In this podcast episode, Brian Chesky, CEO of Airbnb, discusses his philosophy on leadership and product management. He argues that many founders apologize for their vision, leading to confusion; instead, clarity and alignment make everyone happier. He distinguishes micromanagement from being "in the details," emphasizing that leaders must understand details to evaluate performance. Chesky explains Airbnb’s restructuring of product management: merging inbound product development with outbound marketing, offloading program management to specialists, and creating a smaller, more senior product marketing team. He notes that designers often feel frustrated, treated as a service rather than core to development. He describes how large companies can devolve into silos, dependencies, politics, and bureaucracy, slowing innovation. On marketing, he contrasts performance marketing (a laser for specific targets) with brand marketing (a chandelier for broad illumination), advocating for product marketing that educates users. Airbnb now uses a rolling two-year roadmap updated every six months, with company-wide releases in May and November. Chesky believes the CEO should be the chief product officer, staying deeply involved in products. He reflects on a cycle where founders delegate too much, leading to dysfunction, and then must retake control to drive alignment and speed.
way too many founders apologize for how they want to run the company. They find some midpoint between how they want to run a company and how the people they lead want to run the company. That's a good way to make everyone miserable because everyone really wants this clarity. Everyone really wants to be able to row in the same direction really quickly. So I basically got involved in every single detail and I basically told leaders that leaders are in the details. 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 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 good job. People think that great leaders job is to hire people and just empower them to do a good job. How do you know they're doing good job if you're not in the details. So I made sure I was in the details and we really drove the product. Today my guest is Brian Cheskey. Brian is the CEO and co-founder of Airbnb which he started in his apartment with his co-founders Joan 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 Cheskey 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 change 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 weight 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 Giro Product Discovery. The new prioritization and road mapping tool built for product teams by Atlassian. With Giro 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 Giro, where your engineering team is 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 Giro Product Discovery for free. No catch. And it's only $10 a month for you. Take advice your spreadsheets and the never ending alignment efforts. The old way of doing product management is over. Rediscover what's possible. With Giro Product Discovery, try for free at Atlassian.com/lennie. That's Atlassian.com/lennie. Brian, thank you so much for being here. Welcome to the podcast. Well, thank you for having me. Did you ever think when I left Airbnb one that I would have a podcast and two that you would be on my podcast? I had no idea you would become a podcast host and that you would have such a successful podcast. But yeah, congrats on everything. It was awesome. I appreciate it. Congrats to you too, Brian. Thanks, Steve. You're going great. I'm excited that you're here. I want to start with the elephant in the room for a lot of listeners of this podcast. What is going on with product management at Airbnb? You made some comments at FigmaConfig. A lot of people got this impression that you eliminated product management at Airbnb. I've heard from a lot of product execs having boardroom conversations as a result of that. They were trying to decide, should we remove product management from the company? Should we significantly cut product management? 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? I spoke at Figma four or five months ago. I spoke to a room of designers. I then got off stage. I saw people, somebody tweet that said something to the nature of that I said I got rid of the product management function, all the designers that started cheering. So I want to talk about two things. What I actually meant, because I didn't actually get rid of the people. And also, why did the people in the room cheer? Because that's also like a thing we should ask ourselves. I hope everyone listening to this podcast should understand where did that place come from, that 5,000 designers in the room cheered because I thought I eliminated the existence of a function. Because if I said I eliminated the engineering function, no one would have cheered. It was specifically that function. So I want to 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 yours 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 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 that product management title are actually program managers. So we actually started off-boarding some 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 the most senior people are called product marketers that 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. 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 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, it 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 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 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. The last thing I want to say is why did 5,000 designers shear when the people thought I removed the product management function? Because I don't know if I can speak on behalf of all the designers, but having talked to the last owners. I think designers in the valley are very, very frustrated with the product development process. Not to say the product managers, but they are extremely frustrated. I think a lot of designers feel like they are compromising. Many designers I know, heads of design. All known heads of design, I told them they are not designers, they are design administrators. They are running a design service organization. Because Silicon Valley often treats design as a service organization. Design is catching things before it gets a door. It's not actually a part of the development process. I think this is not just bad for design. It's bad for product managers and engineers because we all want to build the best products. One day you wake up and a variety of phenomena might have happened. 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 solid technical stacks. That's the first problem. They may actually be a team-linked technical debt. The next problem you'll see is that there is a lot of dependencies. Five teams are going to different directions.
but they all need a payment platform. And so that 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 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 like that build the best relationships are the ones that get the most resources. And that creates what we call polytests. It's now polytics that brood 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. And when there's lack of accountability, then there's a sense that what I do doesn't matter. And that creates complacency. And then suddenly a fast-drowing company becomes a big, slow-moving bureaucracy. This is a general arc that winds up happening. And then you end up having a situation where companies done 10 marketing efforts, but no customers 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 marketing and engineering 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 coasters engineering marketing. And marketing is a lot of companies are like the waiters, engineers are like the chefs, and the chefs, the alt the waiters, they go in the kitchen. In fact, the waiters, the ones talking to the customers all day, and they also know how to sell things. So you really want them being joined 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 also the other thing we were doing is as you know Lenny, we're spending a lot of money in performance marketing. I don't think performance marketing is a bad thing. I think of marketing as a laser. Actually, my co-founder, who obviously know well Joe, used to have this metaphor of lasers, flash bulbs, and chandeliers. If you want to lay up a room, performance marketing is a laser. They can light up a corner of a room. You don't want to use the much lasers to light up an entire room. She uses a chandelier. And that's what brand marketing is. But if you do need a laser end, 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 bookie.com, if you have a really higher ROI, now you can have a performance marketing arbitrage business. But assuming you don't want an 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 are shipping, there's no purpose to ship new things because you ship new things and people don't know if I never 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. 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, is you remember Lenny, when you're 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, that's strategy, product strategy roadmap, that gets updated every six months with releases. We release products every May and every November or October. Obviously we did one today we can talk about. The entire company works together. They row in the same direction. And the product management also does a product marketing. So they're figuring out how people are going to learn about it. They're doing the demos. They're understanding the story, the videos. They're figuring out all the customer touch points, making sure everyone understands it. Our product marketing works with communications. We 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. We wanted a company where 1,000 people could work, but it'll look like 10 people did it. And so sorry, that was a bit of a brain dumb, but that is a little bit of a universal theory for how we develop products now. I can go into a lot more detail, but I probably will stop there. - That was amazing. You touched on all of the things I want to talk about. So I'm gonna-- - Oh, gee. So we can go deeper and deeper. 'Cause the rabbit will go-- - Yeah, exactly. Exactly. So I'm gonna pull on a couple threads. The first is this idea of a single roadmap. You talked about it. 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 it's a 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 he talked about bureaucracy and politics. And then eventually, he realized, 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. - 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 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. 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 the CEO's not the chief product officer then I don't know if they're a product or tech-led company. Maybe that's okay if they're an ops company or if they're a marketing company or if they're not a tech company at all. But ultimately, I think the founder CEO should be that person. So when we were starting Airbnb, it was probably the three of us. As you know, 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 people listening, like the closest thing to the role of the product manager. But again, I did marketing, I did design, I did ops, I did like kind of a little bit of everything. So I was basically everything by engineering. And then as we grew, I started getting more and more hands off in the product. And I always remember Lenny, when you were in this, there was this paradox where the lesson evolved, I wasn't a project. I mean, there was, there would be clear. There were times I inserted myself in dysfunction occurred. That is absolutely true. And that was just a learning experience for me. But there's this other scenario where the lesson evolved was in the 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 because I was too involved, right? Because people assumed that our natural equilibrium is to move fast, shape from being slow, is because of an over-envolved in leadership. And therefore, I would get less involved. I would give teams more control. I would give them 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 end up in a situation where you're delegating down. So I think that things were getting worse in 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 testing. I think A/B testing is important in times. But like, let me, actually, 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 with you this year. 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 a really, really big problem. And every can never change it. And imagine 10 teams doing A/B testing. And like, imagine if you were designed software, the way designed to house, or designed house the way you've done software. And we A/B test a sofa. And we said like, well, how does a 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, people are unlike this room better. But actually, the sofa has a relationship to the end stands, which have relationships 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, everything else helps.
You have to think about the whole cohesive system. And I started realizing that I remember working with, I asked one person on your team, somebody you know well, and I asked him, I said, "Why is there, "I feel like I open our app and the product hasn't changed "in like four years." I remember saying this like 2018, 2019, and this person described that you know well, as just the way we were doing things, the initial way we were doing things to move fast had made us move slow. So we end up doing, is it was now late 2019. I don't know what to do. I'm like, the product is slow, the app seems not changed, cost arising, 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 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 Horokey Asai. Horokey now works at Airbnb. He's one of my executives and actually product design, product marketing design and marketing report into him. And he was a creative tractor for Apple. So he worked for Steve Jobs, was basically dotted line to Steve for many, many years, came from graph design, eventually ran all of marketing communications, and Apple marketing communications, they actually designed the app. They made the app. They designed all the marketing touchpoints for the store. So it wasn't just ads, it was like every brand touchpoint, 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 re-claimed to the person, named Johnny Ive. And Johnny Ive was the head of industrial design and sheep design officer 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 the ARV semi-div, like the services is trying to 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, we had 10 divisions. We had a flights division and, you know, we had a Holmes division, which is divided to Prohosts and Corehosts and Luxe. And we had business travel and we had like, you know, a magazine and we had experiences and we had.org and we had China. So we had like these 10 different divisions all going in different directions. And I created this culture where everyone would be a business manager and or a, 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 a very, very difficult 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, tried to adjudicate different issues between groups. So then the pandemic occurs. And I had this image on mine. It's like I have this dream that I could run a company much more like a startup. I remember going in a walk with Joe and Nate and Belinas. It was October, 2019. And I told them I had this dream that I left the company 10 years ago and they just asked me to come back. And I said, I was horrified at what I found. And they said, well, what'd you find? I said, I found a company that on the one hand had amazing culture and people with a great mission, with the brand people really loved. But we lost her design roots. 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 both growth was slowing. And that was exactly what was happening. And then the pandemic occurred. When we lost 80% of our business in eight weeks. And then suddenly, we're like, oh my god. I remember having a 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 you're flashed before your eyes. You have clarity. And that's what happened to our business. We had a near death business experience in our business flash before our eyes. And so suddenly, I basically got into action. And I said, I'm going to run it this other way. Where I'm going to get back into the vault in the 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? 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, like a Google sheet. It turns out people couldn't even write down everything they were doing. I remember one person told me, you think, 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, OK, we can do about 20% of these things. And so if everyone says, oh, I might-- it might be simple. I'm only doing three things. Yes, but you're one of like 1,000 people. So actually, we're doing 3,000 things. So to set a 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 team. We went to a functional model. We went back to a startup. So we said, we're not going to have divisional leaders. We're going to have design, engineering, product, and what's turned to product marketing, and marketing, communications, and sales, and operations, all the functions of a startup. I said, we're going to have fewer employees. We're going to have fewer and more senior people. There's a great saying that the best way to slow a project down is adding more people to it. So we felt like very few employees. We have fewer than 7,000 employees today. It's a relative comparison. I think Uber has 30,000. 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, or maybe not a lot, but that they exist, or there's designers, but there's design leaders who lead the people. A design leader's job should be managing the design first, the people second, as a Johnny did, or like they're interchangeable. It could never imagine Johnny of 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 the 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 a company are going to have one continuous conversation. Metrics are going to be subordinate to the calendar. So we're going to have a roadmap. It's going to be a two-year roadmap. Well, update the roadmap literally every month. People may wonder, well, what if the world changes? Yeah, it changes every day. So the roadmap's something where the next month hasn't changed, but two years out, it changes. It's a rolling roadmap. And by the way, if Ukraine gets invaded and you want to provide housing for refugees, you can still pivot people and adapt very quickly. We house 112,000 refugees. So you still keep a reserve of resources to be able to pivot and do things, because there's always unexpected events. I created this new function called product marketing. We basically describe what that is. I'd meet the group much smaller. I took a lot of product managers. I reassigned my program managers. I had many of them trained in actual program management, because the role's got much bigger. Program management, Airbnb is a high status job. A lot of companies, it's like a coordination job. At Airbnb, we said, because we're going to do launches, it's high status. We said, we're going to do two launches a year, and you can't ship something unless it's on the roadmap. So every single thing in the company, what the steps of some infrastructure projects have to be on the roadmap. And then I'm going to review all the work. And so we create the CEO review schedule. Where I said, I'm getting back in the project, and I'm going to design, I'm going to review all the product in all the marketing. So every project I would review 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 their regnial or red, being their on track, or not on track to ship. Whether we thought there 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 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 individual engineer. Because imagine it's like we're a car company. And I see the car prototype every week. And I notice there's something about the tires off. Now I can identify the individual person who was blocked. So every week, I would see-- I would try to see the equivalent, have 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--
We read all these reviews. I did need to mandate what 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 It's so these were these were like some of the changes that we made 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 why we can be or shiter in those anymore We actually build our own in-house agency so to speak which is a creative group the creative group Does a lot of that that 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 set 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 the design Then that doesn't make sense. So we we really make made a lot of those changes Just if 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 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 If you're a founder what I would tell you is the problem with finding a negotiation between how you want to run a company the people you want Is that's a good way to make everyone miserable because what they ever when really wants is clarity With everyone really wants 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 the company were 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 is 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 Micromanage it which is like telling people exactly what to do in being in the details Being 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 good job people think that great leaders job is to like higher people and just empower them to do a good job Well, how do you know they're doing good job if you're not the details? And so I made sure I was in the details and we really drove the product This episode is brought to you by Epo Epo is a next generation AB testing and feature management platform Guilt by alums of air being being snowflake for modern growth teams Companies like twitch, mero, clickup and draft kings rely on Epo to power their experiments Experimentation is increasingly essential for driving growth and for understanding the performance of new features An Epo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other Commercial tool does when I was at a beam beam one of things that I left most was our experimentation platform Break it set up experiments easily troubleshoot issues and analyze performance all on my own Epo does all that and more with advanced statistical methods That can help you shave weeks off experiment time and accessible UI for diving deeper into performance And out of the box reporting that helps you avoid annoying prolonged analytic cycles Epo also makes it easy for you to share experiment insight through their team sparking new ideas for the AB testing flywheel Epo powers experimentation across every use case including product growth machine learning monetization and email marketing Check out Epo at getepo.com/lennie and 10x your experiment velocity. That's get eppo.com/lennie You guys found such a unique way of working. I've never heard of a company working in these ways and 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 pay 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 a little like a consumer specific Opportunity what advice would you give to founders that are thinking about man we should try something like this 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 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 passive 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 ball down the field versus in 20% passes. So I think that this methodology will work for everyone. I mean, sure 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 in themselves of this cheap 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 no way saying it Lane Every product manager should be interconnected and know what everyone else is doing They shouldn't be independently silo unless they're really are running like separate companies who 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 the void of their work Yeah, imagine like a fire chief. 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 gross 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 your day But then package it and tell a story if you aren't gonna hold the product back I think that team should use data But they should also use research and intuition There's a designer called Charles Ames I said you can't delegate understanding If you're gonna do a be experiments or measure data you have to understand what it means I think that you have to have an intuition It tuition comes not from arbitraryness 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 designed under product unless you have an extreme of good reason the product person kind of is a designer I would try to think about product management Expanding the responsibility In 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 working technical functions. That's fine But they don't work in non-technical functions. I think that's a problem I should make sure that marketing and engineering are interconnected I would make sure that you have a few layers between the CEO and other people If you're a CEO every direct your direct should be a implicit data line to you So I treat every direct to my direct as if they're a direct report a data line I don't try to conflict with the directs on 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 ten year story You may not know where you are in ten 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 I'm not sure what it would be, but 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? Speaking of rowing in the same direction You're 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 Let me just back up, so Lenny so yeah, you know this problem really like well One of the best things of Airbnb is that we're this marketplace where guest and host come together And we have all the unique inventory and people you know list on IRB and B And every home is one of a kind and we use seven million homes and there's all the surprise and all is 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 guest or people who don't use Airbnb The number one read that 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 you're gonna get And so what we found is that reliability is every music
at least a husband that, you know, with hotels, you're not gonna get an Airbnb, you don't always not gonna get. And so we asked ourselves, what if we could combine the uniqueness of Airbnb with the reliability that you've come to spec hotel? And that's what we've done with guest favorites. Guest favorites are, you know, homes that guest in our tuning love the most. We took 370 million reviews on Airbnb plus millions of customer service tickets, plus all the host cancellation data. And we use all the signal to create the top 2 million homes that this collection of 2 million homes that we call guest favorites, 'cause the gallons of the guests rate the highest. We think combined the uniqueness of Airbnb with the reliability come to spec hotel. And I can't imagine there's a lot of use case where you wouldn't want to book a guest favorite. We think that's also part of this broader system of readings 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 living together certainly. And we felt like the rating review system could use a little bit of an upgrade. So we obviously made some upgrades to the ratings 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 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're doing research is because 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. Oh, here's the other thing, Lenny. When you were an Airbnb, we had guest team and a host team. We don't have a guest team and a host team. We have a design team. We have a marketing team. We have an engineering team. The reason we don't break the app into guest and host anymore is because reviews affect guest and host. It turns out that the almost everything involves connecting the guest and host. And you have separate teams that tend to have separate roadmaps that go in separate directions and become incompatible. So we have product marketers that are responsible or guest and host things, but the designers are into 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 want to make sure that we have designers and engineers covering a much larger surface. And so that's what we 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 like to make the announcement that I think flat design is over or ending. I think if you remember the 2000s was dominated by skew morphism, the 2010s have been dominated with a launch of iOS 7 by flat design. I think we're going to move back into a world with color, texture, dimensionality, more haptic feedback. But I don't think it's going to be skew morphism, where it pretends to be like a wood drain to reference like a dashboard or leather. But I think it's going to 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 in AI are gravitating to image generating art that has got more dimension to it. And so I think that we've really started to push this more three-dimensional, colorful aesthetic that I think is going to be where a lot of interface design is going. And we built this AI-powered photo tour, where we created our own AI computer vision 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 have been possible in the old way of working. We could have theoretically launched a lot of these features, but really getting them to work together has been key. And guess favorites has required the guest. People-- you have to work with guests. You have to work a host. You have to essentially figure out how to communicate to the market. So it's a much more integrated approach. 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. And 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. That's like, I think how many hosts are there? Seven million? Something like that. There's seven million listings. Yeah, there's over seven million listings. Yeah. And so that's the home base. That's the small business platform for millions of people. And so 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. Yeah, 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 a great host. And to have great host, they 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 them to buy the great experience for guests. And so that was one of the theories behind the listing tab is we're going to build great tools for hosts. They're going to love it. I mean, also felt like if we put Karen's design of our app, that hosts are going to see that and that they're going to actually, but care into hosting even more than they already do. And they do put a lot of Karen now. Speaking of great products, 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. 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? As you know, there was a saying inside of Airbnb, it was at a zero at a zero at the end, which is to make to imagine something order-managed bigger. The exercise isn't necessarily to say if people say they want to hit a goal, I say, OK, 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 reconstruct them? So the first thing is, I think, by adding a zero, at least conceptually for teams to help some 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 done for 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, OK, let's circle back on this next week. No, we'll have it done by next week. Let's stay in this meeting until it's done. What are you doing? Have a bias for action? Who is responsible? OK, what are you doing? OK, let's check in an hour. I'll call you in the morning. OK, how are we doing 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 basketball coach named John Wooden. He was one of the winningest basketball coaches, I think, in college basketball history, perhaps the greatest. And someone asked him once, I'm going to paraphrase what he said. Like, what is your secret to success? And he said that, I just asked 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 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 themselves. And 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, because they can feel that what they're doing is not good enough if they have a fixed mindset. Or you create a growth mindset organization where the more I'm involved, the more I say you can do better. It's because 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 Indie Grove used to say that there's competency and motivation. And motivation is if they're like, I mean, you're not literally dependent on it, but like if it was a crisis, or if it was like a defining moment of their lives. I think the job of a leader is not to make it life and death. That's too far. But to be all the motivated 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 he's.
If you do that, then I think that's going to be the opposite of these slow movings, kind of soul crushing bureaucracies. I've definitely been through that where you said a crazy goal and then we ended up hitting it. And so I've seen that myself. With some of the things you've talked about, say, do it now. We're not going to wait another week to circle back and this stuff you talked about of taking on the CPR 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? So, first of all, I want to give you a very surprising learning. I weirdly now, the more I get involved, this is so weird. The more the details I am, the more time I have on my hands. That's a paradox. I don't want to explain that paradox. It doesn't make any sense. When I explain 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 at 8,100 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 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. There were more rowing in the same direction that I wasn't reacting before I would get 10 surprises and 9 were bad. Now I get 10 surprises and 9 are good. And you don't really have to do anything about good surprises, only bad surprises. That I used to have to intervene and progress. I wasn't involved in because there were going off in 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 his work to fix something because it weren't involved in the very early eight stages. So 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 the answer question I'm burned out, I think is another very good question. I do not think I'm 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 ask me when I was in college, how I thought my life would be right now, I'd probably worth the inverse that I 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 in more hours. And sometimes you need to say that's an artist. You have to step away from the painting. And you actually start getting more derivatives, slower and slower. And so I basically have tried to break into practice to step away from the work. And so here's some of the things I do. Every other weekend I don't really work at all. And then every other weekend I work pretty intensely. If I had a family it would probably be more like a day of the weekend I'd work into more intensely. So you wouldn't be a parent every 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 wake up. I'll do like 20 minutes of morning cardio in a palletine. I'll go to the gym three or four times a week and do weights. I'll paint speed cardio just about every day. I make sure that I eat really healthy. I have like a kind of classic bodybuilding diet of five to six meals a day. 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 the other two things I try to do is like have really healthy relationships. I think one of the most important things that will cover and like how happy you're in your life is your relationships. I think the two govern. I think the three things are healthy. Your relationships and your work goes 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 of happiness if there is one is healthy relationships. And I had found Lenny that over the time of being an entrepreneur I got 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 to get people up to speed you're not really keeping as much in touch with them. And so I started making a practice a couple years ago to make sure that I have a group of friends that I'm close 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 groups together a year. I have a group of college friends. We have a group chat. We take probably a couple trips together a year. By the way, doing Airbnb's are great. We all get in the house together. And it's like you're an opportunity to have a shared experience. And if you don't travel 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 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. I'm just, I'm single, but you know, that would be another version of it. I heard you say along the same lines on a different podcast about how when you're 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. 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 who reached out to me when he's not busy. But here's a 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 the incoming. Now that was a mistake, but I was reacting. And so by the way, here's another lesson for founders. A lot of founders spend their time based on the reacting. So people will email them and they'll wake up in the reply 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 need to take to be able to actually do strategy. My life were to end in a year or in 10 years or some time rise and 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 as long as you thought you would be because it's possible that we completely change how you prioritize your time. And then 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. You can sometimes be like, you don't want to only spend your time reacting 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 only one type of behavior in the introverts or the people that aren't reaching out to you aren't going to get any attention. Just one more question and then I have a quick fun question at the end. I know you have to run. 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 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 has grown, the scale and just to take on this leadership role. Is it like coaching? Is it reading? Is it at their mentors? Something along those lines. You asked really good questions. And by the thank you, I'll share a few thoughts. I was with Sam Altman, probably a few weeks ago at dinner and I told him, I still feel like I have a lot to prove. I haven't made it yet. And he was 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 where 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 when I first took off, I think I thought I would maybe like I knew everything or I knew more than I certainly did. But then you get past some peak. When you go into this trial for 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
paying like a child. And so I've tried to always see the the world through the eyes of a child. 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 where 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 Journal Motors that MIT's MIT Sloan is named after and actually the founding of division companies, which I believe was Dupont. They were making powder for gunpowder. The war ends. What do you do? The 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 shamed to reach out to something for help. It actually like 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 it better. To remember 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. And I want to feel like an artist, 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 going to be okay. And so you have to always be evolving, learning, growing. And the canvas keeps getting bigger. The mount top keeps getting higher. And I feel like I'm just getting started. And I hope that the panel, I don't know how long you intend to do the podcast, but I tend to just for a long time. And if you do or wherever we'll definitely want to 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 that I probably haven't learned very much. And so if 90% say, I don't believe anymore than I'm like, you know, kind of delusional and wrong. But if, 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? That is beautiful. It reminds me. You mentioned Sam Altman. There's a tweet that he put out a couple weeks ago that'll breed real quick. Many people have reached out to offer help in advice over the past year. No one has gotten close to Brian Jeske in terms of delivering. You'll take a midnight call at any time, put in hours of work on any topic, answer difficult questions correctly with clarity, make it intro, et cetera. How's that fuel? To have seen that. It was I know it's going to do that. And I just want to say like I think Sam is obviously like a once in a generation founder. I think when he's done with OpenAI is extraordinary. And when he launched ChatTBT, 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. So there were all these other functional responsibilities. And so being able to just play a small part in giving some advice when necessary. And he would take what he wanted to discard others. But I think Lenny maybe this goes to another thing, which is all I tried to do with Sam as what other people did for me. When I started before my common year as a person named Michael Cible, 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 wasn't my board. And I asked him, I said, how do I pay you? And he said, well, I want you to pass a song to other founders. And I would meet with a lot of people in the valley. And there was this incredible culture of generosity that we all were going to win if the ecosystem was healthy. And the ecosystem would be healthy if we all helped one another. And you kind of pay it forward. And so 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 learned by teaching as well. Final question. When someone joins their B&B, there's a very long standing tradition of sharing a fun fact about yourself or maybe the longest standing tradition. It's always tough on the spot, but I'm curious Brian, if there's a fun fact that you want to share about yourself, then maybe people don't already know. 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, I'd take me to the Norman Rockle Museum and I would sit and frow, you know, his beautiful illustrations. They're really paintings, I should say, they 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. When I got study older, one of my friends, I went to his house, but I'm going to 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 table and he had like this vellum paper and he had a tea square and a drawing triangle and a protractor. And I just they're cool. They were really cool looking tools. And there were basically floor plans and architectural drawings. So I got into architectural and landscape design. And it's like eight or nine. And that led to my interest in architecture. I went to RPI was a freshman 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 to film an animation. Then I got involved in environmental design. I realized that if you buy stock in a company, you could get these cool glossy angle reports. This is kind of when the internet was kind of like naysand and people still male and your reports. So I got my dad to buy a few shares at some Disney stock. And I got these renderings in the end 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 its peril life. Whereas playing ice hockey. And I thought I was going to play college hockey. My dad was really into it. I was really into it. And I had our teacher in high school at this military school. That's another fun fact. I basically went to a military high school. Wow. And at this military sports academy kind of oriented high school. I had the same art teacher from eighth grade to 11th grade. And that's not a good thing by the way. I don't see any good thing because I was not diversifying my skills. And so I leave this high school because I wanted to pursue different interests than hockey. And I transferred 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 Miss Williams. And she sees my artwork. And by the way, my mom was nervous about me becoming an artist. She said, "Tell me I chose a job for the love and I paid no money. Susan chooses 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 you're going to pay less than a social worker." So I think my parents, you know, they were supportive of me going to art, but they were very nervous. And then Miss Williams told my mom, she said, "Don't worry. He's going to be a famous artist one day." I wasn't dependent because of famous artists. But what that did is I think it gave everyone the confidence for me to pursue art. I ended up being one of the 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 at the Rotanian School of Design. Right? I ended up going to RISD. It's like, you know, it's kind of like MIT for design or whatever. It's a prestigious art and design school. But I got to RISD. And I realized I was born a hundred 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 I needed that I had. And that's when I was in my fresh beer of college. I learned about a funk field called industrial design. They said industrial design is the design of everything from a toothbrush to a spaceship and everything in between. And really Lenny, maybe just around the story because that was a fun fact, but I'm kind of just, 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 industrial designer is different than a graphic designer because an industrial designer, you have to actually understand, you have to work with engineering in your training. You have to, like I worked with mechanical engineers, electric engineers, you have to understand manufacturing. And industrial design is very accountable to sales. If you design a building in architect and you design office building, Houseboy doesn't get leased.
The architects usually not on the hook for it, but if you're industrial design your design a product doesn't sell You're like kind of on the hook for at least people soon you didn't design a good product So you 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 Gebya and the day of graduation just looks to me says Brian I think we're gonna start a company together one day and I had no idea what he was referring to So I moved to Los Angeles where work as industrial design for two years When one day I got a package in the mail to change my life I opened this package and it's a sea cushion Well, they handle on it and it's a letter from Joe my my friend from RISD. He said I started a company In everyone in San Francisco. I live in San Francisco and all these people are starting copies you should come here And this is in 2007 YouTube had just come out. I like seeing all these Steve Jobs keynotes finally on YouTube I didn't know who he was I never heard his voice before before YouTube and They'll 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 of old Backseat of old Honda Civic I get to San Francisco and Joe tells me the rent is $1,150. I don't have enough made a pair rent This design conference came to San Francisco all the hotels are sold out We said what if we turned our house into a bed and breakfast for design conference I didn't have any beds, but joy at the reverts we call the 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 SAP 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 what listen to you has these qualities But I think that a lot of companies is like we're a body and the companies are cut off at the head They're disembodied from their heart and they're often really biased trips one side of their head And I think it's some of the greatest scientist played musical instruments like Einstein. I mean, I think that like Being a whole well-rounded way of thinking about the world is good. So anyways That's my final thought. I love that fun fact because it is 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 of Airbnb people hear that story over and over because it's 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. Thank you, Lenny Thank you. Congratulations. I really you're doing. Thanks Brian. Bye everyone 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 a leaving review as that really helps other listeners find the podcast You can find all past episodes or learn more about the show at Lenny's podcast.com See you in the next episode
Podcast Summary
Key Points:
Founders often compromise their vision to please others, but clarity and alignment are more effective.
Micromanagement is distinct from being "in the details"; leaders must know details to assess performance.
Airbnb eliminated the traditional product management function, merging inbound product development with outbound product marketing.
Program management tasks were offloaded to specialists, and the product marketing team was made smaller and more senior.
Designers often feel frustrated, treated as a service organization rather than integral to product development.
Large companies can develop silos, dependencies, politics, bureaucracy, and complacency, slowing innovation.
Performance marketing is like a laser (good for specific targets), while brand marketing is a chandelier (broad illumination); product marketing educates users.
Airbnb uses a rolling two-year roadmap updated every six months, with releases in May and November, ensuring the whole company rows in the same direction.
The CEO should act as the chief product officer in a product or tech company, staying deeply involved.
1
Delegating too much can lead to dysfunction and slow progress, contrary to common advice.
Summary:
In this podcast episode, Brian Chesky, CEO of Airbnb, discusses his philosophy on leadership and product management. He argues that many founders apologize for their vision, leading to confusion; instead, clarity and alignment make everyone happier. He distinguishes micromanagement from being "in the details," emphasizing that leaders must understand details to evaluate performance.
Chesky explains Airbnb’s restructuring of product management: merging inbound product development with outbound marketing, offloading program management to specialists, and creating a smaller, more senior product marketing team. He notes that designers often feel frustrated, treated as a service rather than core to development. He describes how large companies can devolve into silos, dependencies, politics, and bureaucracy, slowing innovation.
On marketing, he contrasts performance marketing (a laser for specific targets) with brand marketing (a chandelier for broad illumination), advocating for product marketing that educates users. Airbnb now uses a rolling two-year roadmap updated every six months, with company-wide releases in May and November. Chesky believes the CEO should be the chief product officer, staying deeply involved in products.
He reflects on a cycle where founders delegate too much, leading to dysfunction, and then must retake control to drive alignment and speed.
FAQs
Founders often apologize for how they want to run the company and find a midpoint between their vision and their team's desires, which leads to everyone being miserable due to a lack of clarity.
Micromanagement is telling people exactly what to do, while being in the details means staying involved to understand performance, similar to how a board oversees a CEO without dictating actions.
He combined inbound product development with outbound marketing, off-loaded program management to program managers, and made the team smaller and more senior, focusing on influence rather than control.
Designers often feel frustrated with the product development process, as they are treated as a service organization rather than integral to development, leading to compromised work.
Airbnb uses a rolling two-year product plan updated every six months, with releases in May and November, allowing the entire company to work together and row in the same direction.
The CEO should act as the chief product officer, staying deeply involved in product details to ensure alignment and drive the company's vision.
Chat with AI
Loading...
Pro features
Go deeper with this episode
Unlock creator-grade tools that turn any transcript into show notes and subtitle files.