David Lieb: How I Founded Google Photos & Bump; Why I Left Google | 20VC #927

1. 0:00 – 2:16

   How did you come to lead Google Photos?

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. 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, you know, Juan to Jamie to James. So, thank you so much for joining me today.

   2. DLDavid Lieb0:18

      You bet. It's my pleasure.

   3. HSHarry Stebbings0:19

      Now, I wanna 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, you know, lead Google Photos for the last seven or eight years?

   4. DLDavid Lieb0:31

      Yeah, I would say it's largely accidental is the- is the true answer. Um, I was an engineer by training in school and I worked as an engineer at Texas Instruments, uh, early in my career. And then, I think like a lot of smart engineers of my era, um, the thing you do next is you leave and you go to business school to learn, quote, "Business," uh, which I did. And, uh, 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, 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 hasn't anybody solved this problem?" Like, this should be a solved problem in the world. Like, maybe I can make a side app that would like make it work. Uh, 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 on the order of tens of thousands of dollars. And, uh, 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." Uh, (laughs) and we said that, you know, for ten 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, uh, which was like this nascent like startup incubator thing. Uh, only we applied to it on a whim and w- 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, uh, and I've been doing that. Um, and then, of course, like we pivoted a few times with Bump and ultimately decided to work on photo sharing and then got acquired by Google and then I was there for nine years. (laughs)

   5. HSHarry Stebbings2:11

      Now, I- I- I wanna... There's bits of your career which I wanna kind of unpack, but I do have to ask, and Juan asked this

2. 2:16 – 3:30

   Lessons from founding Bump

   1. HSHarry Stebbings2:16

      one as well. He said, "What are the one, two biggest lessons for you from your time founding Bump and the transition to Google Photos?"

   2. DLDavid Lieb2:22

      Yeah. I would say for startups, like when you've done a startup, you realize that th- 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, um, requires like you to do basically everything, uh, at least at the very beginning. So, I think the- 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, you know, m- 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. Um, every PR, every press interview, like that was all just us. We had to learn it on- on our own. And I think that's a skill, this like generalist skill, um, that generally people don't have at big companies because they don't need to. Uh, there's- there's experts at big companies that do everything. But, um, uh, 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.

   3. HSHarry Stebbings3:28

      Do you know what I find the hardest thing? Letting go,

3. 3:30 – 4:35

   Advice to founders on letting go

   1. HSHarry Stebbings3:30

      which is like moving from founder-led sales to team-led sales. And I still have this today where I- I might know I can do it better than anyone else. I may be able to do it better than anyone else. I don't mean that arrogantly. But I still shouldn't be doing it.

   2. DLDavid Lieb3:42

      Yeah.

   3. HSHarry Stebbings3:43

      And that...

   4. DLDavid Lieb3:43

      Yeah. I think, if you-

   5. HSHarry Stebbings3:44

      Do you have any advice on that for me?

   6. DLDavid Lieb3:46

      Yeah, you certainly need to make that trade-off at some point, but I think most founders do it too early. They think they, 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." Um, usually that's the wrong answer. Like usually, you are the person who knows the product and the customer the best. Um, and so you should probably be the one doing all of those important jobs for- for longer than you think is reasonable. Like, 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, um, who really knows what they're doing and can shadow you and- and kind of take where- take it from where you are right now and take it further.

   7. HSHarry Stebbings4:31

      You have full license to end this call with this next question,

4. 4:35 – 6:22

   When do you know you have product-market fit?

   1. HSHarry Stebbings4:35

      but you mentioned some notion of product market fit. There's so many different notions and I have so many founders I work with saying like, "I don't fucking know if I've got it or not."

   2. DLDavid Lieb4:44

      (laughs)

   3. HSHarry Stebbings4:44

      Some people are somewhat disappointed, some are not disappoint... 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?

   4. DLDavid Lieb4:55

      Yeah. Uh, if you don't know if you've got it or not, you don't, um, is the simplest answer, right? Uh, it- it is a thing where something clicks and people just use your product or demand your product so much more than you could have ever fathomed. Uh, that is generally when you've got some initial glimmers of product market fit. Y- 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. Um, 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." 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.

   5. HSHarry Stebbings5:47

      Can product market fit die?

   6. DLDavid Lieb5:51

      Like, can you lose it?

   7. HSHarry Stebbings5:52

      Yeah.

   8. DLDavid Lieb5:52

      You- you've once had it and then it goes... For sure.

   9. HSHarry Stebbings5:54

      Yeah.

   10. DLDavid Lieb5:54

       The world changes, right? Um, look at any successful product 20 years ago. Most of them are dead, right? (laughs) Like, what are the ones that are still really around? Google, um, Microsoft Word. What else? Uh, Windows.

   11. HSHarry Stebbings6:08

       ... Amazon?

   12. DLDavid Lieb6:08

       Mo- Yeah, Amazon barely, right? Uh, but I would say a lot of the things that we used regularly, you know, a generation ago, they're gone, because there's- the world changed and there's better solutions to those problems.

   13. HSHarry Stebbings6:19

       I love the way I have these articulate schedules and then I just

5. 6:22 – 8:11

   Why did you sell Bump?

   1. HSHarry Stebbings6:22

      get too interested. Why did you sell Bump? It was a great product. I remember it back in the day. It was great. Why did you sell?

   2. DLDavid Lieb6:28

      Well, the simple answer is we, uh, need- we were gonna need to raise some more money and we weren't sure that that was the right idea, uh, for ourselves or for the team or for investors. Um, so usually when you sell a company, it's 'cause you- you either really can and want to, or you need to. For us, we kind of needed to. Um, I think the bigger answer is we had stumbled upon an insight that I think a lot of people in the world hadn't yet had, which is with these mobile phones that now everyone has, um, we are soon going to be inundated with this repository of photos and videos that we really care about, but we have no idea what to do with. Where will they live? How will we keep them? How do you keep them organized? Like, what in the world? Um, and I think we found that insight before most people in the world because we were kind of living at the cutting edge of mobile phones. We were taking a lot of photos ourselves to test how Bump would work. Um, and I remember, like, back in the day, y- you're probably too young for this, but, um, back in the olden days, you would take photos on your iPhone and they were just on your iPhone and they filled up your s- your disc on your iPhone, and there was no solution. So you had to, like, plug your iPhone into your computer and then go into the file explorer and drag the photos off of your phone into some folder on your computer. Then you had to figure out, like, "Well, where should I put them on my computer? Should I back them up online? Like, what should I do?" It was a real schlep, um, and most people in the world didn't do any of that. And so I think we just realized, like, "Oh, in five years everyone in the world is going to have this problem that we are currently having today, uh, and we have some ideas for how you would solve that." A- and that's kind of, like, how we, I think, had that insight.

   3. HSHarry Stebbings7:57

      Dave, you are a charmer. I'm not quite that young.

   4. DLDavid Lieb7:59

      (laughs)

   5. HSHarry Stebbings7:59

      I do remember those days (laughs) . Um, I- I do want to ask, you know, when you- you mentioned obviously the insight there with the Google Photos and kind of the explosion of data and photos that one would have on- on a phone. You know, a- again, Juan, cracking

6. 8:11 – 10:40

   What made Google Photos a success?

   1. HSHarry Stebbings8:11

      questions from Juan. He said, "What were the top one or two decisions when on- in hindsight that you think made Google Photos the success that it was or is?"

   2. DLDavid Lieb8:21

      I would say the- probably the number one, the meta- the meta decision that we made early on, um, was around what our mission would be. Um, and I think this is a thing that often gets overlooked or not enough time is spent on- on bigger- in bigger companies. Uh, it's probably more critical at small companies that you figure this out. But, uh, we decided that we would have a very clear mission, which was to be the home of the world's memories, right? 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, right? And we said internally at Google, like, "We're not gonna build a social tool. This isn't a social network. Like, that's not what we're doing. Uh, we're not gonna build some crazy, like, photo editing product." Like, it's not about being, quote, "creative with your photos." It's about storing your life's memories. And 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. Um, one is it really helped us select who should be on the team and who shouldn't be on the team. Um, there were a bunch of people that were on the existing... uh, we- we kind of spun the team out of the Google+ team, 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. I think it was great for them and great for us. Um, 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 10 years of your life, like, solving this problem in the world, you shouldn't come work on this team." Uh, and I think that really set us up for success, and- and to this day, like, everybody on the team knows that mission by heart.

   3. HSHarry Stebbings9:54

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

   4. DLDavid Lieb10:05

      I think at best they have something written down. I really doubt they think about it on a daily basis and- 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." Uh, and we just decided we would, like, really focus on that, a- and I think it was, you know, it's the right thing to do.

   5. HSHarry Stebbings10:24

      I- I totally agree with you in terms of doing the right thing, and I like in terms of self-selecting talent. Wh- when I spoke to so many of your team, what really shone through was just what a incredibly kind of loyal and- and really bought in Googler y- y- you are. And I think the thing that kind of shocked me,

7. 10:40 – 13:15

   Why did you decide to leave Google?

   1. HSHarry Stebbings10:40

      and we chatted about it a little bit before the show, is why did you decide to leave Google most recently, and- and what was behind that thinking?

   2. DLDavid Lieb10:47

      Yeah. Um, well, so I- I had been at Google nine years. I left last week. Um, and I would say the trigger for me finally... S- so the reason I stayed, first, the reason I stayed for nine years, right, um, is I just really wanted Google Photos to exist. Um, it was a thing, it was an insight that we had at our startup that, like, there was this big problem, and we thought we had an idea for how it would work to solve it. Um, and I just really wanted it to work. You know, I would say, like, uh, maybe this is a slight digression, but I had a- a chip on my shoulder. Uh, we had, like, worked on our startup for five years. It was like this, in many ways, like, a very big success. We had 150 million users. We were number one or two on the App Store in almost every country. Um, and yet, like, we didn't figure out a way to have it be a sustainable business, um, and so we decided to ultimately sell it. Um, but, like, I didn't want those five years to kind of be all for naught. For everybody on our team, everybody who contributed to the success of Bump, I wanted something, like, long to come from it. And so I just had this chip on my shoulder that, like, I needed this next thing to be successful. Um, and so I stayed for a long time to make sure that would be the case. Last year, I, um, was diagnosed with surprise leukemia, uh, and so I was out for a year doing chemo and- and fighting that, uh, and so the team, like all of the folks who reported up to me, like, on a random Thursday, they just had nobody anymore. They had to r- you know, step up and do it all themselves. And for an entire year, they did it, and they did it great. Um, and so (laughs) when I came back, it was kind of like, "Oh.... a-a-and it works, like it's okay without me, um, I ... And it, 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, a near-death experience. The-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. Um, and when I got through that, through that, like, quite difficult year, um, I just decided, like, "Wow, life is indeed short." Like, you hear this from everyone, like everyone tells you, "Life is short. Do, do what you care about." Um, but I've, like, actually felt it now, um, and I decided, like, I should do what I really love doing. And for me, I love startups. I love, um, helping founders, I love ... I loved being a founder when I was one, and I just wanted to do that, kind of, with all of my time. So I decided to, to leave and, and join YC.

   3. HSHarry Stebbings12:56

      And, I mean, what an exciting time to have with YC and, um ... And thank you also for sharing that. I, I hope that wasn't too personal, but, um, totally love hearing that, and exciting, as I said, on YC. I, I suppose y- you ment- 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.

8. 13:15 – 17:05

   Is product more art than science?

   1. HSHarry Stebbings13:15

      And I thought that was a good entry point, because there's often this tension between art and science in product. So as a starting point, is product more art than science? How do you answer that one? (laughs)

   2. DLDavid Lieb13:25

      Hm, what a question. M- my opinion is, uh, for ... Uh, the, the meta-answer is it really depends, but my, my opinion is it's more art than science, um, and so let me explain maybe why I believe that. Um, if you look at, like, truly great products, pick any product that you use that you're like, "That product is just really well done," um, generally there are a very small set of people behind that product that really love it, that obsess over every single thing about it, um ... 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. Um, and how do they make it great? Why is it so great? It's because they love it. They love that product, they love the customer, um, 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. Um, I think 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. Um, and you can't do that with science. Like, you can't just do experiments and see, "Oh, experiment arm 1A was the best-performing one. Like, let's go with that." Uh, you have to understand the customer and really feel what they feel, and I think that is much more art than science.

   3. HSHarry Stebbings14:37

      Can I ask, when 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-

   4. DLDavid Lieb14:51

      Mm-hmm.

   5. HSHarry Stebbings14:51

      ... we can make analytical decisions with a lot less, uh, irrational gut-

   6. DLDavid Lieb14:56

      Sure.

   7. HSHarry Stebbings14:56

      ... because we are not feeling the pain.

   8. DLDavid Lieb14:58

      Sure. I mean, I, I, I agree with both of those statements. Like, I think if you're being very analytical, um, you will avoid large mistakes, uh, because your, 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, um, unexpected wins, right? So, if you think of maybe in, in like a scientific way, uh, using science kind of 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, uh, because you would never try it. And that's why I think doing it more of an art is, 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. Uh, 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. Um, and so that's why I think going with your gut and understanding the customer personally, um, 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, um, that's the way you find these big upside outcomes.

   9. HSHarry Stebbings16:01

      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 risk-

   10. DLDavid Lieb16:13

       Yeah. You know, um, I, I think s- m- repeat founders often, they, they know more about how the game works and so they, um, I think they alter their behavior to some extent. It ... Both for the good but also for the bad. They, they don't let themselves run crazy on some wild idea that everyone around them thinks is stupid. Uh, they generally feel some peer pressure to not do that. Whereas very young founders, like naïve founders to some extent, uh, they will go off on crazy pursuits, uh, 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." Um, and then they build something that people really love. Um, and so I think, you know, to some extent as, 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, and understanding that customer

9. 17:05 – 18:40

   Can you trust your gut?

   1. DLDavid Lieb17:05

      very deeply.

   2. HSHarry Stebbings17:06

      Can I ask, uh, Jamie Aspinwall on your team said, "When gut instinct is the primary tool, Dave is the master." He wins. (laughs)

   3. DLDavid Lieb17:14

      (laughs)

   4. HSHarry Stebbings17:14

      Um, (laughs) brilliant. Uh, I hope I have team members that say the same about me. Um, but, uh, 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?

   5. DLDavid Lieb17:28

      Yeah. Um, so people often refer to, like, using your gut or trusting your gut, um, and I think often they say it in kind of, like, a, a derogatory way or, like, "Oh, your gut is just, like, uh, this thing on a whim that you should be careful about." Um, I have a different view. I think your gut is the world's most sophisticated machine learning model ever created. Um, it is, like, the best supercomputer we've got, um, 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, um...... there, the people who wrote the code, you know. 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. Um, what an amazing thing. And I think we don't, we, we discount it. Um, but instead, we should leverage it. My God. So y- what, what I try to do is put as many inputs into this machine learning model that you can. Learn as much as you can about your customer, try as many experiments as possible, and put it all into your brain, and then see what your gut says you should do next.

   6. HSHarry Stebbings18:28

      Okay.

   7. DLDavid Lieb18:28

      Um, and I think that is actually, like, a quite, um, quite analytical way to approach the world.

   8. HSHarry Stebbings18:33

      Okay.

   9. DLDavid Lieb18:33

      You're just using a tool that people aren't used to using. (laughs)

   10. HSHarry Stebbings18:35

       I'm s- I love that as a statement, as a sophisticated machine learning model. But it, it kind of

10. 18:40 – 20:50

    How Google Photos instilled trust

    1. HSHarry Stebbings18:40

       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-

    2. DLDavid Lieb18:55

       Mm-hmm. Mm-hmm.

    3. HSHarry Stebbings18:55

       ... but also ensuring quality and perfection?

    4. DLDavid Lieb18:59

       Yeah. I think it really depends on your context. Um, so like, in the context of Google Photos, we were at Google, we were planning to launch this new product, Google Photos. Um, we kinda knew that, like, the world would hear about it. Um, we, we would get some trial users on day one, right?

    5. HSHarry Stebbings19:14

       Uh-huh.

    6. DLDavid Lieb19:14

       Um, so we decided, in that context, um, "We better make that product pretty great for those people because otherwise, they're gonna try it and they're gonna be disappointed." Um, and I think 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, uh, "We better make that feel like a trustworthy thing, and it better be great to use." So in that context, we decided, um, "The bar's gotta be reasonably high, at least for the core parts of the product that, that convey that trust to people." So, like, as an example, the, the main grid of Google Photos, like, you're scrolling your photos and it has all the squares with all your photos, uh, we very early on, this maybe is an answer to your previous question, uh, decided that thing 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 on the screen if you want to see it. Um, 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. Uh, but I think that was the right trade-off for that context. Now, switching gears to, like, the beginning of Bump, let's say. There's another thing that I worked on. Um, the first version of Bump, I look at it and I'm, like, very embarrassed by it. It was, it was horrible. It was terribly designed. Like, who designed it? Like, somebody who's never done a design before? Yes, (laughs) me. Right? (laughs) Um, a- and I think e- you just gotta understand your context and what risks you're willing to take. Um, for most startups, the answer is, you should probably ship something and learn something from someone, um, and then you can make it better. If you're a big company, you might need to make something, like, quite good before

11. 20:50 – 23:35

    How to listen to customer feedback

    1. DLDavid Lieb20:50

       you want to launch it.

    2. HSHarry Stebbings20:51

       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.

    3. DLDavid Lieb21:01

       Mm-hmm.

    4. HSHarry Stebbings21:01

       How do you think about the feedback to ingest and act on versus the feedback to always listen to, but not necessarily act on?

    5. DLDavid Lieb21:10

       Yeah. Um, I think there's two bits in there. Um, o- one bit is who are you talking to and are they representative of your desired user base in the future? Um, it's really great if the answer is you are representative of your desired user base. So I would say in the case of Google Photos, like, that was pretty much true. And I would say it still is largely true today. Like, me personally, I think I'm, like, quite close to the center of the distribution in terms of, like, what type of people wanna do what with their photos. Um, the second bit, though, is, like, what are they saying to you and what are you taking away from it? Um, I think too often, a- and this is, like, something people talk about all the time, so it's not new. But 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. Um, 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 s- 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 this? Or maybe this thing, like, doesn't matter to them and they haven't, like, put in any effort to understand it. Like, maybe I'm just not solving a big enough problem for them. Um, s- so you have to un- understand the why behind what they're saying, not what they're saying.

    6. HSHarry Stebbings22:27

       How do you get to that layer deeper? Like, how... I, I find customer discovery one of the hardest things.

    7. DLDavid Lieb22:32

       Yeah.

    8. HSHarry Stebbings22:32

       Often, people ask leading questions. What's the right way to get the truth from that process?

    9. DLDavid Lieb22:36

       Um, it is some form of repeatedly asking why. Like, "Why do you care about that? W- in what context do you, do you do this? When was the last time that you had this problem? Like, what did you do w- without our product, uh, when you had this problem?" Uh, these are the types of questions that give you the context to really understand what's going on for that person. Um, because g- I think another thing that we forget about when we're, you know, 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 gonna 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. A- 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.

    10. HSHarry Stebbings23:27

        Can I ask, when does one rely on that gut intuition, more human incentive, versus let's look at the numbers,

12. 23:35 – 24:45

    Data vs feedback

    1. HSHarry Stebbings23:35

       let's look at the data, and let's go to the cohorts? 'Cause there-

    2. DLDavid Lieb23:37

       Yeah.

    3. HSHarry Stebbings23:37

       ... I'm sure there's a time for both. When is the time for data?

    4. DLDavid Lieb23:40

       A- absolutely. Data is a fantastic tool. Um, it tells you a lot of information all at once that can be very useful directionally about where to go. Um, I dislike most aggregated statistics. Like, you know, "Yesterday, we had this many users upload a photo," or, "There were this many comments on this post yesterday." Um, because they can be very misleading about what's actually happening for individual users. So I much prefer looking at data around individual users in an, in a, um-... large scale way. So like, let me explain what I'm talking about. Uh, 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 does your cohort retention curve look like? If 100 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, once the other folks who've decided it's not for you have left, um, because that tells you about individual users, right? Um, the other tool that I really like, um, and there's a variety of-

    5. HSHarry Stebbings24:44

       Can I just, can I just dive in

13. 24:45 – 26:48

    Cohort retention curve

    1. HSHarry Stebbings24:45

       there?

    2. DLDavid Lieb24:45

       Yeah.

    3. HSHarry Stebbings24:45

       Sorry, I'm, I'm too interested by you on that point.

    4. DLDavid Lieb24:47

       Yeah.

    5. HSHarry Stebbings24:47

       When you said about that cohort retention graph, when 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."

    6. DLDavid Lieb25:00

       Mm-hmm.

    7. HSHarry Stebbings25:00

       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, you can kind of alter the data to fit the way you want it to be.

    8. DLDavid Lieb25:16

       Yeah, right. Well, yeah. I, I certainly see people do this, where they say, you know, "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. Um, inevitably, you're going to have some folks in your funnel that should not be your customer, right? You think they shouldn't be their- 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. Um, 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? Um, 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, um, they use it more as the product gets better or more people in the world use it or whatever network effect might, might exist happens.

    9. HSHarry Stebbings26:07

       Can I ask, what do you think are the biggest mistakes that founders make when they construct and then examine their cohorts and retentions?

    10. DLDavid Lieb26:14

        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. Now, do I blame them? No, because I did exactly the same thing when I was a founder. Uh, we were raising money for Bump. Uh, 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 had no idea what they were talking about." Like, I should- I should know these things. Um, but yeah. So I get it. Like, it's not a normal thing. It's not a thing you do in life

14. 26:48 – 34:05

    What are good retention numbers?

    1. DLDavid Lieb26:48

       ex- except for this. (laughs)

    2. HSHarry Stebbings26:49

       So for, for me, I, I always look at 30 day. I find, like, anything below 30 day actually not indicative of, like, true habit forming behavior. And it is very different depending on product, I completely understand and know.

    3. DLDavid Lieb27:01

       Mm-hmm.

    4. HSHarry Stebbings27:01

       Um, but say for a product like, uh, Google Photos or for BeReal, which I'm an investor 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.

    5. DLDavid Lieb27:24

       Mm-hmm.

    6. HSHarry Stebbings27:24

       What is good?

    7. DLDavid Lieb27:25

       Yeah. Um, for a product like Google Photos, let's say, that's the one I can speak to because I, I really understand it, um, I think a good user of Google Photos is using it almost every day.

    8. HSHarry Stebbings27:36

       Right.

    9. DLDavid Lieb27:36

       Right? Like, there's m- most days of the week, you should be doing something with your photo library, whether it's looking at your photos, sharing a photo to your partner, um, you know, deleting a bad photo that you took. A- and so we would look at, um, cohort retention with either a daily or a weekly time period. Like, 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. Um, I think that is the best way to see, like, what's actually going on. What you, what you normally find, however, is people want to show charts that look good. So they show, like, number of users in the last 30 days. Like, "This is our, our, our MAU, monthly active users." It makes you feel great, but, like, did those users really love your product, um, 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.

    10. HSHarry Stebbings28:25

        W- what-

    11. DLDavid Lieb28:25

        This is a fun anecdote from Bump. In, in, in the Bump, um, kind of heyday, we had 150 million installs on, on phones when the market for phones was only like, I don't know, maybe a billion phones in the world or probably less than that, probably hundreds of- high hundreds of millions. So we were on like 20% of all phones in the world. We were a big blue icon on the home screen. And what we found in our data, um, and here's an example of like looking at data to understand something, 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. Huh." And we would then- we then looked at our data and we were like, "That's what it is." It's people, you know, you have a one in 100 chance of accidentally tapping the wrong icon. Multiply that by 150 million users, like, you're gonna get some users doing that. So you got to 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 20% of the time, it was accident. They didn't mean to use it. (laughs)

    12. HSHarry Stebbings29:36

        What is good retention numbers? Is it 30%? I remember Jeremy Liu told me, I think it was 36% Snap pad on 30 day retention. Um, what is good?

    13. DLDavid Lieb29:46

        It really depends on your product and your user acquisition channel. Um, you know, all that matters to me is that your graph gets flat. It can get flat at 5% of your initial cohort of users, so long as that 5% is flat and consistent and valuable. Like, so, so I think- I, I don't have the actual data, but I remember at one point seeing a curve of Airbnb's, um, I think either 30 or maybe 90 day period cohort retention. And it- it's pretty steep and it gets pretty, pretty low, but it's flat.... and each time they use it, Airbnb makes a hundred dollars, right? So that's totally great. It's a $100 billion company. Uh, so, 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?

    14. HSHarry Stebbings30:34

        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? The- they have the wrong, kind of, they have, um... What would you call it? Um, like, attraction metrics, like, you know, MAEs, which maybe-

    15. DLDavid Lieb30:45

        Right, things that make you feel good, but actually-

    16. HSHarry Stebbings30:47

        Yeah, everything else.

    17. DLDavid Lieb30:48

        Yeah.

    18. HSHarry Stebbings30:48

        If I'm a YC company and I'm coming to you-

    19. DLDavid Lieb30:50

        Yeah.

    20. HSHarry Stebbings30:50

        ... is there anything else you'd say?

    21. DLDavid Lieb30:52

        Um, 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, um, but it doesn't tell you why. It just tells you what is true, right? Um, 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. Uh, 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. Um, it might inform areas of exploration or, like, "Why is it that we have one-second sessions on Bump? M- maybe we should go figure that out." Um, but it should not tell you what to do. Um, instead, you should go talk to users and hear... Like, ask them, "Hey, have you ever opened Bump for like a second and not used it?" And they may tell you, like, "Oh, yeah, sometimes I accidentally open it. Whoops, sorry." And then, ah-ha, you've, like, learned something real in the world, as opposed to the effect of something real in the world.

    22. HSHarry Stebbings31:51

        Can I ask, when you, uh... When you're a startup, often, um, 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 'cause they've been with these incumbents too long.

    23. DLDavid Lieb32:07

        Mm-hmm.

    24. HSHarry Stebbings32:07

        If you're advising, again, me as a YC 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-

    25. DLDavid Lieb32:18

        I think you should be, I think you should be careful, um, for sure. The- there's a set of people at all these big companies that I think are really great. Uh, I've tried to hire them all. Um, a- and they, they get it and they really want to do all the things needed to be successful. Um, but there's another set of people at those companies that are there for different reasons. They're there, um, for their career. They're there because they want a good paycheck. Um, they're there for the status that these companies bring. And they've never had to solve these problems themselves. This is a, a, 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. Um, you have a legal issue in Estonia? Like, great, we'll go bring in the Estonian lawyer and he'll, like, tell you what, what's going on there. Um, and that's good because you get an expert on every single thing. The problem is none of those experts is responsible for the holistic success of your product. And, um, without that, who really feels ownership to make your thing great? Um, is it the, like, you know, product lead? Is it the design lead? Is it the engineering lead? Is it the marketing lead? Um, w- who really feels like their personal credibility is on the line to make this product successful? And I think that is a, a common failure mode for large companies, is you lose that at some scale and at some size. And, um, it scares me, it worries me for a lot of these big companies.

    26. HSHarry Stebbings33:42

        Well, what did you do to retain it? Why did it work for you?

    27. DLDavid Lieb33:46

        Uh, I guess because I was so used to doing that from the startup where, like, you don't have an Estonian expert lawyer. Like, you have to just, at best, like, call in your, you know, external law firm and see what they tell you, and then you have to make the call. Um, you just get used to doing it yourself, and I think that's a skill set that's very valuable at big companies.

    28. HSHarry Stebbings34:04

        Can I-

    29. DLDavid Lieb34:04

        It's this,

15. 34:05 – 36:35

    How do you create a culture of product obsession?

    1. DLDavid Lieb34:05

       like, holistic ownership feeling.

    2. HSHarry Stebbings34:06

       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, at lunch apparently-

    3. DLDavid Lieb34:14

       (laughs)

    4. HSHarry Stebbings34:14

       ... you were, like, moaning about a feature that you still hate.

    5. DLDavid Lieb34:17

       (laughs)

    6. HSHarry Stebbings34:17

       I heard this. I did my research.

    7. DLDavid Lieb34:20

       Mm-hmm, mm-hmm, mm-hmm, mm-hmm. (laughs)

    8. HSHarry Stebbings34:20

       Um, and my question to you is-

    9. DLDavid Lieb34:22

       (laughs)

    10. HSHarry Stebbings34:22

        ... how do you create a culture of product obsession and granularity within your team?

    11. DLDavid Lieb34:29

        Um, I think you just have to show it yourself. It has to be authentic. Like, you have to personally, um, be obsessed with the success of your product, be obsessed with the product experience, be obsessed with the customer. Um, and then people will see you that it's true. And what's great, and hard, is that it's really hard to fake real obsession, right? Obsession e- is a form of love, um, and love is a very hard thing to fake. Uh, it's... I would argue, like, it's probably the hardest thing to fake in the world. And so you can't just act the part. You can't just pretend to be obsessed about a thing that you're not actually obsessed about. Um, so step one, it's very simple, work on something that you're obsessed with, um, 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, 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, um, slo-mo camera, like, on my other phone. I'd record the grid scrolling, and then I'd play it back in slo-mo for these people, and I'd be like, "Did you see that little glitch there?" And, um, by me just doing that, A, uh, uh, the people who didn't like that maybe decided to leave the team. (laughs)

    12. HSHarry Stebbings35:50

        (laughs)

    13. DLDavid Lieb35:50

        Uh, and B, and B, um, 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, I'm not sure we're ready to ship this 'cause I'm not s- I don't think it's quite good enough yet," um, it makes that okay. It makes them see, like, "Oh, if the, 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." Um, and it just... It, 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, uh, to everyone. And that's where magic happens, I think.

    14. HSHarry Stebbings36:27

        I think fundamentally, you have to have people also with a mindset and willing to adopt it if they don't have it. And I think getting the right product

16. 36:35 – 39:15

    How do you hire your product team?

    1. HSHarry Stebbings36:35

       team together is probably one of the most crucial things you can do.

    2. DLDavid Lieb36:38

       Mm-hmm.

    3. HSHarry Stebbings36:38

       I'm an early stage founder, again, NYC, so seed to series A, okay? Um, you are my mentor. Um, I've never hired a product team before. Um, I'm obviously a charming British sales guy. Um, how do you structure your hiring process for a product team? What is the process?

    4. DLDavid Lieb36:55

       Yeah. Um, well if you're early stage, um, your product team maybe is one person, right? (laughs) Maybe you're hiring one PM. Uh, this is another meta mistake, is people think, like, "Oh, I, 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 cohorts, uh, cohort members doing. Um, that's probably the wrong thing to do unless you really have product-market fit already. Um, but let's assume you, you do. Things are on fire, like, "Oh my God, we've got to build all these things." Like, great news. Um, I would say at the early stage, the number one thing I would filter for initially for product people... And, 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. Um, you... I would say the number one thing you're looking for is ambition. Um, people who really want to be part of this thing and want to have it succeed. Um, and that is very different than what you might hire for in many other areas, uh, or other stages of a company. Um, but ambition at the early stage, you can take, like, a reasonably smart person who has the right ambition, um, and they can do incredible things for you, um, if you give them the right environment.

    5. HSHarry Stebbings38:09

       They have, th- 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.

    6. DLDavid Lieb38:16

       Yeah.

    7. HSHarry Stebbings38:16

       What's the process for assessing if they're good at product?

    8. DLDavid Lieb38:21

       Um, 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. Like, "Hey, what are your favorite products? Like, why are they your favorite products?" See if they've ever gotten to the point of, um, 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? Um, these are th- like, things that are very squishy. It's very hard to, like... How d- how would you, like, write a multiple choice test that would test that? It's very difficult. Um, 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. Um, and the why is what matters. And, uh, like, the skill of asking why and learning why, or figuring out why, I would say that is, like, the number one skill for building early stage companies, is- 'cause 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

17. 39:15 – 46:43

    When do you bring in a CPO?

    1. DLDavid Lieb39:15

       working?"

    2. HSHarry Stebbings39:16

       Uh, can I ask you, when do you think about bringing in CPOs? If we're a scaling company-

    3. DLDavid Lieb39:20

       Hmm.

    4. HSHarry Stebbings39:20

       ... I, I often see the transition required. When would you advise founders on, "Now you need a CPO/head of product-"

    5. DLDavid Lieb39:26

       Yeah.

    6. HSHarry Stebbings39:26

       "... not just jack of all trades"?

    7. DLDavid Lieb39:28

       Right. Now, we're talking, like, much later stage. Um-

    8. HSHarry Stebbings39:30

       Yeah.

    9. DLDavid Lieb39:30

       ... again, most people do this probably too early. (laughs) So that's, like, the common theme here. Um, so I, I made this mistake myself, um, at Bump. You know, we got to, like, maybe it was 30 employees, and we were s- like, all of our, all of our vanity metric graphs were, like, going way up. We were feeling really good. Um, and I thought, "Oh, like, our company is gonna need to, like, figure out our business model eventually. Uh, we're gonna need to keep scaling and hiring. I'm gonna have to do more fundraising. I better, like, hire a, a product lead to take over from me, and I'll go focus on those other things." And I did. We found a really great person. H- he was awesome. He joined the team, um, and then we realized, or I realized, like, "Oh, actually, uh, 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 to do it, and we can't figure out anybody else in the world who will, like, pay us for access to those users in some way. So really, we don't have product-market fit. Whoops." Um, and I realized, like, "So 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." Um, and 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 f- found at some point that, like, "I, I need to be doing that, because, like, it's my responsibility for this company to be successful. Uh, I better be working on this." And now, all of a sudden, we have two people who want to be, you know, top person on product. Uh, and so he and I, like, both looked at it and we were like, "Yeah, this w- whoops. D- Dave made a mistake. Uh, I was wrong about when to hire this thing." Um, and we parted ways, and that was the right call for the company, a- and for him, uh, to be honest, uh, at the time.

    10. HSHarry Stebbings41:11

        Uh, so you said that-

    11. DLDavid Lieb41:11

        He's now a YC founder. (laughs)

    12. HSHarry Stebbings41:13

        (laughs) You, you said there about, kind of the mistake. Uh, a- 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.

    13. DLDavid Lieb41:24

        Hmm.

    14. HSHarry Stebbings41:24

        And they bring someone in, but they still kind of want to own it, and they don't really-

    15. DLDavid Lieb41:27

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

    16. HSHarry Stebbings41:31

        Do you see that often?

    17. DLDavid Lieb41:33

        Oh, for sure. Yes. Um, I think the other piece of it is generally people want to hire people like them, right? Like, the folks you talked to on my team are folks that I would say are, like, similar to me in many dimensions. Um, that, uh, 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 want to hire someone exactly like you with the same set of skills, uh, because you're just gonna butt heads all the time. Um, so as an example, on Google Photos, um, when we grew enough to where, like, I needed to hire someone to run the product team, like, to be the product lead, and I was owning other things too, um, I very explicitly wanted someone who had a complementary set of skills. What are the things that 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, you know, plug a big gap in our team. Um, I think that's, like, the way you should do these things, unless you're planning to leave, in which case, like, you need to hire someone who's, you know, has the skillsets to be the, the singular lead.

    18. HSHarry Stebbings42:35

        Uh, I had Shreyas Doshi on the show as well, and he categorized three different product leaders. He said there's craftsmen and -women, there's, uh, visionaries-

    19. DLDavid Lieb42:43

        Okay.

    20. HSHarry Stebbings42:43

        ... and there's op- operators.

    21. DLDavid Lieb42:45

        Yeah.

    22. HSHarry Stebbings42:45

        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-

    23. DLDavid Lieb42:53

        Yeah. (laughs)

    24. HSHarry Stebbings42:53

        ... who come in and put a lot of process in place-

    25. DLDavid Lieb42:56

        Yeah.

    26. HSHarry Stebbings42:56

        ... and actually do very little. Um, and they like talking to other CPOs and they like talking to the board and feeling important.

    27. DLDavid Lieb43:03

        Sure.

    28. HSHarry Stebbings43:03

        Do you agree with that? And how do you prevent getting that operator which actually just brings process and delays?

    29. DLDavid Lieb43:10

        Right. Right. Yeah, 100% agree. I would say, like, the number one failure mode when people hire product leaders is they over-index on either, like, um, previous scale, like, how many ... h- how big of a team have you previously managed? Or, um, tenure, like, how long have you been doing this? What experience do you have? H- do you have experience in our domain? Um, it turns out that if you're the median PM in the world, if you're, like, middle of the stack, not- not good, not bad, you're just median, um, if you stay in the game long enough, you will be that person. Like, by definition almost. Right? If you last long enough, um, you will eventually lead a team of 25 PMs. Uh, but you're not actually good (laughs) necessarily. You're median. Um, and it's very dangerous to hire those people because, um, you know, you've heard the 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. And once you hire that B player to be your lead, like, bye-bye. Your team is gone. Like, your- the best people on your team are not gonna wanna work with that person. Uh, so, how do you avoid it? I think you gotta retain this ability to be either a craftsman or a visionary. Hopefully both. Uh, because those are the people that people wanna follow. They wanna listen to what they're saying. They wanna work with that person. They wanna work with the people who wanna work with that person. Um, I think it's incredibly valuable. And yet, founders think, um, "You know, I better hire this- this experienced person who knows how to do this." But turns out, they don't actually know how to do it, um, no more than you do.

    30. HSHarry Stebbings44:41

        Is there- is there- is there ever a time for an operator when you are a Smartsheet or an Anaplan or a name your kind of quite non-creative SaaS enterprise product respectfully.
18. 46:43 – 49:44

    Difference between good and great PMs

    1. DLDavid Lieb46:43

       or for, like, a chip on your shoulder. These people wanna prove that they can do this, that they can be successful, that they can win. Um, and those people tend to work harder. They tend to, like, w- understand the customer more. They go the extra mile. And these are the things that separate you, you know, from s- success from losing. Right?

    2. HSHarry Stebbings47:00

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

    3. DLDavid Lieb47:05

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

    4. HSHarry Stebbings47:38

       I've grown- I've grown very used to it as a VC, so. (laughs)

    5. DLDavid Lieb47:40

       That is how ... (laughs) Um, that is how you learn the- what's happening in the real world is you have to put yourself out there and say, "Hey guys," like, "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." Um, and that's a tough feeling. It's a feeling of rejection. That's very difficult for people. Uh, but you have to be okay with that. And so I think, again, that's why folks who come from non-traditional backgrounds, um, they've probably had that happen to them quite a bit in their- in their lives. Right? Whether they went to some, like, no name school and all their peers now at Google, like, went to Harvard or Stanford or whatever. Um, they've felt that before and they are okay with it and they're willing to, like, plow through it. Uh, so I think that's a very important skill set. The second piece is knowing enough about how to build product, the engineering involved, the design involved, like, all the pieces that r- are required to build a great product. Um, knowing enough about that to be the- the kind of ringleader or the champion to take the insight from the customer and actually build something that will solve that customer's problems. Um, so like as an example in Google Photos, you...You have to, n- understand enough about h- 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." Um, understanding that and, 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, like, be credible. So I think one thing that, for me, was valuable when I joined Google, like I didn't write any code at Bump, uh, but I was, like, an engineer in my last job. So I was, like, in the code. I understood all the engineering. I just didn't write it. Um, and I carried that to, 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, be, w- to 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.

    6. HSHarry Stebbings49:43

       Can I

19. 49:44 – 52:18

    Product reviews

    1. HSHarry Stebbings49:44

       ask, you mentioned customer insight there. I, I do wanna just touch on product reviews 'cause I think they're quite misunderstood and there's, there's a lot of confusion around them, especially for founders. Um, 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 YC company. How would you advise me on how to do them right?

    2. DLDavid Lieb50:06

       Yeah. Again, if you're an early stage YC company, like, you probably don't have enough people in your company to even invite to a, a product review. It's probably just a, you know, turn your head to the person next to you and, like, talk about y- what you're gonna do, right? And see what they think. Um, in a, in a later stage company, like I'll, I'll pick more, like, Google Photos, which is like a-

    3. HSHarry Stebbings50:21

       Oh.

    4. DLDavid Lieb50:21

       ... you know, larger company. Um, a product review... So first of all, like, often people have these standing product reviews. Like, every two weeks, I wanna hear what that team's doing. Um, I don't like doing it that way. I think it's personal preference, um, but I, I prefer to have it be about specific things, or plans, or projects that they're, that are being done, or decisions that need to get made, where the team, um, has, like, spent a bunch of time on it, they have an opinion on what they wanna 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, like, experts on this project, whether it... So it's basically the leads of every, like, important part of the project, design, engineering, product, sales, whatever it is. Um, and you sit in a room and you don't spend all your time, like, talking about the plan 'cause you probably made a deck or a doc or something about it. So everyone should know what the plan is already. In fact, you should know what it is before the meeting 'cause you should be in the details enough to, like, know what's going on in your company.

    5. HSHarry Stebbings51:20

       Who cre- who created that doc? Where in the scaled-up company now? Is it the PM?

    6. DLDavid Lieb51:23

       Yeah. G- generally the PM. I would say the PM responsible for the thing, if it's a, a product-centric review.

    7. HSHarry Stebbings51:29

       Okay. 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?

    8. DLDavid Lieb51:35

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

20. 52:18 – 55:28

    How to make employees comfortable to speak?

    1. DLDavid Lieb52:18

       a big waste of time, in my opinion.

    2. HSHarry Stebbings52:19

       Can I ask, how do you ensure everyone feels safe to speak? You are, Dave, a product-

    3. DLDavid Lieb52:23

       Yeah.

    4. HSHarry Stebbings52:24

       ... OG. You're, you're very young, Dave, but, you know, you've been doing this for a while.

    5. DLDavid Lieb52:27

       (laughs)

    6. HSHarry Stebbings52:28

       Um, uh, y- 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?

    7. DLDavid Lieb52:34

       Yeah. Yeah. Um, my approach, um, is to try to just be my authentic self all the time. And then people in the room will realize, like, even though maybe I look, like, um, important on paper or whatever, I'm just a regular person. Right? I'm just like you. Um, and I think if leaders who approach leadership that way, with, like, a real authenticity, they're just being th- 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. Um, I think that is the best tool that a leader can use to make everyone feel comfortable and e- able to say what they think. Um, because again, um, 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. Um, so how do you avoid that? You make sure the room doesn't feel like a bunch of important people and it's just normal people. Right? Um, and so I think that's, that's, like, the tool I use.

    8. HSHarry Stebbings53:36

       Do you think Zoom helped that? It removed the, um, the, the fear actually? When you're sitting in a room and you feel that.

    9. DLDavid Lieb53:44

       It's a great question. I, I-

    10. HSHarry Stebbings53:44

        I think Zoom helps.

    11. DLDavid Lieb53:45

        Right.

    12. HSHarry Stebbings53:45

        You're just a square now. I can say what I want. I'm in my home.

    13. DLDavid Lieb53:48

        Right. I, there's a bunch of reasons that virtual makes improvements. Right? The, the one you mentioned, which is, like, everybody gets their own square. Like, that alone is a big deal. Now everyone literally is on equal, uh, pixel, pixel footing (laughs) to everyone else. Um, and you... And some people, you know, interact or, or choo, or, or best m- 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. Um, but I think there are trade-offs, right? On Zoom, I don't know about the meetings you join, but, like, often you just sit there and there's all these squares and nobody says a word until, like, the person running the meeting joins and then everyone unmutes. Um, I think you lose a lot of culture building-... by not having those awkward downtimes, right? Uh, in fact, like when, when, uh, COVID first hit and we had to, like, abruptly switch to all remote, um, one of the... A- and everybody was brainstorming like, "How do you keep your team culture? How do you keep people, like, knowing each other," all that. Uh, the technique that I found, like, the most successful, it's the simplest thing I could think of, is for every meeting that I was kind of like the to- top person in, I would just intentionally show up, like, five to seven minutes late. And I would... I- it creates this awkward silence where everyone's sitting there and a- after some number of minutes, somebody unmutes and says like, "Well, this is awkward, like, where's Dave?" Um, 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, um, culture in a remote environment.

    14. HSHarry Stebbings55:19

        I mean, if you a- had any Brits on your team, we could just talk about the weather from the first minute. So like... (laughs) It's fine for me.

    15. DLDavid Lieb55:24

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

    16. HSHarry Stebbings55:26

        Oh, uh, totally. It usually I mean, I can

21. 55:28 – 58:08

    Where do people go wrong with product reviews?

    1. HSHarry Stebbings55:28

       chat shit for days. Um, a- a- and final one on product reviews, where do you think founders, or not founders, but product leads most go wrong with product reviews?

    2. DLDavid Lieb55:38

       I think m- mostly it is spending time on things that you could have done outside of the room or aren't actually even relevant at all. Uh, so it's, it's really cutting to the meat of what, w- like, "Why are we in this room?" Um, 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 like, "Stop talking. I don't... I've already read your doc, I don't need to hear this." Like, "What I do want to know is what do you think we should do about this question?" Right? Like, "Talk to me about it." Uh, that is a skill that's very hard to master because you're, again, you're like, kind of being rude to a person a- and that's difficult for you, um, 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 wa- on that debate and you fight it out, right? The best product reviews I can ima- I can remember on Google Photos were ones where I had, like, heated debate. And i- 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, um, but we often got to a better answer as a result. Um, if everybody just is the yes man and says, "Yep, we'll do the thing you said we should do," like, you will miss big, valuable opportunities.

    3. HSHarry Stebbings56:51

       Well, f- and sorry, final, final one on product reviews (laughs) . Um, uh, 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?

    4. DLDavid Lieb57:06

       Yeah, um, I mean, I think the simple thing is like, whatever you decide to do in that room, somebody needs to be the singular owner of each of those things happening. Um, and again, this, this, this is probably broader than product reviews. It's more like, how do you run a larger scale team? Um, and what I have found, again, is you lose a lot of value the minute responsibility gets sharded across multiple people. Um, if there are like three people who say they're gonna clean up the floor in the office, who's going to actually do it? Like, it's less likely that the floor gets cleaned when there's three people responsible than when there's one person responsible. So 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, uh, fix the problem. I think that's the way you should come out of all these reviews. Like, who's responsible for each piece of this and, like, when are you gonna get it done by? And, and getting them to sign up for that.

22. 58:08 – 1:01:25

    How has angel investing changed your thinking?

    1. DLDavid Lieb58:08

    2. HSHarry Stebbings58:08

       I think that singular accountability is so key. Final one before the quickfire. And it's, you know, 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've invested in, how has your mindset on product changed through those angel investments and through that portfolio building?

    3. DLDavid Lieb58:28

       Yeah. I guess the biggest learning is companies are very different. (laughs) There are, like, totally diff- I've invested in such a broad scale of companies that like, things that I thought were like, "Ah, that was the reason, like, we succeeded on Google Photos," I then look at another company and I'm like, "Well, they didn't do any of that." Um, and yet their company's worth billions of dollars. Like, wow, there's different ways to solve these problems. Um, I would say y- that's probably the number one learning is, like, there's so many different ways to do this. The things that I found are common across all the successful companies that I've invested in, like, that's an interesting question. What- what is it about these companies? Um, 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. Um, that's one. Number two is that person, usually it's the same person, has to be, like, incredibly charismatic because they need to get really smart, discerning people to choose to work for them when it probably doesn't make any sense for those people to work for them. Uh, that's got to be true. And, uh, what else? They have to approach the world with this mindset that they will succeed. Um, and I would say, like, th- 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." So like, best example, my first angel investment ever, uh, was Flexport, um, I met Ryan Petersen, uh, 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? Like, you do something in tech? Like, we talked." And I left that wedding just thinking like, "I would not want to be on the other side of a competition with Ryan. Like, he will eat you alive." And so when he was raising money, I had said like, "Well, I don't have any money, but I want to invest." So I put like the most I could possibly put in, um, just because I thought he would win at whatever he would... he did.

    4. HSHarry Stebbings1:00:22

       Is, is Flexport your best performing investment?

    5. DLDavid Lieb1:00:25

       Um, from a multiple perspective, probably it will be. Uh, again, you know, who knows until the cash is in the bank, but, um, but I didn't have any money, right? It was a very... it was one of my small... it's probably my smallest check, um, ever, so-

    6. HSHarry Stebbings1:00:36

       Did you, did you write in the same check size every single company?

    7. DLDavid Lieb1:00:40

       Um, well, at the time, I, it was, there's one company I could invest in and I have no money (laughs) 'cause, like, we hadn't yet really gotten any liquidity from Pump. Um, so that was, like, the only company I could invest in, right? Uh, later on, yeah, I- I've generally tried to keep my check size r- reasonably static, um, because, I don't know, there, there's lots of different opinions on this, but, um, it's very hard to know upfront which companies are gonna be successful. And in fact, o- often your gut, um, will tell you the opposite. (laughs) This is interesting. Will tell you the opposite of what actually will happen. The companies that seem the stupidest or the craziest and you're just like, "Ah, I don't know, but I like the founder. I'll invest," those are the ones that turn out to be big wins. So if you modulate your check size based on, like, probability of success

23. 1:01:25 – 1:03:24

    How to judge founders that are technical?

    1. DLDavid Lieb1:01:25

       or, like, how big the market is or whatever, you'll probably be doing the exact opposite of what you should do.

    2. HSHarry Stebbings1:01:30

       That's why the transition from angel to venture is fucking hard, 'cause you don't write those checks. When it's like, ah, doesn't make sense.

    3. DLDavid Lieb1:01:37

       Right.

    4. HSHarry Stebbings1:01:37

       But good people, cool.

    5. DLDavid Lieb1:01:38

       Right.

    6. HSHarry Stebbings1:01:39

       You, you can't do that. Or you can-

    7. DLDavid Lieb1:01:41

       Sure.

    8. HSHarry Stebbings1:01:41

       ... you can and the best do, but it's very difficult to do. Um, but, uh, sorry, I just have to, uh, pick on one thing. You said about the charisma there. You know, when you look at the next generation of founders, often building developer tools, API economy, respectfully, they have the charisma of a lemon, um, or a pineapple.

    9. DLDavid Lieb1:01:56

       (laughs)

    10. HSHarry Stebbings1:01:56

        I mean, they are the most uncharismatic people in the world. And, uh, uh, it's not the storyteller -

    11. DLDavid Lieb1:02:04

        Yeah.

    12. HSHarry Stebbings1:02:04

        ... that can -

    13. DLDavid Lieb1:02:04

        Yeah.

    14. HSHarry Stebbings1:02:04

        ... create ... So how do you think about that? 'Cause I worry that I'm gonna miss the next generation of specifically developer and engineering-centric founders-

    15. DLDavid Lieb1:02:12

        Yeah.

    16. HSHarry Stebbings1:02:12

        ... because they can't tell a story as well.

    17. DLDavid Lieb1:02:14

        I, I would say charisma is in the eye of the beholder, right? It's not a uniform thing. Um, you put me in front of a group of people who are gonna be the best in the world at building dev tools, they might think that I'm very non-credible. They might look at him and me, me and, and say like, "Yeah, he, like, seems like a slick talker, but, like, I don't believe him about any of these things." So I think it really is in the eye of the beholder. Um, what, why does charisma matter? It's so you can hire the best people in the world at this problem and so that you can get the customer to, like, listen to you, um, or, or like figure out a way to message to the customer such that they will listen to you. Um, that's very specific to, to various domains. So I think you can be what some people might call, like, very non-charismatic or uncharismatic, but be, like, very charis- charismatic to the group of people you want to hire.

    18. HSHarry Stebbings1:03:05

        Bugger. (laughs)

    19. DLDavid Lieb1:03:07

        (laughs) Well, it's good news, um.

    20. HSHarry Stebbings1:03:08

        It isn't... Eye of the beholder is not good news. That means that I am-

    21. DLDavid Lieb1:03:11

        (laughs)

    22. HSHarry Stebbings1:03:11

        ... shallow and, uh, uh, purely gravitate towards the sales CEOs. Good.

    23. DLDavid Lieb1:03:15

        Well-

    24. HSHarry Stebbings1:03:16

        We're not -

    25. DLDavid Lieb1:03:16

        It means that you need to know your audience, right?

    26. HSHarry Stebbings1:03:18

        This is-

    27. DLDavid Lieb1:03:19

        That's the whole-

    28. HSHarry Stebbings1:03:19

        This is totally true. Listen, I wanna move into a quick fire round. So I say a short statement, David, and you give me

24. 1:03:24 – 1:05:15

    Did you really get fired from Google twice?

    1. HSHarry Stebbings1:03:24

       your immediate thoughts. That sound okay?

    2. DLDavid Lieb1:03:26

       Okay. Okay. Well, yeah. Let's see.

    3. HSHarry Stebbings1:03:27

       Did you really get fired from Google twice?

    4. DLDavid Lieb1:03:31

       (laughs) This is the first question to the quick fire round? My God.

    5. HSHarry Stebbings1:03:33

       A little bit, yeah.

    6. DLDavid Lieb1:03:35

       Um, I didn't get fired from Google. Um, I did get asked to leave the team twice. Um, and so this is a s- I'll give the shortest possible version of this, like, story as I can. Um, in the early days, right after we got acquired, um, 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+ social, like, building a social network track. Uh, there was vigorous debate. The, it turns out the person that we reported up through w- sided on the, "Yeah, we're doing the social thing. That's what we're doing." And, um, 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 wanna do. Um, if you talk to anybody I've ever worked with, I'm very bad at doing that.

    7. HSHarry Stebbings1:04:29

       (laughs)

    8. DLDavid Lieb1:04:29

       Um, it's very hard for me to do something that I don't believe in. And so I just decided I'm not gonna do that, and I basically just told everyone, like, "No. I'm gonna keep building this with these people on the team. Um, so sorry." Um, and I did that because I, like, had a unique situation. We got acquired, like, 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." Um, and again, I just didn't take no for an answer. I called up a bunch of people that I knew, um, in the Valley who had the ear of Larry and, uh, other folks on the board and, um, that, I think, was at least part of the reason (laughs) why ultimately we changed our minds as Google and decided to build Google Photos.

25. 1:05:15 – 1:06:19

    Do you still have a chip on your shoulder?

    1. DLDavid Lieb1:05:15

    2. HSHarry Stebbings1:05:15

       Do you still-

    3. DLDavid Lieb1:05:16

       So, yeah. (laughs)

    4. HSHarry Stebbings1:05:16

       ... have a chip on your, do you still have a chip on your shoulder? You've said multiple times about it. Do you still feel-

    5. DLDavid Lieb1:05:20

       Yeah. It's a great question. I don't feel it anymore.

    6. HSHarry Stebbings1:05:24

       Yeah.

    7. DLDavid Lieb1:05:24

       Um, I don't feel like I need to prove that maybe our, our startup was worthwhile, like it was good that people invested millions of dollars in our startup. Um, I don't feel that I need to prove that I could, like, build a product that people love, like I've done it. Um, but there's probably other domains where I do have a chip on my shoulder. Like, I'm about to join YC, right? And, um, you know, try to help th- 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.

    8. HSHarry Stebbings1:05:52

       What are you most nervous about that?

    9. DLDavid Lieb1:05:55

       Um, what am I most nervous about? Well, you, you, you, like, highlight my track record as an angel investor, but the dance is still going. The, the game is still on. So who knows if, if I will actually end up being a good angel investor or not. You don't know for decades, right? Um, I think that's probably one of the things I'm most nervous about, is YC is really good at picking the best companies, um, and I feel a little bit of, like, I don't know, imposter syndrome going

26. 1:06:19 – 1:06:46

    Which product leader do you most admire?

    1. DLDavid Lieb1:06:19

       in where it's like, "Am I a- actually any good at this? I don't know, I, and I wanna learn." So that'll be fun.

    2. HSHarry Stebbings1:06:24

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

    3. DLDavid Lieb1:06:29

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

27. 1:06:46 – 1:07:08

    Advice for new product leader

    1. DLDavid Lieb1:06:46

    2. HSHarry Stebbings1:06:46

       I actually have him on the show on Friday, so I'm wonderfully happy-

    3. DLDavid Lieb1:06:48

       Oh, awesome.

    4. HSHarry Stebbings1:06:48

       ... to hear that.

    5. DLDavid Lieb1:06:49

       Oh, that's great.

Episode duration: 1:08:50