Brian Chesky’s new playbook

Summary

In this insightful podcast episode, Brian Chesky, CEO of Airbnb, shares his transformative approach to leadership and company management. He talks about the journey of becoming more involved in the finer details to streamline processes and enhance efficiency within Airbnb. Chesky explains the company's departure from traditional growth channels, choosing instead to focus on creating the best product and storytelling. He discusses the importance of leaders staying in the details and how Airbnb's new roadmap and product strategies reflect a cohesive direction that fosters creativity, alignment, and growth.

Highlights

• Brian Chesky emphasizes the need for leaders to be actively involved in company details, distinguishing this from micromanagement. 💼
• Airbnb moved away from divisional structures and embraced a functional model to enhance coordination across teams. ⚙️
• The company now relies on a unified product roadmap that embraces both development and marketing aspects for coherent storytelling. 🚦
• Chesky discusses the cultural shift at Airbnb, focusing on returning to design roots and reducing reliance on traditional advertising. 🎨
• He highlights the significance of cross-functional teams collaborating closely on projects to drive consistent growth and innovation. 🤝

Key Takeaways

• Don't shy away from being hands-on as a leader. Great leadership involves being detailed and understanding the intricacies of the product and company. 🔍
• Airbnb has shifted focus from traditional growth avenues like paid advertising to innovative strategies centered around product excellence and storytelling. 🚀
• Creating a cohesive organizational structure where everyone is aligned on goals can drastically improve speed and efficiency. 🌟
• Product managers should integrate marketing and storytelling in their roles for better product distribution and recognition. 📈
• It's important to focus on big-picture goals while managing minute details, ensuring alignment in all company departments. 🎯

Overview

In this episode, Brian Chesky, CEO of Airbnb, opens up about his radical approach to reinventing company culture and operations at Airbnb. Reflecting on his journey, Chesky explains why moving away from traditional paid growth strategies in favor of focusing on exceptional product design and story-centric marketing was pivotal. This shift has redefined not just their internal processes but also how the market perceives Airbnb.

Chesky highlights key changes such as eliminating divisional structures, switching to a single cohesive roadmap, and integrating marketing within product management functions. These moves have been essential in fostering a unified direction within the organization, allowing for innovation to flourish and ensuring that everyone works toward common goals. This episode provides a masterclass in effectively balancing detailed involvement with broad strategic oversight.

Through anecdotes and real-life examples, Chesky articulates the importance of hands-on leadership. He candidly discusses the challenges and rewards of being deeply involved in every detail of the company’s transformation. Listeners will gain insights into the power of clarity and cohesion in leadership, and how aligning the entire organization on a bold vision can lead to impressive scalability and success.

Brian Chesky’s new playbook Transcription

• 00:00 - 00:30 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 what everyone really wants is Clarity what everyone really wants is to 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
• 00:30 - 01:00 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 leader 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
• 01:00 - 01:30 today my guest is Brian chesy Brian is the CEO and co-founder of Airbnb which he started in his apartment with his co-founders Joe Nate and has turned into an80 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 depth explanation of what's
• 01:30 - 02:00 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 road map across the entire company and Brian staying very close to every design and every feature we also get a bit into his
• 02:00 - 02:30 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 chesy 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
• 02:30 - 03:00 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 to navigate professional
• 03:00 - 03:30 pitfalls leading to more responsibility faster promotions and bigger impact Guided by worldclass 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 spent 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. comom
• 03:30 - 04:00 Lenny to learn more that's sidebar. comom 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 road map updates and you're spending your days basically putting out fires a better way is possible introducing jira product discovery the new prioritization and
• 04:00 - 04:30 Road mapping tool built for product teams by atlassian with Juro 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 road maps with any stakeholder in seconds and it's all built on jira 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
• 04:30 - 05:00 that you want can contribute ideas feedback and insights in Juro product Discovery for free no catch and it's only $10 a month for you say goodbye to your spreadsheets and The NeverEnding alignment efforts the old way of doing product management is over ReDiscover what's possible with Jiro product Discovery try it for free at atlassian
• 05:00 - 05:30 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 airbeam be 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 sucessful podcast yeah congrats on everything it is awesome I appreciate it congrats to you too Brian things seem to be 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 uh what is going on with product management at Airbnb you made
• 05:30 - 06:00 some comments at figma config and a lot of people got this impression that you eliminated product management 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 I spoke at figma you know like four or five months ago
• 06:00 - 06:30 I spoke to a room of designers I then uh 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 desires room started shearing that's right so I want to I want to I want to talk about two things what I actually meant because I didn't actually get rid of the people and also why do 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
• 06:30 - 07:00 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 when you were Z but we didn't get rid of people helping Drive the product what we did is we combined what one might call the
• 07:00 - 07:30 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 offboard much of the program management functions that product managers may do to actual program managers a lot of people the product management title are actually program managers so we actually started offboarding some responsibilities to program management the last thing we did
• 07:30 - 08:00 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 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 didn't work my question is
• 08:00 - 08:30 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 much more responsibility the other thing though is that they do not control or drive designing or engineering we are a very purely functional model they manage by influence do not have
• 08:30 - 09:00 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 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 want to say I I don't I don't know if I can speak on behalf of all the designers but having talked to live designers I think designers and the valley are very
• 09:00 - 09:30 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 because Silicon Valley often treats design as a service organization you know like design is catching things before it Go outs the door it's not actually typically part of the develop process and I think this is
• 09:30 - 10:00 not just bad for design I think it's bad for product managers and Engineers because 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 accumulating technical debt the next problem you'll see is that there's a lot of dependencies so five teams are going s different directions but they
• 10:00 - 10:30 all need a payment platform and so that on 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 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 own groups so now they're really
• 10:30 - 11:00 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 politics it's so now politics that brw in the company and suddenly people get more subdivided more
• 11:00 - 11:30 subdivided subdivided and that creates another problem which we call bureaucracy and that bureaucracy means it's hard to know who is doing what you can't like people are going in different directions and that creates a lack of accountability 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 growing company becomes a big slow moving bureaucracy this is a general Arc winds up happening and then you end up
• 11:30 - 12:00 having this situation where company's done like 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 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 horis is how Coast's engineering and marketing and marketing is a lot of companies are like the waiters Engineers
• 12:00 - 12:30 are like the chefs and the chefs yell at the waiters 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 had to talk about the products that they're building so this is the problem that we had and I 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 Performance Marketing a laser uh
• 12:30 - 13:00 actually my co-founder who obviously know well Joe used to have this metaphor of lasers flash bulbs and chandeliers if you want to light up a room performance marking is 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 in Balance supply and demand then Performance Marketing is really good it literally lasers in Performance Marketing though doesn't create very good accumulating
• 13:00 - 13:30 advantages because it's not an investment now if you want to build it permanently like booking.com if you have a really highi now you can have a Performance Marketing Arbitrage business but assuming you don't want 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
• 13:30 - 14:00 Marketing but they're never really educating people about new things they're making and shipping and because no one's marketing new things they shipping there's no purpose to ship new things because 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 now what we do is we do we have a rolling two-year road map we don't even really do an annual plan I mean we as you remember Lenny you're at Airbnb we would have like three-month
• 14:00 - 14:30 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 road map 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
• 14:30 - 15:00 product marketing so they're figuring how people are going to 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 at 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 a story to
• 15:00 - 15:30 people but a story also is a really helpful way to develop a cohesive product right we wanted a company where a thousand 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 I could go into a lot more detail but I probably will'll stop there that was amazing you touched on all of the things I want to talk about so I'm gonna oh geez so we can go deeper and deeper because the rabbit exactly exactly so
• 15:30 - 16:00 I'm going to pull on a couple threads the first is this idea of a single road map you talked about and what this reminds me of is I was talking to another very prominent CE 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 in politics and then eventually you
• 16:00 - 16:30 realize I need to take the RS 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 Le Founders or engineering Le 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
• 16:30 - 17:00 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 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 the founder CEO should be that person so when we were starting Airbnb
• 17:00 - 17:30 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 in the product and I always remember Lenny when you this there was this
• 17:30 - 18:00 Paradox where the less involved I was in a project I mean there was there they 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 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 was because I was too involved
• 18:00 - 18:30 right because people assume that that our natural equilibriums to move fast 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 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 you you end up in a
• 18:30 - 19:00 situation where you're delegating down so I think that things were getting worse and slower and slower and slower 2015 2016 2017 2018 2019 and by 2019 we were spending a billion dollars on AdWords we weren't really like investing in the brand we're doing a huge amount of AB testing I think AB testing is important in in times but like let me actually let me let me let
• 19:00 - 19:30 me let me clarify you be testing we don't test blue versus green we have a control and a treatment like I think we did with ere so we have a design we might do a hold back occasionally to see how the thing is working but if we do an AB 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 but never you can never change it and imagine 10 teams doing AB testing
• 19:30 - 20:00 and like imagine if you designed software the way designed a house or designed house the way design software and we AB test a sofa and we said like well how does a sofa work and it seems like with this sofa that we've AB tested people spend more time in the living room so therefore like people are going like this room better but actually the sofa has a relationship to the end stands which have relationship to the lamps which have relationship to the carpet or the rug which have relationship to the television which have relationship to the house and everything else so you have to think
• 20:00 - 20:30 about the whole cohesive system and I started realizing that I remember working with as I asked one person on your team somebody you know well and I asked him I said why is our 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 he 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
• 20:30 - 21:00 2019 I don't know what to do I'm like the product is slow the app seems 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 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 and getting 20 hours of productive work done which is like just like a crazy ratio a week and I didn't really quite
• 21:00 - 21:30 know what to do and then right before the pandemic I meet two people that really affected how I thought about things the first was heroki asai heroi now works at Airbnb he's one of my Executives and actually product design product marketing design and marketing repor 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
• 21:30 - 22:00 of marketing Communications and 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 I got reacquainted a person named Johnny IV and Johnny I was the head of industrial design then Chief design offic or apple and they described this
• 22:00 - 22:30 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 like the services is turning into Division and they are just so big that I think it's you know not a oneto one anymore but they are still technically run this way and I had this image of not being divisional because we were running like we 10 divisions we had a flights Division and you know we had a homes
• 22:30 - 23:00 division which was divided to proost and core host and Lux 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 we had like these 10 different divisions all going in 10 different directions and I created this culture where everyone want to be a business manager and or a 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 turn and this was all about me delegating
• 23:00 - 23:30 responsibility the problem is if you're running a divisional company you're a product Leed 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 try to adjudicate different issues between groups so then the pandemic occurs and I had this image on 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 and
• 23:30 - 24:00 bolus it was October 2019 and I told them I had this dream that I left the company 10 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
• 24:00 - 24:30 routes 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 both growth are slowing and that was exactly kind of what was happening and then the pandemic occurred and we lost 80% of our business in8 weeks and then suddenly we're like oh my God like I remember having basically staring into the abyss
• 24:30 - 25:00 and luckily I've never had a near-death experience but the way it's been described to me is it's like your flly flashes before you 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 going to run it this other way where I'm going to get back and evolved 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 are like what
• 25:00 - 25:30 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 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 you think we're doing too many things for me to ever be able to document I'm like what but anyways we have eventually got everyone to write everything down and I said okay we can
• 25:30 - 26:00 do about 20% of these things and so if everyone says oh I might it be 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 the leaders of the team we went to a functional model we went back to a startups so we said we're not going to have divisional leaders we're going to have design engineering product and which turned to product marketing and
• 26:00 - 26:30 marketing and Communications and sales and operations all the functions of a startup I said we're goingon to 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 to 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 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
• 26:30 - 27:00 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 they exist or there's designers but there's design leaders who who lead the people a design leaders job should be managing the design first the people second that's Johnny did or like they're they're interchangeable I I could never imagine Johnny AV at Apple just being a manager of people he was looking and designing the work with the team how do you manage
• 27:00 - 27:30 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 going to have one continuous conversation metrics are going to be subordinate to the calendar so we're going to have a road map it's going to be a two-year road map well update the road map literally every month people may Wonder well like what if the world
• 27:30 - 28:00 changes yeah it changes every day so the road map's something where the next month hasn't changed but two years out it changes it's a rolling road map and by the way if Ukraine like gets invaded and you want to like provide housing for refugees you can still pivot people and adapt very quickly we house 12 12,000 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 made the group
• 28:00 - 28:30 much smaller I took a lot of product managers I reassign as program managers I had many of them trained an actual program management because their roles got much bigger um program management airb is a high status job a lot of companies it's like a coordination job and me 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 road map so every single thing in the company with the exception of some infrastructure projects have have to be on the road map and then I'm going to review all the work and so we create the
• 28:30 - 29:00 CEO review schedule where I said I'm getting back in the involved in the project and I'm going to design I'm going to 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 p program manager that would score all the projects either they're green yellow or red mean 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 use the reviews of the work every single week
• 29:00 - 29:30 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 an individual engineer cuz imagine it's like we're a car company and I I see the car prototype every week
• 29:30 - 30:00 and I notice there's a there's a there's a something about the tires off now I 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 unal we all these reviews I didn't
• 30:00 - 30:30 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 we also started really building out much more of a marketing Communications and creative function we built out our own in-house creative agency so we use production Partners but we don't use widening kendi or Sher or any those anymore we actually build our own in-house agency so to speak which is a
• 30:30 - 31:00 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
• 31:00 - 31:30 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 make 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 run a company they basically find some
• 31:30 - 32:00 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 the company the people you want is that's a good way to make everyone miserable because what everyone really wants is Clarity 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
• 32:00 - 32:30 time so we have entire project 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
• 32:30 - 33:00 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 a good job people think that great leader 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 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
• 33:00 - 33:30 EPO is a Next Generation AB testing and feature management platform built by alums of Airbnb and snowflake for modern growth teams companies like twitch Muro clickup and DraftKings r on EPO to power their experiments experimentation is increasingly essential for driving growth and for understanding the performance of new features and EPO 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
• 33:30 - 34:00 where I could 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 Appo also makes it easy for you to share experiment insights with your team sparking new ideas for the AB testing flywheel EPO Powers experimentation across every use case including product
• 34:00 - 34:30 growth machine learning monetization and email marketing check out EPO at geo.com Lenny and 10x your experiment velocity that's geo.com Lenny 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 done is shut down traditional growth channels or at least limited them PID
• 34:30 - 35:00 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 is 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 ideal logical or have to go all the way to 100 you I still think
• 35:00 - 35:30 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
• 35:30 - 36:00 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 that 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 another way saying it Lenny every product manager should be interconnected and know what everyone else is doing they shouldn't be independent siloed unless they really are running like separate companies or separate orgs and
• 36:00 - 36:30 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 you know 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 grow slowly and
• 36:30 - 37:00 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 want to 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 em and said you can't delegate understanding if you're going to do ab experiments or
• 37:00 - 37:30 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 TR to think about product management expanding the
• 37:30 - 38:00 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 going to work with not technical functions right if they're only work technical functions that's fine but they don't work at 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 as few layers between a CEO and
• 38:00 - 38:30 other people if you're a CEO every direct to your direct should be a implicit DOA line to you so I treat every direct to my direct as if they're a direct report a DOA 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
• 38:30 - 39:00 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 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 lot of the things you're talking about I'd love to hear just some of the stuff you're launching let me
• 39:00 - 39:30 just back up seleni so 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 this unique inventory and people you know list 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 going to get and so a lot of guests have described checking into Airbnb as a Moment of Truth where
• 39:30 - 40:00 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 going to get you know exactly you're going to get and so what we found is that reliability is airb be's Achilles heel or at least it has been
• 40:00 - 40:30 that you know with hotels you know you're going to get an Airbnb you don't always know you're going to get and so we asked ourselves what if we could combine the uniqueness of Airbnb with the reliability that you've come to speca 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 use all
• 40:30 - 41:00 the signal to create the top two million homes that this collection of two million homes that we call guest favorites because the homes the guest rate the highest we think combine the uniqueness of Airbnb with the reliability to come to expect 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 readings and reviews you see as you know Airbnb is built on a system system of trust and we invented this new way for people to trust one another you know at
• 41:00 - 41:30 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
• 41:30 - 42:00 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 was designed as this hodg Podge Thing by different teams over many years oh here's the other thing Lenny when you were at Airbnb we had a guest team and a host team we don't have a guest team and host team we have a design team we have a marketing team we have an engine engineering team the reason we don't break the app into guest and host anymore is because
• 42:00 - 42:30 reviews affect guest and host it turns out that almost everything involves connecting the guest and host and you have separate teams that tend to have separate road maps that go in separate directions they become incompatible so we have product marketers that responsible guest and host things but there's the the designers are in 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 want to make sure
• 42:30 - 43:00 that we have designers and Engineers covering a much larger surface and so 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'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 skew morphism the
• 43:00 - 43:30 2010s have been dominated with the 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 schor fism 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
• 43:30 - 44:00 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 a 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 think I think it's going to be where a lot of interface design is going and we built this AI powered photo
• 44:00 - 44:30 tour where we created our own AI computer visiting language that we trained on a 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 you know we could have theoretically launch a lot of these features but you know really getting them to work together has been key and guest favorites has required the guest people you know you you have to work
• 44:30 - 45:00 with guests you have to work a host you have to essentially you know you know have you have to like 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 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 to a host that's like I think how many host are there 7 million something like
• 45:00 - 45:30 there's there's there's 7 million listings yeah over 7 million listings 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 site so 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 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 host and to have great hosts they need great tools and so if you want to
• 45:30 - 46:00 create a great experience for guests it often starts with building great tools for hosts to enable them to provy 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 and we also felt like if we put te in the 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 they do put a lot of care in now speaking of great products a defining characteristic of briyan chesy in my mind is how big you make people think
• 46:00 - 46:30 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 tenx 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
• 46:30 - 47:00 these really ambitious goals as you know there was a there was a saying inside of Airbnb it was add a zero add a zero at the end which is to make to imagine something order man to bigger the exercise isn't necessarily to say if people say they want to hit a goal I say okay I added to 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
• 47:00 - 47:30 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 you reconstruct them so the first thing
• 47:30 - 48:00 is I think by adding a zero at least conceptually for teams to helps some understand a problem the second is I think one of the most important things for a Founder leader to do is set the pace to a 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
• 48:00 - 48:30 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 are 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
• 48:30 - 49:00 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 you know 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 on themselves and so the role of a leader is to see potential in
• 49:00 - 49:30 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 like 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
• 49:30 - 50:00 way to know if a team could do better is if they're life dependent I could they do it and Indie Grove used to say that there's competency and motivation and motivation is if they're like 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 principal thinking and if you do
• 50:00 - 50:30 that then I think that's going to be the opposite of these slow movings kind of soulc crushing bureaucracies 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 with some of the things you've talked about of say do it now we're not going to wait another week to Circle back and the stuff you talked about of taking on the CPO role not having a CPO and also all these launchers it sounds like a lot of work and aot of hours what have you learned about avoiding burnout and creating balance and also just
• 50:30 - 51:00 helping people on your team avoid burnout and creating balance so first of all um I want to give you a a a very surprising learning I weirdly now the more I get involved this is so weird the more in the details I am the more time I have in my hands that's a paradox and I want to explain that Paradox it doesn't make any sense but 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
• 51:00 - 51:30 like I would be working 800 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
• 51:30 - 52:00 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 people were rowing in the same direction that I wasn't reacting before I would get 10 surprises nine were bad now I get 10 surprises
• 52:00 - 52:30 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 I wasn't involved in because 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 this work to fix something because we weren't involved in the very early eight stages so I I was much more involved I had a lot less time on my hands initially and now
• 52:30 - 53:00 I actually weirdly have a lot more time on my hands but to answer question on burnout 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 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 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
• 53:00 - 53:30 this temptation to work more and more and more hours and sometimes you need to say 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 it a practice to step away from the work and so here's some of 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 more
• 53:30 - 54:00 intensely so you know I would you wouldn't be a parent every 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 in a pelaton I'll go to the gym three or four times a week and do weights I 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
• 54:00 - 54:30 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're in your life is your relationships I think the two govern I think the three things 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 his 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
• 54:30 - 55:00 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 if to get people up the 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
• 55:00 - 55:30 constant in touch with including old friends so I have a group of high school friends we have a group chat we take one to two trips together Tri together 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 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 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
• 55:30 - 56:00 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 Bal of each and you might call family relationships you know I'm just I'm single but you know that would
• 56:00 - 56:30 be another version of it 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 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 reach 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
• 56:30 - 57:00 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 reacting so people will email them and they'll wake up and they'll repond 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
• 57:00 - 57:30 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 her as long as you thought you would be because it's possible it would completely change how you prioritize your time and think
• 57:30 - 58:00 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 or spending your
• 58:00 - 58:30 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 get 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 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
• 58:30 - 59:00 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 you asked really good questions and by way thank you I um so I'll I'll share a few thoughts I was I was with Sam mman 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
• 59:00 - 59:30 he was like really surprised he's like whatat 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 when I first took off I think I
• 59:30 - 60:00 thought I like 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 prop 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 was saying he said it took me four years to learn to paint like Raphael but a lifetime to learn to paint like a child
• 60:00 - 60:30 and so I've tried to always see the 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 a 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 ERS that mit's MIT Sloan is named after and actually the founding of divisional companies which I believe was
• 60:30 - 61:00 Dupont they were making powder for Gunpowder the war ends what do we do with powder turns out powder can be used for paint but the way you sell gunpowder and paint our 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
• 61:00 - 61:30 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 youthful then than somebody two years ahead of them that knows like the latest distribution
• 61:30 - 62:00 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 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 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
• 62:00 - 62:30 as they don't become something then they're going to be okay and so you you have to always be evolving learning growing and the canvas keeps getting bigger the mountain toop keeps getting higher and I feel like I'm just getting started and I hope that you know I I don't know how long you intend to do the podcast but I intend to do this for a long time and if you do or or whatever we'll definitely want to have talks and I hope years from now Lenny I hope 70%
• 62:30 - 63:00 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 if 90% I say I don't believe anymore then I'm like you know kind of delusional and wrong but if but 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
• 63:00 - 63:30 Sam Alman I'm 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 Etc how's that feel to have seen that it was I I had no who was going to do that and I just want to say like I think Sam is obviously like a once in a generation
• 63:30 - 64:00 founder I think what he's done with open ey is extraordinary and when he launched chat gbt I had known him for a really 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 then research Orient part of open AI 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
• 64:00 - 64:30 would take what he wanted to disc 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 commentator there's a person named Michael cyel he's in y commentator and he used to meet with me and give me advice and he wasn't an official adviser he wasn't an investor I didn't hire him or anything like that he wasn't board and I asked him I said how do I repay you and he said well I want you to pass
• 64:30 - 65:00 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 going to win you know if the ecosystem was healthy and the ecos 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
• 65:00 - 65:30 teaching as well final question when someone joins Airbnb there is a very long-standing tradition of sharing a fun fact about yourself who 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 want to share about yourself that 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 5 years old I remember my parents like take me to the Norman Rock Museum and I would sit in
• 65:30 - 66:00 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 when I got soly older one of my friends I went to his house I'm gonna say I was like eight or nine years old and his dad was basically like redoing his deck but his dad
• 66:00 - 66:30 decided to design it himself I think maybe's an architect so he had this giant dining room table and he had like this velum paper and he had a t-square and a drawing triangle and a protractor and I just the 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 was like eight or nine and that led to my interest in architecture I went to RPI was a freshman of co uh of high school to do like a pre-ol program then I got into
• 66:30 - 67:00 like more and more drawing and figure drawing then I got to film and animation then I got involved in in 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 Nason and people still mailed annual reports and so I got my dad to buy a few shares at some Disney stock and I got these renderings and the had report of theme parks and I started like drawing like and designing like theme parks in communities
• 67:00 - 67:30 and I was at this private school for actually for hockey because I had it parallel life where I was playing ice hockey and I I thought I was going to 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 wow did not know that and at this military Sports Academy kind of oriented high school I had the same art teacher from 8th grade to 11th grade and that's
• 67:30 - 68:00 not a good thing by the way I saying this 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 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
• 68:00 - 68:30 nervous about me becoming an artist she used to sell me I chose a job for the love and I paid no I got paid no money she used to 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 going to pay less than a social worker so I think my parents you know they were support 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 to become a famous artist but what that did is I think it gave everyone the confidence for me to
• 68:30 - 69:00 pursue art I ended up being one of the a winner there were multiple winners of a national art competition and I had my artwork displayed in the retunda gallery that then led to me getting a scholarship at the r School design where I end up going to Ry 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 it's prestigious Art and Design School but I got to risti and I realized I was born a 100 years too late for what I wanted to do which is you know draw and
• 69:00 - 69:30 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 that I had and that's when I was in my fresh beer of college and I learned about a funk field called industrial design they IND they said industrial design is the design of everything from a toothbrush to a space ship and everything in between and really Lenny maybe just to rande the story because I know was a fun fact but I'm kind of just this is the pre
• 69:30 - 70:00 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 you know you have to work with Engineering in your in your training you have to like I worked with mechanical engineers electric Engineers you have to understand manufacturing industrial design very accountable to sales if you design a building an architect and you design office building office building doesn't get leased the architect is
• 70:00 - 70:30 usually not on the hook for it but if you're industrial designer you design a product doesn't sell you're like kind of on the hook for it at least people assume you didn't design a good product so you 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 Ry the biggest value I got in addition to learning industrial design was I met my co-founder Joe gbia and the day of graduation Joe looks to me he says Brian I think we're going to start a company
• 70:30 - 71:00 together one day and I had no idea what he was referring to so I moved to Los Angeles where I work as an industrial deser 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 SE cushion with a handle on it and it's a letter from Joe my my friend from Ry he said I started a company in everyone in San Francisco I live in San Francisco and all these people are starting cupies you should come here and this is in 2007 YouTube
• 71:00 - 71:30 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 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 to work and I quit my job my boss is dumbfounded and I pack everything the old uh old uh backseat of old Honda Civic I get to San Francisco and Joe tells me the rent is
• 71:30 - 72:00 $1,150 I don't have enough money to pay our rent this design conference come 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 Jo had through our beds we called the airb 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 irban be different because there's not a lot of designers or artists running Fortune 500 or SCP
• 72:00 - 72:30 500 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 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 their heart and they're often really biased towards one side of their head and I think some of the greatest scientists played musical instruments like Einstein I mean I think that like being a whole well-rounded way of
• 72:30 - 73:00 thinking about the world is good so anyways that's my final thought 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 you sharing that I also love that it transitioned into the creation Story of airb B which happens a lot at airb B people hear that story over and over because it's h 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 and congratulations everything you're doing
• 73:00 - 73:30 thanks Brian bye everyone thank you so much for listening if you found this valuable you can subscribe to the show on Apple podcast 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 Lenny podcast.com see you in the next episode