Now, at the time, Jason, we were trying to raise $150,000 at a $1.5 million post-money valuation. So, for $150,000, you could have owned 10% of Airbnb. And the majority of them didn't even reply to the email. I actually ended up publishing a bunch of the rejection emails, but many people said like, "This isn't a good idea." Many people said like, "Travel, we're not like excited about travel." I remember one investor said, "We love everything but you and your idea." In other words, I'm like, "Well, everything else is good." Unfortunately, I thought to myself, "Wait, what else is there?

There's me, there's the idea." The logo. Yeah. I guess there's the name. They didn't like the name either. This Week in Startups is brought to you by Lemon.io. Need to speed up your product development without draining your budget? Hire vetted engineers from Europe at Lemon.io. Go to Lemon.io/twist to get 15% off for the first four weeks.

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While you're there, get an extra 10% off using offer code TWIST. All right, everybody. We've had all the legendary startup CEOs on This Week in Startups over the past decade. Daniel from Spotify, Travis from Uber, Toby from Shopify, Brian from Coinbase, Tony from DoorDash, Melanie from Canva, Slootman from Snowflake.

But man, I have been wanting to interview the founders of Airbnb, which is just one of the great companies of all time, and certainly in the last two decades of startup companies. And I've been able to have both founders now on the program. We had Joe Jebbia on episode 1675, and today his co-founder and the CEO of Airbnb, Brian Chesky, is with us.

How are you doing, Brian? Hey, good. Great to finally be on, Jason. Good to see you. Yes. We've been trying to get this on for a while, and we finally did it. Congrats on the great performance. Thank you. So, last quarter, things have been going great. I think big picture, when you look back on the last decade of running this company, there were really two meaningful companies that came out of this last cycle.

After Facebook and Twitter, you had Airbnb and Uber. And I'm curious, I know the Uber story, obviously, up close and personal, how that was accepted by the investment community and the hurdles they had to get over to want to be in that business. Uber, famously, had a lot of resistance to the concept of Airbnb, and now massive consumer acceptance.

So, when you look back on your journey, everybody telling you, "This is crazy. It's never going to work." And then everybody, when they see you, saying, "Oh my God, I love Airbnb." How do you reconcile that as an entrepreneur? We came up... Obviously, I know Joe told the founding story, but I'll tell a little bit of the...

There's a founding story, and then, Jason, there's a story of all the rejection. The first time we came up with the idea, it was October 2007. It was for a design conference that was coming to San Francisco. There was an after-party at the Fairmont Hotel. We went to the Fairmont Hotel.

The first person I told about the idea, he looks at me with a straight face. He said, "Brian?" I said, "Yes." He goes, "I hope that's not the only idea you're working on." That's what he said to me. And this was like a design luminaire in our industry. And that was kind of the general sentiment.

I remember in January, February 2008, Joe and I were living in San Francisco, it was an apartment. And we had a roommate named Phil. And Phil worked for this company called Justin.tv. Justin.tv was a precursor to Twitch, and it was funded by this program called Y Combinator. Now, I didn't know anything about Y Combinator.

I didn't know anything about Silicon Valley. I didn't even know what angels were. Somebody once told me there are these people called angels. And I said, "Oh my God, this person believes in angels." So, I was really naive. I didn't know anything about Silicon Valley. I was a designer by training.

And Michael said, "I can introduce you to these angel investors." And so, Michael introduced us to 10 to 20 angel investors. Now, at the time, Jason, we were trying to raise $150,000 at a $1.5 million post-money valuation. So, for $150,000, you could have owned 10% of Airbnb. And the majority of them didn't even reply to the email.

I actually ended up publishing a bunch of the rejection emails. But many people said, "This isn't a good idea." Many people said, "Travel, we're not excited about travel." I remember one investor said, "We love everything but you and your idea." In other words, I'm like, "Well, everything else is good." So, I thought to myself, "Wait, what else is there?

There's me. There's the idea." The logo. Yeah. I guess there's the name, but they didn't like the name either. And what they meant by they liked everything but us and the idea was, it was three founders, one software engineer, and two designers. And they thought, "Well, you have too many designers in your founding team." People just associated designers as non-technical, and therefore, maybe not adding value.

And I always felt like Joe and I, our ability as being designers, was actually part of the secret sauce of Airbnb because it was not a pure technology problem. And also, people said, "This is crazy. Strangers never say they're strangers." So, basically, no investors will invest in this company.

Everyone rejects us. It's now the fall 2008. We had just provided housing for the Democratic and Republican National Conventions. You know, Barack Obama and John McCain were running for president. The airbeds weren't working. We were renting out airbeds. They weren't selling. So, we thought, "Let's go with breakfast. We're airbed and breakfast." And so, Joe and I ended up creating this collectible breakfast cereal.

These boxes of Cheerios that we called Obama-Os, the breakfast of change. And then we bought Cap'n Crunch. And we read that John McCain was a captain of the Navy and we called it Cap'n McCain's, a maverick in every bite. And it seemed kind of crazy. We made these cereal boxes and we actually printed and like made $30,000 worth of cereal boxes that we sold.

And you know those baseball card binders that kids put, those binders that kids put? We used to put credit cards in them. In other words, we funded this company with tens of thousands of dollars of credit card debt. We used the cereal boxes to get us out of debt.

But now, it's like October 2008. We've been working on this idea for like a year. At some point, my mom said, "Are you a cereal company?" And technically, I think we were. I didn't want to admit it. I guess we were cereal entrepreneurs, but not the right kind of cereal entrepreneurs.

And I remember I was with, out of desperation, Joe and I went to dinner with Michael Seibel. And Michael Seibel, he had co-founders Justin Kahn, Emmett Shear, and Kyle Voight. Emmett runs Twitch, Kyle Voight runs Cruise. And we went to like a Thai restaurant in San Francisco. And it was like towards the end of the year.

And we're like brainstorming what to do. We were kind of screwed. We're like, everyone said no to us. We have no traction. We're selling collectible breakfast cereal. Everyone thinks this idea is no good. No one wants to fund like two designers and an engineer. What do we do? And then Justin says, "I have an idea.

Why don't you apply to Y Combinator?" And we're like, "But we already launched. Why would we apply to Y Combinator?" And they're like, "Because you're dying. You have no like growth." And so, we go on the Y Combinator website and we realize that the deadline was the night before.

In other words, it had just expired. We couldn't wait for another batch. Oh, by the way, Jason, the financial crisis you remember had just happened. - Sure. - One investor, I'm not going to lie, one investor told me, he said, "The economy is so bad, we won't even invest in good companies.

You think we're going to invest in air bed and breakfast and unproven concept people stand with each other?" Oh, and one other story is that Joe and I went to University Avenue. We met an investor who I won't name. He orders a strawberry smoothie. He then sits down drinking the strawberry smoothie.

Never picked his head up. In my first interaction with an investor, I'm like, "Maybe this is what they all do." He goes, "Uh-huh, uh-huh, uh-huh, uh-huh, uh-huh." And then within 10 minutes, he like leaves and I thought like he had to park his car. We haven't seen him since though.

- That's hilarious. - So, at this point, at this point, we're like these bad news bears of Silicon Valley. We were like rejects and Justin Conn, we're at dinner and they're like, "Oh my God, you're totally going to die now because like you can't get into Y Combinator." And then Justin Conn says, "I'm going to email Paul Graham." And he ends up emailing Paul Graham and he goes, "Is this deadline definitely, definitely over?" And Paul Graham says, "I will extend it to midnight tonight." It's like 9 p.m., okay?

- Yeah. - But they have to apply by midnight. Now, Joe and I are in San Francisco. We have a co-founder named Nate who's an engineer. He's in Boston. Now, it's like midnight and Nate kind of doesn't sleep past, I think he went to bed. So, I told Joe, I said, "Okay, we'll divide and conquer.

I will fill out the application and you will convince Nate, you're going to wake his ass up in Boston and convince him to do Y Combinator if we get in." So, he calls Nate, apparently, he goes, "Nate's in," I'm like, "Great." We fill out the application, we submit it.

Then a week later or whatever, we get an interview and then we tell Nate and I think Nate's like, "Wait, what? What did I agree to? I agreed to like move to San Francisco?" So, you know that movie "8 Mile" where like Eminem, he's like, "You got like one shot?" - Yeah.

- This was kind of it. This is like our one shot, right? - Yeah. - So, we like prepared for this interview like crazy and we were warned, this is going to be like a 15-minute interview and they're going to ask you four questions at the same time. And you better know every answer.

And Justin and Michael and Emmitt said like, "Just know your numbers inside and out." So, we basically did like rehearsals. We almost recreated like NYPD Blue or like we throw a phone book in each other's faces. - Yeah. - And we were just like, "We better get this sh*t right." So, we go to Y Combinator, we go to the interview, it's exactly what I expected.

It's Paul, it's Jessica, it's Trevor Brackwell and it's I think Robert Morris. And they're all like basically, they all ask us questions at the same time. Like all four of them. And I was like totally bewildered. And the first question Paul Graham asked me is, "People are actually doing this?" And I said, "Yes." His second question was, "What's wrong with them?" And the interview at that point went downhill from there.

He, midway through the interview, he basically tried to get us to create Stripe. He's like, "You should create this like payments company or like an online bank or something." And we're like, "That seems like a really good idea." But like, we have an idea. And we're about to leave the interview.

It doesn't seem like it's going well. And Joe takes out a box of Obama O's and he hands it to Paul Graham. And Paul Graham's like, looks like he just got a novelty gift. He's like, "All right. Thank you." - Yeah. - And Joe goes, "What's the story?" He goes, "This is how we funded the company." And he goes, "What do you mean?" He said, "Well, we told him the story, how we like made the cereal boxes.

And then the way we sold the cereal boxes, we mailed them to reporters and they put them in their newsroom desk and everyone would buy them." And he said something like, "I guess if you can convince people to pay $40 for a $4 box of cereal, then maybe you can convince at least some people to stay in each other's homes." And he ended up admitting us to Y Combinator.

And I guess we've never looked back since. I also want to give credit to Jessica, because I think Jessica thought, I remember Paul and Jessica said later, they thought we were like cockroaches. And I think they mean it in a good way, that it was like an investment nuclear winter.

And in a nuclear holocaust, the only thing that survives are cockroaches. And the only thing that would survive an investment nuclear winter would be the founders of Airbnb. We said, "We won't die no matter what happens." And so they basically funded us because we seem Brazilian, unkillable. And like, even if the fundraising market was dried up, we would just go on.

So it was definitely not a story to glory in the beginning. And I like to remind founders of this, because then when we got product market fit three months later, we got funded by Sequoia. And so in a three-month period, we went from like, kind of like this untouchable company to Sequoia.

And if you were a part of Sequoia, so you'll remember 2009, I would say it was like, it's I don't know, it's like going to like an Ivy League school or something. But it meant something, it was a real seal of approval and it was crazy. And you were anointed basically, if Sequoia invested in you, that was like, okay, seal of approval.

This is a legit company. And I think it meant even more than not because Sequoia was more prestigious than but because there wasn't a much capital than like, I just, you know, I don't, you know, this industry better than I do. But I don't remember hundreds of people I could contact to get money.

They're really angel list. I don't think existed. Or I just get it was venture list at the time. I always do it like my open angel forum, they were like, maybe you could make a list of maybe 25 angel investors in the valley. And half of them said no to us already.

So clearly, and we raise money, Jason, our first actual round, which is a series A was and this is when we had product market fit, we were voted by Y Combinator. So each batch, they rate like the best company like halfway through and at the end, and we were rated the best.

We had the most traction. And then then we raised $615,000 at a $3 million post money valuation, credible with product market fit $3 million post money. It's crazy. And you just like look at the signaling at that time. Yeah. It's so weird. Like people had these ideas like, oh, well, the only way it's going to work is if you're from Stanford, you're from RISD.

Like what is that like? Yeah. And one developer and two designers? Yeah. makes a difference between two developers and one designer? Yeah. Obviously, these are not the material things. All that matters is the customers. And do they engage with the product and actually get some value. And that's what you figured out was, you don't need to appeal to everybody.

There just has to be somebody who gets value from this. Exactly. And there's a group of people. Yeah. That's a great lesson. Michael Sabe used to tell us to me, I used to tell Jason, Michael, I said, my sister won't stay in Airbnb because initially, when I first came to the idea, she said she wouldn't do it.

And he said, you don't do cares about your sister. She's not the early adopter. You need the early adopters. You just need enough people to get the flywheel going. Everyone else will come later. So focus on those people. Yeah. And you think about his first hand experience with Justin TV was like, Justin TV was called Justin TV because there was one person who was insane enough to record their life.

Yes. Exactly. Yes. Then it became Twitch. And now here we are, there's 10 million people streaming and like you turn on TikTok and there are people who are working in China, like cooking and they're on a live streaming like what is happening in the world like people are making a living just live streaming themselves cooking in a restaurant halfway around the world.

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Yes. And now becoming a public company, growing at the pace you did having to deal with regulation and there's a lot of blocking and talking and tackling and operational stuff. I'm curious how you spend your time today as CEO of the company. Because in just over the last decade, every time I talked to you about Airbnb on Twitter, or I mentioned Airbnb or something I like about it, you're instantly in there responding and thinking about product.

And so I'm curious, how much of your day are you on product over time? How is that change? And how do you stay so focused on product versus doing your chores, which as a public company, there's a lot of chores that come up? Yeah, it's a great question. I would say I spend almost all my time on product, marketing, and hiring, those three things.

And product and marketing, I also combine, like a lot of companies, they think of marketing as like advertising and product as product development. We actually have a function, we took it from Apple, product marketing, where we tie, we basically try to make sure product and marketing are joint the hip.

Think of product as the chefs, marketers the waiters, and a lot of companies like the waiters can't go in the kitchen, they get yelled at. So we really try to make them integrated. So here's how we run the company. The entire company is a functional organization. So we have an engineering group, a product marketing group, a design group, like ops, you know, legal, HR.

So most every other company is divisional or subdivisional. The entire company is on one single roadmap. So I mean, yeah, there's accounting systems that maybe aren't, but basically anything you ever see is on one roadmap. Most companies have separate roadmaps. And then we do these release cycles. And we basically do a giant release in May and a giant release in November.

So basically, the idea is that we try to basically take the best of software development, and the best in hardware development, and put it onto one practice. And the reason why is I found that the way people develop software, which is great for 10 people, where you basically democratize data, you decentralize, and anyone can ship anything and it feels very empowering, and it feels it can go really fast.

That's great until you're like 1000s of people. And then everyone is basically a free for all. They're all hitting the payments platform. There's no cohesive roadmap. As you subdivide the company, ideas get smaller, you don't even know what to market. And then you can't keep track of everything, then there's like no accountability.

And so and then lack of accountability becomes politics and bureaucracy, all this weird stuff. So when the pandemic occurred, out of basically Jason's survival, we lost 80% of our business in eight weeks. And Joe and I and Nate, we were like, what the hell do we do? And we were like staring into the abyss.

I mean, you might remember people were making predictions like is this the end of Airbnb? Will Airbnb exist? And one of the people I was talking to a lot back then was Johnny Ive. He now works with me. But he told me the stories of Steve Jobs going back to Apple.

And when Steve Jobs went back to Apple, you know, they were like 90 days from bankruptcy. And I'm like, well, that seems kind of like, you know, Airbnb is in a very precarious situation. And Johnny Ive said, you know, you can cut but you can't cut your way to the growth.

Steve, you have to build product, you need to stay in the product. And I hired a guy named Hiroki Asai from Apple, he was also instrumental. And so I totally changed how I ran the company. So what I used to do is I was very hands off, I democratize data, I was very much reactive, I thought my job was like strategy and capital allocation.

And here's the weird thing, the less hands on I was, the more I got sucked into problems. And when I by the time I got sucked into a problem, it was like 10 times as much work. So then I decided I'm going to do something different. We're going to be totally integrated, one roadmap, I'm going to do very few things, and I'm going to be involved in every single detail.

And Airbnb is not going to do anything more than I can personally focus on. And that what became the governor. And this is what Steve said at Apple, he said, well, we want to do more things than I can focus on. Now, this sounds like it would slow us down.

And initially, it did slow us down. Because I would review everything. So I had these things called CEO reviews. And every single project in the company, I had a program management function. And I would review everything either every week, every two weeks, every four weeks or every quarter. And then we track the progress.

And then you know, then everything would ship on a single deadline. Initially, people hated this, no one wanted to collaborate, people didn't want to have imposed deadlines on them. They were wondering, why are you meddling? Like, why are you reviewing all the work, but eventually, it created a culture.

And I was trying to teach a sense of quality, I was trying to be like the editor or the orchestra conductor. And eventually, what ended up happening was, we were able to like start shipping faster. And in the last three years, we've shipped 340 upgrades and innovations. And we obsess.

I mean, a lot of companies, they're just trying to grow. And they look at their dashboard, they have these sub teams looking at growth, they're doing A/B tests. And I don't like that process, the process of just chasing growth. Because first of all, you're not really solving customer problems.

And if you're over reliant on A/B testing, and you choose B, do you know why B worked? Because if you don't know why B worked, you're stuck with B. And you can never redesign B because you don't even know why B was better than A. And so, we decided, if you're going to do ERF experimentation, you better know why B worked better than A.

We're going to be qualitative and quantitatively driven. And so, what I do is, I spend most of my time just reviewing work and hiring people. So, I review all these different things. And I don't really spend a lot of time on corporate matters anymore. And the reason why is because once we designed the company, like, it became very efficient.

We also don't have a lot of employees. We have like 5,300 employees. And we did three and a half billion dollars in free cash flow last year. So, you can just think about that. - That's incredible. - For every dollar, we do 40, 42% of 42 cents in free cash flow, which I believe is higher than Google or Apple.

Now, obviously, we're not nearly as profitable at absolute dollars, but it's very efficient. So, we try to be like the Navy SEALs around the Navy. It's a small, lean, elite group. It's super intense. It's kind of day and night, to be honest. But I'm honest about it. And when people come to join, I probably try to talk people out of joining more talking them in.

I'm kind of like, "Are you crazy? Like, why do you want to put up with all this?" And it really tries to set a mindset that when you come here, this is a really intense place, but hopefully, it's going to be really gratifying. And we're really connected, the top 30, 40 people in the company.

And I think of it as like one shared consciousness. Does that make sense? - Yeah. - So, it's one shared consciousness. I don't push decision-making down. I pull it in. I don't make the decisions on my own. There's like a group of us, a concentric circle that like kind of just are in constant conversation.

I don't do strategy reviews. I do this thing called living with the strategy. Instead of doing like a three-hour, that's like what boards do. They get like a deep dive. I talk about it every week until we resolve it. So, every week, we'll have like, "What are we going to do about this topic?

What are we going to do about this topic?" Until the answer reveals itself. And I think this way of working is trial and error. I've tried all the other ways of working and they didn't work. And I think this like bottoms up, like giving tons of people a lot of discretion.

It does work when you're small. When you get big, it becomes a free-for-all. And I think a lot of big companies are paying the price. - Yeah. And the prioritization gets lost. What I like about, "Hey, here's what I can keep in my brain," well, that also parallels what a customer can keep in their brain.

- Exactly. - They can only handle so many new features at a certain velocity. And if you give them 20 things, they're going to remember two. - Exactly. - And probably not more than that. - And that's what happened. Years ago, we had, so we have one marketing department now, and they only market a few things a year.

And the things we market, you probably know about because we try not to say anything you don't know about. - Upfront and clear pricing was the last one. - Exactly. Yeah, exactly. And today, we promoted Airbnb rooms, and we promoted that there are a whole bunch of things people are angry about, or they don't like about Airbnb, and we've made 50 fixes.

And so we did that. But I remember- - And before that was Experiences. - Yep. Experiences. We launched Airbnb Categories a year ago. - Oh, yeah. I remember that too. - And Air Cover, which is this really important thing for hosts and protects them. But years ago, at one point, we had 10 divisions.

We had 10 marketing departments. And it was so crazy that one time, I asked the marketing department, "Get a conference room and put every piece of marketing on the wall." It took them a week to track down all the marketing because it was 10 different teams. I'm like, "If you can't track down everything we're saying," and then I went around the wall and I said, "It feels like I'm looking at 10 different companies." And I didn't even know 80% of the marketing we were doing.

I mean, we were doing, we had different creative agencies in different countries, and it was just incoherent. So what we do now is we just do a few campaigns. We don't do local campaigns. We trans-create, but we only do global campaigns because it's a cross-border business. And we just try to be incredibly simple.

Steve Jobs had a saying, "Marketing is education. You speak to the customer the way you talk to an eight-year-old." Not down to them, but they're busy. You have to explain things simply. If you can't explain something simply, you don't understand it. And so every type of communication we try to do, we try to do to somebody who's not really paying attention, they're busy, and they don't have time and say, "What's the most basic idea we can communicate?" Yeah.

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I mean, any big company has this. And I think Doug had it as well, which is, it's just too many people working on too many different projects. There's no cohesiveness. And then quality goes down. And then the consumers are like, am I supposed to buy a Pixel or some other Android phone?

Am I supposed to use Chrome operating system or the Android operating system? Which one is going to win out here? And then I'm a consumer, I have a Nest, and then I have Google Home. And just that one cognitive dissonance I have, like where I open up Google Home to see all of my cameras, and I open up Nest to see the old cameras.

And I like my Nest better, and it's just chaos, right? And Sundar's got to be in the middle of this, trying to referee it, and if he did the same approach. And I don't want that life. I had that life before the pandemic. And I said, I don't want that life.

I don't want the life where I have to ask permission to get involved. I'm adjudicating disagreements, I'm managing bureaucracy and dysfunction. I want to be in the product with people making the product. I want to be talking to customers, I want to be communicating with them. And I want as little bureaucracy as possible.

And that requires us to do as little as possible. There's an old saying, have few details and perfect every detail. And that requires focus, it requires you saying no. So, we probably say no now more than we say yes to things. And I think that's pretty important. - Yeah, the second business line really was experiences, am I correct?

- Yes. - It was stays and then experiences. - Yes. - And is there even a third business line? - No, no. It's really just, you know, probably broadly like there's stays, 80% of stays are short-term, 20% are long-term stays defined by longer than 30 days. So, that's kind of like an in-between, it's an extension of the core.

And then experiences, which has been kind of like in an in-between zone because it was, we thought it was going to break out before the pandemic and then we had actually shut it down or pause it. So, it's, we're in a process of we're going to reboot that and we do, and just to be clear, we have some big ideas coming.

We have some really huge ideas that I think will expand Airbnb way beyond travel, way beyond our core. It's going to launch next year. But I'll tell one more story, you know, I feel like companies, you know, like there's certain companies you like root for them, like a lot of people love their Tesla car and they like want Tesla to come out with a truck.

A lot of people love, in 2006, how many people wanted Apple to come out of the phone? A lot. And the reason why is we all loved our iPod. How many of us love, wanted Gateway to come out with a phone? Probably not many. And so, I like to tell people, we have to have permission by the customer to do something new.

And we only have permission to do something new if they love what we currently do. And if they're complaining on Twitter about upfront pricing, about having to do chores and they check out, about customer service taking too long, then we don't have permission. They don't want to do something new because they're going to think we're going to bring problems to that category.

So, I told the team, I said, "We have some big ideas, AI is going to unlock so many of them, but we don't have permission to do new things until people love our core service. So, we're going to basically create a blueprint of every single thing people are complaining about." So, we created this storyboard of the end-to-end experience.

Then I got basically blueprinted out with the team, all 150 screens on the app, every user policy, all 72 user policies. Now, each of these user policies are as many as 100 pages long, right? Like who gets a refund, when. And imagine, Jason, you're a call center worker, Airbnb just hired you.

Now, like two customers in different languages are in a dispute and you're adjudicating between 70 policies that are as many as 100 pages long. That's a perfect example of AI. Anyway, this is an opportunity where we realized, okay, we created this blueprint and then we mapped tens of thousands of social media posts, millions of customer calls, and all these interviews with customers.

And we put them on the blueprint. We looked at what is everyone upset about? What do they want fixed? And based on this blueprint, we were able to go stage by stage in the end-to-end journey and prioritize the top issues. And we said, "We're going to get through every one of these issues before we do something new." And that was the whole premise of today.

It was basically fixing what people wanted. And then we had one more thing. We're like, "We got some unfinished business." This idea of people staying with each other in their homes, the original idea of Airbnb, that's kind of like the Volkswagen's Beetle or Nike's running shoes or Apple's iMac or whatever, the original car, original product.

I said, "We got to revive that. We can't. We got to get back on the highway and we got to reinvest in this core idea before we do new stuff." And so, that was kind of what today was about. And hopefully, if we're successful, people feel like we listened.

Let's talk about the user complaints and prioritization of them because how do you know when you're running something at scale like this, that this is something that's annoying but necessary. You can't throw a party in an Airbnb. I had my old home, which I was thinking of keeping, and I had an Airbnb.

And only one time in a year was there a party thrown there. You guys handled it great. There was a little bit of damage. Insurance picked it up. But over and over again, it has in the documentation, do not throw a party here. Do not throw a party. You can't throw parties.

So, how do you know when something is like, you know, just this is a deal breaker for people who are hosts. This is a deal breaker for people who are going to choose a hotel or an Airbnb to run an Airbnb or not run an Airbnb as a host.

And these are like minor annoyances, but they come up frequently. So, there's like a certain amount of suffering in each thing, right? And I'm curious how you prioritize the suffering to alleviate it, because you're also mitigating and arbitrating between these two groups of people, the hosts who can't be burdened so much that they don't want to be a host because it's arduous.

And then the people who are leaving the home who don't want to have to do an hour of chores when they leave. Like, it's reasonable to put the dishes in the sink, but do you have to mop the floor or take out the garbage? Okay, maybe taking the garbage out is okay.

How did you prioritize that? It's both an art and a science. I think that analyzing it is a science and then prioritization is probably more of an art. I can explain. So, let's start with analyzing. The first thing we do is we try to just take all the inputs.

So, what are the inputs we get? Inputs are customer service calls. Inputs are social media posts. Inputs are we do like tens of thousands of like, we do listening sessions with guests and hosts. And then inputs are like basically user behavior, right? You can like see what people are clicking.

You can see retention. You can see when somebody churns. And then if there's a party, we don't handle it right, they churn, they don't come back. And then we see people in their network don't list and you can start to measure that. So, those are your inputs. Those inputs, you basically now have like an organization of like maybe millions of issues and you can bucket them to like say 100, 200 types of things.

The next thing you do is you look at the frequency and the severity. So, severity might be like a safety issue. Very infrequent, but when it happens, it's really serious. A frequent issue is like, I'm upset with a refund. Not as severe, but very frequent. That happens all the time.

And then you start to look at relationships like, you know, we notice a lot of hosts are complaining about pricing being confusing. A lot of guests are complaining that hosts are charging too high fees. And then we start to realize, wait a second, if we make it easier for hosts to price and they understand what guests are actually paying, they might actually do a better job pricing and guests won't complain as much.

So, you start to find like connections. So, this is where, that's the science part. Now the art part. Now it's actually picking stuff because you have a list. You have some matrix like severity, frequency, this and that. But the real ability is the art form of a group of us, 10 or 20 of us, deeply understand the issue so well.

We live the product, we use the product, I host, I've read thousands of things. You just take thousands of inputs, you put them in your head, and then you just go through and you can't paint by numbers. You can't be purely algorithmic is what I would say. That's why that's the art.

You could, but I think it's never as good as your intuition. But your intuition is formed of all these data points. And the intuition might be like, you know, it also might involve like engineering capability. Like this is going to be a really heavy lift, so we have like t-shirt sizes.

A small lift, medium lift, large lift, extra large lift. So, we'll prioritize high severity, high frequency, like low engineering lifts, for example, would be a great candidate. - Quick wins. - Quick wins. - Yeah. - That with high payoff. There might be a big lift, but we need to do it to launch this feature later.

So basically, there's like hundreds of inputs. You see how like you're like weighing all these in your head? And I think there is this, I think developing a product, the best products I feel like are a group of people that are deeply involved and they can hold a thousand contradictory things in their head.

And they can make all those different trade-offs. We call that intuition, but I don't know if I love that because it makes it seem like it's arbitrary and not systematic. It actually is very deep and it can actually be very technical. And so, that's what we do. I audit all the prioritization and I personally decide on the final prioritization of every single project and the company that a customer will ever see.

I don't decide, I mean, the final decision, I make the final call. And I only make a call if I'm informed. And I only am informed if my team understands. And so, I make sure that I know the details, my directs know the details, and their directs directs know the details.

I also have a rule that if I have a direct report in a meeting, they can never call their direct to answer a question. If that's the case, they don't know the details and their scope is too big. So I mean, within reason. So that's kind of how I do it.

And then we update it twice a year. So we have this thing called the Roadmap Review where we bring in like top 70 or so product people in the company or people weighing on the roadmap. We spend a couple days together. We debate everything on the roadmap, we adjust it, and then we roll it out.

And then we have an extremely robust program management function. Most companies ask product management to basically be their program managers. We separate product management with program management. And we have a very small product management function. It's very small. We have product marketers. Product marketers are senior product managers. So we have no outbound people.

You have to know inbound and outbound. The junior product managers don't need to do outbound. But then most of what people call product management, we call program management. And they're the ones keeping the whole thing on trains because everything has to fit together. And they're doing like really rigorous reporting every week about like where we are at the project.

So it's all integrated. And the net result of this, Jason, is I can literally know the performance of an individual engineer I've never met on a week-to-week basis. Because imagine if we're all designing a car, I know how good the tire team is doing when I see the car assembled every week.

And I see, hey, there's something wrong with the tire. But when there are like 100 different products, I don't have time to value 100 different things. Yeah. I mean, this is where constraint comes in. If you want to make great art, as you learned as an artist at RISD, like if you give some artist a thousand canvases and buckets and buckets of paint and a million brushes, like where do you begin?

Right? And how do you prioritize? And you just get lost. Creative people want constraints. And that's the other thing. And I think what happened, and maybe this is a burger lesson, Jason, in Silicon Valley is I think in the last 10 years, we as entrepreneurs in Silicon Valley probably didn't have enough constraints.

And it's kind of like we didn't ask for constraints, we didn't want constraints, but we probably needed them. I think that Airbnb before the pandemic probably raised too much money. And we didn't raise as much money as others. And I think that in hindsight, like not having as much money means you have constraints.

Constraints means you have to say no, you have to make hard decisions. If somebody is not performing, you can't just hire more people, you got to deal with it. And if a product's not succeeding, you got to actually fix it or sunset it, you know. So I think the constraints are really critical.

Listen, we work with super early stage companies at my investment firm launch, you know, pre Series A, maybe got a couple of $1,000 a month in revenue, you've raised a couple $100,000, maybe $1 million, right? That's the early days, year one or two of a startup. And I'll be honest, a lot of times startups, they don't have their insurance.

They haven't set that up yet. They haven't set up their accounting properly. They're getting things cleaned up. In fact, I was recently had a great startup, but they didn't have DNO insurance that basically protect your directors and officers. That's the D directors, people on the board, officers, the people who work at the company, right?

directors and officers insurance is super important. So what do we do? We sent them right to in broker or friends over to broker or a business insurance company that's built specifically for startups. You just fill out a simple application, right? And then startups get four quotes for four lines of coverage in 15 minutes, four quotes, four lines of coverage, 15 minutes, easy breezy lemon, squeezy.

That's right. They connect you with one of their expert brokers for unmatched service that goes beyond your policy. And listen, you might think, oh, it's too early to have insurance. It's not that expensive. It's not that complicated, because in broker makes it easy. So here's what I want you to do.

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The zero interest rate policy led to a lack of discipline and maybe you avoid difficult decisions. Like, hey, this divisions working out okay, but it's not great. Yeah, it's never gonna be profitable. And you watched Uber, you know, you guys had your media stuff you were doing for a little while, which you were passionate about, I remember, but like, at a certain point, it's about the guests.

It's about their experience, and how many different projects could Uber do? They were doing micro mobility. And that was interesting, but it was just such a minor, unprofitable piece of the business. They deprecated it, right? Yeah, exactly. People really want to get on scooters, like what percentage of people in what percentage of cities?

When you did this cycle, what do you think are the problems you solved that were the most rewarding for you? Because when you solve a problem, you immediately know. So when you say cycle, you mean which time horizon? Well, the one you just did, where today at the release, there must be things that you personally, as you did the prioritization said, hey, these three things, these are the big wins.

And now you put that tweet storm out with the images in it showing each one, which I love by the way, when you get it directly from the founder, and it's like, here's the image, here's what I was thinking. Let me know. How did the public's early response, your host's early response, your customer's early response to what you thought the top three things were versus what they think the three things are?

Yeah, so the things I prioritized was probably number one, anything around pricing. The number one complaint at Airbnb is that the prices have gone up. And we started as an affordable alternative to a hotel, and Airbnbs had become over time less affordable. And I think we just like, I mean, that in itself was a potentially zero interest rate kind of phenomenon.

And so, that was the number one, it was like pricing transparency. The second one I focused on, because I just was so tired of hearing about it and I didn't want people to deal with it, was checkout chores. There was this, you know, turn the lights off and you'll leave is totally reasonable.

Strip the bed and put the sheets in the laundry is not reasonable, you're on vacation, like, and especially if you pay the cleaning fee. So, that is not reasonable. So, that was the second one that I really prioritized. The third, and this is more on the opportunity, is monthly stays.

That's a growing part of our business. People think of us as a travel company, but 20% of our business is now housing. And Airbnb, there's a lot of problems with monthly stays. For example, you can only pay by credit card. Paying your rent with credit card means you have to pay a credit card processing fee.

So, we thought, well, what if we allowed an integration where you can pay by bank? We did integration with Stripe, and now you can save a bunch of money paying by bank. You can now pay in installments. We now lower the fees. We now have this really cool little dial.

We now have really cool pricing discount tools. So, hosts can be encouraged to charge less and will promote the very best listings. So, these are maybe some of the ones that I was probably most passionate about. Anything around pricing, anything around chores, anything around really expanding the definition of Airbnb.

But yeah, there were 53 upgrades that we made. So, there were a lot of things. That's incredible. Yeah. And running a remote company, you're so thoughtful about how you're running the company now, and then you have constraints. It seems like you've got it really dialed in. Yeah. And listen, the stock market is responding to it.

The stock market is looking for discipline. I think you were the first of the cohort to actually show it. Uber just showed it. They started hitting free cash flow. Dara's done a great job there. And we're starting to see this discipline. And Zuck actually got religion. He cut 20,000 people and got rid of layers of management.

How is, when you are a remote company and you try to institute this, are these things in sync still? Or do you miss being in the same place with each other? Or do these retreats that you're doing and these offsites, whatever you call them now, are they enough? Or do you think at some point you want to be in an HQ again?

Yeah. Actually, yeah. So, probably, actually even good to clarify, we're not a so-called returned office company or a remote company. I would say Shopify and Coinbase are probably remote companies, as far as I can tell, last I checked. I go to an office every week. And many of my top people go to an office every week.

And we have offices open, and we welcome people back to the office. But we don't require people. We say, "You work wherever the hell you want because we're so disciplined, so organized that we don't think there's going to be a hit to productivity." I basically came to the conclusion that, especially with the accelerating rate of technological progress to AI, increasingly, you're going to be able to have more and more of a global talent pool.

And so then, if you're going to require people to come into an office, you have to believe that you get a greater productivity gain by having them physically there than the productivity gain you have being able to hire anyone anywhere in the world. And for some jobs, like your core team, where it's really creative and you're making stuff, I think you want to be physically together.

But I do not need our accounting systems to be managed together physically around me. I don't need thousands of people physically around me. I can't even talk to them. After about 1,500 people, I can't remember the conversations. I can't keep track of those conversations. So my vision is that we have a small, tight team of some of the most senior people, many product people.

We built this creative studio, and we're in San Francisco a lot. And then the rest of the company, they can choose. Some groups, they do come to the office. Other groups, people just work totally remotely. And then once a week, a quarter, we try to bring people together. Sometimes it might be a week every six months.

And I think that kind of suffices for a lot of people. In other words, we kind of give teams the option. But the most senior people, we're pretty much together. We also travel a lot together. So I'm here in New York. We probably had 20 people here with me.

So I was around them. But I think we're just still learning. We're still moving. And I think, Jason, the future is flexibility. I think that this is the worst technology we'll ever be in our lifetime. As screens get better, as bandwidth gets stronger, I think people are going to want more flexibility.

And my prediction is even proponents of working in the office, I bet you a lot of those people are going to be somewhere else over the summer in an Airbnb. You know? Yeah. It's easy for people to be like, "Yeah, we will." All these rich guys in New York, let's just be honest, all these rich guys in New York who said they want to call back to the office, they're all going to Hamptons for the summer, and they're going to Europe in August.

So even the return to office, those aren't 12 months a year. Those are now nine months a year. Yeah. And I mean, Europeans have a better lifestyle and they enjoy it. So maybe what happened during this pandemic, when we look back on and we do the post-mortem, it's going to be, "Hey, you know what?

Maybe Americans, we were slaves to the offices a bit too much. We over-indexed on it." And maybe there's some balance because when you do take a four-week vacation and you work half days for two of the weeks, you kind of come back refreshed and you stay with the company longer.

You don't resent your company and you're not depressed because you feel guilty about not spending time with your kids or not checking the bucket list items. And I think you're so right about the speed to hire that talented person versus the annoyance of somebody quiet quitting, or somebody's phoning it in, or somebody's working two jobs.

Like, of course, you're going to have abuse in every system. There's abuse in people who come to the office, screwing around with their door closed. So you're going to deal with some level of, I don't know, bad actors, whatever. And I kind of feel like if you want people to come to the office, it should be because of collaboration, it should be for trust building.

It shouldn't be for accountability. We have enough tools digitally that actually, it's frankly easier to track people when they're working digitally than they're in the office because you can actually track everything they're doing and you can just have really good mechanisms like what did you get done today? Yes.

Actually, we have a whole program manager operation whose job it is to basically tally what everyone's doing. And if we don't know what you're doing, then we're not doing our job. That's I think, why people are so, some of these managers are so aggressive about this is because they don't actually know how to manage.

And so since they didn't know how to manage, they were managing by the fear of being in the office and the punch clock as opposed to, did you assign the right person to work and did you check the work? Yeah. And checking the work and assigning the work is a lot of work and prioritizing, as you just said, your biggest challenge as the founder is just keeping all this in your head and trying to make the right decision on behalf of the customers.

And so many managers are phoning it in. I came up with the simplest system possible for my investment company, which was at the end of the day, have a cup of coffee and share with the team what you're going to try to accomplish. And when you check out for the end of the day, like make it a good checkout so you can go spend time with your family and just say what you got accomplished, if there are any blockers.

And when people just started doing that in the slack room, it was such a big difference. It was such a big difference. And then when somebody left the company, you know, we did we looked at their end of the week, and what they said they got accomplished what they were working on.

And we said, Hey, here's the last three into the weeks, we put it into one document, who should do this job? Should this job be retired? Should it be spread across three people? Should it be outsourced? You can actually look at the granularity, like you're saying, when they do digital work, it's all right there.

So then you can say, does this position need to be here? Or should it be outsourced or automated? You keep bringing up AI. And I'm curious, when you start, what are you seeing in AI right now that's getting you excited, internally running the company, and then externally in terms of opportunities, because travel is such a rich, textured experience, it's also so customized.

So you know, so much about your customers, you know, when I'm in Japan, you know, my trip to France, you know, the different places I've Airbnb'd, you know, who came with me. And, you know, whatever else, you know, about the hosts and everything. What do you think the opportunity is going to be in travel, specifically for AI?

Yeah, so let me let me, if you may indulge Jason, I'll like zoom out and just give you like kind of my mental model. And you can tell me if this maps to yours. So you have like the base of the foundation, right, the base models, which are basically the large language model.

So of course, GPT-4 is probably the preeminent base model. Google has some base models, Anthropic has a base model, Microsoft Research has their own base model. So you have like three to five big base models. I think of those base models as if it's like a highway, they're the highway, they're like the infrastructure.

And, you know, in another generation, by the way, that probably would have been dealt by the government, right? It's almost like the Manhattan Project, these large language models are going to be eventually about $100 billion supercomputers running these models. So they're going to be like massive, these are giant infrastructures.

And we're not going to do that. We don't do infrastructure. Airbnb, we think of ourselves as designing the cars on the highway. So on top of the base model, you have the tuning of the model. And the tuning of the model is going to be as good as your sensibility and your customer data.

So if you and I both ask Chachi Pitya a question, we mostly get the same answer. And we mostly get the same answer because it doesn't know who you or I am. And that's great for some questions, like what was the like, you know, like, how far is the moon from the sun or whatever?

Like there's one right answer. But if you ask like, where should I travel? Your answer and my answer are probably different. And so some problems are search problems. Some problems are kind of matching and personalization preferences problems. And so what we want to do is we want to be one of the best companies for AI personalization.

So we want to develop really good tuned models. To do that, we have to change our business. And actually, one of the questions that Johnny Ive told me when we brought him on the team is he said, you need to switch from beyond, you need to go beyond where and when.

Right now, you ask, where are you going? And when are you going? And we need to shift to who and what, who are you and what do you want? And that's really the vision. And so what we want to do is we want to build these robust profiles, I want to start to learn Jason, who you are, build really good, rich customer information.

And then I can understand and personalize, like, where do you want to go? And also, what do you want in your life? Like you looking for inspiration, just get out like a, you know, what do you what are you looking for? Do you like want to get healthy? Do you, you know, and you start to learn about people.

And then we're also pretty good interfaces and the application layer. And I think that Airbnb, that's where we're really, really going to focus, we're going to focus on the tuning of the models, the most personalized AI interface, and then really good application interfaces. Now I think as far as interface, I don't think they're all going to be just text based.

For example, we were working on the open AI plugin, we were one of the first partners that was working with open AI. And at the last second, I pulled the plug on the plugin. Because I just didn't like the interface. I didn't think that was the right way to interface a travel.

I told Sam, I said, long text outputs are low bandwidth. And then you give me another text output with widgets at the bottom, I said, I want something much more multimodal, more visual, richer. And if you're going to have access to GPT-4, why don't we put it in our app.

So we pulled the plug on the plugin. And we think eventually, I think our real vision is Airbnb, at the largest sense, isn't even a product or service. I hope it's more like a travel community. We're really building a travel community. And then the role we have the app in the travel community, is eventually we're like the ultimate like AI concierge, right?

We're like the ultimate host, like Charles Eames, one of the greatest in our 20th century said, "The role of the designer is that of a thoughtful host, anticipating the needs of the guests." So that's what we should do. And we understand who are you? What do you want? Where do you want to go?

And maybe we could even go beyond travel, if we get there, right? And the part of that means you have to trust us to give us your personal information. It means we have to be a marriage of art and science. It means we have to understand a lot about like human psychology and know what you want.

It's not just a technical problem. We have to design unique AI interfaces that are probably richer than just text inputs. Because you know, like, you want to see and feel things, right? And I think it's much more immersive. So that's where I think it goes. That's like the long term vision.

In the interim, and that's probably long term is in three to five years. I mean, that's not even that long term. In the next year, what we're going to do is three things. One, engineer productivity or productivity. I mean, I think engineers can be 30% more productive in the next three to six months.

- It's exactly the number I can put with. I'm watching my team interview founders for investment. I'm looking at due diligence. And I'm looking at my own behavior. And it seems like one out of three tasks, I can offload. And so I'm like, this is like this year, 30% more efficient, which means headcount stays the same, but we just added a third more people like this is unbelievable.

- It's amazing. And by the way, it's actually if everyone's 30% more productive, it's actually more productive than adding 30% more people because you know, the mythical man month, every time you add somebody they bring up communication and like, like bring attacks with them. So this is like productivity without the tax of more people.

And I think the productivity doubles, you know, in somewhere between one and two years, it's a little hard to know, but it will be double. So we'll have the equivalent of twice the engineers without the productivity tax. And so that's the first thing is just getting everyone on the tools, give everyone a co-pilot and getting everyone like just immerse.

And I just bang the drum, like use these tools as much as you can. I don't want to be like the Luddites or like afraid of a computer in the 1980s, right? Like we want to be using these tools. - That is so key. I told everybody to make chat GPT for their homepage in their browser, so that every time they open their browser, it just reminds them, hey, use this.

And I said, searches is obvious. But when I told you they do, they're like, hey, here's what I'm going to accomplish today. And here's what I'm going to accomplish at the end of the day. I just told everybody, try that in chat GPT and try a plugin. And by the way, when you were talking about plugins being like not exactly the right modality, I've been using OpenTable, Expedia, Kayak the last couple of days for travel, trying to see if it works.

And it's not as good as using some of the other like native interfaces yet. I mean, I'm sure it'll get better, but I agree that it needs to be visual and it's got a long ways to go. - OpenAI is a choice. They can either invest a ton on the interface layer, or they can decide that they're the brain and other people decide the interface.

Either way it can work. But either way, the interfaces, here's the thing I'd say, do you remember when like the iPhone launched and Steve said like, the problem with most smartphones is the bottom half of the screen, the interface doesn't change? I think that we should think of every task as wanting a distinct interface.

Like you have a hammer to get a nail in, you have a screwdriver for a screw, you have a spatula to scoop something up. Every interface should be custom designed exactly for the task. - Do you think it's voice for travel or do you think it's flipping through videos that are TikTok style and then understanding which ones people spend more time on?

- I don't think it's voice. I think voice is for commodities. So if you basically say I need to go from here to there, and there's no inputs, there's no decision making or visual discretion in voice. I think it's more like, I don't want to say like minority report, but I have this image of like, it's an immersive interface where it's words and images, and it's a conversational bot, but it's not pure text.

It's got lots of rich visuals, videos, photos. It's a little hard to describe. I have to build a prototype. - I haven't seen Minority Report. He puts on a pair of gloves, which MIT was working on at the time, and he's just moving stuff around in a virtual desktop.

- That's conceptually what I'm talking about. - Yeah, I think it's actually a pretty brilliant one because if you think about the function of magazines, which is how people did this previously, you flip through a magazine, what would you see in a magazine? A subhead, a headline, a table, an infographic, a picture, a two-page spread, a table.

And all of that was evocative and kind of pulled you in, and I actually really think with this vision of trying to understand me as a person, psychologically and where I'm going next, oh, Jason's doing more skiing, oh, he's got a bucket list of places he wants to go skiing, ah, he's really into food, and that trust you've built up is interesting as well because I would have no problem authenticating with Instagram and giving you all my photos, and with AI, you could just tell from my photos that I take pictures of a lot of food, and I take a lot of pictures of skiing.

You now know a lot about me, and I don't have to tell you, you just know my Instagram account. - And I think the problem is all of us, and Airbnb is part of this problem, you come to Airbnb and it looks the same as it did the last time you came, and we're like a marketplace, and everything's a transaction, and we assume you're like, we don't know anything about you, and you just walked into a store, and we got a bunch of stuff on a shelf.

And I think that's a very 1990s, 2000s Amazon paradigm of commerce, and I think the future of commerce is more like somebody showing you around, and they understand you deeply, and you have so much more control, and it's significantly more personalized, and everyone has a unique experience. And so that's where I think it goes, and I think that we don't have a search problem in the future, we have a matching problem.

So we are gonna use AI to match you to whatever you want, and I think that, the other thing is, I think we're gonna be really good at hopefully identity authentication. You know, the problem with AI is, what's the first word in AI? Artificial. The biggest risk before machines come after us is they become us, and we can't discern who is a machine and who is not.

And I think that we're already seeing that. I mean, when that Pope photo circulated, I thought that was a real photo at first. - I did too, I was like, that's weird, the Pope is going for it. - Yeah, I was like, pretty awesome, he's got Balenciaga, go for him.

But that's today's technology. So we're about to live in a world where someone can sound like me, they can behave like me, and as we spend more and more time online, it's gonna be harder to discern what is real and what's not real. So I think in the age of artificial intelligence, the other thing people want is authenticity.

And authenticity is whatever's real, and whatever's authenticated. So I think our brand is kind of authenticity, like we're not gonna ever be the most digitally immersive company. That's gonna be social media or entertainment. Our value is really the physical world. We get you online, offline, with people different from you all over the world.

And that comes with starting with knowing who you are, authenticating your identity. Eventually, we may use biometrics, because right now we use like a government ID. But I think eventually, I want to do something with biometrics to be much more robust, so you can't really get around it. And then we have your identity, you trust us, we build this incredibly robust personal profile.

And then we can just match you and we are the then and then hopefully, we're really good interfaces. And we use the latest, greatest language models. - Yeah, it's pretty amazing how fast these are working, and what's going to be possible, because we don't know what it's going to match people with over time.

I don't know necessarily what's going to delight me, but every time I go somewhere in the world that somebody else introduces me to, like my guide on the side, a friend, if you told me, "Hey, you gotta try this place in San Francisco, cafe, Okinawa that I've been going to to get tonkatsu sandwiches." I told like three people about this, because I love these when I go to Japan, and everybody goes there and they're like, "Oh yeah, you're right, that was great." And now they spread to the next person, and that kind of word of mouth, I think like this AI is going to find little things like that, where it didn't know that this was something that you would be delighted by.

- Totally. - And it's such an opportunity. - I think it's amazing. And by the way, I think I heard another, one of your podcasts, you said something that really resonates that I think it's just worth calling out. The cost to develop software is about to go down, and maybe a good analogy, Jason, would be like the camera.

130 years ago, very few people could operate a camera. And so, therefore, you had to be a specialist to take a photo, and there weren't a lot of photos. Suddenly, computer programming is just basically telling a computer to do something in its language. AI means you can now tell a computer to do something in your language.

The moment you don't have to learn a different language, you can use your natural language to English, suddenly kind of everyone in a way can be a programmer like everyone's a photographer. You don't have to actually have a skill. Now, there will be programming skills, but suddenly anyone can do that.

Now when that's possible, there's going to be so much more software. We're going to live in an abundance of software. I think in a podcast, you referenced like a ski instructor or a ski company, like a niche business that couldn't have developed, hired great software engineers, but now they can become the best engineer you've ever had developing their app.

And so, suddenly the skills start to be different. We have to understand skiing, human psychology, taste, design, and how to operate and have a conversation with that tool, but you don't have to necessarily build the infrastructure. It's like we never built servers because we had AWS, but if we launched five years earlier, we would have had to have been really good at like kind of building out servers.

Rack and stacking servers. I mean, your first half a million would have went towards a co-location facility. And now it's like, you're just going to talk to this thing and it's going to make your software for you. So I think this is going to create, I think this is going to create millions of startups.

I think that like, entrepreneurship is going to be a boon. I think there's going to be millions more. I think anyone can essentially do the equivalent of what software engineering only allowed you to do only five years ago. It's going to be awesome for many people. It's going to be wildly disruptive for others.

Albert Einstein used to have a saying, the best way to keep your balance in a bicycle is to keep moving. And I think the best way to keep your balance in the world of AI is to keep moving forward and just adopt the tools. Don't fight it and see where it takes us.

But it's going to be pretty wild. So interesting you say that. I was just looking, the Writer's Guild was going on strike and like on the second page, the third thing from the bottom was their update on AI. And they're like, we're seeking a ban of using AI in the writer's room, using AI to ingest previous scripts, and using AI to generate future scripts and dialogue.

And it said, the most the studios will commit to is doing a yearly review with the union about technology. And it's like, don't you realize you could ingest the entirety of the Simpsons or every late night joke, and then you would start on second or third base with all these incredible ideas and brainstorms for jokes, and the jokes would get better, and the shows would be more compelling.

You're totally right. I think trying to ban AI is like trying to ban electricity. You're going to be on the wrong side of history. The genie's out of the bottle, you can't put it back in the bottle. And I think that, here's the problem, Jason. I think it's easier to imagine what jobs will be displaced than what jobs will be created.

Because we can imagine everything that now AI can do. We can't imagine everything it hasn't yet done, because that requires us to conceive of what doesn't exist. But if we remember that in all other periods in history, technology created jobs that didn't exist. This can do that too. It doesn't mean we should be blindly ignorant or not be concerned.

There's a lot of concerns I have about AI. I'm concerned about how fast it's going, and is society prepared for the speed. But I think from a creative standpoint, as a person who went to Rhode Island School of Design, I would tell the creative community, you only have to be worried if you don't want to be a part of it.

Because this is a creative tool for you. You know, computers are tools. The reason they put a handle on the back of the iMac was they used to have a saying at Apple, "Never trust a computer you can't throw out the window." Computers are tools and AI is a tool.

And I think if we think of it as a tool, then it's a tool for creativity. And you're right, you start in third base. Like, I'm already noticing at Chachibit, like, it makes my writing better. I don't use - I actually don't use most of what Chachibit gives me back, but it gives me some words.

And I'm like, "Summarize this." The cold start problem is solved, because you're like, "Hey, I want to write about, I want to make a marketing plan." And it's like, "Oh, well, here's what goes in a marketing plan." You're like, "Oh, yeah, points two and seven, let me double down on those." Or I can like, I can have a thousand word thing, say, summarizes in four sentences, and maybe I don't use the four sentences, but it gives me ideas.

By the way, before we go, I want to say, one, I keep discovering new uses for Chachibit. Here's the coolest use I've discovered. I asked Chachibit a question, "At the most fundamental level, what business are we in?" And then it spits out a not super insightful answer, like, "Airbnb is the business of travel and experiences and blah, blah, blah." And then I - the cool thing that you should do this, is ask a follow-up, and keep asking follow-ups until I can't do it anymore.

And so I ask, "What's a more fundamental business?" And it goes, "Actually, a more fundamental business that Airbnb is in is sharing." And I go, "Okay, but what's a more fundamental business?" Then it goes, "A more fundamental business is human connection." And I go, "What's a more fundamental?" And it just keeps going.

- Joy! - And you, but you start to learn, and it teaches you its first principles, right? - Yes. It reduces it down. Yeah. - And then I did the same thing with AI. I said, "How can AI transform Airbnb?" And it has these really small ideas. And then I go, "How can do it even bigger?" And you keep doing it.

And so if you keep going, go bigger, or go more fundamental. Keep going. - Yeah. Take more risk. - AI starts to teach. It helps you discover the first principles in really interesting ideas, which I think the follow-up questions with these chatbots are always more important than the first question.

- Yeah. It really gets interesting the third or fourth time. And as you said, I think one of the most profound things you've said here is, "We don't know what jobs can be created because they haven't been created yet." - Yes. - And if you look at marketplaces, whether it's eBay, whether it's Etsy, whether it's Airbnb, whether it's Uber or DoorDash, to different extents, these allowed people to create new careers for themselves.

- Yeah. - And how many people do we know now who became real estate magnates and they own 20 properties because of how well their first two properties did on Airbnb? Or they have collections on Etsy or Kickstarter. And who knows what this is gonna lead to, but it's going to...

Unless there's not enough problems and not enough human creativity and energy, then this is gonna be incredible for society, I believe. - Exactly. - I'm an optimist about it, and I'm using it every day for multiple hours a day. I'm playing with the plugins, the web tools. And I just started on Repl.it, like, putting up bounties, and I started a Python course because I'm like, "I just wanna know how to, like, stitch this stuff together," because the auto-GPTs, to me, are where this gets really wild.

- Oh, yes. - If you could start putting a couple of the ideas we talked about today on autopilot and then say, "Hey," and try to make a better result every day, it could just be trying to make a better result for how Airbnb understands my travel taste. And you say, "Hey, just keep trying to get information from Jason, ask him some interesting probing questions, or look at his social media and try to give him better ideas," and then I give the thumbs up, thumbs down, either implicitly or explicitly, and you just start understanding me.

Hey, listen, I know you gotta go. This has been amazing, dude. I'm so glad we got to finally do this. - I know. Thank you for having me. - We'll talk again soon. We gotta not wait so long. - Let's do it, yeah. Well, you know, the thing is, like, I had all these notes about, like, the blocking and tackling.

Like all great conversations, I think, and great CEOs, you've got some things on your mind about how you're architecting the company and then AI that are really profound. So, if you're an entrepreneur, you're gonna wanna listen to this with your team and probably don't put it on 2X speed because Brian and I both talk pretty quick.

But a great conversation, bookend it with the Joe interview, and we'll see you all next time on This Week in Stardust. Bye-bye. - Bye-bye. - Bye-bye. - Bye-bye. - Bye-bye. - Bye-bye. - Bye-bye. - Bye-bye. (upbeat music)