YC Partner and the creator of Gmail, Paul Buchheit in conversation with Geoff describes how he thinks about companies that manage to scale to the ultimate level.

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It is now my great pleasure to introduce my longtime colleague at Y Combinator, Paul Buchheit.

Paul is known for a lot of things, not the least of which is his wisdom and all things when it comes to startups, but he's also of course the creator of Gmail, the inventor, this is true, of Don't Be Evil, and has a has had an incredible career.

So I just thought I'd turn it over to Paul for a couple of minutes for him to describe his journey from somewhere to, into YC and what's happened then.

And then we're going to have an interesting conversation, I hope, on what it means to build an epic company.

So yeah, I grew up in the Midwest and I went to college in Ohio and like in the 90s, which is different from now probably.

Yeah, everything in the 90s was different.

So yeah, I was always interested in startups, and like, even as a kid, like this idea, I think I just didn't like the idea of working for someone else.

And also I liked the idea that you could make a lot of money and create cool new inventions, basically.

You'd read about inventors like Tesla or someone like that.

You're like, wow, if only that guy were smarter at business.

He invented so much and he died penniless.

I'm not sure if he actually got any equity.

So yeah, I was always kind of in the back of my mind.

But as I'm coming up to graduate college, which was in

so I was very interested in startups, but there really was, there was obviously no startup school, there was no Y Combinator, there was none of, there's basically very little, the web was relatively tiny at the time, there was not a lot of resources, I didn't really have any connections, I didn't know anyone who worked at a startup, but I suspected they were in California.

So, just always doing the simplest thing first.

I mean, eBay, Netscape, that first generation, Yahoo, all of that first generation of internet companies, they had already, you know, those companies are IPO'd by the time I graduated, so

they were all located here, you know, with the exception of Amazon up in Seattle.

have to be that smart to figure out where Silicon Valley is.

So I took a job out here at Intel, kind of with the hope that I would just like, you know, there'll be startups everywhere.

And that was, you know, Intel's a big company.

I don't wanna like, but it wasn't something I look forward to like continuing to do year after year.

used to call working at HP where I first worked the fur-lined rut.

Yeah, I actually have a specific memory, like, hanging out with a couple of other friends who worked at Intel, and, you know, I'm like 21, 22 years old, something like that, and they're talking about, like, oh yeah, they've got this really great, like, retirement plan where, you know, if you work there until, for however many years, your age plus your number of years of service, you could retire at 55 or something.

Like, oh yeah, why don't I just take the next 30 years of my life and stick it in a box and bury it.

There are people there when you're sitting there at 22 who have been there for 30 years, who are just kind of doing their time.

Yeah, so I wasn't really into doing time.

I had gotten interested in Linux actually really early, like 93, when it wasn't actually very good.

And so I was kind of like an early Linux zealot who was like, oh, this is so awesome.

And back then, businesses didn't really, Linux wasn't like a serious operating system.

They're like, no, serious businesses will always use Windows.

You need like an enterprise operating system, Not some hobbyist junk.

So I was like looking for something to work in Linux and because I you know everything at Intel was like pretty much Windows based.

And so that was my criteria when looking for startups was just that I wanted it to be kind of technically interesting Linux stuff.

Again, there weren't great resources on a huge list of startups.

So I just kind of scouted out what I could find basically on Slashdot, because I would read Slashdot a lot.

And I came up with a list of 6 startups that seemed like they might be interesting doing stuff with Linux.

And so I just emailed my resume to all of them.

Sort of ironically, it immediately bounced from Google because their mail server was misconfigured.

So I didn't hear back from most of them ever.

I interviewed at 1 other company and then I resent my resume the next day and then it went through, they had fixed, I think the MX record was broken or something.

So I only interviewed at Google and 1 other company.

And the other company, I wasn't interested, and I think maybe they weren't interested because neither 1 of us really contacted each other.

And so Google was really the only offer I had.

And so we were in Palo Alto on University Ave, kind of on the second floor above what is, I think, a bookshop or cafe or something like that.

What did it feel like at Google when there were 20 employees there?

I was really impressed when I was interviewing with them that they asked actually like really smart questions, which I think is a pretty good indication.

Like that was 1 of the other reasons I wasn't excited.

Like the other startup I went to that I interviewed at, it was just like I went into their office and I just sort of felt depressed.

Like You could just tell people weren't really that excited to be there.

And then they'd ask dumb questions that I didn't think were like, anyway, it just wasn't a good sign.

Versus Google, they were into whatever it was they were doing.

And actually, after I was there for maybe like a week, I went back and I'm like, hey, I want more equity.

And they're like, sorry, you have to negotiate that before you start.

been like the smartest pseudo-investment decision you've ever made, even though it didn't, I guess it worked out, but.

Yeah, I mean, it worked out overall, but yeah, I do wish I'd gotten more.

So, the thing about the office, I mean, you asked about the environment.

Like, it just had like a very, kind of like a buzz of productivity, right?

Because we were doing these really kind of exciting things and I think like they had hired people who were really into building these like big systems and creating great products and everything.

So it was an exciting place to work where I would actually wake up in the morning and be kind of eager to go to work because I've got stuff I want to do.

Do you think that was because, not just they were working on exciting things, but because they believed they were going somewhere?

Yeah, I mean, there was kind of like an irrational belief.

Right, like objectively, we were just this tiny little company or whatever, but Larry would be talking about whatever crazy ideas, we were just like, wow, what?

Like I remember having an early memory where I was building this system and then I'm talking to Larry about, he's like, why are you even bothering with the disk?

We're just gonna store everything in memory or whatever.

Which at the time was sort of an absurd, you know, we didn't have enough RAM to store all of the data.

But he was always thinking so many years ahead and it was a little bit insane, but it made it a very exciting place to be.

Yeah, it seems like there's something fundamental.

If you're thinking about whether you have a, the potential to build a really big business, if you don't have some sort of vision, some sort of idea of a future, it's hard to believe you're ever gonna get there.

Yeah, I think you have to have some notion of the big picture.

And it doesn't mean you have a detailed step-by-step plan.

Like occasionally I'll run into a startup where they're like, here's our five-step plan for how we become whatever.

And it isn't until the fifth step that actually they have a product anyone would want to use.

I mean, you have to have something today that's good, and you have to have something tomorrow, and you have to, day after day, have a product that people actually want.

Yeah, you almost want a certain amount of vagueness around your vision, because if you have too much detail, You're just guaranteed to have wasted your time because it's not going to be right.

wow, that's just about how long you've been at YC now.

When did you realize that Google was a thing, that it was gonna be like this secular juggernaut that was gonna take over the world?

I didn't, I think, like many people, I continually underestimated its potential.

But, you know, from very early on, kind of like after being there for a week, I was like, ooh, there's something magical going on.

I didn't think it would be what it is today, as big as it is, but it definitely felt like we were somehow creating the future.

And then when we started really like, like when we got the Yahoo deal and started like really displacing, yeah.

When we started really just like pushing all, just crushing all the other search engines and then there was like a feeling of inevitability.

It was pretty clear we were just going to win because no 1 else, they just didn't even know what they were doing.

Before we move on to leaving Google and starting your own company, just maybe say a word about the founding of Gmail and how that happened.

So email was actually a thing that I'd been interested in for a long time.

So in college, I had actually been thinking a lot about this, because like, again, back in the 90s, like people, their email would download to their computer.

They would run like Eudora or something and it would use POP3 to pull the email down to their computer.

And I remember people would be like, I need to go to my room to check my email.

It shouldn't be like stuck in a box, right?

And so I'd been thinking about this idea that everything's just gonna be online and then we'll just be able to access it anywhere, anytime we want.

I think, I kind of had gotten maybe a little bit excessively arrogant and had only applied for like a couple of summer jobs, just assuming they would want to hire me and they didn't.

And so I actually tried to start this thing of like a web-based email.

That's funny, because that's right when we were building web-based email.

Anyway, I had like grand visions for it, but my approach to developing it was was wrong.

It was it was very much like I had this great big grand vision and then I started trying to implement it piece by piece, the components, and then I got bored and gave up.

It's actually a multi-person job to build email.

But the way I went about it was kind of wrong because it was like I actually did sort of this detailed design or this very intricate system and everything.

And I've kind of come, at least for myself, I've come to decide that that doesn't work.

I need, and this is what we preach to the startups, is figure out what you can launch today.

And so to jump forward to Google, like it was kind of 2001, there was sort of a big reorg where they got rid of all the managers and just gave engineers more of a free range engineering thing, gave us all projects.

And so, there's, like, I should build an email thing.

Like, they knew I kind of had an interest in email, or whatever, but it was just like, we want to do something in email, we don't really know what exactly, like, just go build it.

So, having learned from my prior experience, I decided to, I kinda know I have a short attention span, so the very first version of Gmail I wrote in a day, and it wasn't very good, But I took, I had previously been working on Google Groups, which was like a Usenet search at the time.

But I took the code that I'd been working on for that and then I just like took all of my email and shoved it into that database, into that indexing engine.

So your first thing was just an email you could search.

And so then I emailed that out to the engineering team.

I'm like, hey, I built this email search, let me know what you think.

And then people reply like, yeah, it's OK, but it would be better with my email instead of yours.

So I'm like, all right, I have a feature request.

And then the next version, I made it so it would search other people's email.

But there's a stunning lesson in there, I think, which is the point wasn't so much that whose email was being searched.

Like, you guys got to realize, back then, you couldn't really search email.

All you could do is find the email you wanted and click on it.

Yeah, and I figured, I mean, a lot of our email is in common, so it sort of works.

We're on a lot of the same mailing lists.

So yeah, so then version 2 is just like it indexes other people's email.

So I send that out and then people are like, all right, this is cool.

Now I want to be able to reply to 1 of the messages.

And so the whole thing was just iterating, to step by step trying to make something that would make people happy.

And so we actually had as our kind of like launch gate, this idea that we needed to have 100 happy users inside of Google, because we hadn't launched it to the world, obviously.

And so I actually embedded in the interface this thing that would pop up and be like, are you happy, yes or no?

Are you happy with, you know, Gmail or what was at the time known as Caribou?

And I would get a list then I would look at of who said yes and who said no And then I'd go to all the no's and be like, what's it gonna take to make you a happy user, right?

And some of the people, they're like, it basically has to be a clone of Outlook.

I'm like, well, you're never gonna be a happy user.

Though actually I did end up getting a lot

I did end up getting those people and the way I would get them is that Outlook at the time when you would hit 2 gigabytes in your mail file, it would corrupt the database and they would lose all of their mail and then I had the only copy of their email.

And so then they would become a Gmail user.

Not always a happy user, but they would become a user.

But anyway, other people, it would just be like a minor thing where like, I just need to add 1 feature or like fix a bug or something and then they'll be happy.

And so we kind of slogged through like just 1 user at a time until we got to like 100 happy users.

Is that the genesis of what we call it, why see the Bukhait rule?

Maybe you can just tell these guys what, like it's better to have 10 or 100.

Right, so 1 of the ideas is like when you're starting out building something new, especially if you're kind of going into an established category like email, like literally email was like 30 years old when we started on it, right?

So there is a lot of history and a lot of opinions about how email should be.

People would sometimes angrily tell me I'm doing it wrong because we made the reply on top instead of the bottom or weird stuff like that.

So it's pretty much impossible to enter a space like that and make a thing that appeals to everyone.

And if you try to do that, what you end up making is just like a mediocre product that nobody really loves.

And so my philosophy and what we try to get all the startups to do is figure out a thing that will just have really deep appeal.

Even if it's to like a tiny fraction of people, If you can make that small fraction of people just obsessively love what you're doing, it's easier to then grow that group.

Because there's always people at the margin where if I just make something slightly better, they're going to join into that group.

So it's easier to start with that deep but narrow appeal and then broaden it over time than it is to start with just sort of like broad meh and then try to convert people from meh to loving your thing in mass.

Yeah, I've been thinking about that lately, just in terms of retention.

Like if you get 100 people who never leave, that's a great place to start than if you have thousands of people, all of whom churn eventually.

Okay, so Gmail happened, and then you left.

Yeah, so Gmail happened and yeah, a couple years later I left the company.

Kind of, you know, it was becoming a big company again and I just decided that wasn't the direction I personally wanted to go.

And I just had a baby who had a pretty traumatic start on life.

So actually around that same time, actually even before I left Google, I was again reading Slashdot because that was where I got all of my information.

And I saw this thing about the Summer Founders Program, which I thought sounded super cool because I'm always just like looking for an idea that's actually novel.

For those of you who don't know, the Summer Founders Program, that's YC.

That's the 1 that had Reddit and a bunch of companies that didn't make it.

Sam's company, Justin and Emmett's company, Kiko, were all in that batch.

Justin Conn is the founder of Justin TV and Twitch and Atrium.

I didn't know Paul Graham or any of these guys.

So I was just kind of like keeping it on my radar.

And part of that was my own experience kind of like being there in Ohio and thinking like I'm excited about startups and I wouldn't even know where to begin, right?

Because I don't, like if you go to Stanford, like your roommate probably has a startup or something, like it's just in the water.

But if you're from someplace else, if you're not from Silicon Valley, if you're not from this environment, it feels like you're just excluded.

And I really liked the idea that it was just this open thing.

Like anyone in the world, you didn't have to know anyone.

You could just submit an application and they were gonna bring you in.

Turns out startup school's the same way now.

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The Path to $100B by Paul Buchheit