I'm Jessica Livingston and Carol and Levi and I are the social radars in this podcast. We talked to some of the most successful founders in Silicon Valley about how they did it. Caroline and I have been working together to help thousands of startups at Y Combinator for almost 20 years come be a fly on the wall as we talk to founders and learn their true stories. Today, we're talking to David Lee. I'm thrilled to say has recently joined Y Combinator as a visiting group partner. If any of you were around Silicon Valley in 2009, you might remember a cool new technology where you transferred your contact info from one person to another by literally bumping phones. Well, David was one of the founders of Bump Technologies. He'll share bumps ups and downs as they went from business school side hustle to Hot new IOS App to ultimately transforming into the wildly popular Google Photos. Enjoy. So we're here with David Lee. We're so excited to have you, David. I want you to tell me because I was talking to Caroline saying I remembered when we interviewed Bump back in, it would have been 2009.

We were all so excited during the interview. You had great technology but I think you might not have like, you almost didn't do Y con, right? What happened?

It was wild. I mean, we were total nubes. We didn't know anything. And so yeah, we applied to YC. I think we heard about YC because Jake and I, two of the three founders, we were like former engineers, but we had gone to business school, which we'll talk about later. But we were reading techcrunch, techcrunch was like the hot thing back then and we were like, what is this thing called? Y Combinator? Everybody keeps talking about it. Maybe we should like research that for our little project that we're working on and turns out we knew,

we knew one person who had done YC or maybe two people say average from, from New Bridge, from college, from Princeton. Right. Yeah. Yeah. And he had done it and he said great things, obviously. So, yeah, we came for the interview and it was great. But afterwards, you know, we were like the hot startup, we had millions of users.

All the like, bcs were trying to network with us but we didn't know anything. We were just like two or three kids but, and er, third co founder, he's 10 years older than we are and he had done a startup already. And so he had all the like, you know, old school vcs coming to him saying like that's a horrible deal. Why would you do? I see like that's dumb. You should just go raise your series. A and yeah, so we, we were pumped about it. But then all these advisers were telling us like you're idiots. Why are you doing this? So it's really hard to work through that and then separate the like signal from the noise because like everybody obviously wants to tell you what is best for them, not

what's best for you. The vcs. If they could catch you before, why Combinator, they'd be much

happier. And so I distinctly remember I had a phone call with Paul PG and I remember him distinctly saying the sentence, there's no way for me to prove a priori that is going to be totally worth it. But it will be. And I'm like, that's a difficult argument to make like, it's not very convincing to me because I don't even, I don't know you. Like, I think part of it was that we were outsiders. Like we were not students of P G's blog when I heard about YC. Actually, the first thing I did was I bought your book and I read founders at work just to like, learn about this space a little bit in hindsight. I look back and I'm like, oh my gosh, we were such like, we had no idea what we were doing and you can kind of see like some of the things we did, like obviously we didn't know what we're

doing. Wait a second. I now have a ton of questions first. Let me just interject though that I think the vcs are very shortsighted to think that startups are not better off doing Y Combinator because I think in the long run we offer

so much. Yeah, I think now that's very proven for sure.

Right. Yes. What tipped the scale? What made you say? Okay, we're going to take a chance on Y Combinator.

So we talked to serve Raj and I think he was in the batch with, with Dropbox if I recall correctly. And so he told us like he, you know, he like, I think he connected us with Drew and like, I don't know if we ever talked to Drew, but like we've learned about Dropbox and I think there were enough positive signals from doing that very quick diligence. I guess you would call it that we decided. Okay. This sounds pretty great and everything we've heard from all these people sounds like it's in our best interests compared to some of the other experiences that we had where vcs or other accelerators or whatever would come talk to us and we would leave those conversations just thinking like that. That's something that all right. So there was definitely this like gut spidey sense. I guess that YC was probably

going to be a good idea. Thank goodness for your spidey sense. Is all I have to say. The three of you were, did you, were you in total agreement or was Andy a little bit? Like, you know, I've been down this road, maybe I don't need it

or like, how did that work out in the end? Yes, we were in total agreement. I think we were like, very close and very good decision makers together. But I would say Andy was the one who was getting bombarded by all these people that he knew, They heard that he was doing his second startup and they were like all the people that he knew were just saying like you're gonna give up how much equity for how much money. And of course, this was back at the beginning of YC. So I think we got $6,000 per founder I think was, yeah, I found a photo I took of the Czech recently. So he was just getting bombard by all these people and he was just trying to communicate to us what he was hearing from people. And so, you know, for me,

I still to this day very much look up to and he was kind of like my mentor, I guess and yeah, when your mentors telling you like, everybody I know who's smart is telling me this is like a dumb thing to do. Like, should we talk about it? I think that was the challenge for us. Thank God that like, you know, we did it.

Yes. Let me dig in just very quickly. So you knew Andy, who was like 10 years older than you from Texas instruments. Is that right?

Yeah. So T I was working at T I, that was my first job out of grad school. And T I acquired Andy's previous startup. It was a hardware technology, was a chip technology to build micro mirror devices on a chip. And so when we acquired this company, this is the first time I'd ever seen an acquisition. And so that was also new to me. I researched, I like looked up Andy on the internet and I'm like, oh, he went to Princeton. So did I like, I should befriend this guy. Maybe I can learn something from him. So as soon as they got acquired,

like he and I started talking and I think we were very aligned on a bunch of things we wanted to do in our lives and we worked together a bit at T I for maybe like a year or two before we both decided to leave. Actually, I was gonna go to business school and Andy was gonna leave and like, actually wanted to do another startup. And on the last day at T I, we had lunch. Actually, I remember very distinctly and like, I didn't know him super well, but we worked together a bit and I said to him like, hey, one day, I think I might want to start company to like, maybe we should do it together. And we kind of both jokingly said, like,

sure, like, you know, later on we'll get in touch. And then I went to business school and had the idea for a bump, like, literally four weeks later I think, and I emailed him back and like, hey, about that lunch where we said, like years from now, maybe we'll do a startup. Like, how about right now? Um And so yeah, that was a funny turn of events.

So, so you then went to University of Chicago to get your M B A from T I. And that's where you met the third founder, Jake. Yeah,

that right. It was, yeah. So in business school, if you're an actual engineer, which which both Jake and I were, they kind of ask you like, do you know anything about finance or accounting or any of these things? And of course, our answer is like, no. And so they invite those people to do this. I don't know what it's actually called the we called it remedial accounting which is before business school starts, they ask you to come and learn the basics, right? So Jake and I were part of that class and at the beginning of the class, you like go around the room and say,

you know where he used to work and what your background is. And he said he worked at T I at the Dallas Texas location. And I'm like, I lived a mile from where you worked and like, I worked at a different location, but we didn't know each other. So afterwards we like, went and talked to each other and got to know each other and we both wanted to do stuff in tech. And so we hit it off and then when we started working on Bump, we worked together.

So, were you working on Bump whilst going to

business school? Yeah, literally like the idea for Bump Business School started. And I think I like wrote down on my little piece of paper, the idea for Bump. Like two weeks later, it was really at the very beginning of business school. And it's because I was facing this actual problem in my life, which was I was meeting all my new business school classmates and we were all exchanging phone numbers and names to type into our brand new shiny iphones. And I just, at the time, I guess I was naive and I thought, oh, why doesn't anybody solve this problem? Like, gosh, it seems like we could solve that. And so we started working on that little side project just to like make our lives easier.

And then it turned into something more surprise, surprise. So many startups start like this.

It was totally a side project. You know, you hear about a lot of these great startups that start as side projects for us. It was so we could like go, it might be fun. I had heard actually a story of another student at University of Chicago. He's now an engineering director at Google who had in the summer when they opened up the App Store for the very first time he wrote an app that would look for wifi networks that were open and didn't have a little like firewall or whatever we have to type in a capture or something. And he put it on the app store and sold it for $4 that summer. And he made like $100,000 that summer. I heard that story and I was like, Oh, I could pay for my business school expenses by like making an app. So our goal at the beginning for bump like literally, I, I think I told my dad, I was like, I think I can make $25,000 doing this app that like,

it'll be cool. And of course, like, you know, it was more than that

later. So. you built it because you yourself wanted to use it. But you also thought, hey, I could cover a lot of the costs of being a student here by making some

money from the store. Yeah, I thought I thought there was a chance that like, maybe you could make some money on this thing. But the idea of making something that millions of people would use and love like was never even on my mind. It was a total side project. So Jake and I were in school, like full time students, but we took, you know, business school, we were engineers, at least at the beginning, it wasn't like super hard for us. So we had a lot of extra time and Andy had just quit his job, so he had no job at the time and we just worked on it as a side project like every night at nine pm, Central time in Chicago and seven p.m. pacific time,

we'd all like get on Skype at the time and like talk about what we would work on this week and this weekend and every weekend we would decide, like, should we work on it more or are we done? And that happened like every week for, you know, 30 weeks. And then we finally decided like, ok, let's launch this. I think people are gonna really want to use it. So when

did you launch? Then

It was the spring of 2009. So we started working on at the fall of 2008. And so in part time, it probably took us like three or four months to build it. I guess. I remember we submitted it to apple on Valentine's day 2009. That was like the moment we submitted to the app store and then we heard nothing crickets, no response, nothing for apple for like a month. And I thought like, this isn't this doesn't seem right. I see other apps getting, you know, approved quickly and it turns out in hindsight, what had happened is we got like accidentally filed into some purgatory area in the App Store review process and this was very early in the App Store review process. So they were still figuring out like all the processes I decided. Alright.

Well, I gotta do something about this. So I went on to all of my alumni databases. So I had gone to Princeton, but then I also did a graduate degree at Stanford and I went into all the databases and I tried to find the high the most senior person at Apple who went to one of my schools and I found that Scott Forestall went to Stanford and I got his Stanford alumni email address through the system and I just sent him an email. I'm like, hey Scott, like I'm a student. I also went to Stanford. I submitted an app to App Store, but like, I haven't heard anything just wondering if you could like help out. And um he wrote us back and he said it's going to be resolved and like within a week our app was approved. So it's just like, wow, these things actually work. Okay.

So now it's spring of 2009 at the same time you're applying to YC. Yeah, at some point you said, Okay guys, we're gonna drop out of school and get serious. About this. Yeah, that's

certainly one of the paths that we thought it could take for Jake. And I also though it was like, in business school, you do a summer internship right before your second year. And neither of us had any interest in doing the normal summer internships that all of our classmates were doing. And so for us it was like, oh, we can work on our startup in the summer. If it fails, we have a nice option to go back to school. And if it works, like we can defer and go back to business school the next year or the year after that. So for many years, we, we would tell the school like, oh yeah, we're still working on it,

but like next year we'll come back next year. And after some number of times of doing that, we realized like, oh, that's not going to happen. But the school is really great

and gracious. Oh my gosh, that was by the way, the original vision for Y C is that people would work on the startup in the summer founders program. And then if it didn't work out, they could just mothball it and go back to go back to school.

I just remember we applied to YC before we had launched. Oh, and then I remember sending you, I think you specifically, I sent an email saying like, hey, I wanted to give you an update. We launched our app and by then we had like a million users or something. And so I think that was a big shift in in the the application process

for us. Okay. Yes, a million users. That was pretty rare back

then. Very rare. Yeah, the app took off pretty much immediately. Very much surprising

to us. Europe says that you are looking to make bump a verb like Google, let me bump

you. I would say we achieved that. Actually, at least for some number of years.

Then you and Jake moved to the Bay Area for the summer. You participate in YC. Any highlights from that summer that you remember?

Oh gosh, so many, I mean, all the speakers now, in hindsight, I realized these were like luminaries, right? Like the idea that Mark Zuckerberg would come to our dinner like, wow. So yeah, that was definitely memorable. I have personal memories of walking down pioneer and like going to r we had an office right by Y C. That was our first office that we got. And yeah, so many fun moments just hanging out the YC office, going back into the back with Trevor's robots and all these fun things in terms of why see itself. I would say I was looking back through my emails and I would say we underutilized it honestly,

like in hindsight, I wish we had had more office hours. I think we had like five office hours with PG the entire time. That was it. I don't think we met with anybody else really. We didn't really tap into the alumni network even though it was already very big at the time. So in hindsight, I wish we had utilized it more. And so that's the thing that I've learned now upon joining. Well,

also it was before book face was written.

Yeah, it was, yeah. To book office hours. I think you just emailed PG. Yeah. And then he would say like, oh I put some more on the

system. So it wasn't really your fault. We didn't have all the systems that are in place now to let you take full advantage. Now that I do vividly remember a story where you did take advantage of the alumni network and that was the advertisement on Dancing with the Stars. Tell Carolyn

that story. Yeah. So Apple, after not approving our app for a long time, they did approve it and they took a liking to it. I think it was a great example of the cool new things you could do with an iphone and people loved it and it showed developers what you could do with it. So they wanted to promote our product as a way of promoting their product. And so we got a relationship with Apple. We had actually turned out randomly actually that we were the billionth app downloaded on the app Store. Kind of just by chance like if you looked at the chance of the being downloaded that day. I think the probability of us getting it was actually more like one in 200. So still a very small chance, but not like one in a billion. And so we got a relationship with Apple from that. They, like, they called me one morning in Chicago.

They were like, hey, your app uses servers, right? And I said, yeah, and they said we're gonna tell the world that you were the billionth app downloaded. So you might want to like call your server guy. So I like I called Andy up and I said, hey, are we gonna be okay? And he said, no, we're not going to be okay. But I didn't know what to tell Apple, I couldn't tell them like,

don't promote us, right? So I just told Andy like, okay, let's do what we can and maybe it'll crash, who knows? And I think we survived that first day. But then Apple took a liking to us. And so they got us to sign this piece of paper saying basically it's okay for them to use our app assets in whatever materials they wanted. We didn't really understand kind of what this was. I think we actually talked to John about this. Like, should we sign this? I don't know. So we signed it and then we didn't really hear anything. And then one day I think it was in August.

So it was right around demo day actually. Um in August that, that summer we were in the office. It was like eight p.m. and I started getting text messages on my phone, like instantly from friends and they were like, I just saw you on, on during dancing with the stars. And I'm like, what are you talking about? I don't, what do you mean? Uh And they said you were in an Apple TV commercial during dancing with the Stars. And then of course, in our office, like we had a dashboard on a T V and the dashboard went like this and then just a vertical line like straight up and of course, everything crashed,

the system could not handle that traffic and we were down and we were totally screwed. We didn't know anything about how to fix it. Like we were, the backgrounds of the three of us are too two semiconductor background people myself and Andy and then Jake who was like a semiconductor sales and marketing background person. So we didn't know software really. So we were like very much out of our element. So we emailed the YC founders email list at the time. There was no software for it, but it's just an email list like a Google group. And we emailed it and we said, hey, everyone we were on during dancing the stars were screwed. Our servers crash. Does anyone know this technology stack? I don't remember what it was. Some Apache thing that we had and very quickly,

Alex Paul Vi from Cloud kick an alum. He was like, oh yeah, we're experts at that. Where is your office? So I like gave him the address to the office and they showed up like within 30 minutes and I remember very distinctly came in the office and they said, step away from the keyboards. So we just like walked away

a to the rescue

and

fixed it. He really said step away from the keyboard.

Yeah, it was so great. Take a seat. It was like a scene out of a movie. It was so great and

they fixed it, they fixed it. That is so great. That is

great. So that alone paid for our YC solution, right? Just that one moment probably

was worth it. That's awesome. That's a great story. I love magical alumni moments where people help each other out like that. That must have been the first season of Dancing with the stars by the way, because that's a long time ago. That show's been on forever.

Yeah. One time dancing with the stars. Yeah, that's, yeah.

Okay. So then what happened to bump?

Well, a lot of things happened, I would say the general story is we had a ton of users. We go about 150 million people to install our app. We had 10 million people who used it every month. We had one or 1.5 million people who use it every single day. So we were feeling really good. All of our graphs were going up into the right. We were getting inbound, unsolicited interest from Mark. And the reason for our series B like raised money from Sequoia. We were hot and then years like a year passed and we just kept building stuff and we realized that the graphs are kind of slowing down a little bit. And we just said to ourselves, like, because we've got like all the users in the world, like, of course,

they're slowing down. That's, that's what happens. And then we dug into retention a little bit more deeply and we dug into frequency of use a little more deeply. And what we realized was, oh people keep using it, but they use it pretty infrequently, they use it, you know, they keep it on their phone and they'll use it like a month from now for like two months from now, but they're not using it all the time, which we thought like, well, that's probably okay. But what we learned was if you want to have a business model where each interaction is not super valuable, then you better have a lot of interactions so that you can monetize it in some other way where the interaction value is very low but spread across a ton of interactions.

And we were like, if you made a two by two grid of those two things like frequency of interaction and value of the frequency of the interaction. We were in the quadrant that you do not want to be in which was low frequency and low value. And so sometime in like 2012, I would say is when we really internalized that and thought, oh crap, we are screwed. There's, there's no business that's going to work here. And we tried our best, like we tried every single idea you could come up with for monetizing bumps. We had ads, we did up sales in the app. We had digital goods, we would let you buy and they kind of got us to a point where we could probably have become profitable, like barely if we like cut our staff a bunch.

But we saw no path where it would be like a venture returnable type of company. Like it was not gonna be hundreds of millions of dollars of company. So we, this is like the most transformational day of my career I would say is Jake and I decided like, alright, what would PCI tell us to do? And I remember he would say like, go talk to your users, like when you're screwed, go talk to your users, that's what you should do. So that day I emailed the top 100 users of them, like the people who used the most emailed 100 of them. And I said, could you please talk to me today? And I think like 12 of them or 15 of them or something wrote me back.

And so we called those people all day in the conference room. Jake and I, and what we learned is they were using it to share photos with their friends and family. And that was an insight that we did not get from the data. Like you don't see that on any graph, right? The graphs that you have are all aggregate data. They don't tell you exactly what's going on. So we heard those insights and we were like, huh that seems really valuable. They're using it frequently and it's like actually a problem they care about. But this product is not the right product to build for those people right there, like using it despite the fact that it's um you know, built for something else. And so that led us to to go build another product that was around photo sharing. It used really all the same technology that we had built it bump,

it just applied it in a slightly different way. And so we built that app, it was called Flock and it was intended to help you kind of like automatically share photos that you take with the people that you care about in your life. And we were very excited about this app. We used it in a in a beta. We got a bunch of life, see people using it. It was awesome. Everybody was using, it was so great and we launched it and like nothing happened no one downloaded it. We couldn't get people to use it. And so it was the opposite of the Bump effect where Bump had a network effect. Right. The chicken and egg problem. But Bump was so physical and so novel that it actually turned that liability into a big asset because people would go tell their friends about it. Like,

hey, have you seen this new cool app? You've got to download it, go download. It would force people to download it For Flock. It was not cool enough and not immediate enough. And it was later where people were kind of like over telling their friends about cool apps to download like this was 2012. And so it the chicken and egg killed it. Like there was, there was no way it was going to grow

you to use Bump for the photos even though you had built flock. Like were they still doing this off label use

with Bump? Those people never got flock. That was how bad the

growth was. They didn't even bother like they just, but did they keep doing the photo sharing thing with Bump?

Okay. Because it was like the only solution that they heard about? Yeah, the problem with Lock is you had before you could use it at all. You had to go convince all your friends and family to download this photo sharing app at the time. Nobody wanted to download another photo sharing app. It was just beyond what people wanted to do. So we learned something very interesting from that, which was a separate app is not going to solve this problem. Like you've got to be the camera roll app. And so we like had that insight. And I think over the course of like a week we built and designed a new prototype, which was basically what would turn into Google Photos. And we had this thing and we were like, this is the answer. Now, we know like,

boy, we spent four years doing this. Now, we understand like the future, this is the future and then we realized building and launching that and like storing All these photos. If we were successful, that's going to be very expensive. We better have like a real business model either from the start and we've got to raise a lot more money. We already raised $20 million. And so we had this decision point where we were like, are we going to go raise more money for this? And will we be able to raise more money for this, this totally new unproven idea? And our answer was like I wouldn't put money into that startup. That seems risky.

Did you ask any of your investors to what

they say? We didn't, not explicitly, at least I think by that point, all the investors had kind of like communicated to us that like you guys have given it a good shot either figure out a way to monetize bump and make it valuable somehow or like, it's not like there's nothing more here, but we had a lot of conviction that that new product, that third product would really work. I remember we, I put a calendar event on my calendar for September 15th, 2012. So this was right. Like we launched Flock that summer, it flopped. Nobody used it. And I put a date on the calendar and that was the date I had to decide if we were going to sell the company or keep going as an independent company. And I did it with enough runway.

I think it was nine months before we would run out of money just so I could like, figure out what to do. And on that day I sat down and I was like, we're going to sell the company. That's the right path. And that kicked off a whole another process which was like, go sell a massive property on the internet and see how much it's worth. Right. And we had no idea what it might be worth. So the first step was like, is anybody going to pay for bump? Because we had a ton of users and a ton of usage, right? It was bigger than so many popular apps that you've heard of. And that was a fun exercise. The answer was basically the people who had money didn't value the user base and the people who value the user base didn't have any money to spend. And so that put us in a tricky

spot. Can I just quickly point out how impressed I am by your discipline, marking a date in the calendar? This is the day I'm going to decide what to do. Not only does that imply that you were not in denial, but you were actively going to take control of a decision either way. And I think that's sort of a very subtle thing for founders to think about because I've seen people just keep going and they need to the calendar,

I guess I would call that like, I eventually did the right thing, but like, I should have done that a year before or two years before. And I think this is a great example of, you know, we raised a ton of money because we could. And whenever you do that, of course, every founder says, like, well, I'm very disciplined, I'm going to just put that money away. We're not use it, we're going to figure out our business and no one does that you always have new ideas and you're like, oh,

if we just could do this new feature, then it'll work. And so we did that for like an extra year or two. And I wish we had had this kind of insight moment earlier before we had raised so much money and before we had spent so much time pursuing a particular path. Yeah, this is a great example. Like in hindsight now, I'm like, how did Y c not push us on the business model? And the answer I think was at the time, all the popular startups that were really succeeding were the Facebooks of the world, the Twitters of the world where they were, like, we'll figure out monetization later, it'll be some sort of ad based thing and it'll definitely work. And so I think we saw that we were like,

well, what's different about us? Like it'll work too for us. Let's just do that. And of course, in hindsight, we realized we were in that bad quadrant of the graph and it would not work for us. So I wish we had figured that out earlier in hindsight,

but it took you like several years to figure that out. Yeah, like during Y C you were still getting users, let me just state you're still getting users.

Oh yeah, for sure. Oh no, we grew like crazy. Yeah. At some point we were on, I think one out of every five phones in the world full stop. Like that's how big we were. But yeah, we just didn't have a business model that was going to suit the way the product was used. So people ask us like, did you have product market fit? It's a weird question for me because the answer is like, definitely in some ways, but it's easier to have product market fit. We have a free product that anybody can use without like paying in any way.

Yeah. Okay. So you're going around talking to potential acquirers, you're not finding a good fit for that. How did Google come into play?

Well, the first thing I did was I did this like tour of Asia with one of our investors from injuries and to just figure out if any of these big companies in Asia where we were very popular, like we were the I think number two app of all time in Japan, for example, we wanted to see if any of them would really value what we had. So I like went on this whirlwind tour over there and you know, the answer was they were all very interested, but they just didn't have budgets to buy companies in the way that the Silicon Valley giants did. So we kind of did that whole exercise and then we were back to square one. Well, that's not gonna really work. And so we kind of narrowed it down in Silicon Valley. Like which company do we think should have this product? Like where would it make sense? And the obvious answers were Apple to replace their photos app, Google to replace their what would eventually become their photo app or companies like Facebook, maybe,

maybe they could pivot to something like this. I think those were the top three contenders. But yeah, then we went to all of them and basically the pitch to all these companies at that point was, hey, Bump is big, maybe it's useful to you. But the real answer is this photo app is going to be the winner. Like I'm certain of it. Let me explain to you why I'm so certain of it. Do you want that to be yours? That was kind of the pitch. And we got a lot of great interest. Of course, the way it eventually played out is Apple wasn't, but they did not want to pay for it.

And this is like typical Apple approach. You know, I remember, I remember calling the head of corporate and Apple once they've given us an offer, I said, hey, your offer is great. We'd love to come to this. But like your offer is literally one half of the offer of other competitors. And the answer was like, we want you to want to work at Apple. That's why it's lower, it's intentionally lower because we want you to want to work at Apple. And I was

like, it's like a mind

game. Yeah, I was like, but my investors don't want to work it out. So, yeah, so at the end of the day, the clear D N A fit, the clear mission fit was Google. It was just very obvious to me that this is where we should build this. It would allow us to build it on both platforms and not just one of the platforms, there wouldn't be any weird pole towards like social with Facebook or whatever. Yeah, who would have maybe pulled us towards. So that was like the obvious answer. So we were feeling pretty good about it. We had like recovered this crashing airplane and we were able to get it like a nice soft landing for investors and a potential big future for us to go build at the company.

And then there was a reorg at Google. So in the time between when we signed the deal and when we showed up, it was like a three week period, I think, you know, when the lawyers were doing their thing, I got a message saying like, hey, you know, we did a little reorg Google. Now, all the photo work that we're doing is no longer in the Android group that reported up to Sundar at the time because now the CEO now it's being moved over to the social team, the Google Plus team and

I was like, oh my God, Google

Plus. Okay. Now, in hindsight, I'm like, oh, reorders are a big deal. You should really investigate that before you sell your company to someone. And yeah, we showed up on day one and we reported up to a different leader and I said to that person and I said, hey, we're, I'm here like, I'm Dave from bump team. Um I got my whole team here. We're gonna go make this app like good to meet you and this person was like, no,

we're not doing that. Welcome to Google Plus, we're building Google Plus. And I was just like, oh boy, were

you just crushed? You must have just been crushed.

I think what made it worse is that I had like, you know, been using to some extent Google Plus and I knew that it was not working and I did not see any path by which it was going to work. And once I got inside of Google, I was able to look at the data and it was even more clear to me like they were in denial that it was going to work in, in any way. So that made it worse. Yes. But at the same time, I don't know, I like a challenge, I guess. And so I was kind of like, all right, let's see what we can do here that like first nine-month period from when we got acquired to like the summer of 2014, it was basically me just fighting with people internally. It was like very difficult period.

I would say. Now, did I read somewhere that you like got fired twice?

Yeah. Fired is probably the wrong word. I was asked to not work on that team anymore twice. Yeah, like I was told to go home. So the backstory is the clear direction from all of my bosses was we're gonna go build Google plus and you're, you're going to work on the photo part of Google Plus. Like your job is to do all these things to help people post more photos to Google Plus because that's the, that's how we're going to get people to use Google Plus. And I said like, okay, cool. I'll do that job like on Monday mornings and then Monday afternoons through Friday, I'm going to go design the new Google Photos. Okay. Uh And they didn't say okay, they said no,

we're not doing that. And I said, okay. And then I went and did that with one designer and we basically spent all of our time designing the new guy. And within like two or three months, I think we had kind of like a great idea of what it would look like having taking what we had from bump and rebuilding it with all this new great Google technology. And we went to the bosses and said like, okay, we've been doing our job but like, here's the new thing, what do you think now? And they were still like, no, we're not gonna do it that way. Like that's not the approach. And so I said,

okay, I'm gonna just keep doing that okay. And they were like, no, not okay. And I said, okay, well, I'm gonna do it with all these engineers and designers. See you. And yeah, I was told basically at some point like, no, you may not do that. Like, in fact,

you're now off the team uh and so they told me to go home, like, on a Monday, they said, like you're done, go home next week. We'll figure out what other job you can do inside of Google. And for me personally, because we had been acquired, I kind of knew that, like, they're gonna pay me my four year retention bonuses anyway. Like, even if they literally fired me, there'd be some sort of way to suit them or something. And I would like,

get my value. So my downside was very low. Like I didn't want a career at Google. Like it wasn't like I was gonna go apply for a job at Google necessarily. So I had an ability that a lot of my peers and my teammates didn't have, which was I could kind of just burn it to the ground and like the downside is very low for me. So I decided like, well, everyone here wants to build this product. I'm kind of the only one who can go for it and have no personal downside. It's kind of my duty almost to do it. And like, as a shareholder of Google in hindsight also, I'm like, I think that's the right thing to do for Google. So I'm actually like,

proud that I did it. But yeah, I was removed from the team. Um It was, it was a big mess. Eventually the right decision happened and we can get into that. It's interesting, but finally, we were able to build Google photos

and it worked well. So they sent you home for insubordination for a week and you came back, you're like, I'm still gonna do it. Like, how did that all work

out? Well, so the short answer is, yeah, I was sent home on that day. I made some phone calls. I was like, all right, well, let's go. We're not enough like we're escalating the situation. So I decided, well, it's my turn to escalate to. So I called some people that I knew in the valley, some of whom were early investors in Google, some of them sat on the board of directors at Google somewhere like personal friends with Larry.

And I basically just told them like, hey, here's the situation, here's the product that I think we should build. Here's what I know about how it's going internally on Google plus, take these data points. Tell me like, it would be great if you could go talk to Larry and make sure he's aware and has decided that this is the direction he wants to go. And I think what happened is that those conversations happened and I think Larry decided like, oh, that's what's happening here. Like, no, we shouldn't do that. And he fixed it basically like within a month it went from, oh,

I have no future at Google is not going to work to, okay. We're building Google Photos. You're a separate team now you're not like beholden to that person. That person actually now was gone from Google within a month of that conversation. And we reported up to a person took to my boss at Google who was like very much on board with building this and was a key contributor to like helping me navigate all the politics of it. And at that point, it was just us and our team and we could go rip and it was like, that was the best moment, like the best time in my career, I would say where we just built Google Photos and there was no holding

us back. David. I kind of feel like you were like this canary in the goldmine of like new bad boring Google. I feel like someone listening to this should take notes and say, let's keep the David leaves happy and if we can keep people happy who have like a great product sense and are driven, then Google will flourish. Because one of the things I wanted to hopefully talk to you about today is just Google. Like we've all heard so much about the early days. And in fact, on the series, we interviewed Paul Blue Kite heard a lot about, you know, when it was back in the days of employee 23, but now later on Google, just it sounds like you were fighting this bureaucratic headwind almost the whole time until it to the tide changed because

of Larry. Definitely. Yeah, I would say, like if I had to summarize what I learned and how I saw Google change over the nine years, I was there, I would say the number one thing was actually just personal incentives of leaders. And how do they align or not align with building the right products for users or like taking risks is maybe the better way of saying it in the early days of Google, they took a lot of risks, right? Like all people, he went and built like a new product on the side and they let him launch it and like that was a pretty risky thing to do, but they didn't have as much to lose. There were fewer eyeballs on every single thing that they did. If they made a mistake, it was like, oops,

we made a mistake. Ha ha. Funny, funny. And then they like fix it these days, Google is a very different beast, right? It's, it's under tons of regulatory pressure. Like politicians are looking at everything that Google does. And the other effect that I observed is the people who progressed up the ranks at Google and became the like top level leaders. The nature of those people changed. And what I mean by that is in the early days, they were like pioneers and risk takers and they would go push and like do interesting new things because their personal incentive was to make Google very successful, right? So doing something that might have a 10% chance of success but could have a payoff of 100 X.

They would go do fast forward to today. The personal incentive of taking a risk that will have a 90% chance of failure is not worth it for most leaders at Google. And I think that is the key thing that changed over those years. So today, yeah, there's lots of cool, great things that Google could do. I mean, in fact, like right now we're having this AI moment, right where open AI is doing all these great things and launching them publicly to the world. And Google has all of the same technology internally. Like I'm sure, I don't know personally, but I'm sure that all these demos, it could exist very quickly inside of Google,

but Google can't launch them because if they do and it says something stupid, it's a big problem for Google and all this pr backlash and regulatory backlash will happen. Whereas when it happens with Open AI, the world is like, oh, well, yeah, it's early days ai they give him a

pass. It is a bit unfair.

That's the biggest problem. And, but this is like a perfect example of why startups can beat big companies is because big companies are encumbered by all of this crust around them.

Well, this is what I wanted to ask you, this is what I want to get to the heart of your nine years at sort of later stage, bureaucratic google people now know about starting a startup. There's lots of information online, but what we don't talk about is sort of how do you prevent your startup from declining and decaying under the weight of bureaucracy or, you know, lame managers or, you know, no product vision or whatever. What advice do you have? Yeah.

I wish I knew the silver bullet. I think the best way to think about it is as you get bigger and successful, you will have all these forces that are pushing you towards being conservative in terms of what you build and slow and big. All these forces are gonna push you there. If you want to not end up there, you need to very actively push the other way and it is hard and it's demoralizing work because you don't feel the success right away, right? But you need to ingrain that in the D N A in some way. And I would say that is the part that saddens me the most about Google is I don't feel like that D N A of we need to actively push hard to prevent our company from getting slow and bureaucratic. I don't feel like that's there in the places it needs to be anymore. But I think that's what you need to do as a startup. Like if you have a very successful startup, eventually, you will become those companies unless you very actively try to prevent it.

Yeah. Nobody wants to impact the stock price is the problem. I mean, fundamentally that's probably what that's about.

It's, it's, yeah, I think it's down, that's exactly its downside protection versus upside attacking, attacking, for upside. Right. Yeah.

You know, it's interesting, Paul Boo kite again who we interviewed and he was employee number 23. He always used to tell this story to YC startups about how, yeah, the incentives were just off at big companies. Like if you create something amazing that does super well, you get like a coupon for a massage and if you fail, you get

fired, that's the beautiful thing about startups, right? Startups. The answer is if we succeed, everyone succeeds here and we all share in the upside, right? Whereas once your company gets to a certain size and I don't know exactly when that happens, you can no longer have that same commitment to your team. You can't tell your team if we succeed, we're all going to get rich, especially once you reach the size that Google was when I joined, which was like most of Google's revenue was coming from search ads, of course, right? Still is today. And so like the thing that we were building,

there was no way I could make an argument that said like, yeah, the success of Google Photos in any near term is gonna actually impact the stock price and therefore like it's good for us. So on Google Photos, I mean, literally, if I had to tell you the number of human beings on a multi 100 person team who would personally have a chance of like getting rich by doing great work and really being successful on Google Photos. The answer is like two, maybe three people, right out of multiple hundreds of people. And so that makes it difficult to incentivize that team. Like how do you get that team to really want to work hard and build something amazing. And the approach that I took was just like the world needs this product. You need this product, your friends and family need this product. Let's go build it.

And we, we will be part of history if we can pull it off, right? And so that was enough to motivate that early team. But now that it's kind of successful, like what do you do? It's hard, it's a much harder problem.

I wonder if Google Photos will be like the last successful thing, Google launched not to get

too dark. Yeah, I hope not. I don't think so. Okay. For all the negativity that people project onto big companies and specifically Google, there are still like incredible people at Google and incredible teams doing really great work. They are just encumbered a bit more than they would be if Google was smaller and less successful. But those people are going to do great work. I think Google's challenges, keep those really great people there and not have them eventually get frustrated and leave.

That's a good segue because you have now left and have joined on as a visiting partner at Y Combinator, which we're thrilled about. Can you tell us a little bit about what led you to this decision?

Yeah, it was maybe a non standard set of circumstances that, that finally led me to leave Google for years. People would tell me like, hey, you should leave Google. When are you gonna do another startup? When are you gonna go join some other thing? And my honest answer to them was like, I don't feel like I'm done on Google Photos yet. Like I wanna, I got more stuff I want to do. Like, I really wanted to leave it when it was in a really good state as a business. Like after having my experience at that bump where I built something like really popular but did not have any business model that would work. Have it be like a longstanding thing. I really wanted that to be the case before I would leave.

And so we did a bunch of work in 2020 to, to set Google Photos up for success there and it worked like now it's, I can't tell you the details, but like it's very much working as a business and I can feel very confident that like it's going to succeed for a very long time. And then I got cancer. So in, in 2021 in March. Um, totally out of the blue randomly. I found out on a Thursday that like, hey, you need to go to the, er, or something wrong with your blood. So I go to the, er,

it turns out I had leukemia. I was in the hospital for 38 days starting. I did chemo for all of 2021. And so I e mailed my team on that Thursday. I was like, hey, guys, I'm supposed to go to the hospital. Like I don't know how long this is gonna be. Just take care of things, please. And then on Saturday, I found out it was leukemia and I found out it would be like a year long battle where I would not be able to work. And so I emailed him again on Saturdays like, hey, turns out it's gonna be a year.

Um God, see you see you next year and that was it. And I was going and so the team did a fantastic job without me. And so when I finally got healthy and came back, I came back and I was like, wow, they're doing great. Like they don't need me per se, right? Maybe I can add some value, but like, they don't need me to operate. And I think at that moment two things occurred to me. One was that, yeah, they don't actually need me like it's,

it's going okay. The business is working like the product is working everything is in a pretty good state. So if I was ever going to leave, I could and I would never have had that learning. Had I not been forced to leave? Right. I would never have realized that. And the second thing I realized is life is really short. And I think for my entire life, I never really internalized what that meant until I thought I was going to die on that Friday night or Thursday night, that first Thursday night in the yard, like I thought there was a 50% chance I would die. Um and that was like pretty real for me.

A 50% chance. Oh my God

that was, I mean, it wasn't, actually turns out there was no chance I was going to die that night. But in my brain, in my head given the information I had, I was like, okay crap if I fall asleep, like I might not wake up. And so I tried to not fall asleep that night. That was a solution didn't work. But when I got through that experience, right? It was a pretty grueling experience for everybody involved. I realized like, wow, you know,

I made it 40 years being perfectly healthy and now I've like almost died. And like best case scenario, I've got 50 60 more years left. Best case, right? Nobody lives meaningfully past 100. And so I thought like, wow, like I now have as much time left as I've ever had and like, it could end any time. So what do I want to spend my time doing? And the, the advice I would always give people who ask me, like, career advice was always like, kind of flippant but true,

which is find things that you're interested in and find ways to do that more each day. And if you're ever going the opposite of that, like you should check yourself and go back towards stuff that you really enjoy doing. And so when I first came back to Google, I would like block some time on my calendar in the morning to talk to startups, like startups, I was investing in or like YC alums or whatever. And then I would go do my job at Google. And I asked myself this question like, what did I enjoy most today? And the answer for so many days in a row was I like that block in the morning when I was able to talk to that founder or help that company or give them this product advice. And I finally decided like, Alright, you should really do what you tell people. And so the answer was like, all right,

I should leave. It's hard to leave. You're giving up a lot of money to leave and prestige and all these other things. But I decided like, well, if I die in 10 years, I don't want to have like, not done what I really want to do and what I love to do, which is like, work with startups. So it was very obvious I should do that. And then within a day of thinking through, like, the ways I could go do that, it was very obvious, like,

oh, I should go to, I see. Like that's, of course, the place that should go. So I

know we're so excited. Can I ask you, do you think that your sort of stubbornness and determination played a role in getting you through that your long battle with chemo and getting over the cancer?

Yeah, absolutely. And you know, when you ask people like their biggest strengths and their biggest weaknesses, like I would say, almost always, they're the same thing. And so for me, it is this like determination, stubbornness, whatever you wanna call it. Like if you ask my wife what she is annoyed about most about me, it's, it's that of course, but also it's in many cases like a superpower that I've got, I guess. And yeah,

it helped me with Google photos. Like I was able to just plow forward and say like, I'm not gonna take no for an answer. So we're just gonna keep doing this until I'm literally gone from this in some way. And with the cancer. Yeah, it was like, well, this is a difficult hand to be dealt, but I'm still way more fortunate than most people in the world. So I had better go beat this. If I don't like my God, I'm like passing up this incredible hand I was dealt in life even though this last round was not so great. And yeah, so I just put my head down and said like, I'm just gonna go do it.

And I think one of the learnings for anyone who deals with this, the job of a cancer patient is survive. That's all you have to really do. You're allowed to let go of all your other responsibilities in life. When you get dealt that hand, what's harder is all the other people in your life? Usually it's like your spouse or your partner or your close family members, they have to take on a bunch of that duty and do things that you know you were doing before. But also they have to be a cancer patient like partner, which is a full time job almost. So I would say it was way harder for my wife and we had a five month old kid at the time now. She's two. And yeah, it was hard. I would say,

well, we're so glad that you, you're better and you're in remission and I couldn't be happier and we're so happy to have you back at YC. You've just finished your first batch, right?

No, no, I know you're starting into my first batch. Just finished most of the interviews for the first batch. Okay.

It feels like you've been there for a longer David, you're going into your first batch that will be in January and this will air soon after. I hope, how does it feel to be back on the other side? Reviewing applications?

It's fantastic. I've learned, I tell people like in the Yes, I've been here three months now. In the three months I've been at Y C. I feel like I can honestly say I've learned more than the previous three years at Google. I just see so many things that I would have never seen before. I've learned so much about the world and I'm surrounded by all the rest of the people at YC and they're just fantastic people and it's just a clear different world than the world I was in before. So I'm very

excited about it. I remember you're actually in this magical place, timing wise where you've interviewed people, they've accepted their heading to Y Combinator, but they haven't started. You haven't seen the ones that are going to like blatantly fail and not try that hard yet. You're not like the solution with some of them are optimistic about all of them. You know what I'm talking about? See Levi. Yeah. Well, we're very excited. You think you have

another startup in you? It's a great question maybe. But I like there are certain people who maybe join YC as visiting partners and, and say like I just need a little break and then I want to do it again. Right. Or I want to go be successful for me, that chip on the shoulder, maybe as it does, it work. I don't feel like I have it like I think I kind of knock that chip off my shoulder with Google Photos, so I don't need to do it. And at least right now in my life, I don't know if I could responsibly say like I'm going to go raise money and be successful at a start up just because, you know, it takes a lot out of you as, as you both know, maybe one day if the right problem presents itself and,

and gets me hooked on it maybe, but I'm having a blast helping founders and it feels, you know, now having been a father, like I'm about to have a second kid, you definitely feel this, the idea of like, well, I don't have to be the person in the arena necessarily, but I can, like, help these other people who are the future of the world. I can help them in a way that people before me helped me. And that's a very satisfying feeling. And I like, I don't know if I really internalized it until I had kids myself. And you just feel so good, helping those people be successful

and you want to spend time with your kids, especially when they're

little. That COVID has been really great for that, to be honest, like for my entire daughter's life, like I'm around, which is really great

and, and dare I say startups are slightly incompatible with that. Yes. Yes. Sorry. Sorry. In such a dark mood today, you're such a cheerful, cheerful, optimistic guest. And I'm like negative

Caroline when you were talking about Google, I think the other thing that maybe worked well for us is the demographics, like the people that bump generally were like reasonably young and early in our careers. And so when we joined Google, we could like grow up there. And now, you know, we're all having kids. And the idea of going and working in a different modality at a startup is not maybe what you want to do right at that point in your life. So that's another force that gets people to stay on their path, whatever they've chosen.

Well, the YC community of founders is super lucky to have you and I encourage all of them to reach out and book office hours with you. You're about to get inundated. It's been so much fun catching up with you. I am so happy. We need to see your face again because I loved working with you way back when it seems like ages ago, ages ago. It was, it was very olden days of YC. So we're so happy to have you back and great to see you.

Yeah.

Thank you. It was great to hear the whole story. I'm glad I know. I'm glad I know it now. Can we ask about the resignation letter. Oh my God, the resignation letter. I couldn't believe that I'm like obsessed with the resignation letter. Unfortunately, that you told me about, do you remember, you told me that you wrote the internal resignation letter and you had to submit

it for my letter to the team. Yes, my I wrote an email to say that I was leaving and to send to the whole Google Photos team and yeah, like I needed to have it reviewed by various parties internally to make sure it was appropriate. And yeah, I think that if you look at like what, what the word changes were, 50% of the words were altered, right? Compared like in that same week, I wrote the like tweet storm or whatever tweet thread telling people that I was going to join YC. And at the same time, like I submitted my, you know, goodbye email to the Google bureaucracy and I submitted my hello statement to the Y C P R team And the difference was just so dramatic. It was like 50% of your words need to be changed here, the new sentences that are approved and the YC response was looks good. Let me know when you tweet and I'll retweet it. You know, it's so sad to different worlds, didn't

they make you take out like you ended? Like and I just as a parting thought, I encourage you to keep innovating, keep shipping and they're like take that out. It'll make people feel badly.

Yeah, it was, you know, it was, it was long and that was the deemed the lowest value piece of the email, I suppose. But yeah. Yes, I get it. Like when, when people would leave the photos team that I wasn't happy leaving like the people that I wish would stay, they would generally send a goodbye email and when they would say critical things, I would always ask them like, hey, can you just, can you send me your, your email before you send it to the whole team?

Because like, you know, I want you to be able to say goodbye, but also I want to control the message because that's, that's my team, right? I want to make it. So I get it. Of course, like we all do these things, I think for me, the big learning what I've always tried to do and try to do going forward is just always make sure that you're being authentic in what you say and do and don't ever let the position you're in or the role you've got or whatever change how you, how you present yourself. Because once you do that, then people get, they see it immediately.

They're like, that seems like corp speak. Well, I wonder what she really thinks, right? Or like, and once that happens, you lose the trust of the team. I think. So that's one thing I always tried to do and it probably was career limiting to me, Google in some ways because they couldn't, like if I were an S VP at Google, for example, I think there'd be probably lots of employees complaining about things that I would say or do, but that's just me, you know, take it or leave

it. Well, David, thank you for your time.

Yeah. It's an honor being on this. Wow. Yeah, by

David. Thanks. Well, that was fun. Huh? Karen. So cheerful. He's great. Actually, I really, really love the story about. You can't do this. I'm just going to do it. You can't do it. I'm just gonna do it. I'm doing it anyway. Like that is incredibly appealing to me as a person.

Just that personality. I'm just gonna do it. I know that he was so sure of what the right decision was and he just refused to listen to people who were trying to prevent it. It's so fascinating. Like that is the mindset of a startup founder. Yeah. And I kind of think to, you know, he was very clear that he's like, I didn't have a lot of downside. I didn't have a lot to lose. I think it would be the super power. People are the people who can also be like I have a lot to lose. But like this is who I am and this is the way I'm going to handle this situation. Consequences be damned. And I kind of like that.

Yeah, he was there for nine years. You have to agree with me that most of the startups that we know that get acquired by bigger companies. They don't last nine years. Oh, my God. No way. How long did PG last at Yahoo? One year to the day? And by the way, he will tell you this, he left a lot of money on the table because he was getting like new options or something every single month. And that was back in 1999, I guess. And the stock price was still doing okay, but one year to the day he quit.

Well, and that's kind of like even the show still Valli joked about like the rest invest and like, you know, all that stuff and yeah, so founders don't stay at these big companies. This is like, it's so the fact that he stayed for nine years. It's like a very unusual fact. I love his commitment. He wanted to just make sure that Google Photos was a huge success and was in good hands and was working properly. I love that. Yeah, I love it too. That's, that is amazing. And I'm so happy that he's in remission and,

and healthy again. Yeah, so scary. That was really scary to hear about. And I'm so glad he's at Y C. I love when, when people who went through the program come back, they have all these interesting, you know, then and now, observations which I think are really powerful and it's all good. Well, you've been through so much, by the time you've done a startup and then sold it and worked somewhere else, you have so much more Data in your head and it's that you can use to advise, you know,

young naive people like yourself like you 10 years ago or whatever. Yeah. And also just come into the job, having figured out this is what makes me happy. I'm so glad you're here because that's exactly the kind of people you want to work with and now I'm no longer in a dark mood. I'm so happy and optimistic. That's how I'm gonna look at the rest, rest of well and I think it's also happy hour for you right now so there's that it is it's a little after six. I'm going to go check in on the kids and this is really fun. See Levi so I'll see you next time. Yeah, it's usual. Alright see you next time. Okay bye bye.