Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]

My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs. He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. We also talk about what changed for him when he stopped chasing adulation and started making things for the love of making them. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠. ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:29) Episode Intro: Brian Chesky (00:03:07) Studying Industrial Design at RISD (00:08:30) Why Founders Don't Make Good CEOs (00:09:02) Founder Mode (00:12:51) AI Founder Mode (00:14:41) The End of Pure People Managers (00:18:42) Consumer AI (00:21:45) Project Hawaii (00:25:49) Make the Problem as Small as Possible (00:29:46) Becoming a Good CEO (00:32:11) What Brian Learned From Hiroki Asai (00:36:32) The Eleven-Star Experience (00:38:48) AI and Creativity (00:41:44) Making Things for the Love of It (00:43:36) The Adulation Trap (00:46:38) The Ham Sandwich Paradox (00:52:38) Why Founder-Led Businesses Endure (00:55:14) The Person as the Atomic Unit of Airbnb (00:59:40) Disrupting Yourself With AI (01:02:11) Lessons from Bodybuilding (01:07:55) Hiring as the Most Important Job (01:09:16) Are Founders Born or Made? (01:11:04) The Motivation of an Artist (01:11:47) The Kindest Thing

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Patrick O'Shaughnessy?

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• 0:42Patrick O'Shaughnessy?

  draft SIMs, run buyer outreach, and do diligence on data rooms, all with full security and compliance handled. Every action feeds Rogo Intelligence, the firm's context layer, turning years of deal experience into a secure, governed institutional memory that makes each new transaction stronger than the last. To learn more, visit rogo.com/invest. OpenAI, Cursor, Anthy, and Vercel all have something in common. They all use WorkOS. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC, and audit logs. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS APIs to gain all of them on day zero. Visit workos.com to get started.

• 1:30Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus, along with all of our podcasts, at colossus.com.

• 1:54Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 2:22Patrick O'Shaughnessy?

  My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains what he calls AI founder mode and why it will demand even more attention to the details. He walks through his 11-star exercise, which I've used personally many times over the years, which is his way of imagining the most absurd version of a customer experience as a path to product-market fit. We talk about why founders are rarely good early CEOs and what changed him when he stopped chasing adulation and started making things for the love of making them. Please enjoy this great conversation with Brian Chesky.

• 2:59Patrick O'Shaughnessy?

  Before we hit go here, we were talking about industrial design, which you studied at RISD. And I have this weird affinity for the history of this topic just because Raymond Loewy, one of the famous industrial designers, helped me a lot in my career indirectly. I'd love to hear you just riff on the influence that guys like him had in your early studies and why you studied that in the first place. Such an interesting background.

• 3:19Speaker 02

  I was an artist growing up, and I didn't know what to do with my life. And I went to Rhode Island School of Design. And at RISD, when you're a freshman, you had to pick a major. I'm 17 years old, and I'm like, okay, in three months, I have to decide what I'm going to do the rest of my life. And I remember the department head for industrial design came. I'd never even heard of the term industrial design. I didn't know what it was. And they said, industrial design is the design of everything, from a toothbrush to a spaceship and everything in between. I immediately said, that's what I want to do with my life. Because I was thinking of maybe being an architect or something like that. So I started learning about industrial design. And I learned about Charles Reims, Raymond Loewy. Raymond Loewy, probably the most important industrial designer of the 20th century, designed so many incredible products. This first designer, Air Force One. He designed a lot of beautiful consumer products. He designed a lot of cars.

• 4:03Speaker 02

  And he had a profound impact, I think, on society. And as I was studying the history of industrial design, it was so incredible because industrial design field is a deeply technical field. The thing about it, architecture is fairly technical, but it's a more known boundary. Like, there's buildings, and there's commercial, there's residential, there's retail. There's only so much variation. It's a multi-thousand-year-old field. Industrial design, for the most part, really started with Josiah Wedgwood. It was like, it's really the master Industrial products, so industrial design is really new from the industrial revolution. And it used to be analog things. The first industrial design was chairs and tabletop dishes and bowls. But as technology grows, suddenly industrial design becomes cars and airplanes. And now you have microwaves and refrigerators.

• 4:47Speaker 02

  And you have all these things in the 20th century, radios. And then eventually it becomes like medical equipment, like ventilators. And then, you know, with computers, I mean, a lot of people, the most famous industrial design product in the world is the iPhone. And the vastness of industrial design is unbelievable. The intimate relationship you have with the product is incredible. I remember in that group in the 1980s, I loved video games. I played with a Game Boy, a Game Gear, Super Nintendo. Or remember Nike in the 80s and 90s, those sneakers, the Reebok pumps. Like, these products captured kids' imaginations and they had a very intimate relationship with you. They really had a sense of personality. And computers in particular were something I was really, really interested in.

• 5:28Speaker 02

  And then, of course, you get to the golden age of Apple, starting probably in 1998 with the iMac. And into Johnny Ive, who was my hero. So into RISD, and when I was at RISD, Apple was the golden age of industrial design. They really educated the public about design. Once they're educated, they couldn't see great products. And that captured my imagination. What I loved about industrial design was, A, it was very technical. You work with mechanical engineers, you work with electrical engineers. B, here's the thing about industrial design, it's almost different than any other design. This is also true of fashion design. A design is only successful if it sells. So if we design an office building, architects can win awards in their office building and it can never get leased.

• 6:09Speaker 02

  You can design a house, but no one looks at, well, what was the retail value of the house? So the awards are detached from the commercial success. If you design a product and no one buys it, it's considered a failure. And so because the commercial success matters, you have to think about marketing, manufacturing, distribution, solving problems. It's not just about winning awards, it's about being viable to a customer. The other thing is, it's very much a problem-solving field. It's got so many different boundaries. And it's very much about empathy, about user journeys. than I think any other design field. I think industrial design always seemed like it was the kind of field where you put yourself in the shoes of the user. You design these user journeys. And I think they really teach industrial design through user journeys. It was a very specific type of field.

• 6:54Speaker 02

  And I think that really prepared me for designing. I'll just give you one example. One of the projects I designed when I graduated was a child's ventilator. And so instead of just thinking about a child's breathing machine, instead of just thinking about the design of the ventilator, one of the projects I had to do was imagine being the child in a hospital. And so I had to imagine being a child. It's hard to do, but you're six years old. Imagine you're being six and you're scared and you're looking up at a breathing machine. And imagine the parents. The parents go in and the parents are like, is my child going to be OK? If this breathing machine seems ominous and like it's keeping you alive, the parents are going to freak out, like, what's wrong with my child? The other thing is I learned that one of the interesting things that happened was

• 7:37Speaker 02

  the nurse technicians, the really technical nurses, it's a weird thing, they had no problem that these things were complicated. But the hospital wanted a breathing machine that was so simple that everyone can learn how to use it. Except the nurse technicians had pride that only they knew how to use it. So you had to like weigh the stakeholders. How do you design something from the vantage point of a child? Consider how would it imbue to the parents? How could it be universally useful for everyone without threatening people's jobs? You see, there's so many dimensions. That just, I think, really prepared me for this field. There's no product managers in industrial design. You are the PM. There's industrial designers and there's engineers and there's program managers. So the designer is the product manager. So a designed product is one function.

• 8:21Patrick O'Shaughnessy?

  Do you think the world's going to go that way now? You're obviously famous for helping usher in this founder mode idea. That was kind of pre Opus 4.6 or whatever. There's like another layer to that now. I'm curious what we would call it. But it seems like for the first time again, someone even like you, running a very large company with lots of people, can disintermediate lots of the steps between idea and outcome. And this design stuff may be even more applicable than ever. What is the new mode like? Because everyone's trying to figure out, how do I run a company in this era? So how would you describe the new capabilities and the mode through the lens of this?

• 8:55Speaker 02

  You know, founder mode was something that Paul Graham coined, but based on an experience I had. I think people are basically born good founders. Or said differently, it's innate. You don't have to learn how to be a good founder. It's like you jump in the pool and you learn how to swim. No one is born a good CEO. And the job of CEO is completely counterintuitive. And almost all of your intuition about what to do is wrong. And so the problem is, we founders never were really prepared to be great CEOs. We founders were taught to learn by doing. And that's great for a founder. It's not good as a CEO. You do not want to learn on the job how to be CEO. In other words, trial and error is bad for CEO. You know why trial and error is really bad? Because you hire somebody, they build an empire, they leave, and now you get to unwind their empire.

• 9:39Speaker 02

  And it takes like four years. So you've wasted years. So actually, learning how to be CEO is something you should learn. And so I learned the hard way. And I basically learned that what happened was founders were overdelegating their companies to these professional managers. I'm not disparaging them, but they were detaching themselves. And they were being managed, rather than managing the company. And it was really about not apologizing about how you're running a company, being in the details. That was founder mode.

• 10:06Patrick O'Shaughnessy?

  Was there a moment that that like clicked for you? That you had to change the mode?

• 10:10Speaker 02

  Yes, the pandemic. Two things happened. Actually, speaking of Johnny Ive and Apple and another person named Hiroki here. I spent the 2010s riding a rocket ship. Airbnb, Uber, a few of us, we went on these crazy rocket ships that like Open and Anthropic are doing now. It was awesome. It was amazing. But by the end of the last decade, around 2019, I remember waking up one day and it was like completely unrecognizable, the company I was running. I had like 7,000 employees. I didn't know what anyone was doing. I felt like I was in a car without a steering wheel. And I just could not turn the company. I was like, turn left, and the company would go right. And actually, not only did I feel like I was not in control, I don't think anyone felt like they were controlled. It was just a free for all. Thousands of decisions being made for me.

• 10:52Speaker 02

  Me overly differing, not listening to my intuition. And I got to this point where I remember having this dream. And I told my co-founders, I had a dream in late 2019, where I felt like I'd left the company for 10 years. And I'd come back and I was like, somebody had been running the company for 10 years. And they like turned it into this like giant political bureaucracy. I didn't even recognize the company. And then I realized, oh, my God, it was me the whole time. And so it was my fault. Like, I had actually enabled all this to happen. And then I started talking to people and they all had the same experience. And all these founders felt like we were all made to feel crazy. Because we had this instinct. So around the same time as the pandemic, I hired a guy named Hiroki Asai. He was from Apple. And he told me about how Steve Jobs ran Apple.

• 11:34Speaker 02

  And Steve Jobs, when he came back to Apple in 1997, in July of 1997, they were nine days from bankruptcy. And he basically just like went into founder mode, what you call founder mode. He got into the details of every little detail. And I wanted to do that, but initially the company braced against it. It was almost like it repelled against it. And then the pandemic happened. And we lost 80% of our business in eight weeks. We were in total crisis mode. At that moment, I went from peacetime to wartime. And then I just totally took control of the entire company. And I just never let go. Over time, basically what I did is I reviewed every single thing for two, three years. I worked like 100 hours a week, reviewed every little detail of the company. My vision wasn't do this forever. My vision wasn't to micromanage forever.

• 12:17Speaker 02

  My vision was before I empower people, I need to know what's going on. This notion that great leadership is hiring great people and trust them to know what to do. Well, how do you know they're great if you're not auditing what they're doing? And you actually want to start hands-on, under control, and give ground grudgingly. Everyone does the opposite. They let go, they hire someone, they go in the wrong direction. And by the way, that's bad for the leader. You're not training them. So to bring it back to your question, that's founder mode. We need AI founder mode. AI founder mode is going to be even more intense than founder mode. What are the principles that you're thinking about as you go into it? I think AI founder mode, you're even in significantly more details. Because you have almost everything on demand. The mechanism of founder mode was I had a lot of meetings. Because that was the only way I gained information.

• 13:02Speaker 02

  So I probably did 35 hours of meetings, which is very similar to the way Steve ran Apple. I wouldn't do one-on-ones. I'd only do group meetings. I'd do a recurring thing where I review every single thing at the company. Either on a weekly basis, bi-monthly, or quarterly. Live in person. Live in person, group meeting, and I'd have a full chain of command. A lot of companies, you have to like get your boss to prove it and your boss's boss. Boss to prove and your boss's boss's boss to prove it. I'd have the full chain of command in the room. And anyone can give their opinion. I would make all the final decisions. I would not speak first. I'd usually speak last. And I usually agree with the team, but 10% of the time I'd disagree, but I'd ratify every decision. It was a very clear chain of command, but this is a meeting-based culture. I think in AI, I think we're going to move away from meeting-based to asynchronous.

• 13:45Speaker 02

  And we're fairly remote, and so I think that will benefit us. I think you're going to have a lot fewer layers of management. You know, I think there was an old famous saying, the Catholic Church has been going on for 2,000 years and only have four layers of management. Why do every other company have like seven, eight, nine layers of management? I know there's this like general idea, like as a thought experiment, what if I could theoretically manage all 7,000 people flat? I don't think that's a good idea. I think that's an extreme, but I do think going to a few layers of management would make a lot of sense. I'm in the middle of trying to think about how to redesign the company. I think every single person in this company's job will change. I don't know how. I've not wanted to make any rash changes. What I'm basically doing now is trying to get people to adopt AI tools. And I want to see how everyone's job changes in the world of AI tooling.

• 14:30Speaker 02

  And then I want to basically embark on like a fundamental redesign. I don't think people managers will have any value in the future. When I mean people managers, people that only manage people. I think everyone's going to have to be a hybrid people manager or manager IC. Meaning they have to have contact with reality in some sense. Yes, they have to be. A thing a customer end up seeing or touching. Yes, an engineer recall they have to be technical. In other words, every engineer needs a code. Even the managers need to code. Whatever the version of that is for your field, you need a code. So if you're a lawyer, you're just not managing people. You have to actually read the case law and you have to get involved. And that makes sense, right? You can't just be these managers where you're kind of people's therapist and you're just doing meetings, you're doing one-on-ones like. People who have lots of recurring one-on-ones are not going to survive.

• 15:12Speaker 02

  Because what they're doing is like that, oh, you come with me with whatever problem is I'm here to help you like a mentor or professor. That kind of leadership style is not going to work. You need to have context. And I think, I think a lot of people will survive this age of AI. The two types of people that will not survive the age of AI are two types of people. Pure people managers who think it's all about. Just leadership. No, it's about content and leadership. I hear about design leaders that like the heads of design, they don't actually manage the design. Johnny Ive manages design. He designs and he leads people. A design leader who only manages the people, that's crazy to me. The way Frank Lloyd managed his design team is through the work. I say you manage people through the work. You don't manage the people, you manage the work. Otherwise, what are you doing?

• 15:56Speaker 02

  I mean, yeah, like maybe a couple of times a year, you should have like a check in, have a heart to heart, ask about their family, build relationships. You should do that. You should have relationships. That's not a day to day thing. You're not their therapist. You're managing people through the work. So the two types of people will not make the shift to AI are pure people managers and people that are rigid and don't want to change and evolve. As long as you're like got a growth mindset, I think the tools are going to be very easy. There's an economic setup for the tools to be so easy, everyone can figure them out. So I don't think the AI tools are going to be complicated. Right now, there's a lot of command line. I think Claude Bot and CoWork are not the most intuitive to an average person. But I think economic incentives will be for this to become incredibly intuitive. And I think AI is really an enterprise thing right now.

• 16:41Speaker 02

  If you take out ChatGPT, then people screwing around with image generation, it's pretty much just an enterprise phenomenon. I'm on the board of Y Combinator, 175 companies last batch, 159 were enterprise. There are no consumer companies. Because there's no consumer companies, the incentive to make the interfaces really simple is not there. Because it's their job to figure out the interface. The next wave of AI is going to be consumer AI. Consumer AI is going to be the big prize. Can you think of a consumer AI company? You know, maybe OpenAI, but most of their energy is now going to Codex. Google, yeah, with Gemini, but most of it's still going to search. They don't want to cannibalize your business. So I think that's where it's all going to go. And I'm trying to start thinking about AI as a consumer play. And how do we make tools so simple that everyone here can figure out how to use them?

• 17:28Patrick O'Shaughnessy?

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• 18:13Patrick O'Shaughnessy?

  because of how far ahead RidgeLine's AI features are compared to anything else in investment management software. I've been hearing from a lot of investment managers about AI and they fall roughly into two camps with some unsure where to even start and others convinced that they can build their own order management system over a weekend. The reality is that running an investment firm will always require governance, controls and a single source of truth for your data and no amount of AI enthusiasm changes that requirement. RidgeLine is built on exactly that foundation, which is why I believe that the firms that come out ahead in the AI era will be the ones running on RidgeLine's unified platform. If you're serious about your firm's AI strategy, RidgeLine should be part of that conversation and you can request a demo at ridgeline.ai.

• 18:56Patrick O'Shaughnessy?

  It's surprising that so few have tackled consumer, so many of the biggest companies in history are consumer companies. You built one of the great consumer companies of the last generation of companies. What advice would you give to people that do want to build consumer businesses using this technology? Like if the next batch of YC startups were to invert because of your advice, what would you tell them? How would you guide them? So curious why you think there aren't more.

• 19:18Speaker 02

  Here are the three or four reasons I think it's happening. Number one, I think a lot of people when Chetan P. came out were afraid. They're afraid Chetan P. was going to kill their business. And I think a lot of investors didn't want to invest in something where they thought Chetan P. was going to kill it. Number two, the business model is tricky. There is no yet consumer business model for AI that I've seen. For example, ChatGPT, there's three ways it can monetize subscriptions. Unfortunately, they're probably going to hit a local maximum percentage of users subscribing because Claude and Gemini are giving away for free. Ads, again, they're hitting a local maximum because Claude Gemini are not going to do ads. And then e-commerce, they shut down the third-party apps. And the inference costs are expensive enough that they're burning a lot of money. And so I think the first thing is you need to have a business model around consumer

• 20:03Speaker 02

  AI. You can't just be in the business of information because people are not trained to pay for information. The second problem is distribution is mature. Now, again, top three apps in App Store are AI, so it does prove if you have something revolutionary, you'll find your way to the top. The third thing is, while I think Silicon Valley, we like to describe ourselves as rebels, I think, and maybe it's a little bit like the always-on nature of Twitter, I think it's very trend-based and vibe-based. I think there's a sense that everyone kind of does what everyone kind of does. That makes sense? I think the trend is enterprise. The other thing is why Combinator, we tell entrepreneurs, get other YC startups to be your first users. It's a really great distribution strategy, right? Like, the way we got our first users is you do things that don't scale.

• 20:47Speaker 02

  Now, what happened was that has taken the logical extension that everyone just keeps making enterprise companies. Maybe finally, the reason people aren't doing consumer companies is they're just harder. They're more hits-driven. The prize is bigger, but the risk is higher. It's more all or nothing. You can pick a narrow vertical, build a good medium-to-large-size business, it's pretty straightforward, you can get other YC companies to adopt it, and you can grow into larger and larger enterprise. It is much more history-driven business. You have to be good at a lot more things. You generally have to be better at design, marketing, culture, press. It's not purely technology and sales, which is what I'd say enterprise is. Like, you make a product, it can be a technology-based product. Oftentimes, in enterprise, the person using the product is not the person buying the product. And so, sales becomes really important, but you can start sales really small with smart and companies.

• 21:32Speaker 02

  It's really hard to figure out, how do you start small consumer? Who do you start with on the street? So I think these are the reasons why. But it might also just be that everyone's doing enterprise because everyone's doing enterprise. And it's a trend. My prediction is that we're living in the age of enterprise AI, and I think in the next 12 to 24 months, you're going to see the beginning of a consumer AI renaissance. Almost every app on my home screen has not changed fundamentally since AI, including Airbnb. I think that's going to change in two years.

• 22:00Patrick O'Shaughnessy?

  On your most recent earning call, you referenced this thing, Project Hawaii, I think it was called, which is like the on-the-ground, direct application of the soon-to-be-defined Founder AI mode or whatever. Maybe just describe what that is and how you, as an incumbent consumer company, are trying to make yourself into one of these AI companies? And sort of like, what's possible with a project like this?

• 22:20Speaker 02

  This is such a great story. So I had this conundrum. We had like 7,000 people. We were down to 5,000. I wanted to like, basically, take the magic of the founding of the company, the early stages. We were in this little apartment, working together. And I wanted to work with like this team of 10 people. And I wanted to like, have that team work on one problem. And so, we ended up focusing on one problem. We said, "Let's put a team together to focus on improving the guest experience, improving conversion rate." Conversion rate is basically, search to book. The conversion rate of people typing in a location and dates and booking. And there's a funnel. And you can basically measure the funnel, and you can do A/B test. But more than A/B testing, I wanted to do something where the North Star was, "Let's make the experience better and increase conversion.

• 23:05Speaker 02

  And we're gonna start with a better user experience." And so, we put together a team, 10 or 12 people, designers, engineers, product people, data scientists, it was mostly just a pure software team. And we treated it like a little startup. And we said, "We're gonna just focus. And we're gonna do a system of crawl, walk, run, then fly. Crawl, fix the bugs, fix the problems of conversion rate, just the easy things. And once you build a little bit more confidence, walk. Start to develop features, really start to reframe the journey, then run. Rethink the entire flow, big features. Fly, like, completely be in by yourself. And everything's gonna be measured, everything's gonna be operationalized." The team's results were phenomenal. They ended up delivering the equivalent of, I think, in year one,

• 23:50Speaker 02

  $200 million in kind of revenue for the company. The following year was like $400 million, $500 million. Now, we're at a run rate of like, over 600 basis points, 600 basis points of $13, $14 billion. You get the sense of how much of a lever that is. It was just one team. I mean, it maybe, it grew into dozens and dozens of people, maybe 50 or 60 people. But it was this really lean team. We took that team, we said, what if we apply to the next problem, pricing? Totally different team, same model, then another model, then another model. And I really tried to work with a team. And initially, I would meet with them every week, and then it became every other week, and then every month. And my general philosophy is start really hands-on and let go over time. I'm not a golfer, but like, I took a couple golf lessons. Here's an analogy for management.

• 24:33Speaker 02

  If you learn golf, you want to learn with a golf instructor before you build any habits. Because if you learn on your own, you're gonna like have a weird swing, and then when you get a golf instructor, they gotta change your muscle memory. So the golf instructor's gotta watch you swing like thousands of times. Eventually, they don't need to see you, you let go over time. What most founders do is the opposite. They bring these people in, they let them figure it out, and then they intervene later, but they already have the wrong muscle memory. So I decided, I'm gonna be totally hands-on, I'm gonna do everything with a team, teach them everything I know, and let go, then do it with the next team. And then I had teams learn from other teams. Then, when we launched services experiences, we basically found this other way of innovating. So here's a riddle, or it was a riddle to me.

• 25:18Speaker 02

  Airbnb, we had this core business that was really successful. It did nearly a hundred billion dollars a year in gross sales. For every thousand dollars spent in the world, one dollar was spent on Airbnb. Except, we had the problem of we're like a one-hit wonder. And for 18 years, I couldn't get a second hit out. And I kept wondering, like, why is this not working? And the answer is like too obvious, it was staring us in the face, but we kept having the burden of trying to scale these businesses at a global scale from the beginning. When we started Airbnb, we started in one city, New York City. We had a hundred users. I was in Y Combinator. Paul Graham goes, "Where are your users?" I'm like, "They're in New York." We have like, not many, but they're in New York. He goes, "You're in Mountain View, you're using New York, what are you doing here?" We went door-to-door, meeting users.

• 26:03Speaker 02

  The basic philosophy is make the problem as small as possible. Get to product-market fit, then scale. So we launched service experiences last year, and it didn't work right away. And I'm like, "Oh shit." And we launched service experiences in a hundred cities. And I went back, and I thought to myself, wait a second, Airbnb launched in New York, Uber launched in New York. San Francisco, DoorDash launched like Palo Alto. Let's make the problem small and just perfect a city. And so we started doing this with new businesses. We basically, any new business, we're going to do one to 10 to many. We'll pilot in one market, any idea. If we get the market to work, we'll go to 10. You get a 10 that works, we'll industrialize it. It took us 16 years to get to our second and third business. We started getting those two working. Now we have like 10 to 20 pilots.

• 26:46Speaker 02

  Eventually we'll have 50 to 70 new verticals. This is like the Hawaii system. It's basically taking this giant company, making it a really small elite team. It's like the Navy SEALs. I work with the teams really leanly. Make the problem as small as possible. I think that's a key thing. Make the problem as small as possible. Dominate a niche. Peter Thiel used to say this, he was one of our first investors. He said, "It's better to have a monopoly of a tiny market than a small share of a big market." This is counterintuitive. Every investor wants to go into big markets. I don't like big markets. Big markets have a lot of competition. Go into a small market and make it big.

• 27:21Patrick O'Shaughnessy?

  Is the reason for both of these things? The idea that it works in Toronto, but not at 100 city scale? And the reason a 10-person team can outperform a 100-person team? Is the shared reason some sort of like better contact with reality? And like somehow reality starts getting distorted as you get bigger or something?

• 27:37Speaker 02

  This comes back to the most important piece of advice I ever got. The first day Y Combinator, Paul Graham said, "It's better to have 100 people love you than a million people sort of like you." And that came from Paul Buchheit. Paul Buchheit was a partner at Y Combinator. He created Gmail. This old famous story was he created Gmail and it took him two years. And they said, "You can't ship until 100 people inside of Google love it." It actually took two years to get 100 people to actually like the product. But once 100 people like something, 100 million people like it. It's like the sample size is enough. The problem is you try to make something a million people like, you can't talk to a million people. And so you end up with this shallow swimming pool. It's like you're trying to heat up an ocean. And the ocean just, it takes too long to heat up and you can't tell. Instead of heating up an ocean, heat up a bathtub. Make the problem as small as possible. And you're close to the customer.

• 28:22Speaker 02

  In fact, if you only are focused on one city or even a subset of city, you can talk to every person. You can put all of these resources on a tiny problem. And I guarantee you, take a ton of research, you put on a tiny problem, the smaller the problem, the more you'll change the numbers, the trajectory. And that will teach you lessons. And there's you do things that don't scale, then you scale. And the scaling is industrialization. But product market fit is a distinct problem from industrialization. So you want to basically make the problem as small as possible, understand the user, put yourself in their shoes, blow their mind, do things you've never thought before, do them by hand, make them unscalable, don't worry how much it costs, just prove the model. It's like R and D, that is a lot like industrial design. This is what we call prototyping. Before you manufacture something, you prototype.

• 29:07Speaker 02

  And you make prototype after prototype after prototype. And until you make something that you love for yourself, or someone loves. So yes, the smaller the problem, the more there's fewer abstraction layers. You're actually on the ground, you're talking to people. That's how you prove it. Hawaii to these pilots, it's all the same thing. By the way, same thing with AI. You're removing abstraction layers. You're making the problem as small as possible, and you're going directly to the source. I think that's a principle that all these things have in common.

• 29:36Patrick O'Shaughnessy?

  It's like we're playing this game of telephone. If we don't do it that way, and you just lose information.

• 29:40Speaker 02

  And this is why founders don't like running large companies. They end up in a game of telephone. They say something, and then it goes down like five layers, and then it goes back up five layers. And they're in these like meetings, and the meetings become like system reviews. And literally, like, the lowest point for me when I was having meetings about meetings.

• 29:57Patrick O'Shaughnessy?

  You've gotten into this new mode, it's called founder mode, it's not called CEO mode. Do you think you're now a good CEO?

• 30:02Speaker 02

  I think I am. I think I was naturally a good founder. Although I would say I also got really lucky, because I had two great co-founders, and I damn that I lucked out on that. I think I was a very good early-stage CEO. And I think the moment I had to have like an executive team, I really struggled to make the shift from a founder to CEO. I really struggled. And I think in the 2010s, I do not think I was a great CEO. And I think we paid the price for my learning curve. And I think the pandemic was a rude awakening for me. I think I was conflict averse. By the way, somebody once said, a pitcher never takes himself off the mound. As a manager, you gotta go take them off the mound. I didn't want to hurt people's feelings. I wanted them to take them off the mound. And the longer you leave a pitcher on the mound, the more home runs they give up,

• 30:46Speaker 02

  like the more upsetting they're getting. And they're still going to be angry at you no matter when you take them off the mound. So I don't think I was naturally a good CEO. And I remember up to the pandemic, at one point, I wonder, I wonder if I'm just not meant to be a CEO. Maybe I'm not meant to do it. And then the pandemic happened. We had a near death experience. And I said, well, screw all the rumination. Like, it's do or die. And I feel like I learned how to do the job. There's really a few phases of CEO. Have an idea, get to product market fit. Product market fit to hypergrowth. Hypergrowth scale to become a real company. Real company as in profitable public. And I did all that. We have like 40% free cash flow margin. We're very profitable. We do $100 billion in sales. The last phase of a CEO is reinvent the company. Product extension.

• 31:29Speaker 02

  And the reason our stock has been flat is because we only do one thing. And we've started to saturate a little bit of the core idea. So we've had to reinvent ourselves. We had to do product extension. So I still got to prove myself. And then there's another proof point. Can I navigate this transformation of AI? I think founder mode is going to be the only way to operate in the age of AI. If you're a giant professional CEO, I think you can operate in a founder mode. But if you're like risk averse, you want to be incremental, those types of people are not going to survive the age of AI. So I think there was an old Albert Einstein quote. He said, the best way to keep your balance on a bicycle is to keep moving. You're going to have to keep moving. Founders are going to be really well primed or set up for this age of AI because we kind of have to redesign our whole company from scratch again.

• 32:14Patrick O'Shaughnessy?

  Was there anything else that Hiroki taught you? Because Steve was perhaps the literal ultimate example of everything you just said. Focused on the details, in the weeds forever, reinvention of the company.

• 32:25Speaker 02

  And before I say, just to say who Hiroki is, everyone knows Johnny Ive. Hiroki is a bit of an unsung hero. I always heard about him. He was like this legendary mythical figure that like was elusive. There's like almost no photos of him online. There's like no videos of him. He was never out in front, but he was Steve Jobs' creative director. It was a function under marketing. He did the ads, he did the graphic design. He was really responsible for, you know, when he was like that black type with the gray font and like the product in front of white. That was really his aesthetic. He taught me two principles of Apple that I brought. One was simplicity. I think startups are like, when you start a company, because you have no money and you're so constrained, you're naturally simple. Lack of abundance creates natural constraints.

• 33:09Speaker 02

  And so simplicity is thrust upon you, and that is good for you. And then, once you raise a bunch of money and hire a bunch of people, you go in a lot of directions, then you lose your sense of focus. How many startups can we think of today who have struggled from lack of focus? Probably name a few. So you start to lose your muscle for simplicity. Hiroki taught me simplicity. And he taught me simplicity is not removing things. Simplicity is distilling something so fundamentally that you understand its essence. I know Steve used to say, "Design is the fundamental soul of the man-made creation that reveals itself through subsequent layers." In other words, great design is about distilling something to its essence. It's kind of what Elon does with SpaceX, where he talks about first principles.

• 33:51Speaker 02

  And first principles is kind of like a physics term, but it's also a design term. It's about understanding, if I'm going to reinvent this product, I have to understand the properties of glass. I have to understand like everything about it to distill it to its essence. So I got obsessed with simplicity. Simplicity of our products, simplicity of our organization, simplicity of everything. The other one was a sense of craft and details. How you do anything is how you do everything. And I said, "Everything must be perfect." It comes from, there is a book that a lot of people in Silicon Valley recommend, The Score Takes Care of Itself. Bill Walsh, the coach of the San Francisco 49ers. John Wooden, winning as coach in college basketball history, UCLA. Same principle. First day at UCLA, so John Wooden, won 10 NCAA championships over 12 years.

• 34:35Speaker 02

  First day, first hour in his team, he spends an hour teaching you how to put your socks on. One hour, and he said, "Put your socks on this way."

• 34:42Patrick O'Shaughnessy?

  Mr. Miyagi.

• 34:43Speaker 02

  Yeah, one hour teaching you how to put your socks on. It's a metaphor. Everything was that rigorous. Bill Wall said, "The way you tuck your jersey into your pants was one of 10,000 details that depend on whether you won or not." Basically, don't focus on winning. Focus on getting all the inputs perfect. And you get everything perfect, then you will win. And you don't focus on the scorecard. We do focus on growth, but we kind of stopped focusing on growth. We started focusing on making everything perfect. And if everything is perfect and you don't grow, then you focus on the wrong input. But if you have the right inputs and you make them perfect, then you'll grow really fast. And so that's really what I learned from him. He really taught me, I think, Founder Mode. Because I'd never met Steve, so I only knew through Hiroki. And I said, "Well, I love this.

• 35:27Speaker 02

  I'm an artist, I'm a designer, I could have more control of the product. I get to make everything perfect." The initial attempt at Founder Mode created giant revolts. Everyone hated it. Because everyone thought I was micromanaging. And I learned something fundamental. Initially, everyone hated it, and by the end, everyone loved it. The people hated it left, so maybe there's like selection bias. The people liked it, stayed. But even the people that thought they wanted autonomy and independence and empowerment, what they didn't realize was control and power is not zero sum. It's not like if I have all the power, you don't. There's a scenario where we're all powerless. And there's also a scenario where if I have power, I can therefore give you power. It's not zero sum. This is the problem people don't understand. If I have more power and control, I can give you more power and control, and I can hand it off to you.

• 36:12Speaker 02

  It's about the idea that the car has a steering wheel. You turn it left and it actually goes left. I do think it's all about the company rowing in one direction. That's it.

• 36:21Patrick O'Shaughnessy?

  The thing that you've said historically that had the largest impact on me was this notion of the 11-star experience, the exercise of going from not a five-star, but a six-star, and actually forcing yourself to write it. And I have this idea in mind because of this idea of simplicity and distillation. And it's a beautiful thing, right? It's ultimately empathetic with the customer. But why is that idea in practice so powerful? Like, what happens as you go up the star count to 11 stars?

• 36:47Speaker 02

  So let me do like a one minute on what it is. Basically, when you book an Airbnb, most people leave a five star. And if you leave a four star, it's a bad experience. Five star, everything went as planned. So it's called review compression, similar to Uber. You always leave a five star. And if you leave anything other than a five star, something really went wrong. But what if the driver was really amazing? You can only leave a five star. So I started imagining, what if we could give a six star? And I did this exercise from six to like 10 or 11 stars. So a five star, let's say, take one moment checking into Airbnb. Five star check-in is you get there and the host greets you, or there's a door code and it works. In other words, nothing went wrong and you give a five star. Anything went wrong, you give a four star or less. That's review compression. Like, what if you went above and beyond? So what would a six star look like? A six star would look like you basically get to the Airbnb

• 37:32Speaker 02

  and there's your favorite wine on the table, and there's like fruit, and there's snacks there, and there's a handwritten card. Okay, that's better than just letting me in the house. So what's a seven star experience? Seven star experience, there's like a limousine or something waiting for me at the airport. They know I like surfing. There's a surfboard waiting for me, and they're like showing me around the city and all this stuff. So what's an eight star experience? An eight star experience, I get to the airport, there's an elephant. I go on the elephant, I go on a parade in my honor. I'm like, wow, I feel really special. What's a nine star experience? I call it the Beatles check-in. I get off the plane in like 1964 Beatles. There's 5,000 teenage girls screaming my name with cards, making me feel like I'm a pop star. I get to the front lawn of the Airbnb, and there's a press conference with my name. So what's a 10 star experience?

• 38:16Speaker 02

  10 star experience, Elon Musk greets me and takes me to space. It's an exercise. It's an exercise in the absurd. You keep pushing to go so absurd to 10 stars that suddenly six or seven stars doesn't seem crazy at all. And the way to get to product market fit is to just create a six or seven star experience. But you can't create a six or seven star experience without going beyond. In other words, go beyond the edge of reality and work backwards. And so it's kind of a fun exercise. What would the craziest possible way to blow someone's mind? One person's mind, one customer? And maybe try that. And maybe you can't scale that because that's like an eight star experience. But you can probably scale a six star. And that difference between the five and six star is probably difference between you and a competitor.

• 38:58Speaker 02

  And if you can find a way to industrialize it and scale it, you might have product market fit and something special.

• 39:03Patrick O'Shaughnessy?

  One of the things that I think about when you give the absurd examples at the high end of the range is this feeling that I've experienced with AI that my imagination had almost atrophied. That by using these tools, I realized how hard it was like, oh, I can make anything. And I sit down like, I have no fucking idea what to make.

• 39:18Speaker 02

  Yes.

• 39:18Patrick O'Shaughnessy?

  And that as I started making little things, like all of a sudden my imagination got rebooted. And it feels like this exercise is like an imagination exercise.

• 39:26Speaker 02

  It is like, one of the sayings is great writing is great thinking. But I find that, I don't know about you, some people have ideas and they think of the ideas and they write them down. Sometimes I figure out the ideas through the act of writing. The act of writing is the act of coming up with ideas. The act of designing is the act of coming up with ideas. It's really hard to just sit in a room and abstractly think of ideas. You need to like do something. And so I think what was happening was we didn't have enough tools to express ourselves. I think a lot of the tools were very passive tools. I think increasingly we were spending more and more time on a sit back experience like social media. What I like about AI is I think AI shifts our attention from consumption to creation.

• 40:11Speaker 02

  Social media, a lot of us spend our time on, and the only type of creation is giving your opinion. But you're mostly consuming. What I love about AI is it's not about opinions. It's about testing the hypothesis for making. I love what's happening right now. Suddenly all of us have a paintbrush and a canvas to make stuff. I think that AI is going to lead to a renaissance in creativity. And I was an artist growing up. I was a pretty good artist, so I had the ability to express ideas. Here's an analogy. You ever meet a person, like you probably think of musicians like Prince, you name a musician that probably in words couldn't express themselves like, you know, but then through music, there's like this dimension you never knew. An artist, they seem really reserved, but their art is like really emotional.

• 40:55Speaker 02

  So many of us have this creativity inside of us. But we don't have the craftsmanship or tools to express it. And suddenly what AI is going to do is going to give us the ability to express it. We're going to realize there are a lot more creative people than we thought. Because we typically think of creative people as people that know how to express their creativity. It turns out, what if everyone can express it? Pablo Picasso once said, "All children are born artists, so problems remain artists as one grows up." Every child's creative. If every child's creative, that means every adult could be creative. I think that every human on this planet is creative. You ask the average person, "Are you creative?" About 1 in 2 says they're not. That's my experience. That's not true. It's just that they haven't exercised the muscle. And I think that the magic of AI is what's in our head can manifest.

• 41:39Speaker 02

  But also, as you said, we can develop new ideas in our head because it's a relationship. We maybe have a small idea, we try something, gives another idea, and you go on this journey. A lot of people call founders visionaries. We're more expeditionaries. We're on these expeditions. We only call it visions later. We're really just one foot in front of the other.

• 41:59Patrick O'Shaughnessy?

  Can you talk about the difference between the act of creation in pursuit of, you said people pleasing earlier, achievement notches on the belt, versus just for the raw, pure joy of it, which seems to be more the way, the mode you're in now?

• 42:13Speaker 02

  I think when I started Airbnb, I don't think we were totally trying to be successful. And I like to joke that if I was trying to make money, I would have come up with a better idea than airbed and breakfast. I truly did it for the love and the fun. And somewhere along the way, I got really successful, and that almost became a curse. Because success became a scorecard, and then I wanted to get even more successful. It stopped being intrinsic, and it started being a version of status and people pleasing. It took me a little while to realize what I was doing. What I really wanted was love. I think that I learned, growing up as a child, the way to get love is to be special. And the way to be special is to do special things. And if I do special things, I get praised and I feel love. I think that translated into, if I'm really successful, I will get adulation.

• 42:58Speaker 02

  And if I get adulation, I'll feel that feeling that I'm always seeking. And I didn't do this consciously. I'm not like saying this. It took me many years to realize this is what I was doing. By the way, adulation is kind of like seeking status. So many people seek status. Anyone's on social media and posting all the time is probably somewhat seeking status. There's nothing wrong with it, but the problem is that's not where great products and great companies come from. See, adulation is like a cup with a hole at the bottom, and you keep filling it in. Thinking it's love, except it just keeps coming out the bottom. And at some point, you have to confront, who am I doing this for? Am I doing it for other people? For them to briefly love me and commend me to then move on? And either way, that's a drug. And it's a drug that's like real drugs.

• 43:42Speaker 02

  You need a greater hit to get the high and eventually it stops working. And eventually you reach a peak and it gets really meaningless and empty. And that happened to me. And at some point around the pandemic, we go public. We have a hundred billion dollar valuation. It's like one of the best days of my life. And the next day I wake up, I like put on sweatpants to go on a Zoom meeting. It was like it never happened and it became like the saddest day of my life. Cause I realized, okay, what now? I got this adulation and I don't feel any different. And that made me like reevaluate like what I'm doing this for. I had to like just come to terms with, I wanna do things for pure intrinsic reasons. And so I had to basically detach myself from people's approval, from status, from worrying about like how hot Airbnb is or how successful I am,

• 44:27Speaker 02

  which I never gave a shit about when we started. You know, you start getting accolades and you want more of them. And you gotta like let go of that because this is a losing game. And I just really started focusing on being heads down. Do the work like you used to do, like when you were a kid. There was light, just make stuff, make it for yourself. That great book, Rick Rubin, he says, an artist is an artist when they make it for themselves. And they don't try to make something successful. And I stopped trying to be successful and I just went back to the basics. And I realized like, a person doesn't know you will never love you. That's okay. The people will love you and the people that know you. And the most important person that to love you is yourself. And we should love as the thing you're doing. So this became like a whole thing. It became about doing it because you love it, putting your heart and soul in it. It's like the score takes care of itself.

• 45:12Speaker 02

  It goes back to that. Don't try to be successful. Try to do something wonderful that you love for yourself. Maybe you'll be successful, maybe you don't. But don't focus on who you wanna be. Focus on what you wanna do. That was the Vice President Obama once told me. He said, if I focus on who I wanted to be, I focus on being President of the United States, and I wasn't, my life would have been a failure. But if I focus on what I wanted to do, I wanna help people, I wanna be a community organizer, then I don't need to be president. And so I think so many entrepreneurs focus on what they wanna be. I wanna be a giant tech founder. I wanna run a billion dollar company. I wanna do this, I wanna do that. Instead of focusing, what do I wanna make? And then suddenly there's no way to fail if you're making what you love.

• 45:48Patrick O'Shaughnessy?

  Some incredible set of ideas. I'm curious what most fell away in your life in this recent period as a result of this shift in mindset? Like, what do you do less of that you used to do a lot of when you stopped chasing adulation?

• 45:59Speaker 02

  Mostly ruminating.

• 46:01Patrick O'Shaughnessy?

  You ruminate less?

• 46:02Speaker 02

  Yeah, just like worrying about people's opinions of me. By the way, somebody kept saying like, "There's something mildly narcissistic about worrying about everyone's opinions, as if they're all thinking about you." The reality is, even people watching this, like, "I'm gonna be self-conscious, except for a moment they're gonna think about me, but then they're gonna be mostly thinking about themselves, and that's okay." And all of us are thinking, everyone's thinking about us, and they're thinking about themselves. Or the people in their life. They're not thinking about some guy on a podcast, except for like, maybe an hour. And then it's over. Letting go of what people think about you. Because that's a prison. Suddenly, you're making things for approval. And then you lose your courage. That's the main thing. It's just like the mental energy. But I really try to do things that are meaningful.

• 46:47Speaker 02

  Meaningful things are really two buckets. It's making and spending time with people I care about. Those are two things.

• 46:53Patrick O'Shaughnessy?

  There are two very different ideas I'm curious for you to react to. The first was, made famous by Warren Buffett, who said, "You want to buy, as an investor, businesses that a ham sandwich could run, because eventually one will." Not to pick on anyone, but think about like, the card payment processors, like Visa or MasterCard, like just extremely elegant business models. Actually, a network effect businesses like Airbnb tend to be in this category. And then you've got this opposite end of the spectrum, which is, one of my favorite investors, early-stage investors, said, "He tells every founder that they should think about the company as a platform or a vehicle for their own personal growth. And that their ability to grow will set the ceiling for the company." This is sort of like opposite ideas. And we've been talking a lot more about leadership in this second bucket. I'm curious how you think about whether or not you care

• 47:37Patrick O'Shaughnessy?

  if eventually a ham sandwich ran Airbnb, like, the business model would be so perfected that it wouldn't matter, in the Warren Buffett sense? And just like in general, how you think about if that's true, that your ceiling is the company's ceiling, as it's leader?

• 47:50Speaker 02

  I think they're both true. Let me try to square those with one example. I agree with both sentiments. Okay, here's an example. Walt Disney. People watching, I want them to try to name a Paramount Pictures film. I want you to name a Warner Brothers film. Maybe you'll think of like Batman. I want you to name a Universal Pictures film. I want you to name something from the MGM library. Pretty hard, right? But you can name a lot of Disney films. And probably Pixar during their golden age. There's a big difference to us, too. One is that Disney was very founder-led. And that Disney was all about a personal expression of one man. The irony is, the longer a company is run by founders in the founder mode, the more I think it can let go and anyone can run it.

• 48:34Speaker 02

  I think Disney, not to take away from the CEO of Disney, the new guy Josh is really great. I've met him, he's great. And I think they've had a lot of good CEOs. But I generally think the CEO of Disney has the bases loaded. You've got this incredible theme park that like people are gonna visit no matter how well it's run. Like it's like a city that, as many people visit Disneyland every year as like San Francisco. It's crazy. They've got this incredible IP. It's not that it's the easy job, but like Walt left so much. I remember I was speaking to the former CFO of Disney once. This was like 10 years ago. And he said, "Disney hasn't really done anything new since Walt died. Walt died in 1966. Since 1966, we still make feature-length films, TV, and Magic Kingdoms." And of course, yeah, they do new things, but fundamentally, that's the same playbook.

• 49:17Speaker 02

  So I do think that that's an example where the founder reinventing the company and their expression created such a reservoir of IP, of momentum. He died 50 years ago. 50 years later, Walt Disney's spirit seems very omnipresent. Whereas Louis B. Meyer, I don't know if most people can tell you which studio he was. See what I'm saying? There's a huge difference. So I generally think this is a paradox. The ham sandwich, you have a business so good and you can run it because sooner or later they will. The best businesses are ones that founders run and they reinvent and they create so much equity in such a great moat that then when they hand it off, they wonder and grow after them. I think Apple is very similar.

• 50:00Speaker 02

  They've not had to invent new products, for the most part. They're still running the iPhone. What a gift Steve left them. They were a few hundred billion dollar company when he died. They're like a multi trillion dollar company now. I think the one caveat is I think tech companies are different. Warren Buffett generally didn't invest in tech companies with the exception of Apple. Coca-Cola was a big investment of his or like Sees Candy. These are things that don't get disrupted. I think technology is a synonym for change. If we're in the change industry, you kind of need to be more in founder mode more time. But I think that's how I square it. The company is the upper bound of the founder's potential. The longer you're in founder mode, the more it will endure. I remember one founder told me, I want this company to last 100 years. So therefore I can't be in all the details.

• 50:45Speaker 02

  And so therefore I need to empower people. And I remember saying, if you want somebody to be around for 100 years, you want to control it as long as possible and keep it in founder mode as long as possible. Like Disney. I think that's counterintuitive. And I think people say, oh, but like the company is going to get very dependent on you. Well, yeah, but the alternative is you're going to have so institutionalized, this magic that it can't endure after you.

• 51:09Patrick O'Shaughnessy?

  Edwin Land, the founder of Polaroid, was very famous for using Ansel Adams as his ultimate tester of his equipment. And so he cared about the most important, maybe best photographer of all time, what he thought of his device. Comes to mind when you talk about Disney because I have this visual of Walt just like continuing to drill down to some sort of bedrock or something. And that like, that's the mission that you're on as a founder is like bedrock. What is that for you from this point forward? Like as you keep drilling, what do you think you're still after? Where is there still room for your ceiling to raise so that the businesses can?

• 51:43Speaker 02

  A few things come to mind. When people think of Airbnb, if you close your eyes and say, I want you to think of a picture of Airbnb, you probably think of a house. We're a noun and a verb like Kleenex, which is amazing and not amazing. It's amazing in that like we're kind of the category leader. It's also tough because when you're Kleenex, you want to sell shampoo. They're like, wait a second, I'm not putting Kleenex on my head. It's a double edged sword, our brand. The bedrock for me is how do I change the atomic unit of Airbnb from a home to a person? I do not want Airbnb to be about homes. I want it to be about people and I want the People to be atomic unit and the Airbnb you get a home, you can experience, you can get a service, eventually a flight. I want, imagine like a person in the center with a ring with like 50 things around. These are the things you can get.

• 52:28Speaker 02

  That is the thing. The bedrock of Airbnb is going to be identity, profile, the person's preferences. I want to develop the most authenticated identity on the internet. Proof of personhood is going to be really, really important in the age of AI, artificial. I want to develop the most robust profile on the internet. I mean, there used to be Facebook. They've kind of abandoned that strategy. I want to build one of the richest preference libraries of you as a person because that would be useful to have. I want to build a social graph, but in the real world. And I want to eventually have a membership program where you get all these different benefits. So the bedrock is the person. I want to basically figure out how we can launch like Amazon, Amazon from books to like 100 things. I don't want us to just have homes. I want us to have 100 things.

• 53:13Speaker 02

  So we need to develop this industrialized machine of understanding what are the like atomic units or the primitives that are consistent across all these different businesses? And then the last one is AI. We have a bit of the innovator's dilemma. Plus or minus 100 billion dollars goes through our app. I have all these visions that'll totally change it. But you're a public company, you know, and you're like giving guidance and the difference between missing and hitting earnings is not just being public company, people's livelihood depends on Airbnb. If we mess with something, somebody could go from like making a living, not making a living. So you got to be very careful. That is not an environment for mass innovation when you're being really careful.

• 53:53Speaker 02

  So I'm also exploring little sandboxes, like almost like a separate app, like what is a radically, radically different Airbnbs? What's after Airbnb? Airbnb C. What's that? What's the next? Think about, so those are the three things I'm thinking about. Number one, how do we take the atomic unit from a home to a person? Number two, how do we basically industrialize what Airbnb offers to do like 50 things, not three things? And then how do we disrupt ourselves before someone else does with AI without screwing over our investment? Masters and our hosts do depend on us. And so those are the kind of things I'm doing. Maybe the last thing I'm thinking, just as a CEO, is I think I've reached a certain level of mastery.

• 54:36Speaker 02

  I've reached the mastery of like product market fit, hypergrowth, profitability. I'm beginning level four. Level four is reinventing yourself, product extension. I think there's something potentially even beyond that in the age of AI, which is like, one of my strengths is all my experience and that's also my weakness now. Like I'm 44, I'm not old, but I'm not young. I'm not AI native in the same way a 22-year-old is. But here's a bad example. When I started me, I was 25, 26, and we were competing against Expedia. They were on like Outlook and we used Google Docs and we were like iPhone. It all seems anachronistic now, but back then, that was innovative. And we were on the coolest new tools and we just moved faster. And so also just staying young.

• 55:18Speaker 02

  Pablo Picasso, another quote, he said, "The older you get, the stronger the wind gets and it's always in your face. You've got to stay light on your feet, you've got to stay young. You've got to keep reinventing yourself, you've got to have curiosity." And so I don't want to become like this old school person in the groove. I got to reinvent myself.

• 55:34Patrick O'Shaughnessy?

  One of the things that as I've been building stuff myself, really for the first time, like I'm not an engineer. I used to build stuff, but I'd tell people and it would come, the feedback loop was like painfully slow and lossy. Now it's like five to 15 minutes and pretty high fidelity. And soon it'll be five seconds and perfect fidelity. I always loved Brett Victor's idea of wanting the input and the output being as linked as possible. And we're getting to that stage. The anxiety I have having this experience is that it feels like just nothing will last. Historically, there's been these ways to have enduring moats, people would always call them. You have 200 million people that you know a lot about already. You've got hundreds of millions of reviews, that lots of information on places. Like you have these embedded things that I can't just get that from you.

• 56:17Patrick O'Shaughnessy?

  But it just seems as I build this stuff like, oh, it's going to be really hard to have something enduring and lasting. Do you share that anxiety? How does that make you feel that as the frictions fall, it also feels like the pot of gold at the end of the rainbow is like disappearing into the distance or something?

• 56:33Speaker 02

  Here's an analogy. Take a fashion brand. Like Hermes, I think the most valuable single fashion brand in the world. The Birkin bag and the Kelly bag, it's like they have a new product every like decade or something. Like these are like multi-decade old things and they appreciate and they resell. And then you've got like Zara, fast fashion. And I feel like we all want to make these things that endure, but we're living in like hyper-fast fashion of software. If you look at software from 10 years ago, no matter how great it was at the time, it looks really old and dated. You look at hardware from 10 years ago, it looks pretty decent. You look at interior design, it looks pretty good.

• 57:09Patrick O'Shaughnessy?

  Or better.

• 57:10Speaker 02

  Or better. You look at buildings, after a certain period of time, they've got this patina and they're wonderful. You go to Paris and old endures. Environments and physical worlds have got huge endurance. Hardware and physical things have medium endurance. Software is extremely ephemeral. Opinions are like that, but some ideas permeate. This is something I'm wrestling with myself because I want to make things that endure. I don't know how I've reconciled it, except to say this. I obsess over our app, Airbnb's app, its design, its interface. And yet, no matter how great it is 10 years from now, I'm going to look at it and think it looks like crap. Because I look at the interface from 10 years ago and think it looks like crap, no matter how good it was. Gated software never looks good, even if it was good back then.

• 57:54Speaker 02

  So then you gotta ask, what endures? I do think there are things that endure. Airbnb, the community endures. I started realizing the software won't endure. And the network effect will decently endure, but the ideas of Airbnb, its principles, its mission, the organization, the company, the brand, the identity, the logo, the voice, the community, what it stands for, those things will endure. Most importantly, the community. I realized at some point, I told the company, we're not building an app, we're not building a service, we're building a community. Because that's the only thing that will last. I don't think there will be apps in the future. I think there'll be agents. So like if we're attached to apps, I don't think there will be apps. So we better like let go of that.

• 58:33Patrick O'Shaughnessy?

  So many of the themes that we've talked about is this steady progress and learning through time, applied in service of others. What did bodybuilding, when you were a young teacher, about steady progress over time?

• 58:45Speaker 02

  Weirdly, bodybuilding taught me so much that I can apply to Silicon Valley. It taught me two important principles. My dad was really into ice hockey, wanted me to be an ice hockey player. Unfortunately, I was very skinny. I hit puberty really late. And I went to a sports academy for hockey. When I was thirteen, I thought I could be a really good hockey player. But by the time I was fourteen, I didn ' t hit puberty until I was like fifteen or sixteen. And that ' s a death sentence in hockey because suddenly, I went from like first or second line to third or fourth line. And I went from thinking I ' d be a division one athlete to division three athlete. I ' m like, it ' s not really gonna work out for me. And so I started weightlifting. I was one hundred thirty five pounds. And I told my friends I ' m gonna be like, won the top five of both the country by the time I was nineteen. And they thought I was like out of my mind. I ended up by nineteen competing at the national level.

• 59:30Speaker 02

  I competed at teenage nationals. The first lesson I learned from bodybuilding was if you can change your body, you can change your life. It was actually the most fundamental thing to change. Like, everyone wants to change things around them, but what if you changed you first physically? And I even think like, if you could start somewhere, a lot of people say like change your thoughts. I would change your body first. Change your physical biology. You can change your body, you can change your life. It was the ultimate expression of empowerment. Okay, now I changed my body. What else can I change? It ' s a metaphor for eventually you can design the world around you. I can change your body. I can change my environment. Eventually I can change the world. It ' s like you just go inside out. But the other thing it taught me, which might be even more helpful, is that you can ' t get in shape in one day. And if you go to the gym and work out for like twenty hours, you ' re not gonna get in better shape.

• 1:00:17Speaker 02

  In fact, you ' re gonna overtrain. And the way you get stronger is an adaptation from progressive overload that you basically, you stress the body. The body doesn ' t get stronger during exercise. It actually breaks the muscles down and it ' s adaptive response. Like an immune system, it gets stronger. You just keep doing it. The basic idea is that you can ' t get in the shape in one day and it ' s about one percent better every single day. And if you compound one percent a day, you can actually have massive gains. And so it ' s really about discipline. And it ' s also very analytical. Bodybuilding is this wonderful thing where it ' s judged. It ' s a subjective sport that you judge visually, but you measure it scientifically. You weigh your food, you have to put yourself in the right caloric deficit, you have to write down your training, you have to write down your weights. It's like extremely analytical. They're taught me to be very analytical, metrics-driven,

• 1:01:02Speaker 02

  and that it's really about discipline and consistency. And I think that's important because I think a lot of founders just give up too early. It's about discipline. And it's about if you train for a month, you take a month off, you're starting over. And that's the key. You never quit, you just keep going.

• 1:01:16Patrick O'Shaughnessy?

  One of the nice things about it is the visual feedback. Like you judge visually. You can literally see it. You can look in the mirror, other people can look at you and say you've been working out. Probably some of the skills that you would want to apply the same progressive overload thing to as a leader are very invisible. How do you figure out the objective function? Like, how do you apply that same thing to something else that other people can't see?

• 1:01:36Speaker 02

  I start trying to focus on like how good of a company Airbnb is. I take it to like projects. So I'll give you one example of a project I focus on. One is I want to build the best team possible. So twice a year, we do this like giant thing we call roadmap review. And there's the top 100 people in the room. And I see the quality of people in the room. And we did one the last two days. And then one of my most important jobs, the most important job I do at Airbnb is hiring. That's a whole separate topic. And the visual feedback is every twice a year, I get the top 100 people in the room and I can see the quality of the people in the conversation. So in other words, there's many metrics that you use and I obsess over. Maybe it's the app and I just look at the design of the app. Maybe it's like how well the company operates and I look at decision making. So I try to break the problem down to something that's observable, that I can observe, either measure with data

• 1:02:20Speaker 02

  or even subjectively look at and observe. So it's always about breaking the problem down to something that's observable and measurable. By the way, just on this, because this is a really important point. Basically, as a leader, you can choose if you want to spend time hiring or managing, one or the other. The better the people, the less time you need to be managed. The more time you spend on recruiting, the less time you have to spend on management. It's one-to-one. I remember when I was starting Airbnb, Sam Altman, who obviously everyone knows now as OpenAI, I was like one of the first Sequoia-funded companies before me, where two people that had ever been funded by Sequoia from Y Combinator, Drew Houston from Dropbox. But the first one, Sam Altman, is a company called Loop. It was like a way to see your friends on a phone before the iPhone.

• 1:03:02Speaker 02

  I remember him telling me, I was like 27 or 28, Sequoia just funded us $600,000, a $3 million post-money valuation, highest valuation Y Combinator. Now the average valuation is 30 million. And he said, "You're gonna spend 50% of your time on hiring." I never did, by the way. It was my death blow, not spending more time on hiring. The less time I spent on hiring, the more time I spent managing. And I started learning, my number one job was hiring. Every day I wake up, the first person I call is my recruiter. I think people should think about their first employee being a recruiter, not an engineer. They are the most important person because they are the ones that like get you every other person. I mean, a company is as good as its people. And the difference between like the good companies, the great companies, or the people, I think AI kind of makes that clear now that like what's all about the people.

• 1:03:46Speaker 02

  But I obsess. I obsess over recruiting. I spend hours a day. And I don't recruit executives. I recruit two, three layers deep. Here's how you hire good people. Do not do searches. Generally, what you want to do is build pipelines. So here's the mistake people make when they hire. They do, "I need to hire a blank." So they do a search, they hire a search firm. And the search firm scans, they give you like 50 profiles. You like call it down to 10 people. You contact 10, and you pick the best one you hire. And a year later, you realize like they're good or bad. And if they're bad, uh-oh, they've already hired their own team. That is the wrong way to do it. So the best way to do it is pipeline recruiting. You're constantly recruiting, you're constantly meeting people. So this is what you do. Try to map out all the best people in the valley.

• 1:04:31Speaker 02

  So let's say I need to hire really good engineers. I don't do searches. I just informationally meet the best engineers in the world. Every meeting, the job is to get the next meeting. Meet someone else. So if I were to meet you and I say, "Hey, who's the best people you know? Can you introduce me to two or three people?" So what you're doing is you're constantly meeting people in advance of searches. And you're just building your pipeline. You just need to know lots of talent. And all of it's referral-based. The two ways to find out if people are good, I mean, one way is you're just good at assessing talent. But the two best ways is start with the results, work backwards to the people. So a lot of people say like, "I want like a really good marketer. I'm gonna go to Nike, they do really good marketing." No, no, no, you do that. Find an ad you like. And then figure out who made that ad. Start with the results, work backwards to the people. Don't start with the resume.

• 1:05:15Speaker 02

  The other thing to do is keep asking people to build your Rolodex. And so I'm constantly building a Rolodex. And the moment I find somebody that's really good, I ask them who all the best people they know are. And I basically build these little mafias. Every company's got like a little mafia of talent. So like Uber's got like an ops mafia. Apple's got like a design mafia. And then like build these little ecosystems and they tell you who the other good people are. And you're classifying more people, more people. And what I do is I am the co-hiring manager for the top 200 people in the company. This is very radical. A lot of CEOs think it's their job to hire their executive and their executive team hires their team. I think that is fatal. I mean theoretically, yes. Theoretically, you should live in a world, we have such good people, they can all hire their own people.

• 1:06:00Speaker 02

  Most entrepreneurs, if they have 10 executives, they'd be lucky if two or three are able to do that without any support or help. In other words, you always want to be like marrying up, hiring people to feature. I sometimes used to say like, my executives should hire people so good, they would never work for them without my help. In other words, it should be like we're reaching. If you can hire them on my help, we're not reaching far enough. You want to like hire the very best person you can. So I'm constantly meeting people, constantly interviewing. The first and last call I make every day is the recruiting team. Still, I probably spend two, three hours a day on it. Every day, every year I spend more time on recruiting, the less. By the way, in the 2000s, I didn't. I thought it was all about like having a good idea, having a recruiting machine, managing people.

• 1:06:46Speaker 02

  The great thing is I don't manage as much anymore. The more time you spend recruiting, the less time you spend on management because the really good people are self-managing. This is amazing. And if you have to manage people, then maybe you should think about like upgrading the talent.

• 1:07:00Patrick O'Shaughnessy?

  You said before that founders are born, you think, and CEOs can be more shaped?

• 1:07:04Speaker 02

  For the most part. And maybe the caveat to that is just like, maybe founders aren't born, but we spent our whole life tinkering and building. But you can't simulate being a CEO.

• 1:07:12Patrick O'Shaughnessy?

  I was gonna ask whether or not you think they're activated in some way, like maybe there's the raw material, but then some event happens. Sean from Talenture would call this the Bruce Banner, you know, gamma rays thing or something. What have you learned about activating talent?

• 1:07:25Speaker 02

  I think the activation is giving someone a challenge. Our founding stories, we couldn't afford to pay rent. But of course, I have 50 stories before that of challenges I had. It's just Airbnb, that story activated something on a scale I'd never done before. But it wasn't the first thing I made. I was making things my whole life. I think the way to activate somebody is to give them a problem or opportunity and see if they can do it. I think the people that have a high level of agency are going to do it. I don't know how to teach motivation. I don't know if it can be taught, by the way. I don't know if you can teach them. I think you can motivate people. I don't think you can make a person who's not motivated, motivated. But I think all entrepreneurs have the trait of their self motivated. And so it's really about giving them a challenge.

• 1:08:10Speaker 02

  And then it's up to them to step in and activate.

• 1:08:13Patrick O'Shaughnessy?

  Having plugged the leaky bucket of motivation of adulation, what's your motivation now as you attack this next chapter?

• 1:08:20Speaker 02

  Most of my heroes are artists. I'll pick four people. Two I've mentioned repeatedly. Leonardo da Vinci, Vincent van Gogh, Walt Disney, Steve Jobs. There's many things they had in common, but what is something that I had in common? The last day of their life or the last week of their life, they were working. Leonardo da Vinci carried the Mona Lisa with him until he died. And he definitely didn't paint the Mona Lisa for adulation because he never showed it to anyone. Vincent van Gogh sold one painting his life. He died an obscure artist in the cornfield, maybe shot, maybe not, unclear what happened. But did it because he loved it. Walt Disney, last day of his life, he was laying in a hospital bed. His brother Roy was like rubbing his cold feet, dying of lung cancer.

• 1:09:04Speaker 02

  Looking at the ceiling tiles, which were a grid, imagining Disney World. Steve Jobs, Haruki said the last couple of weeks of his life, he like showed him like marketing, like he was still looking at products. Now, some people can look at that and interpretation is, oh, that's sad. Like they weren't spending time with family. By the way, I'm sure those that had families, Vincent van Gogh and Leonardo da Vinci didn't have families. My understanding is Steve and Walt spent time with their family at the end of their life. But I don't see that as a sad story they're working in the end. Because I think they did what they loved. You know, the great artists in history did what they love. My motivation is the motivation of an artist. My motivation is to create something great. That is my motivation. I would like to be successful. I want our shareholders to get a return.

• 1:09:49Speaker 02

  I would like employees to feel that they're at a great company. I would love to make a huge impact in the world. But mostly, I just want to make something. I feel like I'm a designer more than I am a CEO. And I might be afforded one of the great, biggest canvases of any designer in human history. Because usually designers are just not given this many resources. It's almost like a glitch in a system. It was almost like accidental. Some air beds allowed me to crack this glitch and get all these resources I wasn't supposed to get. But I'm not letting go. And so, my motivation is that of an artist. I just want to make incredible things.

• 1:10:19Patrick O'Shaughnessy?

  It's a beautiful, almost closing thought, given the tools now at our disposal, that everyone can do that if they want. And we should encourage them to do so.

• 1:10:27Speaker 02

  All children are born artists. The problem remains one as you grow up. AI is the opportunity for all of us to become artists and scientists and creators. We don't have to be consumers anymore. We can be creators. True creators. And we hear the word creator, you think social media performer. That's one way to create. You can perform. The problem is, I think creator has meant performance. Now creator can be create, make. Everyone can make now. It's amazing.

• 1:10:52Patrick O'Shaughnessy?

  The last question I ask, everyone's the same. What is the kindest thing that anyone's ever done for you?

• 1:10:57Speaker 02

  The biggest gift anyone's given me is believe in me. And I think the biggest gift you can give somebody, or one of the biggest gifts is believe in you. A couple of examples. When I was 16 years old, I transferred to a public high school. I was really into art. I was a pretty good artist. I didn't know how good I was. And I had a teacher named Miss Williams. She believed in me. I remember her telling my parents, "He's going to be a famous artist." I never became a famous artist. But it gave me confidence that I was actually good at something. Because I wasn't that good at hockey. I wish I was, and I wish I could make my dad proud of ice hockey. I just didn't get very far. And suddenly, that belief set me on a path. That moment, I said, "I'm going to go to art school." And that moment, I realized, "I can decide to be happy the rest of my life." I came to Silicon Valley.

• 1:11:40Speaker 02

  I met Michael Seibel and the guys at Justin Day TV, and they believed in me. They were early YC people. Paul Graham made an exception to let me in early at Y Combinator. He believed in me. I was an engineer, and he almost never funded non-engineers. He thought the idea was not a good idea, actually. He said, "People are actually doing this?" I go, "Yes." He goes, "What's wrong with them?" But he believed in me. My investors, I can go down the list of investors, they believed in me. Joe and Nate, I had no business being a CEO. Joe somehow believed in me. I wouldn't be here if it wasn't for the generosity of people believing in me, in helping me. And I think the greatest gift I can give back in believing in others and help them, and not pull the ladder up behind me, but to like really show them.

• 1:12:22Speaker 02

  Yeah, I had the great privilege to eventually join the Giving Pledge, and you have to write a letter. I remember my letter was, "If you could ask my high school teachers who would join the Giving Pledge, they wouldn't have guessed me." The basic idea in my life philosophy is we all have unknown potential. I think we have these stories in our own head about what we're capable of. To go back to John Wooden, somebody once asked him, I think, like, "What's the secret to success?" And he said, "I only ask my players to do their very best." Person goes, "Oh, wow, that seems weird. That sounds like what a parent says to the kid who like loses all the time." Goes, "Here's a catch. I saw potential in people they didn't see in themselves." And that's my management philosophy. When I tell somebody it's not good enough, I'm not saying you're not good enough. I'm saying I see potential and you don't see in yourself.

• 1:13:07Speaker 02

  That is the most motivating thing you can do, to say, "I believe in you, and I believe you can do even more." And people will climb a mountain for that type of thing. And maybe the way to end this whole conversation is the most important person ever that you can believe in is yourself. And I think a lot of us that are entrepreneurs, we're driven by insecurity. We're driven by some hole. Not all of us, but a lot of us. Something in our childhood, something, a lot of us were not the coolest kids or whatever, and there's something in us you wanted to prove. And then you get really successful, and you still have imposter syndrome. And a lot of like the path to happiness and salvation is just the path of learning to believe in yourself. For me, I only believed myself long after other people believed in me. Now my gift is to try to give it to others. Beautiful place to close.

• 1:13:52Speaker 02

  Thanks, man. Thank you very much.

• 1:13:55Patrick O'Shaughnessy?

  If you enjoyed this episode, visit colossus.com. You'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus, our quarterly print, digital and private audio publication, featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at colossus.com/subscribe.

• 1:14:35Patrick O'Shaughnessy?

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