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.
Garry, 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 and ambition of our audience.
Does that work? Awesome. Well, dude, maybe talk to me a bit about the beginning of your journey in 2003.
I guess I wanted to work at startups, but 2003 was funny in that 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 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 had student loans and while I wanted to start a company, I just 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
Right. A little bit. Yeah. That was the vibe and then, you know, at the end of the day 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.
I saw that. Uh, but I think like that's that's embedded in this idea that like you should just be earnest.
Yes. 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. Um, 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. Yes. 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 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. Yeah.
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 laring 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 like? And that's the pattern in Silicon Valley over and over again that bears repeating, right?
Like the idea that you could have a computer on every desk in every home. Today, of course, that's what's come to pass but the people who created that thing they were fringe weirdo punks totally. 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.
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 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.
Yeah. Yeah. Can you talk a bit about the culture of Silicon Valley? 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. Okay, where Joe Lonsdale and Stephen Cohen were my fraternity brothers at Stanford, FAI. Uh, 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 Gary. 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. Yeah. And I said, 'Thank you very much, Mr. Thiel, but I might get promoted to level 60 this year.' Oh, no. Which I did, but I think it's like that was like a $2 billion to $4 billion mistake at this point. No, no. 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. Yeah. 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. Yeah. And you know if not them like who was I gonna, 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. Yeah. And you know what they were doing is like they were going to governments and three-letter agencies. Yeah. And it was clear that the things that really good computer scientists in Palo Alto could do and create. Yes. Uh, 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. Yeah. That runs through almost everything that we do in Silicon Valley. It's just like the future is already here. It's not evenly distributed. Yes. And then that's where like first principles knowledge or like just viewing the world as a scientist is actually very useful. Yes. 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, yes, then you learn secret knowledge, then you have gnosis. And so, from Palantir, I definitely learned that everything that's awesome in my life is kind of a cult. Yeah.
Yeah. Yeah. Well actually what I love about 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 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, 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?
Um, 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, 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. Um, and then, at YC, we have a pejorative for that whole scene, which it's like we call them sceners actually. Okay. Uh, 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 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.
So incredible.
We kind of call it like Birthright but for tech. It looked like the Roman coliseum dude.
Yeah. It was amazing. Yeah. So, you know, I think that that's the coolest thing about Silicon Valley. 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, why see 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 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 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, one person dancing in a field is a crazy person. Yes. But, you know, it's really the second person who like gets up.
And joins that person, like, then you what you find is, you know, suddenly 10 people are there dancing, then it's a party.
Yeah. That's literally the TED talk.
I think there's something to that. But you know, I think what's happening right now with vibe coding and agentic coding
Yeah. Um, literally any given person could be 400 of that person like from two years like even like nine months ago. Um, you can be a multiple of yourself.
do you think founders are more ambitious than they've ever been?
They should be. Yes. Um, if anything like that's the number one thing that people should do.
Is realize that like don't chase your success or my success. Like that was, you know, when we were coming up like the game done changed, you know, like you actually you can't just do a SAS thing like you know I was just doing an analysis on like pure SAS and I was like oh shoot like you know a pure like per seat SAS thing like not totally clear it will exist in another five or 10 years like it's perfectly fine as a wedge but if you're doing that now in 2026 like you better hope that that's like a leap to some sort of moat around data or network effects or something else, right? Um, and that's like, you know, if you if we would time travel to like even two years ago, it's like SAS was God, you know, like the 1020x like next 12 months uh revenue multiple was like, you know, iron law.
And like it's hard to believe it was like, oh yeah, no, that's not true at all now.
Well, all this, you know, a related thing that I love is that KOD is no longer precious. Mhm.
My god. Like the things that we had to go through to get something shipped. And that's why you had to have this like sense that what you were making was important with a capital I. And that actually flies against the kind of beautiful truth we were just talking about because often earnestness isn't obviously important with a capital I. So you pursue things that seem important when most of the most important things actually start out seeming actually unimportant.
I know you've been all over this with GStack and GBrain. And you know when you started out to build those things with the intention to like contribute to the community or just explore your interests.
Oh, I was just messing around like you know uh what was it? I think Boris Churnney came on Lite Cone podcast right and I just felt like the urge to you know and a bunch of our mutual friends like all of them uh basically just started coding again and I was like oh something's happening I'd better start. Um and then initially it was just messing around. It's like, oh, I mean, what would it be like to do an like make an office hours?
Um, and then the craziest thing there was like we had just started um like recording all of our office hours actually and then I could I had like a few months of data and there were like very clear things that um the YC partners used as like rhetorical devices or ways to like draw out like a step function in your ambition. Mh. Um, and then what's funny is I have this markdown file that is basically like the perfect script on how to advise founders to like increase their ambition.
And then I actually had to go into Claude and I said reduce this by 90%. Reduce the strength and intensity of this prompt by 90%. And then I open sourced that cuz some of it is like you got to come and do YC 100%.
Of course. Of course. Well, we'll take your five. Okay. Thank you.
Yeah. We can't give away the crown jewels like for free.
This just a taste. The first one's free, you know.
Well, dude, Kevin caught this. I think it was a Gstack or GBrain. We're deep in the open source. You had said, "Please apply to YC."
Yeah. Yeah. Yeah. But only if you're a top 10% user of cloud code.
Like based on whether you're um thinking about users, like thoughtful about your product and your design, like it's not not everyone gets that message actually.
Yes. Yes. Well, dude, I love that you're doing it. And I love that you're doing it so publicly because I think this comes back to the earnestness point which is the whole thing about building intuition at this moment is just using the technology.
You know and I think that there's this feeling like oh how can I possibly catch up or there's so much seriousness around it. It's like no just use every model and build completely trivial things for no other reason to have a chassis with which to learn the new technology. I think the most exciting thing is like you can just have ideas and then in the past it's like oh well I had to be the PM let me write the spec like let me make sure I have you know one or two engineers like oh how are we going to do QA like there's just all this stuff that you used to have to worry about and then now it's like no slash QA like it's done like you know yeah we tested it it's good like we have unit tests like 90% test coverage you know
totally you know it's like arranging your zen rock garden it's just fun to do it and the like the output doesn't matter that much which is why everybody talks about coding agents but very few people are showing their work.
because a lot of it is sort of low stakes work and I think that's beautiful and okay.
No I mean and then I think it's crazy to what degree like suddenly agency and taste like off the charts important now
and then the hard part is like helping people realize like just by the act of doing it and exercising it like that's how you get better. It's I don't actually think that like those things are in innate or inbornne like some people have more of it coming out of the womb per se but
you know it's you just it's like a practice you know
let me challenge you on this because Nikita said this a couple maybe a year ago and I thought it was interesting which is hey we were told that the like highest form of art in business was you know film and software and now anyone can make films and anybody can make software yet the same 20% who were originally doing it are still the ones who are doing it. Is there kind of this like is agency something that you can you know embrace or are there just people that are naturally high agency and many that are not? M I mean if I look at my own career like I would easily say that I'm a late bloomer and you know I had to make these like ridiculous mistakes like saying no to Palunteer or like leaving web programming to like learn and so uh I feel like my life is somewhat like a testament to no no like I can make mistakes and then I can introspect I can reason about them and then make different choices.
Yeah, that is the hope. talk a little bit about loops. I think there are kind of coding loops um which are well discussed and now the graphs thing which is sort of you know both funny and and also real but it feels like the most interesting loops are business loops. Oh yeah like how can you actually have a loop where the output is changing the way the business itself operates. I know there Tom gave this great talk about how to organize your company in that way. Talk about how YC is organizing around loops and how you're advising your companies too.
Yeah, absolutely. I mean I mess around with openclaw. I created Gbrain which is kind of like soda retrieval. Um I basically distill I earlier this year I created giryslist.org which is sort of like actually an agentic newsroom and then I had to create like really really good rag around like you know uh personal deep research just to be able to put together some of those articles. Uh and then all I did was like I had OpenClaw look at that repo extract out like the agentic rag part especially around like um like after the fact uh graph generation um and then it just ended up being soda even against like memory palace and a bunch of other open source uh and then what I realized is that just allows the agent to know what million tokens to keep in its head for any given task.
Yes. And so um what's interesting is like I think there are a couple things at work right now like um the frontier model labs that are you know letting you use chat GPT or claude I think that they're still pretty constrained on cost and pretty constrained on um amount of compute they want to give you. And so if you really want to token max, you actually have to use something like Hermes agent or openclaw.
Um and then you have to like tune it all the way up. Like you're just like give me like let me load a million tokens or 800,000 tokens in to any given request and like have that be in your like soul.md. Yeah, but when you do that, like I think that you basically get to live in uh 2028, like you know, it costs I don't know 50 or $100,000 a year to like use the agents at full strength, like full 150 request. Um but you'll feel it more or less immediately. Uh it just costs like a crazy amount. But um for a CEO or for a founder, uh it actually makes a lot of sense to do that. And you have to give yourself permission to token max in that way. Um but you know and then what you get is like I get you can live in 2028 today.
Amazing. Um, but I think like going back to what founders can do, um, if you live that way, uh, not only do you want to do that task, you want to like skillify it like you you do some like feet of strength and then you turn it into a markdown file plus code plus tests that can be reused and like put into a cron job.
Yes. And so, uh, I think we're just seeing like across the board, um, a markdown file is an employee.
And it's an employee that, uh, will do the job perfectly every single time and it'll do it like as many times as you want.
And then, you know, at that point, all you're doing is like take any business process that you need in your company and you just do it once perfectly. And the first time you try to do it, it's going to be bad.
Expensive. Yes. Many iterations.
Yeah. But then at the end you can you as long as you can tell very very quickly and in very simple ways like hey agent fix this fix that like this was wrong um your the actual trace and the actual uh history out of um that agent uh working with you it'll actually turn that into a skill file that's perfect actually right and anytime it screws up in like a future case is just a bug fix and then it's there forever
and this loop you would apply to sales marketing to customer support to everything.
I mean, GStack was basically that for engineering, right? It's like there's a QA loop. I had to build something that works with browsers to go and because that's what I found like early with GStack. I found myself um you know, automating how I thought about PM and then uh you know, I had an engineering skill that was like an edge manager that made sure that there was uh unit test and end toend test coverage.
Yep. Um, but then in the end I found myself like I automated all the other things so much that all I was doing at the end was blackbox testing to verify. And I was like, oh no, no, okay. Like even that part, like it's interesting like building these agentic systems today. I think that's all you're doing is you're seeing where the bottlenecks are and then, you know, almost every single time it's like how do I just instruct the agent to create a piece of software or a markdown file that blows away that roadblock, right? And then when you take a step back and you've done that for the whole task, it's like, I mean, we—there are companies now today that, you know, we were talking about earlier. It's like literally you can go from zero to 15 mil ARR in about four months with like two or three people and like hundreds of agent—like, you know, a few hundred skill files.
It's amazing. So there's this like recursive self-improvement, there's this hill climbing that happens. Like at what point does it start to fall over? Is there like—do you need error correction? Does the errors compound? Does it get constrained by exception handling, human relationships? Because otherwise these companies should just be able to grow and run forever.
Yeah. I mean, I guess my experience once you get a lot of markdown files or anytime you have like some large amount of data, um, that's where like provenance matters. That's where conflict management sort of, you know, when you have two facts, if you have provenance then you're like, well this is the more recent one, like this is the one that wins. You need a cron job that's sort of sweeping through that and making sure that things are accurate and from the right places. Um, but these are things that I think as you use the systems, um, you just know that you need to build these things. Like anyone who's—I mean, this is actually one of the interesting things I think is an advantage for founders in their 30s and 40s now.
Um, like, I mean, I think that there are going to be as many Patrick Collisons as ever.
Yeah. Um, but one mega trend that we're seeing is like the 35, 40, 45-year-old founder who like been around the block, built a lot of companies.
I mean, I think, yeah, Peter Steinberger is like a perfect example of that where it's like he's been around the block, like he knows what to build.
Um, and then if you take that person, like suddenly there's 400 of those people, like you can outperform an entire department of like any Mag 7. I also think that if you've had some experience in the enterprise, there are these dynamics that, you know, you can seek to kind of mirror and explore. So, one of the things I'm really interested in is conflict, right? Most people at an enterprise would say conflict is a bad thing, but actually think that there's this sort of productive, constructive conflict that at its best is the search for truth.
These systems allow us to do things like explore conflicting approaches and totally unbundle it from the human emotion. And I think that's actually very important because this is why the sort of decentralization in an organization or an economy works well because every idea gets tried, you know.
Yeah. Uh, do you know Pedro from Brex? He's like the most aggressive person I've met who does this with his exec team.
So which is cool. Like he actually was one of the people who like really got me into OpenClaw. Okay.
Um, because he just came in and, you know, he had lunch with us at YC. Yeah. And he just walked us through—you know, the vibe around OpenClaw was that it was too unsafe and dangerous and like delete your whole computer and stuff like that. Uh, what he ended up doing was like building an entire open source layer, which he actually has open source, called Crab Trap.
That is like an agent that watches all the network traffic and all the things that OpenClaw does.
Nice. And then that's how he squares the circle. Like Brex is one of the most regulated, you know, fintech, of course.
Um, and then the upshot of what he got is that he has his agent look at the meeting transcripts from like all of his direct reports and he like can see that like two levels down. And then the thing that really jumped out at me is like he can use, uh, meetings that he's not in to figure out like what's broken, what's in compliance.
