forcing people back to an office five days a week or do some so-called three-day week hybrid is probably not great. It's probably not going to last. And you force people to do something, they're going to fight back. Five days a week, remote, never see employees. I think what's going to end up happening is, number one, people's circles get really small because you don't bump into anyone.

And then suddenly young people- Which is a good thing sometimes in the office. Sometimes it's a good thing. I don't want to anyone. And then suddenly young people- Which is a good thing sometimes in the office. Sometimes it's a good thing. I don't want to deal with all these people. Yeah. But if you're, I'm trying to imagine if I was 25 and I didn't have an office, suddenly my office is Zoom, the mall is Amazon,

the theater is Netflix. There's a scenario where people never leave their house. Yes. And this is, I think, long after the pandemic is over, there's going to be something that's going to probably kill a lot more people, which is the loneliness epidemic. We've talked about the Surgeon General of the United States who's dealt with COVID. His issue when he was Surgeon General for Barack Obama is loneliness.

Right. And so I think ultimately the best solution is to bring people together. But I don't think it's like three days a week. I think it's immersive, maybe a couple weeks at a time where you bring these small teams together. And I think that's probably what's going to end up prevailing. Well, I want to get your business thing, but loneliness. You and I talked about it. It was quite poignant. People don't know, Brian's been traveling the country. At the beginning of this pandemic, your mother showed up and wouldn't leave, right? And I think she just said you called her a squatter. Yeah. Is that

correct? Yeah, yeah, yeah. The good news is we have a lot of experience as squatters. So, but, well, I am, just to be clear, I'm 41. When the pandemic occurred, I was 39. And I remember when I was young, my mom was a social worker. And my dad was social workers. Yeah. Also a fundraiser. She wants to point out she was a little...

Now she's a fundraiser. But growing up, she was a social worker. And my mom said, I chose a job to love and I need no money. You should choose a job that pays you a lot of money. And so one day I got the idea that I was going to be an artist. And she said, you've managed to find the only profession that's going to pay you less than a social worker. And I said, no, I'm going to make money. And she goes, if you go to art school, you've got to make a deal with me that you're not going to be 40 living with me.

And then the pandemic occurred and then she moved in with me. And I not going to be 40 living with me. And then the pandemic occurred and then she moved in with me and I'm about to turn 40. And I'm like, oh my God, like on the one hand, I'm running this global company. Other hand, I'm living alone with my mom and I'm almost 40. And so it was, let me be clear. You're also a billionaire, but go ahead. Yes, yes. There's that. There's that thing, but when you don't leave your house, you don't really notice it. I woke up, I wore sweatpants. My mom ultimately would be making me quiche every morning.

So it was really a great team. I feel like she helped us go public in that way. And everyone's got their role. But at some point, I decided I got to branch out. I got to get on my own now. And so I ended up getting a golden retriever puppy. Her name is Sophie Supernova because she's got more energy than a collapsing star. And at the beginning of the year, I like to... You're such a geek. Yeah, exactly. I can't believe you're single, but go ahead. I know. Can you imagine? Yeah.

single, but go ahead. I know. Can you imagine? Yeah. And so now I lost my train of thought. Okay. So I'm living with mom. I'm living with mom. And then all of a sudden I see all these people are living on Airbnb and I like to dog food the product. And I thought, why don't I try this? And so Sophie and I hit the road. I went to like half, maybe a dozen cities the first six months of the year. You interviewed me in Miami. I was living in, I was staying in an Airbnb there. I went to like half, maybe a dozen cities the first six months of the year. You interviewed me in Miami. I was living in, I was staying in an Airbnb there. I kind of, I went to a Frank Lloyd Wright house in Ann Arbor, Michigan. I booked this house in LA at Laurel Canyon and it said fairytale cottage. That's what I thought I saw. I got to it and I misread it. It said fairytale princess cottage. It was all pink and had a child's bathtub and that's all it had in it. So I actually did bathe in that and I hadn't taken a bath since I was eight.

So, um, yeah, so you kind of learn a lot of things, but I did learn a lot about the experience by living in Airbnb. What did you learn? What did you, besides baths? I learned a lot of things, but I'll just highlight one. The cleaning fees are too high. We'll get into that in a minute. The cleaning fees are too high.

I know, I know. Oh, my God. There's going to be a... Just, you know... Thank you, everyone. Thank you very much. Good night. Good night night just dog fooding it just well i will say yes after looking okay well let's come to cleaning fees but let me but i will promise to talk about cleaning fees because they're a popular topic on twitter and elsewhere um so what i noticed is i didn't have to be anywhere like a lot of people. Like in other

words, like a lot of people travel because they have a business meeting or they're like, I've always wanted to go to Paris, but I could go anywhere. And that's when we realized why does Airbnb only have a search box? If since 1994 with the advent of Expedia, everyone's asked you this question, where are you going? And so people only type in the same hundred places. And we wonder why you go to Paris and there's tons of people in Paris. Well, they can't think to type in a small town in France, never heard of it before. And so we decided to change our entire search product. And that's when we created Airbnb Categories, where you can still search, but you can discover things based on whether you want to stay near golf courses or vineyards or tree houses,

et cetera, et cetera, et cetera. And that's just one of the things we did. So that made a big difference. Where was your favorite place you stayed? Probably I stayed in this house. So we have a category called design and it's by notable designers and architects. And my favorite architect was probably Frank Lloyd Wright. And I found this home called, I think it's the Palmer House in Ann Arbor, Michigan, built in the 1950s. And that was unbelievable. I mean, when you're in a Frank Lloyd Wright building, any building, it's almost like you're in a cathedral. There's like a spirit to every one of the structures. And did you stay

with people? Did you just, did you do things by yourself? Or it just feels like the plot of like one of those things where the prince is pretending he's not the prince coming to America. But did you stay in places? They definitely knew. Most people knew who I was. I didn't stay. I don't think any of the properties, I stayed with people on the premise with me. But I was pretty upfront about who I was.

Because you've done that. You've stayed in. Oh, yeah, yeah. Actually, in 2010, it was even more of a serious situation. We ran out of space in our office. Our office was a three-bedroom apartment. One room was an office. Then we moved into the second room.

And pretty soon, I turned my bedroom into a meeting room. And I didn't know where to live. I went on Craigslist looking for housing. I thought, why don't I just live on Airbnb? And I ended up going place to place in 2010. Then in 2000, I think 19, I did it again, where I lived on Airbnb, staying in different homes in San Francisco, trying out the product. And I ultimately think like, if you make a product, you want to use it yourself. The problem is you were working all the time. You have a travel company. It's sometimes hard to use your product. So you got to try to find ways to do it.

And you've stayed in all different kinds. And I going to get to the cleaning for you in a minute, but I want to talk about your business because most tech stocks are down significantly. So talk about the environment for tech right now, because everyone I talk to is like losing money all over the place and things are more problematic. How do you look at that? You know, I think out of crisis comes opportunity, and maybe I'm an optimist. We've had a 10-year or maybe 12-year bull run. But again, when we started and you met me early on, I remember one of the first venture capitalists I ever met, it was 2008. We set up a meeting probably in July.

By the time we had the meeting, it was maybe August, September. So the economy crashed. And at one point, the investor told me, the economy is so bad, we can't invest in good companies. Why would I invest in airbed and breakfast? It was literally airbeds back then. And so it was pretty humbling. And we couldn't raise money. And so because we couldn't raise money, we had this like scrappiness. We had this constraint. And I think one of the things that happened, one of the challenges that Airbnb had is I think we probably raised too much money. And I think a lot of companies raise too much money. And I think there's this narrative in Silicon Valley that cash is king.

You need as much cash as possible. I think people should think of cash like food. A human can die of under eating. They can also be unhealthy if they overeat. And if a company has too much capital, they don't make hard choices. They pursue things for too long. They shouldn't. And they have a lack of constraints and a lack of discipline. And so I would say this is an opportunity. This is an opportunity for people to reset their culture. But the other

thing is bad economies are where major shifts in behavior happen. I don't know if Airbnb would have worked had it not been for the recession in 2008. People were willing to change their behavior. So I guess what I would say is this is a storm or it's an investment nuclear winter, so to speak, but that might be an opportunity. And I think many of the best companies are founded during recessions,

partly because behavior is willing to change, but also because- But you're not founded, you're a big company. How do you do that? Will you have to lay off more? Oh, as far as right now? Yeah. Well, we already, obviously, as you know,

we already did all that in 2020. And so it was incredibly painful. We lost almost half our employees. And we did a layoff that was 25% of our employees. But then when you do a giant layoff, a lot of people quit after that because they're like, well, I think, you know, Airbnb is not going to be doing very well for very long.

So we lost thousands of people. And in 2020, I remember, you know, we put our IPO on hold. Our banker, one of our bankers told us, I don't think you have to think about that for a couple more years. That's what he said. And then all of a sudden, our business just ricocheted back, but without so many employees. And I did not want to make the same mistake again. And so I said, after we lost thousands of employees, I said, we're going to be very measured about rehiring people because I don't want to have to go through this again.

And so we've been really, really lean. Even during the pandemic. Even during the pandemic. And a lot of people did overhire, I think. A lot of people overhired. Amazon is now going to be doing that. I think a company should hire more than, with rare exceptions, if you're big, you should be careful hiring more than 10% to 20% of headcount a year. And we were planning on only hiring like 7%. And a lot of companies are growing like 40%. And so a giant company adding 40% of the people is a total shit show. Like, I think that's a really bad situation.

And then you end up overcorrecting. Everyone's like, okay, go free for all. So we just stayed really measured. We were really disciplined. And it was such a lean team. It's like thousands of us got in a foxhole. And I realized that we could do so much with so little, so many fewer resources than we ever imagined. So you don't need to suddenly rename your company like Meta or anything like that.

We don't need to do that. Yeah. Yeah. Although you didn't kill democracy, just issues around neighborhoods. No, I'm teasing. But let's talk about those controversies. One of the things I do like about Brian is when there are controversies, he doesn't hide away. He will address them with you. I have not talked to Mark Zuckerberg for years after he told me Alex Jones should be on Facebook, which I disagreed with him. This was three or four years ago. But one of the things you've had is this idea of nimbyism. Where is that now? You were having problems with cities. You, of course, pay taxes.

You shifted around. How do you look? Do you think your company continues to, it's a very different story. Everyone's moving out of San Francisco, so they're not mad about people making money from it. And you, of course, are trying to make money for the people who own homes to make more money. Do you still worry about the impact of Airbnb on neighborhoods, on communities? How do you think of your role in that? I still worry about it, yeah. And maybe I can just back up, Karen. We've talked about this. When I came to Silicon Valley in 2007,

the word tech might as well have been a dictionary definition for the word good because it didn't seem threatening. And every piece of technology is step forward humanity, hence you were making the world a better place. And we were all platforms and platforms are a little more hands-off and a platform should be like an immune system. And I think that we've all learned lessons that that's not the case, but I think we learn lessons sooner because we got scrutiny. We learned 10 employees. And so like the moment we had 10 employees, the New York city, we had issues. And so I think it was hard in our DNA that when the internet moves into your neighborhood, people

will speak up. I think it was a rude awakening and a wake-up call. It was a wake-up call to me that we, large companies, have to take responsibility. If you're a platform and you give power to hundreds of millions of people, they're going to use it for things you could have never intended. You have a choice to decide that it's not my responsibility or I can lean into the responsibility. And we decided to lean into the responsibility. So I hired this woman, Belinda, she became our COO. And I used to think when people don't like you, you should avoid them.

And she told me, no, if you don't, if somebody doesn't like you, you should meet them. You should like, it's because it's hard for people to hate each other up close. And I started going on this like listening tour. I felt initially like a hate tour. Everyone would tell me about what I'm doing, but we learned a lot. And the first thing we learned is, okay, like they want us to collect taxes. And we built this portal to be able to collect or emit taxes where we've now collected three or $4 billion in taxes. The next thing cities said is we don't want people taking housing off the market. So we said, well, how do we know if they're taking housing off the market? They said, well, let's have them register. And we'll like in San Francisco, this registration process, you have to live here

275 days a year. And so we now have agreements with thousands of cities, but I still, do I worry? Yes. One of the things I've learned is whatever I don't worry about becomes a future problem that I'll have to worry a lot more about. And you can either be early and do more as expected, or you can be late and you have to do 10 times more than people expect and it's never enough. And I think the problem with Silicon Valley is it's so data oriented that really like data oriented people tend to not think something's a problem until it's kind of too late because there's no data. Like people don't like seeing around corners, but I tried to anticipate. And so, yeah, we tried to make sure that we're strengthening neighborhoods we're in

and we're working with cities. So what's the problem you see now? What are you worried about? The impact that Airbnb is having. Well, the most obvious thing that I'm concerned about is a small town becoming so popular that if we could have a harmful effect on a big city like San Francisco,

and I don't think it ever had a huge effect, but it could have an effect, the smaller the city, the more it could be concentrated. And so there's a number of ways to try to solve this problem. You can try to limit the nights. But one of the things we did was categories. What we're trying to do is point demand to where we have supply so that too many people don't go to one location. And so that's really part of the big motivation of categories. If you have a search box, everyone hears, oh, everyone's going to like Tulum. So everyone types in Tulum and then suddenly Tulum's got too many people. And so if we can tell people, well, you should go to like this place or that town, a place you never heard of, that to me is maybe the ultimate solution. percent of the work week is spent communicating, typing, talking, and going back and forth

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So when you're thinking about Silicon Valley in general, you are different than other people. There's a couple of people. I think Evan Spiegel is quite thoughtful, thinks about things. How do you look at where everyone is? Everyone moved out of San Francisco. We're going to Miami. We're going here. We're going there, taking their money and going. How do you look at where tech is going as one of its leaders? And just, do you mean like the whole industry?

Yeah, how is it like here? Because they're not, people aren't living here. They're not, there isn't the same community. There's not. Yeah, wow, that's a great question. I'm optimistic. One of the reasons that we decided to allow remote work was because I thought it would increase diversity. San Francisco is not the most diverse city, but no city can be perfectly diverse. It's never as diverse as the whole world. In that moment that you allow flexibility, suddenly ideas and companies can emerge from anywhere. And I think the challenge

with Silicon Valley is it's not been really diverse. And I'm not going to, like, I'll just give my lens on diversity. I went to art school. When I was raising money in Silicon Valley, I remember one of the venture capitalists said, we love everything but you and your idea. They said it nicer than that, but that's what they meant. And they meant that this idea of strangers seeing people's homes is crazy, but a designer can't run a tech company. I couldn't code. I was a designer. And I think that there's many issues with a lack of diversity in Silicon Valley. And one of the problems is a lack of humanities. You know, let's take like, let's take any trend, Web3, the metaverse, all these things. We're in this theater, right? This theater was designed by architects.

Architecture is a field that's been around for thousands of years. So we've had thousands of years to understand good and bad principles. and artists and scientists all come together to build this. When you suddenly are replacing a building with a digital space that only engineers are building, they're building it quickly. They didn't go to school for this. There's not hundreds of years of histories and lessons. It gets a little dangerous because you don't know the consequences of what you built until it's huge. And once that happens, it can be a little bit late. And so I think one of the things that's really important is we must marry artists and scientists, designers, people in humanities from all walks of life to come together. And I think we need to slow down a little bit. I think there's this race that if the world's fucked up, let's

build the new world as fast as possible. And maybe just occasionally, we need to slow down a little bit and ask, well, what was wrong about that last thing we built? And how do we imbue the lessons into the next thing? And so I'm optimistic. I was a little bit concerned about the Web3, not the idea of Web3,

but the like frenetic, like get in before it lasts. And I think that's not totally healthy because who builds responsible things that quickly? You got to slow down. I don't think responsible was the top of mind. I think get rich quick was, I believe. Just my feeling. Exactly. Well, that's one of the lessons I learned because we as CEOs, we have multiple stakeholders, whether we choose to acknowledge them or not. But when you're a tech founder, you often think of just one stakeholder, your investors. And what do investors

want? They want graphs that go up and to the right. But even like the problem is, let's say you achieve your goal. You're going to achieve a goal where you're so big, the world hates you if you don't think about the world. And so this is a very dangerous lesson. And I experienced a little of this. We grew so fast. We were a billion dollar company. And then this is a very dangerous lesson. And I experienced a little of this. We grew so fast. We were a billion-dollar company. And then all of a sudden, attorney generals were subpoenaing us. People were saying we're having ill effects in their neighborhood. And it was a bit of a growing up experience for me. And we want to not make the same mistakes twice. So we're trying to be really responsible this time around. Okay. Let's talk about two more things.

One is, speaking of responsible and growing up, what do you think about what Elon Musk is doing around Twitter? But he's been a little noisy about various things, including explaining to all of us the foreign relations of Ukraine. I don't have, yeah, I'm not going to try to negotiate anything. Right now? Not right now. You probably do a much better job, I should say. How do you look at that? Do you mean the Twitter deal?

The Twitter deal, the whole thing. Maybe all of them? Both, yeah. I'll talk about both. Okay. I understand that Jack wanted Twitter to be an open protocol. The way I experience that is like a telephone or HTTP or email. I think the reality is Twitter is,

that train has left a station, it's a community. And I think that if you want to own Twitter, you have to say that you're in the community building business. And if you want to be in the community building business, that means that you have an excitement and passion about the nitty gritty of all the different stakeholders. And I think this is beyond just free speech or any of those issues. I think this is beyond just free speech or any of those issues. I think this is about how do you manage hundreds of millions of people to have meaningful conversations?

And like one of the things, one of the first principles of the community and tell people what you stand for. When you log on Twitter, there is no, they don't tell you that we're about free speech or about healthy conversations. You don't know what it's about. And so people are bringing their ideology to Twitter. We learned the hard way. So we said,

Airbnb is not about discrimination. So we make you check a box saying you're not going to discriminate. And guess what? Millions of people said, I'm out of here. But at least people knew what the rules were. So I think he's in the community building business. And I hope he knows that. I don't think he does. I would say on Ukraine, because I have not a lot of experience brokering peace, but I have some experience in Ukraine. I think it's really important.

Here's my view on the whole thing. I think that every one of us as companies, big companies with a lot of responsibility, when an international conflict breaks out, they should ask a simple question, how can we help? And I always wanted to believe that if I was a CEO during like World War II and the giant war broken out, we would have been helpful. And so when Putin invaded Ukraine, we asked, how can we help? And it's an obvious way. We have 6 million homes. So the way we can help is by offering housing. And so within four days of the invasion,

we announced that we were going to provide housing for 100,000 Ukraine refugees for free. And I made that commitment not knowing we'd ever hit it. I actually financially, personally backstopped a lot of it because I just didn't even want to have time to go to the board. I said, you know what, we have to be fast. I'll backstop if this becomes very expensive. And something remarkable happened. Tens of thousands of people opened their homes, and we've now housed more than 100,000 Ukraine refugees. But something even... Thank you. Something even more remarkable than that happened. People around the world started booking Airbnbs in Ukraine.

Homes they never intended to stay in just to send them relief aid. And within a couple weeks, they had sent $23 million to people in Ukraine. And I think there's a lesson here. And the lesson, I think the video even covered it, is in a world of darkness, in a world of despair, kindness still exists. And so to bring this back to Elon in Ukraine, I think the lesson I took is every one of us should focus on our superpower, how we can help,

and that's what we should be focused on. And I have no competency in bringing world leaders together, so I'm not going to be- So you're not talking to Putin, right? I have no competency. I world leaders together, so I'm not going to be. So you're not talking to Putin, right? I have no competency. I'm not doing that. Okay. You did that also with Charlottesville and other things like that.

Do you think CEOs should walk away from these controversial topics, whether it's don't say gay, whether it's whatever it happens to be at the moment? How do you decide which one of those things, like what not to do? Because you've waited in quite a bit compared to us. We've waded in quite a bit, but obviously we don't wade in everything. The general approach I've taken is if it's something around our competency,

like when Trump did the travel ban, we're like, well, we're a travel company. We know a lot about travel and travel bans. So we stood up, we even did a Super Bowl commercial and I didn't know what the consequences of that would be. And so I've tried to lean in as much as I can to certain issues and just be authentic. What does this company stand for? What are the values of this company? And we have an opportunity to demonstrate them each step of the way, but we can't wade into everything. So there might be a certain issue, like let's say immigration will be helpful,

but we don't have a unique competence in immigration. So we don't weigh in too much in that, but I generally believe it's a good thing. So we'll be helpful. But when it comes to many other issues, we're going to lean in pretty heavily. Okay. Two more last questions. One, you and I last spoke in Miami, actually, and we talked about loneliness and you talked about your own personal loneliness quite a bit. I was surprised by that are you still lonely yeah a little bit um I mean I'll I told you this in Miami but I'll

I had this image in my head that we would one day have a huge company, and I'd be surrounded by all these people, and everyone would love me, and I wouldn't be lonely. And I think a lot of people want to be successful, and I think a lot of people sometimes want to be famous because the idea of fame is that all these people love you, and you're not going to be lonely. because the idea of fame is that all these people love you and you're not gonna be lonely. I'm not saying I'm famous, but even in my own little way, that's not love, that's adulation.

And love is something so different. It comes from meaningful connections and you don't need to be successful to be loved. You don't need to be famous to be loved. In fact, you can't be loved, you're famous because how could they possibly know you? And I think some of the most lonely people I know are the most successful people that I know. And I think that success and money actually has this pernicious way of potentially isolating you. And by the way,

the richest people fly private, they go to private things, and they don't really interact with regular people. And when they travel, rich people, when they travel, like they bring the world with them. They don't integrate into the local culture. And so I've tried to push really far against that. But yeah, I'm 41, living a golden retriever. But I've been working really hard to like not isolate myself. And, you know, I probably thought when I was younger that by now, I don't think I ever thought I'd have a multi-billion dollar company, but I probably thought I'd have a family.

And things went in a different order than I expected. But I think this idea of loneliness drives me because I think that this is one of the loneliest periods in human history. And isn't it funny, the more time we spend on screens connecting with people online, the more lonely people become. There's something interesting. No one's ever changed someone else's mind in the YouTube comments section. Your Instagram followers aren't coming to your funeral. We need to have real connections in the real world. And the more time we spend on screen, sometimes that becomes an obstacle to that human connection. I would agree. I would agree. You know, I was talking to someone, it might've been Mark, it might have been Elon, and I had disagreed,

and they're like mad that I disagreed with them, because I'm disagreeable, you know that. But they were like, well, no, nobody says that. And I go, everybody works for you. You pay everybody, including your family, sorry to tell you, you know what I mean? You pay for everybody. I'm your best fucking friend, you know what I mean? And I don't really like you, not you, but at least I'm telling you the truth. And it was really interesting because they get surrounded. You watch the show Succession. One of the things that they do very well is how everything gets smaller and more comfortable, but smaller and smaller and smaller. And so they're in these insular worlds, very hard to break through. And that's where when you start to

challenge them, they think you're terrible for doing so. All right, last question. That was great to talk about. Cleaning fees. Yes. What a great way to end. And that's the last question. We're way over, but cleaning fees. Brian, come on. What the fuck? I agree. And let me just tell you, while you're answering that, I rented from one of, I'm turning 60 in December, and I rented the Jerry Lewis estate in Palm Springs. I'm looking right now, but I'd like you to answer that question, and then I'm going to find out. Go ahead. Go ahead. Go for it. Are you looking right now? I'm looking right now. It's right here, Palm Springs. This is going to be great.

Where's the price? Okay. It's probably a big house, so it's going to be a little... It's a big house. I have a lot of children, unlike you. Yeah, isn't it amazing? I have a gold retriever. Yeah, whatever. I've got like seven pets.

What are you talking about? All right. It doesn't say... Oh, my goodness. Get to see. It's probably really great. It All right. It doesn't say. Oh, my goodness. It's probably really great. It's probably not too much. Yeah. Oh, here we go.

Cleaning fee. Oh, wow. Okay, that's not bad. What is it? Okay, but there's a service fee. What's that? A service fee pays to keep the website going. And it's only 12%.

So that goes to you, right? Well, Airbnb. Okay, there's a cleaning fee of $350. What's the price per night? I'm not telling you that. It's probably a huge house. I have like 100 children. So that's $350 to clean up after 100 kids.

I'm turning 60. I'm spending the money here. What do you want? That sounds like a really big house for me. Yeah, it is. You can come. And I didn't stay in the house. If you're lonely, spend time with my family.

Okay, let's get the cleaning fees. I would like to be lonely, but go ahead. Exactly. So cleaning fees. It's a huge be lonely, but go ahead. Exactly. So cleaning fees. It's a huge problem. We want to fix it. One of the things about cleaning fees is we never intentionally designed this. They happened organically over time.

Hosts wanted to basically recoup their costs. They wanted to have a fixed cost. They didn't want to amortize overnight. And it just got out of control. And I think it got specifically out of control in the United States. The cleaning fees in the United States are two to three X that in Europe. So we basically brought a team together and we said, we actually have to fix this top to bottom. Part of it is showing upfront pricing, but there's a lot of things we're working on. One of the things is we want to create a variable cleaning fee. So if you have like 10 kids,

you're staying for a month, that's probably a bigger cleaning fee. If it's a single guy, the golden retriever for three days, that should to create a variable cleaning fee. So if you have like 10 kids who are staying for a month, that's probably a bigger cleaning fee. If it's a single guy that's going to retrieve her for three days, that should probably be a lower cleaning fee. So we want to also help hosts understand how much they're charging. A lot of hosts have no idea what they're charging. So there's really like, it's not just one thing. It's like 10 or 15 different things. And money touches every part of Airbnb. But we're going to have some updates coming in the coming months, some pretty big ones.

I'm taking a really holistic approach to cleaning and cleaning fees. And actually I'd like a customer to never see a cleaning fee. So we do want hosts to be able to say, I need to add this fixed cost. But when you go to Airbnb in the future, I'd like you just to see taxes

and ideally nothing else. And that's where we want to get to. All right, everybody, Brian Chesky. Thank you. So, Kara, after he opens up to you about his loneliness, you're waving your hundred kids around him in his face. What are you doing, Kara? That is not very nice. Not very nice. His mom was there in the audience and we talked about this. We were very interested in getting him a nice family. She lived with him during the pandemic.

I know he mentioned, but she made him quiche. That's so nice. I think he called her a stalker. She just entered her, or a squatter. He called her a squatter. Squ he called her a stalker. You know, she just entered, or a squatter. He called her a squatter, not a stalker. Very different character. I just, I want him, I like him. I like him. I want him to be happy. It was interesting when he was speaking about being lonely and the kind of culture of screens

and time on the internet making us lonely. I was wondering, look, I grew up moving around a lot. I, you know, I've been nomadic much of my life. I've been what I call millennial homeless, where I'm living between two or three cities at the same time. And this view that he's articulating of people living everywhere, but kind of nowhere, I think that has a loneliness potential too. It does. Just the way screens do. And I think that that is something that's like Instagram and social media have made it really admirable. Like

I'm, you know, I'm quitting my job. I'm living between these different cities. I'm doing this. And there's a real loneliness in it. There is. Whenever young people tell me that I want to work at home, I'm like, oh, that's not, not because you need to be in the office or you need mentorship, but both of which you definitely need the latter. But that it's, it isolates you. I was joking with Brian afterwards. I really appreciate him articulating that loneliness. Some days I wish I was lonely. I just don't feel lonely very much. That's why you're in San Francisco right now. Far from your children. I was talking to my wife, Amanda, after that. And I said, I got to spend some time in San Francisco,

some real time in San Francisco. And she goes, yeah, we all can. And I go, no, alone. Alone. I want to be alone. I know. Everybody's got a problem. I think it's not just the work connections, though. I lived in 12 cities in 12 years before settling in New York a few years ago. I think it's just grounding. It's grounding and the ability to have a launchpad for life. You can always retreat, but it's hard to ground, I think. Yes. All right, Cara, last but not least, Brian Chesky agrees with me on Elon and that he should stay in his lane when it comes to Ukraine. Are you still not budging? Have you changed your

mind? I don't care what he says about it. I don't care. Cara. All right. Well, Elon is not calling the 1-888-CARA-PLZ line for our advice, but someone else did. Let's move on to the Ask Cara segment. I think this question is about dating, by the way, continuation of a theme. Kara, I just heard your advice on today's pod from the woman from California who wanted to know how you share your opinion so confidently. I am also confident enough to share my opinion, even though I'm not an award-winning journalist or top-ranked podcaster. My confidence came from much work that I've done to understand my worth and value. Now I'm 64, long divorced with grown children. Here's my dilemma.

I want a romantic partner, though I don't need one. I can't seem to find men who are comfortable with my confidence or who aren't in the market for a caregiver. I've done most of the dating apps with a modicum of success, but those apps no longer have much appeal. I've joined lots of the dating apps with a modicum of success, but those apps no longer have much appeal. I've joined lots of groups to meet new people, but still run into the same issues I noted. What do you think? Should I get a matchmaker?

If so, how the heck do I find one? Oh, my God. That is a tough one. I have not ever used a dating app or, you know, I'd say become a lesbian. It sounds like you're straight, though. There's lots of great ladies out there. But, but don't, please don't do that. Do whatever you want. But I'm saying that would work. You know, I unfortunately think a lot of women, especially as older is they are in that situation where men don't like women who have that much

confidence or you do become a caregiver because women do live longer than men or tend to. And so it's really hard. I think it's hard to find a romantic partner. I think you either date younger. That's a way to do it, to date much younger people. I think that can happen. The other way is to create a group of friends around you. I know that sounds wrong, but I think a lot of people do have these groups around them, even in their middle age and as they get older, where it's a support group of

people, men and women around you that you have significant relationships with. I suppose a matchmaker might work. I've heard a lot of people have had success with that. I don't have any idea how to found them. I've never used apps or matchmakers. I've not really joined groups or gone to bars. I don't drink very much. I just tend to meet people. So I don't really have good advice here. Naima, do you have anything to say? You're a big dater. Big dater. I've dated a lot in my times. You date a lot. That makes me sound like I'm okay. Well, my advice, I think it's just my advice is kind of, oh, there you go. I've dated more recently than you. And I have used some apps and I've been

approached by matchmakers. I think that you should keep on, I think you should do the things that you enjoy doing and be open to the idea that someone might surprise you. And in the meantime, I think, ask your friends to set you up. Ask your kids to set you up. It's like a parent trap. Do a parent trap situation with the kids. No, come on. Are you a twin with an equal twin? No. Well, whatever.

Not the parent trap situation. But, you know, I do think kids have a good sense of you. Your friends have a good sense of you. You know, hey, I think parents could actually set their kids up pretty well, Kara. I agree with you on that, but not my mom. Anyway, anyway, good luck to you. Good luck to you. I just think you have to think more widely, as both of us said, in different ways. I think you have to think more widely and just be, not be looking for things, be just live your life and see where it goes.

I love your advice, Carrie. You're like, I don't go to them. They come to me, the dating market. What can I say? What can I say? All right, let's get some credits in, please. Today's show was produced by Naeem Araza, Blake Neshek, Christian Castro-Rossell,

and Raffaella Seward. Special thanks to the team at Lesbians Who Tech and specifically Leanne Pittsford. Rick Kwan engineered this episode, and our theme music is by Trackademics. If you're already following the show, you get a lollipop. If not, do you want a lollipop?

You cannot have one unless you follow the show. Go wherever you listen to podcasts. Search for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from hit follow. Thanks for listening to On with Kara Swisher from New York Magazine and the Vox Media Podcast Network and us. We'll be back on Monday with more.