We may never achieve a utopia, but it is worthy and worth it to attempt. Everything that's awesome in my life is kind of a cult. We had to go over to the Windows team. They wouldn't reply to our emails. They wouldn't fix our bugs. And we had to go over there with a baseball bat. An org like Microsoft can't.
Gary, so good to have you, brother. Thank you so much for joining us today.
Amazing, dude. Well, we're going to cover a bunch of the basics, then we're going to get into the advanced topics to make sure that we kind of match the curiosity, ambition of our audience.
Does that work? Awesome. Well, dude, maybe talk to me a bit about the beginning of your journey in 2003. You know, it feels like what's under-discussed is founder psychology and then sort of Silicon Valley culture and how the two are connected. What did it feel like when you first got in the game back in 2003, coming out of Stanford?
I guess I wanted to work at startups, but 2003 was funny in that like Web 1.0 had just ended, like the NASDAQ had just crashed, and actually there were no jobs that I could even find in the Bay Area other than, you know, working at Gap IT. And so the two job offers I had were Microsoft for Windows Mobile, which I was pretty excited about, or Expedia.
Yeah. I, you know, I had student loans and I, you know, while I wanted to start a company, I just, you know, felt like I needed to get a job. And then actually there were no jobs in the Bay. It was like kind of hard to believe, actually. That moment was so bleak. And then right before Web 2.0, it felt like it might have been the end of tech.
Right. A little bit. Yeah. That was the vibe. And then, you know, at the end of the day, like that's the boom, that's the bust. Like these things sort of happen over and over again.
So at the time, did it feel high status to work in tech or on startups?
Not at all. I mean, you know, it's sort of lost to the sands of time, but I was still excited about tech, though. You know, I had done a lot of web programming, and then one of my regrets actually was I was sort of chasing what was hot instead of what was clearly the thing I knew. Mark Zuckerberg was probably doing Facemash around then, around 2003, and then Facebook didn't even exist yet. And I was getting out of web programming at exactly the wrong time.
Because it felt like that was the smart thing to do.
Yeah, it was smart. And, you know, I mean, this is true now. You know, in front of all these people at Startup School, you know, I sort of started this don't larp meme.
But I think like that's embedded in this idea that like you should just be earnest.
And then you shouldn't follow what the crowd is saying, right? Like at that moment people said the web was dead, but that was sort of the perfect time to work on web and social and things like that. And, you know, I didn't do it. I ran off and said like, 'Oh, well, the next hot thing will be mobile.' So I wanted to work at Windows Mobile, which was true, but why did I give up like the thing that could have been the next thing?
What I love about what you're saying, though, is often when we hear earnest, we think naive, but actually what it sounds like you're saying is there's like earnestness is a sort of result of maturity and courage. Is that...
Courage is actually, I think, the right thing.
Like if you know something, it sort of, if someone just like comes and contradicts you, or even if like a blog post or like someone on Twitter contradicts you, you're like, 'Well, I don't agree with that because I believe my own direct experience.' Yes. I know that I'm not a time traveler because if I was a time traveler, I would have sent a message back to myself and said, 'Just stay on working on web stuff.' Like you literally have five years of experience on top of everyone else. Like you could do an end run around everyone. Like you could have built like any kind of social software.
But instead I was, you know, I was 22, so I was like being whipped around by whatever I could read in the Wall Street Journal. And, you know, the classic question I'm sure you get that, you know, all investors get all the time is what's hot and what should I work on, right? And that's the wrong question to ask. Like the right question is like, what are you interested in? What do you know uniquely? And so that's like, you know, one of a great many mistakes I made in my career. I feel like I'm a little bit doomed to be the first principal storyteller of all the mistakes that I made in my career.
I think that it's very inspiring for founders to hear your own journey and your own mistakes and then not feel so bad about the ones that we've all made along the way.
I mean, maybe talk about the culture of Silicon Valley today. You know, on one hand, maybe it was despondent 20 years ago. It's crazy to think that was just 23 years ago that you're talking about. Now you think we would all be incredibly elated. Yet there's this undercurrent. Maybe it's the larping thing that you mentioned. You know, it's being outside of the light cone, the permanent underclass. Where does that come from? Do you think there's any truth in it? Talk through that.
I mean, I get it. Like, there's just more competition than ever. And then I think maybe it's just that we're spending too much time in distribution. I think Chris Dixon talks about this all the time where, you know, you're in the idea maze, but the cool parts of the idea maze are like the weird fringe parts, actually. It's always like, what is a toy? And that's the pattern in Silicon Valley over and over again that bears repeating, right?
Yes. Like the idea that you could have a computer on every desk in every home.
Yeah. Today is like, of course, like that's what's come to pass, but the people who created that thing, they were fringe weirdo punks.
Totally, yes. They were outsiders. I mean, Homebrew Computer Club was not where you were getting laid.
Yeah, that's true. You just were like following this weird obsession that, you know, actually I want my own computer.
And I think Chris has said this too. I think a good measure of how interesting the thing is is can you find the edge. And for the most interesting things, you typically can't. Even if you find the edge of the conversation, you can't find the intellectual edge, which I think is a very good sign. I mean, I had this growing up in the '80s, maybe you had this too. There was sort of one way to be cool in grade school and probably in high school, and maybe when you got to college you kind of found your people. And now I think one of the miracles of being an internet-native generation is that people find their people much sooner. You find your people on Reddit, you find your people on, you know, X or Insta or whatever your network is.
Oh yeah, I mean, that's the coolest thing today. Like there's probably a subreddit, there's probably a part of X, like, you know, some part of teapot that is, you know, this part of Twitter that is just your set of super weird but like really, really into that thing.
And you can find your tribe more or less instantly.
Can you talk a bit about the culture of Silicon Valley? It felt like 10 years ago it was sort of, you know, it was lower status to work on something like Palantir, either because people were nervous about doing things that were too much in the national interest or because it was sort of dismissed as a services business. Now it's clearly one of the most important companies in the world with one of the most compelling CEOs. You were early there. What did it feel like? Why did you do it?
Yeah, I mean, I have a worse story than that. I have another mistake story.
Where Joe Lonsdale and Stephen Cohen were my fraternity brothers at Stanford Phi Psi.
And then I had a job and they were like interns at Peter Thiel's hedge fund.
And Peter has this thing where you're supposed to, like, you know, when you start a thing, you write down on a piece of paper all the smartest people who you need to go and hire and like get to join you. And so they said, 'Oh, both of them were like, oh, let's go get Garry. He's up in Seattle.' Like they flew me down to have dinner with him. And he said, Peter said, 'I'm so sure this is the right thing for you. Like, here's a check for 70 grand.' That was how much I made at Microsoft at the time. And I said, 'Thank you very much, Mr. Thiel, but I might get promoted to level 60 this year.' Which I did, but I think it's like that was like a two to four billion dollar mistake at this point. And I think about it all the time. Like basically I did the same thing again. It was like the same thing that got me to go work on Windows Mobile instead of just staying on the thing that I knew and loved.
It happened again. I was like, well, I don't know, you know, I was working backwards from the map instead of looking down at the territory and saying like, oh, well, these are the smartest people I know. Like Joe and Stephen were among the smartest people I'd ever met.
And, you know, if not them, like who was I going to, you know, be a co-founder with? Like it just, you know, the universe was saying like this is the thing you need to do, but all I cared about was what was cool, what was hot, what would a really good investor say. And the thing is like they're like going off of a map. And like you can see, you can look down, you can look around, you can like have first principles knowledge of what's going on.
And, you know, what they were doing is like they were going to governments and three-letter agencies.
And it was clear that the things that really good computer scientists in Palo Alto could do and create, DC did not have access to that. And, you know, it's funny how much that thing that they had identified, like Peter and Joe and Stephen and later Alex Karp identified, that like runs through almost everything that we do in Silicon Valley. It's just like the future is already here. It's not evenly distributed. And then that's where like first principles knowledge or like just viewing the world as a scientist is actually very useful. And what a scientist does is, you know, sure there's published papers, but you go and you examine all the truths. And what you find is that once you go down into the experiment or you go down and talk to the first-party people who are experiencing a thing, then you learn secret knowledge, then you have gnosis. And so, you know, from Palantir, I definitely learned that everything that's awesome in my life is kind of a cult.
That starts with some sort of truth or belief that flies in the face of an orthodoxy, which is very punk, actually.
Yes. Yes. Dude, that's very Rick Rubin would approve.
Yeah. Yeah. Well, actually, what I love about what you're saying is that there's a beautiful truth in the fact that you've talked through some of these maybe tragic misses, but, you know, the lessons are courage, the lessons are earnestness, right? The lessons are when your instincts are pulling you to work with a set of people. So maybe talk a little bit about, you know, we talk a lot about how Silicon Valley and the magic is it takes outsiders and turns them into insiders. And I feel like YC is the ultimate distillation of that. You know, you go from being two founders perhaps from a foreign country to two people with YC on their LinkedIn and everybody now knows what that means.
So talk about how that happens. Is it a process? Is it a mindset? And how has it changed over the years?
I mean, I have to credit Paul Graham and Jessica Livingston and the original founders, including Trevor Blackwell and Robert Morris. I mean, what Paul and Jessica figured out was that there are lots and lots of really smart people who do not get access to Silicon Valley. I mean, I think in the past you had to like go to the right schools, you had to know the right people sort of, and if you didn't, you'd come to Silicon Valley and you try to get invited to the right parties. There's like a social network that you had to crack. And then at YC, we have a pejorative for that whole scene, which it's like we call them sceners, actually.
Which is, I mean, it's sort of a nod to like what you used to have to do. And some people still believe that's like how you do it. All they did was say, you know what, like here's a website, here's 12 questions. Later we added like a one-minute video. And people on the other end who are builders are going to try to give you a fair shake. And so today we have, you know, 16 equal partners, including myself, and all of us like went through YC and had successful outcomes. And I think there's something valuable to that, that just, you know, welcome to Silicon Valley. We just celebrated 7,000 people coming to San Francisco. The majority of them the very first time they came. It's, you know, our Startup School every single year.
We kind of call it like Birthright, but for tech.
It looked like the Roman Colosseum, dude.
Yeah. So, you know, I think that that's the coolest thing about Silicon Valley. Like you sort of, it sort of doesn't matter where you're from or who you are. It just actually matters what your ideas are and can you execute. The only other thing that I'd say like YC people get that a lot of people don't get is a community of people who you can be super real with. It's like if you go to a TechCrunch event, you look to the left, you look to the right, and it's like, are you really going to be able to tell them anything real? Like you're going to hold your cards pretty close and, you know, you're going to say, how are you doing? And they're going to say, killing it. And then they're going to ask back and like, oh, I'm also killing it. I mean, honestly, founders really need that. Like it's very solitary. It's, you know, on the day that you lose your best customer, on the day that your best engineer quits, like who are you going to call? And if you have no one, like I mean...
The day your co-founder loses hope and you're not allowed to, right?
That's a tough day, you know.
Talk about the historical upside, sort of surprises of like founder types, business types, and the downside surprises. What have you learned through YC?
I mean, we're sort of in the middle of a big transformation now. I think for the longest time we really, really believed that you needed co-founders. And I think that everything else being equal, having co-founders is net really, really good.
I think some of this is like the beginning of a cult, like, you know, a cult where there's only one person and that person can't convince anyone else to join them is like, you know, worse than a cult is just like a crazy person, actually.
I think this is like an old Derek Sivers TED talk, right? Where it's like, yeah, one person dancing in a field is a crazy person.
But, you know, it's really the second person who like gets up.
And joins that person, like then what you find is, you know, suddenly 10 people are there dancing, then it's a party.
