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 Paul Bew Kite. Anyone who uses Gmail has Paul book to thank for it. Paul who by the way, is also known as P B not to be confused with PG, who is my husband and co founder, Paul Graham created Gmail in 2004 while he was employee number 23 at Google. Today, we're going to do a deep dive into the history of gmail, including the fact that it might never have launched if it weren't for a leak to the New York Times after Google PB went on to found a startup called friend feed, which was a social media aggregator. It was acquired by Facebook in 2009. After that, he joined Y Combinator as a partner and also became a prolific angel investor and now,

well, we'll find out what he's up to now as we catch up with him on the very first episode of the Social Radars. I am so excited because today we have someone on the show who is one of the smartest people I know in Silicon Valley and someone from whom I've personally learned a lot over the years. I first met him back in, I think it was 2005 when I interviewed him for my book founders at work, he had just created a new email app called Gmail. Of course, it's Paul but kite and then you and I were both lucky enough to work with him at Y Combinator. Um So we're psyched to be catching up with PB. So welcome, Caroline and I were sort of talking about your background and we're thinking it is, it's so sort of long and varied in, in tech that we wanted to kind of do this chronologically. We want you to take us back to like upstate New York. Isn't that where you

grew up in New York? So

you grew up outside of Rochester, upstate New York? Where did you start learning things from? Because you're like one of the most independent minded people. I know what signs were there that you were like this growing up.

You know, I just started learning things, I guess when I was a little kid, my father was an engineer. And he just loved building things and, and whatever. And so, you know, he worked at Xerox, which he didn't particularly like, but then he would come home and continue working on his own projects all the time. So he was always building something or whatever. He would give us always tools for Christmas have like a picture of me when I'm like four or five years old in my footie pajamas with like a bench vice. That was four years old when I got for Christmas was a bench vice. He

was a mechanical engineer,

electrical engineer, electrical engineer, but he was interested in all kinds of engineering. So he built in addition, you know, designed and built an addition on our house. He's like building things and he liked tools. He had sort of a compulsion for collecting tools and giving them to people for Christmas. So, you know, from an early age there would just always be lots of stuff around to like take apart. Like he would find, he would, he would find good things in like the garbage he liked, he liked bringing home like things that they were throwing out at work or there was a, there was an electronic surplus store that we would sometimes go to or like a Ham fest and we'd go get just like weird old equipment or something like that or, you know, I might just like, find something that he left on my workbench or some old computers that he had in the basement that I would like to take apart and smash or whatever. So, there was always interesting things to play with and explore,

to take part

or build. Yeah. So, from, you know, pretty much my whole life, we're always like, building things or, like taking things apart, putting them back together again, repairing them.

Were you a good student or was it one of those situations where your parents are always being told? Paul's very curious but he doesn't pay attention. He seems bored.

Like, were you one of those kids? I was an okay student. My limitation was that I a little bit Lazy and so I would tend to maybe not always do the work, but I could, you know, do pretty good on tests. So I think in my high school I just went to, you know, the public high school. I graduated like 40th in the class or something like that. So I wasn't like the top grades, but

I did okay. And then you went on to Case Western, which is a lot engineers go there. Right. Yeah.

Again, uh, you know, I wasn't necessarily like top students or whatever, but case had a thing back then where they would give out scholarships based on S A T scores. And so the first thing I ever got from them was actually just like a one page letter that said we will give you this much money if you go to school here. And my family growing up, we were always kind of like my parents were very frugal, like we never went on fancy vacations or fancy cars or any of that kind of thing. Like, they were very much not about spending money. And, you know, I learned growing up also to have like an aversion to debt or something like that. So the idea of spending like a whole lot of money to go to some kind of college, just sort of, I grew up with the idea that that was not a good idea.

And so, you know, with case I was able to get a scholarship that mostly covered tuition and it's like a pretty good school and it's relatively close. So that was, that was how I ended up there

and there were five kids in your family. Right. Yeah. Yeah. So there were five of us. So a lot of people to put through college.

Yeah. Exactly. Yeah. There's no way they were going to send me to some also. I probably wouldn't have been able to get accepted really top school or something. Where are you in the birth order was funny though, this one time when, you know, when, when you're applying to colleges, at least back then they send you these, like, mountains of junk mail and there's the, the envelope from Harvard came and my mother's like, oh, you're not going to Harvard, you know,

she was very anti just like, too elitist or something like that was like, don't worry, mom, I'm not going to

Harvard. They still send all that mail. That's still a thing. So you go to Case Western and then that leads you to Intel.

Right. Maybe the back up slightly when I was a teenager at some point, stuff was going on with computers. I was always interested in like, kind of like businesses and making money and stuff like that. So, you know, again, partially having sort of watched my father who was a very talented engineer but worked at this sort of dysfunctional big company. It was sort of like, you know, my father was Dilbert or something was kind of the sense of and, and, and so I kind of had this notion growing up that it would be better if you didn't have to work at some sort of terrible big company and also would do a little kind of money making ventures on the side. So I would like, I did door to door sales. There used to be this thing,

I'm sure it doesn't exist anymore, but I actually went back and bought some old copies of just like Boys Life magazine. It was like the Boy scouts magazine on the back side of it, there was always an advertisement for either the Olympic Sales Club or the American Sales Club. I think there are two of these things then you would sign up and basically they would send you like a catalog and then you would go, like, door to door or to your relatives, whatever it was, it was this way that kids could go do, um, sales and you would sell like wrapping paper or like greeting cards or like paper goods mainly, but usually price kind of like, you know, 4 to $6 price point. And then you would get to keep like a dollar for each item you sold. And so I would actually like,

ride around the neighborhood on my bicycle. And I'm like, I don't know, 10 or 11 years old or something like that. It was like, knock on people's doors and be like, hi, would you like to buy some stuff or whatever? Like, oh, are you raising money for school? And I'm like, no, I'm raising money for me. So I did that until unfortunately one time a guy, like opens the door and then he,

he has this, he wasn't even living there. He was house sitting there and all of a sudden this guy's got a pit bull and the thing jumps up and bites me in the face, partially involved by a pit bull. So I had to like, go get stitches. And what? And after that, my parents sort of thought that was not something I should do anymore. So it was the end of my door to door sales career. But, you know, it's good to know how to sell um, and we would do, we would sell things at him fast. I would buy,

you know, find good deals on some, you know, some, some sort of pricing inefficiency or something where I could buy something cheap and resell it.

What is Ham Fist? Is that a ham radio

thing? Amateur radio, for some reason? Ham, like, like amateur, I don't know, they're kind of like big electronics flea markets. At least they were back then. I don't know if they still exist. Kind of got ruined by the internet. But it would be great because you just find all sorts of weird old stuff or, or you could sell. So we would, it's like a little flea market for nerds, basically got

it. But you, it sounds like you're an entrepreneurial nerd.

Yeah. So, I mean, we would, we would, you know, go do sell things. My, my father liked selling things at the flea market. I mean, at the, you know, the ham ham fast or, or buying stuff and he was always, like I said, he always liked to find like a good deal, like,

if he could find something in the garbage and then repair it, that was like a big, he would find like old broken oscilloscope. So when he, when he died, um, unfortunately died uh last year and we're having to like, try to clear out the houses, just houses and houses full of stuff. But he had like 40 oscilloscopes or something like that. Like, he would, he loved, like these old, like Tektronix equipment. He would,

he would get oldest telescopes and then, and then debug them figure out what was wrong, repair, the electronics and then he'd have them, they're fixed and in theory he was gonna sell them or something, but he never did.

Did you find any treasures amongst all this stuff he collected over the years?

It's Kind of subjective. It's kind of weird stuff, right? Like, not everyone is interested in like 40 year old tectonic telescope or something like that. So, and then uh when I was a teenager, you know, I kind of got interesting computers. I bought my first computer. I got like a 3 86 D X 25 megahertz one megabyte of memory uh and taught myself how to program. My father said that the, the, the programmers, he was an electrical engineer. He didn't really know how to program, but he said that the programmers that work used to see.

So I was like, okay, I'll learn C and so I actually at a Ham Fist bought a Tyler, you know, we didn't have all the free software back then, but I got a copy of Turbo C for $11. Was that a

deal? Carolyn. And I don't know if that's a deal. Sounds like

a deal. $11 for a compiler? Okay. You know, software used to have to pay money for it. And then, yeah, I taught myself how to program and see and then actually ended up getting a little job programming in high school for this guy that my father knew how to machine repair business. And so actually redid the control software out of pick and place machine. So that was kind of cool. I was actually like in a factory debugging and like I built all the software for this, for this machine that would take metal bars out of a hopper and put them in a grinder and grind them. And

while in high school

you did this when I was like 16, I was doing

that was this like a minimum wage

job? I Got $8 an hour. It was more than minimum wage. I didn't always get paid on time. This guy was not always great at paying bills on time, but eventually get

paid. So then you went to college and did anything important happen there in terms of your interest in working building things are working,

you know, I was always interested in building. One of the, one of the nice things about case was actually that they were pretty early with the internet in terms of like having good internet connection and so forth. So, like, one of the things I was looking at when I was looking at colleges was like, I was interested in internet, you know, so this was like early nineties. And so I kind of knew that, that the stuff existed but this is before, like, the web had really taken off. And so, you know, like I remember I went to one college and I was like,

oh, do you have internet access here and there? Like, let me check, you know, that was like the state of things. And then she's like you went and asked someone, she said, oh, I think we have Ethernet. Is that the same as internet? Not, not exactly. So, you know, people didn't know the industry,

Ethernet and internet at the time. And then when I went to case I was like, oh, do you have internet there? Like, yes, every room on campus is wired with high speed fiber. I was like, cool. So they had actually, it was one of the, you know, sort of most forward looking things they had done is that they had actually in the early nineties completely did, like, every room on campus, every classroom,

every dorm room, every, in the fraternity houses, every, every single room had this, like, fiber jack on the wall kind of went with some weird technology because it turned out to not really be the technology that took off. We don't really use fiber today but they wired up the whole, the whole campus with, with, with fiber.

Were there other, like, like minded people like you there that were into this stuff?

Yeah. I mean, the people who were interested. So when I showed up, you know, it was like fall of 94 when I started, things were just kind of getting, taking off. So I also got interested in Linux uh when I was in high school. So again, at a Ham Fest, I bought a CD and this was like the very early days of Linux, it didn't work very well, like at all. So I installed Linux on my computer and was sort of like learning. I was interested learning eunuchs and that, that kind of stuff.

So, so when I got to campus, I started looking for people who, you know, would know something about Linux. So like the first, the first day I actually met someone in my dorm and he's like, I'm trying to get, you know, compile the new Linux kernel. I'm like, hello, you're my new friend. So he was showing me how to, yeah, because to figure out how to get Linux onto this,

like weird network because we had special, like, you had to have like a weird Ethernet adapter to get on the network wasn't standard equipment. So, yeah, there was that and then there was an ACM programming team. Uh And so then I showed up for that. So I was excited, I didn't really know anyone who could program before I besides myself. So I was excited to kind of beat other people who I could hopefully learn from. So I showed up to the programming competition and we actually did pretty good we had a good, good

programming team. And then what led you to Silicon Valley?

Well, so I was interested in startups. You know, I was, again, kind of like finding some way to not just be a cog and some giant machine and the idea that you could create something new and exciting. Um I had actually tried at one point in college to make my own, sort of like Web-based email service and this was actually before hotmail even came out summer of 96, I sort of accidentally ended up not having a job. I may be only applied for a couple thinking that they would hire me and then they didn't. So I was just hanging out in Cleveland in this basement underneath the sub shop and I was like, I'm just gonna make my own. I had this idea that I wanted, I wanted to be able to sort of like access email anywhere. I mean, at the time, you know,

it always lived on your computer. So people would be like, I need to go back to my dorm room to check my email or something. And like, I didn't have that problem because I could just like telnet into my computer. But for all the sort of like those people or whatever email was this thing that lived on your computer. And so I had gotten very excited about like Java and the possibility of, of like mobile code code that would be downloaded from the internet. And Java, you know, is very exciting as history turns out it never delivered on that promise. But Java script of course did deliver exactly that, which is that the browser downloads the code from the server and then it executes locally. And that way you can actually build a really great experience that doesn't require constant round trips to the server. But kind of like I ran into my problem of somewhat limited attention span. And so I, I got bored with that project and started watching lots of Dukes of Hazzard and going for bike rides and stuff like that.

You know, you could have been the first sort of email.

That's

fine. We'll wait. Did you have an A O L address at the time? Like, or

do you have like a, I had a university address? Okay. Okay. Never used A O L. Okay. So, yeah, I was interested in startups and then, you know, when I graduated college, there was no white commentary, there's no startup. Anything like you look on the internet. I mean, there was no Google is the internet was still very young. And so it wasn't like I could just go find like a listing of startups.

Like it didn't seem to be anywhere to begin even, you know, but it did seem like they were generally located in California. So it just sort of geographically, you know, Silicon Valley, like I could like, locate on a map and so my strategy was like, okay, I'll just sort of moved to Silicon Valley and then presumably it just like bumped into a startup or something like that.

Yeah,

it's gonna be an Intel. I had a friend who had, was a year ahead who had taken a job at Intel and they had this, like, rotation program that sounded kind of cool. It's basically just sort of a series, almost like a series of three internships in a row. But you kind of get to try out different jobs within the company. That sounded kind of fun. So I took, I took that job with Intel and actually just coincidentally my second rotation there was in the mobile marketing division or group or whatever. And one of my coworkers in that group was Susan Luchinsky. No. Well, Google was in her garage. She was working in Intel in the same group as, as, as

I was. No way. Is that how you? No,

we didn't, we didn't realize that until like, later on. Um, I mean, I didn't know her super well. It wasn't like we chatted a lot or something. I was there for about a year and Intel was, I just found it, you know, it wasn't bad but it was just sort of like draining. Like I would find myself I'd be at work and I'm just like, oh, I'm so tired, you know, I think I'll go home and take a nap. And then I go home. I'm like, you know, I'm not really tired anymore.

So, you watch Dukes? Dukes of Hazzard?

Yeah. I, I just found it to be a uninspiring and kind of draining environment. It's just very gray and just, like, slow and it just wasn't fun. It's just, it's just, there's just nothing fun about it. Um, and again I was still really interested in Linux and back then, you know, big companies were still very suspicious of Linux. It was like this cancer or something like they didn't like Linux. So the two things I was interested in was like startups and Linux. And so I basically, my,

I was like, okay, I'm just gonna, you know, apply for some, try to find a startup and, and I just sort of, I can't say that I did like a really in depth research. I just sort of made a list of what I could find, which was only like 10 companies.

Where'd you even find them? Yeah. Where were you living?

And how did you find them while I lived in Sunnyvale and working at Intel? I would always read slash dot so slash dot was, yes, that was really the site. Um And so slash that would cover all the time because it was like a, you know, fans site practically. But Google would show up on, on slash shop periodically because Google was built on this like Linux cluster, which was like, what could be more exciting than like this cluster of Linux machines and they had this like Linux specific search. So I would see Google show up on slash dot As well as you know, there were a handful of other basically, like Linux companies would show up on on slash dot So that was how I would know about them. I forget it was like six or 10 companies, something like that. Not like a huge number.

So I just like, emailed my resume to them. And ironically like when I first emailed Google, my resume had bounced. Their, their mail server was mis configured. We weren't able to receive any mail. It was sort of a temporary thing. I had to resend it the next day. But it was kind of funny for the first time I, I applied to Google, the email bounced. Yeah. And so then I never heard back from most of the companies, but I interviewed at Google and they asked actually really smart questions which I think like one advice for I sometimes give to people talking to interviewing startups. However,

is actually what is the quality of what they're asking you? Right, because that's how they're finding people. So I did interview at this one other startup that was doing little stuff like their questions were just dumb there. It was kind of like trivia, you know, what are the layers of the OS I stack or something like that at Google? They're actually asking some pretty intelligent questions. Like I remember was asked this, like, sort of hypothetical, okay. You know, you have a server that's running slow. How do you figure out why or whatever? Right.

And, and kind of like talking through like the process of debugging, like, okay, you know, is this, like, are you limited on CPU, what's going on is an I O problem, you know, tracking down, like, where is the bottleneck and like thinking through system level problems? Uh I mean, I think he's still sort of like one of the main vice president of engineering, but he was like the original VP of engineering and he ran engineering for a very

long time Because this is now back in what, 1990, what,

This is 99,

1999 and was it just oars in the interviewer did Larry

and Sergei? And so, I mean, at the time, basically interviewed with most of the company, I mean, there weren't very many people. So yeah, a series of different engineers, but this was just, this was, this was before the series a even and there was only, I mean, it's really only like maybe seven or eight engineers or something. It wasn't a very big team. So, yeah,

I interviewed with all of them. Yeah, Google is the only offer I got. So, you know, that made it easier. So I didn't really have

any of the companies that rejected you still in business.

Uh I mean, I wasn't rejected. They just never replied, do they exist anymore? I think one of them was probably like Red Hat or whatever Red Hat there around in some form. None of them are terribly successful probably has the most successful. I don't, the other ones there was like V A Linux. I don't know what happened to them. I think they died. You

Interviewed at one company? And it was Google? Yeah, I mean, honestly, oh, I mean, I'm glad no one else contacted you back. I'm glad that uh

you don't have a lot of hard

decisions. You were like number 22 employee number 22 or am I wrong? 23? Okay. So very, very early on. What was it like early on you? I mean, you obviously joined what, a couple weeks after the interview?

Yeah, I ended up joining um for some reason it ended up being maybe closer to a month after the interviewer's not quite talent anyway. Yeah. So in the intervening time, actually, it's kind of interesting. So I, I interviewed and then they kind of called me back in to make the offer. And then I think that was when Larry and Sergei like presented the offer and then they're like, oh, and also like watched the news or whatever because it was like, I think the next day was maybe the series a announcement or something like that. So I got my offer, right. Basically, I think it was like the day before the series a announcement and then I also had to try to figure out what it even meant because, like,

the offer, you know, I never, I didn't really know about stock options and stuff and of course, being kind of like, you know how it's just like the people on hacker news are, you're like paranoid, somehow I'm gonna get screwed on this or whatever. Right. Where I'm like, what does this mean? Why, why are they priced so low? You know, because, like,

the shares were my original Google shares. I think, like, if you account for all of the stock splits that have happened between now and then I, I paid, like, two cents a share for my, for my. Oh,

wow. And I think you would have paid less if the series a had been later, like, if you've been hired earlier because the series a probably impacted

that. Yeah. I mean, if I had gotten hired, you know, a couple of months earlier I'd be much, much better off obviously. But, I mean, it does impact you, you know, because you only get a little, you know, it's just a little fraction of a percent of the company, right. Like, but it turns out a small fraction of a percent of Google is actually still pretty good.

Yeah. Yeah. One of the not obvious things about startups is it's much better to have a small slice of a big company, the big slice of a small company and it's counterintuitive. But the reason is you can only have as much as 100% of a company. So, you know, the orders of magnitude there are sort of limited but the number of zeros and the valuation can go pretty high. Um So it's actually easier to make money, I think. Like, you know, when you have a really hugely successful company, it makes a lot of people pretty wealthy versus a small success that makes maybe one or two people.

Yeah, which we've seen obviously Y Combinator, we've seen that. So you're at Google, what are you working on when you first join? Initially?

Actually, they gave me 22 projects. The one was to build an ad system because they didn't have any ads. And then the second was shopping search because like, they also thought that would be sort of a cool thing. Well, one of the things that was kind of funny about Johnny Google was like, there was just the level of sort of ambition, there was really sort of intoxicating, right? Because like Larry was just sort of crazy, like he was just like, we're going to do this. So we did this. So we do this, you know, it was,

it was like, you know, here we are just this little tiny company and it's like, okay, we have a new employee, let's give you two projects. And then actually, I was working on that with Marisa. Marisa had started, I think the week before me, Marissa Mayer. Marissa Mayer. Yeah. Okay. And so we kind of shared a corner of the office there and, you know,

started working on these projects. I ended up The ads thing ended up being kind of a lot of debate about what the ads products should even be. So, a lot of people don't really know anymore, but it took like four iterations before Google actually had a successful ads project. Like the very first ad product that came out was this thing that would recommend books on Amazon and then collect the affiliate revenue. And we made like $20 or something like that. It was both like it was, it was, it was both like problematic in that. It would make offensive suggestions like when we search for something and then, you know, come up with a book recommendation that you would look at and be like, oh no, that's not really cool. On top of that,

it never really made any money because like most of the time people don't really want book recommendations, they search for something on Google. But anyway, I ended up focusing more on the product search. And so I built out like a product search. I mean, all of this was happening over the course of a few months because it's a startup. So everything goes quickly. But the I ended up building this product search for a while. It never was like quite good enough that we launched it though. So that never launched though, along the way, while I was working on that. One of the things I ran into is just the fact that I'm not very good at spelling. And then looking at our query logs, I discovered that that's also true of most of our users.

And so I, I added the, did you mean feature? I put in the original, did you mean feature? Because I'm like, this is, this is such an easy way because they were trying to figure out how to improve quality. Like the easiest way to improve quality is just to spell your words correctly. Oh my God, like me and half the other humans can't spell very well. So it's a really easy way to boost, boost the

quality you created. Did you mean I'm in shock because I was gonna ask you you like created like such distinctive things within Google like adwords, gmail and the whole don't be evil thing. But you also did, don't, did you mean?

Yeah, well, I I didn't create adwords and adwords was, you know, I made the first version of adsense. It's a sort of subtle distinction. Adsense was the contextual targeting and that sort of like, yeah, that was kind of like a side project of gmail because initially I built it for gmail and then people are like, hey, this would work on the rest of the web to. Yeah, they did. You mean I did again? I, I would, I'm pretty good at making a lot of times,

like a really quick and dirty version of something. And so it was actually, while I was building the product search, I was, I was just like, this is kind of dumb that it doesn't have a spell corrector. So I just threw that in and then, you know, actually pushing it out to the main web search took a little bit longer because, you know, you need to make it. I had just done some sort of quick hack with like a spell or something like that. So then we had to kind of license something. The initial did you mean was not really that great? And so I was working on making a smarter, did you mean because it was just kind of a dumb spell corrector that we had licensed from someone?

And then I did some code to try to make it less dumb because like, for example, it would want to correct words like turbotax, it would say, did you mean Turbo ax? Like a stupid spell character would do back then? So at the time I was working on the spell, this was maybe a year later when I was working on a better spell corrector. I decided to use it kind of as an interview question. So when I was interviewing people, I'm like, well, how would you build a good spell corrector and kind of like, talk them through it. And most engineers, most people are just terrible.

They have no idea. Some people, I would say like, two thirds of people are, are just like bad. One third of people are kind of like, okay. But then there was like this one guy who gave just this amazing answer where he was like, he was already went like past what I was thinking, like in the interview, he already was like, his thinking was already ahead of me. And so I was like, wow, that's great. Okay.

So we hired him, this guy Gnome Shazier and he, he started, it was actually a few days before Christmas or whatever. And so I set him up like, okay, here's where I am, you know, in the code, see what you can do. And I went away to visit family for a couple of weeks and when I came back two weeks later, he had built like the thing that we know. Now the did you mean feature, which is like the world's greatest spell corrector that had ever existed was first to on the job.

Oh my gosh, that's amazing. Then when did you start getting involved with Gmail? Wasn't it a side project for

you There? No, not exactly. A lot of times people think it was a side project but it was, it was actually sort of like an assigned project. I did have a lot of side projects. But that, that wasn't one of them, summer of 2001 inside of Google, that there was kind of this reorg thing where Larry got frustrated because he thought people weren't moving fast enough. So his solution was to get rid of all of the engineering managers. They have sort of hired a number of managers and it was organized into like these groups and each group would kind of have its own thing, but they weren't working on whatever he thought was important. So his idea was we should just like not have managers, engineers should just like have projects. So instead of having groups with managers that would be projects with engineers. And so all of the engineers were given a project or,

you know, there'd be a couple of engineers on a project. And so I met with, you know, when they were kind of meeting with this person, I sat down with Larry and then Wayne Rosen, who is the VP of engineering at that point. And they're like, we want you to build some sort of email product. So that was kind of the spec was some kind of email thing,

some kind of email thing. Okay. Yeah.

So initially I was still kind of wrapping up another project. So it was to some extent, part time to begin with because I was finishing up the original Google Groups. So we had bought, I don't know if you know, using that, you know what that is. Right. The old internet message board. Yes. Yes. And it's an archive that goes all the way back to the 70s. It's the oldest reddit, essentially.

And Google

had bought that. Well, we had bought, it's an open thing. So, but what we had bought was the site called Deja News that had the largest using that archive. But they were, it was a startup that was, was dying and had run out of money and their systems were kind of shutting down. And so we got like a good deal on it and then we would be able to own their archive. But we didn't want to try to maintain their code because it was some completely different code base written. And I think Tickle, I want to say like a weird language and we had a deadline because their whole, their data center was shutting down or something like that. So we only had like one month from the time that we acquired the company until their servers were gonna shut down. So we had, it was this really great project because we had a really hard deadline,

which was that we had to launch in a month. There's no wiggle room on that. So, so a group of us very quickly built this Google Groups, the original Google Groups project to index and serve this use nut content. And so that I was finishing up on that when I started Gmail And so the very first version of gmail that I built was built based off of just using that code that I had been working on previously. So I mentioned earlier, you know, the first time I tried to build an email project, I ran into this, this problem where I was writing a bunch of code for a while and then I got bored and kind of like distracted. And so one of the things I kind of had learned over the years is that I just my own psychology, I have to always be keeping myself sort of engaged in the product. And so for me, what I really like is to always be launching things. And so with gmail,

I was able to build the first version in a day and then launch it. And so what I did was I just took this using that indexing code that I had from the previous project. And then I took my email, my mailbox and I and I just wrote a script to convert the email to look like using that data. And then I just shoved my email into this into this, using that search. And then I just like launched it. I just send it out to engineering to be like, hey guys, I built like this email search, you know, let me know what you think. And so, you know, that's like the first version of the day, day zero at Gmail when I launched this product.

What, what do people say? People say, well, it's kind of useful but it would be better if I had my email instead of yours. And so that's like a feature request. And so it was all just internet. So I first version in one day and then, you know, I got feature request which is like people wanted to search their own email, not just my email. So then I'm like, okay, That's like now I know what to do. And so and so like I went to work and I made this thing that would kind of like all through the home directories and suck up people's email and index it and then partition it so that It would just get like one person at a time. And then,

you know, I had like that was like version two. So I launched it again. Okay. Now I have email search with your email and so then people would be like, Okay, this is cool. And now I want to reply to an email. I'm like, Okay. So then I went in and added a reply for feature and just, you know, iterative lee would launch a new version every day or two. And then just constantly people would complain about now they want to send email or whatever, you know, they want an address book,

you know, and just kept adding feature by feature or, you know, it's too slow or, you know, whatever the problem is and try to keep making the product better and better. And we continued through this process and there are a lot of complicated ups and downs in there as well. But ultimately, we came up with this goal for that would be ready to launch to the world once we had 100 happy users. And so, and this is something, you know, we still kind of use sometimes in advising startups because it's actually a pretty good way of working on a product because it's easy to get people to sort of like tolerate a product. But, but you want them to actually some of them to actually like it, but you don't need all of them to like it.

And so I would do, I actually embedded just like a little one question survey inside of Gmail, which is like a little box will pop up and say, are you happy with Gmail? Yes or no. And it's just like, yes or no. And I would get a list of names then and I could go through the list of knows I would just go talk

to them because they're all part of Google's engineering,

you know, just inside it would be like down the hall. So I would just go down the hall and be like, okay says you're not happy with Gmail. What's it gonna take to make you happy? And so just, you know, it's basically door to door sales. Like it's like, what's it, what's it gonna take to get to get you to be a happy user. And for some people they'd be like, well, basically needs to be exactly like outlook and I'm like, well, that's never gonna happen. So,

you know, across this person off the list but other people, you know, it's something much more attainable, like they just needed one feature. There's like something they didn't like or Whatever. So, so basically there's some people who are easy to make happy and some people who are difficult and so you just focus on the ones that are easy. Uh and then eventually we made it 200 and then sometimes, you know, eventually I would get the outlook people too because back then outlook had this bug where once your mailbox on disk would reach, I think two gigabytes, it would corrupt the data and lose everything. Oh, no. So then I had the only copy of their email.

Once, once Outlook would, would crash and storing their copy, I would have the remaining copies and then they would start using Gmail. When,

when did you decide to start calling in gmail? Was that immediate or

you know, the idea was around, yeah, very early on. But at the time we actually they were into code names because we were trying to keep things secret. Like they didn't want Yahoo to find out which was inconvenient because sometimes like, yeah, who would be there like one time at dinner. I was sitting there with like Larry and Sergei. I think we're there. And then Dave Filo from Yahoo was sitting there, you know, with Larry. And so I'm kind of sitting there at dinner and people kept coming up and asking me questions, you know about. So we had a code name, the code name was Caribou.

But people keep asking me basic product questions. And finally I realized I need to just like get up and leave or whatever because I, you know, I can't answer everyone's questions while I'm sitting next to like the founder of Yahoo. So yeah, it was called Caribou internally. Actually getting the domain was, was, was difficult. We, we just barely managed to get it. I don't know. I think maybe we just procrastinated. We, we ended up actually not quite getting. There is a second domain with a different spelling that we didn't manage to get in time. Maybe they have it by now. I haven't checked G M A L E. It was a porn site.

Good gracious. Can I just as an aside, say listening to you tell this story and saying that you were the kind of person who would keep going. You always wanted to be launching and you would talk to users. You're like the dream founder. I have to say like if I were fun, I wish I could have funded you.

That feedback loop is what makes it fun. So if I work on a project just by myself without that loop. I sort of like lose motivation. And so it's also part of the problem that have fast forward. Like By the time I left Google in like 2006, the release cycles on gmail were like, you could check something in, but it's gonna be like months by the time, you know, it makes it all the way out to the world or whatever. And I just like fast iterations, you know. So when we had friend feed later on, I would like you to write the code, I would push it live and then if it's good, I would check it in. I,

I just like, I just like, you know, immediate feedback loops where you put something out there and then people love it or they hate it or whatever and you learn and you go forward this like ponderously slow movement where, you know, you do something and then you don't see the, the effects for, for many months to me is just the motivational.

Can you talk at all about? Didn't, wasn't it true that Gmail almost didn't see the light of day. It almost did not get launched within Google? Yeah,

I mean, so there was definitely, there were definitely different opinions. There were a lot of people who thought the project should be scrapped. So, so they're basically like a couple of, of objections. One objection was that it was like, too weird. Because it was quite a bit different. Like this one particular VP, he was like, you know, I really love a O L mail. You should just clone A O L. It's like, I don't know how to respond to that.

One segment of people said this thing is really weird and no one's ever going to get it because we, we did do, I mean some kind of unusual things that conversation view is very innovative. It has key bindings that I borrowed from V I, which is a very unusual thing to do to put a, an obscure UNIX text editor, borrow ideas to put them in a web page. And the way that it behaved as an application was, was unusual at the time as well because it was kind of the first of that thing, you know, so, so even doing the whole thing in javascript is very controversial when I first wanted to do, I started doing a lot of things in javascript. People are like, you can't do this if you write this in javascript, you know,

Microsoft is just going to change the browser to like break it, you know, because they were all very afraid of Microsoft at the time. But a lot of the executives like Eric Schmidt, you know, had come from sun and so like Eric had spent his career getting crushed by Microsoft. So he was like very paranoid about that. But I was like, no, I really don't think they can, you know, just like break javascript and if they do make some small change, like we can just change the code on our end to work around it. And the thing that's actually really funny historically is it turns out not only did they not change the browser to break Gmail, they actually did an emergency push to IE six at one point or like high priority patch to make Gmail work better because Gmail was like trashing the breaking the garbage collector in IE six. So Microsoft actually made an in improvement to IE six to better accommodate Gmail,

the javascript thing. Yeah, people were opposed to that because it was really kind of like bleeding edge at the time, the browsers didn't quite work. And one of the things I was afraid of that might keep us from launching is I had trouble crashing the browser a lot. So I had to learn a lot of tricks to not crash the browser because it was really easy to push the browsers too far. It was IE six and then like Firefox one point or something like that. And they could just barely handle what we were doing. And I'd have to be careful because if you push too far, like it would just trigger some bug and the whole thing would die.

Oh Wow. I never knew that.

So yeah, there was the technical side of it. So at one point there was a push to actually just go back to being totally html, that kind of distracted us for a while and then by the time of launch one object is that it's too weird. The other objection was that it's not weird enough. It's too conventional. Like we're Google. People expect something really revolutionary.

Wow. Was gmail, not revolutionary? I mean, I think it

was, depends on your opinion. Some people thought it should just be like more different. Other people thought it should be more normal. Some people thought the gig was too much like why are we doing a gigabyte? Why don't we just do 100 megabytes? That's still more than anyone else. I was like, no, you know, cause Yahoo is offering four megabytes and Hotmail was offering two megabytes. I was like, it's so much better if we come up with 1000 right? Real. And then the other problem we were running into is that actually like, you know, the engineering was like a little bit bumpy still not everything worked really well.

So we were building on top of web search infrastructure that had been just had different constraints like, you know, if it would encounter an error, it would just throw away the data because it would be like, well, we'll just get it on the next crawl. So actually modifying all of our infrastructure to not lose data. It was really hard. We had weird performance problems. The code was like, you know, pretty like shaky at the time we launched and I was very afraid of losing data. And so one of the strategies I took was that we would just keep multiple copies in different locations and different formats and stuff. But consequently, it was like every email ended up getting stored like 13 times or something like that in different, in different systems.

And, and the reason for that was that way when there was a bug in one part of the system, I could like replay it from a different part of the system to fix it. So we had this, the way that the data was stored was this like log structured file system that we built. And the cool thing about that was that you could basically replay, you could fix bugs and then replay history to undo just sort of like retroactively fixed bugs in the system and, and some cool things like that to try to try to make it more responsive. But then, yeah, it almost didn't launch. And actually the thing that it might not have made it out the door except someone inside of Google actually leaked to the New York Times that we were launching this email product on April 1st. The thing was that it wasn't quite ready, but there was then this impending story. And so we actually rushed it out early to try to beat the New York Times story. So if you go back and you look at the press release,

it launched April 1st at midnight U T C. So it actually launched, actually launched the night before. It wasn't even April 1st in the United States yet. We, we sort of pushed it to UTC so that we could, we could get a jump on the New York Times. The only problem was that we hadn't actually finished writing the code yet. Oh my God. We actually launched email before it was written. So I didn't get a lot of sleep the first

couple of days. And did you like finish in the next, the next

day? It worked really quickly. So when we, when we put out the press release, it was such a rushed thing, the D M S didn't even resolve. So if you tried to go to gmail dot com, there was nothing there. We launched a landing page. You know, the thing is you're not embarrassed when you launch, you know, we waited too long. So we definitely didn't wait too long.

And what happened when you launch? Then the New York Times article goes out and do people immediately embrace

it or? No? No. Well, so part of the problem was we didn't really have capacity either. So there was this chicken and egg problem where I couldn't get hardware because the project wasn't really ready to launch and the product wasn't really ready to launch because we didn't really have hardware. So the only machines we had where I think it was like 300 of these old, I want to say like Pentium threes or something like that, that no one else in the company wanted. They had less than a gig of memory even. I think, I think like 256 maybe there were like these all low memory machines and, and we had coupled with sort of the inefficiency of the system, we had enough capacity for 10,000 users when we launched, which was like enough for like Google employees and their friends basically, which is also part of the reason we had the invite system. So the invite system was also one of these things where they said,

well, you can't launch until you're ready for everyone to show up. I'm like, well, that will never happen because it's so hard to scale something like this. So I I was like, let's do this invite system, you know, well, that way we can limit the rate of growth. And Larry was like, well, no, that's like planning for failure. I was like, okay.

Well, in that case, it's a growth hack, you know, this is this will make it viral somehow saying that it was like to limit our growth. It was like, it was like a no go. But if I re pitched it as being like making it viral, then then it was like an acceptable strategy. The real reason for the for the Gmail invite thing was simply that the entire system would have collapsed. Otherwise we just didn't have capacity. But yeah, Gmail didn't even exist when we launched it, you know, to sort of like make the situation more difficult. My brother had just died March 9th.

So yeah, so like, you know, the last night I was there with him. Actually, he was, you know, only half alive at that point, kind of struggling to breathe. And I was like on my laptop doing um doing some account integration code, like trying to finish up some stuff. So, you know, when he died, I took off for a couple of weeks, you know,

we had a funeral here and a funeral back in New York. And so I was completely away from everything for a couple of weeks. So when I got back, things were not all going, you know, exactly according to what would have been ideal schedule. So there was, it was a little bit of a ship show back on the team. So we really weren't quite ready to launch. And like I said, like, actually the code wasn't quite all written yet. So, so after we launched there on April 1st, I had to like work to, it was actually the remaining code was the part that,

that integrates like account creation and everything. When we launched, there were zero Gmail accounts in existence. So I created the first Gmail account after I should try to go find the timestamp it was sometime later that day. So I created the very first email account like okay, that works, you know, push the code

or checking the

Hello World Gmail is actually so that yeah. And so then okay that worked. And so then I sent an invite to myself and then my personal email account is like the second ever Gmail account and then like that worked. So then I I invited like the rest of the team and the rest of the company. So it was only later that day that people inside of Google even had Gmail accounts

on the day that

it launched had already launched and no one including myself had an account.

Wow. Oh my gosh. That's pretty crazy. I don't think I knew the extent of the craziness and I certainly, I don't think I realized that it was so soon after your brother passed away.

Yeah, I mean, it was a pretty, it was a pretty out of control launch. They actually, after we launched, they implemented a whole bunch of new policies to make sure that a product like Gmail never launches again. I think

I figured out who leaked it? Like, that's

pretty weird. Or was it not weird? It was, it was someone in a different part of the company? So I don't, it wasn't someone I know

how did like Larry and Sergei respond like, let's just say a week later, were they like great job Paul or were they,

well, so initially we had this problem, we launched this thing but, but no one had access to it. Right. So eventually we got around once, you know, day two or three, we finally invite reporters, people get to try out the product. But initially, some people weren't even sure if it was a real thing because we launched on April 1st with sort of implausibly good specs. So like if you go look at slash stop people, like come on people, this is an obvious joke. You can't, we can't fall for this.

There's no way they're really giving away 1000 gigabytes for free. Oh my God. You know, because if you remember back then the like people working, you know, inside of a corporation or something who had like an outlook account would usually have maybe a 30 megabyte quota or something like that. And so actually, interestingly enough, one of the groups were gmail really took off early on was reporters, reporters all loved Gmail because their official email address that like, you know, the New York Times would give them or whatever only allowed them to save like 30 megabytes of email, which, you know, if you're a reporter, you really want more than that.

And so they loved the fact that they could just keep everything. I mean, that they didn't have to deal with these ridiculous quotas and, you know, for years and years, like email administrators had gotten really good at making excuses for why it's not possible to give people, you know, more than that. Oh, you don't understand. Email is really hard, you know, you can't just like give people hundreds of megabytes of storage. And then of course that excuse falls apart when we like do it for free. Yeah.

Oh my word. I had no idea about some of these details. Remind me PB I met you when I asked you to be in founders at work, which you did and I think you were just leaving Google around

that time. Yeah, it was around that time though. Yeah, because I was interested, you know, I had reached out to PG because I was interested in, in Y Combinator. So again, you know, on slash dot where I get all my news, um I had seen the original announcement for the summer founders program and I thought that seemed like super cool. Like I just, I just thought that was like the best idea ever because it sort of spoke to my own experience, which is that, you know, I was interested in startups and,

you know, I didn't go to like Harvard Stanford or whatever where it's like, oh yeah, roommate started Cisco or something, right? Like I feel like if you go to one of these environments where everyone is doing, it is like no big deal. But my only strategy for like finding startups where it was like physically moved to California. I didn't know, or no startup founders who came from my school or whatever. And so I thought the idea of just like having this open program where anyone could apply and, and then you would just like, teach them everything that they need to know and connect them and, and like, anyone could start a sort of not just someone who's like, already super connected to me, that was, I thought like, just such a great idea and something that is really powerful because you're opening up beyond just like the chosen elite

or whatever you were our target mark. When we first launched, it was like smart programmers who might not have any clue about the business side of startups, but they want to build something and they can now build something because all they really need is a computer come study with us basically for the summer. So I remember we invited you to speak for that first summer.

Yeah. Well, it's actually not, not for the first summer. So I contacted um I think it was in the, in the fall. Um that summer, there was still a lot of stuff going on. But I in the fall of 2005, what happened actually was that you announced the that you're gonna do the second batch in mountain view. And so that's like close by. And so I reached out and just introduced myself and like, hey, you know, I love what you're doing, you know, let me know if I can help out or whatever. And so that was how I ended up talking to, to you that PG introduced

me to you. Okay. And we must have invited you to speak at the

Yeah. So then I still got something back with, with, okay. And all of them.

Oh, my gosh. That seems like so long ago with the paint drying on the walls of the building. So you leave. Why did you leave Google? What was your plan?

So, I mean, I don't exactly have a plan but I, I, you know what, what really happened was that, you know, our first child was born in 2005. It's severely premature. She was 100 days early and, you know, almost didn't survive, had lots of surgeries and so forth, which is why, you know, the whole summer of 2005, I was actually in the hospital again.

We spent the summer of 2005 and UCSF neonatal intensive care unit. So I, I taken seven months leave from Google. And when I went back to Google in the fall, I was actually like, really excited because I always loved like, working and like launching things and just like, I like the excitement of movement and getting things done. And I got there and, you know, I was like, so excited I was having trouble sleeping the night before and I got there and it was that thing where like the life just drained out of me. It was like, I was back at Intel, my computer had stopped working and I tried to get a new one and then I ran into sort of some sort of I T bureaucracy where they gave me a new computer but actually it was broken and I spent debugging it and then when I finally figured out that they had, like,

mis configured the D M A or something, they're like, oh, yeah, we knew about that. You just have to fix it. I'm like, why are you giving engineers computers that, you know, are broken? They, well, we don't have time to fix it or whatever. I just immediately got like this feeling like I'm stuck back at Intel in some big company.

What happened in those seven months? Like, that's the seventh

personally, it was just sort of like the, you know, frog boiling water kind of thing, you know, you become sort of more aware of it, but also, you know, the company was growing so I'd end up in some meeting people. I don't know, I don't know. I kinda had this realization which may or may not be accurate, but I kind of felt like, okay, I can either if I stay here, I need to become like an effective big company person because a lot of what needed to be done was a little bit more kind of politicking. Like The last thing I did was managed to get like more hardware for gmail.

We were always running out of hardware because we were growing, we're resource constrained. So we, but we were running the system at close to 100% capacity, which is a terrible thing to do. And it was like grinding the engineers because they were constantly scrambling to like keep the system from, from dying because we were so close to the limit. And so I was always trying to get, like, the last thing I was doing was just constantly trying to get more hardware. And so finally, like, my tactic was like I announced, we're gonna shut down new sign ups or whatever and, and like sort of just sort of an internal bluffing thing or whatever to try to sort of embarrass them. And then finally,

like, we got approved for $100 million in new hardware or something, which admittedly is a lot, you know, the product could have been actually a lot more successful, but we were hardware starved for, for years. But anyway, I kind of had this realization. I could either become like a really effective big company person or I could just leave. So I chose the latter. And

then when did friend feed come about like a couple of years later?

Yeah. So I, I ended up just kind of taking off some time and, you know, we still had this baby take care of and everything. But yeah, I was talking to my friend Sanjeev, who is, who is like the second person on, on Gmail and we get together and he was, he was kind of interested in starting something. So, so we decided to start something. But we also my biggest thing is always like, you just got to find really great people. And so we were keeping an eye on other people who we thought were really great, who we thought might be interested in leaving Google to sort of join the two.

So we didn't have a specific product in mind. We actually had more of like a culture in mind. We wanted to make a really great engineering company where it was just really fun to work. Like, basically, I was just trying to make a job for myself. That would be like I wanted some place that would just be like a really fun place for, for engineers who like shipping things, you know, like there's different kinds of engineers, there's some engineers who just sort of like arguing on email all day. You know, the people who spend all day arguing about politics or whatever are not the ones we want, but like people who love to like ship products. And so some other friends from Google Bret Taylor and Jim Norris, they left and they were actually looking to start a startup as well. So we started kind of having lunch with them and talk to them.

They were Google Maps,

right. Yeah. So, so Brett was the original PM on Google Maps and Google Maps, people you'll see again on hacker news like, oh, Google just like acquired and launched it. But the thing that they acquired was actually a Windows app. The original, like the startup that they acquired, it had a Windows app. That was the mapping thing. It wasn't even web based. So they converted it to be a web based thing. And then the story I always remember with Bret that I think is like, super impressive is that internally, the Google Maps wasn't very good.

It was just like this horribly slow and clunky thing. And the person who had been building it was one of these, one of the engineers I think had fallen in love with XML had way too much XML bloat. Anyway, Bret got frustrated with this and like over a weekend, rewrote their entire job for Google Maps and he made it if I remember correctly, like a third, the size and 10 times as fast they show up on Monday and he's just completely replaced all of the code. That's the kind of engineer Brett. And the thing is it isn't bad code. Like it isn't like sloppy stuff. He'll crank out really high quality code very quickly. So he's, he's like, he's not even a 10 X engineer. He's like 100 X or 1000 X engineer. It's just

ridiculous. That's the person you want to be at your company that you're starting, you,

you definitely want, want that on your team. So, so yeah, we managed to convince to join forces. And so, and so we launched Friend Feed Then I think it was August 2007 if I'm remembering right? And

tell me a little bit about friend feed. I mean, I think it was, you created the idea of like following people,

know, I mean, I think following was already around. So friend feed, it's kind of started off as it was, I guess sort of the Cambrian era of social, there were like a million different social things at the time and they all had these feeds. So you could have like an activity feed off of videos that you post on youtube and like things on Twitter, things on Twitter was already out with it with the follower graph. And so there were all these different RSS feeds and things like that. And so the original idea was that you can kind of like pull all of them together, all of the social activity from different places and aggregate it together and then create this environment where you sort of see what your friends are doing across these various social products. And then very quickly we added comments and then actually we also, I think it was like October 2007, we launched the like Button. So is actually the original like button though this claim is, is somewhat disputed by but version of the story, which is that they had community but just forgot to launch it. The story was that they had made a very similar feature internally called The Awesome button. But then they never launched it because it was like lame

because it was not, not awesome

because it was not awesome. Yeah, calling it the Like button. So after, after we launched the like button, they sort of like dusted off the awesome

button and remind me, didn't Facebook sort of copy everything you did once you guys launched it or am I wrong?

Yeah, I mean, so they, they don't know about everything but yeah, they definitely kept a close eye on us and Facebook, you know, I didn't really know too much about them at the time. I sort of hoped that they would be too successful to be nimble, but that's definitely not the case. Like, they were very willing to move fast and break things and whatever they're, they're, they're a very aggressive competitor. And so one of the things that happened, you know, being in the social space for that period of time is you start to sort of realize like which people are really good in which people are clowns. So,

like at one point we were talking to like my space, like we flew down to L A to meet with the people down there and it was just like, it was just a disaster. Like they went silent on us for a while and then all of a sudden he gets back to us. He's like, okay, I think we can do a deal, but we have to throw a lot of people under the bus and, like, just weird, just like weird clown show stuff. And, you know, Twitter was always in constant disarray and, you know, versus like going in to meet the team at Facebook,

they just clearly understood what was going on so much better than everyone else that it was just like, no one else stands a chance. You know, people that still had no idea what they were doing with social. So it just sort of became readily apparent that basically Facebook was gonna win it because no one else was, was even close.

Well, to take you back for just a second. Why did you start talking to these companies? Like, did you know that you didn't want to run it independently or?

No? I, I never wanted to sell initially. I mean, I was trying to create a place that was, you know, a really fun place to work. Facebook again, kinda to their credit had been basically reaching out to us from the start, like, hey, we got, we should work together, hey, you know, so they were always like wanting to talk to us. Um And so they would bring us pretty frequently we with front feed kind of reached a point where our growth had kind of plateau owed.

And so the problem, ultimately, you know, our product, we, we never really had the right product is basically the right answer. We were too, we were too similar to Facebook and Twitter who were both much larger and more successful. And so, like we had really great growth, like when Twitter would have the fail Whales. So like when Twitter was down, we would have great growth. But that's not a long term strategy. Like eventually they figured out how to keep the service up. And so we needed to either pivot or sell,

looking back, you know, one of our pivot ideas was basically to build Slack or something. Cause one version of the product that work was we had these things, we called internal rooms that were basically like slack channels. So like we could have done that or whatever. But given that we're sort of at this inflection point, you know, we were like, well, okay, maybe we should, you know, Facebook, reach out to us. We're like,

okay, well, if you're so interested in acquiring us, you know, make an offer and they're like, well, how much do you want? So we had this ridiculous back and forth. We were like, well, you're the ones who reached out. So, you know, you have to do and so they're like, well, if we make an offer,

you know, we'll just lowball you. It was a lowball us, right? Okay. Okay. So there was sort of a whole back and forth. It was kind of a crazy negotiation. So, so then when they finally did come make the offer, it was actually this really funny meeting. They come over to the office and then kind of we make tea or coffee and like, sit down and they sort of like slide the offer over and we like, look at it and it like sort of like low ball buster. Okay. Well,

thank you for your time. I'm just gonna sit there quietly and Chris was like, can I finish my tea? Can we finish? They said we just like an awkward couple of minutes silently waiting. Well, everyone finishes drinking there, there was no

even discussion. It was, it was such a lame offer because

they were just like, okay. Okay. Thank you for your time. And they did a terrible job of pitching it to, they didn't pitch it anyway. So, yeah, just goodbye and then we just sort of stopped answering, We just stopped responding to them and then, but we were also talking to Twitter and actually had gotten pretty close to selling to them. I had sort of like, concerned about Twitter. And I'll tell you this is sort of an interesting story. When we went in to talk to them. It was a different experience from Facebook. There were like 10 people in the room or something like that and They're telling us about the structure of the company.

And it's kind of like, it's almost like engineering is like one of 10 things. And the thing that's hilarious for me now is, like, with sort of the Ellen situation, it's all coming right back to the surface. It's never been an engineering company. Right. And so for the first time ever, he wants to make it into this, like, engineering centric company. So it should be fun to watch. You know, I, it was a really weird thing.

I got this, like, just sense of hostility from their VP of engineering. Like, I don't think he liked us and, but, but the part that ended up being really, I thought funny in hindsight was a year later, every one of those 10 people we met with were gone. Really, the entire management team had turned over within a year. It was just like a very unstable place. So, I don't know all the drama of what was going on behind the scenes, but it was just like, yeah,

it was like weird stuff. So, yeah, I sort of like, then had a little bit of this epiphany where I'm like, well, if Facebook is obviously going to be the winner of this whole thing. Well, first of all, it would just be interesting to see, you know, because I'm a sort of a curious person, I'd seen Google and I wanted to kind of know what another one of those things look like. And then also maybe some level of arrogance. I thought we could be like a positive influence or something like that. Like you can make Facebook good.

So, yeah, I, I then like responded to on like a Friday. I'm like, okay, can you chat? You know, because we've been ignoring their emails for a few weeks and so I went over on a Friday afternoon and was just like, okay, look, there's three reasons we can't sell to, you know, to Facebook. First of all, everyone hates Facebook.

Like secondly, your offer is terrible. And third, I don't want a job. So I'm like, all right, here's, here's, here's where we stand. So he spent about like four hours or something walking, walking around Palo Alto and kind of talking and then eventually reconstructed the deal in a way that I thought was like a really good deal for everyone. And so we basically came up with better terms, higher value in some way of kind of revaluing Facebook to make the deal more attractive. And so then basically did a handshake deal that night. And then on Saturday, we discovered that we didn't have a lawyer because our lawyer had gone fishing.

Yeah, literally because we just had some weird little like, like lone proprietor or something like that and he was, he was gone, he was offline and here we are trying to sell our company. And so we scramble all Saturday to try to find a lawyer and no one wants the deal because it's like you're gonna have to work really hard and then you're gonna have like a permanent conflict with Facebook or whatever. But we finally found some lawyers by like Saturday night and then all Sunday, like they're working like crazy to get preliminary docs in place. And then we actually signed the documents Sunday night, announced until Monday. So, so we, we went from, from Friday morning, we woke up with nothing. I E mails we like have a handshake deal Friday evening,

Saturday, we look for lawyers Sunday, Sunday night, we signed the deal on Monday morning, we announced it to the

World Caroline. Are you stunned and impressed right now? Yes, I, and I feel terrible for that legal team. But honestly, like, what was the rush?

You know, just like speed, we even speed. It's just your thing. Okay. There's this, this, this like Sort of rule of thumb that one of our advisors gave us. I like to tell the startups sometimes just like every, every day, the deal doesn't close. Like the odds that it closes goes down by 10% or something like that. Like if you're gonna do the deal, do it now, right? Like, like every day that goes along is it is an opportunity for something to go against you. That's true. That's

true. I just have to say PB I miss all of your keen insight. You just like distill these little tidbits of knowledge. That you dropped, that are like so kind of profound and important, like startups should listen to you and just make a book of like all of your advice from start to finish. But back to Facebook was

super persuasive super. But, you know, like I said, I, I um I was impressed by what they had achieved, you know, like they were just clearly more competent than everyone else. And so I'm like, okay if we're going to sell our company, it would be interesting to go someplace where like people actually know more than we do. Like, like we could have gone back to Google and led one of Google's, you know, additional failed social efforts or whatever. But like, why would that be fun to just go,

like, fail at this thing again? Like we could have, we could have gone and built what do they call it taco time or something? Buzz was what they were working on. Like Google had a series of these failed social efforts like Google. Plus, it was just like the last of several,

I don't even remember what they were. So, so the friend feed team goes to Facebook. So you're now at like the second greatest tech company of that generation. And what's that like for you guys?

You know, I started to sort of regret my, honestly, when I found myself in a windowless room in the basement, I'm very sensitive to lighting conditions and I was like, what happened last week, I had my own start up and everything was wonderful and I had sunlight, had some light now in a, in a basement, you know, it was interesting. So I, again, I was just kind of curious about it. So I was trying to figure out what sort of role I would even want inside of the company. So I decided to just go around and just kind of interview lots of different people and try to understand like what was working and what wasn't working because, you know,

you start getting all these different groups inside of the company who, who are unhappy with this or that. So I spent a lot of time just talking to different engineers and getting like the history of the company and like what they thought was good or bad. So I spent a lot of time just like learning about it. So it's actually pretty interesting. It's a very different history from Google. Google hired really smart, talented people from the start. Facebook had a really hard time hiring technical people early on and the founders were kind of amateur. They weren't like great engineers or anything like that. I remember talking to the one guy who had two blanking on his name, but he was kind of the first sort of like adult engineer higher that they had, who had to try to convince them to use revision control. Like they didn't use source control, they would just sort of like, they were just sort of like,

edit on the Harvard server and then if it looked good they would SCP it to the other servers, you know, and they, and they didn't bother to do any revision they didn't use, you know, obviously they get, but they didn't use anything of that sort. So it was a very different, the company had a very different history. It was very, very hacker in the sort of like messy hack kind of sense of things. But they really valued just like launching things quickly and hacking and that kind of stuff. So it was kind of interesting, very different culture from Google though. Really?

I thought so is one better than the other,

you know, it depends what you like. But I, I, um, maybe it's because I spent longer there but I, I generally liked the Google Google culture, more Facebook. Yeah. I don't know how to, how to put it in terms that I'm uncomfortable stadium. I, I think like, there was, there was a higher degree of like, technical ability, you know,

and, and, and, and just, I think just sort of the systems thinking at Google was, was, was more interesting, you know, you had a lot of really good leaders. I feel like Jeff Dean who all the Google engineering really respected because he was just, like, really smart, really, you know, thoughtful. Like you had a lot of that kind of leadership that,

that Facebook didn't have as much of that history behind it. And Facebook had more of a kind of like their version of hacker is a little bit closer to trickster. They were clever at getting people to do what they wanted them to do. You know, Facebook is a, is a, is a, is a very good mousetrap.

Well, um, interesting. Yeah. How long did you stay there?

So, I was there for about a year and just like, never really found anything that I was super interested in working on versus just like, not working to me, especially, I guess, you know, partially in light of my brother's death, I always kind of have this thought in mind. Like, is this really what I want to do with the rest of my life? And so the idea of like sitting in a windowless room when I could be, for example, outdoors, you know, I have to ask myself, why am I doing this?

Like, why is this what I'm doing with my life? Because I have no economic need obviously, like, why is this the thing that I'm choosing to do? And so if I like really deeply believe in what I'm doing, then I can sort of rationalize it that way. But if it's just kind of like, well, it's so that I can get people hooked on Facebook slightly better or whatever. And like, so you're the only, the only feature I ever launched actually at Facebook was the account export and download feature, which became popular a couple of years ago, long after I left. So you ever, if you ever do the thing where you download your Facebook as a zip file? That was, that was my one and only addition to Facebook. I've done

all my photos but not all the stuff there.

That thing where you can click to download, you kind of have to dig through but that, that you can click to download a zip file that contains all of your, all of your Facebook. Just

wrap up your whole thing, turns

it all into a zip file with a static html. You can click

around. So PB then you came to Y Combinator.

Yes. Yeah. Actually, the funny thing was I, you know, when I was thinking about leaving Facebook, one of the ideas I had was at the time read, it was sort of like withering on the vine or whatever because it was still belong to Conde Nest, but it wasn't getting the resources. So they were like begging for money to keep their servers running. And like this is really stupid. I wonder if they would just sell, read it to me. So I, I initially went to PG and it was like, do you think they would sell me, read it?

You know, like if I asked and he's like, no, you don't want to buy Reddit. He's like, you don't want that, you know you oughta do you oughta come to Y Combinator?

Oh, well, I can't believe that he dissuaded you from making Reddit an offer. But I'm delighted that he said come to come to white. He's

so scarred from running hacker news. That true correctly identifies running a community as being sort of like one of the most painful things

you can do. I can't imagine you would have enjoyed that. Paul.

No, I think he would. I think he was right.

Actually. So when you joined YC, we had already had a relationship with you because you used to invest, you'd come to our demo days and used to invest in a lot of YC startups. You were like family when you joined. But did you like working at YC?

Yeah.

Yeah.

It was very different. It was, it was kind of more the realization, I guess I had towards the end of Friend feed and being their Facebook was that actually, you know, I have kids and maybe I want to spend time with my kids and maybe, maybe like, actually Working 100% of time on the startup isn't really the thing I want to do with my life. And so, you know, YC was great because I could be involved with startups. But at the end of the day, none of it was my responsibility. Like the really great thing is you can stop and talk to the startup and I'm like, this is what I would do. Here's what I think you should do. You can follow my advice or not.

I don't care, you know, you write if you, you, you know, this is why we find a lot of startups, right? Like some of you are gonna fail. You know, it's not my responsibility to make you a success. And so that's, that, that works better

for me. Now, I think the numbers have proven now that you were amongst like the best startup picker at Y Combinator, right?

I don't know, someone did some, some statistical thing at one point. That was a long, long time ago. So,

but it leads me to ask, I mean, obviously at YC were exposed to so many different startups. We see everything and you did so many angel investors, angel investments on your own. Have you gotten better at picking startups? And what does getting better consist of?

I hope so, but it's, it's hard to tell because as always, it's driven by the outliers. So it's easy to, you know, if you just miss one outlier, then you, you fail. Yeah, I mean, the biggest thing, it always comes down to the founders and we say this over and over. But unfortunately, it's true. The trap I fall into most often is wanting something to work even though I know the founder is not really that great, but I like I really wanted to be a success.

And so that's my number one source of failure, I think in terms of investing is that I invest in something that, that I know the founder is not really that great, but I just sort of like, convince myself maybe if I just like, believe in them harder,

maybe it'll work,

never worked for me. Like the founders just have to be good. No amount of me wanting them to be successful seems to, which

has been your most successful financially, angel investment.

I think probably doordash. I mean, Stripe Stripe will be presumably someday, but, you know, they're not public so we won't have that yet. Oh, interesting. I'd have to go back and look if there's anything, anything closer. But yeah, I mean, certainly you can't beat large numbers again. That's the, I think that one of the things that's counterintuitive to people is that there's a tendency to fixate on percentage ownership, but it's never the percentage ownership that makes you a great, really great return. It's the, it's the really great return that makes it really great return,

right. What other key advice would you give to people doing angel investments? Like that's a, that's a big one. It's better to be invest, you know, be an investor in the most successful company than have a bigger chunk of one that fails obviously. But what other

good advice is there? You know, I mean, I think like it helps if, if they're making something that you personally want and I don't know if that's just coincidence or everybody, you know, this kind of goes back to actually just having a great product is like, is there really evidence that people want this thing? Because the most common reason a startup fails is that they didn't do what it says on the T shirt, which is make something people and there's a million in one ways that you can kind of like fool yourself into thinking that you're making something that people want as a YC partner working with the companies, right? When they come into Y C, I always felt like my number one thing was to force founders to have the realization that no one wants what they're making because most of the time, that's the state of things. And so the thing I would always push them to do is like, okay, go get yellow eyes,

go somehow you gotta go get your customers to make some sort of sacrifice on your behalf. Because like if they won't even sign a non binding piece of paper that costs them nothing to sign. How are they ever going to write, you know, 100 K check or whatever it is, you're gonna ask them to do down the line. If they really truly desperately want the thing you're making, they should be willing to jump through some hoops to help you out or to demonstrate that this kind of again, goes back to wanting something to be successful sometimes sort of the other categories. Like, there's a pet idea where you think it's like a cool idea, but it sort of turns out that it's not the thing that anyone really actually wants in reality, for example of this would, of course, then be back to doordash. Doordash was the thing I was looking for.

So I've been wanting to fund doordash and in fact, I had invested in Caviar as well prior year, but they only were operating in cities and I lived in the suburbs. And so when doordash, you know, interviewed, I was like, if we fund you, will you deliver food to my house?

I remember this

initial, the initial delivery area was, was Mountain view and, and you know, like the part of Los Altos that includes my house. So, but you know, it's the thing I use constantly. I, you know, it's great. We if we go out, we order food for the kids or, you know, I order lunch, something like that. So it's like I have a regular need

to eat. You are a happy user.

Yeah, I'm a frequent user.

Yeah. As a fellow suburbanite, we appreciate doordash all the time to teenagers all the time. In fact, we got an email from the high school that said, please remind your student they are not allowed to have doordash delivered to school.

Oh, yeah.

Yeah. Yeah. My 13 year old when we come back to Palo Alto, he's on my phone ordering doordash for like every meal possible. What else do we was, what other, was there any last minute questions be? Well, this is not a fully formed question, but I have noticed that you've said the word fun, like a whole bunch of times as we've been chatting all this time. And so, and I think because you've explained really well, kind of what you mean by that. And I think it's, you know, satisfying curiosity and being fulfilled in what you're doing and having your work,

you know, something that you, you, you know, you ship fast, whatever. What do you do now? Like, what's your life like now where you get that, that sense of fun?

That's a good question. Not having enough fun. Uh

Come back to YC was going to say we can make arrangements.

Yeah. Right. I, I spent a lot of time with my kids, you know, like every morning actually walk to school with. So I'm waking up earliest I've ever woken up at 6 22 walk, walk to school with, with cam at. So it's like 2.5 miles to school and then, and then I walk, walk to school. So every morning we walk and have like a nice discussion. It's great, you know, it's like, you know,

that's, that's precious time, right? Like kids grow up. So I try to spend time with the kids. So, yeah, every morning we walked to school have, have a good talk about, you know, she's very curious about the world and likes me explaining whatever we talk about the ego and like strange things Michael Jackson was talking about Michael Jackson a lot. And, uh, and then I, and I run home and then, you know, just depending on the day I usually go to yoga at some point. So I exercise quite a bit. I run a lot. I go

to yoga a lot. You look like you have not aged at all. Unlike me who COVID was very unkind to you look like haven't aged at all. I said that to you last year at your birthday. I was like, damn PB is not getting older.

Try not to aging. Aging, aging is a donor. So try, we try not to age and working on handstand. Eventually. I'll have a really great handstand. It's been about 10 years, I think a couple more years and I'll really have it.

Well, gosh, I have to say this has been the most fun I've had all day. Like this has just been so much fun catching up with you and chatting with you. And like I said, you have, you've had so much experience and I've had so many interesting things happen. So I appreciate your time. We'll hopefully see you, see you in California sometime.