Lenny's Podcast: Product | Career | Growth - Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product)

Episode Date: September 1, 2024

Vlad Loktev spent 10 years at Airbnb, where he started as an IC PM and quickly advanced to lead the core Airbnb marketplace business and then GM the entire homes business, managing over 1,000 people and reporting directly to CEO Brian Chesky. He recently left Airbnb and joined Index Ventures as their newest partner. Vlad was my manager at Airbnb for many years, and is the person I credit most for teaching me how to be a great product manager. Prior to Airbnb, Vlad spent a year at Zynga, where he helped grow Words with Friends to over 14 million daily active users. In our conversation, Vlad shares:• Insight into Brian Chesky’s leadership style• Why success as a PM is all about impact, impact, impact• Why chaos can be good• Why as a leader it’s OK to let some fires burn• Why you should learn to “poke the bear”• Balancing product release speed with quality• Lessons on prioritization, decision-making, and organizational design• Advice for founders on building company culture• Much more—Brought to you by:• Pendo—The only all-in-one product experience platform for any type of application• Vanta—Automate compliance. Simplify security• Eppo—Run reliable, impactful experiments—Find the transcript and show notes at: https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev—Where to find Vlad Loktev:• X: https://x.com/vladimirloktev• LinkedIn: https://www.linkedin.com/in/vladimirloktev/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Vlad’s background(02:54) Reflecting on transformative years at Airbnb(04:28) Skills and mindsets for success(11:03) Impact-driven mindset(13:16) Saying no and inquiry before advocacy (17:54) “Poking the bear”(22:46) Psychological tools for leadership(30:08) Building and scaling teams(36:12) Letting fires burn(47:34) Embracing chaos(54:40) The unsell email strategy(01:02:01) Finding your place in an organization(01:05:38) The importance of company culture(01:13:16) Airbnb’s unique approach to product management(01:26:41) Failure corner(01:31:32) Lightning round and final thoughts—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

What was it like managing me, Vlad? Most importantly, how painful was it to manage me? Man, how much time do you have? I used to joke with people that you're kind of a Jedi where you get crazy stuff done, really hard stuff done, in a really subtle and a really unique way. I've always used inquiry versus advocacy. A lot of people approach a conversation with a point of view,

and they begin advocating immediately. We should do this or no, we should not do this, right? Me, I always took the opposite approach. I inquire first. I'm going to ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision. Is there something we can share about just what you learned for Brian about thinking big?

I remember talking to Brian one day. He was like, something just feels off right now. And I remember asking him, like, what do you mean? Our numbers are up into the right. His response was things are just too calm. Sometimes you want to create chaos in an organization to push the organization to think creatively and to actually like make leaps in product development. And I've always told myself, don't be afraid.

to poke the bear. What are some skills that you believe helped you be as successful as you've been? Impact, impact, impact, impact. That's the only thing that mattered. Today, my guest is Vlad Lockhev. This is a very special episode for me because Vlad was my manager at Airbnb for many years

and he's the person that I credited most for teaching me how to be an effective product manager and product leader. Within Airbnb, Vlad started as an ICPM. Five years later was leading product for the core Airbnb business, the homes business. A few years later was GM of the core homes business, reporting directly to Brian Chesky, managing over a thousand people, including design engineering and other functions.

He's also one of Brian's most trusted partners for most of his time at Airbnb. Before Airbnb, Vlad was a founder. He was also a senior PM at Zinga, where he grew the game words with friends to over 14 million daily active users. Even though Vlad recently moved into venture capital as a partner at Index Ventures, he will always be a product manager at heart to me. and I'm very excited for more people to get to learn from Vlad. In our conversation, Vlad shares the skills and behaviors and mindsets that most contributed to his success, including a ton of really tactical stuff, also the strategies and tactics that he's found most helpful in building and scaling a fast-growing org,

and his thoughts on Airbnb's current ways of working, including their move away from traditional product management and also their approach of thinking very top-down, which I thought was really insightful, and so much more, this podcast, I guarantee, will make you a more effective product leader, and I am very excited to share it with you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and helps the podcast tremendously. With that, I bring you Vlad Lockhev.

Vlad, thank you so much for being here, and welcome to the podcast. Thank you. Excited to be here. I think this is going to be an extremely special. episode. People will have heard in the intro that we've worked together for many years, and even more interestingly managed me for many years at Airbnb. I've also told you this before, but those years were probably, not probably, definitely the most transformative years of my career where I learned the most and the years that set me up for the success. I ended up having later,

and also the crazy work that I do now. So let me just say, I'm just really excited for other people to get a chance to learn from you and to learn from the things that you've learned that helped you be successful and helped me be successful. So, Thanks again for making time for this. Yeah, of course. Excited to be here. I mean, you were always a rock star. So you're a rock star back then.

You're a rock star today. So excited, excited to chat. I appreciate it. I don't know if I was a rock star at the beginning. This is where my first question was going to go is, what was it like managing me, Vlad? You're most importantly, how painful was it to manage me? Man, how much time do you have?

No. No, jokes aside, I've loved working with you, man. And I have to say, the one thing that I always deeply appreciated was that no matter how hard things were, you like always called out the elephant in the room. And so you always told me the stuff I did not want to hear. And, you know, large companies, things are growing, lots of things are happening. As a leader, you miss so many things. And so hearing actually what's happening and the reality of what you're dealing with, it was just so, so helpful. So I deeply appreciated that about you.

Wow, I think we're just going to be a love fest, but I feel like I was able to do that because I knew you'd react well and you needed to hear those things. This episode is brought to you by Pendo, the only all-in-one product experience platform for any type of application. Tired of bouncing around multiple tools to uncover what's really happening inside your product. With all the tools you need in one simple-to-use platform, Pendo makes it easy to answer critical questions about how users are engaging with your product and then turn those insights into action. All so you can get your users to do what you actually want them to do. First, Pendo is built around product analytics, seeing what your users are actually doing in your apps so that you can optimize their experience. Next, Pendo lets you deploy in-app guides that lead users through the actions that matter most. Then, Pendo integrates user feedback so that you can capture and analyze what people actually want.

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That's V-A-N-A-com slash Lenny. What I want to start talking about is talking through and spending time on some of the skills that you developed and some of the skills that you're essentially world class at in my experience that I think might be helpful to a lot of other people. I used to joke with people that you're kind of this Jedi. They have like Jedi powers where you just get crazy stuff done, really hard stuff done in a really subtle and a really unique way that I haven't seen other people work. And to show kind of the impact that has had, your gross trajectory to Airbnb is pretty absurd. When you joined, I think you were kind of the same level, maybe, maybe you're a level above.

of an I, you're an ICPM at Airbnb. And then five years later, you're a head of product basically for the homes business, which is the core Airbnb business. And then a few years later, you're GM for the entire Airbnb homes business, managing a thousand people, designers, engineers, research, marketing, all these functions. So I want to spend a little time on some of the things that helped you get to that point. Let me just start with just a broad question. Yeah.

What are some skills that you believe helped you be as successful as you've been? And that could be skills, maybe behaviors, maybe mindsets that helped you be successful. Well, first, thank you for that introduction. I'm a work in progress. So there are many things that I am constantly working on. I think for me, like when I reflect on my journey at Airbnb, it was more about the mindset rather than any kind of like skill. So, for example, my main mindset was impact above everything else.

So like impact, impact, impact. And that's the only thing that mattered, like basically my entire career. And so I woke up every day and I asked myself two questions, basically. Number one, what are the highest priorities for Airbnb today and over the next like three months? And then two, what can I do to actually make a meaningful dent in those priorities? Like, what impact can I have? And I always made sure that whatever I worked on was very aligned with a top priority for the company. And I would say if you find yourself in a situation where you're not working on the top priority of the company,

you should probably get a different job. Because at the end of the day, you're spending so much of yourself and so much time at your job. you might as well really go for it and work on the hardest thing you can find and somebody is willing to give you a shot to build something crazy. And so for me, like I always thought about what is the hardest thing that I can work on and how can I drive the biggest amount of impact. Now, oftentimes it's, you know, figuring out the priorities is relatively easy. There's typically clarity around what you have to focus on,

whether it's expanding a team and really like building out. a specific team, whether it's growth rate or focusing on the product quality or like closing deals and closing sales, you can typically figure out what the priorities are. It's oftentimes very hard to figure out how to make impact and like what impact even means. And so for me, like my motto there was always just learn the drivers of the business. So put like your day drop to the side for a second and just immerse yourself and understanding that. why certain behaviors exist on the product that you're working on, right? Can you influence that behavior?

Like, if you do X, what will happen, essentially? And I spent a lot of time actually blocking off, like, on my calendar, just time thinking through the drivers with the question of what are the drivers are going to have the most impact for the business. And I remember, like, when we worked on Instant Book together, I think this was like back in probably 2014, that was not a random project. There was so much thought behind why we should focus on Instant Book and what was the core problem with Airbnb at that moment in time and what impact we thought we could have on the overall trajectory of company. So that was impact, impact, impact, always just my motto, I guess.

Well, let's actually spend more time here because this is such like not only have I seen you do this well. I've also seen the impact this mindset has had. And I think people are listening to this. might be like, yeah, okay, impact, great. Yeah, work on impacting. But I think there's so much power to this that it's worth us spending a little more time on. Yeah, let's do. What do people do that's not this? Like, I imagine many people listening are like, oh, I work on things that are impactful

and doing great. What is it that you see that's not this? I think when a company matures, I think there is, you know, it grows, many more people join the team. The company gets bigger. At some point, a lot of people are working on similar things. You then teams start to form. then the entire department start to form.

And pretty quickly, I think a lot of people begin to realize that you're, like, you yourself are not in control of many things. And you actually depend on what other people do, right? And so a lot of people, and I've done this too, have focused a lot of energy day-to-day on the dependencies rather than the things that you yourself can do in your day-to-day. So, for example, what I've seen as an organization scale is people, transition from saying, I can do X, and they transition to saying, can the other team do Y so that I can do X? And I think that's a very dangerous place to be, because at the end of the day, like, you just need to let go of some of these dependencies.

Like, you're not going to move mountains every single day, and you've got to focus on the things that are actually within your control. So, again, it's more of a mindset shift. The other thing I would say is every single project that we worked on an Airbnb, we did back of the envelope math with assumptions to help us understand the impact that something would have. And you needed to at least, now those assumptions could be completely crazy and could be very challenging, but you at least needed to think through the mechanics of what you have to believe in order for this project to be a success. and for it to then make a big debt and whatever you're trying to achieve at the company. So every single thing, we did have that behind the scenes, and we spent a lot of time on this

to make sure that we were focused on the right things. I remember there was a project we were going to work on. I'm like, I think this is a big opportunity. Here's all my thinking on it. And what I didn't have is here's the lift this could potentially drive. Yeah. And so what you did is you just created this flowchart of all the levers of the business.

And then like, okay, you're talking about this sub-lever here. And if you move this 10%, here's the impact on the potential business. And you're right, and it is actually a big opportunity, but this is how you want to show it. Yeah, totally. The other thing I'll say is also equally important is saying no to a lot of things. And it's actually really hard because, you know, we are basically trained in condition to say yes, right? Like you go to school, you follow the rules.

Like, you listen to your parents. You don't want to disappoint people. And so when people ask for help, you help, right? And you want to be a really good teammate. But then at some point you realize that's actually not the job. And if you were to say yes to absolutely everything that you have to do at a company, you would be distracted all the time with like tons of things that will not make impact. Right. And so I learned very early on how to say no.

And it was hard emotionally. Like I've gone to many different debates and conversations, but ultimately, Ultimately, I think maybe it doesn't win you many friends in the short term, but in the long term, people realize that when you say no to something, there's probably a really good reason behind why that thing may not be as impactful today. And maybe we shouldn't even do it in the first place. And so I think doing the back of the avalan math and being really good a prioritization is one thing, but also not getting distracted with all the noise and all the different opinions that everyone's going to have at a big company is another big thing. So saying no is hard. So maybe two quick questions here. One is, do you have any tricks for how to say no well where someone's not like pissed off? And then the other question I'll just throw in. You can take him however you're on is what's your heuristic at how much people should like you as a PM?

Because you touched on like people don't need to necessarily love you. For saying no, first, you can't just be dogmatic and just say no for the sake of saying no and just disagreeing with people. You have to listen. So for me, the framework that I've always used was inquiry versus advocacy. And I don't know if you remember. We've talked about it in some context where basically a lot of people approach a conversation with the point of view and they begin advocating immediately. Meaning we should do this or no, we should not do this, right? Me, I always said the opposite approach and I still do.

I inquire first. I dial up inquiry. I tone down my advocacy, meaning. I'm going to respect the other opinion. I'm going to ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision. So in the beginning, dial up inquiry and then once the person who you're talking to feels heard and you actually have absorbed information and maybe you've changed your mind, maybe not though,

that's when you begin to advocate. So oftentimes you just come into these conversations where everyone just advocates, advocate, advocate, advocate, advocate. and you're talking past each other. You're not even like reflecting on what the other person is saying. And so that's been my, sometimes when I talk too much, I tell myself, wait, inquire, dial down advocacy, just take a breath, take a moment, take a beat, and actually ask some questions and see why the other person I feel so strongly. I think that's such a good specific thing you can do because a lot of, I think a lot of people

want to do what you're doing. They're like, okay, I'm going to listen. I'm going to ask questions, but then they get a reaction. Someone's like, hey, we need to change this thing on the landing page. And you're like, no, that's a terrible idea or that's going to take all this time. It's going to throw off a roadmap. And there's like this bodily like, oh, no, I need to stop this thing except. And so your advice here is like, pay attention to, am I talking too long?

I guess is that the advice? Am I talking too long? Am I saying too much and like start just inquiring instead? Yeah. Awesome. Totally. And lead with questions. Like basically approach every conversation with curiosity.

Like try, like, don't commend. because people usually like when they prepare for a meeting, I've seen many PMs do this, and you prepare with like, here's my view and here are the bullets that support my view. And that's the wrong way to approach it. I think what you want to go into a conversation are you start the conversation with questions. Prepare the questions that come from a place of curiosity of the things that you want to know more about and you want to learn from the other perspective. And then check yourself to see if you still want to advocate for the same point of view or not.

We had an awesome episode with Ami Vorish, CPO at Fair. and she is also extremely good at this and a huge advocate of starting with questions and understanding what she's missing. Totally. Well, the other thing I would say is the other motto that has really helped me drive impact, and I used the analogy of the bear. And I've always told myself, don't be afraid to poke the bear. And what that means is don't self-censor.

if you have a strong view after you've really grounded yourself in the truth and you feel like you've done your homework and you've asked all the questions, if you still disagree, if you still feel like we're going in the wrong direction, don't be afraid to poke the bear, no matter how hard things get. And that's a, it's interesting because I think a lot of, especially as an organization matures, you find yourself in meetings with many execs, founders, et cetera. It's often hard to voice your real opinion and usually like toned down a little bit, right? Because you're afraid of being the only one who disagrees or sounding stupid or things like that. And so I remember it was probably like 2014 or 2013 where I made a promise to myself, I'm going to always poke the bear

no matter how hard things get. Because at the end of the day, like, what's the worst thing that's going to happen? Like, did I get fired? Like, why would I even be afraid of that? But if I do, like, I'll find another kid, you know? Life is short. And so, So you've done this really well where I feel like you also always, I remember when we're working in the book, you've definitely poked a bear where you were like, you guys are wrong. Like this is how we have to approach it. And I've always really appreciate it. Thanks, man.

Is there an example of maybe working with Brian where you poked Brian and like, no? Yeah, absolutely. I mean, I've poked the bear many times. And by the way, I've been humbled many times. It's not like I poke the bear and I like rightfully poked the bear. Sometimes I learned stuff and I realize I was wrong. A couple examples that come to mind. One, I remember having these debates with all like basically senior leaders at Airbnb,

just about every couple of years, actually, around how much supplies should we have on the platform and what kind of supply should be on the platform. And there was one school of thought where we needed basically, that school of thought represented the view that we needed all supply out there to be on our platform, regardless of It was a person hosting. It was a vacation rental. It was a hotel. We just needed all supply on the platform, right?

I came at it from a very different perspective where I felt like that wasn't actually our mission from the very beginning. And although I understood that in the short term, the numbers probably would go up and you would get out and you would choose growth. But at the same time, like that wouldn't in the long run be a point of differentiation for us, right? And so I had a very different point of view. And it was very hard in that conversation. you know, everyone's excited. Everyone seems to be aligning around the point of view to be the voice that's like poking. And this is like, nope.

Let me, let me share why I think maybe we should go in a different direction. And it's when I remember like telling myself that I am here to surface and share information that will help the group make a decision. That's what gave me a peace of mind to actually like poke the bear and be able to, to surface the things the things that I've seen. I mean, the other thing is when we were working on the instant book, changed from request a book to instant book, right, for the entire marketplace, that was very challenging. And I remember getting up on stage in front of the entire company and explaining why,

like, this is actually good for humanity, like literally those words. Many people disagreed. And it was not an easy, it was not an easy thing to. do, but had to be done. And one thread that I've noticed across all these things that I noticed working with you is it's not like just making a case for something you can disagree with. It's showing the data that will convince them they are wrong or here's what they're missing.

It's not like a, it's not like a speech. It's a here's the data and asking them what data would you want to see to convince you this might be not as you think. Totally. I remember like doing Q&A with the whole company on the Instambuuk topic. This was a very long time ago, but I still remember where instead of, again, advocating for a point of view, I just asked all the people that were concerned, like, what their main questions were. And then we just tackled them one by one and we would talk. And it's, there's just something very disarming when you embrace the questions you embrace the negativity and you have an open mind that maybe there are some things that you missed and somethings that you didn't consider.

I love that. Okay. There's so many little nuggets already through this. that I just want to come back to and make sure people take away of how to be more successful. And this is not just as a product leader. This is just as a leader in any company. So the first is advice around thinking about impact above all else. And the very simple heuristic that I wrote down as you're talking is ask yourself, what are the priorities for the company? How can I impact these priorities?

And to do that, think about the levers that drive the business and where do I think I can make an impact to drive these priorities and drive the business. Two is inquiry first when you're trying, when you disagree with something or when you want to say no, start with understanding, asking questions, dialing up inquiry versus advocacy versus like, here's what I think. Poking the bear, which is really fun,

just like this idea of don't be afraid to disagree with someone in power. And your advice here is disagree with here's data you may not be aware of here. Have you seen this? Hey, check this out. Or what is it that would convince you? you're wrong. And then is there anything else I missed? Otherwise, we'll go on to more.

I think that's great. I mean, don't poke to bear for the sake of poking. Share, share the information that you think will be helpful to make it. Cool. Anything else? Any other things you've found to be really effective in helping you succeed? Oftentimes, it's about also like being able to be impactful at a company that is in hyperscale and is growing quickly.

A lot of it is actually just psychological. So it's not like there are these like core skills that, sure, like you've got to have some baseline skills, right? But a lot of it is day to day regulating your mind. And it's so easy to get lost in the sea of projects, the sea of priorities, the sea of opinions. And like I said before, dwell on the dependencies, right, that exist between teams without actually asking yourself, like, what you can do in the moment to make an impact. And for me, I've actually used two tools, which some of them you may remember, that have helped me. The first tool, this is against purely psychological, to help my mind. It's the serenity prayer.

So the serenity prayer grows something like this. Grant me the serenity to accept the things that I cannot change, the courage to change the things that I can, and the wisdom to know the difference. So I actually, that prayer was so powerful for me that I actually wrote it out on a piece of paper on post-it notes and I would read that thing like every other day. And it would help me just take a step back from the day to day and just like put into context what's actually important. And again, what is in my control today and the things that I can actually do?

So that highly recommend. did not know that. The other one, which you may remember, is the shit bucket. I do remember that. So the shit bucket was a visual analogy where I would take a piece of paper, and someone actually wasn't as visual. It was like real. I would take a piece of paper.

I would write down something that wasn't going well, perhaps a dependency, perhaps a project, perhaps a meeting that I was going to have that I knew it was going to be frustrated. Or maybe like we didn't even decide to go the way that I deeply felt. passionate about, right? I would write it down. I would crumble the piece of paper and I would throw it in my shit bucket, basically. And the rule was, once I threw something in the shit bucket, I couldn't take anything out of the shit bucket. So I would not dwell on the things that I just needed to let go. So this was a very powerful tool that, like, I'm a perfectionist. I just deeply care about many different things. And I have a hard time letting go. And so for me,

it was just a reminder that I need to let some things go and focus on the things that matter. And I actually remember even going into one of the ones with my direct where I would sometimes lead, like I could tell, you know, the PM is like a bit frustrated about how things are going. And one of my first questions would be, what are we throwing in the shit bucket? You know, it's actually like a very liberating thing that you can do. And did you have like a special trash can that was your shit bucket or is it the regular trash can? Every media group always had a trash can. I would always like throw stuff into the trash can whenever I got like upset about something.

It's like a different dimension trash can of bucket. Is there something you remember throwing the should bucket that would be an interesting example or story to share? I remember there was one person where I deeply wanted to hire who I felt was just phenomenal and would be such an amazing addition to the team. and I just I tried and tried and tried for a very long time and I just failed. I just could not get that person to join. And at some point it became like counterproductive. And I had to like let go and literally just like, wrote like, okay, getting this person into the company.

I'm like, this is not going to happen. I got to move on at this point. Just threw it in. I love these two pieces of advice. And it touches on how mentally challenging it is to be a leader out of hyper-growth company. Yeah. Is there anything you can share there

about just like that part of the world? Like people see your career like, holy shit, look at him. He's running Airbnb's business. What an amazing life. There's a lot of pain behind it. Is there anything there that would be useful to people you think? There's a lot there, you know? It's not like it was smooth sailing for me every single year.

Like I had plenty of challenges just personally, like going through that journey. Like you're not, you take a job and then you, you're sometimes just not prepared where it's going to take. And the reality is every three to six months, my job changed. So I would just get comfortable in the role I was in. Let's say like in the very early days, I was literally an icy growth PM with a tiny team. Got pretty comfortable.

And then like a year later, everything changed. And that was suddenly like leading a team of 20. Then a few years later, things changed again. I was leading a team with a couple of hundred. Then a few years later, again, everything changed. And you just, everything that you take comfort in in your current role breaks. The process breaks, how you hire breaks, how you spend your time breaks, the projects you work on, everything breaks. And you got to reinvent yourself.

And that is very hard to do. So one thing that I've learned is like you got to ask for help. Like you can't take some village, right? You can't just get there by yourself. And that's actually something that Brian taught me where, I mean, I mean, this guy just grew every six months. It was like a different person. And a lot of his like secret sauce is not being afraid to ask people for help who were experts in the thing that you're trying to learn.

I mean, my motto is like, ask for the impossible and sometimes you're going to be surprised. Like there are people out there that are experts on something who actually want to help you. That's awesome advice. Also the serenity prayer is so powerful. I did not know that about you. I want to spend time talking about things you've learned about scaling Airbnb in the org. But before we get to that, is there anything else that you think might be, that you think contributed to your success as a individually as a leader,

any other behaviors or mindsets? I mean, I think it's building teams and realizing that sometimes when you build the team, and this is actually often misunderstood, I think when people build teams, I think when people build teams, they try to make sure every person on the team is good at just about everything. You typically go through the process

of like, here are my strengths, here are my development areas. And typically the development areas are like, you basically develop, you try to develop just about every single thing so that you can be good at almost every single skill that exists, right? And I just think that's the wrong mindset.

Instead, what I've learned over time is, Instead of trying to find people that are good at everything, you need to look for people who spike on specific things and then add them to a team with different spikes. So there's no single person that is like spikes on absolutely everything. That's very rare. But they spike on something that's very crucial to the team.

And if you assemble different spikes on a given team, that team is going to do great things. As long as everybody inquires and everybody starts asking, question actually listens to other people versus just, you know, coming about that. So even now, like as an investor, when I look for, when I talk to founders, the first question, like, in my head is, like, what is this founder spike on? And how is that spike relevant to the problem that they're tackling today? And how well does this founder hire to bring other spikes to the team? Like, that's literally like what I think about these days. What are some examples of spikes just to make it even

more real, like things that people might be good at as like strategy, influence. What are some things you commonly see that are spike skills? Yeah, I mean, I think there's the very natural spike sometimes is you get a domain expert. So there's a specific field. Well, let's take marketplaces. And there is someone who just understands the mechanics of how things work and is eight and just really spikes on understanding how you can take certain drivers, what you can do with those drivers and how you translate those drivers to measurable result. There are people who spike on on sales and who spike on like just being able to package something in a way that other people cannot package it. There are people who spike in process. Like there are people who will literally

every day think about how to get people to work together really well. And that is like they just know how to get to the essence of that, how to connect the dots between different teams, working together. Some people are really great at product design. I've seen quite a few founders actually who can tell you immediately about what kind of interface is going to resonate with people and what kind of won't and why. So there's just some examples, but there are many dimensions here. Awesome. Okay. As the last question along these lines, I'm going to share a few other skills that I noticed you're incredibly good at. And how about just pick one that resonates with you and share some thoughts and how to get better at that and why that's important.

One is influence. You're an incredibly strong influencer. You get a lot of stuff done that I think people will be like, how did you do that? I have no idea what he just did. Another is you're very good at keeping a very high bar. That's one of the things I learned from you is just the importance of keeping a very high bar and spending more time on stuff. That's something I remember from me.

Just like spend a little more time on this dock, make it a little bit better, refining it a little bit more. So that's to you. Another is just getting stuff done and focus. while also avoiding the limelight. You're not like, you try to not be in front and center. Like you haven't done any other podcasts. I don't think you've written a medium post. I don't know if you've tweeted.

Like you try to just get stuff done behind the scenes and not, not be, not get attention from everyone. So maybe those are a few. Is there one of those? Do you want to spend all the time on? Yeah, I mean, first of all,

thank you for saying that. Some of those resonate for sure. I think the getting stuff done and being hyper-focused on the drop is something that's really important. I mean, at index here, we also say, keep the main thing, the main thing. And just like in investing, same thing in operating, you know.

You got to focus on the actual job versus like all the other things that you could potentially be doing. So to me, I remember when I was actually hiring product leaders, and there's some product leaders would do lots of different engagements outside of the company, whether it's investing, advising, speaking, attending, confidence, all those things. And they were huge red flags to me because it was clear that this person, there was just something missing in their day-to-day. They didn't try to put them like all of them into the thing that they were doing. And so for me, like, it's really important when I hired people to hire people who were

incredibly mission-driven and would dedicate every ounce of energy to keeping the main think of the main thing. Yeah. I talk about this on Twitter and LinkedIn, this idea that people see people like me and other PMs, sharing wisdom, and they're like, oh, these are the best PMs. They know so much. But in reality, the best folks, you as an example, like, I spend zero time on Twitter or LinkedIn.

They're just doing the job trying to show great impact, try to make a business successful, trying to build great products. And I think it's important to remember you don't need to be tweeting and writing medium articles. Yeah, I mean, I think there are, you know, people who find jobs. joy in solving hard problems. And like the joy you get from working on the hard problem is fulfilling. And you don't need to seek like external validation for for the things you do every single day, you know? So yeah, I love hiring people like that. Let me zoom out a little bit.

So we've been talking a lot about the skills that you built and the mindset that you built to be successful individually. But also you managed large teams. You helped scale Airbnb be massively through hypergrowth. And there's a few skills I noticed you're really good at that specifically applied to scaling an org, building an org, building teams and things like that. And so I want to spend a little time there. You touched on this one a little bit, but I think there's more here around setting priorities. You're incredibly good at setting priorities, making sure everyone's aligned, making sure the main thing is the main thing. You just talk about what else you've seen be important here as a leader of a larger growing org around setting priorities.

I have a lot of strong opinions here with setting priorities. I would say the first one is, and this was my motto for the longest time and this still is, you got to let fires burn. And what that means is you can do it all. Like you just need to let go of things that are not important. Because if you have 20 different things that you're equally engaged on, it just means you don't actually know what is most important. And so my motto has always been let fires burn.

You've got to be okay. with some things not going well so that you can dedicate most of your energy on the few things that actually matter and the things that are most important. And it's hard to do. It doesn't feel good. Again, many people, especially PMs, are perfectionists. And so it like, it just, it hurts when things aren't going well and you just got to learn how to let things go. What I always did was I kicked off every Monday with the leadership meeting where we would

talk about our priorities for the week. We would not talk about longer-term priorities. It was literally like, for this week, what are we trying to get done? It could only be one, two, three things. And we would jointly agree on the fires that we would let burn. And so then when, like, my partner, my engineering counterpart or my design counterpart would, like, see a fire burning, they would know, like, yep, we agreed that we're going to keep letting the fire burn for now.

And it was just really important to be aligned as a team on that. Now, the other thing that I've learned is you got to let other people burn fires too. And it's very actually empowering. And oftentimes I remember, especially when you're leading a very large organization, there could be teams and teams and many different leaders who you're working with. Oftentimes people come to you and are basically like, we got to do this new thing to drive goal one. And I just don't have enough resources.

and we need to hire more people and we need to expand the resources of this team. My first question always was, well, what are your actual priorities and what can we let burn? Meaning, do you actually have to expand and do more things or can we maybe reprioritize certain things and focus on fewer things and put a lot more energy behind?

You know, but to have those conversations, as a leader, you also have to recognize that people on your your team are eventually in a really good position to gauge what fires should be burning and which are not to be burning. Now, the one thing I'll say, though, is with this, it could be dangerous. And there are some things that you should never let burn because if you let them burn for too long, bad stuff's going to happen, right? So I have a few of those examples for me that I have, like over the years learned to not

let burn. First, timelines, major timelines. is like huge product launches. Once timelines slip, you basically establish precedent that timelines are not as important and timelines can always slip. So you never want to set the precedent that timeline slip. So that to me was when there was a major project on timeline was significant slipping, I'd never let that fire burn. You immediately jump in. The second is when there is disagreement on a strategic decision or maybe even part of the vision. If you feel like that exists, like, for example, if not everybody, like, buys into Instant Book or, like, there's just some disagreement about what supply should be on the platform, you've got to squash that immediately. You cannot let that fire burn because it can spread. I guess if I follow the analogy, like, it can become a wildfire. And then suddenly, you have a team of people who are, who don't believe in what they're doing. They're losing meaning. They lose meaning in their work, right? Which is just really bad.

So you have to bring people together immediately when you feel like people, whether it's many or a few people, do not believe in the direction that the company's headed. You got to squash that immediately. Then the third one for me, and this was a bit painful to learn, but you never let a senior hire process burn. meaning like you will always and this is what I felt during my 10 years at Airbnb I always felt underwater and I always felt like we just needed to bring on more people who had experience and certain things that we were doing and anytime I delayed or I was like not fully engaged with a hiring process especially a very senior person it just it bit me for such a long time and it set the whole team back.

And so those are the three things that I would never let burn, but you've got to let a whole bunch of other stuff burn for sure. Such counterintuitive and amazing advice. You shared a bunch of examples of things that you don't want to let burn. Are there any examples you could share

of things you let burn, things that would surprise people or a story that comes to mind of like, yeah, that's fine. You know, sometimes you would have examples where certain products, product launches didn't go well. And let's say it just, you know, you weren't seeing in the numbers, the users weren't happy.

Like, okay, that's sometimes you just need more time to understand what's actually wrong. You don't need to like jump on it immediately, right? So that's maybe like one example of a fire that I led burn quite a bit. And quite frankly, at some point, I had so many teams that I was working with that I just needed to prioritize even between the teams. where like this team is the number one priority. And I know that I need to be in desire reviews with with this other team. I just, I can't because I have to be thoughtful about how I'm spending my time in this given moment.

And so I actually have to deprioritize project. And so there are certain projects that were important, but I led Byrne for a while because I just had to spend my energy elsewhere, you know? And then, of course, I would, to myself, I was thinking, like, are we doing too many things? Like, is this the right way to offer? I think this is really useful for someone that say, isn't ICPM on a team that's wondering, why the hell our team is just wasting our time? We're building all this stuff.

It's not working. Why isn't anyone doing anything? Why aren't they giving some resources? Why aren't they repurgizing? It's because they know there's many other problems they're dealing with and they're letting this burn for help. Yeah. And this was actually alerting for me in an area where I would say I failed over time is just general communication to the broader organization. When you rise really quickly, you tend to underappreciate

or I did just how important it is to communicate what as a leader you're spending your time on and the areas that you think are the highest priority right now. And so eventually I started doing a lot of old hands and I started sending like the weekly thoughts from Vlad or just like my random musings on what's in my head. And I realized that sharing that context with people are just so important. People actually want to hear from you. And it's good to over communicate and it can help people understand certain things about their day to day. I know that it didn't come naturally to you. I mentioned that you kind of like to be behind the scenes under the radar, not in the limelight. So I could see why that wasn't something you were

doing initially. Is there anything more? You can show there about what you've learned, what you learned about why that's important. Like, why are people, why spend time there? What happens if you don't? Everybody wants to find meaning in their work. And everybody, typically wants to understand the reasons behind a decision. And it's important to share, to take, like, I've done this myself where I just like make a decision and you're like move on and you go on to the next decision. And it's actually so, so helpful if you take like 10% more energy and time to now bring everyone along around why a certain thing was decided. because it's going to help them just themselves make better decisions because now they have a lot more context about how this decision was made

and they can learn from that moment. So that's partly why it's important. I mean, for me, it didn't come naturally to me. I'm like a pretty, I don't know, I'm a deep introvert. Like I shy away from many different things and it had to be a learned thing. I think you're also a really good example of something I talk about here and there is you can be really successful in very different ways. I'm also introverted.

I think we're similar on the spectrum of colors or what the thing of personality test. And you've been really successful. You could also be incredibly successful as a very extroverted person or someone that's very analytical. And I think you're a great example of someone that's less, that's more reserved and doesn't want to and is introverted, as you said. And I think it's important to people to know you can be incredibly successful as a PM as a huge leader. Totally. From that place. This episode is brought to.

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That's get EPPO.com slash Lenny. Okay, so just to summarize the lesson we just talked about mostly is let fires burn. Basically don't feel like you need to solve every problem as you rise in the ranks. And I think this applies even if you're not the top of the org, even if you're manager of managers, even if you're manager of nobody. Yeah, maybe the other thing I'll mention, and like as I reflect on setting priorities and just like working.

I think a big lesson for me is that chaos is good. Chaos is actually great. And sometimes you want to create chaos in an organization to push the organization to think creatively and to actually make leaps in product development. And so, I mean, I kind of, you know, as I reflect on my life, I like cleaning up messes. I like when things are very organized.

I liked when there's just like very, there's a lot of clarity on how things are put together, right? And it's very, chaos is scary, right? And I think that this is very natural for a lot of people for chaos to be scary. But I've seen examples when just a bit of chaos is so, so helpful. Just to give you an example, I remember me talking to Brian one day. And he was like, hey, I just don't feel good. Like something just feels off right now. And I remember asking him, like, what do you mean? Like, our numbers are up into the right. Like, we're shipping quickly. Everything's

great. What do you mean? Like, what are you going to happy with? And his response was, was things are just too calm. I don't like it. And I was like, okay, what do you mean? Like, calm is great, right? Like, I operate in calm. And he then picked a project that he thought was important. I think it was actually host onboarding at the time.

And of course, in this project, we had like three or four. I remember we had this like perfectly crafted timeline. We're going to design this for the next four weeks. and then we're going to start building and we're going to deploy in certain pockets of users, we're going to learn, we're going to iterate, etc. Very rational timeline, right? And he said, yeah, I don't care about any of that.

We're going to design this in 24 hours. And that was just like, mind blown, right? Like, one, how, two, the ripples that's going to send through the organization because I knew all the people that were involved on building this and we had like this a whole like neat flow. And we did design it actually in 24 hours. It took a little bit longer, but we just ended very quickly.

And what I learned in that moment is that the chaos that was actually an example of chaos that he inserted into like this very calm building process. And that chaos forced us with that artificial time constraint to dial up our intuition and to think a bit more creative. than maybe we would have in the past. Now, that didn't always work, because there were examples of this where you were just like,

I don't know what the answer is. Like, I need more time to design this and to think about this problem, right? There were definitely examples of that, but there were many examples where it was actually a great forcing function to go with your God and actually, like, innovate. That's an amazing story.

And it reminds me of something else, just to take a quick tangent here is, Brian's incredible and just asking people always, okay, that's a great goal. you have there, what would it take to 10x that goal? Yeah. He like gets to the FP&A projection. He's like, great, okay, how do we 10x this?

And I found that to be really scary, but also really effective in helping people think a lot bigger. Is there something there you can share about just what you learn for Brian about thinking that big? I think it's less about hitting the goal. I think a lot of people, when they see really big goals, they get, they immediately, like, afraid of the goals because they think, oh, my God, I don't know how to hit this. if we don't hit it, what happens? And you start thinking about all the downstream consequences. The reality is it's not about hitting the goal. It's about thinking how to hit the goal and going through the journey of that creative journey of like,

what does the world need to look like for this to be true, this like crazy goal to be true? Like how should we think about it? And oftentimes it pushes you to test extremes, right? The whole world is going to operate this way or nobody in the world is going to operate this way, versus something in between. And usually it's when you start testing the extremes and you begin to like realize like, oh, you know, this is the path

that we should actually take. Yeah, I found exactly the same thing. Just thinking from backwards from, what is it the best possible thing we could do versus incrementally forward ends up unlocking a lot of big ideas. Something I imagine is in people's minds as they hear some of the stuff like designing something in 24 hours or thinking 10x bigger is like,

I don't want to work that way. That sounds incredibly stressful. that sounds like, I don't want to, why don't, that sounds really hard. You mentioned this that this isn't necessarily for everyone, not everyone needs to work at this company or work this way. Part of it is hiring is finding people that want to lean in to work really hard. Other people don't. Is there anything there just like, this is actually really hard and it's not for everyone,

but it's also ends up being successful and you end up having a good time, a lot of times afterwards? I find that those sprints where like designed this in 24 hours, were brought a lot of connection to the team, actually. And they were like my most fun moments, actually. Because you kind of like, you're forced to let go a lot of constraints. All these like organizational dependencies disappear, all like the stuff that's kind of noise,

and you can just start building. Right. So for me, especially when you're not doing this by yourself and you're doing this with a team of people, it was deeply rewarding because you were all working together. just like shooting the shit and like throwing a whole bunch of ideas out there no idea was like too crazy right now it's not for everybody and so i actually in the interview process when i would hire pms i was always not always in the early days i guess i had to learn this but in the later days

i always set expectations about how we work and so i think some leaders do this it's like the anti-sell cell where I will share the worst day or what I think you will think as a candidate, what the worst day would be at Airbnb, and then still ask you if you want to join the team. And I would basically tell people, we're going to work day and night. We're going to work weekends. Direction is going to change. The strategy, like out the window every three months. The projects you're working on today, we're going to kill three weeks later. The roadmap that you are right now auditing as you're deciding your offer, when you actually join after you took some break from a little job,

is going to completely change. And so getting people, I think the common thread there is, everything is changing all the time. You've got to be cool with that if you want to join this scene. And totally fine, like, if that's not for you. I love that. It makes me think of something when a colleague used to say to Riembis, if you haven't changed teams or your desk in six months, something's about to happen. Something's about to change. Totally. This unsell idea, there's a recent podcast episode where someone did something similar. You call it the unselled email where he sends the candidate, here's all the thing,

based on all the things you heard from the candidate during the interview process, here's all the things you probably won't love about working here. And the recruiter was always really mad at him for like, don't send that. My numbers are really going down because of this email, but long term it ends up being really successful for them. Yeah, I mean, you're going to probably hire fewer people that way,

but you will hire the right people. So I think then you're going to actually have a team that you can rely on for years and years and years as things change. Yeah, just have to align incentives of recruiting on that. Okay, so one other area I wanted to spend time on is basically org design and hiring and people. So you were very good at building really effective teams, prioritizing them, bringing in amazing talent. What can you share about things you've learned about as a company is growing and org is scaling about org design hiring?

Yeah. So for me, like one of the hardest things about building teams and going through hypergrowth was the fact that you're going to lose a lot of friends on that jury. You just have to be prepared to say goodbye to your friend. Meaning, when you start, you build really deep relationships with people, like when you're a smaller startup, right? Like you typically have one-on-one interaction

and you know everybody, right? And you have that connection with people. And the reality is most people, if the company is truly going through hypergrowth, most people are not going to scale. It is very rare for somebody to scale with the company. And I mean, we actually, so at index, we wrote a book, Scaling Through Chaos.

And there's this crazy stat where basically when you look at many, many companies that reached a thousand people and were successful, when you look back to the first 10 employees, you realize that only two to three of those 10 first employees stayed with the company when the company reached 1,000 people. right and that's just so like indicative of what will actually happen in practice like there are certain skills that you have that are good for in the specific domain for a period of time and that time is not like universal forever right like at some point everybody taps out and so it's just having that realization is it's tough it's tough emotionally it was like one of the hardest things for me like as a leader and i would say the way to break out of that is to ask for help and to try to learn as much as you can about what the next role for you is going to look like so that's one thing that i've learned i would say another thing is that

all org charts suck. There is no good org chart. Every single org chart has problems. So you can be organized around business units. You can be functionally organized. You can be organized our own problems. And the reality is, like, every single one of those constructs sucks. Right?

There are pros and cons to each approach. Like if you organize yourself into business units, the problem you typically run into is silos. when people start basically advocating for their business unit with little regard for other business units, right? If you're functionally organized, sometimes you create too many dependencies across the organization and it becomes this like matrix way of working, which could be challenging. And as a result, could be slower to ship product, right? Those are just examples. These are not universal issues, but those are examples where regardless of where you organized, there are going to be problems.

So for me, one learning was if you're having a problem and you're trying to solve this problem, reorganizing and like a new org chart is rarely the solution. It's not about the boxes and how you configure the boxes, right? It's about the people in those boxes. And it's about how those people work together. Because you just need to understand the cons of working a certain way. And then how do you design a process around your work structure to make sure. that people connect and work really well together.

So my advice there also to founders who I talk to now, focus a lot less energy in the actual org design, study the different types and just pick one. And once you pick one, focus on the people, the culture, and how people work together. That's really interesting. So basically you think people are overthinking org design. Yes.

How do you think about incentives and goals and how that kind of impacts all that stuff? Because there's people and then there's like, here's your goal, here's how you're measured. And that's what they're going to work on in this thought. I mean, I think incentives come down to culture. And it's what you set as like the fiber of your organization. So again, like I think you can align incentives and people will be excited to make

impact on the organization, regardless of how an organization is actually organized. That's a really interesting takeaway because I think a lot of people think about, okay, if we just org this and put this person here and create business units, things are going to start moving. And you're not saying don't think about that and don't necessarily do that, but you're probably putting too much weight on that, actually solving your problems. Yeah, I mean, I think you want to certainly study different ways of organizing and the pros and cons, but just know that no matter which choice you make, it's going to suck and there are going to be organizational problems, right?

And you just need to go into it with wide open eyes and then create process to make sure that whatever the cons are, if people are in silos, well, then you've got to have a really good way of bringing people together and creating the right incentives to make sure people collaborate, right? So there's all these other things

that I would say are much more important to folks your energy on. Awesome. Anything else along these lines around org design or hiring that you think is really important or has been effective.

You know, the one thing that is universal for me and always has been is mission over domain expertise. basically mission over domain expertise, mission over skills. I think that if you have like a raw, like that raw horsepower and you're deeply, like you just love the mission so much, you can build whatever skills are necessary for the job. And so I actually love taking, like, as an operator, I've loved taking bets on people who are maybe earlier in their career,

who have energy, who have drive and who are a deep, thoughtful and deeply resonating with the mission that we're working on. Because at the end of the day, like strategy changes, work change, teams change. Everything changes all the time. And the one constant, I think, is actually the mission. And when shit gets really, really hard, when your company almost collapses like we did during COVID, the thing that gets you through those hard times is the mission. If you don't have mission, you don't believe in the mission.

you lose meaning in your day to day and you start to disengage from the company. So I think that's actually the most important thing. So what I'm hearing there is potentially, if you're just like hitting it at your job, or you think it's just not going anywhere, it might be that you don't actually care that much about what the company's trying to do in the mission

and maybe there's not a lot that can change for you to actually be happy there because you don't actually care. Yeah. Fascinating. Something that I wanted to come back to real quick, a lot of your advice comes back to impact, like impact above all else, drive impact, focus comes back to what is the most important thing to do.

Something that I think about a lot is how do you be successful within a company and one of the levers is go to a place and a team that is driving impact. Do you have any advice there around just like where you are best suited to be successful within an org kind of coming at it from or impact is most happening? I mean, I always thought about it as like the combination or almost, like this Venn diagram of like there there's one circle which is like all the different priorities that are important. Then the other circle are your friends and where you spike. And the intersection of the two is the place where you should be. Right. And sometimes you're not quite there at the intersection and you're kind of gravitating towards that intersection. You're building a specific skill that you're already like naturally like pretty decent at, but you definitely want to double down on it. As you're

learning more about the priorities and there's a match there. The worst thing I think you can do is just like sit in a job where you're not being impactful. You're not working on the top priority and like you're just kind of wasting your life. You know, like our time is short on earth. Like you might as well wake up every day and work in the hardest thing you can where you can truly based on who you are and the spikes you have make a dent and whatever is going to happen, right? And also I have the Serenity prayer ready to go when things get really hard. Yeah. Okay. So, So what I want to do right now is summarize many of the things that you've shared before we get to talking about Airbnb today and Brighton Chesky's approach to product. I guess before I try to summarize stuff, is there anything else you think is important skill-wise or behavior-wise that we have in tension?

No, I think we've done a lot. Okay, cool. So I'm going to just, this is like almost a Vlad's guide to being a successful product leader. I don't have it all summarized here yet. There's have a bunch of notes, but I thought it would be fun just to try. So one is, and the way I would think about this as you're listening to this is how do I be more. what can I do to be more successful as a leader in a company? And this is all kinds of stuff that I 100% agree with is effective.

So one is impact above all else. Think about what is the company prioritizing? What is important to the business? How can I drive impact there? And to do that, think about the levers in the business that move that and then find ways to work on those things. This idea of inquiry first when you disagree with something, shift your mindset to asking questions.

And then along those lines, kind of, when you disagree, this idea of poking the bear, sharing, here's why this might not be right. Here's why you might be wrong about this. Here's data that I found, or what data wouldn't help you understand. Maybe you're wrong here. Okay, what else? Saying no.

Being really good at saying no. And this comes back to impact and focus. Lit fires burn. Really powerful idea. Don't feel like everything has to be solved. I'm similar to you where I feel like anything's in order and clean and organized And so this would be very hard for me. But such a powerful lesson of just, it's okay if things aren't going great.

And I love your advice of align with your team on, we will let these things burn for now. Anything you want to add, by the way, as I'm going through this? No, got to let everyone be a paromaniac, at least to great things. Awesome. So along those lines, embrace chaos. Let things be chaotic sometimes because some of the best things come out of that. And as you shared, Brian, sometimes just introduces a little chaos to get people out of their safe world a little bit.

This idea of a shit bucket, if things are just like, I hate this thing and it's not going well, I'm just going to throw it in the shit bucket for now. And that's just how it's going to be and I'm going to move on. So I could focus on impact and important things. Amazing. Okay, what else do we have here? So many little notes here. Be prepared.

So as you're organizing teams, be prepared to lose friends that you had at the company as you rise and as you have to do things that maybe they're not lined with or happy about that aren't helping their career. All org charts suck. Nothing's going to be amazing. Don't overfocus on the org chart, focus on the people and the culture. Oh, yeah, the mission above all else.

Just like if things are not going well, it might be people aren't aligned with the mission in the company. Yeah. Okay. Is there anything else off top of the way? It's so interesting. Like, when I think back to my 10 years, like things that I actually remember the most

are these moments with other people and not the, some project or some product launch that's like going super well or you know us do really well with metrics it was the things that really made i think Airbnb special and i really now that i think back to to those 10 years in my experience i deeply just resonate with are those little moments and like one example and this is why culture is just so important because these things don't just happen like organically like you have to be thoughtful about building culture and And then I think you create a place where these little things can happen.

So for me, I don't know if you remember your experience when you first joined the company, my most memorable experience at every of me is the human tunnel. And it was just this thing where I remember it was my first day and I was standing behind like this giant wall and there was silence in, I think it was a cafeteria. I was like this huge huge room, right? And then somebody like this engineer runs up to me and says, hey, go around. to the other side of the wall. And I turn and suddenly the room just explodes in cheering and clapping and everyone yelling my name and everyone is like basically doing a human tunnel with their hands.

Literally every single person at the company at HQ, including the founders. And then I run through under everyone's cheering and I jump into this beanbag while everyone's like chanting my name. That was my first day. And here I am like, I don't know, 12 years later, 13 years later, I still remember that as one of the most amazing moments of the entire journey. And I immediately felt accepted. And I wanted to contribute to the team, you know? And a lot of the reasons why there were many moments like that throughout my 10 years. And it was a result of how we hired people for certain core values and were very intentional

about just helping people integrate into this crazy company that was growing super fast. That was an amazing story. I feel exactly the same way. I went through a similar experience when I joined. And obviously, the human tunnel eventually didn't scale, and people started doing it like per team

versus the entire company. We could do a whole episode on Airbnb culture and learnings from that. Interestingly, with the human tunnel, it's like, it started, I think,

with the founders, but it ended up being, they had no involvement in these tunnels. Like, it was just employees knew that this is the thing we're going to do for every new employee.

and so I think it's interesting. I guess just spending a little time on culture and learnings from Airbnb about the value and power of culture. Is there anything there you take away with two other companies you work with now of just like how to set up a great culture, how to do this well? I would say there's no like single playbook. I would say the one thing that comes to mind is being really intentional and thoughtful about it and actually dedicating energy to it.

Just as much as you spend time building product, hiring people is you got to spend just as much energy actually thinking about culture and your core values. And so core values are very, I would say, indicative of what the culture will be. So those two are very linked, right? And once you have, once you think about core values, I remember what worked really well was you don't just like write your core values in the document somewhere and then no one never opens it. You need to, the key is, regardless of what the core values are, you want to make sure that

those core values are prominent in just about every single. thing that you do, right? So when you hire people, you hire for certain core values. And at Airbnb, we had core value interviewers up until, I mean, my entire tenure, basically, even when we had thousands of people already at the company when we were hiring people, everybody had to pass core values interviews. So it was very ingrained in how we hired and what we looked for. Then, even performance reviews and promotions, no matter how much impact you made, right, no matter what you did, if you were not also exemplifying core values, you didn't get promoted, right? You didn't get to the next level. And so even in our performance conversations, those core values were very

present in the day to day. And then, of course, they were also printed everywhere. They were just like physically everywhere all the time. So like I felt like every single person around me always knew what the core values were. And so that's my biggest advice. It's like, don't copy some other company's core values. Instead, just be intentional. what matters to your organization and then make sure that those core values are freaking everywhere part of every single process.

Otherwise, no one's going to care. Just to reinforce what you're saying, have been gone from Airbnb for five, six years now, and I still 100% remember the core values. I'll go through them real quick. Be a host, be a serial entrepreneur, which is serial as in the serial, the story of Airbnb championed the mission.

Simplify. simplify, although they tweak that one or they cut it, right? And then embrace the adventure. Embrace the adventure is my favorite. I love that one the most. See, years later, like, you still remember. Exactly. Every frame matters was the other one.

They decided to cut out because they realized something they learned about of core values that I thought is really interesting is they shouldn't be aspirational. They should be who you actually are. And so there's a period where the founders are like, we're not actually amazing at this thing. So let's just remove it from the core values and reduce the ones we're focused on. Yeah. What I also really liked is that there were tangible, like, examples always about what it meant to embody this core value in your day-to-day work, right? And so then it was like very tangible for people versus just some overarching, like embrace the adventure. Like, what does

that actually mean? Right. Right. And then just to make sure people get this point you made about this core value hiring team, which is really unique. I don't know if anyone else does this, is there's people trained to interview in core values. And they were like a specific volunteer team. And that part of the interview process, one of these people came in and they interviewed for core values, which was meant to represent what the founders were looking for initially. I mean, it was also very telling how I remember it was an honor internally to be selected to be a core values interviewer in the first place. Like most people at large companies are like, I don't want to do any more interviewing.

Oh my God, like me interviews all the time. Here, people were like, it was a sense of like this emotional proud moment when you were basically given the keys and you were, somebody said, hey, like, we actually think you would be fantastic at helping us think about how to make sure every single new hire embodies these core values. I think that was so powerful. Amazing. Okay.

So, again, we could spend an entire hour in the culture of Airbnb and all things we've learned there. It's actually a good segue to the last area, the last part I want to talk about, which I think a lot of people are probably wondering about as we have been chatting, which is about Airbnb's current ways of working. So we had Brian Chesky in the podcast, the most popular episode of the podcast, the podcast turns out. And he shared his approach to product, which a lot of people are like, huh, that's unique and different. And I don't necessarily want to work that way. Other people are

like, this is amazing. This is exactly how I want to operate. And so I'm going to meet my company work this way. The way he described Airbnb is it kind of moved from bottom up, experimentation driven to very top down. We're going to have one roadmap. I'm going to be involved in everything. Product managers are now product marketing managers and all these things that I think people are like, wow, That's really new and interesting. You actually worked through a lot of that. You went through that transition. I think technically you're a product marketing manager when you left Airbnb.

Okay. So you're a really good example that you reported to Brian during this time. Thoughts now that you're removed from Airbnb on that way of working, pros and cons, right for everyone. Maybe not right for everyone. How do you think about this stuff? Yeah. So first, I guess let me zoom out of like from Airbnb for a second. And then we'll go into the concrete details of what Brian said.

I don't think you should copy another company's ways of working. The reality is it is how a company operates is so unique to the founders, to the leadership team, to all the employees and the domain potentially, the moment in time, because how companies operate also evolve sometimes over time and just certain different ways of operating might be needed. So I wouldn't just copy someone else's way of operating. Even at Airbnb, it was just very interesting.

For us, it took us a long time to figure out how to operate, right? And we were actually, we did it for a long time, explain and give clarity to people of how we should even operate in the first place. Because so we hire people from Facebook and Amazon and Google and like Netflix, like every Apple, like every company. And every person would come in with their own preconceived notions of how they wanted to work. And oftentimes those opinions differed. And so because we never actually stated like the Airbnb way for a very long time, sometimes it would be chaotic, right? People would just wouldn't know how to operate.

And then you go from team to team, teams would just operate very, very differently. And that was a problem. So I think here the lesson for me was not necessarily. there is one way to like every company should operate like this way and it's much more about picking an explicit way to operate and then voicing it to every single person so that everyone has clarity and how to do their job. I think the worst thing is like people just don't have clarity on how to do things day to day. They don't know how to drive impact and they're just like, what am I doing with my life? You know? So that was kind of one lesson.

Now specifically like going double clicking into Airbnb and like where we moved. So I think one of the things that Brian mentioned was being top down, right? I actually think top down is this construct that has negative connotations associated with quite a bit. And it's often, at least in the context of Airbnb, I think misunderstood. So what people think top down, and I've had many, by the way, many of these conversations with folks, right? So most people think, oh, there's a leader here in an ivory tower sitting somewhere. It's divorced from the team making a whole bunch of this event, right?

And everyone else is like powerless and can't do anything. That's not actually a reality, right, of top down. Now, in that room where we made many of the hard decisions with Brian, the reality was he asked a shit ton of questions, right? Again, he didn't advocate in the beginning. He would come in with tons and tons of questions and he would listen. And of course, sometimes, like, he would disregard certain things that he heard because he had very strong conviction in a different direction, but he listened.

And oftentimes, he would also change his mind, right? And so as a leader, like at Airbnb for so long, I never felt like I wasn't listened to or like he was just making these random decisions. I always had an ability to influence and an ability to voice where I felt like the company should go. So, like, yes, he made a lot of decisions, but he made sure he was informed in those decisions. And then many of us were contributing to all the information he needed to make a decision, which is then also why, he wanted every leader to be in the details. Why did he like stress that for himself and every single leader in the team? It's because when you get into that room, right,

and you start discussing many different directions you can go, if the leaders in that room can't tell you what's actually happening with the business and why are they there in the first place, right? Like you can then make a good decision with that group of people. So then suddenly like your team of like 10, you have to blow up to a team of 30. And if those people are not in the details, then you got to, like, what, bring in like 50 people?

And so at some point, you need to make sure that leadership is actually in the details, understand what's happening, and can help bring to light information that's going to help somebody make the right decision, right? So that's why, like, top down and being in the details, to me, they were actually very connected, and they made a whole lot of sense.

Now, the one thing I'll say is, like, at some point, when you're working on, on many things. It is challenging to be in all the detail, right? And if you mandate that product cannot ship without, like, certain people being in every single detail, sometimes you could slow it down, right? And that could be a con of that way of working. I would argue for us at Airbnb, the quality of what we were releasing kind of suffered

because we were just push, push, push, ship, ship. and people were shipping across the board. And I did feel as a leader, like I wasn't proud of some of the things we were shipping. And so I appreciated the intentional slowdown at the expense of our goals to get to a higher quality bar and then amp up velocity again

after everyone had a better understanding what quality actually was. So we kind of had to slow down for a bit to then speed up later. And I think a lot of it is, Brian always wanted to make sure that every leader would be able to make decisions and have really good judgment. And he wanted to teach what that meant. And I actually really appreciated that over the years.

Now, you know, like if you were to go back to semantics and say, hey, we top down, bottom up, those are just semantics? Like, I would say we were actually, like, if you really think about it, we were neither. because bottom up you could always through certain channels voice information again if you didn't self-centered and you were not afraid to poke the bear you had an ability to voice information so from that sense

there's lots of information that came bottom up but then at the same time there was also like a lot of conviction and intuition and context that came top down and because for a lot of these decisions there was so much conversation the reality is I think the way we operate was actually somewhere more towards the middle

on a day-to-day basis which is why for me, like, I thought it was great. We had a boss on the podcast, CTO of META. And I always thought of META is a very bottom-up organization where anyone can run experiments. They're shipping things all the time. He's like, no, we're very top-down. We tell people, here's the things we're building this year. Here's our big bets.

Here's what we're going to prioritize. And so I think, to your point, a lot of people don't necessarily understand what that means and see things as bottom-up versus top-down. Any other pros and cons just real quick on working this way? I think a lot of people or a lot of founders are like, maybe I should move my company this way. Maybe I should just be involved in everything. Maybe we need to move PMs to product marketing managers.

Is there anything else that's maybe a pro or a con in this approach that might be worth sharing? Yeah, I mean, I think what you need to recognize, right, is which decisions and what part of the company do you have special, like, do you spike on and where you have edge and where you can help make the best decision? And then I would argue then as a leader, then it is your job to be involved in those decisions, right? For Brian, he always spiked in product, in design and marketing, right? So it was very natural. This is why he was basically the CPO, right? That's why he was in all those decisions because those were his spikes. And that's where he helped everybody move forward in a certain direction.

I think for founders, like you just need to recognize, like, what do you spike on? What are the specific things that you have this great insight that other people do not and immerse yourself in a lot of those decisions, right? And there are some things that you might need to let go of, right, that or maybe like not as important or maybe certain things that like you just, you won't add much to the conversation and you have someone who you trust who's going to uphold like a certain quality bar or whatever, whatever. So it's just being thoughtful about where you spend your time and leverage leverage your strengths, basically. Final question along these lines, very specifically around this whole product marketing manager move. To me, it feels like mostly like a rebrand of PM with some marketing work. And in my eyes, PMs already should be doing marketing and thinking about adoption and growth and all these things. And so I'm curious just your take.

Do you think this is like with the future for PMs in general? You think this is just like a funny thing that Airbnb is trying and it doesn't really make a big down to thoughts on just this idea of PMs should be product marketing managers and we don't need PMs as PMs. I kind of felt like that was reading about this in the news when it when it blew up. I mean, it felt a little overblown to me, to be honest. Like just like you said, a lot of PMs at the company were thinking about how. how to talk to users about the products they were shipping. And they were basically marketers to some degree, right? So I would say the rebranding of product manager,

it did do some important things like shed project management and establish an entire function that focused on making sure things are moving in the right direction from a project perspective. And it highlighted the importance of marketing. Or maybe just it wasn't as highlighted before, but it was already happening at the company. So, you know, for a lot of the product leaders out of the company, it was very liberating because now you actually don't need to worry as much about, let's say, timelines and coordinating

things across teams and departments and functions, that there's a function that does that. And your job is a lot more, like, user-centric and thinking through how to tell the world about what you're building. And so it was a welcome change broadly. Now, does that apply to every company? and like PMs do things this exact way? No, it depends. I think it's actually challenging to find product managers

who are also really good marketers. And so I think it's actually like a rare skill set and like the art of marketing and the art of talking, conveying what you're building in the compelling way to people. It's a craft on its own and you have to build that over time. And so there are many product managers. that haven't exercised their craft. And so, of course, they can't just immediately, like, snap their fingers and become good at it, right?

It takes years to learn that skill. So it kind of, again, depends on the people, it depends on the organization. There's no blanket statement, in my opinion, where it's like PMM is the way or PM plus PMM is the way. Like, it depends. And just to clarify, the function you mentioned that kind of took off some of the load of PM is program management, I think is. Program management, yes. And they basically took on timelines.

staying on top of priorities and kind of the project manager part of the PMROL. Exactly. Awesome. Like, if you think about it this way, it's actually like the best version of the product management function, not dealing with like the project management and thinking about the product, the experience, the launch, the marketing, growth. Yeah. I mean, we had many product managers like internally always say like, oh, we feel like we're

doing very tactical work. We want to be much more strategic. And like, boom, like, this change actually makes the job significantly more strategic. Yeah. If you weren't doing that already. Awesome. Okay. I'm glad we spend time on that.

One last question before we get to our very exciting lightning round. We've talked about so many things that have gone really well. You're incredibly successful leader, person, PM. You've worked on so many successful projects. All these skills you've worked on that have been really helpful to you that we've been talking about. I want to take us to Failure Corner. I'm curious if there's a story. story of failure that you could share where you failed at some point in your career and what that

was and how that impacted you, how that helped you potentially in your career. I failed a lot. We've talked about the positives. There were also on my journey, a lot of humbling moments, still have them lots of failure. I would say the one moment I remember, this was probably in like 2018-ish. This was at Airbnb. It was a pretty dark time for me. And I felt overworked, overwhelmed, and I just wasn't a happy person, you know. This was a time where we were still scaling very, very quickly. And I just felt like I, I don't know, I, I wasn't like keeping up as much as I was in like maybe the earlier days, you know?

And I always remember thinking to myself, like, oh my God, am I going to tap out in 2018? Like, is this it for me? Like, you know? And it was, it was just hard for me because I was also a perfectionist. I wanted to help as much as I could. I had great, like, ambitions and dreams that are like, I'm going to keep going with Airbnb for a very long time. And I think in that moment,

I kind of hit rock bottom at some point. And I actually remember, you know, like during that time, realizing that so much of my identity was Airbnb and my job that I had trouble separating myself as a human being from my work.

And it was just realizing that, you know, was tough. Like I lost friends. I lost a lot of relationships. I lost many of my hobbies. Like I didn't spend as much time as I wanted to with my family and my parents. And at some point, I was just like, you know, I think in order for me to be a better

leader, like I just need to be a much more balanced human being. And that's where, ironically, I started spending less time on work and I became way more effective because I was just more centered, like, as a, as a person. So I reached out to people who I lost touch with. I spent much more time with my wife and my parents. I started gaming again and, like, all the little hobbies that I lost along the way. And it just made me happier. And because I was happier, I felt like every hour as a result was much more impactful, like, at the end of the day. So, yeah, like, that's, that's one thing that I, like think about quite a bit like you can't just it's really great when you pour your heart and soul

into something i think it it is very fulfilling right also you got to think about how to balance yourself as a person and if you lose sight of everything else in your life like i the recipe for disaster i appreciate you being really real with these a lot of people just share something that's not as real and so i appreciate you doing that and i love the advice of if you're going through a really hard time right now and are feeling burnt out and sad about your career, maybe just do less and maybe lean into your personal life more. That will help you be more successful in both. Yeah. You got to like find joy in the little things again. And if you like if you don't find joy in little things, like I just, I don't think you can show up with an open mind and the

curiosity that you need to be successful in in whatever job you have. I love that. Blad, before we get to a very exciting lightning round, is there anything else that you wanted to share that's on your mind that you thought would be good to leave listeners with. We covered a lot. So there may not be anything left, but is there anything just to give you a chance? No, I mean, like, I'm deeply thankful for the experiences that I've had. I mean, I've learned so much. I mean, I think, you know, I look back and there are definitely many lessons, but let's also be real. Like, a lot of it is luck, right? And a lot of just stuff just happens and it happens to go your way. So when things are hard, the one thing that I just want to maybe share is don't be too hard of yourself and cut yourself some slack.

You know, as long as you're waking up and you're actually pouring your heart and soul into something, you're truly giving it your all. Like, that's all you can really do. Amazing advice. This might come up again in our lightning round. With that, Vlad, we've reached our very exciting lightning round. Are you ready? Yeah, let's do it. Let's do it. Ding, ding. First question, what are two or three books that you recommended most to other people?

So I love sci-fi. Red Rising was one of my favorite books and then the Silo series. Highly, highly recommend. What do you think of the TV show version of the Silo series? What's that? There's a TV show of the Silo series. Read the books, though. I would like watch it after you read the book.

I agree. I don't know if you actually watch the show, but it's completely different story. it's like 90% just a whole new story I don't know what's going on there like foundation is similar I don't know what they're doing these days movies crazy amazing

okay the ever favorite recent movie or TV show that you've really enjoyed there's a TV show that I've enjoyed for a very long part of my life it's called Survivor and if you've heard of it probably everyone's probably

a bird of Survivor at this point the show is not dying it is actually very fun to watch and there's new twist every single sees them and so I probably watch like I think like 35 seasons or so. That's out of control. Do you feel like you would do well in Survivor if you were doing on?

Well, I think I would do well. My wife thinks I would die. I've got to find out. Okay. If I can nominate you for Survivor, I'll find a way. As long as you don't die. Next question. Do you have a favorite product that you've recently discovered that you really enjoy?

So one is actually a product that I cannot live without. I discovered it's in 2016. Discord. I cannot live without Discord. It is one of the products that I use for hours and hours every single day. I'm in all these gaming communities, and it's so much fun. I love that you use it for gaming, not for crypto. Just chatting with players and actually hanging out.

Yeah, love Discord. The product that I recently got introduced to is a game. It's actually a pseudo-boardish game called Gobbler. It's an advanced version of Tic Tactoe. And so me and my four and a half year old daughter play this before bedtime like every single day. She was just started schooling me at Tick, Taktow. And so I needed to upgrade. Gobbler, if you haven't played, it adds a new dimension where like pieces can gobble other pieces.

It's almost like playing in 3D a little bit. It is super fun to play. Wow. It's funny that she was schooling you to Tick, Tick, toe, which my understanding is you just tie all the time. It's amazing that she found ways to keep beating you. Yes. I think that says more about B that. I don't know.

Okay, gobbler. Next question, do you have a favorite life motto that you often think about, repeat back to yourself, share with friends or family, and work or in life? You never know. And it's a very simple motto. And what that means is, to me, even when there are things with low probability, shoot your shot, take a chance, take a leap. Sometimes you're going to be surprised how things turn out.

Beautiful. Final question. A tradition that are being be is to ask new folks a fun fact about themselves, which is always a hard question on the spot. But I'm going to ask you anyway, is there a fun fact about yourself that would be fun to share? Well, I kind of shared maybe a little bit of it. I absolutely love Survivor. And so I have tried to get on Survivor multiple times. And that is actually my dream to get on that show.

So if anyone out there watching who happens to Casper Survivor, like, I am here. I am available and I will probably not do very well but maybe I'll be entertaining I don't know This is your casting video right here This is it All right, Survivor people

Let's get Vlad on I think you would kill it I could see you This is all the skills we've talked about I think would be incredibly I don't know how to start fires No What I'm near the fire

Oh my God Vlad this was amazing I'm so happy we did this What a special episode I think for everyone that listened to this episode and goes through it all is they will guarantee they will become a better leader in so many ways. And so I'm really happy

that we did this. Two final questions. Where can folks find you online and who would you want to reach out to you? What kind of folks are you working with these days? And then finally how can listeners be useful to you? Hit me up if you want to chat on LinkedIn. I'll respond and we can like grab a coffee or Zoom or something. I mean, I'm an

investor now and like I love spending time with early stage founders. A lot of those early stage founders actually happen to be product managers at some point in their career. So I just like love chatting with folks about the problems they're facing or the ideas they have when they're thinking about starting a company. So yeah, if you're tinkering with cool things, like hit me up and we'd love to chat. And there's a segment, is there a segment of startups you're most focused on just for folks to know? I bet on people. So for me, like that's, that was always one of my learnings.

Like, I love meeting people that take me into a whole new dimension that I didn't even think was possible. Now, I do love consumer because a lot of that is my background. And so I try to focus on consumer, but at the end of the day, I'm focused on people. And so I go into many different directions where people think. Awesome. All right. And how can listeners be useful to you? If you want to chat, hit me up. Cool. Healthy find really cool startup opportunities to invest in. Yeah. Yeah. Yeah. Thank you. Lenny. Thank you so much. This was super fun. Thank you for having me on. It's absolutely my pleasure. Thank you, Vlad. And bye, everyone. Thank you so much for listening.

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