Brian Chesky’s new playbook

1. 0:00 – 5:18

   Brian’s background

   1. BCBrian Chesky0:00

      Way too many founders apologize for how they wanna run the company. They find some midpoint between how they wanna run a company and how the people they lead wanna run the company. That's a good way to make everyone miserable because what everyone really wants is clarity, and what everyone really wants is be able to row in the same direction really quickly. And so I basically got involved in every single detail and I basically told leaders that leaders are in the details. And there's this negative term called micromanagement. I think there's a difference between micromanagement, which is like telling people exactly what to do, and being in the details. Being in the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do, but if you don't know the details, how do you know people are doing a good job? People think that great leaders' job is to, like, hire people and, and just empower them to do a good job. Well, how do you know they're doing a good job if you're not in the details? And so I made sure I was in the details and we really drove the product.

   2. LRLenny Rachitsky0:58

      (instrumental music) Today my guest is Brian Chesky. Brian is the CEO and co-founder of Airbnb, which he started in his apartment with his co-founders Joe and Nate, and has turned into an $80 billion global business with travelers and homes in 220 countries. I was very lucky to get to work with Brian for many years, and my sense is if you ask people who they consider the most inspiring tech or business leaders today, Brian would be right near the top of that list. In our conversation, Brian shares an in-depth explanation of what's happening with product management at Airbnb, which caused quite a stir in the product world when he talked about this previously. We also get deep into Brian's new approach of how he runs Airbnb, including shifting away from traditional growth channels like paid growth, and instead betting that if they just build the best possible product and tell people about it, growth will happen. Also, how the product team now operates, including having just one single roadmap across the entire company and Brian staying very close to every design and every feature. We also get a bit into his personal life, including how he finds balance and avoids burnout, how he continues to learn himself so that he can stay ahead of the business and its growth. This is a very special episode for me, and I'm thrilled to bring you Brian Chesky after a short word from our sponsors. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted private supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions, and bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you can meet them at Sidebar today? Jump the growing wait list of thousands of leaders from top tech companies by visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and road mapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds. And it's all built on Jira, where your engineering team's already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback, and insights in Jira Product Discovery for free. No catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny. Brian, thank you so much for being here. Welcome to the podcast.

   3. BCBrian Chesky5:04

      Well, thank you for having me.

   4. LRLenny Rachitsky5:06

      Did you ever think when I left Airbnb, one, that I would have a podcast, and two, that you would be on my podcast?

   5. BCBrian Chesky5:12

      I had no idea you would become a podcast host and that you would have such a successful podcast. But yeah, congrats on everything. This is awesome.

2. 5:18 – 9:21

   The current structure of product management at Airbnb

   1. BCBrian Chesky5:18

   2. LRLenny Rachitsky5:18

      I appreciate it. Congrats to you too, Brian. Things seem to be going great.

   3. BCBrian Chesky5:21

      Yeah (laughs) .

   4. LRLenny Rachitsky5:21

      I'm excited that you're here.

   5. BCBrian Chesky5:23

      Yes.

   6. LRLenny Rachitsky5:23

      I want to start with the elephant in the room for a lot of listeners of this podcast. Uh, what is going on with product management at Airbnb? You made some comments at Figma Config, and a lot of people got this impression that you eliminated product management at Airbnb. And I've heard from a lot of product execs having boardroom conversations as a result of that, and they were trying to decide, should we remove product management from the company? Should we significantly cut product management? So I'm just curious to hear from you. What is the latest on your thinking on product management and what's happening with product management at Airbnb?

   7. BCBrian Chesky5:56

      I spoke at Figma, you know, like four or five months ago. I spoke to a room of designers. I then, uh, got off stage.I saw people, somebody Tweet that said something, uh, to the nature of, that I said I got rid of the product management function. All the designers in the room started cheering.

   8. NANarrator6:14

      (laughs) That's right.

   9. BCBrian Chesky6:15

      So I wanna, I wanna, you know, I wanna talk about two things. What I actually meant, 'cause I didn't actually get rid of the people, and also, why did the people in the room cheer? 'cause that's also, like, a thing we should ask ourselves, and I hope everyone listening to this podcast should understand, where did that place come from, that 5,000 designers in a room cheered because I thought I eliminated the existence of a function? 'Cause if I said, "I eliminated engineering function," no one would have cheered. It was specifically that function. So I wanna talk about what that might mean. It wasn't the people. It's the way they're working together. So we don't have any longer the traditional product management function as it existed with, when you were here. But we didn't get rid of people helping drive the product. What we did is we combined what one might call the inbound product development responsibilities of a product manager with the outbound or marketing responsibilities of product marketing. That's the first thing we did. The second thing we did is we off-boarded much of the program management functions that product managers may do to actual program managers. A lot of people with a product management title are actually program managers. So we actually started off-boarding some of those responsibilities to program management. The last thing we did is we made the group smaller and more senior. So we don't really have a lot of junior product marketers. So their most senior people are called product marketers, but everyone has to understand how to talk about the product. So the basic idea is this, you can't build a product unless you know how to talk about the product. You can't be an expert in making the product unless you're also an expert in the market of it. And a lot of companies, what they do is they ship a product, it doesn't work, and they say, "We tried that. It didn't work." And if you say you tried it and it didn't work, my question is, was it a bad product, a bad strategy, or bad execution? Maybe it was a really well made product but you had no distribution plan, you had no way to talk about the product. If you build a great product and no one knows about it, did you even build a product? So that is essentially what we do. We have a much smaller function, the people are much more senior. They have a re- much more responsibility. The other thing though is that they do not control or drive designing or engineering. We are a fairly purely functional model. They manage by influence. They do not have control. Now, you might ask, like, how does that work in a company where people can only manage by influence? Here's the amazing thing. We built and designed a company where you can manage by influence and no one has to like you. You don't actually have to, have to win people over. Oh, and the last thing I want to say is, why did 5,000 designers cheer when the people thought I removed the product management function? Because I'm gonna say, I, I don't know, I don't know if I can speak on behalf of all the designers, but having talked to a lot of designers, I think designers in the Valley are very, very frustrated with the product development process. Not to say the product managers, but they're extremely, um, frustrated. And I think a lot of designers feel like they're compromising. Many designers I know, heads of design, well-known heads of design, I told them they're not designers, they're design administrators. They're running a design service organization

3. 9:21 – 12:20

   How fast-moving companies become slow-moving bureaucracies

   1. BCBrian Chesky9:21

      because Silicon Valley often treats design as a service organization. You know, like design is catching things before it goes out the door. It's not actually typically part of the development process. And I think this is not just bad for design, it's bad for product managers and engineers, 'cause we all want to build the best products. And one day you wake up and a variety of phenomenon might have happened, and if people are watching this from a large company, here might be some of the characteristics. The first thing you notice is that these different groups might be running on slightly different technical stacks. That's the first problem. And they may actually be require, uh, accumulating technical debt. The next problem you'll see is that there's a lot of dependencies. So five teams are going separate, different directions, but they all need a payment platform. And so then once it happens is that the teams that everyone's dependent on get this backup, like a deli, and people are going around the block. And then they are basically, like, at some point, they just kind of give up. So then the teams that are dependent on other people say, "Give me the resources and I'll build this group myself." So instead of five teams going to marketing to get a campaign or to leverage some service, they start building their own marketing departments, their own groups. So now they're really becoming separate divisions. And this is where division comes from. Now, once you have a division, your division is su- as successful as you are a priority. So now you have to advocate for your division. So there's a lot of advocacy. If you have dependencies, you've got to persuade people by building relationships. And so the people that are liked, that build the best relationships, are the ones that get the most resources. And that creates what we call politics. And so now politics have brewed in the company. And suddenly people gets more subdivided, more subdivided, subdivided, and that creates another problem which we call bureaucracy. And that bureaucracy means it's hard to know who's doing what. You can't, like, people are going in different directions, and that creates a lack of accountability. When there's a lack of accountability, then there's a sense that what I do doesn't matter, and that creates complacency. And then suddenly a fast-growing company becomes a big, slow-moving bureaucracy. This is a general arc of what ends up happening. And then you end up having this situation where a company's done like 10 marketing efforts but no customer's heard anything. They have thousands of engineers, they shipped all these products, but a customer can't tell you a single thing you did. And, you know, marketing and engineering, like, don't talk to each other. It's not even they hate each other. They're like in different universes. I've always said that the health of an organization, one simple heuristic is how close is engineering and marketing. And marketing is, uh, a lot of companies are like the waiters, engineers are like the chefs, and the chefs yell at the waiters when they go in the kitchen. In fact, the waiters are the ones talking to the customers all day and they also know how to sell things. So you really want them being enjoined at the hip, and you want engineers to be thinking about maybe how to talk about the products that they're building. So...This is the problem that we had. And

4. 12:20 – 13:50

   Brian’s thoughts on performance marketing

   1. BCBrian Chesky12:20

      I also... The, the other thing we were doing is, as you know, Lenny, we're spending a lot of money on performance marketing. I don't think performance marketing is a bad thing. I think of performance marketing as a laser. Uh, a- actually, my co-founder, who you obviously know well, Joe, used to have this metaphor of lasers, flashbulbs, and chandeliers. If you want to light up a room, performance marketing's a laser. It can light up a corner of a room. You don't want to use a bunch of lasers to light up an entire room. You should use a chandelier. And that's what brand marketing is. But if you do need to laser in and balance supply and demand, then performance marketing is really good. It literally lasers in. Performance marketing, though, doesn't create very good accumulating advantages, because it's not an investment. Now, if you want to build it permanently, like Booking.com, if you have a really high RO- ROI, now you can have a performance marketing arbitrage business. But assuming you don't want a a arbitrage business, you actually need to be investing. And so we think of marketing as education, that we're educating people on the unique benefits. So a lot of companies don't do product marketing. They do brand marketing, which are ads about the app, or they do performance marketing. But they're never really educating people about new things they're making and shipping. And because no one's marketing new things or shipping, there's no purpose to ship new things, 'cause you ship new things and people don't know about them or use them, or they're not educated. And so you try these big new things. People don't adopt them immediately, so then you get more and more incremental.

5. 13:50 – 15:30

   Airbnb’s rolling two-year roadmap

   1. BCBrian Chesky13:50

      Now what we do is we do... We have a rolling two-year roadmap. We don't even really do an annual plan. I mean, we... As you remember, Lenny, when you were at Airbnb, we would have like three-month planning cycles. Now, planning cycle is just a budgeting cycle, and it's like most people only spend a week or two on it. Some don't spell any time on it. And we have a rolling two-year product plan, the strategy, product strategy roadmap, that gets updated every six months with releases. We release products, um, every May and every November or October. Obviously, we did one today we can talk about. And the entire company works together. They row in the same direction. And the product management also does the product marketing. So they're figuring how people are gonna learn about it. They're doing the demos. They're understanding the story, the videos. They're, you know, figuring out all the customer touch points, making sure everyone understands it. Our product marketing works with communications. We, like, work months ahead of time on all the different assets. And when we're working on a launch, one of the first things we'll do is start figuring out what the story is. And the story will often dictate the product, because ultimately you have to tell the story to people, but a story also is a really helpful way to develop a cohesive product, right? We wanted a company where 1,000 people could work but it looked like 10 people did it. And so... Sorry, that was a bit of a brain dump, but that is a little bit of a universal theory for how we develop products now. I mean, I could go into a lot more detail, but I probably will stop there.

   2. LRLenny Rachitsky15:23

      (laughs) That was amazing. You touched on all of the things I want to talk about, so I'm gonna-

   3. BCBrian Chesky15:27

      Oh, geez, so we can go deeper and deeper, 'cause the rabbit hole goes deep.

   4. LRLenny Rachitsky15:29

      Yeah. Exactly,

6. 15:30 – 18:34

   Brian’s journey as CEO in a growing company

   1. LRLenny Rachitsky15:30

      exactly. So I'm gonna pull on a couple threads. The first is this idea of a single roadmap you talked about, and what this reminds me of is, I was talking to another very prominent CEO of a public company, and he pointed out that there's this cycle that he sees a lot of founders go through where they initially run the show. They're in charge. They tell people what to build. And then over time, they're encouraged to delegate and to empower, and it leads to a bunch of optimization work and small thinking maybe, and you talked about bureaucracy and politics. And then eventually, you realize, "I need to take the reins again and drive the ship and kind of take back control of what's happening." And it feels like you went on that journey.

   2. BCBrian Chesky16:08

      That's exactly how it went, and that's how it goes almost at every company I've heard of. By the way, I think that like many years ago, I remember, I think reading a blog post by Ben Horowitz saying that a lot of people tell product-led founders or engineering-led founders to step away and delegate their product to other people, but suddenly they've delegated away the thing they're best at, the thing that is hardest for them to replace. So we don't have a chief product officer title, but if we had one, it would be me, you know? They, they... I wouldn't have a chief product officer. I think the CEO should be basically the chief product officer of a product or tech company. And if the CEO is not the chief product officer, then I don't know if they're a product or tech-led company. Maybe, maybe that's okay if they're an ops company or if they're a marketing company or if they're, like, not a tech company at all. But ultimately, I think this founder CEO should be that person. So, when we were starting Airbnb, it was probably the three of us, you know? As you know, like, I think Airbnb was a unique situation where it was three of us. I don't think any of us was that dominant. I probably played the closest thing to the role of the, the people listening, like the closest thing to the role of the product manager. But again, I did marketing, I did design, I did, like, ops. I did, like, kind of a little bit of everything. So I was basically everything but engineering. And then as we grew, I started getting more and more hands-off on the product. And I always remember, L- Lenny, and you might remember this, there was this paradox where the less involved I was in a project... I mean, there was... There... Let me be clear. There were times I inserted myself and dysfunction occurred. That is absolutely true. And that was just a learning experience for me. But there's this other scenario where the less involved I was in a project, the more spin there was, the less clear the goals, the less advocacy the team had, the less resources, the fewer resources they had, and then therefore the slower they moved. And the slower they moved, the more they assumed it was 'cause I was too involved, right? 'Cause people assume that, that our natural equilibrium is to move fast. So if we're moving slow, it's because of an over-involvement in leadership. And therefore, I would get less involved. I would give teams more control. I would give the teams more empowerment. And the more I kept giving people what they asked for, initially they may have been happy, but the outcome of it was always... It seemed weirdly like they got less of what they wanted. They wanted to move faster, so I'd power them and they'd move slower. And again-How that happened is what I described, that you- you- you end up in a situation where you're delegating

7. 18:34 – 20:30

   Best practices for A/B testing

   1. BCBrian Chesky18:34

      down. So I think that things were getting worse and slower and slower and slower, 2015, 2016, 2017, 2018, 2019. And by 2019, we're spending a billion dollars on AdWords. We weren't really, like, investing in the brand. We were doing a huge amount of A/B, uh, testing. I think A/B testing is important in times. But like, let me actually- let me- let me- let me- let me clarify A/B testing. We don't test blue versus green. We have a control and a treatment, like I think we did when you were here. So we have a design. We might do a holdback occasionally to see how the thing is working. But if we do an A/B test, there has to be a hypothesis. If we don't have a hypothesis and A is better than B, then we're stuck with B. And that's like a really, really big problem and never- you can never change it. And imagine ten teams doing A/B testing and, like, imagine if UE designed software the way we designed a house or designed a house the way we've done software. And we A/B test a sofa and we said like, "Well, how does this sofa work?" And it seems like with this sofa that we've A/B tested, people spend more time in the living room, so therefore, like, people are gonna like this room better. But actually, the sofa has a relationship to the end stands, which have relationship to the lamps, which have a relationship to the carpet or the rug, which have a relationship to the television, which have a relationship to the house and everything else. So you have to think about the whole cohesive system. And I started realizing that, I remember working with S. I asked one person on your team, somebody you know well, I'll... and I asked him, I said, "Why is there... I feel like I opened our app and the product hasn't changed in like four years." I remember saying this like 2018, 2019. And he- this person described that, you know well, as just the way we were doing things, the initial way we're doing things to move fast had made us move slow. So we end up doing

8. 20:30 – 23:18

   Who inspired Airbnb’s new direction

   1. BCBrian Chesky20:30

      is it was now late 2019. I'm- don't know what to do. I'm like the product is slow, the app seems to not change, cost are rising. I keep adding more people. There seems to be more, like, politics. By politics, I mean advocating for like individual interests rather than the whole of the company. More bureaucracy, meaning like meetings about meetings about meetings and a lot of dependencies people were describing working 80 hours, getting 20 hours of productive work done, which is like just like a crazy ratio a week. And I didn't really quite know what to do. And then right before the pandemic, I meet two people that really affected how I thought about things. The first is Hiroki Isai. Hiroki now works at Airbnb. He's one of my executives and actually product design, product marketing design and marketing reporting to him. And he was a creative director for Apple. So he worked for Steve Jobs, was like basically dotted line to Steve for many, many years, came from graphic design, eventually ran all of marketing communications. Then at Apple marketing communications, they actually like- they actually designed the app. They made the app. They designed like all the marketing touch points for the store, right? So it wasn't just ads. It was like every brand touch point, they were responsible. So everything flowed through marketing. And so marketing became the governing factor that made everything really organized. I met another person or got reacquainted a person named Jony Ive. And Jony Ive was the head of industrial design and chief design officer at Apple. And they described this way of running a company that was totally different than the way that I was running it. It was basically the way that Steve Jobs ran Apple from about 1998 till he died in 2011. Apple somewhat runs it this way today, but they are semi- div- like the services is turning into a division and they are just so big that I think it's, you know, not a one to one anymore, but they are still technically run this way. And I had this image of not being divisional 'cause we were running like t- we had ten divisions. We had a flights division and, you know, we had a homes division which was divided into ProHost and Core Host and Luxe and we had business travel and we had like, you know, a magazine and we had experiences and we had dot org and we had China. So we had like these ten different divisions all going in ten different directions. And I created this culture where everyone would be a business manager and- or a- a- a j- you know, business leader, general manager, which made them want to create many general managers, right? And so the company kept getting subdivided, subdivided, subdivided. And that made it very, very difficult to turn. And this was all about me delegating responsibility. The problem is, if you're running a divisional company or a product led founder, you're kind of, what are you doing? Like, strategy, capital allocation. My job went from proactive to very reactive. I was reacting to a lot of things. I was in a lot of meetings trying to adjudicate different issues between

9. 23:18 – 24:51

   The first changes Brian implemented at the onset of the pandemic

   1. BCBrian Chesky23:18

      groups. So then the pandemic occurs, and I have this image on my mind, it's like I have this dream that I could run a company much more like a startup. I remember going on a walk with Joe and Nate in Bolinas. It was October 2019, and I told them I had this dream that I left the company ten years ago and you- they just asked me to come back. And I said, "I was horrified at what I found." And they said, "Well, what did you find?" I said, "I found a company that on the one hand had amazing culture and people with a great mission, with a brand people really loved. But the- we lost our design roots. You know, we weren't investing in the long term. We were obsessing over hitting metrics. We didn't actually have any cohesive understanding of what we were doing. It was really hard to get work done. A lot of the great people were leaving and cost was rising and growth- growth was slowing." And that was exactly kind of what was happening. And then the pandemic occurred and we lost 80% of our business in eight weeks. And then suddenly we're like, oh my God. Like, I remember having- basically staring into the abyss.And luckily, I've never had a near-death experience, but the way it's been described to me is it's like your fli- life flashes before you a- your eyes and you have clarity. And that's what happened to our business. We had a near-death business experience and our business flashed before our eyes. And so suddenly, I basically got into action and I said, "I'm gonna run it this other way, where I'm gonna get back and involved in the

10. 24:51 – 30:15

    Why founders should be “in the details”

    1. BCBrian Chesky24:51

       details." And by the way, Lenny, here's the funny thing. Before the crisis, a lot of people felt like I was too involved in different areas. Once the crisis happened, guess what happened? People were like, "What do we do?"

    2. NANarrator25:01

       Hmm.

    3. BCBrian Chesky25:01

       "We need you more involved." And so I got more involved. And when I got involved, I made the following changes. The first thing I did is I took like, I said, "Everything we're doing has to be written down and put into Google, Google sh- like a Google Sheet." It turns out people couldn't even write down everything they were doing. I remember one person told me, "You, you think, uh, we're doing too many things for me to ever be able to document." I'm like, "What?" But anyways, we eventually got everyone to write everything down and I said, "Okay, we can do about 20% of these things." And so if everyone says, "Oh, I'm, I'm, I..." Airbnb is simple. I'm only doing three things. Yes, but you're one of, like, a thousand people. So actually, we're doing 3,000 things. So instead of one team doing three things, three teams should do one thing. So we totally cut down the number of projects. We removed layers of management. I wanted to be as few layers as possible from leaders of the team. We went to a functional model. We went back to a startup. So we said, "We're not gonna have divisional leaders. We're gonna have design, engineering, product," and, which turned into product marketing, "and marketing and communications and sales and operations, all the functions of a startup." I said, "We're gonna have fewer employees. We're gonna have fewer, more senior people." There's a great saying that the best way to slow a project down is add more people to it. And so we felt like very few employees, we have fewer than 7,000 employees today. As a relative comparison, I think Uber has 30,000.

    4. NANarrator26:21

       Hmm.

    5. BCBrian Chesky26:21

       And it's not to say they're big, it's just to say that's how small we are. And we've really benefited from having not a lot of employees. So we had, we made sure that every executive was an expert in their functional domain. So you know how there's a lot of engineering managers that aren't that technical?

    6. NANarrator26:36

       Mm-hmm.

    7. BCBrian Chesky26:36

       Or maybe not a lot, but there they exist. Or there's designers, but there's design leaders who, uh, lead the people. A design leader's job should be managing the design first, the people second. That's what J- Jony did or, like, they're, they're interchangeable. I, I could never imagine Jony at Apple just being a manager of people. He was looking and designing the work with the team. How do you manage the people without managing their work? How do you give them development if you're not in the details with them on the work? So the same thing is true. So people had to be experts. Everyone had to be an expert. I stopped pushing decision-making down. I pulled it in. I created one shared consciousness and I said, "The top 30, 40 people in the company are gonna have one continuous conversation. Metrics are gonna be subordinate to the calendar." So we're gonna have a roadmap. It's gonna be a two-year roadmap. We'll update the roadmap literally every month. People may wonder, "Well, like, what if the world changes?" Yeah, it changes every day. So the roadmap's something where the next month doesn't change, but two years out, it changes. It's a rolling roadmap. And by the way, if Ukraine, like, gets invaded and you wanna, like, provide housing for refugees, you can still pivot people and adapt very quickly. We housed 120,000 refugees. So you still keep a reserve of resources to be able to pivot and do things, 'cause there's always unexpected events. I created this new function called product marketing. We basically described what that is. I made the group much smaller. I took a lot of product managers, I reassigned as program managers. I had many of them trained in actual program management, 'cause their roles got much bigger. U- um, program management at Airbnb is a high-status job. At a lot of companies, it's like a coordination job. At Airbnb, we said, "Because we're gonna do launches, it's high-status." We said, "We're gonna do two launches a year and you can't ship something unless it's on the roadmap." So every single thing in the company, with the exception of some infrastructure projects, have to be on the roadmap. And then I'm gonna review all the work. And so we create the CEO review schedule, where I said, "I'm getting back in the, involved in the project and I'm gonna design, I'm gonna review all the product and all the marketing." So every project I would do review either every week, every two weeks, every four weeks, every eight weeks, or every 12 weeks. There'd be a cadence. And then I had a head program manager that would score all the projects, either they're green, yellow, or red. Meaning, they're on track or not on track to ship. Whether we thought they were work, we don't know until after we ship it, but I used the reviews of the work every single week. And the reason there's not a lot of bureaucracy and the reason you don't need any influence at Airbnb is I'd review the work and if something wasn't happening, then I would, like, stop the meeting and say, "Why isn't this happening?" And, like, we would all get together. And so you couldn't have a situation where, like, a team wouldn't collaborate. And so it would be like I could then feel the work of an, of a individual engineer, 'cause imagine it's like we're a car company and I, I see the car prototype every week and I notice there's a, there's a, there's a, something about the tire is off. Now I m- I can identify the individual person who was blocked. So every week, I would see, I would try to see the equivalent of at least a semi-assembly of the entire new product we were working on, which allowed me to identify with teams the different bottlenecks happening in the company. And the reviews were the thing that allowed us to dictate the pace. And so because we had unusual week, re- re- all these reviews, I didn't need to mandate people going back to an office. I didn't really care where they worked, because I could track how well they were working because of the review cycle. I, it's... So these were, these were, like, some of the changes that we made.

11. 30:15 – 31:38

    Airbnb’s marketing, communication, and creative functions

    1. BCBrian Chesky30:15

       We also started really building out much more of a marketing, communications, and creative function. We built our own in-house creative agency. So we use production partners, but we don't use Wieden+Kennedy or Schachter any of those anymore. We actually built our own in-house agency, so to speak, which is a creative group. The creative group...... does a lot of the- the- the- not just the ads, but the creative on the product. So we got really, really functional. We got rid of a function called UX writing and we combined it with marketing writing. We said, "Wait, aren't the best writers... like, why don't we just have the best writers do everything? Why is UX writing a separate function?" Because actually, the emails, the app, the ads should all be one voice. Now, there may be people that come from a different background, like there are people that come from UX, but they all roll up to one function of writing. And writing should not go to design. Writing should go to a function called writing. Unless you want your head of writing to report to design, then that doesn't make sense. So we- we- we really mak- made a lot of those changes. Just to round up the question that you asked, I think that like way too many founders apologize for how they want to run the company. I don't know why they do, but I think they apologize for how they want to run- run the company. They basically find some midpoint between how they want to run a company and how the people they lead want to run the company.

12. 31:38 – 34:15

    Advice for founders on how to lead

    1. BCBrian Chesky31:38

       If you're a founder, what I would tell you is, the problem with finding a negotiation between how you want to run the company with the people you want is that's a good way to make everyone miserable. Because what everyone really wants is clarity. And what everyone really wants is to be able to row in the same direction really quickly. And also, if you try to appease employees, they may not even be there for- the whole time. So we have entire projects at the company where somebody advocated to do it, it was a big commitment, and then they left, and now we're still doing the project they advocated for. So it really has to be something that everyone wants to sign up for, not just the person who's there because they might not always be there. And so you know, I basically got involved in every single detail and I basically told leaders that leaders are in the details. And there's this negative term called micromanagement. And I think, I think there's a difference between micromanagement, which is like telling people exactly what to do, and being in the details. Being in the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do. But if you don't know the details, how do you know people are doing a good job? People think that great leaders' job is to like hire people and- and just empower them to do a good job. Well, how do you know they're doing a good job if you're not in the details? And so I made sure I was in the details and we really drove the product.

    2. LRLenny Rachitsky32:57

       (instrumental music) This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at GetEppo.com/Lenny and 10X your experiment velocity. That's GetE-P-P-O.com/Lenny.

13. 34:15 – 38:48

    Tips for implementing Airbnb’s business methodology

    1. LRLenny Rachitsky34:15

       You guys found such a unique way of working. I've never heard of a company working in these ways, in so many contrarian ways. I think it's going to be a really interesting case study as things progress. Essentially, what you've done is shut down traditional growth channels, or at least limited them, paid growth and maybe SEO, maybe referrals, at least for a while, and you've kind of shifted to, "Let's just make an awesome product and tell people about it, and our bet is that what's going to grow." Do you feel like this can work for most other products? Or is there like a consumer specific opportunity? What advice would you give to founders that are thinking about, "Man, we should try something like this"?

    2. BCBrian Chesky34:53

       I think that this methodology can work for everyone, but I don't think you have to be as ideological or have to go all the way to 100. You- I still think growth channels matter. To be clear, we still spend money on performance marketing. We still do measure conversion and we will do some experiments. Think of conversion and growth optimization as like running a football down a field. And think of these big, like, leaps as passes. You should probably be doing 80% passes, 20% running the ball down the field. And a lot of companies they do 80% running down the- the ball down the field versus- and 20% passes. So I think that this methodology will work for everyone. I mean, here are the things I believe. I'll give you a checklist. Number one, I think that the CEO, unless they're not a product person, should think of themselves as Chief Product Officer and they should be involved in the product. Number two, if you're not functional, I would at least think about everyone being really close together. So here's another way of saying it, Lenny. Every product manager should be inter- interconnected and know what everyone else is doing. They shouldn't be independently siloed unless they really are running like separate companies or separate orgs and they have no dependencies. I think that every leader should be an expert in what they're leading. There should be no people managers in the entire company. And when I say people managers, meaning your only responsibility is people, not the work or not the domain, because you can't manage people devoid of their work. You know, imagine like a fire chief and they don't know anything about like putting out fires. Like, that's crazy. Like, you have to know the subject matter. People should aim to have as few people as possible on their team. I'm not saying eliminate people, I mean grow slowly and do not be reckless. Five teams should do one thing, rather than one team do five things. So that's just a metaphor. But people should work together. I think that people should consider doing launches. You can, by the way, ship every hour of every day, but then package it and tell a story if you wanna hold the product back. I think that teams should use data, but they should also use research and intuition. There's a designer called Charles Eames that said, "You can't delegate understanding." If you're gonna do AB experiments or measure data, you have to understand what it means. I think that you have to have an intuition. Intuition comes not from arbitrariness, it comes from understanding. I would make sure that you have engineering and design, ideally report to the founder product-led person. I would not have design under product unless you have an extremely good reason the product person kind of is a designer. I would try to think about product management expanding the responsibility and including distribution, understanding the customer and teaching people how to tell a story. I would try to make sure that the product managers are a combination of art and science. I do not think you want purely technical product managers doing things if they're gonna work with non-technical functions. Right? If they're only going to work technical functions, that's fine, but if they only work in non-technical functions, I think that's a problem. I wish to make sure that marketing and engineering are interconnected. I would make sure that you have as few layers between the CEO and other people. If you're a CEO, every direct to your direct should be a implicit dotted line to you. So I treat every direct to my direct as if they're a direct report, a dotted line. I don't try to conflict with the direction of my team, but I always want to know what another layer below me is doing. I think you should think of each release as a chapter of a story or like an episode of TV series, and you should think of your company in a five or 10 year story. You may not know where you are in 10 years, but you're telling this ongoing story. And most of all, I would say that everyone should row in the same direction. If there's only one thing I said in this interview today, which I'm not sure what it would be, but I, I, I think a good candidate is try to get everyone to row together in the same direction. Otherwise, why the hell are you all in the same company?

14. 38:48 – 41:47

    Airbnb’s winter release

    1. BCBrian Chesky38:48

    2. LRLenny Rachitsky38:49

       Speaking of rowing in the same direction, you had a huge launch today. I know you wanted to talk about it, your winter release, and it kind of is the culmination of a lot of the things you're talking about. I'd love to hear just some of the stuff you're launching.

    3. BCBrian Chesky39:00

       Let me just back up, Lenny. So-

    4. LRLenny Rachitsky39:01

       Yeah.

    5. BCBrian Chesky39:02

       ... you know this problem really like well. One of the best things about Airbnb is that we're this marketplace where guests and hosts come together and we have all this unique inventory and people, you know, list it on Airbnb. And every home is one of a kind and we have seven million homes and there's all this surprise and all this delight. The problem is that every home is one of a kind, and you often don't know what you're gonna get. And so a lot of guests have described checking into Airbnb as a moment of truth, where when you open the door that, you know, the home, you find out if the home is exactly the home that you booked. And this turns out to be a big problem for people wanting to book an Airbnb. And when we survey guests or people who don't use Airbnb, the number one re- the hotels are not as special, they're not as unique, but the advantage they have is you know what you're gonna get. You know exactly what you're gonna get. And so what we found is that reliability is Airbnb's Achilles heel, or at least it has been. That, you know, with hotels, you know what you're gonna get. In Airbnb, you don't always know what you're gonna get. And so we asked ourselves, what if we could combine the uniqueness of Airbnb with the reliability that you've come to expect in a hotel? And that's what we've done with guest favorites. Guest favorites are, you know, homes that guests in our community love the most. We took 370 million reviews on Airbnb plus millions of customer service tickets, plus all the host cancellation data, and we used all the signal to create the top two million homes, that this collection of two million homes that we call guest favorites 'cause it's the ?????? the guests rate the highest, we think combine the uniqueness of Airbnb with the reliability you've come to expect in a hotel. And I can't imagine there's a lot of use cases where you wouldn't want to book a guest favorite. We think that's also part of this broader system of ratings and reviews. You see, as you know, Airbnb is built on a system of trust and we invented this new way for people to trust one another, you know, at least at scale, you know, through, through, through living together certainly. And we felt like the rating and review system could use a little bit of an upgrade. So we obviously made some upgrades to ratings and reviews. And the final thing, and this brings up another point I might bring up, is we've completely overhauled the host tab. So, you know, one of the most important things when you get to an Airbnb is the listing is accurate. But the problem is that a lot of host listings don't have all the details up to, up to date. So they might not, like, describe perfectly their listing. They might not have filled up their amenities. They might not have a photo tour. And the reason why, as we were doing research, is 'cause they found it was hard to manage their listing. And it was hard to manage their listing because it was designed as this hodgepodge thing by different teams over many years.

15. 41:47 – 42:38

    Why Airbnb no longer has separate guest and host teams

    1. BCBrian Chesky41:47

       Oh, here's the other thing, Lenny. When you were at Airbnb, we had a guest team and a host team.

    2. LRLenny Rachitsky41:50

       Mm-hmm.

    3. BCBrian Chesky41:51

       We don't have a guest team and host team. We have a design team, we have a marketing team, we have an engineering team. The reason we don't b- break the app into guests and hosts anymore is because reviews affect guests and hosts.

    4. LRLenny Rachitsky42:04

       Mm-hmm.

    5. BCBrian Chesky42:04

       It turns out that almost everything involves connecting the guest and host, and if you have separate teams, they tend to have separate roadmaps that go in separate directions and they become incompatible. So we have product marketers that are responsible for guest and host things, but there's n- the, the designers are f- and the engineers are fairly fungible and they can move from project to project. And then we keep some people, especially the product marketing people, on a domain area, but we really wanna make sure that we have designers and engineers covering a much larger surface. And so, so that's what we

16. 42:38 – 45:36

    Brian’s thoughts on design trends

    1. BCBrian Chesky42:38

       did. We have this incredible new tab called the listing tab that we designed. It's quite possibly one of the nicest things we ever designed. If you go to my Twitter account, you'll see a little sizzle reel from some of the design we've done. By the way, the design is a whole new aesthetic.I'd like to, like, make the announcement that I think flat design is over or ending. You know, I think if you remember the 2000s was dominated by skeuomorphism. The 2010s have been dominated with the launch of iOS 7 by flat design. And I think we're gonna move back into a world with color, texture, dimensionality, more haptic feedback. But I don't think it's gonna be skeuomorphism where it pretends to be like a wood grain to reference like a dashboard or leather. But I think it's gonna have a sense of dimension. I think the reason why is we're spending more and more time on screens, and we want the screens to replicate some of what we see in the natural environment, light, texture. I think it's more intuitive. It's more playful. I think AI allows the development of more sophisticated interfaces. People and AI are gravitating to image generating art that has got more, uh, dimension to it. And so I think that we've, we've really started to push this more three-dimensional colorful aesthetic that I think, I think is gonna be where a lot of interface design is going. And we built this AI powered photo tour where we created our own AI computer visioning language that we trained on 100 million photos. And it can basically scan all your photos and organize them by room. So that's what we did today. Maybe just to round it up, what I would say is that none of this would've been possible in the old way of working. You know, we could have theoretically launched a lot of these features, but you know, really getting them to work together has been key. And guest favorites has required the guest, uh, people, you know, you know, you have to work with guests. You have to work a host. You have to essentially, you know, you know, you have to, uh, like figure out how to communicate to the market. So it's a much more integrated approach.

    2. LRLenny Rachitsky44:41

       The designs you talked about, they are incredibly cute. You tweeted a little video of a lot of them, like the couch with little textures on it.

    3. BCBrian Chesky44:48

       Yeah.

    4. LRLenny Rachitsky44:48

       And, uh, uh, it is really cool. Also, the listing tab. I think people that aren't hosts don't understand how important the listing experience is to a host.

    5. BCBrian Chesky44:56

       Oh, totally.

    6. LRLenny Rachitsky44:57

       That's like, I think, how many hosts are there? 7 million, something like that?

    7. BCBrian Chesky45:00

       There's, there's, there's 7 million listings. Yeah.

    8. LRLenny Rachitsky45:02

       Got it.

    9. BCBrian Chesky45:02

       Over 7 million listings.

    10. LRLenny Rachitsky45:04

        Yeah. And so that's like the home base. That's like the small business platform for millions of people. And so I- I worked on the host sites. I have a special place in my heart for host features. And I feel like travelers don't really appreciate the value of that part of the product.

    11. BCBrian Chesky45:17

        Well, yeah. You, you did some amazing work there. Yeah. I think that, like, the big lesson, Lenny, the other thing we learned is to create a great guest experience, you need great hosts. And to have great hosts, you need great tools. And so if you want to create a great experience for guests, it often starts with building great tools for hosts to enable

17. 45:36 – 45:57

    The importance of empowering hosts with great tools

    1. BCBrian Chesky45:36

       them to provide a great experience for guests. And so that was one of the theories behind the listing tab is we're gonna build great tools for hosts. They're gonna love it. And we also felt like if we put care in design of our app, that hosts are gonna see that. And that they're gonna actually put care into hosting, even more than they already do. And they- they do put a lot of care in now.

    2. LRLenny Rachitsky45:55

       Speaking of great products,

18. 45:57 – 50:05

    How setting ambitious goals improves team performance

    1. LRLenny Rachitsky45:57

       a defining characteristic of Brian Chesky in my mind is how big you make people think, how you push people to think bigger. Memories I have of you is in meetings we present our goal. And you're always saying, "How do we 10X this? What would it take to 10X this idea?" And somehow we often hit these crazy goals after you 10X them or sometimes just double them. (laughs) What have you learned about just the power of setting really ambitious goals, but also finding the balance with not demoralizing people if they don't hit these really ambitious goals?

    2. BCBrian Chesky46:32

       As you know, there was a, there was a saying inside of Airbnb. It was add a zero.

    3. LRLenny Rachitsky46:37

       Mm-hmm.

    4. BCBrian Chesky46:37

       Add a zero at the end, which is to make, to imagine something order manage bigger.

    5. LRLenny Rachitsky46:41

       Mm-hmm.

    6. BCBrian Chesky46:42

       The exercise isn't necessarily to say, if people say they want to hit a goal, I say, "Okay, I added a zero. You have to hit that goal." It's more the exercise of what would it take to be 10X bigger or do something 10 times better? Because what you find is when you push people, they will sometimes think about the problem differently. And one of the best ways to get unstuck from a problem is to imagine a 10X scale or 10X better or 10X faster where you can't do the current process to do it. You have to think differently about the problem. And to think differently about the problem means you have to deeply understand the problem. And to deeply understand the problem, you have to break it into its components. And we might call this like first principle thinking. What are the foundational elements that comprise this problem? And how can we construct them? So the first thing is I think by adding a zero, at least conceptually for teams, it helps them understand a problem. The second is I think one of the most important things for a founder or leader to do is set the pace of the team. I think the pace of the team is one of the most important things you can do. And that pace is sometimes governed not by how hard people work, but how decisive they are. If you want to improve the speed of a company, then make faster decisions. And that fast decisions come from a bias of action. If we're in a meeting, we don't just say like, "Okay, like let's circle back on this next week." No, "We'll have it done by next week. Let's stay in this meeting till it's done. What are you doing?" Have a bias for action. Who's responsible? Okay, what are you doing? Okay, let's check in an hour. I'll call you in the morning. Okay, how will we do this? And so you end up getting three months of work done over that period of time. But the last thing I'll say about adding a zero, Lenny, is I remember there was a story about a great, uh, basketball coach named John Wooden. He was one of the, uh, winningest basketball coaches, I think, in college basketball history. Perhaps the greatest. And someone asked him once, and I'm gonna paraphrase what he said, like, "What is your secret to success?" And he said that, you know, "I just ask my players to do their very best." And I remember thinking to myself, that doesn't sound like the secret to success, asking people to do their best. But there was an implicit thing that he didn't say, which is that he saw potential in people that they never saw in themselves. And so the role of a leader...... is to see potential in people that they may not even see in themselves. You know, when I tell somebody, "It's not good enough," either I'm saying you're not good enough, or I believe that you have more potential than you're showing me. So in other words, you can push a team and they could feel demoralized 'cause they can feel like what they're doing is not good enough if they have a fixed mindset. Or you can create a growth mindset organization where the more I'm involved, the more I say, "You can do better," it's 'cause the more I believe in you and I know that you have more in you. And the way to know if a team could do better is if their life depended on it, could they do it? And Andy Grove used to say that there's competency and motivation. And motivation is if their life, n- not literally dependent on it, but, like, if it was a crisis or if it was, like, a defining moment in their lives. I think the job of a leader is not to make it life and death, that's too far, but to be able to motivate a team, to see potential in them that they don't see in themselves, and to really push them. To set a tempo, to break something down to first principle thinking. And if you do that, then I think that's going to be the opposite of these slow-moving, kind of soul-crushing bureaucracies.

19. 50:05 – 56:02

    Tips for preventing burnout

    1. BCBrian Chesky50:05

    2. LRLenny Rachitsky50:05

       I've definitely been through that where you set a crazy goal and then we ended up hitting it, and so I've seen that myself.

    3. BCBrian Chesky50:12

       (laughs)

    4. LRLenny Rachitsky50:12

       With some of the things you've talked about of, say, do it now, we're not gonna wait, uh, another week to circle back, and this stuff you talked about of taking on the CPO role, not having a CPO, and also all these launches, it sounds like a lot of work and a lot of hours. What have you learned about avoiding burnout and creating balance, and also just helping people on your team avoid burnout and creating balance?

    5. BCBrian Chesky50:33

       So first of all, um, I want to give you a, a, a, a very surprising learning.

    6. LRLenny Rachitsky50:39

       Mm-hmm.

    7. BCBrian Chesky50:40

       I weirdly now, the more I get involved... This is so weird. The more in the details I am, the more time I have on my hands.

    8. LRLenny Rachitsky50:47

       Hmm.

    9. BCBrian Chesky50:48

       That's a paradox. And I wanna explain that paradox, because it doesn't make any sense. When I explained this process to people, that I would be in the details, we'd have one shared consciousness, I would review everything, we would do endless edits of even the press release, it would seem like I would be working 80, 100 hours a week and that people would be disempowered and that no one would want to do anything. And I got just the opposite. Here's what I found. If you decide to be in the details and get very, very hands-on like I did, it might be a lot more work for about one to two years. And so for one to two years, it was way more work than the old way. But once we turned the corner, suddenly everyone started rowing the same direction. Suddenly I didn't have to be in meetings anymore, and people would do what I wanted them to do if I wasn't there. And by the way, that's what the culture is. They say the culture is what happens when you're not in the room, and the brand is what people say when you're not in the room. And so that became our culture, that suddenly there was fewer conflicts in the company. There was less turnover. People were rowing in the same direction. That I wasn't reacting. Before, I would get 10 surprises and nine were bad. Now, I get 10 surprises and nine are good. And you don't really have to do anything about good surprises, only bad surprises. That I used to have to intervene in projects that I wasn't involved in 'cause they were going off into the wrong direction, and by the time I got involved, I was associated with dysfunction. But I only got involved because it was dysfunctional. It wasn't actually going well. And then it was three times as work to fix something 'cause we weren't involved in the very early e- stages. So I, I was much more involved. I had a lot less time on my hands initially. And now I actually weirdly have a lot more time on my hands. But to answer your question on burnout, I think is another very good question. I do not think I am the poster child, at least historically, of work/life balance. I'm 42 years old. I live with a golden retriever. I don't yet have a family. And if you asked me when I was in college how I thought my life would be right now, I probably would have thought the inverse, that I'd have a family and I'd one day run a company. And I did things in a slightly different order. But one of the things I've learned is that there's this temptation to work more and more and more hours, and sometimes you need to... It's like an artist, you have to step away from the painting. And you actually start getting more derivative slower and slower. And so I basically have tried to make it a practice to step away from the work. And so here are some of the things I do. Every other weekend, I, like, don't really work at all, and then, you know, every other weekend, I work pretty intensely. If I had a family, it would probably be more like a day, a day of the weekend I'd work in- more intensely, so, you know, I would, you wouldn't be a parent over the weekend, but I'm not, so it's a little different. I usually make sure I exercise and I never miss a workout, so I usually, like, wake up. I'll do, like, 20 minutes of morning cardio on a Peloton. I'll go to the gym three or four times a week and do weights. I'll, I'll basically do cardio just about every day. I make sure that I eat really healthy. I have, like, a kind of classic, like, bodybuilding diet of five to six meals a day. Um, so I think... I try to make sure I do that. I try to make sure I get a fairly good amount of sleep. And then I... The other two things I try to do is, like, have really healthy relationships. I think one of the most important things that will govern, like, how happy you are in your life is your relationships. I think the two govern... I think the three things are your health, your relationships, and your work. Those are probably the three most important things. So as long as you're healthy and you have meaningful work, the last is relationships. And there was this Harvard study, it's the longest study on human happiness. I think it's 85 years old. And the question was, what's the secret of happiness? And of course, they weren't expecting to have a single answer, but they got one. And the answer was, the secret to happiness, if there is one, is healthy relationships. And I had found, Lenny, that over the time of being an entrepreneur, I had gotten totally isolated, that it was almost as if I didn't have friends. I had friends, but I didn't keep in touch with them. And every time I reached out to a friend, I had to get them up to speed on my life. And even if to get people up to speed, you're not really keeping as much in touch with them. And so, I started making it a practice a couple years ago to make sure that I have a group of friends that I'm constantly in touch with, including old friends. So I have a group of high school friends. We have a group chat and we take one to two trips together a year.I have a group of college friends. We have a group chat. We take probably a couple of trips together a year. By the way, doing Airbnbs are great. We all get in a house together, and it's like you... your opportunity to have a shared experience. And if you don't travel with your old friends, you have only old stories to talk about, and then you kind of say the same old stories over and over. So you want to be able to have new shared experiences. When I stay here in New York City, I'm in New York right now, that's why you don't see my typical background, I stay in a... my sister's apartment. So she's got a two bedroom, and I stay in her house because I like to see her. And I just make sure I spend a lot of time with friends. And of course, we travel. I mean, traveling is what I kind of do with a lot of my friends, and then I like to draw and read. So I try to make sure it's health, work, and relationships, and I try to make sure I have a balance of each. And you might call family relationships. You know, I'm just... I'm single, but, you know, that would be, uh, another version

20. 56:02 – 58:19

    Tips for personal and professional growth

    1. BCBrian Chesky56:02

       of it.

    2. LRLenny Rachitsky56:02

       I heard you say along the same lines on a different podcast about how when you were really busy, you didn't have time to reach out to anyone, and they never thought they could reach out to you because they thought you were so busy.

    3. BCBrian Chesky56:12

       In the old world, I was reacting, so everyone thought I was busy. So the people I really cared about, a lot of them said, "Well, he's busy, so he'll reach out to me when he's not busy." But here's the problem. I was so busy that all I was doing all day was responding to people. And so if people I cared about didn't reach out to me, I was just... I was dealing with incoming. I could barely deal with the incoming. Now, that was a mistake. But I was b- reacting. And so... By the way, here's another lesson for founders. A lot of founders spend their time based on reacting. So people will email them, and they'll wake up and they'll respond to emails, and suddenly their email sets the agenda. People ask for meetings, and suddenly the meetings they take are based on the people who email them. Versus like, "Here's my strategy, and then over the next year, what are the relationships I need to have and the meetings I need to take to be able to execute this strategy? If my life were to end in a year or in 10 years or some time horizon that's shorter than I expected, who are the people I would have wanted to make sure I spent time with?" And if you imagine that your life is finite, because it is, and you imagine you're not going to be here as long as you thought you would be, because it's possible, it would completely change how you prioritize your time. And I think suddenly you would start to say no to things, and you'd say yes to other things. I now try to say no to what I call fake work, which is things that feel like work but they don't actually move the ball down the field. And I really try to say yes to work that's very meaningful and people that are very meaningful to me. So yeah, it's a really, really good insight. And by the way, that metaphor, Lenny, it's true of companies too.

    4. LRLenny Rachitsky57:54

       Hmm.

    5. BCBrian Chesky57:55

       You can sometimes be res- like... You don't want to only spend your time reacting or, or spending your time with the employees reaching out to you. I mean, you do want to do some of it, but then you're rewarding, you know, only one type of behavior. And the introverts or the people that aren't reaching out to you aren't going to get any attention.

    6. LRLenny Rachitsky58:14

       Just one more question, and then I have a quick fun question at the end. I know you have to run.

21. 58:19 – 1:02:58

    Why Brian says he still has a lot to prove

    1. LRLenny Rachitsky58:19

       If I were to ask people who are the most inspiring leaders in tech and in business in general, I think you'd be right near the top of that list. You've been through a lot of ups and downs. You've learned a lot of lessons on the... along the way. What have you found has been most helpful to helping you continue to grow and keep up with the business, the way the business is growing, the scale, and just to take on this leadership role? Is it like coaching? Is it reading? Is it other mentors? Something along those lines.

    2. BCBrian Chesky58:46

       You ask really good questions. And by the way, thank you. I, um... So I'll, I'll share a few thoughts. I was, I was with Sam Altman probably a few weeks ago at dinner, and I told him, "You know, I still feel like I have a lot to prove. I haven't made it yet." And he was re- really surprised. He's like, "What are you talking about?" And I didn't even realize that he thought that was an absurd notion. But I said, "No, I haven't made it yet." It's not to say I'm not grateful or I feel like I need to get somewhere so that therefore I'll feel, like, worthy. But I have this still... this kind of beginner's mindset, that the bigger I get, the more a beginner I tend to feel. It's like a weird feeling. I think, like, when you f- when I first took off, I think I thought I, like... maybe, like, I knew everything or I knew more than I certainly did. But then you get past some peak where you go into this trough where you realize, oh my God, the moment you get to some frontier of knowledge, you start to become a beginner again, and everything is new. And so I think the first thing I try to do is to be a beginner. You know, Pablo Picasso had a saying. He said, "It took me four years to learn to paint like Raphael, but a lifetime to learn to paint like a child." And so I've tried to always see the eye- the world through the eyes of a child. And I think one of the key characteristics of a child is curiosity, to see everything with fresh eyes, to not have too many judgments. Like, when I was trying to figure out how to run the company, I studied the history of division organizations. And I studied Steve Jobs, but also studied, like, what Bill Gates did, and I studied, like, Alfred Sloan at General Motors that MIT s- uh, MIT Sloan is named after. And actually, the founding of divisional companies, which I believe was DuPont. They were making powder for gunpowder. The war ends. What do they do with powder? Turns out powder can be used for paint. But the way you sell gunpowder and paint are different sales channels. So they created what we now know as the divisional structure. So I try to, like, understand the sources of things. I try to learn. I try to be shameless about reaching out to help. I think that a lot of people are afraid to reach out to help because they think other people are busy. The biggest honor most people get in their lives, or one of the biggest honor, is when other people ask them for help. Because we all just want to feel useful. So don't feel ashamed to reach out to something for help. It actually, like...... it gives a lot of them great honor. And I think you don't need to reach out to people 10 years ahead of you. They can just be people a year ahead of you. In fact, an entrepreneur getting started, I might be less useful than somebody two years ahead of them that knows, like, the latest distribution channels that I, like, kind of have forgotten. So I think that that is the key. It's learning. It's growing. It's curiosity. It's constantly having that hunger and that fire to always want to be better, to remem- to feel like I haven't made it yet. Because the reason I say I haven't made it yet is because if I've made it then I'm done.

    3. LRLenny Rachitsky1:01:53

       Mm-hmm.

    4. BCBrian Chesky1:01:53

       And I want to feel like an artist. You know, Bob Dylan used to say, "An artist has to be in a constant place of becoming." And so long as they don't become something, then they're gonna be okay. And so you ha- I- you have to always be evolving, learning, growing. And the canvas keeps getting bigger. The mountain top keeps getting higher. And I feel like I'm just getting started and I hope that, you know, the pa- I don't, I don't know how long you intend to do the podcast but I intend to do this for a long time.

    5. LRLenny Rachitsky1:02:24

       Mm-hmm.

    6. BCBrian Chesky1:02:24

       And if you do or, or whatever, we'll definitely wanna have talks. And I hope years from now, Lenny, I hope 70% of what I said I still believe. But if 100% of what I say I still believe then I probably haven't learned very much. And so even if, if 90% I say I, I don't believe any more then I'm, like, you know, kind of delusional and wrong. But if, but it, but I sincerely hope that I retract or change or modify a few things I said today in a few years because that will mean that I've gained more wisdom. And so how do I do that? By being curious.

22. 1:02:58 – 1:05:03

    Paying it forward

    1. BCBrian Chesky1:02:58

    2. LRLenny Rachitsky1:02:58

       That is beautiful. It reminds me, you mentioned Sam Altman. Um, read... and there's a tweet that he put out a couple weeks ago that I'll read real quick. "Many people have reached out to offer help and advice over the past year. No one has gotten close to Brian Chesky in terms of delivering. He will take a midnight call at any time, put in hours of work on any topic, answer difficult questions correctly with clarity, make any intro, et cetera." How's that feel to have seen that?

    3. BCBrian Chesky1:03:23

       It was... I, I had no idea he was gonna do that. And I just want to say, like, I think Sam is obviously, like, a once in a generation founder. I think what he's done with OpenAI is extraordinary. And when he launched ChatGPT, I had known him for a real long period of time and I kind of knew a sense of the journey he was about to go on. And I think that he was very deep into the technical part and the research orient- part of OpenAI. But it turned out there was a product, a design, a marketing, a leadership, a sales. There were all these other functional responsibilities. And so being able to just play a small part in, you know, giving some advice when necessary and he would take what he wanted and discar- discard others. But I think, Lenny, maybe this goes to another thing, which is all I tried to do with Sam is what other people did for me. When I started, before Y Combinator, there was a person named Michael Seibel. He's in Y Combinator. And he used to meet with me and give me advice. And he wasn't an official advisor, he wasn't an investor. I didn't hire him or anything like that. He was on my board. And I asked him, I said, "How do I repay you?" And he said, "Well, I want you to pass this on to other founders." And I would meet with a lot of people in the Valley and there was just this, like, incredible culture of generosity that, that we all were gonna win, you know, if the (laughs) ecosystem was healthy. And the ecosystem would be healthy if we all helped one another and you kind of pay it forward. And so, you know, I, um, you know, I think that it's just one continuation of the Valley, of people helping one another, learning from one another. And I also feel like I learn by teaching as well.

23. 1:05:03 – 1:09:26

    A fun fact about Brian

    1. BCBrian Chesky1:05:03

    2. LRLenny Rachitsky1:05:03

       Final question. When someone joins Airbnb, there is a very longstanding tradition of sharing a fun fact about yourself. It might be the longest standing tradition. Uh, it's always tough on the spot, but I'm curious, Brian, if there's a fun fact that you wanna share about yourself that maybe people don't already know.

    3. BCBrian Chesky1:05:18

       Oh. Yeah. So a fun fact about me is that I actually spent most of my life as an artist. You know, when I was five years old, I remember my parents, like, taking me to the Norman Rockwell Museum and I would sit in front of, you know, his beautiful illustrations. They're really paintings, I should say. I shouldn't even call them illustrations. And I would try to reproduce them. And I got obsessive with art. I remember when I was maybe in elementary school, I asked Santa for poorly designed Christmas toys so I could redesign them.

    4. LRLenny Rachitsky1:05:49

       (laughs) .

    5. BCBrian Chesky1:05:50

       When I got slightly older, one of my friends, I went to his house, but I'm gonna say I was like eight or nine years old. And his dad was basically, like, redoing his deck but his dad decided to design it himself, I think maybe he was an architect. So we had this giant dining room table and he had, like, this vellum paper and he had a T square and a drawing triangle and a protractor and I... The, the just, they were cool, they were really cool looking tools and they were basically floor plans and architectural drawings. So I got into architectural and landscape design when I was, like, eight or nine and that led to my interest in architecture. I went to RPI, I was a freshman year of co- uh, of high school to do, like, a pre-college program. Then I got into, like, more and more drawing and figure drawing. Then I got into film and animation. Then I got involved in en- environmental design. I realized that if you buy stock in a company, you could get these cool glossy annual reports. This is kind of when the internet was kind of, like, nascent and people still mailed annual reports. And so I got my dad to buy a few shares of this, of this Disney stock and I got these renderings and the annual report of theme parks and I started, like, drawing, like, and designing, like, theme parks in communities. And I was at this private school for, actually for hockey because I had this parallel life where I was playing ice hockey and I, I thought I was gonna blue- play college hockey. My dad was really into it. I was really into it.... and I had an art teacher in high school, at this military school. That's another fun fact. I basically went to a military high school.

    6. LRLenny Rachitsky1:07:21

       Wow. I did not know that.

    7. BCBrian Chesky1:07:22

       And at this military sports academy kind of oriented high school, I had the same art teacher from eighth grade to eleventh grade. And that's not a good thing, by the way. I'm not saying that's a good thing. Because I, I was not diversifying my skills. And so I leave this high school, because I wanted to pursue different interests than hockey, and I transfer to my public high school late my junior year. And imagine, like, transferring to a new public high school late junior year. And I meet my art teacher, who changes my life. Her name is Ms. Williams. And she sees my artwork, and by the way, my mom was nervous about me becoming an artist. She said, told me, I chose a job for the love and I got paid no, I got paid no money, so you should choose a job that pays you a lot of money. And I said to my mom, One day I'm going to be an artist. She said, Oh my God. You chose the only job where you're gonna be paid less than a social worker. So I think my parents, you know, they were supportive of me going into art, but they were very nervous. And then Ms. Williams told my mom, she said, Don't worry. He's going to be a famous artist one day. I wasn't planning to become a famous artist. But what that did is I think it gave everyone the confidence for me to pursue art. I ended up being one of the f- a winner, there were multiple winners, of a national art competition, and I had my artwork displayed in the rotunda gallery. That then led to me getting a scholarship to Rhode Island School of Design, where I ended up going to RISD. It's like, you know, it's kind of like, it's kind of like MIT for design or whatever. It's like a, it's a prestigious art and design school. But I got to RISD, and I realized I was born 100 years too late for what I wanted to do, which is, you know, draw and paint, and I felt like at that point photography and now AI generated art, but certainly even back then, photography was replacing a lot of the skills that like, that I need, that I had. And that's when I was in my freshman year of college and I learned about a funk, a field called industrial design. They indu- they said industrial design is the design of everything from a toothbrush to a spaceship and everything in between.

24. 1:09:26 – 1:13:27

    Airbnb’s origin story

    1. BCBrian Chesky1:09:26

       And really, Lenny, maybe just to round out this story, because that was a fun fact, but I'm kind of just, and this is the pre-founding story that I never tell. I don't think I could have ever done what I did if I wasn't an industrial designer. I think an industrial designer is different than a graphic designer, because an industrial designer, you have to actually under- you know, you have to work with engineering in your, in your training. You have to, like I worked with mechanical engineers, electrical engineers. You have to understand manufacturing. Industrial design is very accountable to sales. If you design a building, an architect, and you design an office building and the office building doesn't get leased, the architect's usually not on the hook for it. But if you're an industrial designer and your design, the product doesn't sell, you're like kind of on the hook for it, or at least people assume you didn't design a good product. So you have to understand marketing and strategy. And so that became this gateway. But I didn't really want to make items and objects my whole life. But at RISD, the biggest value I got in addition to learning industrial design was I met my co-founder, Joe Gebbia. And the day of graduation, Joe looks to me. He says, "Brian, I think we're going to start a company together one day." And I had no idea what he was referring to. So I moved to Los Angeles where I worked as an industrial designer for two years when one day, I got a package in the mail that changed my life. I opened this package and it's a seat cushion with a handle on it, and it's a letter from Joe, my, my friend from RISD. He said, "I started a company, and everyone in San Francisco, I live in San Francisco, and all these people are starting companies. You should come here." And this is in 2007. YouTube had just come out. I had like seen all these Steve Jobs keynotes finally on YouTube. I didn't know who he was. I never heard his voice before, before YouTube. And, you know, Apple had this renaissance and Google was on fire and Facebook was taking off, and it felt like the gears of the world that were turning were in San Francisco. And so one day, I go into work and I quit my job. My boss is dumbfounded. And I pack everything in an old, uh, old, uh, back seat of an old Honda Civic. I get to San Francisco and Joe tells me the rent is $1,150. I don't have enough money to pay our rent. This design conference is coming to San Francisco. All the hotels are sold out. We said what if we turned our house into a bed and breakfast for a design conference? I didn't have any beds, but Joe had three beds. We called it Air Bed and Breakfast. So my fun fact was I was an artist and designer before Airbnb. Really, an artist. At least how I thought about it. And I think that's maybe one of the things that makes Airbnb different, because there's not a lot of designers or artists running Fortune 500 or S&P 500 companies. And I think that intuition, imagination, design, curiosity, I think we need more of that. By the way, I think the people listening, I think everyone on this, listening to you has these qualities. But I think that a lot of companies, it's like we're a body and the companies are cut off at the head. They're disembodied from the heart and they're often really biased towards one side of their head. And I think that some of the greatest scientists played musical instruments, like Einstein. I mean, I think that by being a whole well-rounded way of thinking about the world is good. So anyways. That's my final thought.

    2. LRLenny Rachitsky1:12:37

       I love that fun fact, because it almost explains everything you've been talking about, which is rethinking the way companies can run, doing things super differently. So I really appreciate your sharing that. I also love that it transitioned into the creation story of Airbnb, which happens a lot at Airbnb. People hear that story over and over 'cause it's, uh, so interesting and so important. Brian, I know you have to run. Thank you so much for being here and being generous with your time.

    3. BCBrian Chesky1:12:58

       Thank you, Lenny. And congratulations on everything you're doing.

    4. LRLenny Rachitsky1:13:01

       Thanks, Brian. Bye, everyone. (upbeat music) Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Episode duration: 1:13:27