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 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, saying, "We should do this," or "No, we should not do this." For me, I always took the opposite approach. I inquire first. I'm going to ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision.

Is there something you can share about what you learned from Brian about thinking big? I remember talking to Brian one day. He was like, "Something just feels off right now." I remember asking him, "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 make leaps in product development. I've always told myself, "Don't be afraid to poke the bear."

What are some skills that you believe helped you be as successful as you've been? Impact, impact, impact, impact. That's the only thing that mattered. Today, my guest is Vlad Loev. This is a very special episode for me because Vlad was my manager at Airbnb for many years, and he's the person that I credit most for teaching me how to be an effective product manager and product leader within Airbnb. Vlad started as an IC PM. Five years later, he was leading product for the core Airbnb business, the homes business. A few years later, he 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, 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. Even though Vlad recently moved into venture capital as a partner at Index Ventures, he will always be a product manager at heart to me, and I'm very excited for more people to get to learn from Vlad. In our conversation, Vlad shares the skills, behaviors, and mindsets that most contributed to his success, including a ton of really tactical stuff, as well as the strategies and tactics that he's found most helpful in building and scaling a fast-growing organization. He also shares his thoughts on Airbnb's current ways of working, including their move away from traditional product management and 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. With that, I bring you Vlad Loev. Vlad, thank you so much for being here, and welcome to the podcast. Thank you! I'm excited to be here. I think this is going to be an extremely special episode. People will have heard in the intro that we worked together for many years, and even more interestingly, you managed me for many years at Airbnb. I've also told you this before, but those years were probably, not probably, definitely the most transformative years of my career, where I learned the most and the years that set me up for the success I ended up having later, and also the crazy work that I do now. So let me just say I'm really excited for other people to get a chance to learn from you and to learn from the things that helped you be successful and helped me be successful. So thanks again for making time for this.

Yeah, of course! I'm excited to be here. I mean, you were always a rockstar. You were a rockstar back then; you're a rockstar today. So excited to chat. I appreciate it. I don't know if I was a rockstar at the beginning. This is where my first question was going to go: What was it like managing me, Vlad? Most importantly, how painful was it to manage me? Man, how much time do you have? No, jokes aside, I loved working with you, man. I have to say the one thing that I always deeply appreciated was that no matter how hard things were, you always called out the elephant in the room. You always told me the stuff I did not want to hear. In 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 in the reality of what you're dealing with was just so, so helpful. I deeply appreciated that about you.

Wow, I think we're just going to be a little less, but I feel like I was able to do that because I knew you'd react well and you needed to hear those things.

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What I want to start talking about is some of the skills that you developed, some of the skills that you're essentially world-class at, in my experience, that I think might be helpful to a lot of other people. I used to joke with people that you're kind of this Jedi. You have like Jedi powers where you just get crazy stuff done, really hard stuff done, in a really subtle and unique way that I haven't seen other people work. To show the impact that has had, your growth trajectory at Airbnb is pretty absurd. When you joined, I think we were kind of at the same level, maybe you were a level above. You were an IC PM at Airbnb, and then five years later, you were head of product basically for the homes business, which is the core Airbnb business. Then a few years later, you were GM for the entire Airbnb homes business, managing a thousand people: designers, engineers, research, marketing, all these functions. So I want to spend a little time on some of the things that helped you get to that point.

Let me just start with a broad question: What are some skills that you believe helped you be as successful as you've been? There could be skills, maybe behaviors, maybe mindsets that helped you be successful. Well, first, thank you for that introduction. I'm a work in progress, so there are many things that I am constantly working on. I think for me, when I reflect on my journey at Airbnb, it was more about the mindset rather than any kind of skill. For example, my main mindset was impact above everything else. So like impact, impact, impact, impact. That's the only thing that mattered, basically, my entire career. I woke up every day and I asked myself two questions: number one, what are the highest priorities for Airbnb today and over the next three months? And then two, what can I do to actually make a meaningful dent in those priorities? What impact can I have? I always made sure that whatever I worked on was very aligned with a top priority for the company.

I would say if you find yourself in a situation where you're not working on the top priority of the company, you should probably get a different job because at the end of the day, you're spending so much of yourself and so much time at your job. You might as well really go for it and work on the hardest thing you can find, and if somebody's willing to give you a shot to build something crazy. For me, I always thought about what is the hardest thing that I can work on and how can I drive the biggest amount of impact? Now, oftentimes, figuring out the priorities is relatively easy, and there's typically clarity around what you have to focus on, whether it's expanding a team and really building out a specific team, whether it's growth rate, or focusing on product quality, or closing deals and closing sales. You can typically figure out what the priorities are.

It's oftentimes very hard to figure out how to make an impact and what impact even means. For me, my motto there was always just learn the drivers of the business. So put your day job to the side for a second and just immerse yourself in understanding why certain behaviors exist on the product that you're working on. Can you influence that behavior? What if you do X? What will happen essentially? I spent a lot of time actually blocking off time on my calendar just to think through the drivers with the question of what are the drivers that are going to have the most impact for the business? I remember when we worked on Instant Book together, I think this was back in probably 2014. That was not a random project. There was so much thought behind why we should focus on Instant Book and what was the core problem with Airbnb at that moment in time and what impact we thought we could have on the overall trajectory of the company. So that was impact, impact, impact. Always just my motto, I guess.

Let's actually spend more time here because this is such a powerful mindset. Not only have I seen you do this well, but I've also seen the impact this mindset has had. I think people listening to this might be like, "Yeah, okay, impact, great, work on impacting," 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? I imagine many people listening are like, "Oh, I work on things that are impactful. I'm doing great." What is it that you see that's not this? I think when a company matures, there are many more people who join the team, the company gets bigger. At some point, a lot of people are working on similar things. Then teams start to form, then entire departments start to form, and pretty quickly, I think a lot of people begin to realize that you yourself are not in control of many things, and you actually depend on what other people do. A lot of people, and I've done this too, have focused a lot of energy day-to-day on the dependencies rather than the things that you yourself can do in your day-to-day.

For example, what I've seen as an organization scales is people transition from saying, "I can do X," and they transition to saying, "Can the other team do Y so that I can do X?" I think that's a very dangerous place to be because at the end of the day, you just need to let go of some of these dependencies. You're not going to move mountains every single day, and you've got to focus on the things that are actually within your control. So again, it's more of a mindset shift.

The other thing I would say is every single project that we worked on at Airbnb, we did back-of-the-envelope math with assumptions to help us understand the impact that something would have. You needed to at least know those assumptions could be completely crazy and could be very challenging, but you at least needed to think through the mechanics of what you have to believe in order for this project to be a success and for it to then make a big dent in whatever you're trying to achieve at the company. 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're focused on the right things.

I remember there was a project we were going to work on. I thought, "I think this is a big opportunity. Here's all my thinking on it." What I didn't have was, "Here's the lift this could potentially drive." What you did is you created this flowchart of all the levers of the business and then said, "Okay, you're talking about this lever here, and if you move this 10%, here's the impact on the potential business." You're right; it is actually a big opportunity, but this is how you want to show it.

Totally. The other thing I'll say is also equally important is saying no to a lot of things. It's actually really hard because we are basically trained and conditioned to say yes. You go to school, you follow the rules, you listen to your parents, you don't want to disappoint people. When people ask for help, you help, and you want to be a really good teammate. But then at some point, you realize that's actually not the job. 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 tons of things that will not make an impact.

I learned very early on how to say no, and it was hard emotionally. I've gone to many different debates and conversations, but ultimately, I think maybe it doesn't win you many friends in the short term, but in the long term, people realize that when you say no to something, there's probably a really good reason behind why that thing may not be as impactful today and maybe we shouldn't even do it in the first place. So I think doing the back-of-the-envelope math and 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 no is hard.

So maybe two quick questions here. One is, do you have any tricks for how to say no well, where someone's not like, "Yes, pissed off"? The other question I'll just throw in, you could take them however you want, is what's your take on how much people should like you as a PM? Because you touched on how people don't need to necessarily love you for saying no.

First, you can't just be dogmatic and 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. I don't know if you remember, we've talked about it in some context where basically a lot of people approach a conversation with a point of view and they begin advocating immediately, meaning, "We should do this," or "No, we should not do this." For me, I always took the opposite approach, and I still do. I inquire first. I dial up inquiry; I tone down my advocacy, meaning I'm going to respect the other opinion. I'm going to ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision.

So in the beginning, dial up inquiry, and then once the person you're talking to feels heard and you actually have absorbed information, and maybe you changed your mind, maybe not, that's when you begin to advocate. Oftentimes, you just come into these conversations where everyone just advocates, advocates, advocates. You're talking past each other; you're not even reflecting on what the other person is saying. So that's been my approach. Sometimes when I talk too much, I tell myself, "Wait, inquire, dial down advocacy, just take a breath, take a moment, take a beat, and actually ask some questions and see why the other person feels so strongly."

I think that's such a good specific thing you can do because 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." Like, "No, that's a terrible idea," or "That's going to take all this time. It's going to throw off the roadmap." There's this bodily, like, "Oh no, I need to stop this thing ASAP." Your advice here is like, "Pay attention to am I talking too long? Is that, I guess, is that the advice? Am I talking too long? Am I saying too much?" and like start just inquiring instead?

Yeah, awesome, totally. Lead with questions. Basically, approach every conversation with curiosity. Don't come in because people usually, when they prepare for a meeting, I've seen many PMs do this, you prepare with, "Here's my view, and here are the bullets that support my view." That's the wrong way to approach it. I think what you want to do is go into the conversation or start the conversation with questions. Prepare the questions that come from a place of curiosity about the things that you want to know more about and you want to learn from the other perspective. Then check yourself to see if you still want to advocate for the same point of view or not.

We had an awesome episode with Amy Voris, CPO at Fair, and she is also extremely good at this and a huge advocate of starting with questions and understanding what she's missing.

Totally. The other thing I would say is the other motto that has really helped me drive impact is I use the analogy of the bear. I've always told myself, "Don't be afraid to poke the bear." What that means is don't self-censor. If you have a strong view after you've really grounded yourself in the truth and you feel like you've done your homework and you've asked all the questions, if you still disagree, if you still feel like we're going in the wrong direction, don't be afraid to poke the bear, no matter how hard things get.

It's interesting because I think a lot of, especially as an organization matures, you find yourself in meetings with many execs, founders, etc. It's often hard to voice your real opinion, and you usually tone it down a little bit, right? Because you're afraid of being the only one who disagrees or sounding stupid or things like that. I remember it was probably like 2014 or 2013 where I made a promise to myself: I'm going to always poke the bear, no matter how hard things get. Because at the end of the day, what's the worst thing that's going to happen? Did I get fired? Why would I even be afraid of that? But if I do, I'll find another gig. You know, life is short.

You've done this really well where I feel like you also always, I remember when working on Instant Book, you definitely poked the bear where you were like, "You guys are wrong. This is how we have to approach it." I've always really appreciated it.

Thanks, man. Is there an example of maybe working with Brian where you poked Brian?

Yeah, absolutely. I mean, I've poked the bear many times, and by the way, I've been humbled many times. It's not like I poke the bear and I rightfully poke the bear. Sometimes I learn stuff and I realize I was wrong. A couple of examples that come to mind: One, I remember having these debates with all the senior leaders at Airbnb just about every couple of years, actually, around how much supply should we have on the platform and what kind of supply should be on the platform. There was one school of thought where we needed all supply out there to be on our platform, regardless of if it was a person hosting, a vacation rental, or a hotel. We just needed all supply on the platform.

I came at it from a very different perspective where I felt like that wasn't actually our mission from the very beginning. Although I understood that in the short term the numbers would probably go up and you would choose growth, at the same time, that wouldn't, in the long run, be a point of differentiation for us. I had a very different point of view, and it was very hard in that conversation. Everyone's excited; everyone seems to be aligning around the point of view. To be the voice that's poking in there, like, "Nope, let me share why I think maybe we should go in a different direction," is challenging.

I remember telling myself that I am here to surface and share information that will help the group make a decision. That's what gave me peace of mind to actually poke the bear and be able to surface the things that I've seen. The other thing is when we were working on the transition from requested book to instant book for the entire marketplace, that was very challenging. I remember getting up on stage in front of the entire company and explaining why this is actually good for humanity—literally those words. Many people disagreed, and it was not an easy thing to do, but it had to be done.

One thread that I've noticed across all these things and noticed working with you is it's not just making a case for something you disagree with; it's showing the data that will convince them they are wrong or here's what they're missing. It's not like a speech; it's, "Here's the data," and asking them, "What data would you want to see to convince you this might not be as you think?"

Totally, totally. I think I remember doing a Q&A with the whole company on the Instant Book topic. This was a very long time ago, but I still remember where instead of, again, advocating for a point of view, I just asked all the people that were concerned what their main questions were, and then we just tackled them one by one. There's just something very disarming when you embrace the questions, you embrace the negativity, and you have an open mind that maybe there are some things that you missed and some that you didn't consider.

I love that. Okay, there's so many little nuggets already through this that I just want to come back to and make sure people take away how to be more successful. This is not just as a product leader; this is just as a leader in any company.

So the first is advice around thinking about impact above all else. The very simple puristic that I wrote down as you were talking is ask yourself, "What are the priorities for the company? How can I impact these priorities?" To do that, think about the levers that drive the business and where do I think I can make an impact to drive these priorities and drive the business.

Two is inquiry first. When you're trying to disagree with something or when you want to say no, start with understanding, asking questions, dialing up inquiry versus advocacy versus like, "Here's what I think."

Poking the bear, which is really fun, just like this idea of don't be afraid to disagree with someone in power. Your advice here is to disagree with data. You may not be aware of this; here, have you seen this? Hey, check this out, or what is it that would convince you you're wrong?

Yeah, 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. Share the information that you think will be helpful to make a decision.

Cool. Anything else? Any other things you've found to be really effective in helping you succeed?

Oftentimes, it's about also being able to be impactful at a company that is in hyper-scale and is growing quickly. A lot of it is actually just psychological. It's not like there are these core skills that, sure, you've got to have some baseline skills, right? But a lot of it is day-to-day regulating your mind. It's so easy to get lost in the sea of projects, the sea of priorities, the sea of opinions. Like I said before, dwell on the dependencies that exist between teams without actually asking yourself what you can do in the moment to make an impact.

For me, I've actually used two tools, which some of them you may remember, that have helped me. The first tool, again, is purely psychological to help my mind: the Serenity Prayer. The Serenity Prayer goes something like this: "Grant me the serenity to accept the things that I cannot change, the courage to change the things that I can, and the wisdom to know the difference." That prayer was so powerful for me that I actually wrote it out on a piece of paper and on Post-it notes, and I would read that thing like every other day. It would help me 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. So I highly recommend that.

I did not know that. The other one, which you may remember, is the "Shit Bucket."

I do remember that!

The "Shit Bucket" was a visual analogy where I would take a piece of paper, and some of it actually wasn't as visual; well, it was real. I would take a piece of paper, write down something that wasn't going well—perhaps a dependency, perhaps a project, perhaps a meeting that I was going to have that I knew I was going to be frustrated about, or maybe we didn't even decide to go the way that I deeply felt passionate about. I would write it down, crumble the piece of paper, and throw it in my "Shit Bucket," basically. The rule was once I threw something in the "Shit Bucket," I couldn't take anything out of the "Shit Bucket." So I would not dwell on the things that I just needed to let go of.

This was a very powerful tool. I'm a perfectionist; I just deeply care about many different things, and I have a hard time letting go. For me, it was just a reminder that I need to let some things go and focus on the things that matter. I actually remember even going into one of the ones with my direct reports where I could tell the PM was a bit frustrated about how things were going, and one of my first questions would be, "What are we throwing in the 'Shit Bucket'?" It's actually a very liberating thing that you can do.

Did you have a special trash can that was your "Shit Bucket," or was it the regular trash can?

Every meeting room 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!

Yeah!

Is there something you remember through that "Shit Bucket" that would be an interesting example or story to share?

I remember there was one person who I deeply wanted to hire, who I felt was just phenomenal and would be such an amazing addition to the team. 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, and I had to let go. I literally just wrote, "Okay, getting this person into the team is not going to happen. I got to move on at this point," and just threw it in.

I love these two pieces of advice, and it touches on how mentally challenging it is to be a leader at a hypergrowth company. Is there anything you can share there about just that part of the world? People see your career like, "Holy shit, look at him. He's running Airbnb's business. What an amazing life!" There's a lot of pain behind it. Is there anything there that would be useful to people, you think?

There's a lot there. It's not like it was smooth sailing for me every single year. I had plenty of challenges just personally going through that journey. You're not prepared for where it's going to take you. The reality is every three to six months, my job changed. I would just get comfortable in the role I was in. Let's say in the very early days, I was literally an IC growth PM with a tiny team. I got pretty comfortable, and then a year later, everything changed. Suddenly, I was leading a team of 20. Then a few years later, things changed again, and I was leading a team of a couple hundred. Then a few years later again, everything changed. Everything that you take comfort in in your current role breaks—the process breaks, how you hire breaks, how you spend your time breaks, the projects you work on, everything breaks. You got to reinvent yourself, and that is very hard to do.

One thing that I've learned is you gotta ask for help. You can't do it alone. It takes a village, right? You can't just get there by yourself. That's actually something that Brian taught me. This guy just grew every six months; it was like a different person. A lot of his secret sauce is not being afraid to ask people for help who are experts in the thing that you're trying to learn. My motto is, "Ask for the impossible," and sometimes you're going to be surprised. There are people out there that are experts on something who actually want to help you.

That's awesome advice. Also, the Serenity Prayer—so powerful! I did not know that about you. I want to spend time talking about things you've learned about scaling Airbnb in the org, but before we get to that, is there anything else that you think might be that you think contributed to your success as a leader? Any other behaviors or mindsets?

I think it's building teams and realizing that sometimes when you build a team—and this is often misunderstood—I think when people build teams, they try to make sure every person on the team is good at just about everything. You typically go through the process of, "Here are my strengths; here are my development areas," and typically the development areas are like you basically develop, you try to develop just about every single thing so that you can be good at almost every single skill that exists. I just think that's the wrong mindset.

Instead, what I've learned over time is instead of trying to find people that are good at everything, you need to look for people who spike on specific things and then add them to a team with different spikes. There's no single person that spikes on absolutely everything; that's very rare. But they spike on something that's very crucial to the team. If you assemble different spikes on a given team, that team is going to do great things as long as everybody inquires and everybody starts asking questions and actually listens to other people versus just coming about that.

Even now, as an investor, when I look for when I talk to founders, the first question in my head is, "What is this founder spiking on, and how is that spike relevant to the problem that they're tackling today? How well does this founder hire to bring other spikes to the team?" That's literally what I think about these days.

What are some examples of spikes, just to make it even more real? Things that people might be good at are like strategy, influence. What are some things you commonly see that are spike skills?

I think there's the very natural spike sometimes is you get a domain expert. There is a specific field, let's take marketplaces, and there is someone who just understands the mechanics of how things work and is really spikes on understanding how you can take certain drivers, what you can do with those drivers, and how you translate those drivers to measurable results. There are people who spike on sales and who spike on just being able to package something in a way that other people cannot package it.

There are people who spike in process. There are people who will literally every day think about how to get people to work together really well, and they just know how to get to the essence of that, how to connect the dots between different teams working together. Some people are really great at product design. I've seen quite a few founders who can tell you immediately about what kind of interface is going to resonate with people and what won't and why. So those are just some examples, but there are many dimensions here.

Awesome. Okay, as a last question along these lines, I'm going to share a few other skills that I noticed you're incredibly good at and how about just pick one that resonates with you and share some thoughts on how to get better at that and why that's important. One is influence. You're an incredibly strong influencer. You get a lot of stuff done that I think people will be like, "How did he do that? I have no idea what he just did." Another is you're very good at keeping a very high bar. That's one of the things I learned from you is just the importance of keeping a very high bar and spending more time on stuff. That's something I remember for me, just like spend a little more time on this doc, make it a little bit better, refine it a little bit more.

So that's two. Another is just getting stuff done and focus while also avoiding the limelight. You're not like—you try to not be in front and center. 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. You try to just get stuff done behind the scenes and not get attention from everyone. Maybe those are a few. Is there one of those you want to spend a little time on?

Yeah, I mean, first of all, thank you for saying that. Some of those resonate for sure. I think the getting stuff done and being hyper-focused on the job is something that's really important. I mean, at Index here, we also say, "Keep the main thing the main thing." Just like in investing, same thing in operating. You know, you've got to focus on the actual job versus all the other things that you could potentially be doing.

So to me, I remember when I was actually hiring product leaders, and there were some product leaders who would do lots of different engagements outside of the company, whether it's investing, advising, speaking, attending conferences, all those things. They were huge red flags to me because it was clear that this person—there was just something missing in their day-to-day. They didn't try to put them all into the thing that they were doing.

So for me, it's really important when I hire people to hire people who are incredibly mission-driven and would dedicate every ounce of energy to keeping the main thing the main thing.

Yeah, I talk about this on Twitter and LinkedIn, this idea that 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." But in reality, the best folks, you as an example, spend zero time on Twitter or LinkedIn. They're just doing the job, trying to show impact, trying to make a business successful, trying to build great products. I think it's important to remember you don't need to be tweeting and writing Medium articles.

Yeah, I mean, I think there are people who find joy in solving hard problems, and the joy you get from working on a hard problem is fulfilling. You don't need to seek external validation for the things you do every single day. So yeah, I loved hiring people like that.

Let me zoom out a little bit. So we've been talking a lot about the skills that you built and the mindset that you built to be successful individually, but also you managed large teams. You helped scale Airbnb massively through hypergrowth. There are a few skills I noticed you're really good at that specifically apply to scaling an org, building teams, and things like that. I want to spend a little time there. You touched on this one a little bit, but I think there's more here around setting priorities. You're incredibly good at setting priorities, making sure everyone's aligned, making sure that the main thing is the main thing.

Just talk about what else you've seen be important here as a leader of a larger growing org around setting priorities. I have a lot of strong opinions here with setting priorities. I would say the first one is—and this was my motto for the longest time, and this still is—you've got to let fires burn. What that means is you can't do it all. You just need to let go of things that are not important because if you have 20 different things that you're equally engaged on, it just means you don't actually know what is most important.

My motto has always been let fires burn. You've got to be okay with some things not going well so that you can dedicate most of your energy on the few things that actually matter and the things that are most important. It's hard to do. It doesn't feel good. Again, many people, especially PMs, are perfectionists, and so it just hurts when things aren't going well. You've just got to learn how to let things go.

What I always did was I kicked off every Monday with a leadership meeting where we would talk about our priorities for the week. We would talk about longer-term priorities. It was literally like, "For this week, what are we trying to get done?" It could only be one to three things, and we would jointly agree on the fires that we would let burn. So then when my partner, my engineering counterpart, or my design counterpart would see a fire burning, they would know, "Yep, we agreed that we're going to keep letting the fire burn for now." It was just really important to be aligned as a team.

The other thing that I've learned is you've got to let other people burn fires too, and it's very empowering. Oftentimes, I remember especially when you're leading a very large organization, there could be teams and teams and many different leaders who you're working with. Oftentimes, people come to you and are basically like, "We've got to do this new thing to drive goal one, and I just don't have enough resources. We need to hire more people; we need to expand the resources of this team." My first question always was, "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 them?

To have those conversations, you as a leader also have to recognize that people on your team are eventually in a really good position to gauge what fire should be burning and which should not be burning. Now, the one thing I'll say, though, is with this, it could be dangerous, and there are some things that you should never let burn because if you let them burn for too long, bad stuff's going to happen.

I have a few of those examples. For me, timelines—major timelines—this is like huge product launches. Once timelines slip, you basically establish a precedent that timelines are not as important and that they can always slip. You never want to set the precedent that timelines slip. So to me, when there was a major project and the timeline was significant slipping, I never let that fire burn. I immediately jumped in.

The second is when there is disagreement on a strategic decision or maybe even part of the vision. If you feel like that exists, like for example, if not everybody buys into Instant Book or there's just some disagreement about what supply should be on the platform, you've got to squash that immediately. You cannot let that fire burn because it can spread. I guess if I follow the analogy, it can become a wildfire, and then suddenly you have a team of people who don't believe in what they're doing. They're losing meaning; they lose meaning in their work, which is just really bad. So you have to bring people together immediately when you feel like people, whether it's many or few, do not believe in the direction that the company's headed. You've got to squash that immediately.

Then the third one for me—and this was a bit painful to learn—but you never let a senior hiring process burn. Meaning, you will always—and this is what I felt during my 10 years at Airbnb—I always felt underwater, and I always felt like we just needed to bring on more people who had experience in certain things that we were doing. Anytime I delayed where I was not fully engaged with the hiring process, especially a very senior person, it just bit me for such a long time and set the whole team back.

So those are the three things that I would never let burn, but you've got to let a whole bunch of other stuff burn for sure.

Such counterintuitive and amazing advice! You shared a bunch of examples of things that you don't want to let burn. Are there any examples you could share of things you let burn? Things that would surprise people or a story that comes to mind of like, "Yeah, that's fine"?

Sometimes you would have examples where certain products or product launches didn't go well, and let's say you weren't seeing in the numbers, the users weren't happy. Like, okay, that's sometimes you just need more time to understand what's actually wrong. You don't need to jump on it immediately, right? That's maybe one example of a fire that I let burn quite a bit.

Quite frankly, at some point, I had so many teams that I was working with that I just needed to prioritize even between the teams where like this team is the number one priority, and I know that I need to be in 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. So I actually had to deprioritize projects, and there are certain projects that were important, but I let burn for a while because I just had to spend my energy elsewhere.

Of course, I would tell myself, "Are we doing too many things? Is this the right way to operate?"

I think this is really useful for someone that, say, is an IC PM on a team that's wondering why the hell our team is just wasting our time. We're building all this stuff; it's not working. Why isn't anyone doing anything? Why aren't they giving some resources? Why aren't they reprioritizing? It's because they know there's many other problems they're dealing with, and they're letting this burn for now.

Yeah, and this was actually alerting for me in an area where I would say I failed over time is just general communication to the broader organization. When you rise really quickly, you tend to underappreciate—or I did—just how important it is to communicate what, as a leader, you're spending your time on and the areas that you think are the highest priority right now. Eventually, I started doing a lot of all-hands, and I started sending like the weekly thoughts from Vlad or just my random musings on what's in my head. I realized that sharing that context with people is just so important. People actually want to hear from you, and it's good to over-communicate. It can help people understand certain things about their day-to-day.

I know that it didn't come naturally to you. I mentioned that you kind of like to be behind the scenes, under the radar, not in the limelight, so I could see why that wasn't something you were doing initially.

Yeah, is there anything more you can share there about what you've learned, why that's important? Like, why are people—why spend time there? What happens if you don't?

Everybody wants to find meaning in their work, and everybody typically wants to understand the reasons behind a decision. It's important to share—to take, like, I've done this myself where you just make a decision and you move on, and you go on to the next decision. It's actually so, so helpful if you take like 10% more energy and time to now bring everyone along around why a certain thing was decided because it's going to help them just themselves make better decisions because now they have a lot more context about how this decision was made, and they can learn from that moment.

So that's partly why it's important. I mean, for me, it didn't come naturally to me. I'm a pretty—I don't know, I'm a deep introvert. I shy away from many different things, and it had to be a learned thing.

I think you're also a really good example of something I talk about here and there, is you can be really successful in very different ways. I'm also introverted; I think we're similar on the spectrum of colors or what thing, personality test. And you've been really successful. You can also be incredibly successful as a very extroverted person or someone that's very analytical. I think you're a great example of someone that's more reserved and doesn't want to—and is introverted, as you said. I think it's important for people to know you can be incredibly successful as a PM, as a huge leader from that place.

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Okay, so just to summarize the lesson we just talked about mostly is let fires burn. Basically, don't feel like you need to solve every problem as you rise in the ranks. I think this applies even if you're not the top of the org, even if you're a manager of nobody.

Maybe the other thing I'll mention, and as I reflect on setting priorities and just working, I think a big lesson for me is that chaos is good, and chaos is actually great. Sometimes you want to create chaos in an organization to push the organization to think creatively and to actually make leaps in product development.

As I reflect on my life, I like cleaning up messes. I like when things are very organized. I like when there's just a lot of clarity on how things are put together, right? Chaos is scary, and I think that this is very natural for a lot of people—for chaos to be scary. But I've seen examples when just a bit of chaos is so, so helpful.

Just to give you an example, I remember me talking to Brian one day. He was like, "Hey, I just don't feel good. Something just feels off right now." I remember asking him, "What do you mean? Our numbers are up and to the right. We're shipping quickly; everything's great. What do you mean? What are you going to be happy with?" His response was, "Things are just too calm. I don't like it." I was like, "Okay, what do you mean? Calm is great, right? I operate in calm."

He then picked a project that he thought was important. I think it was actually host onboarding at the time. Of course, in this project, we had like three or four—I remember we had this perfectly crafted timeline. We were going to design this for the next four weeks, and then we're going to start building, and we're going to deploy in certain pockets of users. We're going to learn; we're going to iterate, etc. Very rational timeline, right? He said, "Yeah, I don't care about any of that. We're going to design this in 24 hours."

That was just mind-blowing, right? One, how two, the ripples that's going to send through the organization because I knew all the people that were involved in building this, and we had this whole neat flow. We did design it actually in 24 hours. Well, it took a little bit longer, but we just moved very quickly.

What I learned in that moment is that the chaos—that was actually an example of chaos that he inserted into this very calm building process. That chaos forced us, with that artificial time constraint, to dial up our intuition and to think a bit more creatively than maybe we would have in the past.

Now, 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," right? There were definitely examples of that, but there were many examples where it was actually a great forcing function to go with your gut and actually innovate.

That's an amazing story, and it reminds me of something else. Just to take a quick tangent here, Brian's incredible at just asking people, "Okay, that's a great goal you have there. What would it take to 10x that goal?" He gets the PMA projection, and he's like, "Great, okay, how do we 10x this?" 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?

I think it's less about hitting the goal. I think a lot of people, when they see really big goals, they immediately get afraid of the goals because they think, "Oh my God, I don't know how to hit this. If we don't hit it, what happens?" You start thinking about all the downstream consequences. The reality is it's not about hitting the goal; it's about thinking how to hit the goal and going through the journey of that creative journey of 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, it pushes you to test extremes. When the whole world is going to operate this way or nobody in the world is going to operate this way versus something in between. Usually, it's when you start testing the extremes and you begin to realize, "Oh, you know, this is the path that we should actually take."

Yeah, I found exactly the same thing. Just thinking from backwards from what is the best possible thing we could do versus incrementally forward ends up unlocking a lot of big ideas.

Something I imagine is in people's minds as they hear some of the stuff, like designing something in 24 hours or thinking 10x bigger, is like, "I don't want to work that way. That sounds incredibly stressful. That sounds like what? I don't want that. That sounds really hard." You mentioned this—that this isn't necessarily for everyone. Not everyone needs to work at this company or work this way.

There's part of it is hiring, finding people that want to lean in to work really hard. Other people don't. Is there anything there just like this is actually really hard, and it's not for everyone, but it also ends up being successful, and you end up having a good time a lot of times afterwards?

I find that those sprints where we designed this in 24 hours brought a lot of connection to the team, actually, and they were like my most fun moments, actually, because you're forced to let go of a lot of constraints. All these organizational dependencies disappear—all the stuff that's kind of noise—and you can just start building, right?

For me, especially when you're not doing this by yourself and you're doing this with a team of people, it was deeply rewarding because you were all working together, just shooting the shit and throwing a whole bunch of ideas out there. No idea was too crazy.

Now, it's not for everybody. In the interview process, when I would hire PMs, I was always—not always in the early days, I guess I had to learn this—but in the later days, I always set expectations about how we work. Some leaders do this; it's like the anti-sell. I would share the worst day or what I think you will think as a candidate what the worst day would be at Airbnb and then still ask you if you want to join the team.

I would basically tell people, "We're going to work day and night. We're going to work weekends. Directions are going to change; the strategy is going to go out the window every three months. The projects you're working on today, we're going to kill three weeks later. The roadmap that you are right now auditing as you're deciding your offer when you actually join after you took some break from your other job is going to completely change."

It's totally fine if that's not for you.

I love that. It reminds me of something my colleague used to say too: If you haven't changed teams or your desk in six months, something's about to happen.

Something's about to change!

Totally!

This un-sell 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 I heard from the candidate during the interview process. Here's all the things you probably won't love about working here." The recruiter was always really mad at him for, like, "Don't send that! My numbers are really going down because of this email!" But long-term, it ends up being really successful for them.

Yeah, I mean, you're going to probably hire fewer people that way, but you will hire the right people. So I think then you're going to actually have a team that you can rely on for years and years and years as things change.

Yeah, just have to align incentives with recruiting on that bit of it.

Okay, so one other area I wanted to spend time on is basically org design and hiring and people. You were very good at building really effective teams, prioritizing them, and bringing in amazing talent. What can you share about things you've learned as a company's growing and an org is scaling about org design and hiring?

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

The reality is most people, if the company is truly going through hypergrowth, most people are not going to scale. It is very rare for somebody to scale with a company. We actually, at Index, wrote a book called "Scaling Through Chaos," and there's this crazy stat where basically when you look at many companies that reached a thousand people and were successful, when you look back to the first 10 employees, you realize that only two to three of those 10 first employees stayed with the company when the company reached a thousand people.

That's just so indicative of what will actually happen in practice. There are certain skills that you have that are good for a specific domain for a period of time, and that time is not universal forever. At some point, everybody taps out, and so it's just having that realization. It's tough emotionally. It was one of the hardest things for me as a leader.

I would say the way to break out of that is to ask for help and to try to learn as much as you can about what the next role for you is going to look like. So that's one thing that I've learned.

I would say another thing is that all org charts suck. There is no good org chart. Every single org chart has problems. You can be organized around business units; you can be functionally organized; you can be organized around problems. The reality is every single one of those constructs sucks. There are pros and cons to each approach.

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

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

So my advice there also to founders who I talk to now is focus a lot less energy on actual org design. Study the different types and just pick one, and once you pick one, focus on the people, the culture, and how people work together.

That's really interesting. So basically, you think people are overthinking org design?

Yes.

How do you think about incentives and goals and how that kind of impacts all that stuff? Because there's people, and then there's like, "Here's your goal. Here's how you're measured," and that's what they're going to work on in this thought.

I mean, I think incentives come down to culture, and it's what you set as the fiber of your organization. So again, I think you can align incentives, and people will be excited to make an impact on the organization regardless of how an organization is actually organized.

That's a really interesting takeaway because I think a lot of people think about, "Okay, if we just org this and put this person here and create business units, things are going to start moving." You're not saying don't think about that and don't necessarily do that, but you're probably putting too much weight on that actually solving your problems.

Yeah, I mean, I think you want to certainly study different ways of organizing and the pros and cons, but just know that no matter which choice you make, it's going to suck, and there are going to be organizational problems. You just need to go into it with wide-open eyes and then create processes to make sure that whatever the cons are—if people are in silos, well then you've got to have a really good way of bringing people together and creating the right incentives to make sure people collaborate.

There are all these other things that I would say are much more important to pour your energy into.

Awesome. Anything else along these lines around org design or hiring that you think is really important?

I would say the one thing that is universal for me and always has been is mission over domain expertise—basically, mission over domain expertise, mission over skills. I think that if you have that raw horsepower and you're deeply—like you just love the mission so much—you can build whatever skills are necessary for the job.

As an operator, I love taking bets on people who are maybe earlier in their career, who have energy, who have drive, and who are deeply thoughtful and deeply resonate with the mission that we're working on. Because at the end of the day, strategy changes, work changes, teams change, everything changes all the time, and the one constant I think is actually the mission.

When shit gets really, really hard, when your company almost collapses like we did during COVID, the thing that gets you through those hard times is the mission. If you don't have mission, you don't believe in the mission, you lose meaning in your day-to-day, and you start to disengage from the company. So I think that's actually the most important thing.

So what I'm hearing there is potentially if you're just hitting it at your job or you think it's just not going anywhere, it might be that you don't actually care that much about what the company's trying to do in the mission, and maybe there's not a lot that can change for you to actually be happy there because you don't actually care.

Yeah, fascinating. Something that I wanted to come back to real quick: a lot of your advice comes back to impact—like impact above all else, drive impact, focus. This comes back to what is the most important thing to do. Something that I think about a lot is how do you be successful within a company? One of the levers is go to a place and a team that is driving impact. Do you have any advice there around just like where you are best suited to be successful within an org, kind of coming at it from where impact is most happening?

I mean, I always thought about it as like the combination or almost like this Venn diagram of like there's one circle which is all the different priorities that are important. Then the other circle is your strengths and where you spike. The intersection of the two is the place where you should be. 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 pretty decent at, but you definitely want to double down on it as you're learning more about the priorities, and there's a match there.

The worst thing I think you can do is just be in a job where you're not being impactful, you're not working on the top priority, and you're just kind of wasting your life. Our time is short on earth; you might as well wake up every day and work on the hardest thing you can where you can truly, based on who you are and the spikes you have, make a dent in whatever is going to happen.

Right, and also have the Serenity Prayer ready to go when things get really hard!

Yeah!

Okay, so what I want to do right now is summarize many of the things that you've shared before we get to talking about Airbnb today and Brian Chesky's approach to product. I guess before I try to summarize stuff, is there anything else you think is important skill-wise or behavior-wise that we haven't covered?

I think we've done a lot.

Okay, cool. So I'm going to just—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.

So one is—and the way I would think about this as you're listening to this is how do I be more—what can I do to be more successful as a leader in a company? This is all kinds of stuff that I 100% agree with is effective.

So one is impact above all else. Think about what is the company prioritizing, what is important to the business, how can I drive impact there? To do that, think about the levers in the business that move that and then find ways to work on those things.

Yeah, 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. Share the information that you think will be helpful to make a decision.

Cool. Anything else? Any other things you've found to be really effective in helping you succeed?

Oftentimes, it's about also being able to be impactful at a company that is in hyperscale and is growing quickly. A lot of it is actually just psychological. It's not like there are these core skills that, sure, you've got to have some baseline skills, right? But a lot of it is day-to-day regulating your mind. It's so easy to get lost in the sea of projects, the sea of priorities, the sea of opinions. Like I said before, dwell on the dependencies that exist between teams without actually asking yourself what you can do in the moment to make an impact.

I did not know that. The other one, which you may remember, is the "Shit Bucket."

I do remember that!

Did you have a special trash can that was your "Shit Bucket," or was it the regular trash can?

Every meeting room 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!

Yeah!

Is there something you remember through that "Shit Bucket" that would be an interesting example or story to share?

What are some examples of spikes, just to make it even more real? Things that people might be good at are like strategy, influence. What are some things you commonly see that are spike skills?

So for me, it's really important when I hire people to hire people who are incredibly mission-driven and would dedicate every ounce of energy to keeping the main thing the main thing.

What I always did was I kicked off every Monday with

Even operate in the first place because we hire people from Facebook, Amazon, Google, Netflix, Apple, like every company, right? Every person would come in with their own preconceived notions of how they want it to work, and oftentimes those opinions differed.

Because we never actually stated like the Airbnb way for a very long time, sometimes it would be chaotic. People just wouldn't know how to operate, and then you go from team to team, and teams would just operate very, very differently. That was a problem.

So I think here the lesson for me was not necessarily that there is one way every company should operate. It's much more about picking an explicit way to operate and then voicing it to every single person so that everyone has clarity on how to do their job.

I think the worst thing is when 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?" So that was kind of one lesson.

Now, specifically, going double-clicking into Airbnb and where we moved, I think one of the things Brian mentioned was being top-down. I actually think top-down is a construct that has negative connotations associated with it quite a bit.

This is often, at least in the context of Airbnb, misunderstood. Most people think, "Oh, there's a leader here in an ivory tower sitting somewhere divorced from the team, making a whole bunch of decisions," and everyone else is like powerless and can't do anything. That's not actually the reality of top-down.

Now, in that room where we made many of the hard decisions with Brian, the reality was he asked a ton of questions. He didn't advocate in the beginning; he would come in with tons and tons of questions, and he would listen.

Of course, sometimes he would disregard certain things that he heard because he had very strong conviction in a different direction, but he listened. Oftentimes, he would also change his mind.

As a leader at Airbnb for so long, I never felt like I wasn't listened to or like he was just making these random decisions. I always had an ability to influence and an ability to voice where I felt like the company should go.

So yes, he made a lot of decisions, but he made sure he was informed in those decisions, and many of us were contributing to all the information he needed to make the decision.

This is then also why he wanted every leader to be in the details. Why did he stress that for himself and every single leader on the team? It's because when you get into that room and you start discussing many different directions you can go, if the leaders in that room can't tell you what's actually happening with the business, why are they there in the first place?

You can't then make a good decision with that group of people. Suddenly, you're a team of like 10, and you have to blow up to a team of 30. If those people are not in the details, then you have to bring in like 50 people.

At some point, you need to make sure that leadership is actually in the details, understands what's happening, and can help bring to light information that's going to help somebody make the right decision.

That's why, to me, top-down and being in the details were actually very connected, and they made a whole lot of sense.

Now, the one thing I'll say is that at some point, when you're working on many things, it is challenging to be in all the details. If you mandate that product cannot ship without certain people being in every single detail, sometimes you could slow it down.

That could be a con of that way of working. I would argue for us and for Airbnb, the quality of what we were releasing kind of suffered because we were just push, push, push, ship, ship, ship. People were shipping across the board, and I did feel as a leader like I wasn't proud of some of the things we were shipping.

I appreciated the intentional slowdown at the expense of our goals to get to a higher quality bar and then amp up velocity again after everyone had a better understanding of what quality actually was.

So we kind of had to slow down for a bit to then speed up later. I think a lot of it is that Brian always wanted to make sure that every leader would be able to make decisions and have really good judgment, and he wanted to teach what that meant.

I actually really appreciated that over the years. Now, if you were to go back to semantics and say, "Hey, were we top-down or bottom-up?" those are just semantics.

I would say we were actually, 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 and you were not afraid to poke the bear.

You had an ability to voice information. From that sense, there was lots of information that came bottom-up. But then at the same time, there was also a lot of conviction, intuition, and context that came top-down.

Because for a lot of these decisions, there was so much conversation, the reality is I think the way we operated was actually somewhere more towards the middle on a day-to-day basis.

This is why I thought it was great. We had a boss on the podcast, the CTO of Meta, and I always thought of Meta as a very bottom-up organization where anyone can run experiments. They're shipping things all the time.

He's like, "No, we're very top-down. We tell people here's the things we're building this year, here's our big bets, here's what we're going to prioritize."

I think, to your point, a lot of people don't necessarily understand what that means and see things as bottom-up versus top-down.

Any other pros and cons, just real quick, on working this way? I think a lot of people, a lot of founders are like, "Maybe I should move my company this way. Maybe I should just be involved in everything. Maybe we need to move PMs to product marketing managers."

Is there anything else that's maybe a pro in this approach that might be worth sharing?

Yeah, I mean, I think what you need to recognize is which decisions and what part of the company do you have special spikes on, where you have an edge, and where you can help make the best decision.

Then I would argue, as a leader, it is your job to be involved in those decisions. For Brian, he always spiked in product, design, and marketing.

So he was very natural; this is why he was basically the CPO. That's why he was in all those decisions because those were his spikes, and that's where he helped everybody move forward in a certain direction.

I think for founders, you just need to recognize what you spike on, what are the specific things that you have this great insight that other people do not, and immerse yourself in a lot of those decisions.

There are some things that you might need to let go of that are maybe not as important or maybe certain things that you just won't add much to the conversation. You have someone you trust who's going to uphold a certain quality bar or whatever.

So it's just being thoughtful about where you spend your time and leverage your strengths, basically.

Final question along these lines, very specifically around this whole product marketing manager move. To me, it feels like mostly a rebrand of PM with some marketing work.

In my eyes, PMs already should be doing marketing and thinking about adoption and growth and all these things. So I'm curious, just your take: do you think this is like the future for PMs in general? Do you think this is just a funny thing that every B2B is trying, and it doesn't really make a big difference?

I kind of felt like, and I was reading about this in the news when it blew up, it felt a little overblown to me, to be honest. 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.

I would say the rebranding of product manager 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.

It highlighted the importance of marketing, or maybe it just wasn't as highlighted before, but it was already happening at the company.

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.

There's a function that does that, and your job is a lot more user-centric, thinking through how to tell the world about what you're building. So it was a welcome change broadly.

Now, does that apply to every company, and do PMs do things this exact way? No, it depends.

I think it's actually challenging to find product managers who are also really good marketers. I think it's actually a rare skill set. The art of marketing and the art of conveying what you're building in a compelling way to people is a craft on its own, and you have to build that over time.

There are many product managers that haven't exercised that craft, and of course, they can't just immediately snap their fingers and become good at it. It takes years to learn that skill.

So it kind of, again, depends on the people, it depends on the organization. There's no blanket statement in my opinion where it's like PMM is the way or PM plus PMM is the way. It depends.

Just to clarify, the function you mentioned that kind of took off some of the load of PM is program management. I think it is program management, yes.

They basically took on timelines, staying on top of priorities, and kind of the project manager part of the PM role. Exactly.

Awesome. If you think about it this way, it's actually like the best version of the product management function, not dealing with project management and thinking about the product, the experience, the launch, the marketing, growth.

Yeah, I mean, we had many product managers internally always say, "Oh, we feel like we're doing very tactical work. We want to be much more strategic." Boom! This change actually makes the job significantly more strategic.

Yeah, if you weren't doing that already. Awesome. Okay, I'm glad we spent time on that.

One last question before we get to a very exciting lightning round. We've talked about so many things that have gone really well. You, an incredibly successful leader, person, PM, you've worked on so many successful projects.

All these skills you've worked on that have been really helpful to you that we've been talking about, I want to take us to failure corner. I'm curious if there's a story of failure that you could share where you failed at some point in your career and what that was, and how that impacted you, how that helped you potentially in your career.

I failed a lot. Like we've talked about the positives, but there were also, on my journey, a lot of humbling moments. I still have them—lots of failure.

I would say the one moment I remember was probably in 2018. This was at Airbnb. It was a pretty dark time for me, and I felt overworked, overwhelmed, and I just wasn't a happy person.

This was a time where we were still scaling very, very quickly, and I just felt like I wasn't keeping up as much as I was in maybe the earlier days. I remember thinking to myself, "Oh my God, am I going to tap out in 2018? Is this it for me?"

It was just hard for me because I was also a perfectionist. I wanted to help as much as I could. I had great ambitions and dreams, thinking, "I'm going to keep going with Airbnb for a very long time."

I think in that moment, I kind of hit rock bottom at some point. I actually remember, during that time, realizing that so much of my identity was tied to Airbnb and my job that I had trouble separating myself as a human being from my work.

It was just realizing that was tough. I lost friends, I lost a lot of relationships, and I lost many of my hobbies. I didn't spend as much time as I wanted to with my family and my parents.

At some point, I was just like, "You know, I think in order for me to be a better leader, I just need to be a much more balanced human being." Ironically, that's where I started spending less time on work, and I became way more effective because I was just more centered as a person.

I reached out to people I lost touch with. I spent much more time with my wife and my parents. I started gaming again and all the little hobbies that I lost along the way.

It just made me happier, and because I was happier, I felt like every hour as a result was much more impactful at the end of the day.

So yeah, that's one thing that I think about quite a bit. You can't just pour your heart and soul into something. It is very fulfilling, but you also have to think about how to balance yourself as a person.

If you lose sight of everything else in your life, it's the recipe for disaster. I appreciate you being really real with these. A lot of people just share something that's not as real, and so I appreciate you doing that.

I love the advice of if you're going through a really hard time right now and you're feeling burnt out and sad about your career, maybe just do less and lean into your personal life more, and that will help you be more successful in both.

Yeah, you got to find joy in the little things again. If you don't find joy in little things, I just 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.

I love that. 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.

No, I mean, I'm deeply thankful for the experiences that I've had. I've learned so much. I think, you know, I look back, and there are definitely many lessons, but let's also be real: a lot of it is luck. A lot of stuff just happens, and it happens to go your way.

So when things are hard, the one thing that I just want to maybe share is don't be too hard on yourself and cut yourself some slack. 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. That's all you can really do.

Amazing advice. This might come up again in our lightning round. With that, Vlad, we've reached our very exciting lightning round. Are you ready?

Yeah, let's do it!

Ding ding ding! First question: what are two or three books that you recommend most to other people?

So I love sci-fi. Red Rising was one of my favorite books, and then the Silo series—highly, highly recommend.

What do you think of the TV show version of the Silo series?

What's that?

There's a TV show of the Silo series. Read the book, though. I would like to watch it after you read the book. I always think reading the book is way better.

I agree. I don't know if you actually watched the show, but it's a completely different story. They don't... it's like 90% just a whole new story. I don't know what's going on there. Movies are crazy.

Amazing. Okay, do you have a favorite recent movie or TV show that you really enjoyed?

There's a show that I've enjoyed for a very long part of my life. It's called Survivor. If you've heard of it, probably everyone has heard of Survivor at this point. The show is not dying; it is actually very fun to watch, and there's a new twist every single season.

So I probably watched, I think, like 35 seasons or so.

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, so I gotta find out.

Okay, if I can nominate you for Survivor, I'll find a way, as long as you don't die!

Next question: do you have a favorite product that you've recently discovered that you really enjoy?

So one is actually a product that I cannot live without. I discovered 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.

I love that you use it for gaming and not for crypto—just chatting with players and actually hanging out.

Yeah, love Discord. The product that I recently got introduced to is a game. It's actually a pseudo-board game called Gobbler. It's an advanced version of tic-tac-toe, and so my four-and-a-half-year-old daughter and I play this before bedtime every single day.

She just started schooling me at tic-tac-toe, so I needed to upgrade. Gobbler, if you haven't played it, adds a new dimension where pieces can gobble other pieces, almost like playing in 3D a little bit. It is super fun to play.

Wow! It's funny that she was schooling you at tic-tac-toe, which, to my understanding, you just tie all the time. 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, or share with friends or family in your life?

You never know, and it's a very simple motto. What that means to me is even when there are things with low probability, shoot your shot, take a chance, take a leap. Sometimes you're going to be surprised at how things turn out.

Beautiful. Final question: a tradition that we have is to ask new folks for a fun fact about themselves, which is always a hard question on the spot, but I'm going to ask you anyway. Is there a fun fact about yourself that would be fun to share?

Well, I kind of shared maybe a little bit of it. I absolutely love Survivor, and I have tried to get on Survivor multiple times. It is actually my dream to get on that show.

So if anyone out there watching who happens to cast for Survivor, I am here! I am available, and I will probably not do very well, but maybe I'll be entertaining.

I don't know.

This is your casting video right here!

This is it!

All right, Survivor people, let's get Vlad on! I think you would kill it. I could see all the skills we've talked about would be incredibly useful.

Let him near the fire!

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

So I'm really happy that we did this. Two final questions: where can folks find you online, and who would you want to reach out to you? What kind of folks are you working with these days?

Then finally, how can listeners be useful to you?

Hit me up if you want to chat on LinkedIn. I'll respond, and we can grab a coffee or Zoom or something. I mean, I'm an investor now, and I love spending time with early-stage founders.

A lot of those early-stage founders actually happen to be product managers at some point in their career, so I just love chatting with folks about the problems they're facing or the ideas they have when they're thinking about starting a company.

So yeah, if you're tinkering with cool things, hit me up. I would love to chat.

Is there a segment of startups you're most focused on, just for folks to know?

I bet on people. For me, that was always one of my learnings. I love meeting people that take me into a whole new dimension that I didn't even think was possible.

Now, I do love consumer because a lot of that is my background, so I try to focus on consumer. But at the end of the day, I'm focused on people, and I go into many different directions where people are.

Awesome! All right, and how can listeners be useful to you?

If you want to chat, hit me up!

Cool! Help you find really cool startup opportunities to invest in?

Yeah, yeah, yeah!

Thank you, Lenny!

Thank you so much! This was super fun.

Thank you for having me on!

It's absolutely my pleasure. Thank you, Vlad, and bye everyone!

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

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