Garry Tan

Garry Tan is the president and CEO of Y Combinator, the startup accelerator behind companies like Airbnb, Reddit, Coinbase, and DoorDash. He previously co-founded the financial technology company Posterous, which was acquired by Twitter in 2012, and later founded the venture capital firm Initialized Capital alongside Alexis Ohanian. Before entering venture capital, Tan worked as an engineer at Palantir Technologies, where he helped develop early infrastructure and design systems. Now, he continues to make investment and product decisions as a General Partner, having read more than 6,000 YC applications, while overseeing programs for sourcing, advising, and scaling early-stage startups. ------ Thank you to the sponsors that fuel our podcast and our team: AG1 https://DrinkAG1.com/tetra ------ LMNT Electrolytes https://DrinkLMNT.com/tetra Use code 'TETRA' ------ Squarespace https://Squarespace.com/tetra Use code 'TETRA' ------ Lectio 365 https://Lectio365.com ------ Sign up to receive Tetragrammaton Transmissions https://www.tetragrammaton.com/join-newsletter

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Rick Rubin?

  Tetragrammaton.

• 0:24Speaker 01

  I love technology and engineering and science because I would just spend every weekend as a kid reading things that were way, way above my pay grade. Like, I didn't understand half of it, but I felt like I could. And it sort of brings us to today, where the machines can help you learn.

• 0:40Rick Rubin?

  Were you a good student in school?

• 0:42Speaker 01

  Yeah, I mean, I didn't realize this at the time. Like, my childhood was so rough that I guess I viewed getting good grades and going to college and...

• 0:52Rick Rubin?

  Your way out.

• 0:53Speaker 01

  That was my... yeah, that was the light at the end of the tunnel. That was always what I thought when I was a teenager. Like, I was suicidal. I hated everything about... But when I was in my computer, I could go in my code cave and I had control. And everything in my life outside of that was tumultuous. And I just didn't know when I would catch a beating for no reason or whatever. But when I was in front of my computer, or even when I was in school studying algebra or calculus, it's like, oh, the world is so beautiful and well arranged, and I can understand it.

• 1:26Rick Rubin?

  Yeah, order.

• 1:27Speaker 01

  Yeah.

• 1:28Rick Rubin?

  When you would be on your dad's computer, would you play games or would you build things?

• 1:33Speaker 01

  I guess games were my first love.

• 1:35Rick Rubin?

  What were the games then?

• 1:36Speaker 01

  Oh, my gosh, like Spy Hunter on the Atari, I guess. But I really loved adventure games, like the Monkey Island games or the Indiana Jones games. The old Sierra adventure games were really fun because I loved... I didn't want just like the arcade. I wanted a story. Like, I loved sort of this idea that you could inhabit another person's life. Today, what people play that I love is like, you know, Red Dead Redemption 2, for instance, one of the best games.

• 2:04Rick Rubin?

  Do you still play games?

• 2:05Speaker 01

  Yeah, I love games. I love those types of games because like the narrative story and you can inhabit someone else's world in reality is... back then, I viewed it as like a nice reprieve.

• 2:15Rick Rubin?

  What is Y Combinator?

• 2:17Speaker 01

  Y Combinator is, at this point, an institution where you apply on the internet and you don't have to know anyone or anything. And you fill out 12 questions, record a one-minute video. And we have 16 partners who read those and watch the video and try to figure out who are the people who are going to build all of the technology for the next 20 years.

• 2:42Rick Rubin?

  How many people try to sign up?

• 2:45Speaker 01

  Yeah, it's 80,000 applications a year for about 800 spots.

• 2:49Rick Rubin?

  Wow.

• 2:49Speaker 01

  Per year. We invite you to come to San Francisco. We'll meet you for 10 minutes. It's usually two partners in there. And 10 minutes goes really fast. It's really, we just want to know, what are you doing? And why is it going to be you who does it?

• 3:06Rick Rubin?

  What are the backgrounds of the two partners in the room?

• 3:09Speaker 01

  Usually, I mean, every partner at YC actually went through the program themselves.

• 3:13Rick Rubin?

  Great.

• 3:14Speaker 01

  And created a startup. And in a lot of ways, they made something people want. So we went and did it. And then we're back trying to help the next generation go do that.

• 3:24Rick Rubin?

  Tell me about your experience of doing it. What do you remember from your 10 minutes?

• 3:28Speaker 01

  Oh, man. I remember sitting down with the founder of YC, Paul Graham, and his other co-founders. They basically wanted to see the demo. And so my startup just, you know, took a photo on an iPhone and emailed it. And then you got a blog. And so that was very easy to demo. And then I think they got it immediately. So once someone understands what something is and why people would use it, that sort of answers the big question. On the first day, YC, you get a T-shirt that says, "Make something people want." And if you look at the 10 minutes, that's all we really care about. It's like, is this person going to make something? And the craziest thing is like, that's easier than ever now. Like, everyone can make something. And then the second part has become much harder, much more important,

• 4:13Speaker 01

  much more difficult to get right, but much more important to get right. It's something people want.

• 4:18Rick Rubin?

  Was Paul Graham the founder of YC?

• 4:21Speaker 01

  Yeah, he was the founder.

• 4:22Rick Rubin?

  Tell me about him.

• 4:23Speaker 01

  Oh, he was sort of this really brilliant polymath. I think you would really dig him. He wrote a book called Hackers and Painters, which is the perfect polymath book. You know, he's a hacker. But at the same time, I saw him recently. He was saying that he built one of the best classical art collections in all of England. He lives in England now. So it's... How cool is that? Like, he literally wrote the book on Lisp. Lisp is one of the most respected sort of hardcore programming language from the 70s. I would say that Lisp is sort of for programming languages, what CBGBs was back in the day.

• 5:01Rick Rubin?

  Cool.

• 5:02Speaker 01

  I mean, it's just anyone who's legit.

• 5:03Rick Rubin?

  Ground zero.

• 5:04Speaker 01

  It's ground zero. It's legit. If you know how to program and care about the code, you know Lisp. And he wrote many books on Lisp, literally called On Lisp. And so we went from there to business, where he said, how do I solve the money problem? You know, he was a PhD at Harvard in computer science. And then afterwards, he said, well, I need to make my way in this world, and I'm not going to get there by painting, but I do know how to program. So how do I turn programming, which is its own craft and art, into commerce?

• 5:36Rick Rubin?

  And when was that?

• 5:37Speaker 01

  I guess it was like early to mid 1990s. So he actually was one of the people who created the first web application.

• 5:44Rick Rubin?

  Wow.

• 5:44Speaker 01

  So the web was new. But then he realized, well, I don't have to just make a static HTML page. I could just hook it up to a program. Today, you think about the web or the internet or a computer program, and it's synonymous with, I open my browser, and I'm going to go to this thing. But he was the first person to actually hook that up.

• 6:04Rick Rubin?

  Do that.

• 6:04Speaker 01

  Yeah.

• 6:05Rick Rubin?

  That's amazing.

• 6:05Speaker 01

  And it was to make what ended up becoming Yahoo Stores. So it was, you know, helping other people build businesses and online businesses. I didn't have the words of, I need to solve the money problem, until I read it in his essays. And I found his essays on the internet. Now, all my friends are sort of in that world. People sort of talk about YC as a little bit of a cult, I guess. But I think about it a lot because, is it a cult? Is it like an ideology? It could be a religion.

• 6:32Rick Rubin?

  It seems productive.

• 6:33Speaker 01

  Yeah. But that's what we're trying to make it.

• 6:36Rick Rubin?

  How is it different than other VC offerings?

• 6:42Speaker 01

  I mean, VC is a very interesting thing because to me, it feels like it's stuck in 1970s or the 80s. VC didn't exist really going back more than 50 years. And then the legends of the space, they're sort of, I felt like they're bankers, you know? They're all dressed up and buttoned up. You ever hear the story of like Fairchild Semiconductor? I think they literally wrote a bunch of letters to a bunch of bankers they knew in New York. And then one of the people who replied was Arthur Rock, who was also the guy who ended up funding Apple later.

• 7:16Rick Rubin?

  Wow.

• 7:16Speaker 01

  And so there's a long lineage of that. But I think it's like really evolved from that. I think today, the best investors in the world are people who are actually former builders instead of bankers. And I think that vibe matters a lot. There's a lot more to the world than just the dollars and cents. Like, the dollars and cents come after you make something people want.

• 7:37Rick Rubin?

  Yeah.

• 7:38Speaker 01

  So I think if I had to describe like, well, you know, is YC just another VC? VC is when it's just about the dollar. I guess the analogy would probably be like public company CEO of a media company, you know? Those people kind of, their job is to only make the dollars go up, and that's it at any cost. Whereas when we're early, we don't have to be like that. And in fact, if you try to do that early, when people don't have an idea yet, you'll kill it.

• 8:06Rick Rubin?

  So how does it work? People answer 12 questions? 1% get invited to a meeting?

• 8:12Speaker 01

  Oh, yeah, about 3% or 4%.

• 8:14Rick Rubin?

  3% or 4% get invited to meet, you meet for 10 minutes?

• 8:16Speaker 01

  Yeah. Yeah, only 1% actually get an offer to be funded by us. And we give them half a million dollars. It is an investment, so we end up owning 7% to 9-ish% of each company.

• 8:29Rick Rubin?

  How much is it about the money versus what else YC does?

• 8:34Speaker 01

  I mean, there are lots of places to get money at this point. What you can't get anywhere else is actually a community of people. And when you're early and you don't know what you're even going to build yet, the best thing you can do is surround yourself with other people who are actually builders, who have been there. And then it needs to be sort of the safe space where you can talk about what you're doing. And we try to enforce that, actually.

• 8:57Rick Rubin?

  Beyond the fact that money is more readily available now than it used to be, is money less important now?

• 9:04Speaker 01

  I think so, actually. The wild thing now is like, the act of being able to do the craft suddenly became...

• 9:11Speaker 01

  A hundred to a thousand times more important. The joke is Thanksgiving of 2025 was this totally insane shift in the way coding and code gen works. So Anthropic released its Opus 4.5 model and the world shook, but no one noticed until they're only starting to notice now. I noticed in January where I started coding again after a hiatus from 2013. And right now I am about to do about 100x the amount of work coding, writing software that people can use. Then the whole year of 2013.

• 9:50Rick Rubin?

  Wow.

• 9:51Speaker 01

  So imagine like if there were 100 people in this room.

• 9:54Rick Rubin?

  Yeah.

• 9:54Speaker 01

  This room would be packed to the gills. Like you probably couldn't fit 100 people in the room that we're sitting in. But that's how it feels when I'm sitting in front of a computer right now. I've released two different open source projects in the last 60 days. One of it, which G stack is actually used by 30,000 people every single day right now. And it's free. I just gave it away. And then 11 days ago, I released another thing called G brain, which is my knowledge memory system.

• 10:22Rick Rubin?

  Explain what it is.

• 10:23Speaker 01

  So there's this crazy thing happening where obviously code gen happens. You can use something like Claude code to write 100 times more software than you did before.

• 10:35Rick Rubin?

  Does the fact that you were an expert coder in the past make a difference or no?

• 10:40Speaker 01

  I think it helps a lot, actually. Claude code was sort of the first revolution from November. And then now there's this new phenomenon that only happens since November, I would say. Where there's this other thing called Open Claw, which OpenAI just bought. And it's an open source package though. So I think they basically just kind of brought the people in. Started by this guy named Peter Steinberger. I mean, it's a social movement at this point. It's actually very anti corporate. It's like the definition of open source from the bottom up. And I'm a total believer in it now. The ridiculous thing is.

• 11:13Speaker 01

  I dressed up in a lobster suit for our podcast, The Light Cone, and the internet didn't seem to like that very much, but I didn't care. But I actually, at that moment, wearing the lobster suit, it was more kind of a joke to me. I didn't really get that there was this new phenomenon called Open Claw. And now I get it. I see the religion. So do you know the movie Her?

• 11:33Rick Rubin?

  Yeah.

• 11:34Speaker 01

  Would you want to own a version of that AI from the movie Her? Where you have control of the AI? Or would you want to use it controlled by the corporations?

• 11:44Rick Rubin?

  Oh, obviously, it's always better to control things yourself.

• 11:47Speaker 01

  So that's why Open Claw is so powerful. I use this example all the time. I mean, do you use an iPhone?

• 11:54Rick Rubin?

  I do.

• 11:54Speaker 01

  Do you use Siri?

• 11:56Rick Rubin?

  I don't.

• 11:56Speaker 01

  No one uses it. And the reason why is it turns out Apple isn't great at doing that stuff. But what if I told you that I'm going to release like an open source version of it? That actually works. And that's what I've basically been working on the last 11 days. Like if this thing, that's what G Brain is. It'll actually connect into your email, contacts, calendar. It read my Apple Notes for like the last 18 years. It read my emails. It went and looked at my calendar for the last 18 years. And then it mapped everything. It looked up all the people I've met. It actually checked up on them and be like, here, this, you know, you met this person a few years ago. This is what they're up to now.

• 12:36Rick Rubin?

  Amazing.

• 12:37Speaker 01

  So imagine this AI. But instead of the AI that some corporation owns and uses it to surveil you, it's like you literally own it. You own the code. You own the data. Nobody else has access to it. And then you can actually tell it to do stuff and you can program it yourself. So, yeah, we're in the middle of-

• 12:57Rick Rubin?

  And you don't need to know how to code to do it, is that correct?

• 13:00Speaker 01

  I mean, I'm trying to figure out how to make it so that anyone can do it. So that's what, that's some of the experiment that I'm in the middle of right now. So I released this 11 days ago. It's got 8,000 stars on GitHub. The analogy we've been using is when the Apple II came out by Apple, the thing that made Apple as a company was, it was actually the first commercial- Usable version that a non-engineer could use of a personal computer. That moment hasn't happened yet for AI. Right now, it's still corporate. It's still very, very expensive. It requires a lot of customization. You have to hire all these engineers to run it for you. And then this maps to how computers were back in the seventies exactly.

• 13:44Speaker 01

  Like, Steve Jobs literally grew up and lived in that moment in age. When him and Steve Wozniak were sitting in a garage in Mountain View creating Apple Computer. They were at this moment where they had to solder a breadboard to create the Apple One.

• 14:00Rick Rubin?

  And before that, it was these giant room-sized computers.

• 14:03Speaker 01

  And nobody could, no normal human being could have one for themselves.

• 14:07Rick Rubin?

  Only institutions and corporations.

• 14:09Speaker 01

  Yeah, so we're exactly at that moment again. And at a much more powerful sort of technology. I think personal computers did revolutionize the world. And then this is like the next revolution. It's happening right now. The Homebrew Computer Club for AI is happening right now. And anyone can actually come in and be a player and a part of this next revolution.

• 14:30Rick Rubin?

  Tell me every tech revolution you've lived through.

• 14:34Speaker 01

  Oh, my God. I mean, well, I was born in 1981, so I guess I was born during the personal computer revolution. My first computer with my dad, because my dad really loved. I mean, in retrospect, I really thank him for being really into that. Because, yeah, it's super lucky.

• 14:50Rick Rubin?

  Worked out.

• 14:51Speaker 01

  Yeah. I remember hearing about Kanye early on, like, managed to get some early audio equipment. And that was actually a part of becoming someone who can make music. So I feel like me getting a PC XT when I was five years old. I didn't learn how to write with a pen until later. I learned how to type. And the first story I ever wrote was, I think, in WordStar 3.3 on a IBM PC XT, which was very funny. But yeah, the personal computer was a really big idea. Before, only digital or IBM or just these giant organizations. Like, your university or a giant corporation you worked at would let you time share. And it was like very, very limited, and it couldn't do a lot of stuff.

• 15:36Speaker 01

  It's kind of funny, because we're sort of exactly in that age with AI.

• 15:40Rick Rubin?

  And you see a time when that will be democratized?

• 15:44Speaker 01

  Yeah, that's the open claw moment. Like, I think that that's happening. That revolution is happening right now. I think a lot of people, a billion people, are using ChatGPT. And the wild thing that I see, that a lot of people in tech are seeing, just beginning to see, I mean, there's probably a thousand of us in the world that really believe this. But everyone is going to run their own AI agent that is totally under their control, that they program.

• 16:10Rick Rubin?

  Will it still be connected to either ChatGPT or Anthropic or not necessarily?

• 16:14Speaker 01

  Not necessarily. For now, I think it will be, but the hope is you'll be able to choose. I think that that's actually going to be one of the big enduring questions in the next few years. There's sort of this nightmare scenario where one company or one entity or just one government has control of the biggest and best and only superintelligence. And I think in that unipolar world, really, really bad things will happen. But the good news right now is it doesn't look like we're on that trajectory yet.

• 16:56Speaker 02

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• 19:10Rick Rubin?

  What are your thoughts on bias in AI?

• 19:14Speaker 01

  This is where control matters a lot, so... And actually, this is a very interesting debate, right? There will be people out there who say, "There should only be one AI, and I want to control it." Right?

• 19:25Rick Rubin?

  There'll always be people like that.

• 19:27Speaker 01

  Yeah, there's sort of like the one-world government people.

• 19:30Rick Rubin?

  Yeah.

• 19:31Speaker 01

  And then there's the sort of renegade people who are like, "No, no, I want to be a pirate. I don't want to join the Navy, I want to be a pirate." And personally, I'm Team Pirate. So I think that personal responsibility, personal liberty, and personal computing, and personal AI.

• 19:46Rick Rubin?

  The idea that the thing that's right for one person is right for everybody else is a crazy idea.

• 19:50Speaker 01

  I definitely don't want to live in that world.

• 19:52Rick Rubin?

  It's a dehumanizing idea.

• 19:53Speaker 01

  Totally. So, and I think we have choices right now, and that's why I think the personal AI movement is really, really important.

• 20:00Rick Rubin?

  Now, there was an open-source AI that came from China maybe a year ago?

• 20:06Speaker 01

  Oh, yeah, yeah, yeah. Those are model companies like DeepSeek or Quen.

• 20:10Rick Rubin?

  How did that change things when they appeared?

• 20:13Speaker 01

  It scared the crap out of everyone and Nvidia's stock went down by 10% and I bought on that day, which was funny. So I think there are two things happening. One is that it's good for the pirates. It's good for Team Liberty because it showed that there can't be just one. There can be many, many model companies out there and that's going to be really important. But the second thing that is scary and maybe bad is that the reason why the Chinese companies are able to do that is they're actually stealing the intelligence right out of the giant American model companies. So two things can be true at once. It can be true that, and ironically,

• 20:57Speaker 01

  you know, Chinese companies that are operating outside of the American and Northern American and European hegemony of copyright law can do this and then they can release it. And then at the same time, they're sort of doing a thing that is not totally clear that should be legal or good.

• 21:15Rick Rubin?

  Aren't all the American companies built on stolen material as well, though?

• 21:19Speaker 01

  Yeah, that's a strong argument. Yeah, I mean, you could say that's fair use and, you know, it's kind of odd for the big model companies to come and say, actually, this is just our copyright.

• 21:29Rick Rubin?

  They didn't write anything. They didn't create anything. They just bunched it up.

• 21:33Speaker 01

  That's right. Yeah, they brought it together.

• 21:35Rick Rubin?

  Aggregated it.

• 21:36Speaker 01

  Yeah. So, and you know, on the one hand, we're all really, really, well, not everyone's glad that they did it. But, you know, I think that it's clear that there is a lot of value to it. It's a really powerful tool. And then that's the debate. As we're sitting here, it gives me pause that Sam Altman had not one, but two different violent incidents at his home in San Francisco.

• 21:57Rick Rubin?

  Tell me about that. I don't know anything about that.

• 21:59Speaker 01

  Someone threw a Molotov cocktail at his house. And then literally the next day, after all of the news media published photos of his house and the address, there was a drive-by shooting.

• 22:10Rick Rubin?

  Wow.

• 22:11Speaker 01

  Yeah. I mean, no one hurt. Obviously, just property damage.

• 22:15Rick Rubin?

  Why does the mainstream media have such a hatred of technology?

• 22:20Speaker 01

  I mean, on the one hand, it sort of makes sense. The mainstream media has really suffered from the death of ads. You can trace it to journalism being actually broken down by, I don't know why people don't give Craigslist a little bit more shit for this, actually. I mean, you can directly trace the decline of ad revenue to newspapers to Craigslist. And on the other hand, I think people are pretty happy that they can go to Craigslist and sell their toaster. And Craigslist is free. So I think there's a lot of paradoxes in how technology comes out into the world right now. And that's a good one. That's what are you supposed to do? Like, were we supposed to protect the newspapers? Were there supposed to be laws that prevented this from happening?

• 23:05Speaker 01

  On the other hand, Craigslist is free and it's giving a service that people are using that is way superior to having to call up the newspaper and pay $20 just to sell your car or something like that. So what should the rules be? Things change, is that okay? And then I always think about, are you familiar with this funny management book? It's Who Moved My Cheese?

• 23:28Rick Rubin?

  No, I know the title, but I haven't read it.

• 23:30Speaker 01

  Yeah, I mean, you don't need to read it because that's basically the whole thing. I think it's just people literally don't want their cheese to be moved. And technology is the primary cheese mover in society. And so it makes sense that people are very upset with tech people.

• 23:44Rick Rubin?

  Is there a world in the future where all pieces of content can be on the blockchain? And then when they're integrated into AI, you know where things are coming from?

• 23:58Speaker 01

  Yeah. Basically, a lot of it is, what are the laws around it? How do we get people paid? What do we do about it? For a while, there's this idea that artists should be paid via things like Patreon, which I actually invested in. I mean, I met Jack Conti and Sam Yam. I think they were actually right out of college. I mean, they were college roommates. And one is a great musician and one is a great computer scientist.

• 24:22Rick Rubin?

  How'd they get the idea for Patreon? Do you know?

• 24:25Speaker 01

  I think Jack had a band called Pomplamoose and he was on YouTube. And he just basically, I think this was about when Kickstarter happened. But Kickstarter had a problem, which is if you're running a band, you're not making products, you're not making one-off things. You don't want to sell a T-shirt, a new T-shirt every week just to make money. So he says, why don't we just do that? How about the straight-up patronage model? Like, I really like this musician, I really like this artist. Let me just pay them $10 a month. So I think Patreon just continues to grow. And that's a great model for sort of squaring the circle.

• 24:56Rick Rubin?

  Do they have competition? Does anyone else do what Patreon does?

• 24:59Speaker 01

  I think they sort of have a good lock of what's going on right now. But Kickstarter still exists, and I think GoFundMe still exists. And there are lots of different things. But Patreon, I think, has just brought together all the people who are super creative, who just want patronage. And my crazy idea for UBI is actually that. Shouldn't we just expand that? There's sort of big, big, deep debate about, what are all the people gonna do when AI comes and takes the jobs? And I guess my answer is, one, I think people are gonna do a lot more cool stuff to serve each other. Not just make something people want, but make a whole lot of stuff that people want. Like, that's, that's sort of my first answer. And then my second answer is the something people want part

• 25:41Speaker 01

  doesn't have to be just more enterprise B2B software. It doesn't have to be that. It could be more music. It could be more art. It could be more fun parties. I was hearing about, was it Ari Emanuel? I heard that he was starting to buy all of these big, like, live event things. That's so brilliant, actually. That's going to where the puck's gonna be. Because suddenly, when everyone has all this free time, they're gonna want to have fun. They're gonna want to go to parties, want to have interesting experiences. They're gonna want to experience being a human more than being a drone worker. Wasn't it Aldous Huxley who talked about, you know, all of this technology will eventually result in a 20-hour work week?

• 26:26Speaker 01

  And it hasn't happened yet, but maybe now. Now is the time.

• 26:30Rick Rubin?

  So after the personal computer revolution, what was the next one that you experienced?

• 26:35Speaker 01

  I think the next one was clearly the internet. I mean, I remember... Like 1996 or so, like I was like a freshman in high school, running around and running Cat 5 networking cable all around my high school on Net Day. Al Gore was running around talking about like the information superhighway is gonna change everything and it did, like he was right, actually. I grew up in Fremont, which was the first place in the entire country to get cable modems. So I could run a Linux box in my bedroom and I did. And I learned how to make websites and program them. And that was super fun, honestly.

• 27:18Speaker 01

  I mean, basically Paul Graham did it the first time and then by the time I did it, it was like maybe 1995, 96 and everyone was starting to do it.

• 27:27Rick Rubin?

  Was it easy for you to get information in those days?

• 27:30Speaker 01

  We still had the Yellow Pages, you know? My funny story is my first job, we were living in apartments and I looked around and I looked at my brother, who was three or four at the time, and I was like, man, I don't want us to grow up in an apartment. The American dream is that we should live in a house, so how do we do that? And then I looked down at my feet and there's a stack of Yellow Pages. My parents are kind of hoarders, so I don't know. There's like a whole bunch of Yellow Pages. I picked up one, I flipped it to the internet section. I learned how to make webpages. The funny thing about the internet is on the internet, nobody knows you're a dog or a 12-year-old. So I won all these like web design awards as a 12 or 13-year-old and then by then, I said, well, if I'm a, that's a pretty good tagline.

• 28:15Speaker 01

  I could just start cold calling people on the internet. And so I found this company called InfoLane. They, funny enough, made city websites and they made like the city of Fremont website and I thought that was cool and I just cold called them and I said, hey, my name's Gary, I'm 14 years old, I'm a award-winning web designer, I'm looking for a job. Are you guys hiring web designers? And so I got that first job, rode my bike about two miles over to InfoLane. This tiny little three-room office. It was, the main tech guy was this guy named Andy McCray, who's like bearded Unix programmer, like just grizzled, really knew his tech, this classic CTO. And then the CEO was this guy named David Hilstrom and he had slicked back hair and

• 29:00Speaker 01

  he had like the finance shirt that had the white collar, but then like the blue stripes underneath.

• 29:07Speaker 01

  And then the pleated khakis and like the suspenders. And he was a fascinating guy, honestly. Like, he taught me the value of look someone in the eye and a strong handshake. And that was some, that wasn't something my dad was gonna teach me because he never learned that. He couldn't figure that part out, you know? So this is really interesting motley crew. At home, everything was a mess. And then I could ride my bike and go to work and hear like quirky, super smart people who weren't yelling at each other, just getting things done and making city websites, you know, like serving the public good. And we were doing it by just typing in front of a computer. And there is a designer I got to work, my first designer I ever got to work with was named Jackie. I feel bad, I don't remember her last name. I feel like I learned everything about design from her.

• 29:52Speaker 01

  She taught me this thing called the squint test.

• 29:54Rick Rubin?

  How much older was she than you?

• 29:56Speaker 01

  I think she was, must have been 55. Like, she was much older.

• 29:59Rick Rubin?

  So she was a grown up and you were 14?

• 30:00Speaker 01

  Yeah, I was 14. She was like, I was just sitting right next to her.

• 30:03Rick Rubin?

  So you consider her like a mentor?

• 30:05Speaker 01

  Oh, absolutely, yeah.

• 30:06Rick Rubin?

  Have you had many?

• 30:06Speaker 01

  I mean, so many mentors. I mean, the universe seems to just unfold and it's like, here's, here's someone you need to learn from. You just have to answer the call, I guess. You just have to be like present.

• 30:17Rick Rubin?

  And what was the next one after the internet?

• 30:19Speaker 01

  Oh, my God, the internet was so big. So the funny, funny thing about me is I learned how to make websites. I cold called to get my first engineering, like learn, my first job where I learned to code was this design firm called Adjacency in San Francisco, run by now my friend Andrew Sather. His story was crazy. He just cold, he didn't cold email because Fortune 500s didn't have email. He would cold send these beautiful graphic design briefs of what the internet could do for these giant brands. And he signed them as an 18 or 20 year old out of University of Wisconsin.

• 30:51Rick Rubin?

  Great idea.

• 30:52Speaker 01

  In 1998.

• 30:53Rick Rubin?

  Just had a vision for what it could be.

• 30:55Speaker 01

  Yeah, so back then, websites didn't look like the way they do now. They looked like dinky, ridiculous, like under construction signs and gray backgrounds. So Andrew Sather figured out how to make full page bleed websites that look like magazines. And that was the thing they figured out, which I love. I mean, I only say this because at every moment in technology, like, there is like a cult of the new that creates value in a way that is astonishing.

• 31:25Rick Rubin?

  Each of these things that you're describing. Changed everything and are all still living now.

• 31:30Speaker 01

  Yeah, I mean, I think about, I mean, sitting here in Shangri-La. This is the place that so many songs were born right now, right? And so whether it's music, or art, or movies, or frankly, code. Code is one of those things, actually. So, and I got to work with these legends who, they came up with it. So Andrew Sather created the first Apple e-commerce store on the internet for Steve Jobs. And so I got to work with that.

• 32:02Rick Rubin?

  What was that store?

• 32:02Speaker 01

  Oh, they sold, you literally just went to apple.com. It was a brand new idea back then to be able to do e-commerce.

• 32:09Rick Rubin?

  Selling Apple devices online?

• 32:11Speaker 01

  Yeah, so you could buy an iMac. And so it was this beautiful, I mean, I thought that was the coolest thing I'd ever seen. Like, Apple was this thing up in the sky.

• 32:18Rick Rubin?

  Yeah.

• 32:19Speaker 01

  They made beautiful products, you know.

• 32:21Rick Rubin?

  And before that, where would you have to go to get one?

• 32:23Speaker 01

  Oh, you'd have to go to an Apple store. Oh, I guess the Apple stores didn't exist yet. Oh, shoot.

• 32:27Rick Rubin?

  It was probably hard to get.

• 32:29Speaker 01

  I don't, yeah, you'd have to go to a retailer.

• 32:32Rick Rubin?

  And I imagine in many places in the country, there wouldn't be a retailer.

• 32:36Speaker 01

  Yeah, that's right. And you couldn't go online to buy it. So it's like, yeah, it's unfathomable that all these things that we take for granted were created by people no different than you or me. I think that's like a straight up Steve Jobs quote. That's what he said.

• 32:50Rick Rubin?

  It's true.

• 32:50Speaker 01

  He said, "Once you realize that, like, you'll never be the same."

• 32:54Rick Rubin?

  Yeah, it's not special people doing these things.

• 32:56Speaker 01

  Yes. I mean, they are special, but everyone's a little bit special.

• 33:00Rick Rubin?

  Exactly.

• 33:01Speaker 01

  Yeah.

• 33:12Speaker 03

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• 34:40Rick Rubin?

  Next revolution.

• 34:41Speaker 01

  Oh my god. So after the internet, a sort of a toss-up between social, I would say Facebook was a big deal for sure, social media, and that happened because of the web. The funny story for me is I learned how to make all these webpages, and then I thought that the web was dead. So it was like, I was 2003, a computer engineering major at Stanford, graduated. No startups, like I couldn't, all the startups were dead in 2003. Web 1.0 had already crashed. It's funny, one of the summers I spent at the man.com. I mean, earlier we were talking about venture capital. In retrospect, that's the kind of venture capital that was bad.

• 35:20Speaker 01

  When you go in and sort of astroturf a business idea with someone who is a suit and not a builder, you get an idea like that. I think it was a men's magazine, some like 20-page PowerPoint about like all buzzwords. It's basically like mediated from a new sphere of people who are just disconnected. Like here's a bunch of abstractions, and if it's hot, if it sounds hot, then I better get ahead of it. But that's like... Trying to navigate while you're blind. And what a builder can do is they know how this stuff is built. They got eyes, they can see. So you can just see like, hey, there's this thing over here. I'm gonna go build that thing. And then they build it and then it's awesome.

• 36:03Rick Rubin?

  So would you say the best VCs today are the ones who are the builders?

• 36:07Speaker 01

  I would say so.

• 36:07Rick Rubin?

  Yeah.

• 36:08Speaker 01

  I mean, that's just sort of necessary, especially early stage. It just doesn't make sense that you could be that good an investor without being a builder first.

• 36:17Rick Rubin?

  How different do the ideas change from an initial pitch until the thing that ends up being successful in the world?

• 36:25Speaker 01

  There's some of a little bit of both. Someone like Tony Hsu from DoorDash, that's what they were and that's what they were always. And then there were like little adjustments along the way. They said, we're gonna be the best food delivery. And then the micro pivot there was like, as everyone else was working on cities, they said, oh, we're gonna do suburbs. And just that little shift allowed them to grow really, really fast and beat everyone else. Sometimes it's like Brian Armstrong at Coinbase. He came in and said, I believe that Bitcoin is going to be really, really big. And then he just worked backwards from that. And so the first version of what he built, I think it was called BitBank. All he was trying to do actually initially was build a Bitcoin client for the phone.

• 37:08Speaker 01

  And then this is like the act of the founder. You know, you're out there, you're trying to make this thing. And then you realize, oh, it's not gonna work. You know, the whole Bitcoin client can't fit on an Android phone. And even if it did, you'd have to sit there, leave it plugged in for five hours a day just to make it usable. I mean, okay, that's not gonna work. Let's turn around and make it work on a server. And then he did that and it again didn't work. And he said, well, why? It's actually really hard to get Bitcoin. I built a thing that holds Bitcoin, but how do you actually get it in there? And then he went and did that and it became Coinbase. So.

• 37:42Rick Rubin?

  Amazing.

• 37:43Speaker 01

  So these things always evolve. They always change. And really great founders seem to be able to just ask the first principles questions and then go after that thing.

• 37:52Rick Rubin?

  Walk me through the 13-week program.

• 37:55Speaker 01

  Oh, yeah. We're in week two right now of the spring batch. Honestly, most of the first 10 weeks is just building. So you come in and.

• 38:08Speaker 01

  This is fresh in my head. We just went through the basics. And it's funny how much you have to do the basics. But we have a bunch of really experienced, successful former founders who are coming back and doing Y C again, alums. And it's funny to watch them have to go back to beginner mind.

• 38:25Rick Rubin?

  So these are people who are going through the program a second time?

• 38:29Speaker 01

  Yeah, totally. So some of our best founders, like Parker Conrad of Rippling, came back through a second time. And increasingly, alums are coming back and doing Y C again.

• 38:39Rick Rubin?

  You think they're doing it for a nostalgic reason? Or because they get something specifically by doing it?

• 38:44Speaker 01

  I mean, I think the Y C batch done right is a little bit more like a revival or an experience than an educational product or something like that. I think it's an experience. And then our reality is constructed entirely with other people. And so the number one value the first few weeks is actually disconnecting from your normal rhythm and saying, OK, I displaced my entire life. I am coming over here. I'm intentionally going to work on this company. And I'm going to create a thing for other people to the exclusion of everything else. And I'm going to focus on just that. And that alone is so valuable.

• 39:29Speaker 01

  Because otherwise, you know, the first thing we say is like, in every other context, your best friend calls you and needs to move and needs your help that weekend. Now you've got an excuse.

• 39:39Rick Rubin?

  Yeah.

• 39:39Speaker 01

  And the answer is, sorry.

• 39:41Rick Rubin?

  It's always tomorrow.

• 39:42Speaker 01

  Yeah. Right now, I'm doing a thing. And so it's kind of funny how much just making intentional space in your life is just that.

• 39:51Rick Rubin?

  Yeah.

• 39:51Speaker 01

  And then doing it in sort of like an encounter session style way. It's like you're with all these other people. And every single week, you see their struggles and what they're going through and the evolution in their thinking. And then about week three or four, it starts becoming, oh, it's working for them. Am I behind?

• 40:10Rick Rubin?

  Would you say it's competitive? Or more like everyone inspires everyone else?

• 40:15Speaker 01

  Ideally, it's the latter. Sometimes it's competitive. What's funny is my Y C batch, we had one of my fraternity brothers from Stanford actually was in my very Y C batch. But our startup idea was post an email and get a blog. Theirs was post an email and get a photo on a photo frame. And so we were competitive with them. Like, I knew that they were gonna launch and we were going to, we needed to launch first. You know, Parker Conrad talks about that during his batch for Zenefits. He was doing health insurance for business. And there was another company called Simply Insured. And boy, did that light a fire under his ass to make that company 10 times faster and better than his competitor.

• 40:53Rick Rubin?

  Yeah.

• 40:54Speaker 01

  So mostly, I wanted to inspire, but on the other hand, a little competition never hurt anyone.

• 40:58Rick Rubin?

  And it sounds like that's like real world direct competition in those cases.

• 41:02Speaker 01

  Oh, yeah.

• 41:03Rick Rubin?

  Which you will have to encounter.

• 41:05Speaker 01

  Yeah, that's super real.

• 41:06Rick Rubin?

  Yeah, it's different than, well, he's building something really different than me, but I want to be as good as him.

• 41:11Speaker 01

  Yeah, that's right. A lot of this is, the 13 weeks is a lot about trying to get people to focus on the thing that really matters. Instead of, how do I raise more money from VCs? How do I impress the finance bro? None of that matters. The only thing matters is, did we make a thing that people want?

• 41:27Rick Rubin?

  Going hard must be much more palatable, knowing in 13 weeks, this is over.

• 41:34Speaker 01

  Yeah, it is a process. I mean, most of the companies, the median company raises $2 to $3 million. On the high end, people raise $10 to $20 million after 13 weeks. So there is, there are real stakes to the competition. And then just running people fast at a particular thing matters a lot. I've never seen anything speed founders up in such a profound way. I spent a couple of years, sort of in my wilderness years. I spent about, funny enough, it was seven years in the wilderness. It sounds ridiculous to call it the wilderness. I started my own VC fund that was very successful, called Initialized. And during that time away from YC, I would try to do pre-seed. I'd meet teams that I really loved and I'd give them half a million dollars.

• 42:17Speaker 01

  And I'd say, go, like, here's all the essays.

• 42:20Rick Rubin?

  Not the same.

• 42:21Speaker 01

  Yeah, and I'd meet them every week. But they're in the coworking space, in the WeWork, and they're, you know, sitting there in the coffee room, like, hanging out the way they used to when they worked at Microsoft or something. And it's like, it's not, you haven't changed anything yet. I imagine it's the same deal with just any creative profession. It's like, just get yourself out of the, out of your head.

• 42:42Rick Rubin?

  Yeah.

• 42:43Speaker 01

  Change your location, change the people you're with, change the way you think about things. And that's my only explanation. Like, I would try to pre-seed people and get them to speed up, to startup speed, and it would never work. And then finally, I'd Get frustrated and say, okay, it's time for you to do YC. And if they were good enough to get into YC, then they would speed up. And suddenly magically, they would turn around and a year or two later, they'd be making $20 million a year in revenue or something.

• 43:08Rick Rubin?

  How did it work out for you to get invited back to run YC?

• 43:12Speaker 01

  Oh, man, that was an intense experience because I was good to go. I had billions of dollars under management and I had built the firm myself. But the founder of YC, Paul Graham, asked me to come back.

• 43:26Rick Rubin?

  Do you know why he picked you?

• 43:28Speaker 01

  Oh, here's a funny story. The story of Paul and Jessica is fascinating because PG, you would dig him so much. He's just connected to the source, man. Everything about YC that he designed has that quality about it. It's thoughtful and not ostentatious and concise and spare. And I guess that's what brought me back. And then I think YC itself way exceeded his expectation for it. I think he's a billionaire many times over from starting YC. And it became sort of clear by, what, 2013 or so that that was true.

• 44:08Rick Rubin?

  How many years had he done it?

• 44:09Speaker 01

  Seven years at that point. So he himself went through a seven year journey, starting and running YC. He had young children and I didn't realize it at the time, but I was working at YC. I was sort of one of the Proges. And then Sam Altman of OpenAI fame was also came up through the first YC batch in 2005. Paul famously wrote an essay about him. He made a list of five top founders of our generation. And he put Sam on that list when he had not created all the things that he's created since yet. So at the time, it was very controversial in our community because Sam.

• 44:46Rick Rubin?

  Clearly, he could see it.

• 44:47Speaker 01

  PG is connected to the source, man.

• 44:48Rick Rubin?

  He called it.

• 44:49Speaker 01

  He called it. In 2013. PG brought me and Sam and my fellow managing partner, Harge Taggert, out to dinner at Fuki Sushi. At the time, he was looking for successor. YC had become so big and so like an institution that it was too much work for him. And he never really intended on that being like the only thing he ever did for the rest of his life.

• 45:15Rick Rubin?

  Yeah.

• 45:15Speaker 01

  Plus, he had young kids. And so he went to each of us in turn and said, who do you think could run YC? Harge and I, I mean, Harge and I come from, I don't know, basically immigrant backgrounds. And for me, I've just been on, I'm a very late bloomer. I feel like I'm still in the process of blooming as it is right now. Like, I'm still discovering who the heck I am and how do I connect with my body.

• 45:40Rick Rubin?

  I hope that never ends because there's something beautiful about that.

• 45:42Speaker 01

  Oh, yeah.

• 45:43Rick Rubin?

  That's a great state to be in.

• 45:44Speaker 01

  That's true. I wish I did it earlier. That's the problem. Like, I would be more, things would be better if, they could always be better. But the point is, you know, Harge and I looked at PG and said, nobody, man, you got to do this forever. And in that dinner, Sam Altman said, I could do it. And he did it. He took it over, which was awesome. I remember Paul.

• 46:06Rick Rubin?

  And how long did he do that for?

• 46:08Speaker 01

  2013 through 2019. And then he basically, that was when OpenAI took a life of its own. And Sam had to choose.

• 46:18Rick Rubin?

  Yeah.

• 46:19Speaker 01

  And honestly, like, as it happened, I have to give it to Sam. I have to, I have to say it. We were rivals. Honestly, sometimes he was kind of a jerk to me, but I realized that was just a part of the thing. That's part of the grand plan and the game, you know? He called it. I remember working for him in 2014, before I had decided to leave. And I said, every meeting, he'd come back and he'd be talking about AGI. Like, he met Elon, he met Larry and Sergey. And the world unfolded to him in a way, like when he became president of YC. I didn't understand it at the time. I'm like, hey, Sam, we're just trying to like, fund some startups over here.

• 47:03Speaker 01

  Like, that's cool, but can we talk about this B2B SaaS thing?

• 47:09Speaker 01

  And then, I hate to say it, but I look at the 2014 version of myself and it's like, "Shoot, man, you were the Salieri and Sam was the Mozart, you know? He was there and he heard it and he saw it and he said, 'That's the future and then we're gonna go get it.'" I have to give it to him. He did it and it was like one of the fundamental lessons for me in my life, I think. I'm trying to like embrace. There was something that blocked me, closed me off to what was clearly going to happen and I was there. So much of tech and so much of my life day to day is improv. It's like a yes and. You're sitting with founders, very creative people and it's like, "Whoa."

• 47:52Speaker 01

  Instead of saying, "No, it's not gonna happen," you know, I should be saying, "Yes, and." It's like, "Oh yeah, how does that, like, how does it happen? And if it happens, what happens?" Right? And it's just funny to think about that 2014 snapshot for me, sitting in the YC partner room with Sam and like all the other partners who were working at YC at the time, under Sam. The vibe was not yes and for Sam. The vibe was like, "Why is this guy doing this?" And so that's actually one of the things that keeps me up. I run YC today and I wanna run that room in a very different way. And I realize sometimes I'm the one who's bringing that "what the heck is going on" energy and my people are thinking that about me. I think YC is very interesting.

• 48:32Rick Rubin?

  It sounds like you might not wanna use him as the example of how to do it.

• 48:36Speaker 01

  Maybe not, yeah. I mean, I think he's learned a lot. I think he's become a different leader. I think that he, he's taking a lot of shit right now and I really feel for him and his family. On the other hand, he doesn't deserve what he's getting right now.

• 48:53Rick Rubin?

  Was it hard to go from a founder to doing something like running YC? Do you miss the day to day of your thing?

• 49:04Speaker 01

  Oh yeah. I get to have my cake and eat it too, at this point. Cause what I'm doing-

• 49:10Rick Rubin?

  Because you're open sourcing things.

• 49:11Speaker 01

  I'm open sourcing it and then honestly, it's turning into the next thing that will bring people in. Like, I found Paul Graham and YC because of Paul Graham's essays. And Paul Graham's essays are still about a third of all of the applications that come in.

• 49:28Rick Rubin?

  When were the essays written?

• 49:30Speaker 01

  I mean, throughout his life, starting, I think, in the late 80s or early 90s.

• 49:36Rick Rubin?

  Tell me about do things that don't scale.

• 49:39Speaker 01

  Oh, yeah. I think a lot of the things that the advice that you hear that we, I mean, some of it is like, we give away all the advice for free. That's been a long debated thing inside of YC. VCs don't do this. VCs like to say that this is a, you know, this is an institution.

• 49:57Rick Rubin?

  Closed ecosystem.

• 49:58Speaker 01

  Yeah. You gotta get our money and the only way we're going to teach you how to do anything is you gotta come through us and they're gatekeepers. And then I really want us to not be like that. And I think YC has never really been like that. You go to any other incubator or even any other VC that does this job and helps founders and you look at their curriculum, it's all our stuff because we give it away on the YouTube channel. There's 2 million subscribers on there. And I think we want to just keep doing that, honestly. We want to just like arm people with the knowledge to go and create this stuff. How cool is that right now?

• 50:32Rick Rubin?

  Amazing.

• 50:33Speaker 01

  The tools are way more powerful now than ever, actually.

• 50:41Speaker 03

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• 52:09Rick Rubin?

  How similar are the pitches that you get each semester? Are there a lot of the same idea?

• 52:16Speaker 01

  Oh, it's tons. And then the first thing we have to do is try to get them on something that's more unique to them.

• 52:21Rick Rubin?

  And do you give feedback?

• 52:23Speaker 01

  Oh, yeah, yeah, yeah. No, I mean, one of the top things that we started doing the last two or three years once I came back is we have to meet people one-on-one. You know, a quarter of my team right now is in India, and they're in New Delhi. These people are cracked, man. They are so smart. They're like 22-year-olds, PhD candidates. And then the most interesting thing, my partner Ankit Gupta just put in Slack that I was just like, that's fascinating. It's like they're just working on 2008 Web 2.0 ideas right now. They're like social networks and tutoring marketplaces, which is very funny because in the history of YC, I feel like that's one of the most common ideas. I think the founder of Dropbox, famously in, what year was it? 2006?

• 53:09Speaker 01

  He was at MIT, and he was working on a tutoring business. And he met Paul and Jessica. And Paul and Jessica said, you're the right person to do a startup, but like you should not work on tutoring, man. And then he ended up coming up with Dropbox. So it's very funny how, same as it ever was, like people are still doing social networks and photo-sharing apps and tutoring businesses, but they shouldn't. They need to work on things that are truly unique to them.

• 53:36Rick Rubin?

  Do you get any really fringe ideas that are unlike everything else?

• 53:40Speaker 01

  Oh, yeah, all the time. The craziest one I really, that's doing well and might actually pull it off, there's a space fusion company.

• 53:48Rick Rubin?

  What does that mean?

• 53:49Speaker 01

  Literally, there are these nuclear scientists at the national laboratories. And they're in their late 30s, early 40s. But they'd been working on fusion at the national labs for years. And they came back with these simulations from their research. Fusion on the planet is very, very expensive due to gravity. But they have a simulation and a design that shows if you're in space, you can do real fusion at a scale that is actually viable. And they're basically, they have to see about it. It's kind of like falling in love. You're like, oh, man, should I change my flight? Or, you know, it's like, this is off my plan, man. Like, this is not what I was trying to do.

• 54:33Speaker 01

  But like, I gotta see about a girl, right? That's what it feels like for some of these founders.

• 54:38Rick Rubin?

  Yeah, that sounds great.

• 54:40Speaker 01

  Yeah, so they're off, they raised, you know, I think four or five million dollars. And these are not normal, beaten path, worked at Google, went to Stanford kind of people. They are actually the smartest possible scientists to do it. And in most cases in the world, like 99 out of 100 universes, those guys don't get to raise $5 million. But because YC exists, those guys are up and running. And if they succeed, we will have fusion in space, which is wild. And I don't know if it'll happen, right? They don't even know if the simulations can actually happen in real life. But we have to see about it.

• 55:18Rick Rubin?

  Yeah, that's exciting.

• 55:18Speaker 01

  We gotta find out.

• 55:20Rick Rubin?

  Are the people who get picked more likely to be the ones who come up with the idea that you've not heard before?

• 55:26Speaker 01

  The idea is a function of the people. In those 10 minutes, if we don't learn anything, then it's probably a no. Really, really smart people, the people you really want, they're really high agency. And then they're also just so perceptive. I guess they're connected to the source. That's probably the hardest thing. It's like, you know it when you see it. Like, you meet someone, it's like, that person is connected to something beyond.

• 55:53Rick Rubin?

  Yeah, they can feel it. It's even beyond thought, it's some other thing.

• 55:57Speaker 01

  Yeah, so when you meet people like that, I mean, when I met Brian Armstrong, I was like, oh, my God, there's something going on with that guy.

• 56:05Rick Rubin?

  Typically, would you say, is it more about the person than the idea?

• 56:11Speaker 01

  I think it's more about the person, yeah. What are they about? You have to be about something. You have to have a thing in you. And I realized, like, actually, I can spot that in other people. You just spend time with people and it's like, man, you got some sort of nuclear reactor in there. Just don't lose containment.

• 56:30Rick Rubin?

  Yeah, let's figure out how to use it for good.

• 56:32Speaker 01

  That's right.

• 56:35Rick Rubin?

  So if a founder gets accepted, what happens next?

• 56:39Speaker 01

  They move to San Francisco. I feel like San Francisco itself is a trip. It's so much more open. The number one thing that people describe when they come from any other place in the world and they come to San Francisco is that they're not weird anymore. If you came to Y C.

• 56:54Rick Rubin?

  They don't feel like outsiders.

• 56:56Speaker 01

  Yeah, they're insiders. Like, suddenly, you're surrounded by people who believe that they can actually poke the universe and have it pop out someplace else. And there's very few places in the world where that really happens. Everywhere else, it's like, tall poppy syndrome. Don't try to do this. Who are you to even believe that you could do this?

• 57:16Rick Rubin?

  What do you think makes Silicon Valley Silicon Valley?

• 57:21Speaker 01

  It's earnest nerds just making a thing that people want. And then.

• 57:26Rick Rubin?

  How did the nerds end up there in the first place?

• 57:31Speaker 01

  I guess you could argue there was like, basically, all the semiconductor people. Basically, it was post-World War II. A lot of research and development happened. Hewlett-Packard started out of Stanford Labs. There's just sort of this long percolating thing where you had the smartest people in the world collect in a particular place to do a particular thing.

• 57:53Rick Rubin?

  Is there a government aspect of it or no?

• 57:55Speaker 01

  Oh, definitely. I mean, the Internet was all defense research. The Internet exists because DARPA gave a grant to experiment with communication systems that are more resilient than telephone if there's nuclear war. So if you needed that, then you needed something like TCP/IP, which is one of the basic protocols that runs the Internet today. And so that's why you had these Unix mainframes at every university. And then they would make these links that were not, you know, normal, pick up the phone and call them, or fax machine and things like that. It was literally, what would you have to design? You'd have to design email.

• 58:35Speaker 01

  And so there is a deep, long history of defense and primary research dollars going into fund technology that then gets commercialized and then it becomes the thing that everyone uses.

• 58:48Rick Rubin?

  If there was going to be a second Silicon Valley somewhere else in the world, where do you think that would be?

• 58:54Speaker 01

  I think New York City right now. The reason why we tell everyone to be in San Francisco is the rate of and likelihood of someone creating a company worth a billion dollars or more is 2.5x higher if they move to the San Francisco Bay area, and then it's about 2x higher if they're in New York City.

• 59:12Rick Rubin?

  Tell me about the personality of the founders. Is there anything that you see that runs through many of them?

• 59:20Speaker 01

  I mean, the two traits that I really love to see, one is earnestness, which is very unusual as a trait. This definitely comes from Jessica Livingston in particular. There's this idea that the best founders are sort of hucksters, and I would say 90% of the people that really, really make it are not that. They're actually very earnest about what they're trying to do. And this is in contrast to like cynical or like a snake oil salesman. We're always sort of fighting this war where there are always founders who sort of take it too far. There are always founders who do things that they shouldn't do. I guess the funniest thing to say would be the really, really good ones know how

• 1:00:05Speaker 01

  far to take it and not farther. And we just fund so many founders, period, that the ones that don't make it, a lot of times, they don't make it because they went too far. And I'm still trying to figure out what to do about that, actually. Because if you come down too hard, you're going to lose all the weirdos. But on the other hand, like clearly, you need to have some sort of consequence. And so we're trying to figure it out. YC is always growing, like we seem to be growing like 100 or 20%.

• 1:00:34Rick Rubin?

  What do you mean like too far?

• 1:00:36Speaker 01

  And just straight up doing things that are legal or unethical. The hard part here is like the tournaments, every market is so crowded. But I think they're all open again. So there's this sort of interesting time in startups where, going back to the waves, you have, anytime there's a new wave, we have this idea that it's a blue ocean. You could just do anything, literally anything, and it'd be awesome. Like, if you did a social network in 2004 or 2005 and you were good, you could have killed Facebook. Like, any of those things could have happened. And then as time goes on, usually like five or 10 years in, the companies raise hundreds to billions of dollars, the revenue goes up.

• 1:01:20Speaker 01

  It goes from a blue ocean to a red ocean. Basically, it's a blue ocean when nobody knows which end is up, and there's no competition. And then anything that could be really, really big ends up becoming a red ocean. And that became more and more true over the last 15 years. And then AI has basically opened it up and everything's blue again.

• 1:01:40Rick Rubin?

  It seems like it might be for a long time, no?

• 1:01:43Speaker 01

  We'll see. I mean, hard to see even beyond next year. I think a lot of it depends on how much smarter the models get and at what rate. I don't like to be someone who wants technology to slow down. But right now, at the current rate, I feel good. It's like, it's progressing at a pretty fast clip, but it's not like mind-blowingly so fast that like, you know, startups can't exist or business can't exist. In fact, it's progressing slower than most AI researchers would say it should. I was sitting with Bob McGrew, who is chief research officer at OpenAI, old friend of mine. And one of the first things he said when they came up with O1 and the reasoning models was like, they released it to the world,

• 1:02:28Speaker 01

  and it's like, nothing happened. And they thought, oh, well, we built it. Like, they should all come right now. I was like, no, no, no. Like, that happened like maybe a year, year and a half ago. We're only now actually bringing it to the business world. Like, only now is it actually having an impact. So.

• 1:02:47Speaker 01

  I mean, that's one of the lessons for founders. Even if you can be right, even if you created the thing that a billion people is, they're going to use it and it's going to change their lives completely. Like, you literally invented the wheel. You could invent the wheel and you still gotta jam it down people's throats, man. It's like, they're not, they're not gonna come willingly.

• 1:03:07Rick Rubin?

  People don't know they want the wheel if they don't have the wheel.

• 1:03:09Speaker 01

  Exactly.

• 1:03:10Rick Rubin?

  Yeah.

• 1:03:11Speaker 01

  So that's where it's like, oh, this is good news, actually. Like, someone invented the wheel, you know, someone invented the personal computer. But then...

• 1:03:18Rick Rubin?

  Now what?

• 1:03:19Speaker 01

  Yeah, you get to build it. You get to bring it to people and you get to be a part of that grand play. All the world is a stage and at this point, you know, all the world is just being vibe-coded.

• 1:03:30Rick Rubin?

  Would you say most of the founders are building something personal or building something for a general problem?

• 1:03:41Speaker 01

  It always starts personal. That's sort of the do things that don't scale, right?

• 1:03:45Rick Rubin?

  Yeah.

• 1:03:45Speaker 01

  Basically, a lot of the advice comes from, we just see people fail over and over again. And then we just sort of write down the notes. It's like, oh, yeah, just don't do that. Like, the reason why YC can be so helpful is there's about a thousand ways that startups fail and we've seen all of them and we can graph them on a mean distribution. We just keep people from doing that. And then there's this classic line from Paul Graham, which has become more and more true, which is, as long as you don't die, you will succeed.

• 1:04:17Speaker 01

  Like, it might take five years, it might take 10 years, you know? Like, if you are just in there thinking about things, if you do good reps, you're gonna be in the right place at the right time.

• 1:04:25Rick Rubin?

  It's just a matter of time.

• 1:04:26Speaker 01

  Yeah.

• 1:04:27Rick Rubin?

  What happens at the end of the 13 weeks?

• 1:04:30Speaker 01

  So that's sort of when you go off and show the world what you got and you see whether the investors wanna bite. And we have about a billion and a half dollars of investors per year who come and they're investing, on average...

• 1:04:47Speaker 01

  I mean, anywhere from a million and a half dollars to four, five million dollars. On the high end, like 20 million dollars into any given company. I think the median has doubled since I came back to Y C. It used to be about a million dollars raised a demo day. Now it's closer to 2.2 million per batch.

• 1:05:04Rick Rubin?

  How important is the ability to pitch?

• 1:05:07Speaker 01

  Oh, it's super important. And then the funniest thing now, though, is we used to spend so much time on that part. I mean, this is one of the subtle, interesting things. I think that A I is becoming so good. We have these scripts that

• 1:05:22Rick Rubin?

  coaches people up?

• 1:05:23Speaker 01

  Literally, I mean, that's slash office hours, but for everything else. This is actually a very interesting model that I think is going to happen across all of society, where we always think about code. All the businesses in the world right now think about like, oh, I need to build software. And that's like deterministic ones and zeros. And what no one has figured out yet is that like, it's not just the code. It's also the skills. So the newest thing that's happening now is that the thing that used to be ineffable, the thing that I had to sit with someone and teach them this stuff.

• 1:05:59Speaker 01

  Now that I say it, it sounds kind of scary and crazy, but I think it's becoming true that I can actually distill down what I know and what we've learned from like thousands and thousands of founders. Our ability to do it is a thousand times better now because we actually can literally use Circleback or Granola and record our office hours. And we're doing it in the short term, just tactically. So it's like, oh yeah, this is what we talked about and this is what we should do.

• 1:06:29Rick Rubin?

  Explain what Granola is.

• 1:06:30Speaker 01

  Yeah. Circleback or Granola are these meeting recording agents. I mean, there's a bunch out there. You can even go on Chat G P T, apparently, and click the microphone button and it'll just start recording and listen to your conversation and it'll summarize what you talked about. But the really crazy thing is that you can take that and you can take that plus all the other ones you did and you can diarize it, meaning like you have an L L M go line by line and say, instead of the full text, it's like for every 10 or 20 minutes, it's like, this is what they talked about and this is what was interesting. And then you can take that and have another thing, another L L M come and summarize all of it and then distill it into principles and like the things that you would put in a book.

• 1:07:13Speaker 01

  The intelligence is already there and it's able to do that.

• 1:07:17Rick Rubin?

  Do you think there's an issue with the ability to summarize? Where, think of the difference between reading a great piece of literature or the Cliff Notes.

• 1:07:27Speaker 01

  Yes.

• 1:07:27Rick Rubin?

  They're two different things.

• 1:07:28Speaker 01

  Oh, there's definitely a difference. Yes.

• 1:07:30Rick Rubin?

  Do we lose something in the summarization economy that we now live in?

• 1:07:36Speaker 01

  I think the experience that we're hoping for with YC partners is actually the feeling that you should get is that like, I don't get Groundhog Day anymore. And that's starting to be what we see at YC. So before, I had to be in every single conversation, per se, and like, teach them the basics, one, two, three, four. Now, instead, it's better. Because if I have our bookface agent, we have like our own AI agent that helps, is starting to teach people these more basic things. Then, when I see them, I actually know where someone is. And then, we're talking about stuff that's quote unquote, "out of distribution." We're always thinking in AI, in terms of like, what's already in the model and what's already on the internet.

• 1:08:17Rick Rubin?

  Yes.

• 1:08:18Speaker 01

  Versus what is new, that has never been before? And then, all the alpha and all the things that are interesting, the things that make you alive, the things that connect you to the source, it's not in like, playing the hits.

• 1:08:31Rick Rubin?

  Yeah.

• 1:08:31Speaker 01

  I can play the hits all day. And like, last year, that's what my day to day was like. That's what every partner was like every single day. It was like, oh yeah, here's the two-sentence pitch. This is what the two-sentence pitch is.

• 1:08:42Rick Rubin?

  Now, that stuff's all covered.

• 1:08:44Speaker 01

  We can just spend all our time on like, the new new.

• 1:08:46Rick Rubin?

  Yeah.

• 1:08:46Speaker 01

  And like-

• 1:08:47Rick Rubin?

  And the specifics for each case.

• 1:08:48Speaker 01

  Yeah. So that's really important. And so that's like, sort of the thing that people should be really excited about. When we talk about how do we let society do more interesting things? I think we can embody it. It's like, in your body, do you feel more excited to come to work and why? And for me, that answer is like, when I get to talk to new people about new things, instead of talking about the same people to the same things. Right? And so, that's where AI is super good news for people who are super creative and highly agentic. Like, if you have agency, you can design your day to be exactly like that. And then, the second thing that I think is really important that we learned at YC is, you have to write the prompts.

• 1:09:31Speaker 01

  So we almost did this to ourselves where we use AI to like pick people and we always, we have for like many, many years, but the old AI. And then the old AI was not smart. It was, we call it feature-based. It was literally just matrix math. It was before the transformer. It was before all of the crazy stuff that happened. And that stuff was so dumb that it required like an incredible amount of data labeling. And then what we found was the 15 partners started becoming data labelers under the API. There's this very crazy idea that kind of Venkatesh Rao talks about. He's this internet thinker that talked about all of the world is being recreated into

• 1:10:14Speaker 01

  these like Uber or DoorDash sort of API lines. With AI, the danger is like everyone in the organization is either like above the API line or below it. You want to be above it.

• 1:10:27Rick Rubin?

  Yeah.

• 1:10:28Speaker 01

  And then the ideal to me is as many people in the org as possible are above the API line. And what that concretely means is actually from my partner Pete Cooman, who figured out, actually, we need to allow every person to own their own and change their own prompt. So when you use Google, for instance, and they have their AI product in your Gmail, it's kind of dumb and doesn't really do what you want. Well, that's because some Google engineer and PM.

• 1:10:57Rick Rubin?

  Note the prompt.

• 1:10:58Speaker 01

  Who didn't live your life, who doesn't know anything about you and the things you care about, and they don't let you change it, right? And so that's like a basic product problem. Like when you use, this is the problem with closed source. This is a problem with corporate AI. Is it like all of it is hidden away and this stuff is so powerful. This is the, this is why OpenClaw is blowing my mind and it's so powerful. It's so obviously the future.

• 1:11:24Rick Rubin?

  If you build something great in open source, isn't it possible over time that it grows into a business?

• 1:11:33Speaker 01

  Oh, yeah. And YC has funded some of the biggest open source wins. Superbase, for instance. I use it all the time. And that started as an open source project. And then usually you make money on hosting. And they're going to be one of the biggest. I think someday they might be bigger than AWS, personally.

• 1:11:49Rick Rubin?

  Wow. They're in the same business as AWS?

• 1:11:51Speaker 01

  Yeah, they help people store their data.

• 1:11:53Rick Rubin?

  Cool.

• 1:11:54Speaker 01

  And so now they're about to go hyperbolic because suddenly everyone and their mama is going to have their own personal G-brain or they're going to have their own personal agent. And that agent has to store its data someplace. And it's probably going to be Superbase. And that started as an open source project that did not necessarily have any intention of being commercial. And then it just turned out to be this huge thing. And it doesn't have to be like that. A lot of people like in open source are like Linus Torvalds from Linux. And that's also awesome. Like, that guy walks on water. And, you know, I think every person on the planet owes Linus Torvalds like an incredible thank you for what he created.

• 1:12:35Rick Rubin?

  How did social media change the world?

• 1:12:38Speaker 01

  I think that the black pill on social media is that it's somehow like destroying democracy or changing the way, in a bad way, like how people are thinking. But I don't believe that. I really think that people believe all the things that you see on social media before. It's just that you would never see it before. The result, though, is that you have to have a lot more cognitive armor around yourself and what you allow in. And I'm trying to teach that to my six and 10-year-old right now.

• 1:13:10Rick Rubin?

  Is it working?

• 1:13:11Speaker 01

  I don't know. I hope so. They're really addicted to YouTube. I feel terrible that that's true. But I'm sure a lot of parents are struggling with that.

• 1:13:18Rick Rubin?

  There's so much great stuff on YouTube, though. I mean, you can learn anything on YouTube.

• 1:13:22Speaker 01

  And so that's what I'm trying to teach them around social media. And I think they're starting to get it. My 10-year-old, my six-year-old does not get it yet. My 10-year-old, I think, is starting to get it. That like, look, everyone in the world has to stop. Solve the money problem for themselves. And sometimes they have to go and make this YouTube content. And sometimes they are doing it in a way that informs you and helps you and teaches you something and is fun and interesting. And so those things are cool. Watch those shows. But then there are all these other people who they're trying to solve their money problem, but like in a way that hurts you or is lying to you or is just telling you what you want to hear, but is not actually, you know, something that's going to help you. And the defining thing about social media

• 1:14:06Speaker 01

  is that you have to be able to know the difference between those two things. And if I could snap my fingers and teach, you know, the children of the entire world one thing, it'd probably be that. You know, like, how do you tell the difference between something that is genuinely good for you and something that isn't?

• 1:14:23Rick Rubin?

  I wonder if you could have your AI agent organize that, organize YouTube accordingly.

• 1:14:28Speaker 01

  I will add that to my list of open source.

• 1:14:29Rick Rubin?

  That'd be a good one, right?

• 1:14:30Speaker 01

  Yeah, for sure.

• 1:14:30Rick Rubin?

  If you do do that, please send it to me.

• 1:14:32Speaker 01

  Absolutely.

• 1:14:32Rick Rubin?

  Because I'd like to watch that as well.

• 1:14:33Speaker 01

  It's actually been a startup that we've been trying to fund at Y Combinator too. So we'll fund it.

• 1:14:40Speaker 01

  Yeah, social media is so powerful and it's scary. Again, it's like the ultimate cheese mover.

• 1:14:45Rick Rubin?

  How did it impact your life?

• 1:14:48Speaker 01

  I mean, now I have like 750,000 followers on X and it feels like this giant swinging hammer. And then once in a while, it's really, really terrible. But most of the time, it's quite awesome. I feel really thankful that the startup world has let me basically shill all the things that I really care about and believe in. And I think that's unusual, actually. But I guess it's sort of a covenant. Like, anything that I shill is not just shill for shill's sake. It's actually, I'm trying to hold myself to that standard that I'm trying to teach my kids to, which is like, okay, everything I post.

• 1:15:19Rick Rubin?

  You want to turn people on to stuff that you like.

• 1:15:21Speaker 01

  Yeah.

• 1:15:21Rick Rubin?

  Improves your life.

• 1:15:22Speaker 01

  If it improves my life, I want them to have it.

• 1:15:25Rick Rubin?

  How has AI already changed the world?

• 1:15:29Speaker 01

  I think it's 1% of the way into changing the world right now. I mean, you have a billion people using it, so that's pretty wild. On the other hand, maybe 1% of those people have actually really touched the new type of AI that I was talking about in November of last year, mainly because it's so expensive. But the good news is it's gonna get cheaper. You know, spending time with AI researchers, the thing that really jumps out at me is to what degree the future is already here, it's just not evenly distributed yet. You know, William Gibson said that from a Neuromancer. That's where we're living in right now. The models that are, you know, cost $200 a month right now

• 1:16:11Speaker 01

  are smarter than 99% of human beings. And I think less than 1% of that billion people have like really touched it or experienced it. I think that that's something we probably need to work on. I realize now that 16 or 14-year-old version of me needs to have access to that model today. You know, the sort of vibe coding and all the open source that I've been doing, it actually does cost a lot. I think there is a tweet from both Marc Andreessen and Elon Musk about this. Like, the people who are way out on the edge, like my friends, and you have Peter Steinberger, creator of OpenClaw. The reason why he was able to do that was he was so successful in his career

• 1:16:55Speaker 01

  that he could just spend a million dollars a year on tokens and not feel it, and it'd be okay. But like, how many people in the world could really do that? Like, really not very many people.

• 1:17:04Rick Rubin?

  Is there not an open source way to do it now that would be cheaper?

• 1:17:08Speaker 01

  It's almost there, but honestly, it's still expensive. It's still expensive, you know?

• 1:17:13Rick Rubin?

  So are we talking about years away or months away?

• 1:17:16Speaker 01

  I think it's years away still. Like, what you can do today, spending a million dollars a year on tokens, at that point, you're talking about doing the work of like 100 people. And so this would normally cost you, like, a million dollars as a multiplier to like hundreds of millions of dollars in software value, right? Or billions even. And that's happening for, I don't know, 1,000 people on the planet right now. And then the good news from the AI researchers is that it turns out, like, these much smaller, cheaper models, they can be a lot smarter. And I think that's where open source comes into play. That's how that's going to happen. Yeah, there's sort of this difficult interplay right now where a lot of lawyers in America want to say we should ban Chinese models.

• 1:17:59Speaker 01

  And then the awkward thing about that is that will actually play exactly into this other, like, there's only one player in the entire world that has access to the best models in the world, and that would be quite disastrous.

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• 1:19:01Speaker 04

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• 1:20:32Rick Rubin?

  For some of the YC success stories, how far out did some of the ideas sound when pitched?

• 1:20:40Speaker 01

  Bitcoin, I think Coinbase clearly was. I mean, DoorDash seemed kind of crazy. Airbnb was probably the most famous one. Brian Chesky is on my board now. When he came to do his YC interview, Paul Graham said, like, what? People are going to stay in each other's homes? Who does this? Who would do this?

• 1:20:59Rick Rubin?

  Yeah.

• 1:21:00Speaker 01

  And we don't think about that so much anymore. We just say, oh, that's an Airbnb. My favorite story about Brian Chesky is when they started, it wasn't called Airbnb. It was called Airbed and Breakfast. And it was literally an airbed, and they had to provide breakfast. And at some point, when it was starting to take off, someone came in and said, well, I don't have an airbed, but could I do a real bed? And he said, well, we are airbed and breakfast. What if you buy an airbed and put it on top of the bed?

• 1:21:30Rick Rubin?

  So fun.

• 1:21:31Speaker 01

  And then at some point, it was like, oh, no, no, no. Yeah, it's just, yeah, go for it. Just do it. And that turned out to be the much bigger market.

• 1:21:37Rick Rubin?

  Are you ever surprised by what the YC founders can accomplish?

• 1:21:42Speaker 01

  All the time. It's wild. I mean, it just happens all the time.

• 1:21:47Rick Rubin?

  It must be a great feeling.

• 1:21:50Speaker 01

  I mean, there's no feeling like it to sit down with someone and they're like, I have this vision, I have a belief in how the world should work. And then you look down and it happens.

• 1:22:02Rick Rubin?

  Did you change anything when you took over?

• 1:22:05Speaker 01

  The biggest change was that I turned it back into not a VC, but actually focused on the initial early startup founder program. So when I came in, YC had sort of gone from as if Google became Alphabet. When you do a Googled Alphabet moment, it's like, oh yeah, we're doing like eight different things. And we have eight different CEOs all working on different things. And you had something that was very successful that was the engine of it.

• 1:22:32Rick Rubin?

  Yeah.

• 1:22:32Speaker 01

  And I just had to come back and say, we're actually going to focus on the one thing that made YC great.

• 1:22:38Rick Rubin?

  Yeah.

• 1:22:39Speaker 01

  And that's going to be the engine.

• 1:22:40Rick Rubin?

  And that no one else is doing, really.

• 1:22:42Speaker 01

  There are other VCs, there are people who can do your series A or B.

• 1:22:45Rick Rubin?

  Yeah.

• 1:22:46Speaker 01

  You've just got to focus. Focus is saying no. And that was hard.

• 1:22:51Rick Rubin?

  How do you see it evolving over time?

• 1:22:54Speaker 01

  Right now, I'm just trying to see through the next year or two. I think of that meme on the internet where everyone in the world is dancing. And then there's this one lonely person in the corner and they're alone.

• 1:23:09Speaker 01

  And it's like, AI is changing everything. And then everyone's dancing, everyone's just doing their thing like they don't know. I think it's called literally the they don't know meme.

• 1:23:19Speaker 01

  Right now, we're just trying to figure out, how do we change ourselves? We always built software to make YC awesome. That when Paul Graham first started taking applications, he famously made his own software. You would go on the website and he made his own web app that would allow them to review thousands of applications. And Now we're sort of in that next moment, going back to this AI tutor that will teach you how to vibe code. What if it also helped us figure out and identify the people who should get million-dollar token grants?

• 1:23:53Rick Rubin?

  That'd be great.

• 1:23:54Speaker 01

  I mean, that's what we're asking all the time. Basically, we're here to try to help the people who are like us from when we were 18 to 30 or whatever, just earlier in our careers. How do we actually find those people and help them? And what would that look like today? And that's currently the plan. It's like, OK, well, everything just changed. And everyone who could be a founder, well, they don't need to raise like a billion dollars anymore to build their dream. Like, there are companies right now that have 10 or 20 people making hundreds of millions of dollars a year and soon to be billions. And that looks radically different than some of the wins that I talked to you about, right? They don't, to a T, like, if you look at the list

• 1:24:37Speaker 01

  of 100 unicorn companies that YC has funded since 2005, there's something about getting to scale and having customers that forces you to have thousands and thousands of employees.

• 1:24:48Rick Rubin?

  Until now.

• 1:24:49Speaker 01

  Yeah. And then the thing is, some of those are really, really inefficient. Going back to like the Siri or even Meta Glasses analogy, you look at those organizations and they have like tens of thousands of people. It's like, why? And those people are really smart. Are they actually applying their brains and horsepower to like things that are real? Or are they going to have like really nice sashimi at lunch? And it's sort of adult daycare. And that's not bad. I mean, honestly, these are amazing jobs. I have a lot of friends who are in those orgs, and those are incredible jobs. But I also look at what they could be doing

• 1:25:32Speaker 01

  and what society like desperately needs human beings to do, which is to be even more in service to one another. How does that happen? How do we make that happen? And my fear is that society, built as it is, locks people away into default paths. Like, just become a management consultant. Go get your MBA. This is safe. You'll get your pension. You'll have your nice vacations. Drive your BMW. There's nothing wrong with that. And that's a great life. And I want more people to have that. But on the other hand.

• 1:26:07Rick Rubin?

  There's so much more.

• 1:26:08Speaker 01

  God gave you this brain. And God gave you these senses. And we can do so much. And how do we do more? Like, how do we serve each other more? Surely, technology is not a bad thing in that. It is a way to solve more problems for one another. And so I am like, super pro technology and super pro markets. Because that's how I sort of square the circle.

• 1:26:33Rick Rubin?

  Tell me about your relationship to machines.

• 1:26:36Speaker 01

  I love machines. I guess my ideology is that it does seem like humans came out of the bush. The reason why we get to sit here and sit in a beautiful place and talk about ideas instead of subsistence farming someplace is actually technology. It's fire. It's the wheel. And it's the personal computer. And then the internet. You know, like, this is sort of the unbroken chain. And it's not just machines. Would you call a book a machine? It's a tool.

• 1:27:10Rick Rubin?

  It's a technology.

• 1:27:11Speaker 01

  Yeah, it's a technology. There was this very influential documentary I saw on PBS called "The Machine That Changed the World." It's like 1995 WGBH, Boston documentary about the personal computer. And in it, it talks about, that's what the computer is. It's an infinite book. But prehistory is before we can write stuff down. And it's lost, it's lost to the sands of time. Like, we have no understanding of how people lived and what people did and what they cared about until we invented papyrus and writing and the book. And then it accelerated with movable type, accelerated with Gutenberg.

• 1:27:52Speaker 01

  And so literacy went from like a tiny priesthood to suddenly everyone could do it. And that's the thing that recurs every single moment. That's what the personal computer was. And then that's what the iPhone and the mobile revolution. We didn't get to talk about that yet. It's like, social media happened.

• 1:28:08Rick Rubin?

  Yeah.

• 1:28:08Speaker 01

  But then, you know, what's funny is Facebook almost died because it almost missed mobile. Instagram happened and Facebook had to buy Instagram because Instagram would have killed Facebook. Instead of Zuckerberg.

• 1:28:19Rick Rubin?

  Facebook was a desktop application originally.

• 1:28:22Speaker 01

  Yeah, it looked like bank software, you know?

• 1:28:24Rick Rubin?

  Yeah.

• 1:28:25Speaker 01

  And Kevin Systrom could have been Zuckerberg, but he sold too early, which is kind of crazy. That's sort of the history repeating itself. The internet computer, it's the paperback computer, suddenly the internet-connected computer, suddenly the iPhone, and then now AI, like the intelligent computer. It's accelerating, it's happening faster and faster. And I think that that's awesome. Like, I guess my personal story is that technology gave me everything that I have. And now I want everyone to have that.

• 1:28:59Rick Rubin?

  Yeah.

• 1:29:00Speaker 01

  And for me, it's like you had to join a priesthood, right? You had to study algebra, you had to get straight A's, you had to get into Stanford. And I did anyway, like, that was like my light at the end of the tunnel.

• 1:29:10Rick Rubin?

  Yeah.

• 1:29:10Speaker 01

  But like, my kids, like, I want them to do that, but I want them, not because I want them to go into the top college, it's because I want them to love the knowledge itself, right? And like, where we're going, I don't know if we're gonna need college, per se. That was the old, post-industrial, like, sort of 20th century version of everything. Like, here's your lane, and like, go down this path, and like, don't ask questions.

• 1:29:34Rick Rubin?

  It feels like those lanes have broken down.

• 1:29:36Speaker 01

  Yeah, but we have to come up with a new path.

• 1:29:40Rick Rubin?

  Would you say you're an optimist in general?

• 1:29:43Speaker 01

  I think I have to be, yeah. I'm a techno-optimist. I definitely believe that technology can and should serve other people.

• 1:29:51Rick Rubin?

  Yeah.

• 1:29:51Speaker 01

  And then where it doesn't, it's really not a technology problem, it's probably a broken markets problem.

• 1:30:00Speaker 01

  Literally, why can't I have good Siri? It's because Apple won't allow a market to exist there. And we spend a lot of time in DC and in Sacramento right now trying to fight for that. Like, we need people to be able to start new things. And then any of the seams that are broken are obvious. It's like Siri is a perfect example. It's like, the smartest AI has been around since November of last year. And Siri could be that smart. But is it that smart? It is not. And why? There's no market. Like, nobody created open access. And so we're using the most beautiful devices in the world. And they're horribly crippled. And they're broken in a way that it should not be broken.

• 1:30:43Rick Rubin?

  Tell me about big tech versus small tech.

• 1:30:46Speaker 01

  Yeah, little tech. I think basically Siri, in a nutshell, is exactly that. Like, we funded a company called Beeper. My former YC partner, Eric Minjakovski, started that. It had a very simple vision, that you should be able to have a single messaging service that is a superset of all of them. So iMessage and WhatsApp and Signal, like-

• 1:31:07Rick Rubin?

  Great idea.

• 1:31:08Speaker 01

  Why do we have like five or six different apps? Like, we should have one app. But he ran headlong into, there's no market for it. Apple says no, and Meta says no. And why? For the good of the company, not for the good of the people.

• 1:31:24Rick Rubin?

  It sounds like a good open source thing to make.

• 1:31:26Speaker 01

  Yeah, totally. The thing is, like, you can't even make it an open source. Because even if it were open source, if you're using Apple, you have to jailbreak it, right? And is that legal? I think the DMCA actually has jailbreak rules that do say that you're allowed to do it if it's on your own device, but they make it intentionally hard. So as a result, the best technology that we could have, we do not have. For what reason? For profits by big tech. And I think, like, at the margins right now, it doesn't matter. But like- When you're talking about AGI and ASI, like superintelligence is here, I think it starts to matter a lot. There's a really big debate happening in startups right now that I think is very interesting,

• 1:32:10Speaker 01

  and I hope we have an answer for it. And that is the OpenAI's and the Anthropics and the Googles and Deep Minds of the world. They have the world's smartest frontier AI. And then the big debate is, are they going to be open ongoing as these models get smarter and smarter? It is possible for the access to the models to close. And then, once that happens, what does it mean? Does it mean that I have to choose? I'm an anthropic person. Do we end up having these vertical walled gardens? I mean, that's sort of what we have now. It'll just be a lot worse. Like, today, you have a green bubble, blue bubble. But why do we have that? It's just so that Apple has more profits?

• 1:32:54Speaker 01

  Again, it's sort of like the builder ethos versus the pointy-headed manager, finance bro ethos. It's like, hey, these are two different things. And like, we're pro-builder. And if the builder wins, it means the best technology gets in the hands of people faster. And it also means little tech can thrive.

• 1:33:13Rick Rubin?

  How different are the AI models today?

• 1:33:16Speaker 01

  They have very different personalities.

• 1:33:19Rick Rubin?

  Would you use one for a particular job and a different one for a different job?

• 1:33:22Speaker 01

  Definitely, yeah. Claude Opus 4.6 is ADHD CEO. So he's really fun, like million miles per second ideas, really gets you, like really vibes with you. And then, he actually like talks out both sides of his mouth sometimes. And, you know, he hallucinates and then can't keep track of like really detailed things sometimes. But that's because his mind is going a mile a minute. And then Codex from OpenAI is sort of like the almost non-verbal 200 IQ savant. And so you're not going to get what it's trying to say. It doesn't really understand you either, but it's a machine intelligence that is raw smarts.

• 1:34:05Speaker 01

  And so, one of the things that I use is, I mainly talk to Claude. And I use Claude code, but then in my GStack skill, I can go slash Codex. And then it sends it off to Codex, my 200 IQ friend. And when I have a problem or it gets stumped or Claude just can't figure it out, it calls in its 200 IQ autistic buddy. And so, yeah, in a nutshell, Claude is ADHD and Codex is autism. And every, every one of these models has like a very different personality. Like DeepSeek, I've discovered is the conspiracy theorist. It's like you give it something, it's like, hey, did you notice this thing? It's like fascinating.

• 1:34:47Rick Rubin?

  That sounds really fun.

• 1:34:48Speaker 01

  Yeah, it's really fun. I mean, everyone has a very different personality and that's a good thing. Like, I think having multiple models, it's sort of like iron sharpens iron.

• 1:34:57Rick Rubin?

  Yeah.

• 1:34:58Speaker 01

  So I want as much diversity there as possible.

• 1:35:00Rick Rubin?

  And Grok started much later than the others. Is it able to catch up?

• 1:35:03Speaker 01

  I hope so. I mean, I want more competition, but a lot of the people who built it have left. So, you know, I want it to win. Like, I want as many options as possible and Elon has all the GPUs. And so, you know, the interesting thing is, you know, can he retain the people? And the thing is like, there's always more smart people out there who could come and make that work. So, I mean, I'm rooting for them. I, you know, the surprising thing is like, you know, the APIs, like they don't push the APIs very much. I think they're just like trying to speedrun their way to ASI directly. I guess you'll see that also with their robots, like they're sort of vertically integrated

• 1:35:44Speaker 01

  and probably as advanced as anyone, but, you know, we haven't seen the usage yet. So, I mean, I guess that's the grand experiment, like never bet against Elon. And the SpaceX IPO is going to be pretty fantastic and epic for all of tech.

• 1:35:59Rick Rubin?

  Should every company go public?

• 1:36:03Speaker 01

  I feel like that's the personal question of for the founders and the shareholders. I guess what I'm seeing, though, is if you have built something valuable, there's a lot of secondary, like people will just come and buy it. And the difference between public and private is pretty subtle. If anything, I think that normal people should be able to buy private shares. That would probably open things up quite a bit.

• 1:36:24Rick Rubin?

  Is that possible?

• 1:36:25Speaker 01

  It's kind of hard. You have to go to things like Forge Global or Angel List or all these different ways to buy private stock. It's kind of hairy.

• 1:36:34Rick Rubin?

  Sounds like a good idea, though.

• 1:36:35Speaker 01

  Yeah, a lot of people are doing it, and then more people probably should get access. I mean, our family recently bought a little bit of Anthropic on secondary. And then the joke among very smart people is great. If you bought a little bit of secondary in Anthropic, it means you get to get upgraded to the level two breadline with the other Anthropic directors. You know, going from level three to level two is a big deal in the future AGI world.

• 1:37:02Rick Rubin?

  Does Big Tech do everything they can to prevent little tech from existing?

• 1:37:09Speaker 01

  I don't think it's personal. I think capitalism means that you're supposed to go out and fight really hard. But at the same time, I'm not free market maximalist in that, like, I'm not a libertarian. Like, I think that there are roles and responsibilities for government to play when there aren't open markets and open access and just to give people choice, right? Like, you know, it's totally great that Anthropic, for instance, has the best model right now, and I love it, and I'm a big fan. And a couple of the YC alums are actually co-founders of Anthropic. But at the same time, it's like, I kind of wish that they would be less anti-competitive, for instance.

• 1:37:51Speaker 01

  Like, if open code, which is an open source code harness, like, I love Claude Code, but also I want open code to be successful and to be able to be used. I think those are big questions, right? When you talk to a lot of the Anthropic folks, like, a lot of them are ex-Google. You know, Google famously stopped being sort of "don't be evil." You know, at some point, they started saying like, "Hey, we're kind of a business and we kind of need to make money," which is fine. Like, I don't begrudge that either. But that's where, like, I do think that there's a role for government to play a guard dog or watchdog. I mean-- If you just let companies do whatever they're gonna do, like, they're not immoral, but they're also not moral. They're amoral. And then the will of the people comes through the government.

• 1:38:36Speaker 01

  And that's why I'm like, people should vote. And we need a healthy media. We need healthy journalism.

• 1:38:42Rick Rubin?

  Just not monopolistic.

• 1:38:44Speaker 01

  Yeah. Yeah, I mean, we should be anti-monopoly. Like, I think monopolies are bad.

• 1:38:49Rick Rubin?

  What is zero-based accounting?

• 1:38:52Speaker 01

  In the context of--

• 1:38:54Rick Rubin?

  YC.

• 1:38:54Speaker 01

  YC.

• 1:38:57Speaker 01

  I guess my first day coming back as CEO, the board met, and it was Paul Graham and Jessica Livingston and Brian Chesky and Carolyn Malavy. That's sort of the board of YC and me. And the number one directive I got was like, what does YC 3.0 look like? YC 1.0 was under PG. YC 2.0 was in Sam era. And then YC 3.0. Let's do zero-based accounting. Like, let's figure out if we were everything that we do, would we choose to do it again today from zero? And so that's what we did. And I think every organization probably needs, you know, especially at sort of a leadership change like that, it's worth doing. You know, if we're gonna change, we need to change as much as we can right now.

• 1:39:39Rick Rubin?

  Not just rest on the laurels of what happened in the past.

• 1:39:41Speaker 01

  Yeah.

• 1:39:42Rick Rubin?

  Like a restart.

• 1:39:43Speaker 01

  Oh, yeah. How do you refound the company?

• 1:39:45Rick Rubin?

  That sounds great.

• 1:39:46Speaker 01

  It was fun. I mean, it's been fun.

• 1:39:47Rick Rubin?

  It sounds like a fun mission for you.

• 1:39:49Speaker 01

  It was insane to see, because, I mean, this thing changed my life. And then now we're rocking and rolling. Like, we're ready to meet this AI thing head on.

• 1:39:58Rick Rubin?

  How important is it to know the history of the category that you're going into when you're starting a new company?

• 1:40:06Speaker 01

  If I go by the Airbnb example, maybe not so important. But as you're in it, you have to learn everything about it. In fact, there's an essay about it called Schlep blindness. If the founders of Stripe knew how much work and how terrible it would be--

• 1:40:22Rick Rubin?

  They wouldn't have done it.

• 1:40:22Speaker 01

  They wouldn't have started. So, and that's probably true for a lot of creative endeavor. Like, almost anyone, if they knew that they had to go through this shit and you spent too much time thinking about the shit, you'd probably just choose to do something else. And I honestly like starting a company isn't for everyone. Maybe that's probably the biggest myth to dispel that should everyone start a company? Honestly, like that's like asking like, should everyone become a musician? Should everyone become X, Y, or Z? And the answer is no, there's no one size fits all profession for someone. Yeah. And then some of them are so hard, like founder, that you better know that that's the only thing you could do.

• 1:41:04Speaker 01

  Otherwise you'll go crazy because on every other day, you're going to say, you know what? This is too hard and I'm out.

• 1:41:10Rick Rubin?

  How much has vibe coding changed things?

• 1:41:13Speaker 01

  I think we're just starting to see it. The wildest thing right now, though, is to what degree people have not changed their view. Like I'm taking a lot of attacks from really smart people, like really smart systems engineers who are really well respected. And then what's funny about it is some of them attack me by name and then I go and look at their open source projects. And I don't see any movement. They're progressing at the same pace that they were progressing a year ago, two years ago, five years ago.

• 1:41:44Rick Rubin?

  Yeah.

• 1:41:45Speaker 01

  And after I get some launches done, I think I'm going to go into those open source projects and I'm just going to drop some PRs on them. In programmer terms, like I'm just going to give them a free gift of like tens of thousands of lines of fixes to like their software. And I think I should actually just give them a gift and then see if they understand and accept it. And if they don't, that's okay. The engineers who hate vibe coding and AI the most are the people who would benefit the most from embracing it.

• 1:42:16Rick Rubin?

  Has anything come through YC that is hardware based as opposed to software based?

• 1:42:20Speaker 01

  Oh, a ton. Yeah. I mean, Stoke Space, for instance, is probably going to be alongside SpaceX with one of the reusable rocket technologies soon. You know, Astronis is actually a competitor to SpaceX, which is fun. Like they're providing internet access. I think many Southwest flights now have internet from Astronis. They're a competitor to Starlink.

• 1:42:41Rick Rubin?

  Starlink.

• 1:42:41Speaker 01

  Yeah. So yeah, what's funny about it is I both respect the heck out of Elon Musk. He came to speak at startup school last year and that was awesome. I also think that we need 100 of those guys or gals. I mean, I think that we need

• 1:42:55Rick Rubin?

  Absolutely.

• 1:42:55Speaker 01

  hundreds of people who get back in the saddle and then try to solve the biggest, hairiest problems for humanity. And we need a lot more of it. And so if I look back on this age of Y C, that's probably the big hairy audacious goal for us. How do we not just create new software businesses that solve the money problem for people? How do we actually literally create new global companies?

• 1:43:22Rick Rubin?

  And make cool stuff.

• 1:43:22Speaker 01

  That make the coolest things in the world, right? Some of it is like actually about giving really great engineers a lane to do their best work. Like, I think a lot of people don't want to work on bank software. A lot of people don't want to help people click on ads. A lot of people don't want to be lawyers. A lot of people want to do something that's really, really meaningful. And then I think our organization needs to figure out, how do we help them do that?

• 1:43:45Rick Rubin?

  Yeah, there is something different about a physical object that you can circle and that you can touch with your hands. That's just different than a great app.

• 1:43:54Speaker 01

  Oh, yeah. And we're coming into that. The interesting thing is, a lot of the reason why it's hard to do that is actually not enough A I and not enough software. So it's sort of fractal. I mean, Palmer Lucky from Android talks about this.

• 1:44:07Rick Rubin?

  And I imagine 3D printing is going to help as well.

• 1:44:10Speaker 01

  Oh, yeah, definitely. So I think we want to accelerate all of the things.

• 1:44:14Rick Rubin?

  Yeah.

• 1:44:14Speaker 01

  I mean, the next thing is pretty clear. It's going to be robotics. And then we need to build stuff again. You know, we have a company called Knox Metals that is helping American companies get access to metal instead of like having to pick up the phone, for instance.

• 1:44:28Rick Rubin?

  What does get access to metal mean? I don't know what that means.

• 1:44:30Speaker 01

  Oh, literally, like, if you need a giant roll of aluminum, how are you going to get it today? You still have to pick up the phone and then you get gouged and things like that. We need a whole American supply chain.

• 1:44:41Rick Rubin?

  Like an ecosystem for supply chain.

• 1:44:43Speaker 01

  Oh, yeah.

• 1:44:44Rick Rubin?

  That's cool.

• 1:44:45Speaker 01

  Yeah, it's interesting because we're playing a role in that. This is where government and regulation actually has a big role to play. Knox Metals is a marketplace for giant rolls of aluminum or whatever kind of metal you want to buy.

• 1:44:56Rick Rubin?

  Yeah.

• 1:44:57Speaker 01

  But there's a cabal. There is like a small set and oligopoly of brokers for that type of stuff. And they started freezing Knox Metal out. And then this is where like social media is interesting. This isn't a bad thing. This is speaking truth to power. That founder went to Twitter, started posting about it. And then through our connections, Luther Lowe is our head of policy. We have a full-time person in DC. And he knows Gail Slater, who's sort of the part of the anti-trust watchdogs of DC. And all she had to do was take that post and post an emoji. And then, you know what? All of the anti-competitive monopoly stuff went away for Knox Metals, literally overnight.

• 1:45:42Speaker 01

  So it's funny, people in tech are afraid of government. People are worried about its impact. But it's like, government is something that can be used for good fundamentally.

• 1:45:53Rick Rubin?

  It would be incredible if it was the case.

• 1:45:54Speaker 01

  Yeah. It's about access, right? Like if you can access them and help them and be in the conversation, that's what we're learning. Growing up, my dad was always like, man, you got to stay away from politics. But that's what, that was the vibe from like Asia, you know, from the 20th century. Like that was what my parents were. My grandfather, for instance, he ran silk factories in Yunnan in southern part of China. And then they were seized by, and the family had to flee. Eight brothers and sisters had to flee to Burma. And my grandfather rebuilt that business in Burma. And then it was seized again by the military.

• 1:46:30Rick Rubin?

  Wow.

• 1:46:31Speaker 01

  And my grandfather died in Burma, but all eight brothers and sisters made it to Canada and the US as immigrants. And so there's a long history of like, America is the place where people who want to create and build come here. Like immigration is a part of this story and it's a beautiful one. And we got to preserve that. And we also have to preserve the ability for people to create new businesses in America. And for that, we actually also have to preserve the idea that starting a business is not bad or evil, but noble.

• 1:47:06Rick Rubin?

  If you were 16 years old today, would you still go to Stanford for computer science? Or would you vibe code your first company?

• 1:47:17Speaker 01

  Oh, man, I'd probably try to go to Stanford at least for a couple of years. And honestly, I don't know. I think I might want to just do Stanford, man. Like, I think that's actually the hard question.

• 1:47:26Rick Rubin?

  It was a great experience?

• 1:47:27Speaker 01

  It was a great experience. And when I was 18, my childhood was so difficult that I felt like I was 14 in college. My whole 20s were sort of this delayed adolescence. And I had to figure out who I was. Yeah, it's funny, at YC, there's this vibe that YC only wants to fund the like 18-year-old or 20-year-old sort of Patrick Collison types. I just don't think that's true. That's not true for me, anyway. Like, I started my company at 27. I just wasn't ready. I was a late bloomer and I just wasn't fully developed. My YC startup was called Posturus, and it actually became a top 200 website. You send an email to our email address, and we would make a blog for you. And it was the fastest, easiest way

• 1:48:11Speaker 01

  to get a photo off of your iPhone, which sounds crazy now, but basically...

• 1:48:17Rick Rubin?

  But you couldn't do it back then?

• 1:48:18Speaker 01

  Yeah, you couldn't do that.

• 1:48:18Rick Rubin?

  Yeah.

• 1:48:19Speaker 01

  And what that space became was Instagram. So everyone uses Instagram now. So in a way, like, in technology, there's a tournament happening all the time. And the winner, it's sort of like Glengarry Glen Ross. First place is you win. Second place is a box of steak knives. And third is you're fired. It's like, that's basically how the competition of technology sort of works. We got the box of steak knives and sold that company to Twitter for $20 million, which is very powerful and meaningful for me.

• 1:48:51Rick Rubin?

  Yeah.

• 1:48:51Speaker 01

  But when I look at what happened there, it's like, I needed to be who I am now in order to properly win that tournament. And when I really look at it, I hadn't done 10 years of therapy yet. And that's what I actually needed to be able to work through all of the things that caused my startup to fail. I ended up falling out with my co-founder. The startup started failing the day Instagram launched, actually, which we should have paid attention to.

• 1:49:20Rick Rubin?

  Yeah.

• 1:49:21Speaker 01

  And then I just wasn't developed as a full human being to be able to go to my co-founder and say what was going on for me. I just ate it. He had a really strong idea for what he wanted to do. And I was like, I had read some like advice on the internet about if you want your startup to succeed, you better be a really good co-founder, you're a co-founder. And I read that and I thought like, oh, that means that I should self-abandon. That I should just do whatever he says, right? I was like, no, are you serious? Like, I was 30 at the time and I wish that I could go back and like shake the me of that time, but I just wasn't ready. Like, there are all these unexamined demons from my childhood.

• 1:50:04Speaker 01

  You know, I sometimes wonder if I'm making the same mistake too. I might be, just by coding all the time right now. Back then, I was like the hero engineer. Like, I just wrote all the code, I did all the design, I even like kept the servers up, which was very inadvisable. And then now, after a lot of therapy, I realized, oh, that's my hero complex. You know, I had to carry my family. My parents were my parents, but like I had to sort of parent them as well. And that's what caused me to be the way I am. But also, it caused me to fail. It caused me to not be able to manage people, not be able to transition, not be able to make the decisions to help my startup. My YC startup in 2008 had a shot.

• 1:50:49Speaker 01

  We could have been a contender. And I think a lot about that. You know, if you don't know who you are, or you haven't worked through the things that are really going on inside of you, or how you make decisions, if you're not an integrated person, this stuff all comes out again.

• 1:51:04Rick Rubin?

  I'll just argue the other side of that. Sometimes the people who are fully integrated can't go to the inhuman, unrealistic extremes necessary to break through.

• 1:51:15Speaker 01

  Yeah.

• 1:51:15Rick Rubin?

  Like, sometimes it's because of that damage that you can just keep hammering.

• 1:51:22Speaker 01

  Yes.

• 1:51:23Rick Rubin?

  I'm not suggesting that as a choice, but it's just the reality that sometimes it takes that.

• 1:51:29Speaker 01

  Yeah, I haven't reconciled that yet. I mean, that's definitely true. Like, when we meet people and they're all the way turned on, it's like, that's coming from someplace.

• 1:51:37Rick Rubin?

  It's not always a positive place, but that might be the energy to get over the gap. And then, once it works, then they can work on themselves and have time. During the race, you can't focus on anything but the race.

• 1:51:50Speaker 01

  Mm hmm. You're hitting on something very deep, and I'm just gonna be super vulnerable here. Like, that's actually one of the defining things I'm struggling with right now. Like, I have a rage and a fire inside me. And I see it. In my therapy sessions, actually, I go visit that room.

• 1:52:08Rick Rubin?

  Yeah.

• 1:52:08Speaker 01

  Like, I can visit my seven-year-old version of myself in that apartment with, filled with beer cans and technical books. And it's tiny, and it's a hoarder space. And like, I slept on the floor, you know? Like, we didn't have beds. Like, we had foam pads on the floor. And I can go there anytime. And I can feel the dread of my alcoholic father is gonna come home. And I don't know who's gonna come home. Is he gonna be drunk already? Is he gonna beat me? Like, what's going to happen? But that's also, when people look at me on the internet, and they're like, what is wrong with that guy? It's like, what's going on for that guy, you know? Or like, they see me with like, the very extreme intensity

• 1:52:53Speaker 01

  of what I want and what I'm trying to make happen. It's because I can go into that room. And I go to my seven-year-old version of myself, and he's in there all the time. And then, I bring in a cup, and it's like this radioactive cup. And he just pours out like, liquid plutonium. And then I go into my day, and I got it.

• 1:53:12Rick Rubin?

  Yeah. Would you say you have a relationship with him where he's not running the show all the time?

• 1:53:19Speaker 01

  I mean, if anything, like, I'm running the show and I'm using him.

• 1:53:24Rick Rubin?

  That sounds like a healthy relationship.

• 1:53:25Speaker 01

  I hope so.

• 1:53:26Rick Rubin?

  That could be your superpower.

• 1:53:28Speaker 01

  What do you think? Do you think so? I mean, my therapist is like, man, you gotta, you need to integrate that kid and like, hug him. And then I'm afraid, well, if I do that, will I be able to still do what I do? I don't know yet. I don't know what the answer is.

• 1:53:41Rick Rubin?

  Do you feel like he's in any way getting in your way now?

• 1:53:47Speaker 01

  Yeah, all the time.

• 1:53:48Rick Rubin?

  Would you say there's a part of you that's self-destructive?

• 1:53:52Speaker 01

  Well, I stopped drinking, so that's good.

• 1:53:54Rick Rubin?

  That sounds great.

• 1:53:56Speaker 01

  Funny enough, I do have a self-destructive streak that I am now very, very aware of. But when I was younger, I was like, oh, no, I'm fine. I'm normal. Everything's fine. I have this like very extreme control thing. It's either self-abandonment or it's domination, right? And the integration thing right now is, how do I, you know, stay in the middle? My wife always says, like, Gary, you're so extreme. Like, it doesn't have to be a pound of broccoli or a pound of steak. Sometimes we just want to eat chicken. And I'm trying, I'm trying, you know?

• 1:54:28Rick Rubin?

  I wonder, just hearing you say it, as long as it's not self-destructive, like you use the word "normal," it's like, normal is nothing to aspire to.

• 1:54:37Speaker 01

  Yeah, that's the median.

• 1:54:40Rick Rubin?

  Normal is average.

• 1:54:41Speaker 01

  Yeah, yeah. We want to be extraordinary.

• 1:54:44Rick Rubin?

  Yeah, and sometimes part of that is a fire that comes from somewhere. As long as it's not burning you.

• 1:54:51Speaker 01

  Yeah.

• 1:54:51Rick Rubin?

  Or burning the people around you and doing good in the world. Having the fire to use for good is really good.

• 1:54:59Speaker 01

  Yeah, totally.

• 1:55:03Speaker 01

  I guess where it's coming up for me right now, I mean, we're gonna get super personal, but I think that it's something that a lot of people who I hang out with actually struggle with, and they'd never talk about it. So maybe we need to normalize talking about it. This cup of plutonium has a deleterious effect, and that is not being able to show up or turn off at home. And so, you know, I've got boys at home. I have, my wife is incredible, and she's supported me all the way through this. And I was just working with my personal AI, doing a bunch of research about Warren Buffett, who at 47 got divorced, famously, I guess. His first wife, Susie, moved to San Francisco.

• 1:55:47Speaker 01

  And at the time, Warren talked about, Susie's amazing, but she doesn't understand the value of compounding. And then years later, I mean, I think recently, maybe like, you know, 30 years after, they didn't get divorced, like, it just was a separation.

• 1:56:04Speaker 01

  But you know, in his seventies or eighties, he started talking about like that was the greatest mistake of my life.

• 1:56:08Rick Rubin?

  Yeah.

• 1:56:09Speaker 01

  So I'm forty five, I just turned forty five. And I guess that's where my head goes. It's like, I'm not that unique. I am.

• 1:56:18Rick Rubin?

  But is it twenty four seven always?

• 1:56:20Speaker 01

  Yes.

• 1:56:20Rick Rubin?

  Or is it twenty four seven always? So you would say.

• 1:56:23Speaker 01

  I'm trying to stop.

• 1:56:24Rick Rubin?

  Okay.

• 1:56:24Speaker 01

  I'm trying to make that space, but I find it incredibly hard.

• 1:56:28Rick Rubin?

  I understand.

• 1:56:28Speaker 01

  I'm Christian, so I don't really believe this. But like, if there was reincarnation, I would have lived ten billion lifetimes to inhabit this body and this mind on this earth at this moment. There's like a sense of mission. I see like everything sort of arrayed out. And there are things that I need to get done that like, if I don't do them, I'm not sure if they're going to get done.

• 1:56:53Rick Rubin?

  Yeah.

• 1:56:55Speaker 01

  How do you sit with that? And how do you go home and basically take the fire suit off at the doorway?

• 1:57:03Rick Rubin?

  Yeah.

• 1:57:03Speaker 01

  And then go home and have dinner with your wife and kids?

• 1:57:05Rick Rubin?

  Yeah.

• 1:57:06Speaker 01

  I think that's what people actually need and want now more than ever, which is just actually connection with other people. And that's sort of what I think society sort of needs. Like in San Francisco, we've been working on this thing called Act Seventeen, where we're trying to bring more tech people into church, which sounds sort of almost antithetical to tech. There is actually a really strong atheist sort of culture around tech, which I think I get. And I was an atheist. When I was growing up, I was an atheist.

• 1:57:34Rick Rubin?

  Yeah.

• 1:57:35Speaker 01

  Because I looked at what I experienced as a child. And I just didn't believe that basically God is supposed to be all seeing, all knowing and all powerful. And I looked at how I was growing up and was like, one of these things is wrong.

• 1:57:51Rick Rubin?

  Tell me something you believe now that you didn't believe when you were young.

• 1:57:56Speaker 01

  The biggest one, I think, is that when I was 22 or so, friends of mine were starting a company and they said, Gary, you're at Microsoft. You're the smartest engineer we know. We're starting this company. You gotta come and quit your job. And I was like, man, I don't know, man. Whatever you guys are doing, like, I got a job. Okay, it was so hard to get this job. Like, what are you guys doing? They finally convinced me to fly down to San Francisco from Seattle and I had dinner with their benefactor, turned out to be Peter Thiel. It was probably within a few months of him writing the $500,000 check to Facebook. And so it's me, my two buddies, Joe Lonsdale and Stefan Cohen, and Peter Thiel. And Peter is like, what are you doing at Microsoft, man? You gotta quit your job.

• 1:58:40Speaker 01

  I didn't realize this was like a whole shtick that you have to do as an investor or as a co-founder is like, you're always convincing people to quit their stupid jobs to come work for you. Right? And so this was just like one of like a thousand conversations that he had. But my buddies really wanted me, I guess. So they put him up to saying, I know you never had money, having a job. And I was like, hey, I have health insurance. He's like, I know all that's really important. How about this? Let's make this a zero risk opportunity for you. Here's a check for $70,000 from my personal bank account. You cash it and this is zero risk. Just quit your job. And I should have waited until after the soup course because I said, no, thank you very much, Mr. Thiel. I might make it to level 60 next year.

• 1:59:25Speaker 01

  I thought I was gonna get promoted and I did get promoted. But that company turned out to be Palantir and I turned down something like, I don't know, $2.5 to $4 billion.

• 1:59:33Rick Rubin?

  Crazy.

• 1:59:34Speaker 01

  Don't feel bad for me. I mean, it was fine. And I also ended up joining as employee number 10. But I think a lot about like that particular moment where I was like, I didn't believe in myself. I didn't believe that my skills were valuable. I thought that like having a job at Microsoft was like a gift.

• 1:59:52Rick Rubin?

  Yeah.

• 1:59:53Speaker 01

  It was not just safe. It was like, oh my God, this is a gift. Like, society has given me a job. I have a vocation. All your power and agency is sapped away inside these like giant organizations. It's safe, but you're like losing something really, really big. And then the other thing, the bigger thing, I think, was realizing I also didn't know how to value what was in front of me. These were my best friends who I'd built products together with. I knew them. They were some of the smartest people I'd ever met. And it was backed by someone who, you know, he's not like, he wasn't a billionaire yet. He had sold PayPal. He was sort of this super famous, successful founder. But everything was perfect. And I said, no. And I asked like, why?

• 2:00:37Speaker 01

  And it's because like, my whole life and everything I believed was constructed for me by people who, now I realize, why was I paying attention to the reporters at the Wall Street Journal at that moment? It's like, they are closer to the source, but they're not connected to the source. People who are like you or Paul Graham or like a lot of the people we know, they are in the flow. And like, the thing that you read about from media is actually the second and third-hand retellings of stuff that the people connected to the source are doing from six or nine months ago.

• 2:01:14Rick Rubin?

  Yeah.

• 2:01:15Speaker 01

  And so I thought, oh, well, they're working on enterprise software. That's not hot. I mean, this whole idea of investing or spending your life following what is hot is like, I'm sure, I mean, this must like drive you crazy.

• 2:01:29Rick Rubin?

  I don't participate in that.

• 2:01:30Speaker 01

  Yeah, exactly. Right? Like, if you met someone and they're like, well, I kind of want to, you know, make something. I want to make a song that's kind of like whatever they just heard. I was like.

• 2:01:38Rick Rubin?

  Who cares?

• 2:01:39Speaker 01

  Dude, why are you like, that's telling someone else's story.

• 2:01:42Rick Rubin?

  Exactly.

• 2:01:43Speaker 01

  You know, what's your story? What's going on for you? And so if I could just go back to when I was 22 and value myself more, and then also realize the whole world is made up and you don't have to take it on authority from media or really anyone, even your mentors, right? Like slay your mentors, not literally, but just like, I mean, in your mind, right?

• 2:02:05Rick Rubin?

  No, they mean well, but they're sharing their experience from their life.

• 2:02:11Speaker 01

  Yeah.

• 2:02:12Rick Rubin?

  And you're on a different path. You're not on the same path as them.

• 2:02:15Speaker 01

  Actually, I love it when I'm mentoring someone or like, I don't feel like I'm mentoring. I'm just literally just vibing with people in office hours. And I love it when I'm like, hey, this is like what I see. And they're like, no, no, no, you have it wrong. And I'm like, oh shit, you're getting connected to the source.

• 2:02:31Rick Rubin?

  Yeah.

• 2:02:31Speaker 01

  I want to actively find people who are like, they're making their own connections and they're like building their own world models of how the world works.

• 2:02:40Rick Rubin?

  It's the best.

• 2:02:40Speaker 01

  And that's the most unique, most important thing to encourage in the entire world. And the world does not encourage that. The world says, shut the fuck up.

• 2:02:49Rick Rubin?

  Yeah.

• 2:02:50Speaker 01

  The world is like, why are you doing this? In fact, I hear that all the time. They tell, they tell me that, but I have learned, actually, like, this is something I have had to tell a lot of founders who are connected to the source and they're doing something. They're making waves and doing things that like scare people, upset people. They give them ego wounds. And for me, like, if I could do like a message in a bottle, I'm like, you're over the target, bro. You're over the target. Keep going.

• 2:03:18Rick Rubin?

  Yeah.

• 2:03:18Speaker 01

  Like, if you've got someone, someone is mad and like you look at it and it's like, there's nothing underneath that. Like, they don't have a logic. There's no like first principles thinking about like why what you're doing is bad or wrong. It's just vibes and they're like, I hate it. And you can't find like something deeper. And it's, you're over the target, man.

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