Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev

[00:00] 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 this 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 [00:30] that I need to understand to make a better decision. Is there something you can share about just what you learned from 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 and to 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, [01:00] 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 Loktev. This is a very special episode for me because Vlad was my manager at Airbnb for many years [01:21] And he's the person that I credit most for teaching me how to be an effective product manager and product leader. [01:27] 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's also a senior PM at Zynga, where he grew the game Words with Friends to over 14 million daily active users.

[01:57] 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 [02:20] 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'm 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. [02:50] of. [02:54] Vlad, thank you so much for being here and welcome to the podcast. Thank you. Excited to be here. [03:00] 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. [03:07] And even more interestingly, you managed me for many years at Airbnb. [03:10] I've also told you this before, but those years were probably, not probably, definitely the most transformative years of my career. [03:17] where I learned the most and the years that set me up for the success. [03:20] I ended up having later and also the crazy work that I do now. [03:24] So let me just say, I'm just really excited for other people to get a chance to learn from you.

[03:28] and to learn from the things that you've learned that helped you be successful and helped me be successful. [03:33] Thanks again for making time for this. [03:35] 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? [03:50] Uh, [03:50] Most importantly, how painful was it to manage me? [03:53] And how much time do you have? No, no, no jokes aside. [03:58] I've loved working with you, man. And I have to say, the one thing that I... [04:03] always deeply appreciated was that [04:06] 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, [04:14] 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 [04:23] 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. [04:35] 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.

[05:04] seeing what your users are actually doing in your apps so that you can optimize their experience. Next, Penda lets you deploy in-app guides [05:12] 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. And the new thing in Pendo, session replays, a very cool way to visualize user sessions. [05:26] I am not surprised at all that over 10,000 companies use it today. Visit Pendo.io/Lenny to create your free Pendo account today and start building better experiences across every corner of your product. P.S. You want to take your product-led know-how a step further? Check out Pendo's lineup of free certification courses led by top product experts and designed to help you grow and advance in your career. Learn more and experience the power of the Pendo platform today at Pendo.io/Lenny. [05:54] Pando. [05:58] This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. [06:28] Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com slash Lenny. That's V-A-N-T-A dot com slash Lenny.

[06:51] What I want to start talking about is [06:54] talking through and spending time on some of the skills that you developed and some of the skills that you're essentially [07:02] world-class app in my experience. [07:04] 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. [07:09] They have Jedi powers where you just get crazy stuff done, really hard stuff done, in a really subtle and really unique way that I haven't seen other people work. [07:17] and to show kind of the impact that it's had [07:20] Your growth trajectory at Airbnb is pretty absurd. [07:22] When you joined, I think you were kind of the same level, maybe. Maybe you were a level above, and you were an ICPM. [07:27] at Airbnb. [07:28] And then five years later, you're head of product, basically, for the homes business. [07:31] which is the core Airbnb business. And then a few years later, you're GM for the entire Airbnb Homes business, managing [07:38] people, designers, engineers, [07:40] research, marketing, and... [07:42] all these functions. [07:43] So, [07:44] I want to spend a little time on some of the things that helped you get to that point. [07:47] Let me just start with just a broad question. [07:49] Yeah. [07:50] What are some skills that you believe? [07:52] helped you be as successful as you've been. And they could be skills, maybe behaviors, maybe mindsets. [07:57] that helped you [07:58] Be successful. [08:00] Well, first, thank you for that introduction. [08:02] And... [08:03] I'm a work in progress. So there are many things that I am constantly working on. [08:09] I think for me, when I reflect on my journey at Airbnb, it was more about the mindset. [08:16] rather than [08:17] any kind of like skill. So, [08:20] For example, my...

[08:22] Main mindset was [08:25] impact, [08:26] above. [08:27] everything else so like impact impact impact impact and that's the only thing that mattered like my basically my entire career [08:34] And so I woke up every day and I asked myself two questions, basically. Number one, [08:40] what are the highest priorities for Airbnb today and over the next three months? [08:46] And then two, what can I do to actually make a meaningful dent in those priorities? Like what impact can I have? [08:53] And, [08:54] I always made sure that [08:57] whatever I worked on was very aligned with a top priority for the company and I would say [09:03] 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. [09:08] Because at the end of the day, you're spending so much of yourself and so much time [09:14] 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. [09:22] And so for me, [09:24] 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? [09:31] Now oftentimes, [09:33] It's... [09:34] figuring out the priorities is [09:37] relatively easy for in there's typically clarity around what [09:41] 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, [09:47] product quality or closing deals and closing sales. [09:51] you can typically figure out what the priorities are. It's oftentimes very hard

[09:55] to figure out how to make impact. [09:58] and what impact even means. [10:01] And so for me, like my... [10:03] motto there was always just learn the drivers of the business. So [10:08] Put your day job to the side for a second and just immerse yourself in understanding [10:14] why certain behaviors exist on the product that you're working on, right? [10:19] Can you influence that behavior? If you do X, what will happen essentially? [10:25] I spent a lot of time actually [10:28] blocking off like on my calendar just time thinking through the drivers and [10:32] with the question of what are the drivers that are going to have the most impact for the business. [10:37] And I remember when we worked on Instant Book together, I think this was back in 2014, that was not a random project. [10:44] so much thought behind [10:48] 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 the company. [10:57] So that was impact, impact, impact. [11:00] always just my [11:02] my motto, I guess. Let's actually spend more time here, because this is such... Not only have I seen you do this well, I've also seen the impact this mindset has had. [11:12] And I think people listening to this might be like, yeah, okay, impact rate. We're going to work on impact it. [11:16] But I think there's so much power to this that it's worth spending a little more time on. Yeah, let's do it. What do people do that's not this? Like, I imagine many people listening are like, oh, I work on things that are impactful. I'm doing great.

[11:27] What is it that you see that's not this? I think when a company matures, [11:31] I think there is... [11:32] you know, it grows, many more people join the team, the company gets bigger. At some point, a lot of people are working, [11:39] on similar things, teams start to form, then the entire department starts to form. And pretty quickly, I think a lot of people [11:48] begin to realize that you yourself are not in control of many things. [11:52] and you actually depend on what other people do. [11:56] Right. [11:56] And so a lot of people... [11:59] and I've done this too, have focused a lot of energy day to day on the dependencies, [12:05] rather than the things that you yourself can do in your day to day. So for example, [12:10] What I've seen as an organization scales, people transition from saying, [12:14] I can do X. [12:16] And they transition to saying, [12:19] "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, [12:27] 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 got to focus on the things that are actually within your control. [12:35] So again, it's more of a mindset shift. [12:38] The other thing I would say is, [12:40] Every single project that we worked on at Airbnb, [12:44] We did... [12:46] Back of the envelope, math. [12:48] with assumptions, [12:50] 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

[13:02] of what you have to believe. [13:03] in order for this project to be a success and for it to then make a big debt in whatever you're trying to achieve at the company. [13:09] So every single thing we did had that behind the scenes and we spent a lot of time on this to make sure that we were focused on the right things. [13:16] I remember there was a project we were going to work on, and I'm like, "I think this is a big opportunity." [13:20] Here's all my thinking on it and... [13:22] What I didn't have is here's the lift this could potentially drive. [13:26] Yeah. What you did is you just created this flow chart 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. [13:36] And you're right, it is actually a big opportunity, but this is how you want to show it. [13:39] Yeah, totally. [13:40] The other thing I'll say is also equally important is [13:43] Saying no [13:45] to a lot of things. And it's actually really hard because [13:49] We are... [13:51] basically trained and conditioned to say yes. You go to school, you follow the rules, [13:58] Like, you listen to your parents. [14:01] You... [14:02] 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 [14:08] 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 [14:18] will not make impact, right? [14:20] And so I learned very early on, [14:24] How to say no. [14:26] And, [14:27] It was hard emotionally. I've gone to many different debates and conversations, but ultimately, I think,

[14:34] 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. [14:47] And so, [14:49] I think during the back of the envelope math, [14:52] Being really good at 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 that was hard. So, maybe two quick questions here. [15:05] Do you have any tricks for how to say no well where someone's not like pissed off? [15:09] And then the other question I'll just throw in, you can take them however you want, is [15:12] What's your heuristic on how much people should like you as a PM? [15:16] Because you touched on, like, people don't need to necessarily love you. For... [15:20] Saying no. [15:22] 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. For me, the framework that I've always used was inquiry versus advocacy. [15:35] And I don't know if you remember, we've talked about it in some context where, [15:40] Basically, [15:42] A lot of people approach a conversation with a point of view and they begin advocating immediately, meaning, [15:48] we should do this or no, we should not do this. Right. [15:51] Me, I always took the opposite approach and I still do. I inquire first. [15:56] I dial up Inquiry. [15:57] 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.

[16:09] to make a better decision. [16:11] So in the beginning, dial up inquiry, [16:14] And then once the person who you're talking to feels heard and you actually have absorbed information, and maybe you changed your mind, maybe not though. [16:21] That's when you begin to advocate. [16:23] So, [16:24] Oftentimes, you just come into these conversations where everyone just advocates, advocate, advocate, advocate, and you're talking past each other. You're not even reflecting on what the other person is saying. [16:34] That's been my... [16:36] Sometimes when I talk too much, I tell myself, wait, [16:39] Inquire. [16:41] Dial down advocacy. Just take a breath. Take a moment. Take a beat. [16:46] and actually ask some questions and see why the other person feels so strongly. [16:51] I think that's such a good specific thing you can do because a lot of [16:54] 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!" [17:04] That's a terrible idea or that's going to take all this time. It's going to throw off a roadmap. [17:07] And there's like this bodily like, oh no, I need to stop this thingy step. [17:10] And so your advice here is pay attention to [17:13] Am I talking too long? [17:15] I guess is that the advice? Am I talking too long? Am I saying too much? And start just inquiring instead. Yeah. [17:20] Awesome. Totally. And lead with questions. Basically approach every conversation with curiosity. [17:25] Don't come in because people usually, when they prepare for a meeting, I've seen many PMs do this, you prepare with like, "Here's my view." [17:33] 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, you start the conversation with questions. Prepare the questions.

[17:44] 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. [17:49] and then check yourself to see if you still want to advocate for the same point of view or not. [17:54] We had an awesome episode with Ami Vorish, CPO at Fair, and she is also extremely good at this and a huge advocate of [18:01] 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 [18:09] Impact. [18:10] And it... [18:12] I use the analogy of the bear. [18:14] And I've always told myself, [18:16] Don't be afraid to poke the bear. [18:20] And what that means is [18:22] Don't self-censor. [18:24] If you have a strong view after you've really... [18:27] grounded yourself in the truth and you feel like you've done your homework and you've asked all the questions [18:33] If you still disagree, [18:34] 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. [18:41] And that's a it's interesting because I think a lot of especially as an organization matures, you find yourself [18:47] in meetings with many execs, [18:49] founders, et cetera, it's often hard to voice your real opinion and usually tone it down a little bit, right? Because you're afraid of... [19:00] being the only one who disagrees or [19:02] sounding stupid or things like that. [19:04] And so I remember it was probably like 2014 or 2013 where I, [19:08] I made a promise to myself. [19:10] I'm going to always poke the bear. [19:12] no matter how hard things get. Cause at the end of the day, like what's the worst thing that's going to happen? Like,

[19:16] Did I get fired? Why would I even be afraid of that? But if I do, I'll find another king. [19:22] Life is short and so, [19:24] You've done this really well, where I feel like you've also always, I remember when we were working in the book, you've definitely poked the bear where you were like, you guys are wrong. This is how we have to approach it. And I've always really appreciated it. [19:35] Thanks, man. [19:36] Is there an example of maybe working with Brian where he pokes [19:38] Brian, and like no. Yeah, absolutely. I've poked the bear many times. And by the way, I've been humbled many times. It's not like I poked the bear and I rightfully poked the bear. [19:47] Sometimes, [19:48] I learned stuff and I realized I... [19:51] was wrong a couple examples that come to mind like one [19:54] I remember having these debates [19:56] with [19:57] all basically senior leaders at Airbnb [20:00] if [20:01] just about every couple of years actually, [20:03] around how much supply 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, [20:14] That's cool if I represented the view that we needed [20:16] all supply out there to be on our platform regardless of if it was a [20:21] a person hosting, it was a vacation rental, it was a hotel, we just needed all supply on the platform. [20:29] 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 choose growth. [20:40] But at the same time, would it [20:42] in the long run, be a point of differentiation for us. And so I had a very different point of view. And

[20:48] It was very hard. [20:49] In that conversation, [20:51] you know, [20:52] 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. [21:00] Let me share... [21:02] why I think maybe we should go in a different direction. [21:05] And it's when I... [21:07] remember like [21:09] telling myself that I am here [21:11] to surface and share information that will help the group make a decision. [21:16] That's what gave me peace of mind to actually like poke the bear and be able to surface the things that I've seen. [21:22] I mean, the other thing is, [21:24] When we were working on the Instant Book, [21:28] change from request a book to instant book. [21:30] for the entire marketplace. That was very challenging. And I remember getting up on stage, [21:36] in front of the entire company, [21:38] And explaining why, like, [21:41] This is actually good for humanity. Like literally those words. [21:45] Many people disagreed and it was not an easy... [21:49] It was not an easy thing to do, but had to be done. [21:53] And one thread that I've noticed across all these things that I've noticed working with you is, [21:57] It's not like just making a case for something you can disagree with, it's showing the data. [22:01] that will convince them [22:03] they are wrong or here's what they're missing. It's [22:05] 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. Totally. Totally. I think I remember like doing a Q&A with the whole company on on the insulin book topic.

[22:19] This was a very long time ago, but I still remember [22:22] where instead of again, [22:24] advocating for a point of view [22:26] 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. [22:32] And it's [22:33] There's just something very disarming when you embrace the questions, you embrace the negativity. [22:41] And you have an open mind that maybe there are some things that you missed and some things that you didn't consider. [22:46] I love that. Okay, there's so many little nuggets already through this that I just want to [22:50] come back to and make sure people take away. [22:52] of how to be more successful. This is not just as a product leader, this is just as a leader in any company. [22:59] So the first is advice around [23:01] thinking about impact above all else. And the very simple heuristic that I wrote down as you're talking is, [23:07] Ask yourself, what are the priorities for the company? [23:11] How can I impact these priorities? [23:13] And to do that, [23:14] Think about the levers that drive the business and where do I think I can make an impact to [23:20] drive these parties and drive the business. [23:22] Two is inquiry first, when you disagree with something. [23:27] Or when you want to say no, [23:29] Start with understanding, asking questions, dialing up inquiry versus advocacy versus like, here's what I think. [23:36] 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?

[23:49] You're on. [23:51] 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 the bear for the sake of poking. [23:58] Share the information that you think will be helpful to make a decision. [24:02] Cool. Anything else? Any other things you've found to be really effective? [24:06] in helping you succeed. [24:08] Oftentimes, it's about also being able to be impactful [24:13] at a company that is in hyperscale and is growing quickly a lot of it is actually just psychological [24:19] So it's not like there are these core skills. Sure, you've got to have some baseline skills, right? [24:25] but a lot of it is day-to-day [24:27] regulating your mind. [24:29] And... [24:30] It's so easy to get lost in the sea of projects, the sea of priorities, the sea of opinions. [24:37] And like I said before, dwell on the dependencies that exist between teams without actually [24:44] asking yourself what you can do in the moment to make an impact. [24:48] And for me, like I've actually used two tools, which some of them you may remember. [24:53] that have helped me. [24:55] The first tool to write, this is again, purely psychological to help my mind. [25:00] It's the serenity prayer. [25:02] So the Serenity Prayer goes something like this. [25:06] Grant me the serenity. [25:08] to accept the things that I cannot change [25:11] the courage to change the things that I can, [25:14] and the wisdom to know the difference. [25:16] So I actually, that [25:19] prayer was so powerful for me that I actually wrote it out on the piece of paper

[25:25] on post-it notes and I would read that thing every other day. [25:30] And it would help me [25:32] Just take a step back from the day to day and just put into context what's actually important. And again, what is in my control today and the things that I can actually do. [25:41] So that... [25:42] Highly recommend. [25:44] Did not know that. [25:45] The other one, which you may remember, is the shit bucket. [25:48] I do remember that. So the shit bucket was a visual analogy. [25:54] where [25:55] I would take a piece of paper, and some of it actually wasn't as visual, it was like real. I would take a piece of paper, [26:00] I would write down [26:02] Something that wasn't going well. [26:04] 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. [26:16] I would crumble the piece of paper, [26:18] And I would throw it in my shit bucket, basically. [26:21] And the rule was, once I threw something in the shit bucket, I couldn't take anything out of the shit bucket. [26:26] So I would not dwell on the things that, [26:29] that I just needed to let go of. [26:33] So this was a very powerful tool that like I'm a perfectionist like I just [26:38] deeply care about many different things and I have a hard time letting go. [26:42] And so for me, it was just a reminder that, [26:46] I need to let some things go and focus on the things that matter. [26:50] And I actually remember... [26:52] even [26:54] going into one-on-ones with my directs.

[26:56] where I would sometimes leave, like I could tell, you know, [27:00] the PM is a bit frustrated about how things are going. And one of my first questions would be, [27:05] What are we throwing in the shit bucket today? [27:08] you know, [27:08] It's actually like a very liberating thing that you can do. [27:13] And did you have like a special trash can that was your shit bucket or is it the regular trash can? [27:17] Every media group always had a trash can. I would always throw stuff into the trash can whenever I got upset about something. It's like a different dimension trash can of trash can. [27:26] Is there something you remember throwing in the chid bucket that would be an interesting example or story to share? [27:31] I remember there was one person who I deeply wanted to hire. [27:35] where I thought was, [27:36] just phenomenal and would be such an amazing addition to the team. [27:40] I tried and tried and tried for a very long time and I just failed. I just could not get that person to join. At some point, it became counterproductive. [27:50] And I had to like... [27:52] Let go! [27:53] 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. [28:01] Just threw it in. [28:03] I love these two pieces of advice and it touches on how mentally challenging it is to be a leader at a hyper growth company. [28:11] Yeah. [28:12] 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. [28:21] There's a lot of pain behind it. Is there anything there that would be useful to people, you think? [28:25] There's a lot there. It's not like it was smooth sailing for me every single year. I had

[28:31] plenty of challenges [28:33] just personally, going through that journey. You're not [28:37] You take a job and then you're sometimes just not prepared [28:42] where it's going to take. And the reality is every three to six months, my job changed. [28:46] So I would just get comfortable in the role I was in. Let's say like in the very early days, I was [28:52] literally an icy growth PM with a tiny team got pretty comfortable. [28:56] And then like a year later, everything changed. And I was suddenly like leading a team of 20. [29:01] Then a few years later, things changed again. I was leading a team of a couple hundred. [29:05] Then a few years later, again, everything changed. And you just... [29:09] Everything that you take comfort in, [29:11] in your current role, breaks. [29:14] The process breaks. [29:16] How you hire breaks, how you spend your time breaks, the projects you work on, everything breaks. [29:20] And you got to reinvent yourself. And that is very hard to do. [29:25] So one thing that I've learned is like you got to. [29:28] Ask for help. [29:29] It takes a village, right? You can't [29:32] Just get there by yourself. That's actually something that Brian taught me where... [29:37] I mean, this guy, [29:39] just grew every six months. It was like a different person. And a lot of his secret sauce is [29:46] Not being afraid to ask people for help who are experts in the thing that you're trying to learn. [29:51] I mean, my motto is like, ask for the impossible and sometimes you're going to be surprised. Like, [29:56] There are people out there that are experts on something who actually want to help you. [30:01] So.

[30:02] That's awesome advice. [30:03] Also, the serenity prayer, so powerful. I did not know that about you. [30:08] 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... [30:15] that you think contributed to your success individually as a leader or any other [30:20] behaviors or mindsets. [30:22] I mean, I think it's... [30:25] building teams and [30:29] realizing that [30:32] Sometimes when you build a team, [30:35] And this is actually often misunderstood. I think when people build teams, they try to make sure every person on the team [30:42] is good at just about everything. You typically go through the process of, "Here are my strengths. Here are my development areas." [30:48] And typically the development areas, [30:51] are [30:53] Like. [30:54] 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, [31:02] That's the wrong mindset. Instead, what I've learned over time is instead of trying to find people that are good at everything, [31:09] you need to look for people who spite [31:12] On specific things? [31:14] 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. [31:23] but they spike on something that's very crucial to the team. [31:26] And if you assemble different spikes on a given team, [31:29] that team is going to do great things as long as,

[31:32] Everybody inquires and everybody starts asking questions, actually listens to other people versus just, you know, coming about that. [31:41] So even now, as an investor, when I talk to founders, [31:45] The first question in my head is like, [31:48] What is this founder spike on and how is that spike? [31:52] relevant to the problem that they're tackling today. [31:55] And how well does this founder hire [31:58] to bring other spikes to the team. Like that's literally like what I think about these days. [32:02] What are some examples of spikes just to make it even more real, like things that people might be good at? [32:06] 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 [32:16] They'll take marketplaces and there is someone who just understands the mechanics of how things work. [32:23] and just really spikes on understanding how you can take certain drivers [32:30] what you can do with those drivers and how you translate those drivers to measurable results. [32:35] There are people who spike on sales and who spike on just being able to... [32:43] to package something in a way that other people cannot package it right [32:47] There are people who spike in process. There are people who... [32:51] 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. [33:02] Some people are really great

[33:04] at product design. There are [33:07] I've seen quite a few founders actually who [33:10] can tell you immediately about what kind of interface is going to resonate with people and what kind won't and why. [33:16] you know, [33:17] So there's just some examples, but there are [33:19] many dimensions here. Awesome. Okay, as the last question along these lines... Yeah. [33:24] I'm going to share a few other skills that I noticed you're incredibly good at. [33:28] And how about just pick one that resonates with you and share some thoughts on how to get better at that and why that's important? [33:34] 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 he do that? I have no idea what he just did. [33:43] 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 [33:50] more time on stuff. That's something I remember from you. Just like spend a little more time on this doc. [33:54] make it a little bit better, refine it a little bit more. [33:57] That's two. Another is just getting stuff done and focus while also avoiding the limelight. You're not like... [34:03] 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. [34:09] You try to just get stuff done behind the scenes and not [34:12] not get attention from everyone. [34:15] Maybe those are a few. Is there one of those 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... [34:25] And being hyper-focused on the drop is... [34:30] It's something that's really important. [34:33] I mean, at index here, we also say keep the main thing the main thing.

[34:36] And [34:37] Just like in investing, same thing in operating. You got to focus on the actual job versus all the other things that you could potentially be doing. To me, I remember when I was actually hiring, [34:48] Product leaders, [34:50] And there's some product leaders who do [34:53] lots of different engagements outside of the company, whether it's [34:57] investing, advising, speaking, attending conference, all those things. And they were huge red flags to me because it was clear that this person [35:06] There was just something missing in their day-to-day. They didn't try to put them... [35:10] like all of them into the thing that they were doing. [35:13] And so for me, like, [35:14] It's really important. [35:16] When I hired people to hire people who were incredibly... [35:21] mission-driven and would dedicate every ounce of energy [35:25] to keeping the main thing the main thing. [35:27] Yeah, I talk about this on Twitter and LinkedIn. [35:30] This idea that [35:31] People see people like me and other PMs tweeting, sharing wisdom, and they're like, oh, these are the best PMs. They know so much. [35:38] But in reality, the best folks, you as an example, like, [35:41] Spend zero time on Twitter or LinkedIn. They're just doing the job. [35:44] trying to show great impact, trying to make a business successful, trying to build great products. [35:49] And I think it's important to remember you don't need to be [35:51] tweeting and writing medium articles. Yeah, I mean, I think there are, you know, people who find joy [35:57] in solving hard problems. And the joy you get from working on the hard problem [36:02] is fulfilling and you don't need to seek external validation.

[36:06] for the things you do every single day. [36:10] So yeah, I love hiring people like that. [36:12] Let me zoom out a little bit. So we've been talking a lot about the skills that you... [36:17] build and the mindset that you build to be successful individually. [36:20] But also, you managed large teams, you helped scale Airbnb, [36:24] massively through hypergrowth. [36:27] And there's a few skills I noticed you're really good at that were specifically applied to [36:30] Scaling an org, building an org, building teams, and things like that. [36:33] And so I want to spend a little time there. [36:35] You touched on this one a little bit, but I think there's more here around setting [36:39] priorities. [36:40] You're incredibly good at it. [36:42] Setting priorities, making sure everyone's aligned, making sure the main thing is the main thing. [36:47] You just talk about what else you've seen be important here as a leader of a larger growing org. [36:53] 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 [37:01] You got to let fires burn. [37:04] And what that means is you can do it all. [37:07] Like you just need to let go of things that are not important because if you, [37:12] have 20 different things that you're equally engaged on, it just means you don't actually know what is most important. [37:19] And so my motto has always been let fires burn. You got to be okay with some things not going well. [37:26] so that you can dedicate most of your energy on the few things that actually matter and the things that are most important. [37:32] Um, [37:33] And it's... [37:34] It's hard to do. [37:36] It doesn't feel good. Again, many people, especially PMs, are perfectionists. And so it like

[37:42] It hurts when things aren't going well and you just got to learn how to let things go. [37:47] Um, [37:48] the [37:49] What I always did was I kicked off every Monday with a leadership meeting where we would talk about our priorities for the week. [37:56] 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. [38:04] And we would jointly agree... [38:07] on the fires that we would let burn. [38:09] And so then when my partner, my engineering counterpart or my design counterpart would see a fire burning, [38:15] they would know, like, yep, we agreed that we're going to keep [38:18] Letting the fire burn for now. [38:20] And it was just really important to be aligned as a team on that. [38:23] Now, the other thing that I've learned, [38:26] is [38:27] You got to let other people burn fires too. [38:30] And it's very actually empowering. And oftentimes I remember... [38:34] Especially when you're leading a very large organization, there could be teams and teams and many different leaders who you're working with. [38:40] Oftentimes people come to you [38:42] and are basically like [38:45] Hey. [38:46] We got to do this new thing to drive goal one. [38:49] And I just don't have enough resources. [38:52] And we need to hire more people and we need to expand the resources of this team. [38:57] My first question, [38:59] always was well [39:01] 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 it?

[39:13] you know, [39:14] But, you know, I don't know. [39:16] To have those conversations, as a leader, you also have to recognize that [39:21] people on your team are eventually in a really good position [39:25] to gauge what fires should be burning and what should not be burning. Now the one thing I'll say though is it could be dangerous and there are some things [39:34] that you should never let burn because if you let them burn for too long, [39:38] bad stuff's going to happen. So I have a few of those examples for me that I have [39:43] like over the years learned [39:45] to not [39:46] Let burn. [39:47] First, [39:49] Timelines, major timelines. This is like huge product launches. [39:53] Once timelines slip, [39:55] you basically establish precedent that timelines are not as important and timelines can always slip. So you never want to set the precedent that timelines slip. [40:04] So that to me was when there was a major project and the timeline was significant slipping, I had never let that fire burn. Immediately jumped in. [40:11] The second is, [40:13] When. [40:14] there is disagreement on a strategic decision or maybe even part of the vision. [40:21] If you feel like that [40:24] exists. Like for example, if not everybody buys into Instant Book or there's just some disagreement about what supply should be on the platform. [40:32] You've got to squash that immediately. You cannot let that fire burn. [40:35] because... [40:37] He can spread. [40:38] I guess if I follow the analogy, it could become a wildfire, and then suddenly... [40:42] you have a team of people who are

[40:44] who don't believe in what they're doing, they lose meaning in their work, which is just really bad. [40:50] So, [40:52] You have to bring people together immediately when you feel like, [40:56] people, [40:57] whether it's many or few people do not believe in the direction that the company is headed. You got to squash that immediately. [41:04] Then the third one for me, and this was a bit painful to learn, [41:08] But. [41:09] You never let a senior hire... [41:14] Cross us. Burn. [41:16] 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, [41:25] We just needed to bring on [41:28] more people who had experiences or things that we were doing. [41:32] And anytime I delayed or I was like not fully engaged with the hiring process, especially a very senior person, it just it bit me. [41:42] for such a long time and it set the whole team back. And so [41:46] Those are the three things that I would never let burn. [41:48] But you gotta let. [41:49] A whole bunch of other stuff burned, for sure. [41:51] Such counterintuitive and amazing advice. [41:54] 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? [42:01] or a story that comes to mind of like, yeah, that's fine. You know, sometimes... [42:05] you would have examples where certain products [42:11] product launches didn't go well and let's say it just you know you weren't seeing the numbers the users weren't happy

[42:17] Like, okay, that's... [42:20] Sometimes you just need more time to understand what's actually wrong. You don't need to jump on it immediately. [42:26] So that's maybe like one example of a fire that I love burn quite a bit. [42:31] And quite frankly, at some point, [42:34] I had so many teams that I was working with that I just needed to prioritize even between the teams where like, [42:41] This team is the number one priority. [42:44] and I know that I need to be in design reviews with this other team, I just can't because I have to be thoughtful about how I'm spending my time in this given moment. [42:54] I actually have to deprioritize project. And so there are certain projects [42:58] that were important, but I let burn for a while because... [43:03] I just had to spend my energy elsewhere. And then of course, to myself, I was thinking, "Are we doing too many things?" [43:10] This is the right way to operate. [43:12] I think this is really useful for someone that, say, isn't ICPM on a team. [43:16] that's wondering why the hell our team is just wasting our time we're building all this stuff it's not working why [43:22] Why isn't anyone doing anything? Why aren't they giving some resources? Why aren't they re-producing? It's because [43:26] They know there's many other problems they're dealing with and they're letting this burn for them. Yeah, and this was actually a learning for me in an area where I would say I failed over time is [43:36] Just general communication to the broader organization, when you rise really quickly, you tend to under-appreciate, or I did, [43:44] just how important it is to communicate. [43:47] what as a leader you're spending your time on,

[43:49] and the areas that you think are the highest priority right now. [43:53] Eventually, I started doing a lot of all hands and I started sending the weekly thoughts from Vlad or just my random musings on what's in my head. [44:03] and [44:04] I realize that sharing that context with people is just so important. People actually want to hear from you. [44:09] And it's good to over communicate and it can help people understand certain things about their day to day. [44:15] I know that didn't come naturally to you. I mentioned that you kind of like to be [44:18] behind the scenes, under the radar, not in the limelight. So I could see why that wasn't something you were doing initially. [44:24] Is there anything more you can share there about what you've learned, what you learned about why that's important? Like, why are people, why, why spend time there? What happens if you don't? [44:32] Everybody wants to find meaning in their work. [44:34] And everybody... [44:36] typically wants to understand the reasons behind a decision. [44:40] And it's important to share [44:43] To take like... [44:45] I've done this myself where you just make a decision and you move on and you go on to the next decision. [44:50] and it's actually so, so helpful. [44:53] if you take 10% more energy and time, [44:56] to now bring everyone along around why a certain thing was decided. [45:02] Because it's going to help them just [45:04] 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 [45:12] partly why it's important. I mean, for me, it didn't come naturally to me. I'm like a pretty, [45:17] I don't know, I'm a deep introvert. I shy away from many different things and it had to be a learned thing.

[45:25] I think you're also a really good example of [45:27] Something I talk about here and there is you can be really successful in very different ways. [45:32] I'm also introverted. I think we're similar on the spectrum of colors or personality tests. [45:38] And you've been really successful. You can also be incredibly successful as a very extroverted person. [45:44] or someone that's very analytical. [45:46] And I think you're a great example of someone that's less, that's more reserved and doesn't want to. [45:50] and is introverted, as you said. And I think it's important for people to know you can be incredibly successful as a PM, as a huge leader. [45:57] from that place. [46:00] This episode is brought to you by EPPO. EPPO is a next-generation A-B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on EPPO to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And EPPO helps you increase experimentation velocity [46:29] the virtual tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Epo does all that and more, with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying, prolonged analytic cycles. Epo also makes it easy for you to share experiment insights with your

[46:59] flywheel. EPPO powers experimentation across every use case, including product growth, machine learning, monetization, and email marketing. Check out EPPO at getepo.com slash Lenny and 10x your experiment velocity. That's get EPPO.com slash Lenny. [47:18] Okay, so... [47:20] 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. [47:27] And I think this applies even if you're not the top of the org, even if you're [47:31] manager of managers even if you're a manager of nobody. [47:34] Yeah. Maybe the other thing I'll mention, as I reflect on setting priorities and just working. [47:42] I think... [47:43] A big lesson for me is that [47:46] Chaos is good. [47:48] Chaos is actually great. [47:50] 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. [48:01] And so, [48:02] I mean, I kind of... [48:04] As I reflect on my life, [48:06] I, uh, [48:08] I like cleaning up messes, I like when things are very organized, I like when there's a lot of clarity on how things are put together. [48:18] And, [48:19] 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 [48:27] Just a bit of chaos is so, so helpful. Just to give you an example,

[48:32] I remember... [48:33] me talking to Brian one day. [48:35] And he was like, [48:36] Hey! [48:38] I just don't feel good. Like something just feels off right now. [48:42] And I remember asking him, "What do you mean?" [48:46] Our numbers are open to the right. We're chipping quickly. Everything's great. What do you mean? What are you unhappy with? [48:52] And his response was, [48:55] Things are just too calm. I don't like it. [48:59] And I was like, okay, what do you mean? Like, com is great, right? Like, I operate in com. [49:06] And, um, [49:07] He then, [49:09] picked a project that he thought was important. I think it was actually host onboarding at the time. [49:15] And of course, in this project, we had like, [49:17] three or four, I remember we had this like perfectly crafted timeline, we're going to design this for the next four weeks. [49:23] and then we're going to start building [49:25] 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? [49:33] And he said, yeah, I don't care about any of that. We're going to design this in 24 hours. [49:37] And I was just like... [49:40] Mind blown! [49:41] Right? Like, [49:42] 问好 [49:44] to, [49:45] 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 this whole neat flow. [49:54] and [49:55] We did design it actually in 24 hours. It took a little bit longer, but we designed it very quickly. [50:01] And what I learned in that moment is that

[50:03] That was actually an example of chaos that he inserted into this very calm building process. [50:10] And that chaos forced us with our artificial time constraint [50:15] to dial up our intuition. [50:17] And to... [50:20] think a bit more creatively than maybe we would have in the past. Now, [50:24] That didn't always work because there were examples of this where you're just like, "I don't know what the answer is. I need more time to design this and to think about this problem." [50:33] There were definitely examples of that, but there were many examples where it was actually a great forcing function. [50:39] to go with your gut and actually innovate. [50:43] That's an amazing story. And it reminds me of something else just to take a quick tangent here is [50:47] Brian's incredible at just asking people always, [50:50] Okay, that's a great goal you have there. What would it take to 10x that goal? Yeah. [50:54] He gets the FP&A projection. He's like, great. OK, how do we 10x this? [50:58] and [50:59] 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 learned from Brian about thinking that big? [51:07] I think it's less about hitting the goal. [51:11] I think a lot of people, when they see really big goals, they immediately are afraid. [51:16] of the goals because they think, "Oh my God, I don't know how to hit this." [51:19] If we don't hit it, what happens? And you start thinking about all the downstream consequences. [51:24] The reality is, [51:25] It's not about hitting the goal. [51:27] It's about thinking how to hit the goal and going through the journey of the creative journey of like,

[51:33] What does the world need to look like for this to be true? This crazy goal to be true. How should we think about it? Oftentimes, [51:40] It pushes you to test extremes. [51:43] Right? [51:44] the whole world is going to operate this way or nobody in the world is going to operate this way versus like something in between. And usually it's when you start testing the extremes and you begin to like realize like, oh, [51:56] you know, [51:56] This is the path that we should actually take. [52:00] Yeah, I found exactly the same thing. Just thinking backwards from what is the best possible thing we could do? [52:06] versus incrementally forward ends up unlocking a lot of big ideas. [52:10] Something I imagine is in people's minds as they hear some of this 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 really hard. [52:22] You mentioned this, that this isn't necessarily for everyone. Not everyone needs to work at this company or work this way. [52:28] Part of it is hiring, is finding people that want to lean in, to work really hard. [52:33] Other people don't. Is there anything there just like, this is actually really hard and [52:37] It's not for everyone, but it also ends up being successful, and you end up having a good time a lot of times afterwards. [52:43] I find that those sprints where, like, designed this in 24 hours were... [52:49] brought a lot of connection to the team actually. [52:53] And they were like my most... [52:55] fun moments actually. [52:57] Because you kind of like... [52:59] You're forced to let go a lot of constraints. [53:02] All these organizational dependencies disappear, all the stuff that's kind of noise, and you can just start building. 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.

[53:17] just like shooting the shit and like [53:20] Throwing a whole bunch of ideas out there, no idea was too crazy, right? [53:25] Now, it's not for everybody, and so... [53:27] I actually in the interview process when I would hire PMs I was always [53:34] 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. [53:41] And so, [53:43] I think some leaders do this. It's like the anti-sell cell where [53:46] I will share... [53:48] the worst day, or what I think you will think as a candidate, what the worst day would be at Airbnb. [53:54] and then still ask you if you want to join the team. [53:57] And I would basically tell people, [53:59] We're going to work day and night. We're going to work weekends. Direction is going to change. The strategy is out the window every three months. The projects you're working on today, we're going to kill three weeks later. [54:08] The roadmap that you are right now auditing as you're deciding your offer when you actually join after you took some break from your other job is going to completely change. [54:16] And so, [54:17] Yeah. [54:18] getting people. I think the [54:20] The common thread there is, everything is changing all the time. You got to be cool with that if you want to join the scene. And totally fine, like if that's not for you. [54:29] I love that. It makes me think of something when a colleague... [54:32] I used to say at Airbnb, if you haven't changed teams or your desk in six months, something's about to happen. Something's about to change. Totally. Totally. [54:39] This unsell idea, there's a recent podcast episode where someone did something similar. He called it the unsell email where he sends the candidate, here's all the things based on all the things he heard from the candidate during the interview process.

[54:51] here's all the things you probably won't love about working here. [54:53] And the recruiter was always really mad at him for like, don't send that. My numbers are really going down. [54:58] 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 with recruiting on that piece of it. [55:15] Okay, so one other area I wanted to spend time on is [55:18] basically org design and hiring and people. So you were very good at building really effective teams, prioritizing them, bringing in amazing talent. [55:27] What can you share? [55:29] about things you've learned about as a company is growing and org is scaling about [55:32] or design hiring. [55:34] Yeah, so for me... [55:36] One of the hardest things about building teams and going through hyper growth was the fact that [55:44] You're going to lose a lot of friends on that journey. [55:46] Like you just have to be prepared to say goodbye to your friend. Meaning when you start, [55:52] You build really deep relationships with people when you're a smaller startup. You typically have one-on-one interaction and you know everybody. [56:00] and you have that connection with people. And the reality is, [56:04] Most people, if the company is truly going through hyper growth, [56:08] Most people are not going to scale. It is very rare for somebody to scale with a company. [56:14] At Index, we wrote a book, Scaling Through Chaos. [56:18] And there's this crazy stat [56:21] where

[56:22] Basically, when you look at [56:25] many, many companies that reached a thousand people and were successful. When you look back to the first 10 employees, [56:32] you realize that only two to three of those 10 first employees stayed with the company when the company reached a thousand people. [56:40] Right? [56:41] And that's just so... [56:43] like indicative of what will actually happen in practice like there are [56:49] Certain skills that you have [56:51] that are good for... [56:53] in the specific domain for a period of time. [56:56] And that time is not universal forever. At some point, everybody taps out. [57:04] It's. [57:05] just having that realization. [57:07] is... [57:09] It's tough. It's tough emotionally. It was one of the hardest things for me as a leader. [57:14] And I would say the way to break out of that [57:18] is to ask for help. [57:20] and to try to learn as much as you can about what [57:24] the next role for you is going to look like. [57:28] So that's one thing that I've learned. I would say another thing, [57:32] is that [57:34] All org charts suck. Like... [57:38] there is no good org chart. Every single org chart has problems. So, [57:42] You can be... [57:43] Organize around business units. You can be functionally organized. You can organize our own problems and the reality is you [57:48] Like every single one of those [57:50] Constructs suck. There are pros and cons to each approach.

[57:54] If you organize yourself into business units, [57:58] The problem you typically run into is silos. When people start basically advocating for their business unit with... [58:04] little regard for other business units, right? If you're a functionally organized, [58:09] 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, [58:17] could be slower to ship product, right? [58:19] Those are just examples. These are not universal issues, but those are examples [58:24] where [58:25] Regardless of how you organize, there are going to be problems. So for me, [58:29] One learning was if you're having a problem, [58:32] and you're trying to solve this problem. [58:35] But reorganizing and like a new org chart is rarely the solution. [58:39] It's not about the boxes and how you configure the boxes, right? [58:44] It's about [58:46] 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. [59:00] So my advice there also to founders who I talk to now, [59:05] Focus a lot less energy on actual org design. Study the different types and just pick one. [59:10] And once you pick one, [59:12] focus on the people, the culture, and how people work together. [59:15] That's really interesting. So basically you think people are overthinking [59:19] org design. Yes. [59:21] 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.

[59:29] in this thought. [59:30] I think incentives come down to culture and it's what you set as the fiber of your organization. [59:39] 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. [59:47] 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... [59:53] great business units. [59:54] things are going to start moving in. [59:56] You're not saying don't think about that and don't necessarily do that, but you're probably... [1:00:00] putting too much. [1:00:01] weight on that actually solving your problems. Yeah, I mean, [1:00:04] I think you want to certainly study [1:00:07] different ways of organizing and the pros and cons, but just know that no matter which choice you make, [1:00:13] it's going to suck and there are going to be organizational problems, right? [1:00:18] And you just need to go into it with, [1:00:20] wide open eyes [1:00:22] and then create process [1:00:24] to make sure that the, whatever the cons are, like it, [1:00:27] 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? [1:00:34] So there's all these other things that I would say [1:00:38] are much more important to focus your energy on. Awesome. [1:00:41] Anything else along these lines around org design or hiring that you think is really important? [1:00:45] Hiring, the one thing that is universal for me and always has been is mission over domain expertise. [1:00:54] Basically, mission over domain expertise, mission over skills, [1:00:59] I think that if you have like a raw, like that raw horsepower,

[1:01:04] And you're deeply... [1:01:07] like, [1:01:08] You just love the mission so much. [1:01:10] You can build whatever skills are necessary for the job. [1:01:13] And so I actually love taking... [1:01:16] As an operator, I love taking bets on people who are maybe earlier in their career. [1:01:20] who have energy [1:01:23] who have drive and who are deeply [1:01:25] thoughtful and deeply resonant with the mission that we're working on. [1:01:29] Because at the end of the day, like, [1:01:31] Strategy changes, orgs change, teams change, everything changes all the time. And the one constant, I think, is actually the mission. [1:01:40] And when shit gets really, really hard, [1:01:43] When your company almost collapses like we did during COVID, [1:01:47] 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 don't believe in the mission. [1:01:52] you lose meaning. [1:01:54] in your day to day and you start to disengage from the company. So I think that's actually the most important thing. [1:02:01] So what I'm hearing there is potentially if you're just like hitting it at your job, [1:02:05] 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 [1:02:11] there's not a lot that can change for you to actually be happy there because you don't actually care. [1:02:16] Yeah. [1:02:17] 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. [1:02:29] 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.

[1:02:35] and a team that is driving impact. [1:02:37] Do you have any advice there around just like where you are best suited to be successful within an org? [1:02:44] kind of coming at it from [1:02:45] where impact is most happening. I mean, I always thought about it as like the... [1:02:50] the combination [1:02:51] or almost like this Venn diagram of like there's one circle which is like all the different priorities. [1:02:57] that are important. [1:02:59] Then the other circle are your friends and where you spike. [1:03:04] And the intersection of the two is the place where you should be, right? [1:03:09] 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. [1:03:20] as you're learning more about the priorities and there's a match there. [1:03:23] The worst thing I think you can do is just sit in a job where you're not being impactful, you're not working on a top priority, and you're just kind of wasting your life. [1:03:32] You know, like, [1:03:33] Our time is short on Earth. You might as well wake up every day [1:03:37] and work on the hardest thing you can, where you can truly, based on who you are, [1:03:41] and the spikes you have make a dent in whatever is going to happen, right? [1:03:46] And also have the serenity prayer ready to go when things get really hard. [1:03:50] Okay, so... [1:03:51] What I want to do right now is summarize many of the things that you've shared before we get to talking about [1:03:56] Airbnb today and Brian Chesky's approach to product. [1:04:00] I guess before I try to summarize stuff, is there anything else you think is important skill-wise or... [1:04:04] behavior-wise that we haven't touched on? No, I think we've done a lot. Okay, cool. This is like almost Vlad's guide to being a successful product leader. I don't have it all summarized here yet. I just have a bunch of notes, but I thought it'd be fun just to try it.

[1:04:16] So one is, and the way I would think about this as you're listening to this is, what can I do to be more successful? [1:04:22] as a leader in a company and this is all kinds of stuff that i 100 [1:04:27] agree with is effective. [1:04:29] So one is impact above all else. [1:04:31] Thank you, Pat. [1:04:32] What is the company prioritizing? What is important to the business? [1:04:35] How can I drive impact there? And to do that, think about the levers. [1:04:39] in the business that move that and then find ways to work on those things. [1:04:42] This idea of inquiry first when you disagree with something. [1:04:46] shift your mindset to asking questions. [1:04:48] And then along those lines, when you disagree, this idea of poking the bear, [1:04:52] Sharing. [1:04:54] "Hey, here's why this might not be right. Here's why you might be wrong about this. Here's data that I found." Or data wouldn't help you understand. [1:05:01] Maybe you're wrong here. [1:05:03] okay what else uh saying no being really good at saying no just [1:05:07] And this comes back to impact and focus. [1:05:10] Let fires burn. [1:05:11] Really powerful idea. [1:05:13] Don't feel like everything has to be solved. [1:05:15] I'm similar to you where I feel like I need things in order and clean and [1:05:19] 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 [1:05:27] Align with your team on, we will let these things burn for now. [1:05:31] Anything you want to add, by the way, as I'm going through this? [1:05:34] No, gotta let everyone be a pyromaniac. [1:05:36] leads to great things. [1:05:38] Awesome. So along those lines, embrace chaos. Let things be chaotic sometimes because some of the best things come out of that. [1:05:44] And as you shared, Brian, sometimes just introduces a little chaos.

[1:05:47] to... [1:05:48] get people out of their little, their safe world a little bit. [1:05:51] 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. [1:06:02] 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. [1:06:10] as you rise and as you have to do things that maybe they're not lined with or happy about, [1:06:15] that are helping their career. [1:06:17] All org charts suck. [1:06:18] Nothing's going to be amazing. Don't over focus on the org chart, focus on the people. [1:06:22] and the culture. [1:06:24] 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 of the company. [1:06:30] Yeah. Okay. Is there anything else off the top of my head? It's so interesting. When I think back to my 10 years, [1:06:37] like, [1:06:38] Things that I actually remember the most [1:06:41] are [1:06:42] these moments with other people. [1:06:45] and not the... [1:06:47] some project or some product launch that's like going super well or you know us do really well with metrics it was [1:06:54] The things that really made, I think, Airbnb special and [1:06:59] I really, now that I think back to those 10 years of my experience, I deeply, [1:07:06] just resonate with are those little moments. One example, and this is why culture is just so important because these things don't just happen organically. [1:07:14] you have to be thoughtful about building culture. And then I think...

[1:07:18] 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, [1:07:24] My most memorable experience at Airbnb is the human tunnel. [1:07:28] And it was just... [1:07:30] this thing where I remember it was my first day [1:07:34] And I was standing behind this giant wall and there was silence in, I think it was a cafeteria. It was this huge, huge room, right? [1:07:42] And then, [1:07:43] Somebody like this engineer runs up to me and says, hey, go around to the other side of the wall. [1:07:48] And I turn. [1:07:50] And suddenly the room just explodes in cheering and clapping and everyone yelling my name and everyone is like, [1:07:56] basically doing a human tunnel with their hands. [1:07:58] 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. [1:08:10] And here I am, like, I don't know. [1:08:12] 12 years later, [1:08:13] 13 years later, [1:08:15] I still remember that as one of the most [1:08:19] Thank you. [1:08:20] amazing moments of the entire journey. [1:08:22] And it like I immediately felt accepted. [1:08:26] And. [1:08:28] I wanted to contribute to the team. [1:08:30] And a lot of the reasons why there were many moments like that throughout my 10 years, [1:08:36] And it was a result of how we hired people for certain core values and were very intentional [1:08:42] about [1:08:44] just [1:08:44] helping people integrate into this [1:08:47] crazy company that was growing super fast

[1:08:50] That's an amazing story. I feel exactly the same way. I went through a similar experience when I joined [1:08:54] And obviously the human tunnel eventually didn't scale and people started doing it like per team versus the entire company. [1:09:00] We could do a whole episode on Airbnb culture and learnings from that. [1:09:03] Interestingly, with the Human Tunnel, it's like, [1:09:05] It started, I think, with the founders, but it ended up being they had no involvement in these tunnels. It was just employees knew that this is the thing we're going to do for every new employee. [1:09:13] And so I think it's interesting. [1:09:14] 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? [1:09:22] two other companies you work with now of just like how to set up a great culture how to [1:09:27] do this well? I would say there's no single playbook. I would say the one thing that comes to mind is just being really intentional and thoughtful about it and actually dedicating energy to it. Just as much as you spend time building product, hiring people, you got to spend just as much energy actually. [1:09:43] thinking about culture and your core values. And so [1:09:47] Core values are very... [1:09:49] I would say, indicative of what the culture will be. So those two are very linked, right? [1:09:55] And once you have, once you think about core values, [1:09:58] I remember what worked really well was you don't just write your core values in the document somewhere and then no one ever opens it. [1:10:04] The key is, regardless of what the core values are, [1:10:08] You want to make sure that those core values are prominent in just about every single thing that you do. [1:10:13] Right. [1:10:13] So when you hire people, [1:10:16] you hire for certain core values. At Airbnb, we had core value interviewers

[1:10:21] My entire tenure, even when we had thousands of people already at the company, when we're hiring people, everybody had to pass core values interviews. [1:10:30] So it was very ingrained in how we hired. [1:10:33] and what we look for. [1:10:35] Then even performance reviews and promotions, no matter how much impact you made, no matter what you did, [1:10:42] If you were not also... [1:10:45] exemplifying core values, you didn't get promoted, you didn't get to the next level. And so, [1:10:51] Even in our performance conversations, those core values were very present in the day-to-day. [1:10:55] And then of course, [1:10:57] They were also printed everywhere. They were just like physically everywhere all the time. So I felt like every single person around me always knew what the core values were. [1:11:05] That's my biggest advice, don't copy some other company's core values. [1:11:10] Instead, just be intentional about what matters to your organization. [1:11:13] and then make sure [1:11:15] that those core values are freaking everywhere, part of every single process. Otherwise, like no one's going to care. [1:11:21] Just to reinforce what you're saying, I've been gone from Airbnb for five, six years now, and... [1:11:26] I still 100% remember the core values. [1:11:28] I'll go through them real quick. [1:11:31] Be a host. [1:11:32] Be a serial entrepreneur, which is serial as in the serial story. [1:11:37] champion the mission, [1:11:38] Simplify. Simplify, although they tweaked that one or they cut it right. And then Embrace the Adventure. Embrace the Adventure is my favorite. I love that one the most. [1:11:49] See, years later, you still remember. Exactly. Every Frame Matters was the other one they decided to cut out because they realized something they learned about core values that I thought is really interesting is

[1:12:00] They shouldn't be aspirational, they should be who you actually are. [1:12:03] 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 it. [1:12:08] reduce the ones we're focused on. Yeah. What I also really liked is that there were tangible examples always about what it meant [1:12:16] to embody this core value in your day-to-day work. Then it was very tangible for people versus just some overarching, like embrace the adventure. What does that actually mean? [1:12:26] 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. [1:12:32] people trained to interview in core values and they were like a specific volunteer team that [1:12:37] Part of the interview process, one of these people came in. [1:12:39] and they interviewed for Core Values, which was meant to represent what the founders were looking for initially. [1:12:44] 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. Most people at large companies are like, "I don't want to do any more interviewing. Oh my God, I'm doing interviews all the time." [1:12:58] People were like, it was a sense of this emotional, proud moment when you were basically given the keys and you were... [1:13:06] Somebody said, hey, like we actually think he would be fantastic at helping us think about [1:13:11] how to make sure every single new hire embodies these core values. I think that was so powerful. [1:13:16] Amazing. Okay, so again, we could spend an entire hour on the culture of Airbnb and all the things we've learned there. [1:13:22] 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.

[1:13:31] So we have Brian Chesky on the podcast, most popular episode of the podcast, turns out. [1:13:35] And he shared... [1:13:36] his approach to product, which [1:13:39] 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 make my company work this way. [1:13:49] The way he described Airbnb is it kind of moved from [1:13:51] bottom-up experimentation driven to very [1:13:54] top down. [1:13:55] We're going to have one roadmap. I'm going to be involved in everything. [1:13:59] Product managers are now product marketing managers and all these things that I think people are like, wow, that's really new and interesting. [1:14:06] 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. [1:14:12] So you're a really good example that you reported to Brian during this time. [1:14:16] 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... [1:14:27] from Airbnb for a second. Then we'll go into the concrete details of what Brian said. [1:14:31] I don't think... [1:14:33] you should copy another company's ways of working. The reality is, [1:14:38] It is... [1:14:40] How a company operates is so unique. [1:14:43] to the founders, to the leadership team, to all the employees and the domain, potentially the moment in time. [1:14:50] Because how companies operate also evolves sometimes over time and just certain different ways of operating might be needed, right? [1:14:58] So, [1:14:59] I wouldn't. [1:15:00] just

[1:15:01] copy someone else's way of operating. [1:15:04] Even like [1:15:05] At Airbnb, it was just very interesting for us. [1:15:09] It took us a long time to figure out how to operate. [1:15:13] Right? [1:15:13] And we were actually... [1:15:15] We didn't for a long time explain and give clarity to people of how we should even operate in the first place. We hired people from Facebook and Amazon and Google and Netflix and every Apple and every company. [1:15:28] And every person would come in with their own preconceived notions of how they wanted to work. [1:15:33] and oftentimes those opinions differed. And so because we never actually stated [1:15:40] like the Airbnb way for a very long time. [1:15:43] sometimes it would be chaotic, right? People would just... [1:15:46] wouldn't know how to operate and then you go from team to team [1:15:50] Teams will just operate very, very differently. And that was a problem. [1:15:53] So, [1:15:54] I think here the lesson for me was not necessarily... [1:15:58] There is one way to... [1:16:00] Every company should operate this way. [1:16:03] And it's much more about [1:16:05] Picking [1:16:07] an explicit way to operate [1:16:10] And then... [1:16:11] voicing it to every single person so that everyone has clarity in how to do their job. I think the worst thing is 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? [1:16:24] You know? [1:16:24] So, [1:16:26] That was kind of one lesson. [1:16:27] Now, specifically, double-clicking into Airbnb and where we moved. I think one of the things that Brian mentioned was,

[1:16:36] being [1:16:37] top down, right? I actually think [1:16:41] Top-down is this construct that has... [1:16:45] negative connotations associated with it quite a bit. [1:16:48] and it's often, at least in the context of Airbnb, I think misunderstood. [1:16:53] Like, [1:16:53] What people think top-down, [1:16:56] And I've had many, by the way, many of these conversations with folks, right? [1:16:59] So most people think, "Oh, there's a leader here in an ivory tower sitting somewhere, divorced from the team, [1:17:05] making a whole bunch of business accounts. Everyone else is powerless and can't do anything. [1:17:10] That's not actually a reality right of top down now. [1:17:13] In that room, [1:17:15] where we made many of the hard decisions with Brian, [1:17:19] The reality was [1:17:21] he asked a shit ton of questions right it was again he didn't advocate [1:17:26] in the beginning. [1:17:28] he would come in with tons and tons of questions. [1:17:32] and [1:17:33] he would listen. [1:17:34] And of course, sometimes like... [1:17:37] He would disregard certain things that he heard because he had very strong conviction in a different direction. But he listened. [1:17:45] And oftentimes he would also change his mind. [1:17:48] Right. And so [1:17:51] As a leader, like at Airbnb for so long, I never felt like [1:17:54] 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. [1:18:03] So, [1:18:05] Like,

[1:18:06] 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. [1:18:16] to make it sooner. [1:18:17] which is then also why [1:18:20] He wanted every leader to be in the details. [1:18:23] Why did he stress that for himself and every single leader on the team? It's because [1:18:27] When you get into that room and you start discussing [1:18:31] Many different directions you can go. [1:18:33] If the leaders in that room can't tell you what's actually happening with the business, then why are they there in the first place? [1:18:40] You can't then make a good decision with that group of people. So then suddenly, your team of 10, [1:18:46] You have to blow up to a team of 30, and if those people are not in the details, then you got to bring in 50 people. [1:18:52] and so [1:18:54] At some point, [1:18:55] You need to make sure that leadership is actually in the details, understand what's happening, [1:19:00] and can help [1:19:03] bring to light information that's going to help somebody make the right decision right so that's why [1:19:08] top down and being in the details, to me, they were actually very connected and they made a whole lot of sense. [1:19:13] now the one thing i'll say is like at some point [1:19:16] When you're working on many things, it is challenging to be in all the detail. [1:19:23] And if you mandate that product, [1:19:27] Cannot ship. [1:19:28] without certain people [1:19:31] being in every single detail, sometimes you could slow it down. That could be a con of that way of working.

[1:19:37] I would argue for us at Airbnb, [1:19:42] the quality of what we were releasing kind of suffered because we were [1:19:45] just push push push ship ship ship and people were shipping across the board [1:19:49] And I did feel as a leader, I wasn't proud of some of the things we were shipping. [1:19:54] And so I appreciated the intentional slowdown at the expense of our goals. [1:20:00] to get to a higher quality bar [1:20:03] and then amp up velocity again after everyone had a better understanding what quality actually was. [1:20:08] So, [1:20:09] we kind of had to slow down for a bit to then speed up later. [1:20:14] And I think a lot of it is, [1:20:18] Brian always wanted to make sure that [1:20:21] Thank you. [1:20:22] every leader [1:20:23] would be able to make decisions and have really good judgment. And he wanted to teach what that meant. [1:20:30] And I actually really appreciated that. [1:20:32] over the years. Now, [1:20:35] If you were to go back to semantics and say, hey, were we top down, bottom up? [1:20:39] those are just semantics. I would say, 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-censor, [1:20:51] and you were not afraid to poke the bear, you had an ability. [1:20:54] to voice information. So from that sense, there's lots of information that came bottom [1:20:58] up, [1:21:00] But then at the same time, there was also a lot of conviction and intuition and context that came top down. [1:21:05] because for a lot of these decisions, there was so much conversation.

[1:21:09] 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, I thought it was great. [1:21:18] We had a Boz on the podcast, CTO of Meta. [1:21:20] And I always thought of Meta as a very bottom-up organization where anyone can run experiments. They're shipping things all the time. [1:21:26] He's like, no, we're very top down. [1:21:27] 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. [1:21:33] And so I think to your point, a lot of people don't necessarily understand what that means. [1:21:37] and see things as bottom-up versus top-down. [1:21:40] Any other pros and cons, just real quick, on working this way? I think a lot of people are, a lot of founders are like, [1:21:46] Maybe I should move my company this way. Maybe I should just be involved in everything. [1:21:49] Maybe we need to move... [1:21:50] PMs to product marketing managers, [1:21:52] 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... [1:22:00] Which decisions... [1:22:02] and what part of the company [1:22:05] Do you have special like do you spike on? [1:22:09] and where you have edge and where you can help make the best decision. [1:22:13] And then I would argue then as a leader, then it is your job to be involved in those decisions. [1:22:18] For Brian, he always spiked in product, in design and marketing. So he was very natural. This is why he was basically the CPO. [1:22:27] That's why he was in all those decisions because those were his spikes and that's where he... [1:22:32] helped everybody move forward in a certain direction. I think for founders, you just need to recognize what

[1:22:40] do you spike on? What are the specific things that you have this [1:22:44] great insight that other people do not and immerse yourself in a lot of those decisions, right? [1:22:50] And there are some things that you might need to let go of, right, that [1:22:55] or maybe not as important, or maybe certain things that you won't add much to the conversation, and you have someone who you trust. [1:23:03] Who's going to uphold a certain quality bar or whatever? [1:23:06] So, [1:23:07] It's just being thoughtful about [1:23:09] where you spend your time. [1:23:12] leverage your friends, basically. [1:23:15] Final question along these lines, very specifically around this whole product marketing manager move. [1:23:21] To me, it feels like mostly like a rebrand of PM with the marketing work. [1:23:26] And in my eyes, PMs already should be doing marketing and thinking about adoption and growth and all these things. [1:23:32] And so I'm curious, just your take, do you think this is like [1:23:35] Oops. [1:23:35] with the future. [1:23:36] for PMs in general? You think this is just like a funny thing that Airbnb's trying and it doesn't really make a big dance? Thoughts on just this idea of, [1:23:43] PMs should be product marketing managers and we don't need PMs as PMs. I kind of felt like, and I was reading about this in the news when it blew up. I mean, it felt a little overblown to me, to be honest. [1:23:56] Like... [1:23:57] Just like you said, a lot of PMs at the company were thinking about how to talk to users about the products they were shipping. And they were basically marketers to some degree, right? [1:24:09] So I would say the rebranding

[1:24:13] 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. [1:24:26] And it... [1:24:27] it highlighted the importance of marketing. Or maybe it wasn't as highlighted before, but it was already happening at the company. [1:24:35] For a lot of the product leaders at 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. [1:24:48] In your job, [1:24:49] is a lot more user-centric and thinking through how to tell the world about what you're building. [1:24:55] And so it was a welcome [1:24:57] change broadly. [1:24:59] Now, does that apply to every company and like... [1:25:02] PMs, [1:25:03] Do things this exact way? No. [1:25:07] It depends. [1:25:08] I think it's actually... [1:25:10] challenging to find product managers [1:25:15] who are also really good marketers. [1:25:17] And so I think it's actually like a rare skill set and like the art of marketing and the art of talking like [1:25:22] conveying what you're building in a compelling way to people. [1:25:26] 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 that craft. And so of course they can't just immediately snap their fingers and become good at it. It takes years to learn that skill. [1:25:39] So, [1:25:41] It kind of, again, depends on the people. It depends on the organization. There's no blanket statement, in my opinion.

[1:25:47] where it's like PMM is the way or PM plus PMMM is the way. It depends. [1:25:53] 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. [1:26:02] Timelines. [1:26:03] Staying on top of parties and [1:26:05] kind of the project manager part of the PM role. - Exactly. - Awesome. Like if you think about it this way, it's actually like the best version of the product management function. [1:26:15] not dealing with like the project management and thinking about, [1:26:18] the product, the experience, [1:26:20] The launch... [1:26:21] the marketing, growth, [1:26:23] We had many product managers internally always say, "We feel like we're doing very tactical work. We want to be much more strategic." This change actually makes the job significantly more strategic. [1:26:37] Yeah. If you weren't doing that already. [1:26:39] Awesome. Okay. I'm glad we spend time on that. [1:26:41] One last question before we get to our very exciting lightning round. [1:26:45] We've talked about so many things that have gone really well. You're incredibly successful. [1:26:50] Leader, person, PM. [1:26:52] You've worked on so many successful projects, all these skills you've worked on that are [1:26:56] been really helpful to you that we've been talking about. [1:26:58] I want to take us to Failure Corner. [1:27:01] I'm curious if there's a story of failure that you could share where you failed some point in your career. [1:27:07] And what that was and what you... [1:27:09] how that impacted you, how that helped you potentially in your career. [1:27:12] I failed a lot. We've talked about the positives. There were also on my journey, [1:27:17] A lot of humbling moments.

[1:27:19] Still have them. [1:27:21] Lots of failure. I would say the... [1:27:26] The one moment I remember... [1:27:28] This was probably in like [1:27:30] 2018-ish. [1:27:32] This was at Airbnb. I'm, [1:27:35] It was a pretty dark time for me. [1:27:37] And I... [1:27:39] Bell. [1:27:40] overworked, [1:27:42] overwhelmed. [1:27:44] and up [1:27:45] I just wasn't a happy person, you know? [1:27:48] This was a time where... [1:27:52] We were still scaling very, very quickly. [1:27:56] And I just felt like I don't know, I I wasn't like keeping up as much as I was in like maybe the earlier days, you know. [1:28:04] And I 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? [1:28:10] And it was... [1:28:12] It was just hard for me because I was also a perfectionist. I wanted [1:28:16] to help as much as I could. I had great ambitions and dreams that I like, [1:28:21] I'm going to keep going with Irvingview for a very long time. [1:28:24] and [1:28:25] I think in that moment, I kind of hit rock bottom at some point and I actually, [1:28:30] Remember... [1:28:33] during that time, realizing that [1:28:36] So much of my identity [1:28:39] was Airbnb and my job. [1:28:42] that I had trouble separating myself as a human being from my work. [1:28:48] And it was...

[1:28:50] Just realizing that was... [1:28:53] was tough like I lost friends I lost a lot of relationships I [1:28:57] lost many of my hobbies like I didn't spend as much time as I wanted to with my family and my parents and [1:29:03] In [1:29:04] At some point, I was just like, you know, [1:29:07] I think in order for me to be a better leader, I just need to be a much more balanced human being. [1:29:13] And that's where... [1:29:15] Ironically, I started spending less time on work. [1:29:19] And that became way more effective. [1:29:21] Because I was just more centered. [1:29:24] like as a as a person so i i reached out to people who i lost touch with i spent much more time with [1:29:31] my wife and my parents I [1:29:33] started gaming again and like all the like little hobbies that are lost along the way and they just made me happier and [1:29:40] And because I was happier, I felt like every hour [1:29:43] as a result was much more impactful at the end of the day. [1:29:46] So yeah, that's... [1:29:48] That's one thing that I... [1:29:50] 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's [1:29:58] It is very fulfilling, right? [1:30:00] Also, you got to think about how to balance yourself as a person. If you lose sight of everything else in your life, like I... [1:30:07] It's a recipe for disaster. [1:30:09] I appreciate you being really real with these. A lot of people just share something that's not... [1:30:13] 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 you're feeling burnt out and

[1:30:21] sad about your career, maybe just do less. [1:30:25] and maybe lean into your personal life more, and that will help you be more successful in both. [1:30:29] Yeah. [1:30:30] You've got to find joy in the little things again. And if you don't find joy in little things, I don't think you can show up with an open mind and the curiosity that you need to be successful in whatever job you have. [1:30:43] I love that. [1:30:44] Vlad, before we get to our 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? [1:30:56] I'm deeply thankful for the experiences that I've had. I've learned so much. I think [1:31:02] I look back and there are definitely many lessons. [1:31:06] but let's also be real. [1:31:08] A lot of it is luck, right? And a lot of stuff just happens, and it happens to go your way. [1:31:14] So, [1:31:15] When things are hard, the one thing that I just want to maybe share is don't be too hard on yourself and cut yourself some slack. [1:31:23] 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. [1:31:31] Amazing advice. This might come up again in our [1:31:34] Lightning round with that Vlad we've reached a very exciting lightning round. Are you ready? Let's do it Let's do it ding ding ding first question. What are two or three books that you recommended most to other people? So I love sci-fi and [1:31:48] Red Rising was one of my favorite books. And then the Silo series.

[1:31:52] Highly, highly recommend. [1:31:53] 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 book, though. I would watch it after you read the book. I agree. Always reading the book is way better. I agree. I don't know if you actually watch the show, but it's a completely different story. [1:32:09] It's like 90% just a whole new story. I don't know what's going on there. [1:32:14] Like Foundation is similar. I don't know what they're doing these days with movies. [1:32:18] Crazy. Amazing. Okay. Do you have a favorite recent movie or TV show that you've really enjoyed? [1:32:23] There's a TV show that I've enjoyed for a very long part of my life. It's called Survivor. [1:32:27] I've heard of it. Everyone's probably heard of Survivor at this point. The show is not dying. It is actually very fun to watch, and there's new twists every single season. So I've probably watched, I think, like 35 seasons or so. [1:32:39] That's out of control. Do you feel like you would do well in Survivor? Well, I think I would do well. My wife thinks I would die. [1:32:47] You [1:32:49] I've got to find out. [1:32:50] Okay, if I can nominate you for Survivor, I'll find a way. [1:32:54] As long as you don't die. Next question. Do you have a favorite product that you've recently discovered that you really enjoy? [1:33:01] So one is actually a product that I cannot live without. I discovered this 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. [1:33:15] I love that you use it for gaming and not for crypto. Just chatting with players and actually hanging out. [1:33:21] Yeah, love Discord.

[1:33:22] The product that I recently got [1:33:26] introduced to is a game. It's actually a like pseudo board ish game called Gobbler. [1:33:32] It's an advanced version of tic-tac-toe. 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 tic-tac-toe. And so I needed to upgrade. [1:33:43] Gobbler, if you haven't played it, adds a new dimension where pieces can gobble other pieces. It's almost like playing in 3D a little bit. [1:33:50] It is... [1:33:51] Super fun to play. [1:33:52] Wow. It's funny that she was schooling you in Tic-Tac-Toe, which I... [1:33:56] My understanding is you just tie all the time. [1:33:58] It's amazing that she found ways to keep beating you. Yes. I think that says more about me. 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, your family, and worker in life? [1:34:13] You never know. [1:34:15] It's a very simple motto. What that means is, to me, [1:34:20] Even when there are things with low probability, [1:34:23] Shoot your shot. [1:34:24] Take a chance, take a leap. [1:34:27] Sometimes you're going to be surprised at how things turn out. [1:34:31] Beautiful. [1:34:33] Final question. [1:34:34] A tradition at Airbnb is to ask new folks a fun fact about themselves. [1:34:38] which is always a hard question on the spot, but I'm going to ask you anyway. [1:34:42] Is there a fun fact about yourself that [1:34:45] Would be fun to share. [1:34:47] Well, I kind of shared maybe a little bit of it. [1:34:50] I absolutely love Survivor, and so I have tried to get on Survivor multiple times, and it's actually my dream to get on that show. So if anyone out there watching who happens to cast for Survivor, like...

[1:35:01] I am here. I am available. [1:35:03] and I will probably not do very well, but maybe I'll be entertaining. I don't know. [1:35:08] This is your casting video right here. This is it. [1:35:12] Alright, Survivor people, let's get Vlad on. I think you would kill it. I could see you. All the skills we've talked about I think would be incredibly... I don't know how to start fires, though. [1:35:21] Yeah. [1:35:23] let him near the fire [1:35:25] Oh my God. [1:35:26] Vlad, this was amazing. I'm so happy we did this. What a special episode. I think for everyone that listens to this episode and goes through it all, they will... [1:35:33] I guarantee they will become a better leader in so many ways. [1:35:36] And so I'm really happy that we did this. [1:35:38] 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? [1:35:44] And then finally, how can listeners be useful to you? [1:35:47] hit me up if you want to chat on LinkedIn. [1:35:50] I'll respond and we can grab a coffee or Zoom or something. [1:35:54] I mean, I'm an investor now and I love spending time with early stage founders. [1:35:58] A lot of those early stage founders actually happened to be product managers at some point in their career. [1:36:03] So I just love chatting with folks about the problems they're facing or the ideas they have. [1:36:08] 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? [1:36:17] I bet on people. [1:36:19] So for me, that was always one of my learnings. [1:36:23] I love meeting people that take me into a whole new dimension that I didn't even think was possible. [1:36:27] 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 about.

[1:36:37] Awesome. All right. And how can listeners be useful to you? [1:36:40] If you want to chat, hit me up. [1:36:42] Cool. [1:36:42] Help you find really cool startup opportunities to invest in. [1:36:46] Yeah, yeah. [1:36:47] Thank you, Lenny. Thank you so much. This was super fun. Thank you for having me on. [1:36:50] It's absolutely my pleasure. Thank you, Vlad. And bye, everyone.