We write in order to leave behind notes for one another. I mean, how do we live 10,000 lifetimes in one? What advice do you have for writing a good YC application? If I can learn something immediately? That's the part that I like the most. How much cringe is the right amount of cringe? That some amount is necessary. That's zero. That's zero. It's zero. It's not enough. You create until your fingers bleed and then you create some more. In a world where the internet exists, being incredibly weird and unique and yourself.
And having the courage to do that is really, really important. I mean, I don't know if you remember shareware days. Sorry. This was before the internet. So, like, 1991, 92, you know, there are these things called bulletin board systems. And so that was sort of the proto-internet. And, you know, being really, really young, I would just get into these forums. And the thing about the forums is like they couldn't tell how old you were.
I don't know if these long discussions about virtually anything. And I feel like my brain more or less developed. I liked being treated as an adult instead of being as a child, actually. And then I got really into desktop publishing. So, you know, one thing that I feel really lucky about is my parents always made sure I could have access to, you know, sort of a newest PC. And so I discovered a program called All Dispage Maker. And it allowed me to
basically create my own, like, underground newspaper. And I made one. I asked my classmates when I was in seventh grade. You know, we should, you know, what do you, if you were going to make a newspaper, what would you write about? And it was all kinds of stuff. Like, I remember one of my best friends at the time wrote about how, you know, Pete Wilson and the three strikes law in California was unjust. And it was like, I'm like, 12 year olds talking about the three strikes law and like criminal justice reform, you know.
So you were really interested in the ideas. It was the ideas that drew you to writing from a very, very early age. Yeah, I mean, that we could have an opinion about these things. We could educate ourselves. And then that it was important to do so. Like, I don't know why we wrote about that stuff, sort of just that we cared about our society around us. And then I actually learned how to code first by making web pages.
So I created an underground newspaper. My seventh grade teacher would take the eight and a half by 11 sheets would be like 10 or 15 pages of just like writing by the kids in like our English class. And she'd photocopy, you know, 150 copies. And then every single person in our class would get it. And then me being sort of, you know, this short nerdy, shrimpy kid. Like, I suddenly went from really a nobody who probably get shoved in the lockers.
And I became someone who like people looked up to. And, you know, I have for the first time, like standing within like our public school influence. And I had influence. So I guess weirdly, a lot of the things that now I'm known for I learned when I was doing an underground newspaper in seventh grade happens a lot. I mean, the thing that might make you weird as a kid might make you great as an adult if you don't lose it. And that's a line from Kevin Kelly.
And I know that you resonate with. Yeah. And that was from your interview with him. So really? Yeah. Great. Oh, yeah. Yeah. It's it's it's a good line. So then so you go from you go from that. And then you're the editor in chief at this magazine called Express. Oh, it's just our school newspaper in high school. So I think that just continued. I mean, I just really enjoyed not just writing, but also sort of seeing what other people had to say.
And I think there's like sort of a through line to now my experience on, you know, Twitter or X like it's just fascinating. Like I feel like my Twitter feed sometimes is actually a curated feed of, you know, dozens of group chats and you know, dozens of people who normally would never get attention. So it's actually kind of feels like a distributed newsroom kind of like just like the old underground newspaper.
So what I find interesting is that on one hand early on you have this love for ideas. But then you're also reading caroac and Milan, Kunderra. So I see sort of the heart fusing with the mind very early. Tell me about that. I guess I always sort of expected that we are we write in order to leave behind notes for one another. You know, that's what writing is to me. I mean, how do we live 10,000 lifetimes in one nice.
And it feels like in order to sort of skip ahead, you know, I just wanted I was like desperate for wisdom from others. And then you know, I had a pretty rough childhood. And then I could always sort of retreat into the printed page like I can be anywhere I could understand how other people thought. So, you know, sometimes I would just go to the library and like pick out books at random and just just read them just for fun. Funny story though.
I'd stinkly remember reading the fountain head by Anne Rand and it actually messed up my college essays. So, you mean I was I think December of what 1998 and I was doing my college essays and I had sent off my Stanford one already. And then I remember being in the Fremont Public Library at the main library. And it was the strangest experience.
And I remember walking down the hallways and do you ever have this happen like there's like a book calls out to you. And I like look over. And then it's like, oh, this is like it was almost like it's like in a video game when there's like a halo around like a particular book. And I looked it up and it was like Anne Rand's the fountain head and I read it and it made me an asshole.
And all of my other essays were kind of not something that personally if I was reading that application, I don't think I would have accepted it. And so funny enough, like I got waitlisted and rejected from every other school other than Stanford. Wow. Isn't that funny? Yeah. So, I often think about that because I never experienced that sort of like weird synesthesia.
Who knows what it means? But I mean by this synesthesia. Oh, literally, like I can see like a halo around this book in that. And like for whatever reason, I needed to read that book at that moment. So well early on you have an interest in in love that really shows up. There's a lot of writing that you're doing it on it in the late 90s and the early 2000s September 10th, 2001. Where to find love, how to find love, how to keep love, how to stay in love, where love exists.
In this giant post that you wrote that is like all one giant sentence with commas about all the things that you're interested in and love is the word that shows up the most. Yeah. I mean, when I think about it, I looking back on my childhood. I mean, that was one thing that I think I struggled with like growing up. My parents always said they loved me, but my dad also really struggled with alcoholism. And so, you know, whether it was love of family or actually growing up, I was a rabid atheist.
And I really struggled with the idea of the Odyssey. So how could a just God who loves us create a world that is like this impoverished or this that could be so unjust or so wrong. Yeah, I read your piece on that.
So, you know, when you bring up the end of that quote, I'm like, yeah, the thing that, you know, I sort of had a deep questioning of is like, you know, my parents say they love me and then they do all these things or God says that he loves us, but you know, how could there be so much scarcity in the world. And I think at that time, I was sort of in a lot of ways like desperate, even suicidal. Like I was really trying to understand what my life, you know, was supposed to be.
Yeah, in the end, like I think I tried to find solace in the great writers, you know, in in in Kandara and like whatever in even in Rand, right, like in anything I could find. I was trying to understand like what is this thing called life and like why am I here? How do you think you're writing played into that your blog and your work with the newspaper, how did that factor into your, you making sense of your purpose, your identity.
I guess what I have now that I did not have back then is what I felt sense of agency and I think writing gave me that. That even if I was experiencing something, if I could put it to words, it would be like indelible and available for others and somehow like, I mean, I guess one of the more salient things for Asian Americans often is like this idea of existing of like, and I distinctly remember.
What do you mean by existing just of being of being of being of being an individual of mattering like sort of the end like I think being a Chinese American is now what I realize very I mean the most difficult thing is actually. Culture has so much more collectivism and so when you look at you have profile photos of people like in Asia, it's quite common for it to not be your face. It's like you and a big crowd and these are some of the things that I think I really struggle with as a child.
I was obviously growing up in an individualized western world and I was my writing in a way like was me trying to develop myself as an individual but I feel like it took something like 20 or 30 years to fully develop.
One of the things that I'm hearing that we very much share in common is for me a lot of times I'll feel like a sense of being destabilized or something and I'll be like, I almost feel agitated in some way and it'll be that but I'll also feel a pull towards an idea, pull towards an answer.
What I need to do is I'll get interest in something and it's not like, oh, cool, I'm curious. It is like a deep, existential I need to answer this question and by writing by putting vague intuitions into words, it almost gives me a sense of groundedness, a sense of rootedness and then now that I'm stabilized, I feel like my identity grows and expands and becomes. Yes. I actually have some sturdiness that I didn't have before. Well, the identity is sort of it is written in a way.
Like how do you know who you are until you sort of like put it on a page or you know, you know, we're processor or a text editor and like it's there. And if you don't believe it, like literally you just select it and delete it. Yeah, early on as well, I feel like you had a very intuitive sense that the internet was going to radically reshape both economics, especially the economics of information and that personal blogs were going to be this liberating thing.
Now, I actually think a lot of the momentum of personal blogs has stalled, which is why do the work that I do. I'm like, no, we should have more personal blogs. They're, they're important and they're valuable, but I do feel like you were writing at a time when Bill Gates was on the rise, we were talking about the information superhighway and you were very much peering into the future to see, hey, everyone is going to be able to share their ideas.
Yeah, I was really obsessed with the internet and I still remain very obsessed with the internet. It seemed inevitable and I think that we're still actually even in the early innings of it. Like anytime you walk into most workplaces, like if you leave Silicon Valley or you leave like even, you know, the top four or five, like sort of, you know, intelligentsia cities in America.
Yeah, and you walk into any office, you'll realize like people are picking up the phone. They're still like making decisions over steak dinners. Like that's not necessarily a bad thing, but it's the, you know, software and media have not really changed those things yet and the revolution is still coming.
Yeah, have you ever seen the clip with David Bowie talked in that BBC interviewer? I love it. Yeah, he's like the BBC interviewer is like, yeah, so I don't understand why you keep saying this internet thing is a big deal. And David Bowie goes, it's not just a big deal. This is like a shift in consciousness. This is like an alien life form. Oh, yes. And the BBC interviewer is like, what are you talking about? What drugs are you on? What's funny is like, I wonder if the drugs actually helped.
Probably. I mean, they probably helped him become a lot more attuned to what was going on. And I mean, he did have that lyric, is this what is their life on Mars? Right? David Bowie was all over the place, very psychedelic in terms of how he's thinking about things. Yeah, I think the consciousness is changing in like sort of deep fundamental ways was like long time coming. I mean, that was true.
The second, I mean, I think it was clear and even when I was 12, it was clear that like media technology on its own clearly shaped all of the 20th century. If you look at, you know, obviously there was industrialization, but there was also mass literacy.
And so with newspapers, you could create a national identity that would like galvanize people in a way, you know, to steal from Gerard. It's like, you know, the Mimesis and the scapegoating mechanisms of at the deep societal level were deeply amplified by media technology. Sure. And so I'm really taken aback by the whole idea that Peter Tiel invested in Facebook very early because of his, you know, studying of Gerardian writing.
Yeah. Simply because, yeah, like Facebook media, social media, the internet. They are like extreme carriers of Mimesis. A few minutes ago, when I asked you about your YouTube channel, you said, yes, I definitely write the scripts. And you said that as if, yes, that's super important to me. Why is that? I mean, otherwise, why do it? Right. Like it has to be some sort of expression of you to like sort of, I mean, express yourself.
I mean, otherwise, why do media at all? Actually, I guess that's like, I'm actually kind of struggling with this right now where my wife started a book publishing firm. She wants me to write my book. And then now she says, oh, Gary, you should get a ghost writer.
I don't know if I want to have one because I don't want, you know, if it's truly my book or my memoir, I want it to be truly my own words. Otherwise, you know, it's someone else's experience or someone else's beliefs that are sort of merged with my own. And then to what we were saying earlier, like I do think about creation is very much about establishing who you are and like, and existence itself, actually. Like, otherwise, we're just sort of undifferentiated, right?
A writer is a writer is a writer. Like I never, I don't want to be a part of that. Yeah, I really resonate with what you're saying here where I feel this need to like externalize my identity and it has happened a lot with writing definitely this podcast of how much I got into the design and all the sets for every episode. And then in Austin, I built a production studio and every book on the shelf, every record on the wall, the wallpaper, the carpets, everything is intentional.
Everything is like resonates with like some vibration that I feel within that I just need to get outside and then just outside of me. And then I can just walk through the space and I can be like, wow, this is actually who I am. And there's some sense of fulfillment that I get from that that if I don't have the creation, I feel empty and bear in some weird way. Yeah, I'm totally with you.
I guess as an investor, the other weird thing that I really like is that I want people to know that when I, you know, for whatever reason, the internet seems okay with me, shelling people who I think are awesome. And I think it's a great blessing. Like not many people get that.
But I try to do the shelling in a way that is authentic to what I believe, like every person that I run across who I think is remarkable or interesting, like I want my megaphone to just like help them and feed their world. Like it's sort of like a Reddit upvote. Like how do we just upvote that thing?
And then the greatest blessing in the world that now, you know, the world has sort of granted me is to be able to say, this is worthy, this is interesting, this is valuable. You should take a look at this. When you do marketing, how much cringe is the right amount of cringe? Oh, we're saying earlier, sounds like some amount is necessary. That's right. Zero. That's right. Zero. It's not enough. My theory, I think is that zero cringe is probably sub-optimal.
Yeah, I think so. I mean, basically, if there's zero cringe, you're probably not being authentic, actually. Huh, say more. I mean, zero, it's very hard to be zero cringe, right? Like being zero cringe is either totally tasteless or so, you know, current thing of the moment that's like so pitch perfect. And either is being yourself is always a little bit weird, you know, it's all, you know, it's, it's, it can pass on, it doesn't seem numerically possible to have zero cringe and be authentic.
Being yourself is always a little bit weird. That seems interesting. Let's pull on that thread. I guess that's what I like about just meeting all sorts of people and, you know, my job now is essentially just meeting people all the time and then trying to upload things that are awesome. Right. So my favorite moment is meeting someone who like lived a totally different life than me, but like taught me something.
And so, you know, weird is also in the eye of the holder. So I guess I have a sort of deep preference for novelty. Like if I was just, I mean, maybe this is why earlier in my career, like when I graduated from college studying computer engineering, like I applied to the gap, thinking like, oh, maybe I could be a fashion designer.
And I applied to an advertising agency, thinking like, I would really enjoy like coming up with memes and jingles and, you know, what I didn't understand was like society isn't built that way. There's sort of like a very specific tournament model. You have to look like a certain thing. And I just found a lot of, I was just like deeply interested in all the different things that go into, you know, making the world work.
And then I just found a vote that's a funny word because you worked with Alexis Ohanahan who founded Reddit and Hacker News is run by YC. So you've been very close, closely orbiting around probably the two of the biggest forums in the world. What have you learned about forums and how they have shaped the internet? And then I went back to what we were saying earlier, basically the internet's turning into a global brain literally. And the voting matters a lot actually.
One thing that was kind of interesting working for Paul Graham back in the day, I actually briefly was a moderator for Hacker News. Oh, I'm sorry. That sounds like the hardest in worst job ever. The wild thing was, and I don't think this has ever been public, but I actually think Paul introduced a bug into Hacker News for not that long, like some, like maybe a month or two, where down votes were not being counted. But the consciousness of Hacker News changed dramatically.
Actually, so it became a lot nastier. And it became a little bit more of a scary place. And it was because of a butt where down votes literally weren't being counted. And I think it's just very interesting. We're sort of at this moment. I'm very obsessed even today about new types of organizations, because I think what's happening is that each of us in a way is like a neuron inside this larger global brain.
And then the mechanism by which those things, you know, the neurons communicate like that social media, right? I actually remember one of the early investors in Facebook came to speak at YC, Yuri Milner. And he said, did you know that 10% of the world's energy usage is actually data centers now. And that's about the same energy usage as a brain inside a human body. I don't, I never looked it up. It might be apocryphal, but it sounded really smart. It sounds like it's true.
I mean, but I think that there's something to this. Like, how does your background as a designer shape your writing? I think design is very helpful in that it is sort of a match peridor writing. Ultimately, both writing and online experiences sort of float back up to social experiences. And I love using analogies around design where whether it's going to a website or trying a new app or getting an email that's like the onboarding.
All of those experiences are a lot like going to a party and a great party. And one greets you, shapes your hand, looks you in the eye, makes you feel welcome. Hey, these are your friends. Let me take your coat. Like the drinks are over here. They hand you a glass of champagne. Like, you're having a great time. And so, I think online spaces are very similar. And then, you know, writing is a very key and probably the most important part of great interaction design.
When I was spending a lot of time working with companies, like almost all of it was a lot of people think of design. They think of, oh, what color is the button or sort of these personal aspects. And then I think of it as like almost entirely social. And then software is basically the codification of a conversation that would normally like for everyone.
If you have 10,000 users, you're having that 10th that conversation 10,000 times. And it you can actually evaluate these things on a purely social level. Like, is it the right amount of information? Are you being rude? Like, you know, basically great design is just a good party. Well, it's funny to read your writing back in high school because it was so purple. It was over the top.
But you're going to say it's terrible. I don't think it was terrible. It was just very different. And it was over the top. But I actually really admired the way that you were going for it. Actually, that's something that I've really admired about all your writing that I've read from literally 25 years. I actually feel like you're always going for your always pushing the limits and what it is they're trying to do. But you do say as advice for others, but I think it's really advice for yourself.
That great writing is matter of fact. Oh, yeah. And I think that when you say that great writing is matter of fact, then so weightier sentence from you considering that you used to do exactly the opposite. Oh, I had no idea. But I just, I was, you know, and drunk with words is what my English teacher would always say. Yeah. I just loved words. Actually, left in my own devices, I probably would have studied rhetoric at UC Berkeley instead of computer engineering is Stanford.
Is that right? Yeah. But no complaints over here. It all worked out. And how does your background as a web developer shape your writing? I think in the end, it comes back to the design aspect. I want a great, I actually got to work at this design from called adjacency. It was the design from that figured out how to make web pages look like magazines and not like, you know, under construction sign.
And it was like sort of 1996. There's actually like technically a difficult thing like you had to, you know, figure out before the background tag, you had to create an image tag that would be a full page bleed. And then you had to figure out how to compress JPEGs so that they could be really large and legible, but like still load on a 28, 8 modem.
So I always spent time around people who try to push the boundaries of the medium itself. I mean, I think McLeulins a great example of, you know, the mediums, the message. My boy. Yeah. And I can totally see that, right? Like the web is hyper democratized. Like there's not really, I like it that way. I mean, there's just not a lot of. There, there isn't a lot of, you know, sort of ceremony to a website like it sort of loads and it's there.
You know, the opposite, I think, is, you know, for a wedding, you have to get very fancy stationary, right? Like a web page is actually someone ever serial, even one of the things that we talk about often when working with founders is that, you know, when you design your your home page or like your communications. You have to know it.
You know, unlike being in the real world or unlike in a book, for instance, you basically are at competition with every other web page and every other thing that's interesting on the internet, right? Like, you know, every website that you could design has to sort of compare with, you know, going to X on your phone or literally the front page of Reddit and the front page of Reddit is really, really hard to compete against.
And so, on the one hand, it's, you know, no circumstances, just, I mean, no, it's just very raw and then literally you have five or 10 seconds or less to prove your value. And so it is at once like very raw, but also a perfect competition for human attention. And I think it's a good advice you have for writing a good YC application or just broadly any grant application or something like that.
I guess personally, I always like very plain spoken. And then if I can learn something immediately, that would be that's the part that I like the most. I see we get a lot of applications and then when we see something that's novel, it's a little bit obvious, you know, I think that there are tons. For whatever reason, like I'll give you one example, it's very, very common. Like people love to create apps that help people travel with their friends.
And when you read, I mean, there are crazy stretches when you're reading sort of what people wanted to vote their lives to. And you might read like 10 or 15 different things in a row that, you know, have been tried thousands of times, like the same thing over and over again. And so the tricky thing is like, I don't have any advice for that. Like, you know, it's almost like the trick to, you know, good writing is being good.
I mean, what I'm hearing from you is have some distinct and differentiated ideas. And I think this goes back to the weirdness thing that we were talking about. I think that a lot of what blocks people from writing well is an inability to lean into their own weirdness. It's like, where does your magnetic North point towards? Does it point towards more distinctiveness, more individuality, more weirdness?
And I'm going to go do that. I'm going to go be okay with people making fun of me. Antisu not getting it at the Thanksgiving table. Or is it pointing towards conformity and banality so that I can fit in when I'm hanging out with the bar, at the bar with my friends? That's true. So conformity is actually totally what society teaches you to do. Of course. And most people have to write in sort of a school context. And I think that's incredibly toxic in a lot of ways actually. In a way.
You are more or less expected to write a book report about things. You know, it's people. I mean, my experience generally is that school doesn't teach you to be unique. It tries to teach you to be, you know, a B, a B plus. And then I find myself. Middle the velcro. Exactly. Yeah. If you can be right there, you don't have to be an A plus. It's fine.
And then I guess simultaneous to that. Now we live in this internet age where every person on this planet could probably reach every other person on the planet. Or at least, you know, the top half of that world. And, you know, hopefully we can transform that aspect. But. That means that there can only like I like what Naval says. Like, you know, I think he says there's literally only one person who could be you. And that's you. Right.
And in a world where the internet exists and. But you know, being incredibly weird and unique and yourself and having the courage to do that is really, really important. How does good documentation work as someone who has no experience coding? What? How does good documentation read and visit different from reading an essay? I guess documentation is really about understanding. So it's pretty much the same as a good essay as well.
I guess the best way to test if the documentation is good might actually be similar to testing an essay with others, which is just send the essay to people and ask them. Ask them questions like about do you understand what I was trying to say and did I get anything wrong with documentation, which is really important for. Developers tools and cloud stuff is kind of crazy how important it is.
You can almost sit next to someone as they try to, you know, use something technical and either they get it or they don't. And the funniest thing is you have to prevent yourself from saying anything. You just have to let them struggle. Yeah. And then have them ask the question. And then the cool thing about that exercise is it's self-correcting. So the second you see someone struggle or fail to learn how to use something or understand your essay.
Anything that you say to their response basically is literally the thing that needs to find itself back into the writing originally. Like great writing almost certainly done right like hits that level perfectly. Like you shouldn't be explaining absolutely everything. You should just explain exactly what you know 80 90% of people need to hear to actually understand what you're saying.
How many influencers have you invested in at YC and is that a path you want to go down more or is writing and running startups directly opposed to each other. Oh, I think they work really well together. Honestly, I think great writers have this capacity to actually just communicate very clearly and then convince things or people. And I think there's this interesting meme on the internet right now around like sort of 75 IQ and 150 IQ and in between is the midwit.
And the through line is if you can say something very simple like you know it might be something that's incredibly high IQ like 150 IQ. But the magic is that if you can explain it at the 75 IQ level like you understand it so completely and so thoroughly like you know you can hire you can convince customers you can you know get investors to invest all of whom could be 75 IQ and it doesn't matter.
And so great communication is sort of that 75 IQ thing like reaching the 75 IQ from the 150 IQ personified. Yeah. What have you learned about effective writing from reading the Bible? I guess the number one thing from Gerard is actually just this idea of an in the mesus period that writing is the most potent form of representing your experience and you know how the world works. And then ideally it is beneficial right and and it can spread.
And then everything that we want to do in our world in our lives like has this sort of intersection with society and other people like no man's an island like I couldn't start a company on my own like you know I if you look at it like modern man can do very little on their own. And so the through line for writing is that you need to be able to communicate very effectively.
I'm always amazed at how simple the writing in the Bible is and I'm obsessed with this mind that Jesus is presence isn't in his presence. And what that means is that he is in so many rooms around the world today he has had so much influence over the years and he's shaping the world every single day.
And it comes from scripture but he's not present in those rooms and I think that that reveals something about great writing you see the same thing at Founders Fund where Founders Fund orbits around Peter teal. Peter has been talking about problems with stagnation and the same feces for for years and he very clearly shapes the decisions that happen there and it's a firm that he has his fingerprints all over but at the same time he's not always in the room.
And if you talk to people who are there they say yeah Peter's not never single meeting and that idea that through writing through narrative through really good one line or through stories that you can be present in a room in a space without actually being present there. I find to be very compelling.
I mean in that respect like one of the things I'm certainly learning as a leader is like you know sometimes you just become an idea actually you're sort of personifying like you're almost like a human magnet in an in and of the sort because and Peter actually has done this incredibly well like I'm still trying to figure out how it works exactly.
You know some of the best people I remember hiring at Palantir literally you know some college senior at Columbia studying CS super smart emails Peter Peter forwards the email to to me we hire him he turns into our best PM working all this stuff and then you know ends up becoming great CEO in their own right this is the CEO of Adapar actually well and.
I think that there's something incredibly impressive about you know in this age of the internet you don't have to actually market anything other than what you stand for and what you believe and. People who are like minded they will literally just seek you out you've written that the two elements of effective writing or vulnerability and novelty vulnerability and novelty why did you choose those.
Well vulnerabilities just necessary I mean I think it's almost it's it's a hack but I think from my background and from how I approach right to find a child I mean just being open about who you are and being real and authentic or is it something. Not just that like there are certain things that sort of scare you you know things that people might not be okay with.
Because we want acceptance right right but at the same time like I mean that is crazy vulnerable right like things that could open you for attack or or close people off. I think you have to be careful with it right like on the other hand for me in my in my life I just found that. Sharing what was going on for me like however unpleasant actually seem to make it okay for people to do so that's certainly what I'm experiencing now.
But I will say like I was crazy vulnerable earlier when I had nothing and it did not have the same effect so I actually think that there's a really strange inversion that takes place.
Same more about that I remember being like a freshman in college at Stanford and you know I was there definitely like absolutely obsessed with words and sometimes I would like yes I think I like sense some you know over share type emails to I think my provost at Stanford and he literally just like didn't know what to do about it like you use I just it was just awkward because.
I didn't realize it at the time but you know I guess by and large Stanford kids are pretty well adjusted and have you know really great parents and that's like sort of why maybe they got into Stanford in the first place like they had everything together I feel like I had so little together at some point. I had to learn to control the vulnerability a little bit like what was the right amount for the right person.
How do you think about doing it now I guess these days you know now that I'm in sort of like this power arm sort of situation like I'm pretty much like a killer yeah I wonder what we're what exactly my heal is will hopefully I don't find out I did not mean that it's part of it. I'd be this it might be vulnerability right but so far I was saying earlier you know I have this weird tendency of doing therapy with my therapist and then going on a podcast and last time I did it was with Justin con.
And so that was the first time I publicly talked about you know my father you know and sort of the type of trauma and abuse I experience like adverse childhood experiences are I think that I think people really need to come to terms with and very few people talk about it and I guess now I realize being vulnerable allows people to see not just my humanity but also see the humanity in themselves and that like.
This is something that they need to integrate and you know do something about a lot of the writing that has moved me the most was some feeling that either I didn't feel alone or somebody was putting words to an experience that I'd only felt but never actually verbalized and I think that for me why do I write it's because I need to verbalize experience my experiences to have a sense of groundedness or.
Get my bearings in reality yeah and honestly like the best places in the world are you know the tiny dinner party where people get really real about what's going on or you know there are these things that Stanford called like tea groups for instance like founders come together and share like basically the things that are most scary to share in the world but like in small groups of people for whom like they can trust each other.
And I think that that's what we want as human beings like we want connection we want to feel that we're not alone you know we want a community of people who have each other's back yeah and when that happens you know really quite magical and honestly like we can find that on the internet now how crazy is that yeah what we talked about vulnerability talked about novelty I guess I think people are really obsessed with that.
People are really obsessed with novelty and when people first start writing they're not really writing for their audience they're actually writing for either themselves or people they look up to and then the bar for it ends up being like I have to come up with something that impresses me and the people I most respect right and then that maybe true for some people but I actually think it's exactly the opposite of what people should try to do at least initially like the things that seem to be most important.
It seems to be most helpful for a lot of founders actually there's sort of the things that I find myself giving advice about like sort of every single day yeah and those aren't novel things those are sort of the commonplace things and so I would say the most important type of novelty is the stuff that does come up all the time but is almost too obvious.
And the opposite of that is trying to write like you know the way the velvet underground push forward rock music or something it's like it's exhausting like you can't do it that way you know all creative acts really are like sort of establishing you know you as an individual yeah sort of sounds like artistry at that point.
What do you think about the establishment of you as an individual and the creating of style and identity and things that have that repetition for example if I see one of your YouTube thumbnails I'm like that's what a Gary's video I know exactly what that is how do you think about that in the consistency that's required to establish a brand but also just the expression and the natural ebbs and flows and change of a human being.
I guess the hard part is going back to authenticity and vulnerability it feels like if you want to change it you should just change it honestly. I sort of I often think about how bands have like their one hit wonders yeah and then when they have their second album there's like a whole aspect of second album syndrome same second books yeah exactly right.
Usually it's what you spend 10 20 years maybe your whole life building up this one body of work and then boom your success and within you know 12 or 18 months you got to hit them with like the next thing totally and how could you do that that would like match that first like Magnum Magnum Opus is just almost too difficult. You have this advice about filmmaking you say you create you create until your fingers bleed and then you create some more intense.
I guess more and more it sounds like artistry I don't know I mean I think like starting companies is a little bit that I think you know YouTube videos done right like sort of leave people changed.
I think what you're doing here is absolutely that yeah we're on this earth I'm just like this sort of like snap the finger and then the difficulty is how do you make something that's actually worth like other people paying attention what if you created that you're the most proud of other than family other than all that stuff I mean I guess the reality is I actually started a venture capital firm and gave it up.
So I didn't I didn't create why see I created this seed investment firm called initialized yeah so how about in terms of writing YouTube videos the obvious one is there's my top viewed video is how to get rich. And I almost still yeah a fairly effective title yeah but I feel good about it in that I'm taking this like very base thing that's you know sort of almost too flippant and then I drop in an excerpt of Alan Watts talking about the nature of money.
And it's like everyone's expecting this one thing that's very and then boom like let me hit people with a philosophical idea that I think will help people who are literally searching for the most basic of things and you know how do we elevate that into an outward direction.
Well if we were sitting down on that couch like David David David I have to show you something that you've made what would it be that I've made shoot when I look at other people I respect I mean I think PG probably has Paul Graham probably has a few essays that he's extra extra proud of yeah I might be a very different type of creator like I I actually just try to create regularly and I sort of don't know what's going to come back.
Right and I'm hoping like the thing I'm most proud of I haven't created yet actually yeah but I mean blood that that's the tricky thing like I came up through blogs I came up through YouTube videos like these things are not books like they're almost meant to be you know watched and then sort of like let go right and that's why I sort of feel impelled to like continue to create.
Because I don't know I think that my story is not done yet I'm still trying to figure out this thing and I'm trying to figure out well I think a lot of what you're creating then is a relationship with people at scale a sense of I think people feel a real sense of intimacy in the YouTube videos that you have even the way that you have the camera set up it's very close it's not big and grand early on in your blog it's very raw it is hey this is what's on the mind this is what I'm thinking about.
These are things I like here the things I don't like here the things I'm struggling with here the things I'm excited about this is what's going on I'm just going to pour out my soul onto the page and that seems to be your style it is very much what's topical what's top of mind it doesn't seem like you're going to work you it doesn't seem like you've worked on creative projects for years at a time they're just sort of the river the river just sharing what's top of mind and getting it out there the flow.
Yeah that seems to be just what I can fit in in my busy schedule so maybe this is just a function of like you know my writing has never been my like number one thing it's always been like you know grinding as a founder grinding as an engineer and then even blogging it was just something that I did for fun on the side like it wasn't I I have still yet not made it my primary thing yeah
but I am proud of even just walking around whether it's like in startup land or just even walking around the city sometimes I'll run into someone and they'll walk up to me and just start talking to me yeah and I might not know them but I like to sort of carry on you know my side it's a parasocial relationship but that doesn't you prevent me from just playing along on my side because I realize this person often they spent like 10 20 30 hours with me.
Yeah and so I actually feel sort of obligated to you know sort of hear about them like they spent 20 hours with me I need to know like something about them like sure let me get to know them so that that I find very very fun and interesting what kind of writing do you do at YC writing to all the founders writing to all the people who work at YC. Oh the internal stuff yeah well what's weird now is realizing there are over 10,000 people who have or part of the community.
So that's founders yeah yeah 10,000 founders in alumni and then if you know you extend it to employees you know hundreds of thousands to millions so you know one of the things we realize is that's so big that like we should sort of think of even those communications as like media actually of course. Like how do we think about helping those sets of people and then getting those people connected and then the scale is crazy.
This past weekend we have 2700 people together and it felt like a massive reunion because literally everyone who you could meet we all had the same set of values. Yeah and it felt like home. Well what's cool about YC is how many good writers have come through it. I mean obviously it's founded by Paul Graham but Sam Altman's a hell of a writer. Absolutely.
This blog's great. Yeah. And I think that's one of YC's big contributions to the world is clear thinking, good writing, teaching at scale can get you somewhere. And in so far as that's a cultural shift that's one we're celebrated. Yeah. Well we need to keep going. I mean the outcome is that we just want more abundance. Like we just want more people to actually succeed. I think the thing that got me was realizing when you read Paul Graham's essays and was like you know even the term of phrase.
You know solving the money problem was like you would just see immediate recognition in that. It's like oh I think about that all the time. And you know working really really hard on a startup that solves problems that then solves the money problem for you. If you just recognize that that will just attract all the same people who are trying to do that. What should writers learn from successful founders? I guess the best founders have a very clear outcome in their mind.
Like when you meet Brian Chesky he's like how do I connect people? There's like a why that is way beyond like sort of the classic you know tropes or the classic things that you might run across. Like when you meet most people it's like oh I want to be more famous. I want to be I want to have more money. I want to spend more time vacationing someplace fancy. Like those are all like very surface level.
Like the thing that I really am impressed by for certain founders is that they like pick this thing that like you know. It's sort of like what we talked about earlier with with movie making. Yeah. Great filmmakers are like you know let me just do this until my fingers are raw and they're going to keep doing it right. And I think that's hard honestly it's really hard. We're sort of born into this world and don't know who we are. And then.
I mean through this conversation I'm sort of like sort of thinking back on my own writing and who I became and the origins were trying to figure out who I was. Yeah. All of these things were happening to me. I had like certain skills. I heard had you know certain things that I like didn't understand. I was dealing with like something that you know.
And I was actually even now like I haven't really written about what really happened to me as a child like I can refer to it but like it's still way back there. And I think it's how you figure out who you are. And maybe that's actually the scariest question. Yeah. So like actually confront what who you are where you came from like what's deep down real for you.
I had a piece I published a few years ago and I had published the piece 24 hours 48 hours before this conversation and someone said, what's going on? You seem a little you seem a little off. And I said, yeah, well I just published this this essay. And I feel like I had carved out a part of my identity. I had put words to it. And I had a lot of things that had happened in my life beliefs that I hadn't made sense of things that fell intimate and private and revealing.
And then I published it and I just shared it with the world. And of course that's destabilizing. But somehow I have a deep compulsion to do that. That makes sense. That makes sense to me. That speaks to me. Sometimes they say that there's the universal in the particular and I'm always amazed that you would think, oh, I'm trying to attract a big audience. I'm going to write things that everyone has gone through. I'm going to focus on scale share everybody's experiences.
And actually it's the opposite that really resonates. It's ready about yourself. What is the pain, the emotion, the drama, the feelings that you've had. And somehow by really zooming into your own reality, finding something inside of you. That's maybe the size of a penny or even smaller. There's something that gets magnified in that in the human experience that we can all connect with that very individual experience. There's something paradoxical and profound about that.
I guess that's what media is to me. It's actually less the like outcome of some process and more about building relationships. I understand my place in the world and helping other people understand theirs. Van of our bush and the mimics. That's something that seemed to be very striking for you early on. Yeah, it seems like it's here and it's called a large language model. Yeah. Same more. I guess the mimics was just an interesting exercise and how do you actually have human computers and beoses?
How do you actually have a computer that computers do all the things that humans are terrible at? It's great at math. It's great at remembering things. But it's kind of terrible at reasoning. And you know, I think the mimics have this all these aspects of how do you extend human capability by doing that, you know, helping humans do those things that humans are bad at while relying on human intuition and reasoning.
And I guess what's tricky is now that we say it, the large language model might be beyond it because you know, there are aspects of theory of mind. It seems like, you know, your GPT-4 session has this capability of reasoning. And so, you know, now that I say it, like it's possible that the mimics is an antiquated notion, like the idea, it's almost like the idea that, you know, pre-right brothers, we thought maybe you'd have to flap your wings to fly. Right.
And instead, you know, the action of flight is like radically different than birds, actually. That's a great analogy. Grafomania, the desire to write books to a public of unknown readers, you talk about this, it's from Miland Kundera from the book of laughter and forgetting. Why do you think that resonated with you?
I guess early, it's very, it's a very strange experience to think about this because, you know, back when I was making these websites that you found on the internet, it was so cool of the same man. I never, like I think maybe a hundred people would have seen that. That was, I just love seeing that because I just got the sense of this raw, passionate, creative enthusiasm that was so, that is so clearly been with you the entire time.
And as I looked at your career through the lens of that kid, I just saw this fire that radiates everything that you do, and had I not seen that, I would have thought about who you are much more in a resume way. Yeah, that makes sense. I guess I was writing all that stuff just because, I mean, some of it was actually, frankly, the love of the technology itself.
When I was putting together a lot of those websites, I was just obsessed with the craft of making a website period. And I think I was influenced by a lot of the crazy writing about what the internet could be. And I wanted to have my voice out there. And I distinctly remember putting my scene online. And we got tons of comments from people who took it at face value, sort of equal to, you know, something in CNN or anything else.
Like that felt incredible to me, like as even a 12 or 13 year old to be taken seriously, you know, as they say on the internet, nobody can tell you're a dog. So, but that was the beauty of it that without their permission, you know, without having an editorial board come and see it, like without having to, you know, have access to a printing press, which, you know, really brought together so much power into the hands of the few and the wealthy.
Like to have the ability to communicate so thoroughly and completely available to everyone, like that's the world that we live in now, like literally 30 years later, I'm amazed at what's happening a little scared, but still absolutely amazed.
And I think what used to be something that was a much smaller sort of discipline, maybe there were, you know, a finite number of jobs where you could spend all your time writing. Like today, if you're a great writer, like there, there's a bigger audience than has ever existed. And especially because it's completely democratized.
Yeah, well, that's what really excites me about online writing is you can be whoever you're talking about being 12 or 13 years old, there's people who are anonymous, and I've spoken with people who work around Congress, and they are influenced by some of these anonymous writers. And that does return to some of the original promises of the internet, the democratization that you could have influence from anywhere.
And I really see online writing as one of the places where the internet is really at its best. So Gary, thank you so much. This was this was a blast. It was really fun to research for this, and it was even better to the end of real. Thank you so much for having me.