20 Product: The No 1 Metric You Need To Look at When Building Product | Why the Best in Product Have No Domain Experience | Why You Should Not Hire From Incumbents & The Difference Between Good vs Great PMs with David Lieb, Visiting Group Partner @ Y Comb

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos, which he has led with immense success for the last 9 years. In the last few weeks, David announced his latest move, to join Y Combinator, one of the world's leading accelerators as a Visiting Group Partner. If that was not enough, David also has a stellar angel portfolio with the likes of Rippling, Flexport, Tally, Maven and many more. In Today's Episode with David Lieb We Discuss: 1.) Entry into Product: How did an idea at business school turn into Bump and ultimately the creation of Google Photos? What are the single biggest mistakes David made with the early Bump product? What does David know now that he wishes he had known at the start of Bump? 2.) Scaling the Team Alongside the Product: What is product-market fit to David? What is it not? What are the single biggest mistakes founders make when they think they have it? What should founders do first and most importantly, when they do have it? Why does David believe individual user data is more important than relying on data? 3.) Product: Art or Science: Why does the description we have for product managers need to change? How does David determine when to act on customer feedback vs stick to the current product plan? What is the right way to do customer discovery? What questions are best to ask? Where do founders make the biggest mistakes in customer discovery? Ultimately, is product more art or science? Is this changing with ever-increasing data? 4.) Product: The Process: How does David conduct product reviews? What are the biggest mistakes founders and product leaders make when managing product reviews? Who is invited? Who sets the agenda? Who determines who is accountable for what? How do product reviews change in a world of Zoom? What is better? What is worse? What can product leaders do to build culture in remote worlds? How can product leaders make everyone feel safe and comfortable to share how they feel, regardless of seniority, in product reviews? Items Mentioned in Today's Episode: David's Best Performing Investment: Flexport

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back. This is 20 Product with me, Harry Stebbings. This is the monthly episode where we sit down with the best product leaders in the world to discuss scaling products, the teams around them, what works and what does not. And I've wanted to have this guest on the show for a long time. Following this guest's very recent move to become a partner at Y Combinator, Paul Graham tweeted an incredible tweet about them, saying they are both formidable and benevolent. I love that as a description. And I'm so thrilled to welcome with that David Lieb, one of the product OGs of the last decade. As the founder of Bump, David pioneered how over 150 million people use and share data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos, which he's led with immense success for the last nine years.

• 0:44Harry Stebbings?

  And in the last few weeks, as I mentioned, David announced his latest move to join Y Combinator, one of the world's leading accelerators as a partner. If that wasn't enough, David's also a stellar angel investor with investments in the likes of Rippling, Flexport, Tally, Maven and many more incredible companies. But before we dive into the show's day, we need to talk about the game-changing tool that is Miro. Are you and your product team still going from tab to tab, tool to tool, looking for the most accurate information but losing out on brilliant ideas? Well, you may not just be a PM in that case. I'm a podcast host and I need to constantly be balancing the deliverables from multiple different stakeholders, whether it's my team locking down interviews, voting on potential topics for future shows or directing feedback from guests.

• 1:27Harry Stebbings?

  I need to manage a show like a PM manages a product and loss of information causes real inefficiency. So I keep track of it all using Miro, the collaborative visual whiteboard that brings your product team's great work together in one place online. Miro acts as this infinite canvas where ideas and projects can be shared across the team and across the tools they use. So how do I use Miro as a podcaster with every episode? Well, with every show that we do, we create a new Miro board. My team takes 10 reference calls before each episode for every guest and they compile all of their call notes on a Miro whiteboard. Then I can jump into it, see all the call notes in one place and then write the schedule for the show with all of them in front of me, easy to access and at the same time

• 2:10Harry Stebbings?

  Total game changer and that's why over a million new users join Miro every month. Get started today with your first three boards absolutely free. That's miro.com/20vc. That's miro.com/20vc. And speaking of products like Miro that really change the game. If you are anything like me, you're always travelling. Then you need NordVPN. NordVPN is the best VPN if you're looking for peace of mind when on public wifi. It allows you to securely access personal information or work files, encrypt your internet connection and keep your browsing history and online identity private. Enjoy online privacy and security with NordVPN. And even better, their newest feature even protects you from ads, trackers and malware.

• 2:52Harry Stebbings?

  Grab your exclusive NordVPN deal by going to nordvpn.com/20vc to get a huge discount off your NordVPN plan plus one additional month for free. It's completely risk free with Nord's 30 day money back guarantee. And last but not least, you have to check out builder.ai. They make building software so easy that anyone can do it. If you have a vision, you can build it with builder.ai. And one of my favourite products of theirs is Studio. I always think the number one reason people fail is they do not start. And Studio is the perfect tool for when you need an MVP fast. And when I say fast, you can build simple, beautiful native apps in less than one day. Don't just take my word for it though.

• 3:35Harry Stebbings?

  Leading brands like Pepsi, BBC, Fujitsu, all love and use the product. Head over to builder.ai to find out more. But now I'm so excited to hand over to the one and only David Lee, partner at Y Combinator.

• 3:53Speaker 01

  You have now arrived at your destination.

• 3:56Harry Stebbings?

  Dave, I'm so excited for this. I feel like I know you so well. I spoke to so many people on your team from Juan to Jamie to James. So thank you so much for joining me today.

• 4:05Speaker 02

  You bet, it's my pleasure.

• 4:06Harry Stebbings?

  Now, I want to start, you know, you've had the most incredible tenure with Google. Tell me, how did you make your way into the world of startups and products and come to lead Google Photos for the last seven or eight years?

• 4:17Speaker 02

  Yeah, I would say it's largely accidental is the true answer. I was an engineer by training in school and I worked as an engineer at Texas Instruments early in my career. I think like a lot of smart engineers of my era, the thing you do next is you leave and you go to business school to learn quote business, which I did. And the first week of business school, I was faced with a personal problem, which was I was meeting all of my new classmates and we were trying to share our phone numbers with each other. And I just would like five times a day, I would like type in somebody's phone number and then ask them how to spell their name and then I would call them and they would like dismiss the call and add my number to their address book. And it was right when the iPhone had come out and they had just opened up the App Store. And I thought like, oh, why isn't anybody solve this problem? Like this should be a solved

• 4:59Speaker 02

  problem in the world. Maybe I can make a side app that would like make it work. So I started building that as kind of like a side project in school with the aspiration of like maybe making enough money to pay for my business school, which would like be like one in the order of tens of thousands of dollars. We launched it and people started using it like way more than we thought. And so we decided like, okay, we should work on it next weekend, too. And we said that, you know, for 10 successive weekends. And then we decided, okay, well, maybe we should like try to make this bigger than what we thought it could be. And we had heard of this thing called Y Combinator, which was like this nascent startup incubator thing. And we applied to it on a whim and we got in and we came out to California that summer to like work on our startup. And then we never went back to school. And then, of course, like we pivoted a few times with Bump and

• 5:41Speaker 02

  ultimately decided to work on photo sharing and then got acquired by Google and then I was there for nine years.

• 5:47Harry Stebbings?

  There's bits of your career which I want to kind of unpack, but I do have to ask, and Juan asked this one as well. He said, what are the ones two biggest lessons for you from your time founding Bump and the transition to Google Photos?

• 5:57Speaker 02

  For startups, like when you've done a startup, you realize that kind of the definition of a startup is you start with absolutely nothing and you have this big vision for like what it could be one day in the future. But to get from there to there requires like you to do basically everything, at least at the very beginning. So the number one takeaway from the startup is just this like ownership mentality that you have, which is like, we have nothing, there's no one else, it's just me, I must make it work somehow. I must do everything that's required. So in the early days of Bump, like myself and my two co-founders, we wrote all the code, we did all the designs, we thought about all the marketing Strategy or hacks or ploys we could use to like get anybody to hear about it. Every PR, every press interview, like that was all just us. We had to learn it on our own.

• 6:38Speaker 02

  And I think that's a skill, this like generalist skill that generally people don't have at big companies. Cause they don't need to. There's experts at big companies that do everything. I think magic happens when you bring all that stuff together in a very small number of people's heads. And they can do like pretty amazing things.

• 6:53Harry Stebbings?

  Do you know what I find the hardest thing? Letting go, which is like moving from founder led sales to team led sales. And I still have this today while I might know I can do it better than anyone else. I may be able to do it better than anyone else. I didn't mean that arrogantly, but I still shouldn't be doing it.

• 7:07Speaker 02

  Yeah.

• 7:08Harry Stebbings?

  How many advice on that for me?

• 7:10Speaker 02

  Yeah, you certainly need to make that trade off at some point, but I think most founders do it too early. They think like, oh, we have a product that like shows some glimmers of, you know, product market fit. Let's go hire a sales team and that will be the thing that makes us succeed. Usually that's the wrong answer. Like usually you are the person who knows the product and the customer the best. And so you should probably be the one doing all of those important jobs for longer than you think it's reasonable. There should be a point, I think, where you're like, I can't believe I'm spending all of my time doing this. If only I could spend my time on these other really important things, but I can't, because this is still the most important thing. Then it's the time to like go bring somebody in who really knows what they're doing and can shadow you and and kind of take it from where you are right now and take it further.

• 7:50Harry Stebbings?

  You have full license to end this call with this next question, but you mentioned some notion of product market fit. There's so many different notions and I have so many founders I was then like, I don't fucking know if I've got it or not. Some people are somewhat disappointed, some are not disappointed. I don't know. How do you advise a founder to know when something is hitting and there is the first signs of product market fit?

• 8:13Speaker 02

  If you don't know if you've got it or not, you don't is the simplest answer, right? It is a thing where something clicks, people just use your product or demand your product so much more than you could have ever fathomed. That is generally when you've got some initial glimmers of product market fit. You have no time in your day to do anything but satisfy those customers. Whether it's keeping your servers up, if you're a software company, whether it's like fielding inbound queries from customers who really have heard about your thing and they really, really need it. Those are the signs that you probably have some glimmers of product market fit. But I think most of the time. People find I built something that has some resonance with some small set of people. And oh, I must have product market fit now.

• 8:54Speaker 02

  And generally, you might be on the right track, but you probably don't have it if it's unclear whether you've got it or not.

• 8:59Harry Stebbings?

  I love the way I have these articulate schedules and then I just get too interested. What were the top one or two decisions that you think made Google Photos the success that it was?

• 9:08Speaker 02

  Probably the number one, the meta decision that we made early on was around what our mission would be. And I think this is a thing that often gets overlooked or not enough time is spent in bigger companies. It's probably more critical at small companies that you figure this out. But we decided that we would have a very clear mission, which was to be the home of the world's memories. And that was like the only thing we were going to work on. And we were quite explicit at the beginning about what things we would not go into. And we said internally at Google, like, we're not going to build a social tool. This isn't a social network. It's about storing your life's memories. I think by being really clear about that mission early on, it did a few things for us that I think propagate to this day now 10 years later. One is it really helped us select who should be on the team and who shouldn't be on the team. We kind of spun the team out of the Google Plus team.

• 9:52Speaker 02

  And there were a bunch of folks who signed up to build social, right? They were very excited about social and that's awesome. But we were very clear, like, that's not what we're doing. And those folks decided to move on. And I think it was great for them and great for us. And it also helped us attract the right people to the team. We said, if you're not like all in on this mission, if you don't want to spend the next N years of your life, like solving this problem in the world, you shouldn't come work on this team. And I think that really set us up for success. And to this day, like everybody on the team knows that mission by heart.

• 10:18Harry Stebbings?

  Do you think incumbent products, when you look across the incumbent set? Do you think their new product suites and new products themselves, teams, do they have those missions, do you think?

• 10:27Speaker 02

  I think at best they have something written down. I really doubt they think about it on a daily basis and reaffirm with everybody on the team, like, this is our mission. Here's why we're doing it. Here's why you woke up today and came to work. And we just decided we would really focus on that.

• 10:42Harry Stebbings?

  When I spoke to so many of your team, what really shone through was just what a incredibly loyal and really bought in Googler you are. And I think the thing that shocked me and we chatted about it a little bit before the show is why did you decide to leave Google most recently? And what was behind that thinking?

• 10:58Speaker 02

  I had been at Google nine years, I left last week, and I would say the trigger for me finally. Last year I was diagnosed with surprise leukemia and so I was out for a year doing chemo and fighting that. And so the team, like all the folks who reported up to me, like on a random Thursday, they just had nobody anymore. They had to step up and do it all themselves. And for an entire year, they did it and they did it great. And so when I came back, it was kind of like, oh, it works. Like, it's okay without me. It made me feel good about being able to one day step away. And then I think the second thing that changed is, you know, I had like a near death experience. There was a random Thursday, the first night I went into the hospital, I was in the ER. And I thought there was a very good chance I would die. And when I got through that quite difficult year, I just decided like, wow, life is indeed short.

• 11:42Speaker 02

  Like everyone tells you, life is short, do what you care about. But I've like actually felt it now. And I decided like I should do what I really love doing. And for me, I love startups. I love helping founders. I loved being a founder when I was one. And I just wanted to do that with all of my time. So I decided to leave and join Y C.

• 11:58Harry Stebbings?

  You mentioned the team being brilliantly self sustaining without you. I spoke to so many of them before the show. And they mentioned that you are a product visionary. Literally, everyone said you're a product visionary. And I thought that was a good entry point because there's often this tension between art and science and product. So as a starting point, is product more art than science? How do you answer that one?

• 12:16Speaker 02

  What a question. My opinion is it's more art than science. And so let me explain maybe why I believe that. If you look at truly great products, pick any product that you use that you're like, that product is just really well done. Generally, there are a very small set of people behind that product that really love it, that obsess over every single thing about it. It could be one person, it could be a team of five people, but usually it's a quite small number of people who make that thing great. And how do they make it great? It's because they love it. They love the customer. Maybe they are the customer, maybe the customer is their friend or their family member, and they just want to make something great for that person. That is the core of almost all great products. And I think in order to do that, you have to treat it as more of an art. You have to put yourself into it. You have to obsess.

• 13:00Speaker 02

  And you can't do that with science. Like, you can't just do experiments. You have to understand the customer and really feel what they feel. And I think that is much more art than science.

• 13:09Harry Stebbings?

  But I'm working with early-stage founders. Do you have a preference for founders that do have that? I felt the pain. I was working at X company and I did it. Versus people who are actually more objective and analytical. And I often hear this, where actually we can make analytical decisions with a lot less irrational guts.

• 13:27Speaker 02

  Sure.

• 13:27Harry Stebbings?

  Because we are not feeling the pain.

• 13:29Speaker 02

  Sure. I agree with both of those statements. Like, I think if you're being very analytical, you will avoid large mistakes. Because your data or your analytics will tell you like what you should do and what you should not do. But what they also will avoid is the like big unexpected wins. If you think of maybe in like a scientific way, using science bounds your variance of your outcomes. It makes sure you don't like totally blow it, but it also makes sure that you don't like find something that no one else would have found. Because you would never try it. And that's where I think doing it more of an art is the way that you get those big upside outcomes. Now, of course, you also get big downside outcomes, so you have to be okay with that. But as a startup founder, as an example, like what are you in the business of? You're in the business of finding big upside anomalies that you found that the rest of the world hadn't yet found.

• 14:12Speaker 02

  And so that's why I think going with your gut and understanding the customer personally. And then building what you think they need, whether it's what they're saying or not, usually it's not what they're saying. That's the way you find these big upside outcomes.

• 14:23Harry Stebbings?

  Do you find serial founders or older founders more aligned to that gut instinct? Willingness to have the high variables versus maybe more younger insecure who don't want the rich?

• 14:35Speaker 02

  You know, repeat founders often, they know more about how the game works. And so they alter their behavior to some extent, both for the good but also for the bad. They don't let themselves run crazy on some wild idea that everyone around them thinks is stupid. They generally feel some peer pressure to not do that. Whereas very young founders, like naive founders to some extent, they will go off on crazy pursuits. Because they think it's the right thing to do. And everyone around them will be like, I don't know what that kid is doing. That's. Insane. And then they build something that people really love. And so I think to some extent, as a startup founder, you want to be a little irrational when it comes to how you solve your problem. But the thing you gotta be very rational about is, is there a person that actually has some problem that I can solve and understanding that customer very deeply?

• 15:18Harry Stebbings?

  Jamie Aspinall on your team said, when gut instinct is the primary tool, Dave is the master. He wins. My question to you is like, how do you think about using your own gut instinct? How do you think about downside protection? Given that, you know, you are willing to have the variables and how do you think about that?

• 15:34Speaker 02

  Yeah. So people often refer to like using your gut or trusting your gut. And I think often they say it in kind of like a derogatory way. Or like, oh, your gut is just like this thing on a whim that you should be careful about. I have a different view. I think your gut is the world's most sophisticated machine learning model ever created. It is like the best supercomputer we've got and there's billions of them on the planet. And they've been trained over like tens of thousands of years with tons of training data. The people who wrote the code, there's like generations of people before you that have been tweaking this code for you. And it's now yours. You can now use it. What an amazing thing. And I think we discount it, but instead we should leverage it. My God, what I try to do is put as many inputs into this machine learning model that you can.

• 16:16Speaker 02

  Learn as much as you can about your customer, try as many experiments as possible, put it all into your brain. And then see what your gut says you should do next. And I think that is actually like quite analytical way to approach the world. You're just using a tool that people aren't used to using.

• 16:30Harry Stebbings?

  I'm so, I love that as a statement as most sophisticated machine learning model. But it kind of goes in the face of other things that I heard about you, which is that you're an incredible perfectionist. You're really granular and so in the detail, but that kind of goes against the fast iteration, learn, learn, learn. How do you think about the balance between like speed of ship, learn, learn, learn, but also ensuring quality and perfection?

• 16:53Speaker 02

  Yeah, I think it really depends on your context. So like in the context of Google Photos. At Google, we were planning to launch this new product, Google Photos. We kind of knew that like the world would hear about it. We would get some trial users on day one, right? So we decided in that context, we better make that product pretty great for those people because otherwise they're going to. Try it and they're gonna be disappointed, especially so because the product's goal was to store the most important digital asset that you have, which is like your life's memories. So in that context, we decided the bar's gotta be reasonably high, at least for the core parts of the product that convey that trust to people. As an example, the main grid of Google Photos, like you're scrolling your photos and it has all the squares with all your photos. We, very early on, this maybe is an answer to your previous question, decided that thing

• 17:37Speaker 02

  has to be very fast, very reliable, it has to work in all network conditions, there can be like no instance where you don't see your child's photo. And that was really hard, like from a technical perspective, we had to do a lot of things to make that true. And it took us months to get that right, but I think that was the right trade off for that context. Now, switching gears to like the beginning of Bump, let's say, that was another thing that I worked on. The first version of Bump, I look at it and I'm like very embarrassed by it. It was horrible, it was terribly designed, like who designed it? Like somebody who's never done a design before? Yes, me. And I think you just gotta understand your context and what risks you're willing to take. For most startups, the answer is you should probably ship something and learn something from someone and then you can make it better.

• 18:19Speaker 02

  If you're a big company, you might need to make something like quite good before you wanna launch it.

• 18:24Harry Stebbings?

  In terms of like learning and making it better, I think the really hard thing is often the people who you hear feedback from are the most vocal and they may not be representative of the entire customer base. How do you think about the feedback to ingest and act on versus the feedback to always listen to but not necessarily act on?

• 18:42Speaker 02

  I think there's two bits in there. One bit is who are you talking to? And are they representative of your desired user base in the future? It's really great if the answer is you are representative of your desired user base. The second bit though is like what are they saying to you and what are you taking away from it? I think too often people listen to what customers say and they think like, oh, we better just go build the solution that they said, right? They, I don't, I'm confused by this screen, why don't you put this button there? And they just go do that. And I think that's the total wrong way to do it. You should listen to all the words that they say and all the expressions they make on their face and every piece of data you can when you're talking to a customer and then use that to understand why? Why did they say that to me? Are they really confused by? Or maybe this thing like doesn't matter to them and they haven't like put in any effort to understand it.

• 19:26Speaker 02

  Like maybe I'm just not solving a big enough problem for them. So you have to understand the why behind what they're saying, not what they're saying.

• 19:32Harry Stebbings?

  How do you get to that layer deeper? I find customer discovery one of the hardest things. Often people ask leading questions. What's the right way to get the truth from that process?

• 19:41Speaker 02

  It is some form of repeatedly asking why? Why do you care about that? In what context do you do this? When was the last time that you had this problem? What did you do without our product when you had this problem? These are the types of questions that give you the context to really understand what's going on for that person. Because I think another thing that we forget about when we're being PMs is these are real human beings with real lives. Like they had to go take their kid to school in the morning and then they had to come home and like figure out what they're going to eat for lunch. And we often like forget about all that and just ask like very pointed questions. Like when you see this screen, what do you think? And the answer might depend on what they did this morning, trying to get their kid out the door to school. And so I think we gotta go a lot deeper on who these people are and what are their problems holistically? To understand how your product can solve something in their life.

• 20:25Harry Stebbings?

  When does one rely on that gut intuition, more human incentive versus let's look at the numbers? Let's look at the data and let's go to the cohorts. I'm sure there's a time for both. When is the time for data?

• 20:37Speaker 02

  Data is a fantastic tool. It tells you a lot of information all at once that can be very useful directionally about where to go. I dislike most aggregated statistics. Yesterday, we had this many users upload a photo or there were this many comments on this post yesterday. Because they can be very misleading about what's actually happening for individual users. I much prefer looking at data around individual users in a large scale way. So like, let me explain what I'm talking about. You mentioned cohort graphs. Like I think that's the number one thing you should look at when you're building a new product is what is your cohort retention curve look like? If a hundred people start using your product today, who's using it tomorrow? Who's using it the next day? Who's using it the next day? And what you want to find is those cohort graphs get flat. You want the same set of people eventually to keep using it over time.

• 21:22Speaker 02

  Once the other folks who've decided it's not for you have left. Because that tells you about individual users. The other tool that I really like, and there's a variety of-

• 21:30Harry Stebbings?

  Can I just dive in that? Sorry, I'm- I'm too interested while you're on that point. When you said about that cohort retention graph, and you said about the people who decided it wasn't for you left. When you think about the like total audience population that makes that graph, some could say, well, they are not qualified leads. And so they shouldn't be in that cohort anyway. And so actually, you're naturally going to have a lower retention rate because you have unqualified leads. Should you have unqualified leads in your retention cohorts, or should it only be the most qualified? And then naturally, you can kind of alter the data to fit the way you want it to be.

• 22:00Speaker 02

  Well, yeah, I certainly see people do this where they say the population isn't anyone who signed up for our product. It's only people who've like gone past some part of the funnel to qualify them as like, you know, real users. I think that's fine. Inevitably, you're going to have some folks in your funnel that should not be your customer. You think they shouldn't be your customer and they think so too. And so it's okay for that graph to have like a quite steep step down in the first time period. But what you want to find is that after that, for whatever the granularity of your time period for your product is, it might be a daily use type of product. It might be a weekly use product. It might be an annual product. Who knows? You want to see in that time period, the people who did stick with it and understand it, they are satisfied and they keep using it over time. And potentially they use it more as the product gets better, or more people in the world use it, or whatever network effect might exist happens.

• 22:45Harry Stebbings?

  What do you think are the biggest mistakes that founders make when they construct and then examine their cohorts and retentions?

• 22:52Speaker 02

  Number one mistake is they don't do it, to be honest. Like so many companies I talk to, I ask like, what's your cohort retention curve look like? And they don't know. Do I blame them? No, because I did exactly the same thing when I was a founder. We were raising money for Bump. We were like sitting in the Sequoia office and somebody asked like, what's your cohort retention look like? And I'm like, it's good. And then after the meeting, I like went and looked it up and I'm like, oh shit, I have no idea what they were talking about. Like I should know these things.

• 23:16Harry Stebbings?

  So for me, I always look at 30 day. I find like anything below 30 day actually not indicative of like a true habit forming behavior. And it is very different depending on product. I completely understand and know. But say for a product like Google Photos or for Be Real, which I'm invested in, 30 days is really where I gain. And same for gaming as well. Is that the same for you, number one? And then when you think about good in the consumer social photo. Utility space, which is aligned enough. What is good? I find founders often, I feel really sorry for them. They don't know what good is.

• 23:49Speaker 02

  For a product like Google Photos, let's say, I think a good user of Google Photos is using it almost every day. Most days of the week, you should be doing something with your photo library. And so we would look at cohort retention with either a daily or a weekly time period. You count as a user if you used it in the last seven days. You don't count if you didn't use it in the last seven days. I think that is the best way to see like what's actually going on. What you normally find, however, is people want to show charts that look good. So they show like number of users in the last thirty days. This is our Mao, monthly active users. It makes you feel great, but like, did those users really love your product in that month that you measured it? Like, maybe, but I bet a huge chunk of them used it for one accidental reason or another and then didn't actually want to use it again. This is a fun anecdote from Bump.

• 24:33Speaker 02

  In the Bump kind of heyday, we had one hundred fifty million installs on phones. When the market for phones was only a billion phones in the world. So we were on like twenty percent of all phones in the world. We were a big blue icon on the home screen. And what we found in our data, we saw a huge number of sessions were less than one second long. And we were like, how the heck, why would you open Bump for less than one second? Like, it's a thing you have to intentionally decide to do. You have to bump another person. There has to be a person there with you. And what we found, when we then examined our own usage, we were like, you know, sometimes I accidentally open the Bump app because it's blue. And I was trying to open the Facebook app because it's blue. And we then looked at our data and we're like, that's what it is. You have a one in a hundred chance of accidentally tapping the wrong icon. Multiply that by one hundred fifty million users, like, you're gonna get some users doing that.

• 25:18Speaker 02

  So you gotta be really careful with aggregate data like this. We thought we were like hot shit because everybody's using our app. But turns out like twenty percent of the time, it was accident.

• 25:27Harry Stebbings?

  What is good retention numbers? Is it thirty percent? I remember Jeremy Liu told me, I think it was thirty six percent snap pad on thirty day retention. What is good?

• 25:35Speaker 02

  All that matters to me is that your graph gets flat. It can get flat at five percent of your initial cohort of users. So long as that five percent is flat and consistent and valuable. I remember at one point seeing a curve of Airbnb's either thirty or maybe ninety day period cohort retention. And it's pretty steep and it gets pretty low, but it's flat. And each time they use it, Airbnb makes a hundred dollars. So that's totally great. It's a hundred billion dollar company. So you've got to understand the context of like, what are those people doing? How frequently are they doing it? And how valuable is it to you and to them to use your product?

• 26:11Harry Stebbings?

  Are there any other mistakes that founders make? Number one, they don't set them up and they don't actually have the foundations. Are there any others? They have the wrong kind of, they have like attraction metrics like M A Es, which

• 26:21Speaker 02

  Right, things that make you feel good, but actually

• 26:22Harry Stebbings?

  Yeah, everything else. If I'm a Y C company and I'm coming to you.

• 26:25Speaker 02

  Well, I would say like another meta problem is over reliance on the graphs and the numbers. Like you can look at graphs and you can slice and dice and make some like very interesting observation, but it doesn't tell you why. It just tells you what is true. And there are many reasons behind the same truth in the world. And they might lead you in completely different directions about what to do next in your product. And so I think it's very naive to look at some graph and then decide your product roadmap based on some graph that you make. It might inform areas of exploration, but it should not tell you what to do. Instead, you should go talk to users. Ask them, hey, have you ever opened bump for like a second and not used it?

• 27:02Speaker 02

  And they may tell you like, oh yeah, sometimes I accidentally open it. Whoops, sorry. And then aha, you've like learned something real in the world as opposed to the effect of something real in the world.

• 27:11Harry Stebbings?

  When you're a startup, often you are told that actually the logoed people from Google or Salesforce or any of these places, they are too in the metrics. They're not close enough to customers because they've been with these incumbents too long. If you're advising again me as a Y C founder, early stage, would you say that's fair and you shouldn't get these people to join your team because they're not used to the early startup days? Or would you say actually?

• 27:34Speaker 02

  I think you should be careful. There's a set of people at all these big companies that I think are really great. I've tried to hire them all. And they get it and they really want to do all the things needed to be successful. But there's another set of people at those companies that are there for different reasons. They're there for their career. They're there because they want a good paycheck. They're there for the status that these companies bring. They've never had to solve these problems themselves. This is a double edged sword that you get at some of these big companies is there's an expert on the team for every possible thing you could imagine. You have a legal issue in Estonia? Great. We'll go bring in the Estonian lawyer and he'll like tell you what what's going on there.

• 28:11Speaker 02

  The problem is none of those experts is responsible for the holistic success of your product. Without that, who really feels ownership to make your thing great? Is it the product? Lead, is it the design lead, is it the engineering lead? Who really feels like their personal credibility is on the line to make this product successful? And I think that is a common failure mode for large companies is you lose that at some scale and at some size. It scares me, it worries me for a lot of these big companies.

• 28:37Harry Stebbings?

  Well, we spoke about kind of obsession and sweating the detail. Again, so many people said this about you, even to the fact that like on your last day at lunch, apparently, you were like moaning about a feature that you still hate. I heard this, I did my research. And my question to you is, how do you create a culture of product obsession and granularity within your team?

• 28:57Speaker 02

  I think you just have to show it yourself. It has to be authentic, like you have to personally be obsessed with the success of your product, be obsessed with the product experience, be obsessed with the customer. And then people will see that it's true. And what's great and hard is that it's really hard to fake real obsession. Obsession is a form of love and love is a very hard thing to fake. I would argue like it's probably the hardest thing to fake in the world. You can't just pretend to be obsessed about a thing that you're not actually obsessed about. So step one, it's very simple, work on something that you're obsessed with or you could become obsessed with. Then just let it show, be yourself, be authentic. Like I remember so many times in the early days of Google Photos, I would like walk over with my phone to the engineer who was building the main grid of the iPhone app.

• 29:41Speaker 02

  And I'd sit next to him and I'd be like, this doesn't feel right to me, does it feel right to you? Like, see how when I scroll, there's like a little glitch and I saw it, did you see it? I would record things with my slow mo camera, like on my other phone. I'd record the grid scrolling and then I'd play it back in slow mo for these people. And I'd be like, did you see that little glitch there? By me just doing that, A, the people who didn't like that maybe decided to leave the team. And B, the people who also felt that, but maybe were a little scared to like talk about it, like to raise their hand and say, hey, I'm not sure we're ready to ship this because I'm not, I don't think it's quite good enough yet. It makes that okay. It makes them see like, oh, if the lead here, the person who like started this thing, if he obsesses over this, maybe I can voice my opinion on the things that I'm obsessed about.

• 30:24Speaker 02

  And it creates this culture where everybody is on the same page about success and they're willing to kind of like be themselves and say what. They bring to the table to everyone and that's where magic happens, I think.

• 30:34Harry Stebbings?

  I think fundamentally, you have to have the right product team together is probably one of the most crucial things you can do. I'm an early stage founder, again, NYC, say, seed to series A, okay? You are my mentor. I've never hired a product team before. How do you structure your hiring process for a product team? What is the process?

• 30:52Speaker 02

  Well, if you're early stage, your product team maybe is one person, right? Maybe you're hiring one PM. This is another meta mistake is people think like, I've raised my seed round, I have four million dollars. Like, let's go hire a team of 20 people. That's what I see all my cohort members doing. That's probably the wrong thing to do unless you really have product market fit already. But let's assume things are on fire, like, oh, my God, we've got to build all these things, like, great news. I would say at the early stage, the number one thing I would filter for initially for product people. And product people at an early stage company is a very broad set of skills. Like, you're kind of looking for people who can kind of do anything decently well. I would say the number one thing you're looking for is ambition. People who really want to be part of this thing and want to have it succeed.

• 31:35Speaker 02

  And that is very different than what you might hire for in many other areas or other stages of a company. But ambition at the early stage, you can take a reasonably smart person who has the right ambition and they can do incredible things for you if you give them the right environment.

• 31:50Harry Stebbings?

  They have to have the foundational product talent. So I guess my question to you is, how do I assess that? I'm literally a sales CEO. What's the process for assessing if they're good at product?

• 32:00Speaker 02

  So I would find some products that you think are good and some products that you think are bad. And I would ask them about them. See if they've ever gotten to the point of thinking about why a product they love is great versus why a product that they don't love is bad. And can they explain it to you? Do they have an opinion on it? These are things that are very squishy. It's very hard to like, how would you like write a multiple choice test that would test that? It's very difficult. But these are the things you're looking for because they show that the person has like thought from first principles about why a thing that they see is true in the world is true. And the why is what matters. And the skill of asking why and learning why or figuring out why has the number one skill for building early stage companies. Because that's what you're doing all day long. Why is this working? Why is this not working? How do we do more of the thing that is working?

• 32:44Harry Stebbings?

  When do you think about bringing in CPOs? If we're a scaling company, I often see the transition required. When would you advise founders on now you need a CPO slash head of product, not just jack of all trades?

• 32:54Speaker 02

  Again, most people do this probably too early. So that's like the common theme here. So I made this mistake myself. At Bump, we got to like, maybe it was thirty employees and all of our vanity metric graphs were like going way up. We were feeling really good and I thought our company is gonna need to like figure out our business model eventually. We're gonna need to keep scaling and hiring. I'm gonna have to do more fundraising. I better hire a product lead to take over from me and I'll go focus on those other things. And I did. He was awesome. And then we realized, oh, actually, we have not really solved product market fit. Sure, we have a lot of people who use our product, but like, we can't figure out a way for them to pay us. We can't figure out anybody else in the world who will pay us for access to those users in some way. So really, we don't have product market fit. Whoops.

• 33:37Speaker 02

  And I realized the success or failure of my company actually has to do with what this person I just hired is gonna go figure out for me. Generally, that is a very dangerous place to be, where the founders or the CEO of the company is not working on the most important problem for the company's success. And I just found at some point that I need to be doing that. It's my responsibility for this company to be successful. I better be working on this. And now all of a sudden, we have two people who wanna be top person on product. Dave made a mistake. I was wrong about when to hire this thing and we parted ways and that was the right call for the company and for him, to be honest.

• 34:10Harry Stebbings?

  You said there about kind of the mistake. Annie Pearl from Calendly, CPO at Calendly, said on the show the other day that the biggest mistake that founders make when hiring CPOs is actually they have misaligned expectations. And they bring someone in, but they still kind of wanna own it and they don't really.

• 34:23Speaker 02

  It's exactly that. Yeah, that's the same answer, basically. Yep.

• 34:25Harry Stebbings?

  Do you see that often?

• 34:26Speaker 02

  Oh, for sure. I think the other piece of it is people wanna hire people like them. When you're hiring the top product lead for your team, if you plan to be around for a long time, you probably don't wanna hire someone exactly like you with the same set of skills. So as an example, on Google Photos, when we grew enough to where I needed to hire someone to run the product team, I very explicitly wanted someone who had a complementary set of skills. What are the things that I? I'm uniquely bad at that like the team suffers because I'm bad at those things. Let's find someone who's world class at all of those things and they will like really plug a big gap in our team. That's the way you should do these things unless you're planning to leave. In which case, like you need to hire someone who's has the skill sets to be the singular lead.

• 35:08Harry Stebbings?

  I had Sherry asked Oshie on the show as well and he categorized three different product leaders. He said there's craftsmen and women, there's visionaries and there's operators. And I think the most damaging one that I see is the operators. And what I mean by the operators is the series C professional CPOs. Who come in and put a lot of process in place and actually do very little. And they like talking to other CPOs and they like talking to the board and feeling important. Do you agree with that? How do you prevent getting that operator, which actually just brings process and delays?

• 35:40Speaker 02

  Right, yeah, 100% agree. I would say like the number one failure mode when people hire product leaders is they over index on previous scale. How big of a team have you previously managed? Or tenure, like how long have you been doing this? What experience do you have? Do you have experience in our domain? It turns out that if you're the median PM in the world, you're like middle of the stack, not good, not bad, here's median. If you stay in the game long enough, you will be that person by definition, almost, right? If you last long enough, you will eventually lead a team of 25 PMs. But you're not actually good necessarily, you're median. And it's very dangerous to hire those people. You've heard this saying before, but like A players hire A players and B players hire C players. It's totally true. It happens like literally all the time. I watch it happen.

• 36:23Speaker 02

  Once you hire that B player to be your lead, like bye bye, your team is gone. Like the best people on your team are not going to want to work with that person. So how do you avoid it? I think you gotta retain this ability to be either a craftsman or a visionary, hopefully both. Because those are the people that people want to follow. They want to listen to what they're saying. They want to work with that person. They want to work with the people who want to work with that person. I think it's incredibly valuable. Yet founders. Think I better hire this experienced person who knows how to do this. But turns out they don't actually know how to do it, no more than you do.

• 36:53Harry Stebbings?

  Is there ever a time for an operator when you are a smart sheet or an Anaplan? Or name your kind of quite non creative SaaS enterprise product respectfully?

• 37:04Speaker 02

  Yeah, yeah.

• 37:05Harry Stebbings?

  Is there a time for one?

• 37:06Speaker 02

  Yes, but there still must be a product visionary and a crafts person. You got to have somebody on the team who's doing that role. It's totally fine if that person is the founder CEO or the co-founder who's focusing on product. And if you're hiring an operator to like run your team, which those people are incredibly valuable. You can't really operate at scale without somebody who's good at that. But you should not confuse that with who is the visionary? Who's the person, you know, like leading the charge on what we're going to build next? Who's the person that reinforces the culture that we want at the company day to day? That person must exist. It's fine if it's not the chief product officer. It just needs to be somebody.

• 37:40Harry Stebbings?

  Final one on the hiring process. Do we need to hire people who've built products like the product we're building before? So say if you're doing Google Photos, obviously most aligned, consumer, social, visual, creative, sharing. Or can it be PM from Airtable from you name your SaaS or enterprise company?

• 37:57Speaker 02

  Yeah, in my experience, most of the really strong PMs that have emerged, say, on the Google Photos team, came from backgrounds with no experience in this domain, really at all. In fact, I would probably go so far as to say that it's anti-correlated with the top performers. The top performers tend to come from some strange background. I think one of the folks you talked to on our team joined Google as like a salesperson. And now they're a PM running like a big chunk of Google Photos. And again, I think it gets down to this like self-selection for ambition, like a chip on your shoulder. These people want to prove that they can do this, that they can win. And those people tend to work harder. They tend to like understand the customer more, they go the extra mile. And these are the things that separate success from losing.

• 38:37Harry Stebbings?

  I'm so enjoying this. What's the difference in good and great in those PMs?

• 38:41Speaker 02

  I guess it comes down to two things, the ability to really understand the user very deeply. And then the ability to craft creative solutions to those problems that you find. Those I think are the two core parts of the job of being a PM. On the first one, how do you like understand the user? You've got to be open to. To and willing to go out and make yourself look like a fool, talking to other human beings, understanding how they use your product. Most humans don't like feeling like a fool. Do you? No. Do I? No. But it's

• 39:07Harry Stebbings?

  I've grown very used to it as a VC, so.

• 39:11Speaker 02

  That is how you learn what's happening in the real world is you have to put yourself out there and say, "Hey, guys, I want you to look at my product." And they'll look at it and they'll be like, "Who the heck are you? Like, get out of my face." And that's a tough feeling. It's a feeling of rejection. That's very difficult for people, but you have to be okay with that. And so I think, again, that's why folks who come from non-traditional backgrounds, they've probably had that happen to them quite a bit in their lives, whether they went to some like no-name school and all their peers now at Google, like went to Harvard or Stanford or whatever, they felt that before and they are okay with it. And they're willing to like plow through it. So I think that's a very important skill set. The second piece is knowing enough about how to build a product, the engineering involved, the design involved, like all the pieces that are required to build a great product.

• 39:52Speaker 02

  Knowing enough about that to be the ringleader or the champion, to take the insight from the customer and actually build something that will solve that customer's problems. As an example, in Google Photos, you have to understand enough about how AI works to know like what is conceivable that we could build to solve this customer problem versus what is like inconceivable. We can't, there's no known solution right now. Understanding that and being able to kind of like go down the right path based on what you've learned from the customer, that is a very valuable skill as well. And how do you develop that? You do it. And it doesn't have to be in the same context or the same domain. You just have to be credible. One thing that for me was valuable when I joined Google, like I didn't write any code at Bump, but I was like an engineer in my last job. So I was like in the code.

• 40:34Speaker 02

  I understood all the engineering. I just didn't write it. And I carried that to Google. And yeah, when an engineer would show me like this thing and it wasn't quite right, I would say, "It can be right. I know it's possible. We just have to do it." And I think that helped push a lot of folks on our team to like build excellent versions of what they were building, as opposed to the version that maybe was like as good as they thought it was possible to build.

• 40:55Harry Stebbings?

  I do want to just touch on product reviews because I think they're quite misunderstood and there's, there's a lot of confusion around them, especially for founders. And so when we think about product reviews for you today, how do you do product reviews? How often do you? Do them, who's invited? Again, think of me as like a early stage Y C company. How would you advise me on how to do them right?

• 41:14Speaker 02

  So first of all, like often people have these standing product reviews, like every two weeks I want to hear what that team's doing. I don't like doing it that way. I think it's personal preference, but I prefer to have it be about specific things or plans or projects that are being done or decisions that need to get made. Where the team has like spent a bunch of time on it, they have an opinion on what they want to do. And they either want like feedback on that plan or they want somebody to make a decision that they don't feel capable of making themselves. And they bring it to a group of people that are the experts on this project, basically the leads of every important part of the project. Design, engineering, product, sales, whatever it is. And you sit in a room and you don't spend all your time like talking about the plan because you probably made a deck or a doc or something about it.

• 41:55Speaker 02

  So everyone should know what the plan is already. In fact, you should know what it is before the meeting because you should be in the details enough to like know what's going on in your company.

• 42:02Harry Stebbings?

  Who created that doc?

• 42:03Speaker 02

  I would say the P M responsible for the thing, if it's a product centric review.

• 42:07Harry Stebbings?

  Okay, and I send it out, I share it three days beforehand, a week beforehand? Do I ask for feedback? Do I ask for commentary?

• 42:13Speaker 02

  I prefer doing it in that form where you send a doc that's very like succinct. And you ask for either general feedback or you ask for directed feedback on a specific set of questions that you want to get people's inputs on. And people can do it all largely asynchronously. And then I do like getting the group together in person to talk about the most important bits. But it should be talking about what hasn't been said yet, bouncing ideas off of each other. As opposed to just rereading the doc or presenting the deck, which I would say 90% of the time, that's what happens. Because humans want to feel validated in their work, they want to feel good, their boss is in the room, yada, yada. That's a big waste of time.

• 42:49Harry Stebbings?

  How do you ensure everyone feels safe to speak? You are, Dave, a product O G. You're very young, Dave, but you know, you've been doing this for a while. You can't just say what you think often. How do you ensure that everyone has equal share of voice and it's a free discussion?

• 43:03Speaker 02

  My approach, to try to just be my authentic self all the time. And then people in the room will realize, even though I look like. Important on paper or whatever. I'm just a regular person. I'm just like you. And I think if leaders who approach leadership that way with like a real authenticity, they're just being their normal self. It's the same person that you saw in that meeting that you would have seen on a Saturday morning at my house. I think that is the best tool that a leader can use to make everyone feel comfortable and able to say what they think. Because again, when have I been most scared in a meeting? It's when I think all the people around me are better and smarter and more important than me. And then I'm like really careful what I say. And that's dangerous for products. You want people to say like all the things that they're feeling. So how do you avoid that?

• 43:45Speaker 02

  You make sure the room doesn't feel like a bunch of important people. It's just normal people. Right? And so I think that's, that's like the tool I use.

• 43:52Harry Stebbings?

  Do you think Zoom helped that? It removed the fear, actually, when you're sitting in a room and you feel that. I think Zoom helps. You're just a square now. I can say what I want. I'm in my home.

• 44:01Speaker 02

  Right. There's a bunch of reasons that virtual makes improvements, right? The, the one you mentioned, which is like, everybody gets their own square. That alone is a big deal. Now everyone literally is on equal pixel footing to everyone else. And some people interact or bring their best selves in different contexts. So having like time to be on mute and like maybe have a doc open and like type your thoughts down and then present, like maybe that works better for some people. I think that's great. But I think there are trade offs. On Zoom, often you just sit there and there's all these squares. Nobody says a word until like the person running the meeting joins and then everyone unmutes. I think you lose a lot of culture building by not having those awkward downtimes. When COVID first hit and we had to like abruptly switch to all remote and everybody was brainstorming, like, how do you keep your team culture? How do you keep people knowing each other, all that?

• 44:46Speaker 02

  The technique that I found most successful, it's the simplest thing I could think of is for every meeting that I was kind of like the top person in, I would just intentionally show up like five to seven minutes late. It creates this awkward silence where everyone's sitting there. And after some number of minutes, somebody unmutes and says like, well, this is awkward. Like, where's Dave? And then they talk to each other and they like say what they were doing, what they're working on, what they did on the weekend. And that alone, I think, is like the best thing that we ever found to drive culture in a remote environment.

• 45:13Harry Stebbings?

  I mean, if you had any Brits on your team, we'd just talk about the weather from the first minute.

• 45:18Speaker 02

  But that's valuable, right? That's really valuable.

• 45:19Harry Stebbings?

  Oh, it totally is. You should hire me. I can chat shit for days. Final one on product reviews. Where do you think product leads most go wrong with product reviews?

• 45:27Speaker 02

  Mostly, it is spending time on things that you could have done outside of the room or aren't actually even relevant at all. It's really cutting to the meat of why are we in this room? And again, it's really hard. Like, you've got some person there presenting, they've spent, obviously, like, so much time getting ready for this big review. It's hard as a leader to say, "Stop talking. I've already read your doc. I don't need to hear this." What I do want to know is what do you think we should do about this question? Talk to me about it. That is a skill that's very hard to master. Again, you're, like, kind of being rude to a person, and that's difficult. But it's the best way to make it an efficient use of time. So I like product reviews where it's really a debate about what we should do. And people bring, like, different perspectives on that debate. And you fight it out. The best product reviews I can remember on Google Photos were ones where I had, like, heated debate.

• 46:10Speaker 02

  And if you talk to some of the folks on the team, like, my boss in the early days, he and I, like, had heated debates about what to do. But we often got to a better answer as a result. If everybody just is the yes man and says, "Yep, we'll do the thing you said we should do", you will miss big, valuable opportunities.

• 46:25Harry Stebbings?

  Final, final one on product reviews. You don't want it just to be like a great discussion, and then what? What's the right post-meeting process to ensure that the discussion items are implemented in some way?

• 46:36Speaker 02

  I think the simple thing is, whatever you decide to do in that room, somebody needs to be the singular owner of each of those things happening. And again, this is probably broader than product reviews. It's more like, how do you run a larger-scale team? And what I have found, again, is you lose a lot of value the minute responsibility gets sharded across multiple people. If there are, like, three people who say they're gonna clean up the floor, who's gonna actually do it? It's less likely that the floor gets clean when there's three people responsible than when there's one person responsible. I always loved operating in this model. You know, Apple calls it the directly responsible individual, which is just a person, and it's not necessarily the boss of all the people, just a person who's designated as, like, your job is to make sure this thing succeeds. If there are any roadblocks, you escalate it to whoever you need to escalate to so they can help fix the problem.

• 47:21Speaker 02

  I think that's the way you should come out of all these reviews. Like, who's responsible for each piece of this? When are you gonna get it done by? And getting them to sign up for that.

• 47:28Harry Stebbings?

  I think that singular accountability is so key. Final one before the quick fire and it's you've invested in some of the most unbelievable companies. Your track on the angel side is astonishing. When you think to the incredible companies you invest in, how has your mindset on product changed through those angel investments and through that portfolio building?

• 47:47Speaker 02

  I guess the biggest learning is companies are very different. I've invested in such a broad scale of companies that like, things that I thought were like, that was the reason like we succeeded on Google Photos. I then look at another company, I'm like, well, they didn't do any of that. And yet their company is worth billions of dollars. Like, there's different ways to solve these problems. That's probably the number one learning is like, there's so many different ways to do this. The things that I've found are common across all the successful companies that I've invested in. Like, that's an interesting question. What is it about these companies? Generally, I would categorize it as there's a person with a chip on their shoulder that wants to prove to the world that they can succeed at something, or prove all the haters in the world wrong. That's one. Number two is that person, usually the same person, has to be like incredibly charismatic because they need to get really smart discerning people to choose to work for them

• 48:32Speaker 02

  when it probably doesn't make any sense for those people to work for them. That's gotta be true. They have to approach the world with this mindset that they will succeed. The best founders I've invested in are people that when I met them, I was like, I don't know anything about your business. I really have no business investing in this company. Like, what am I thinking? But there's something about you that I just think you're gonna win at whatever you do. Best example, my first angel investment ever was Fluxport. I met Ryan Peterson at a wedding. I was friends with the bride. He was friends with the groom. We both showed up. We were like, oh, hey, how's it going? You do something in tech? Like, we talked. And I left that wedding just thinking like, I would not wanna be on the other side of a competition with Ryan. He will eat you alive.

• 49:10Speaker 02

  So when he was raising money, I had said like, well, I don't have any money, but I wanna invest. So I put like the most I could possibly put in because I thought he would win at whatever he did.

• 49:18Harry Stebbings?

  Is Flattestport your best performing investment?

• 49:20Speaker 02

  From a multiple perspective, it will be. Who knows until the cash is in the bank. But I didn't have any money. It's probably my smallest check.

• 49:26Harry Stebbings?

  Did you, did you write the same checks as every single company?

• 49:29Speaker 02

  Well, at the time, I, it was, there was one company I could invest in and I have no money because like we hadn't yet really gotten any liquidity from Pomp. So that was like the only company I could invest in. Later on, yeah, I've generally tried to keep my check size reasonably static because it's very hard to know upfront which companies are going to be successful. And in fact, often your gut will tell you the opposite of what actually will happen. The companies that seem the stupidest or the craziest, and you're just like, I don't know, but I like the founder, I'll invest. Those are the ones that turn out to be big wins. If you modulate your check size based on like probability of success, or like how big the market is or whatever, you'll probably be doing the exact opposite of what you should do.

• 50:06Harry Stebbings?

  That's why the transition from angel to venture is fucking hard because you don't write those checks when it's like, ah, doesn't make sense. But good people, cool. You can't do that. Or you can, you can, and the best do, but it's very difficult to do. I want to move into a quick fire round. So I say a short statement, Dave, and you give me your immediate thoughts. Does that sound okay?

• 50:24Speaker 02

  Okay, well, yeah, let's see.

• 50:25Harry Stebbings?

  Did you really get fired from Google twice?

• 50:28Speaker 02

  This is the first question to the quick fire round. My God, I didn't get fired from Google. I did get asked to leave the team twice. I'll give the shortest possible version of this story as I can. In the early days, right after we got acquired, there was a vigorous internal debate about whether Google should build a private, non-social photo management tool, which is what we got acquired to do, or should we continue on the Google Plus building a social network track? There was vigorous debate. It turns out the person that we reported up through cited on the, yeah, we're doing the social thing, that's what we're doing. I felt so much conviction about Google Photos and that it would be successful, the Google Photos that we ended up ultimately building, that I just decided to not take no for an answer. Like in big companies, there's this phrase disagree and commit when like your bosses tell you to do something you don't want to do.

• 51:12Speaker 02

  If you talk to anybody I've ever worked with, I'm very bad at doing that. It's very hard for me to do something that I don't believe in. And so I just decided, I'm not going to do that. And I basically just told everyone like, no, I'm going to keep building this with these people on the team, so sorry. And I did that because I like had a unique situation. We got acquired, I didn't care about my Google career, I wasn't there to like make L whatever on the job ladder, I just wanted to build Google Photos. So I decided to take a big risk and go for it. And yeah, they told me like, okay, well, then you need to leave, like you're not on the team anymore. And again, I just didn't take no for an answer. I called up a bunch of people that I knew in the valley who had the ear of Larry and other folks on the board. I think was at least part of the reason why ultimately we changed our minds as Google and decided to build Google Photos.

• 51:54Harry Stebbings?

  Do you still have a chip on your shoulder? You said multiple times about it. Do you still today?

• 51:58Speaker 02

  It's a great question. I don't feel it anymore. I don't feel like I need to prove that maybe our startup was worthwhile. Like it was good that people invested millions of dollars in our startup. I don't feel that I need to prove that I could build a product that people love like I've done it. There's probably other domains where I do have a chip on my shoulder, like I'm about to join Y C, right? And try to help very early stage startups, try to pick very early stage startups. I don't feel yet that I have proven that I'm good at that and I want to.

• 52:23Harry Stebbings?

  What are you most nervous about there?

• 52:24Speaker 02

  What am I most nervous about? Well, you like highlight my track record as an angel investor, but the dance is still going. The game is still on. So who knows if I will actually end up being a good angel investor or not. You don't know for decades, right? I think that's probably one of the things I'm most nervous about is Y C is really good at picking the best companies. And I feel a little bit of imposter syndrome going in where it's like, am I actually any good at this? And I want to learn. That'll be fun.

• 52:47Harry Stebbings?

  Which product leader outside of Google Photos do you most admire and why?

• 52:51Speaker 02

  I really like Kevin Wheel. He's at Planet now. He was at Instagram before that and Twitter before that. The reason I like him is I think he's got this authentic feeling, combined with the ability to like really push a team hard and get excellent results.

• 53:04Harry Stebbings?

  I actually have him on the show on Friday, so I'm one of the happy to hear that. What one piece of advice would you give to a product leader starting a new role today?

• 53:10Speaker 02

  Get into the details as much as possible, as quickly as possible. Go to all the people that you now lead that that report to you, really start to understand all the stuff they're working on pretty deeply. That's what I would do.

• 53:22Harry Stebbings?

  What would you most like to change about the world of products?

• 53:24Speaker 02

  I think the product manager role as defined by the world is way too pigeonholed. We should broaden the responsibilities of the P M role. I think they should be much more responsible for design, much more responsible for engineering, for analytics. Like I think we box them into like a very small box and the result is they don't feel this unreasonable ownership over a product. And I think they should.

• 53:48Harry Stebbings?

  Final one, what recent company product strategy other than Google or Google Photos have you been most impressed by?

• 53:54Speaker 02

  The first one that comes to mind is not recent at all, but I'll say it anyway is. The Tesla master plan. I think it was written in like 2006 when Elon just decided to like write down the master plan for how Tesla would be successful. And then he did the master plan part two, I think like 10 years later, there might be a new one coming. I love that he can articulate like the set of things that might become true, that if true, yield like a big change to the world in a positive way. I think that's what every product leader needs to do is articulate if we succeed and some things have to fall in our favor. How can this be so important and so big in the world? Cause that's what gets people excited.

• 54:28Harry Stebbings?

  Dave, I've absolutely loved this. Thank you so much for my prime questions. Thank you so much for letting me harass your team for a week or so. This has been a joy and I so appreciate you joining me.

• 54:37Speaker 02

  My pleasure. Thanks to everyone for listening.

• 54:41Harry Stebbings?

  I so love doing that episode. David is one of the most humble but authentic leaders I've had the chance to have on the show. Such a brilliant product mind and huge thanks to him for giving up the time today. But before we leave you today, we have to talk about the game changing tool that is Miro. Are you and your product team still going from tab to tab, tool to tool, looking for the most accurate information, but losing out on brilliant ideas? Well, you may not just be a PM in that case. I'm a podcast host and I need to constantly be balancing the deliverables from multiple different stakeholders. Whether it's my team locking down interviews, voting on potential topics for future shows or directing feedback from guests. I need to manage a show like a PM manages a product and loss of information causes real inefficiency.

• 55:24Harry Stebbings?

  So I keep track of it all using Miro, the collaborative visual whiteboard that brings your product team's great work together in one place online. Miro acts as this infinite canvas where ideas and projects can be shared across a team and across the tools they use. So how do I use Miro as a podcaster with every episode? Well, with every show that we do, we create a new Miro board. My team takes 10 reference calls before each episode for every guest and they compile all of their call notes on a Miro whiteboard. Then I can jump into it, see all the call notes in one place and then write the schedule for the show with all of them in front of me. Easy to access and at the same time, total game changer. And that's why over a million new users join Miro every month. Get started today with your first three boards absolutely.

• 56:08Harry Stebbings?

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• 56:49Harry Stebbings?

  to get a huge discount off your NordVPN plan plus one additional month for free. It's completely risk free with Nord's 30 day money back guarantee. And last but not least, you have to check out Builder.ai. They make building software so easy that anyone can do it. If you have a vision, you can build it with Builder.ai. And one of my favourite products of theirs is Studio. I always think the number one reason people fail is they do not start. And Studio is the perfect tool for when you need an MVP fast. And when I say fast, you can build simple, beautiful native apps in less than one day. Don't just take my word for it though. Leading brands like Pepsi, BBC, Fujitsu, all love and use the product. Head over to Builder.ai to find out more.

• 57:33Harry Stebbings?

  As always, I so appreciate all your support and I can't wait to bring you an incredible episode this coming Friday with Giulio Vasconcellos, Managing Partner at Atlantico.