Brian Chesky on Founder Mode, the CEO Job, and Redesigning Airbnb for AI

Brian Chesky

I was an artist growing up, but I didn't know what to do with my life. I went to the Rhode Island School of Design, and at RISD, when you're a freshman, you have to pick a major. I'm 17 years old, thinking, okay, in three months I have to decide what I'm going to do the rest of my life. There were 18 majors. The department head for industrial design came in — I'd never even heard the term. He 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.

I learned about Charles and Ray Eames, and about Raymond Loewy — probably the most important industrial designer of the 20th century. He designed his first Air Force One and a lot of beautiful consumer products. He had a profound impact on society. As I studied the history of the field, it was incredible, because industrial design is a deeply technical field. Architecture is fairly technical, but it's a more known boundary — buildings, commercial, residential, retail, only so much variation. Industrial design really started with Josiah Wedgwood; it came out of the industrial revolution. The first industrial design was chairs and tabletop dishes and bowls. But as technology grows, it becomes cars and airplanes, then microwaves and refrigerators, then medical equipment, and now the most famous industrial design in the world is probably the iPhone.

I grew up in the 1980s and I loved video games — a Game Boy, a Game Gear, Super Nintendo. Or the Reebok Pumps. These products captured kids' imaginations; you had a very intimate relationship with them. They had a sense of personality. And then you get to the golden age of Apple, starting around 1998 with the iMac and Jony Ive, who was my hero. Apple educated the public about design, and once people were educated, they couldn't unsee great products.

What I loved about industrial design is that it's very technical — you work with mechanical engineers and electrical engineers. But here's the thing: a design is only successful if it sells. Architects can win awards for an office building that never gets leased; the awards are detached from commercial success. If you design a product and no one buys it, it's a failure. Because commercial success matters, you have to think about marketing, manufacturing, distribution — being viable to a customer, not just winning awards.

It's also very much a problem-solving field, and it's about empathy — user journeys. More than any other design field, industrial design is about putting yourself in the shoes of the user. One of the projects I designed when I graduated was a child's ventilator. Instead of just designing a breathing machine, I had to imagine being a six-year-old in a hospital, scared, looking up at this machine. Then imagine the parents: if the machine seems ominous, they freak out — what's wrong with my child? And the nurse technicians had pride that only they knew how to use it, but the hospital wanted something so simple everyone could learn it. So you had to weigh all the stakeholders. There are so many dimensions, and that really prepared me. There's a reason I became a CEO: in industrial design there are no product managers — the industrial designer is the PM.

Brian Chesky

Founder mode was something Paul Graham coined, based on experience I'd had. People are basically born good founders — it's innate, you don't have to learn how to be a good founder. But no one is born a good CEO, and the job of CEO is completely counterintuitive; almost all your intuition about what to do is wrong. Someone tells you something and you want to agree with them, but you have to be careful about agreeing without getting the other side. The problem is we founders were never prepared to be great CEOs. We were taught to learn by doing, which is great for a founder but bad for a CEO. You do not want to learn on the job how to be a CEO — trial and error is terrible, because someone builds an empire, then leaves, and now you spend four years unwinding it.

So I learned the hard way. What had happened was that founders were over-delegating their companies to professional managers. I'm not disparaging them, but founders were detaching, being managed rather than managing. Founder mode was about not apologising for how you want to run your company, and being in the details.

Brian Chesky

Yes — the pandemic. I spent the 2010s riding a rocket ship, like Airbnb, Uber, a few of us — the way OpenAI and Anthropic are doing now. It was amazing. But by the end of the decade, around 2019, I woke up one day and the company was completely unrecognisable. I had 7,000 employees and I didn't know what anyone was doing. I felt like I was in a car without a steering wheel. I'd say turn left and the company would go right. And it wasn't just me — no one felt in control. It was a free-for-all, thousands of decisions being made for me, me overly deferring, not listening to my intuition.

I had a dream in late 2019 where I felt I'd left the company for ten years and come back, and someone had turned it into a giant political bureaucracy, and I didn't recognise it — and then I realised it had been me the whole time. It was my fault; I'd enabled all of it. I started talking to other founders and they'd all had the same experience; we'd all been made to feel crazy for having this instinct.

Around the same time I hired a guy named Hiroki Asai from Apple, and he told me how Steve Jobs ran the company. When Jobs came back in July 1997, Apple was nine days from bankruptcy, and he went into founder mode — into the details of everything. I wanted to do that, but initially the company repelled it. Then the pandemic hit and we lost 80% of our business in eight weeks. We went from peacetime to wartime, and I took total control of the entire company and never let go. I reviewed every single thing for two or three years, working 100 hours a week.

My vision wasn't to micromanage forever. It was: before I empower people, I need to know what's going on. The idea that great leadership is hiring great people and trusting them — well, how do you know they're great if you're not auditing what they're doing? You want to start hands-on and in control, and give ground grudgingly. Everyone does the opposite: they let go, hire someone, that person goes the wrong direction, and by the way that's bad for the leader too, because you're not training them. That's founder mode. And now we need AI founder mode.

Brian Chesky

AI founder mode is going to be even more intense — you're in significantly more detail, because you have almost everything on demand. The mechanism of founder mode was meetings; that was the only way I got information. I did about 35 hours of meetings a week, very similar to how Steve ran Apple. I wouldn't do one-on-ones, only group meetings — a recurring review of every part of the company, weekly, monthly or quarterly, with the full chain of command in the room. Anyone could give an opinion, I'd usually speak last, I'd agree with the team 90% of the time and disagree 10%, but I'd ratify every decision.

In AI, I think we'll move away from meeting-based to asynchronous — we're fairly remote, so that will benefit us. You're going to have far fewer layers of management. There's an old saying that the Catholic Church has run for 2,000 years with only four layers, so why does every other company have seven, eight, nine? I don't think managing 7,000 people flat is a good idea — that's an extreme — but going to a few layers makes a lot of sense. I'm in the middle of trying to redesign the company. I think every single person's job will change. Right now I'm getting people to adopt AI tools so I can see how each job changes, and then I want to embark on a fundamental redesign.

I don't think people managers — people who only manage people — will have any value in the future. Everyone's going to have to be a hybrid: a manager who's also an individual contributor. Even the managers need to code, and whatever the version of that is for your field, you need to do it. If you're a lawyer, you can't just manage people; you have to read the case law and get involved. The leadership style where you're basically people's therapist, doing endless one-on-ones like a mentor or professor — that's not going to work. You need context.

The two types of people who won't survive the age of AI are pure people managers who think it's all about leadership, and people who are rigid and don't want to change. I hear about heads of design who don't actually design. Jony Ive manages design by designing and leading people. The way Frank Lloyd Wright managed his team was through the work. You manage people through the work — you don't manage the people, you manage the work. Maybe a couple of times a year you have a check-in, go to dinner, ask about their family, build the relationship — you should do that. But it's not a day-to-day thing. You're not their therapist.

As long as you have a growth mindset, the tools will be easy. There's an economic incentive for them to become so easy everyone can figure them out. Right now there's a lot of command line — Claude Code and Cowork aren't the most intuitive to the average person — but the incentives will make this incredibly intuitive.

Brian Chesky

One last thought: AI is really an enterprise thing right now. If you take out ChatGPT and people messing around with image generation, it's pretty much an enterprise phenomenon. I'm on the board of Y Combinator — 175 companies in the last batch, 159 were enterprise. There are basically no consumer companies. Because there are no new consumer companies, the incentive to make interfaces really simple isn't there. The next wave of AI is going to be consumer AI, and that's the big prize. Can you name a consumer AI company? Maybe OpenAI, but most of their energy is going to Codex now. Google, with Gemini, but most of it's still going to search — they don't want to cannibalise their business.

Brian Chesky

Here are the three or four reasons I think it's happening. Number one, when ChatGPT came out a lot of people were afraid it was going to kill their business, and a lot of investors didn't want to fund something ChatGPT might kill. Number two, the business model is tricky — there's no proven consumer AI business model yet. ChatGPT has three ways to monetise: subscriptions, but they'll hit a local maximum because Claude and Gemini are free; ads, another local maximum because Claude and Gemini won't do ads; and e-commerce, but they shut down third-party apps. And inference costs are high enough that they're burning a lot of money. You can't just be in the business of information, because people aren't trained to pay for information.

The third thing is distribution is mature — though the top three apps in the App Store are AI, which proves that if you have something revolutionary you'll find your way to the top. The fourth thing is that Silicon Valley likes to describe itself as rebellious, but it's actually very trend-based and vibe-based; everyone kind of does what everyone else does, and the trend is enterprise. At Y Combinator we tell entrepreneurs to get other YC startups as their first users — a great distribution strategy — but taken to its logical extension, everyone just keeps making enterprise companies.

And maybe the final reason is that consumer companies are 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, vertically integrate with AI, get other YC companies to adopt it, and build a solid enterprise business. Consumer is much more hits-driven. You have to be good at more things — design, marketing, culture, press — not just technology and sales. In enterprise, the person using the product often isn't the person buying it, so sales matters, but you can start sales small with smart companies. In consumer it's hard to figure out who you even start with. My prediction is that we're living in the age of enterprise AI, and in the next 12 to 24 months you're going to see the beginning of a consumer AI renaissance.

Brian Chesky

I think that's going to change in two years.

Brian Chesky

I had this conundrum. We had 7,000 people — we'd come down to 5,000 — and I wanted to recapture the magic of the founding, when we were ten people in a little apartment working on one problem. So we put a team together to focus on improving the guest experience and conversion rate — search to book. There's a funnel you can measure and A/B test, but more than testing, I wanted the north star to be: make the experience better and increase conversion. We put together maybe 10 or 12 people — designers, engineers, a couple of product people, data scientists — treated it like a little startup, and used a system of crawl, walk, run, then fly. Crawl: fix the bugs. Walk: develop features, reframe the journey. Run: rethink the entire flow. Fly: completely reinvent. Everything measured.

The results were phenomenal. In year one the team delivered the equivalent of about $200 million in internal revenue; the next year $400 or $500 million. Now we're at a run rate of over 600 basis points — 600 basis points of $134 billion in gross sales. That gives you a sense of the lever, and it was just one lean team. Then we said, what if we apply the same model to the next problem — pricing? Same model, different team. Then another, and another.

My general philosophy is start hands-on and let go over time. I'm not a golfer, but I took a couple of golf lessons, and here's the analogy for management: you want to learn with an instructor before you build any habits, because if you learn on your own you develop a weird swing, and then the instructor has to change your muscle memory. So the instructor watches you swing thousands of times, and eventually they don't need to. You let go over time. What most founders do is the opposite — they bring people in, let them figure it out, and intervene later, once the wrong muscle memory is set. So I decided to be totally hands-on, teach the team everything I know, and then let go, then do it with the next team, and have teams learn from other teams.

Here's a riddle that puzzled me. Airbnb's core business was hugely successful — nearly $100 billion a year in gross sales; for every $1,000 spent in the world, $1 was spent on Airbnb. But we were a one-hit wonder. For 18 years I couldn't get a second hit out, and the answer was staring us in the face: we kept trying to scale new businesses at a global scale from the very beginning. When we started Airbnb, we started in one city, New York, with 100 users. Paul Graham said, you're in Mountain View, your users are in New York — what are you doing here? So we went door to door meeting them. Make the problem as small as possible, get to product-market fit, then scale. But when we launched services and experiences, we launched in 100 cities at once and it didn't work right away.

So I thought: Airbnb launched in New York, Uber in San Francisco, DoorDash in Palo Alto. Let's make the problem small and perfect one city. Now, with any new business, we go one to ten to many. Pilot in one market; if it works, go to ten; if that works, industrialise. It took us 16 years to get our second and third business; now we have 10 to 20 pilots and eventually we'll have 50 to 70 new verticals. That's the Hawaii system — take a giant company and make it a small, elite team, like the Navy SEALs. Make the problem as small as possible. Peter Thiel, one of our first investors, used to say it's better to have a monopoly of a tiny market than a small share of a big market. Every investor wants big markets, but big markets have a lot of competition. Go into a small market and make it big.

Brian Chesky

This comes back to the most important advice I ever got. On the first day of Y Combinator, Paul Graham said it's better to have 100 people love you than a million people sort of like you. That came from Paul Buchheit, who created Gmail. The story is he wouldn't ship until 100 people inside Google loved it — it took two years. But once 100 people love something, 100 million will; the sample size is enough. The problem with trying to make something a million people like is that you can't talk to a million people, so you end up with a shallow swimming pool — you're trying to heat up an ocean, and it takes too long and you can't tell. Instead of heating up an ocean, heat up a bathtub. If you focus on one city, or even a subset of a city, you can talk to every person and put all your resources on a tiny problem. The smaller the problem, the more you'll move the numbers.

You do things that don't scale, then you scale — and the scaling is industrialisation. Product-market fit is a distinct problem from industrialisation. Make the promise as small as possible. Understand the user, put yourself in their shoes, blow their mind. Do things by hand, make them unscalable, don't worry what it costs — just prove the model. It's like R&D, and it's a lot like industrial design, where before you manufacture you prototype after prototype after prototype until you make something you love. The smaller the problem, the fewer the abstraction layers. Same thing with AI — you're removing abstraction layers, going directly to the source.

Brian Chesky

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

Brian Chesky

I think I was a naturally good founder, though I also got really lucky, because I had two great co-founders. I was a very good early-stage CEO, but the moment I had to have an executive team I really struggled to make the shift from founder to CEO. In the 2010s I do not think I was a great CEO, and we paid the price for my learning curve. I was conflict-averse. Somebody once said a pitcher never takes himself off the mound — as the manager, you have to take him off. I didn't want to hurt people's feelings, but the longer you leave a pitcher on the mound, the more home runs they give up, and they'll be angry no matter when you pull them.

At one point before the pandemic I wondered whether I was even meant to be a CEO. Then we had a near-death experience and I thought, screw the rumination — it's do or die. And I feel like I learned how to do the job. There are a few phases: have an idea and get to product-market fit; product-market fit to hypergrowth; hypergrowth to becoming a real, profitable, public company. We did all that — we have about 40% free cash flow margin, we're very profitable, we do $100 billion in customer sales. The last phase is to reinvent the company through product extension. The reason our stock has been flat is that we only really do one thing, and we've started to saturate the core idea, so we've had to reinvent ourselves. I still have to prove myself, and then there's another proof point: can I navigate this transformation to AI?

I think founder mode is going to be the only way to operate in the age of AI. Even a giant professional CEO can operate in founder mode, but if you're risk-averse and incremental, you're not going to survive. Einstein said the best way to keep your balance on a bicycle is to keep moving. Founders are well set up for this age, because we kind of have to redesign our whole company from scratch again.

Brian Chesky

Hiroki is a bit of an unsung hero — a legendary, elusive figure with almost no photos or videos online. He was never out front, but he was Steve Jobs's creative director, a function under marketing. That black type with the grey font, the product in front of white — that was his aesthetic. He taught me two principles of Apple. One was simplicity. When you start a company you have no money, so you're naturally simple — lack of abundance creates constraints, and simplicity is thrust upon you. Then you raise money, hire people, go in many directions, and lose your focus. Hiroki taught me that simplicity isn't removing things; it's distilling something so fundamentally that you understand its essence. Steve used to say design is the fundamental soul of a man-made creation that reveals itself through subsequent layers. It's like what Elon does with first principles at SpaceX — a physics term that's also a design term.

The other principle was craft and details. How you do anything is how you do everything; everything must be perfect. There's a book a lot of people in Silicon Valley recommend — The Score Takes Care of Itself, by Bill Walsh, the 49ers coach. John Wooden won ten NCAA championships in twelve years, and on the first day, in the first hour, he'd spend an hour teaching players how to put their socks on. It's a metaphor — everything was that rigorous. Bill Walsh said the way you tuck your jersey into your pants was one of 10,000 details that determined whether you won. Don't focus on winning; get all the inputs perfect. We stopped focusing on growth and started focusing on making everything perfect — because if you have the right inputs and make them perfect, you'll grow fast.

The initial attempt at founder mode created giant revolts. Everyone thought I was micromanaging. But I learned something fundamental: by the end, everyone loved it — though the people who hated it left, so maybe there's selection bias. Even people who thought they wanted autonomy didn't realise that control and power aren't zero-sum. There's a scenario where we're all powerless. If I have more power and control, I can give you more power and control and hand it off to you. It's about the car having a steering wheel — you turn it left and it goes left. It's all about the company rowing in one direction.

Brian Chesky

Let me do a minute on what it is. When you book an Airbnb, most people leave five stars; four stars means a bad experience. It's called review compression — five stars means nothing went wrong. But what if the host was amazing? You can still only leave five. So I started imagining a six-star experience, and I did the exercise up to 10 or 11 stars. Take checking in. A five-star check-in: you get there, the host greets you or the door code works — nothing went wrong. A six-star: you arrive and there's your favourite wine on the table, fruit, snacks, a handwritten card. A seven-star: there's a limousine waiting at the airport, they know you like surfing so there's a surfboard, they show you around the city. An eight-star: you get to the airport and there's an elephant, and a parade in your honour. A nine-star is the Beatles check-in — you get off the plane and it's 1964, 5,000 teenagers screaming your name. A ten-star: Elon Musk greets you and takes you to space.

It's an exercise in the absurd. You keep pushing so far that six or seven stars suddenly doesn't seem crazy at all. The way to product-market fit is to create a six- or seven-star experience, but you can't get there without going beyond the edge of reality and working backwards. You can't scale an eight-star, but you can probably scale a six-star, and that difference between five and six stars is probably the difference between you and a competitor.

Brian Chesky

It is. One of the sayings is that great writing is great thinking. Some people have ideas, then write them down. But sometimes I figure out the ideas through the act of writing — the act of writing is the act of coming up with ideas, and the act of designing is the act of coming up with ideas. It's hard to sit in a room and think of ideas in the abstract; you need to do something. I think what was happening is we didn't have enough tools to express ourselves. The tools were passive; we spent more and more time on sit-back experiences like social media. AI shifts our attention from consumption to creation. On social media, the only creation is giving your opinion or posting — you're mostly consuming. What I love about AI is that suddenly all of us have a paintbrush and a canvas. I think AI is going to lead to a renaissance in creativity.

I was a decent artist growing up, so I had the ability to express ideas. But you meet people — think of a musician like Prince — who couldn't express themselves in words, but through music there's a whole dimension you never knew. So many of us have creativity inside us but don't have the craftsmanship or tools to express it, and AI is going to give us that ability. We'll realise there are far more creative people than we thought. Picasso said all children are born artists; the problem is to remain an artist as you grow up. If every child is creative, every adult could be. Ask the average person if they're creative and about one in two says no — but that's not true; they just haven't exercised the muscle.

A lot of people call founders visionaries. We're more expeditionaries — we're on these expeditions, one foot in front of the other, and we only call them visions later.

Brian Chesky

When I started Airbnb, I don't think we were trying to be successful. I inflated three air mattresses — Airbnb stands for Air Bed and Breakfast. If I'd been trying to make money, I would have come up with a better idea than air bed and breakfast. I truly did it for the love and the fun. Somewhere along the way I got really successful, and that almost became a curse, because success became a scorecard. It stopped being intrinsic and became a version of status and people-pleasing.

What I really wanted was love. I learned as a child that the way to get love is to be special, and the way to be special is to do special things — then you get praised and feel loved. That translated into: if I'm really successful, I'll get adulation, and adulation will give me that feeling I'm always seeking. I didn't do this consciously; it took me years to realise it. But adulation is like seeking status, and that's not where great products and companies come from. Adulation is a cup with a hole in the bottom — you keep filling it, thinking it's love, but it keeps draining out. It's a drug; you need a greater hit to get the high, and eventually it stops working and feels meaningless and empty.

That happened to me. We went public, a $100 billion valuation — one of the best days of my life. The next day, because of the pandemic, I woke up, put on sweatpants, and got on a Zoom meeting. It was as if it never happened, and it became one of the saddest days of my life, because I realised: okay, what now? I got all this adulation and I don't feel any different. That made me re-evaluate what I was doing it for. I had to detach from people's approval, from status, from worrying about how hot Airbnb is — which I never cared about when we started. It's a losing game.

There's a great book by Rick Rubin where he says an artist is an artist when they make it for themselves, not when they try to make something successful. I stopped trying to be successful and went back to basics — make stuff, make it for yourself, like when you were a kid. A person who doesn't know you will never really love you, and that's okay; the most important person to love you is yourself, and the thing to love is what you're doing. Don't focus on who you want to be; focus on what you want to do. Vice President Obama once told me: if I'd focused on who I wanted to be — president of the United States — and I hadn't become it, my life would have been a failure. But I focused on what I wanted to do: help people, be a community organiser. Then you don't need to be president. So many entrepreneurs focus on what they want to be — a giant tech founder, running a billion-dollar company — instead of what they want to make. There's no way to fail if you're making what you love.

Brian Chesky

Mostly ruminating — worrying about people's opinions of me. There's something mildly narcissistic about worrying about everyone's opinions, as if they're all thinking about you. No one is. Even people watching this will think about me for a moment, then mostly think about themselves, and that's okay. Letting go of what people think is the main thing, because otherwise you make things for approval and lose your courage. Now I try to do things that are meaningful, and meaningful things fall into two buckets: making, and spending time with people I care about. Anything else is an obligation I'll do once in a while.

Brian Chesky

I think they're both true. Take Walt Disney. Try to name a Paramount film, a Warner Brothers film — maybe Batman — a Universal film, something from the MGM library. Pretty hard. But you can name a lot of Disney films, and probably Pixar during their golden age. Disney was very founder-led, all about the personal expression of one man. And the irony is that the longer a company is run by founders in founder mode, the more it can later let go and anyone can run it. Not to take away from Disney's CEOs — they've had good ones — but they have the bases loaded: incredible theme parks people will visit no matter how well they're run, incredible IP. A former Disney CFO told me ten years ago that Disney hadn't really done anything new since Walt died in 1966 — still feature animation, TV, and Magic Kingdoms. Walt died 50 years ago, and his spirit is still omnipresent. Whereas Louis B. Mayer — most people can't even tell you which studio he ran.

The ham sandwich point holds: the best businesses are the ones founders run and reinvent, creating such a moat that when they hand it off, it endures and grows after them. Apple's similar — they haven't had to invent new products for the most part; they're still running the iPhone. What a gift Steve left them: a few-hundred-billion-dollar company when he died, a multi-trillion-dollar company now. The one caveat is that tech is different. Warren Buffett generally didn't invest in tech, except Apple — Coca-Cola and See's Candy don't get disrupted. Technology is the cinema for change, so you need to be in founder mode more of the time. The company is the upper bound of the founder's potential, and the longer you're in founder mode, the more it will endure.

One founder told me he wanted his company to last 100 years, so he needed to empower people and step out of the details. I said the opposite: if you want something to last 100 years, control it as long as possible and keep it in founder mode as long as possible, like Disney. People say the company gets dependent on you — but the alternative is that you institutionalise the magic so it endures after you.

Brian Chesky

A few things. When people think of Airbnb, they picture a house. We're a noun and a verb, like Kleenex — amazing because we're the category leader, but tough, because when you're Kleenex and you want to sell shampoo, people say, wait, I'm not putting Kleenex on my head. So the bedrock for me is changing the atomic unit of Airbnb from a home to a person. I don't want Airbnb to be about homes; I want it to be about people. Picture a person in the centre with a ring of 50 things around them — a home, an experience, a service, eventually a flight. The bedrock becomes identity, profile, preferences. I want to develop the most authenticated identity on the internet — proof of personhood is going to be really important in an age of AI — the richest preference library of you as a person, a social graph in the real world, and eventually a membership programme.

Then I want to industrialise, like Amazon going from books to 100 things — understand the primitives that are consistent across all these businesses. And the last one is AI. We have a bit of the innovator's dilemma: plus or minus $100 billion goes through our app, so I have visions to totally change it, but we're a public company giving guidance, and people's livelihoods depend on Airbnb — if we mess with something, a host could go from making a living to not. That's not an environment for mass innovation, so I'm also exploring little sandboxes — almost a separate app — asking, what's after Airbnb? How do we disrupt ourselves before someone else does, without screwing over our investors and hosts?

Maybe the last thing, as a CEO: I've reached a certain mastery — product-market fit, hypergrowth, profitability. I'm beginning level four: reinvent yourself, product extension. But there may be something even beyond that in the age of AI. One of my strengths is all my experience, and that's also my weakness now. I'm 44 — not old, not young — but I'm not AI-native the way a 22-year-old is. When I started, we were competing against Expedia; they were on Outlook and we used Google Docs and had an iPhone. It seems anachronistic now, but back then we were on the coolest new tools and moved faster. Picasso said the older you get, the stronger the wind gets, always in your face. You have to stay light on your feet, keep reinventing, keep your curiosity.

Brian Chesky

Take a fashion brand like Hermès — the Birkin bag, the Kelly bag. They have a new product every decade; these are multi-decade things that appreciate and resell. And then you've got Zara, fast fashion. We all want to make things that endure, but we're living in the hyper fast fashion of software. Software from ten years ago looks really old and dated, no matter how great it was. Hardware from ten years ago looks pretty decent. Interior design, buildings — after a while they get a patina and become wonderful. You go to Paris and the old endures. Physical environments have huge endurance, hardware medium endurance, software is extremely ephemeral.

This is something I'm wrestling with, because I want to make things that endure. I obsess over Airbnb's app — its design, its interface — and yet, no matter how great it is, in ten years I'll look at it and think it looks like crap, because I look at the interface from ten years ago and think that. So what endures? The community endures. The network effect will decently endure. But the ideas of Airbnb, its principles, its mission, the organisation, the brand, the identity, the logo, the voice, the community, what it stands for — those endure. Most importantly the community. At some point I told the company: we're not building an app or 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 if we're attached to apps, we'd better let go of that.

Brian Chesky

Weirdly, bodybuilding taught me so much I could apply to Silicon Valley. My dad was into ice hockey and wanted me to be a hockey player, but I was very skinny and hit puberty late. I went to a sports academy for hockey, and when I was 13 I thought I could be really good, but I didn't hit puberty until 15 or 16 — a death sentence in hockey. I went from first line to third or fourth line, from thinking I'd be a Division I athlete to a Division III one. So I started weightlifting. I was 135 pounds and I told my friends I'd be one of the top bodybuilders in the country by the time I was 19. They thought I was out of my mind, but by 19 I was competing at the national level.

The first lesson was: if you can change your body, you can change your life. Everyone wants to change the things around them, but what if you change yourself first, physically? A lot of people say change your thoughts; I'd change your body first. Get healthy before you go to therapy — start with your physical biology; that fixes a lot, and then you can do other things. It's the ultimate expression of empowerment: I changed my body, so what else can I change? I can change my environment, and eventually I can change the world. You go inside out.

The other lesson, maybe even more useful: you can't get in shape in one day, and if you work out for 20 hours you'll overtrain, not get stronger. You get stronger through progressive overload — you stress the body, it breaks down, and it adapts, like an immune system. It's about 1% better every single day, and if you compound 1% a day you get massive gains. So it's about discipline and consistency. Bodybuilding is subjective — judged visually — but measured scientifically: you weigh your food, put yourself in the right caloric deficit, write down your training and your weights. It taught me to be analytical and metrics-driven. A lot of founders give up too early. If you train for a month, then take a month off, you're starting over. You never quit; you just keep going.

Brian Chesky

I take it to the project level. One project I focus on is building the best team possible. Twice a year we do a giant roadmap review with the top 100 people in the room, and I can see the quality of the people and the conversation. That's my visual feedback. It's always about breaking the problem down to something observable and measurable — the design of the app, the quality of decision-making, the quality of the people.

And this is a really important point: as a leader, you can choose to spend your time hiring or managing. The better the people, the less they need to be managed. The more time you spend recruiting, the less time you spend managing — it's one to one. When I was starting Airbnb, Sam Altman — a bit of a wunderkind then, running a company called Loopt — told me I'd spend 50% of my time on hiring. I never did, and that was my death blow. The less time I spent hiring, the more time I spent managing. My number one job is hiring. Every day, the first person I call is my recruiter. People should think about their first employee being a recruiter, not an engineer, because the recruiter is the one who gets you every other person. A company is only as good as its people.

I obsess over recruiting — I spend hours a day, and I don't just recruit executives; I recruit two or three layers deep. Here's how you hire good people: do not do searches. Build pipelines. The mistake people make is: I need to hire a blank, so I hire a search firm, they give me 50 profiles, I narrow to ten, interview a few, do references — which are of course positive — and hire, and a year later realise the person is good or bad, and if they're bad, they've already hired their own team. That's the wrong way.

The right way is pipeline recruiting: you're constantly meeting people, constantly. Say I need great engineers — I informationally meet the best engineers in the world. Every meeting's job is to get the next meeting: who are the best people you know, can you introduce me to two or three? You build your pipeline in advance of any search, all referral-based. There are two ways to find good people. One, start with the results and work backwards — don't say "I want a great marketer, I'll go to Nike"; find an ad you love and figure out who made it. Two, keep asking people to build your rolodex. Every company has a little mafia of talent — Uber has an ops mafia, Apple has a design mafia — and they tell you who the other good people are.

I'm the co-hiring manager for the top 200 people in the company. A lot of CEOs think their job is to hire their executives, and the executives hire their own teams. I think that's fatal. In theory you'd have people so good they can all hire their own people, but most entrepreneurs, if they have ten executives, would be lucky if two or three can do that without help. I used to say my executives should hire people so good they'd never work for them without my help — if you can hire them without my help, we're not reaching far enough. The first and last call I make every day is to the recruiting team, and I still spend two or three hours a day on it. Every year I spend more time on recruiting and less on management, because the really good people are self-managing. If you have to manage people, maybe you should think about upgrading the talent.

Brian Chesky

The way to activate someone is to give them a problem or an opportunity and see if they can do it. People with a high level of agency will do it. I don't know how to teach motivation — I don't know that it can be taught. You can motivate people, but I don't think you can make an unmotivated person motivated. All entrepreneurs have the trait of being self-motivated. So it's about giving them a challenge, and then it's up to them to step in and activate.

Brian Chesky

Most of my heroes are artists. I'll pick four: Leonardo da Vinci, Vincent van Gogh, Walt Disney, Steve Jobs. What did they all have in common? On the last day or the last week of their lives, they were working. Leonardo carried the Mona Lisa with him until he died — and he didn't paint it for adulation, because he never showed it to anyone. Van Gogh sold one painting in his life and died an obscure artist in a cornfield; he did it because he loved it. Walt Disney, on the last day of his life, lay in a hospital bed dying of lung cancer, his brother Roy rubbing his cold feet, looking at the grid of ceiling tiles and imagining Disney World. Steve Jobs, in his last couple of weeks, was still looking at products and marketing. Some people see that as sad — they weren't with their families. Van Gogh and da Vinci didn't have families; Steve and Walt did spend time with theirs. But I don't see it as sad. They did what they loved, like Mozart and the great artists in history.

My motivation is the motivation of an artist — to create something great. I'd like to be successful, I want our shareholders to get a return, I want employees to feel they're at a great company, I'd love to make a huge impact. But mostly I just want to make something. I feel like I'm a designer more than a CEO, and I might have been afforded one of the biggest canvases of any designer in human history. Usually designers aren't given this many resources — it's almost like a glitch in the system, some error that let me get resources I wasn't supposed to get. And I'm not letting go. My motivation is that of an artist: I just want to make incredible things.

Brian Chesky

I think everyone's an artist. All children are born artists; the problem is to remain 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. When you hear "creator" you think social-media performer, but that's just one way to create. Now creator can mean create, make. Everyone can make now. This seems like the most exciting time to be alive in human history — AI is probably the greatest invention in history, the ultimate creative expression, the ultimate platform shift. At the most recent Y Combinator dinner I looked at all the entrepreneurs and said I was jealous. Two or three years ago I used to say I'd never do it all over again, because I was afraid I'd never have this level of success again. Part of me wishes I could be 26, get rid of all the success, and see what's possible again. And then I realised age is just a number — I can still act like I'm 26. I'm still young, I've still got more in me. We're all just getting started.

Brian Chesky

The biggest gift anyone's given me is to believe in me. When I was 16 I transferred to a public high school. I was into art and pretty good, though I didn't know how good. I had a teacher, Miss Williams, who believed in me and told my parents I'd 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 good at hockey, and I wish I could have made my dad proud there. That belief set me on a path; I decided to go to art school. And I realised I could decide to be happy the rest of my life.

I came to Silicon Valley and met Michael Seibel and the guys at Justin.tv, and they believed in me — they were early YC people. Paul Graham made an exception to let me into Y Combinator; he almost never funded non-engineers, and he thought the idea wasn't good. He said, people are actually doing this? I said yes. He said, what's wrong with them? But he believed in me. My investors believed in me. Joe and Nate believed in me. I had no business being a CEO, and somehow they believed in me. I wouldn't be here without the generosity of people believing in me and helping me. The greatest gift I can give back is to believe in others and not pull the ladder up behind me.

I had the privilege of joining the Giving Pledge, where you write a letter, and mine said: if you asked my high school teachers who'd join the Giving Pledge, they wouldn't have guessed me. My life philosophy is that we all have unknown potential, and we tell ourselves stories about what we're capable of. Someone once asked John Wooden the secret to success, and he said he only asked his players to do their very best. The catch is that he saw potential in people they didn't see in themselves. That's my management philosophy: when I tell someone it's not good enough, I'm not saying you're not good enough — I'm saying I see potential you don't see in yourself. That's the most motivating thing you can do, and people will climb a mountain for it.

The most important person you can believe in is yourself. A lot of us who are entrepreneurs were driven by insecurity — some hole, something in our childhood we wanted to prove. Then you get really successful and you still have impostor syndrome. A lot of the path to happiness is learning to believe in yourself. For me, I only believed in myself long after other people believed in me, and now my gift is to try to give that to others.

Brian Chesky

Thank you very much. Thanks, man.