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We write in order to leave behind notes for one another.
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I mean, how do we live 10, 000 lifetimes in one?
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What advice do you have for writing a good YC application?
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If I can learn something immediately, that's the part that I like the most.
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How much cringe is the right amount of cringe?
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Some amount is necessary. That's my theory!
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If it's zero, it's not enough.
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You create until your fingers bleed, and then you create some more.
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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.
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I mean, I don't know if you remember shareware days. Uh, That's sorry.
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This was before the internet. So like 1991 92.
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Um, you know, there are these things called bulletin board systems. Sure.
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And so that was sort of the proto internet.
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And, you know, being really, really young, I would just get into these forums.
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And the thing about the forums is like, they couldn't tell how old you were.
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And you could have these long discussions about virtually anything.
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And, um, I feel like my brain more or less developed.
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I liked being treated as an adult instead of being as a child, actually.
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And then, um, I got really into desktop publishing.
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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 the newest PC.
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And so I discovered a, uh, a program called Aldus page maker.
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And it allowed me to basically create my own like underground newspaper and I made one.
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I asked my classmates when I was in 7th grade, um, you know, we should.
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You know, what 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 It was like we were 12 year olds talking about the three strikes law and like criminal justice reform, you know So you were really interested in the ideas.
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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.
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Like, I don't know why we wrote about that stuff short of just that we cared about our society around us.
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And then, uh, I actually learned how to code first by making web pages.
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So, I created an underground newspaper, my 7th grade teacher, uh, would take the, uh, you know, 8 11 sheets, it would be like 10 or 15 pages of just, like, writing by the kids in, like, our English class, and, uh, she'd photocopy, you know, 150 copies and then every single person in our class would get it.
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And then, uh, me being sort of, you know, the short, nerdy, shrimpy kid, like, I suddenly went from really a nobody who'd probably get shoved into lockers, um, and I became someone who, like, people looked up to, and, you know, I had, for the first time, like, Uh, standing within, like, our public school. Influence, too. And I had influence.
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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.
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I mean, the thing that might make you weird as a kid...
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Might make you great as an adult if you don't lose it.
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And that's a line from Kevin Kelly that I know you resonate with.
3:24
Yeah, and that was from, uh, your interview with him. Oh, really? Oh, great. Oh, yeah.
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Yeah, it's, it's a good line.
3:31
So then, so you go from, you go from that, and then you're the editor in chief at this magazine called Express?
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Oh, it's just our school newspaper in high school.
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So, um, I think that just continued. I mean...
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I just really enjoyed not just writing, but also sort of seeing what other people had to say.
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Um, and I, I think there's like sort of a through line to, uh, now my experience on, you know, Twitter or X.
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Like, it's just fascinating.
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Like, I feel like my Twitter feed, uh, sometimes it's actually a curated feed of, you know, dozens of group chats and, you know, dozens of people who normally, Would never get attention.
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So it's actually kind of feels like a distributed newsroom Kind of like just like the old underground newspaper Hmm.
4:17
So what I find interesting is that on one hand early on you have this love for ideas But then you're also reading Kerouac and Milan Kundera So I see sort of the heart fusing with the mind very early. Tell me about that.
4:35
I guess I always sort of expected That we are, we write in order to leave behind notes for one another, um, you know, that's what writing is to me.
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I mean, how do we live 10, 000 lifetimes in one and, uh, it feels like in order to sort of skip ahead, you know, I, I just wanted, I was like desperate for. wisdom from others.
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And then, um, you know, I had a pretty rough childhood and then I could always sort of retreat into the printed page.
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Like I could be anywhere.
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I could understand how other people thought.
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And, um, 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.
5:21
Um, funny story though, uh, I distinctly remember reading, uh, The Fountainhead by Anne Rand, and it actually messed up my college essays. What do you mean?
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Uh, I was, I think, December of, what, 1998, and I was doing, uh, my college essays, and, um, I had sent off my Stanford one already, and then, uh, I remember being in the Fremont Public Library at the main library.
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And, uh, it was the strangest experience.
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Like I remember walking down the hallways and do you ever have this happen?
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Like there's, it's like a book calls out to you and I like look over and then it's like, Oh, this is like.
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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 at it I picked it up and it was like Anne Rand's The Fountainhead 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. Huh?
6:23
And so funny enough like I got waitlisted and rejected from every other school other than Stanford Wow, isn't that funny?
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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 the synesthesia Oh literally like I can see like a halo around this book and that and like for whatever reason I Needed to read that book at that moment.
6:46
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 on it in the late 90s, in the early 2000s. September 10th, 2001.
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Where to find love, how to find love, how to keep love, how to stay in love, where love exists.
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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.
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And love is the word that shows up the most.
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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.
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Like, growing up, um, my parents always said they loved me.
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But my dad also really struggled with alcoholism.
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And so, um, you know, whether it was love of family or Actually, growing up, I was a rabid atheist, um, and I really struggled with the idea of uh, theodicy.
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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.
7:56
Yeah, I read your piece on that. Yeah.
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And 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.
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Or, um, you know, God says that he loves us, but you know, how could there be so much scarcity in the world?
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Um, and I think at that time, I was sort of, in a lot of ways, like, desperate, even suicidal.
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Like, I was really trying to understand.
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Um, what my life, you know, was supposed to be, um, and yeah, in the end, like, I think I tried to find solace in, uh, the great writers, you know, in, in Kerouac, in Kundera, in like whatever, in even in Rand, right?
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Like in anything I could find, um, I was trying to understand, like, what is this thing called life? And like, why am I here?
8:53
How do you think your writing played into that? Your blog? And.
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Your work with the newspaper, how did that factor into your, you making sense of your purpose, your identity?
9:03
I guess what I have now that I did not have back then is, um, what I, like, a felt sense of agency.
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And, um, and I think writing gave me that.
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That, um, even if I was experiencing something, if I could put it to words.
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It would be like indelible and available for others and somehow, like, I mean, I guess, uh, 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, um, Of being?
9:44
Of being, of, of being an individual. Of mattering. Yeah.
9:49
Like sort of the indi like I think being a Chinese American is now what?
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Uh, I realize very un I mean the, the most difficult thing is actually, um, Chinese culture has so much more collectivism.
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And so when you look at, uh, you know, profile photos of people, like in Asia, it's quite common for it to not be your face.
10:09
It's like you and a big crowd. Hmm. And um.
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These are some of the things I think I really struggled with as a child.
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Like, um, you know, I was obviously growing up in, uh, an individualized Western world.
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And, you know, I was, my writing in a way, like, was me trying to develop myself as an individual.
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But I feel like it took, you know, something like 20 or 30 years to fully develop.
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You know, 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, ah, I almost feel agitated in some way.
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And it'll be that, but I'll also feel a pull towards an idea, a pull towards an answer.
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And what I need to do is I'll get interested in something and it's not like, Oh, cool. I'm curious.
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It is like a deep existential I need to answer this question.
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And by writing, by putting vague intuitions into words, it almost gives me a sense of groundedness, a sense of rootedness.
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And then now that I'm stabilized, I feel like my identity grows and expands and becomes. Yes.
11:18
I actually have some sturdiness that I didn't have before. Well, the identity is. Sort of it is written. Yeah in a way.
11:26
Hmm like how do you know who you are until you sort of like put it on a page or you know in a word 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.
11:41
Yeah early on as well I think I feel like you had a very intuitive sense of That the internet was gonna radically reshape both economics, especially the economics of information, and that personal blogs were gonna be this liberating thing.
11:57
Now, I actually think a lot of the momentum of personal blogs has stalled, which is why I do the work that I do.
12:04
I'm like, no, we should have more personal blogs.
12:06
They're, they're important and they're valuable. But, I do feel like...
12:11
You were writing at a time when Bill Gates was on the rise, people 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.
12:22
Yeah, I was really obsessed with the internet, and I still remain very obsessed with the internet. It seemed inevitable.
12:31
And I think that we're still actually even in the early innings of it.
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Like anytime you walk into most workplaces, like if you leave Silicon Valley or you leave, like, even the top four or five, like, sort of, you know, intelligentsia cities in America and you walk into any office, you'll realize, like, people are picking up the phone.
12:50
They're still, like, making decisions over steak dinners.
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Like, that's not necessarily a bad thing, but it's that, um, You know, software and media have not really changed those things yet, and the revolution is still coming.
13:04
Yeah, have you ever seen the clip with David Bowie talking to that BBC interviewer? Yeah, I love it.
13:09
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.
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And David Bowie goes, It's not just a big deal.
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This is like a shift in consciousness.
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This is like an alien life form Oh, yes, and the BBC interviewers like you know, we're talking what drugs are you on?
13:30
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 string I mean he did have that lyric is this what is their life on Mars, right?
13:44
Yeah, David Bowie was all over the place very psychedelic in terms of I was thinking about things. Yeah.
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I think the, uh, that consciousness is changing in like sort of deep fundamental ways.
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It was like long time coming. I mean, that was true.
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The second, I mean, I think it was clear.
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And even when I was 12, it was clear that, um, like media technology on its own clearly shaped all of the 20th century.
14:08
If you look at, uh, 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, um, you know, to steal from Gerard, it's like, you know, the mimesis and the scapegoating
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mechanisms of, um, at the deep societal level were deeply amplified by media technology, and so, um, I'm really taken aback by, uh, the whole idea that, Peter Thiel invested in Facebook very early because of his, um, you know, studying of Girardian writing. Yeah. Yeah.
14:47
Simply because, yeah, like, Facebook, media, social media, the internet, um, they are, like, extreme, uh, carriers of mimesis.
14:56
A few minutes ago, when I asked you about your YouTube channel, you said, Yes, I definitely write the scripts.
15:03
And you said that as if, yes, that's super important to me. Why is that?
15:07
I mean, otherwise, why do it, right?
15:08
Like, it has to be some sort of expression of you to, like, sort of...
15:13
I mean, express yourself.
15:15
I mean, otherwise, why do media at all?
15:18
Actually, um, I guess that's like, I'm actually kind of struggling with this right now where, um, my wife, uh, started a book publishing firm.
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She wants me to write my book.
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And then now she says, Oh, Gary, you should get a ghost writer.
15:31
And I'm like, 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. Yeah. truly my own words.
15:40
Otherwise, you know, it's someone else's experience or someone else's beliefs that are sort of, uh, merged with my own.
15:48
And then to what we were saying earlier, like, I do think about creation as, um, very much about establishing who you are and like, and existence itself, actually.
15:59
Like, otherwise we're just...
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Sort of undifferentiated, right?
16:03
Like, a writer is a writer is a writer.
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Like, I never, I don't want to be a part of that.
16:08
Yeah, I really resonate with what you're saying here, where I feel this need to, like, externalize my identity.
16:15
And, has happened a lot with writing, definitely this podcast of how much I got into the design and all the sets for every episode.
16:24
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 and 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.
16:48
And there's some sense of fulfillment that I get from that, that if I don't have the creation, I feel empty and bare in some weird way.
16:56
Yeah, I'm totally with you.
16:58
I guess as an investor, the other weird thing that I really like is that, um, I want people to know that when I, you know, for whatever reason, the internet seems okay with me shilling people who I think are awesome.
17:14
And I think it's a great blessing.
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Like not many people get that.
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But I try to do the shilling in a way that is authentic to what I believe, like every person that I run across who I think is remarkable or interesting.
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Like I want my megaphone to just.
17:29
Like you know help them and you know feed their world like it's it's sort of like a reddit upvote Like how do we just upvote that thing?
17:38
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.
17:46
This is valuable You should take a look at this when you do marketing how much cringe is the right amount of cringe?
17:52
Oh, we were saying earlier, it sounds like some amount is necessary.
17:55
If it's zero, if it's zero, it's not enough.
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My theory, I think, is that zero cringe is probably suboptimal.
18:03
I think, I mean, basically, if there's zero cringe, you're probably not being authentic, actually. Huh. Say more.
18:14
I mean, zero, it's very hard to be zero cringe, right?
18:17
Like being zero cringe is either totally tasteless or so, um, you know, current thing of the moment that's like so pitch perfect.
18:27
And either is, you know, being yourself is always a little bit weird, you know, it's all, you know, it's, it can, it doesn't seem numerically possible to have zero cringe and be authentic.
18:41
Being yourself is always a little bit weird. That seems interesting.
18:46
Let's pull on that thread.
18:48
I guess that's what I like about just meeting all sorts of people.
18:51
And you know, my job now is essentially just meeting people all the time and then trying to upvote things that are awesome. Right. So.
19:00
Um, my favorite moment is meeting someone who, like, lived a totally different life than me, but, like, taught me something.
19:07
And so, you know, weird is also in the eye of the beholder, so I guess I have a sort of deep preference for novelty.
19:15
Like, if I was just, um, 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.
19:38
There's sort of like a very specific tournament model.
19:41
You have to look like a certain thing and um, 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.
19:54
Upvote, that's a funny word because you've worked with Alexis O'Hanahan, 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.
20:10
What have you learned about forums?
20:13
And how they have shaped the Internet.
20:16
I think it goes back to what we were saying earlier.
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Basically, the Internet's turning into a global brain literally.
20:22
Um, and the voting matters a lot.
20:25
Actually, um, one thing that was kind of interesting, uh.
20:29
Working for Paul Graham back in the day.
20:31
I actually briefly was a moderator for Hacker News.
20:34
Oh, I'm sorry That sounds like the hardest and worst job.
20:39
Yeah, and 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 Small 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, a lot, you know, and it became
21:02
a little bit more of a scary place, and it was because of a but where down votes literally weren't being counted, um, and I think it's just very interesting, like, um, we're sort of at this moment, I'm very obsessed even today about, like, new types of organizations,
21:18
because, you know, I think what's happening is that Um, you know, each of us in a way is like, like a neuron, uh, inside like this larger global brain. And then the mechanism by which those things, you know, the, the neurons communicate like
21:31
And then the mechanism by which those things, you know, the, the neurons communicate like that social media. Right.
21:38
Uh, I actually remember, uh, one of the early investors in Facebook came to speak at YC, um, Yuri Milner.
21:45
And he said, did you know that, uh, 10 percent of the world's.
21:49
Um, energy usage is actually data centers now, and that's about the same, uh, energy usage as a brain inside a human body. Hmm.
21:58
I don't, I never looked it up.
21:59
It might be apocryphal, but it sounded really smart at the moment. Yeah, that sounds smart. Therefore, it's true.
22:04
I mean, but I think that there's something to this.
22:07
How does your background as a designer shape your writing?
22:11
I think design is very helpful in that.
22:15
It is sort of a match pair to writing, um, ultimately all, you know, both writing and online experiences, uh, Sort of float back up to social experiences.
22:28
And, um, I love using analogies around design where, you know, whether it's going to a website or trying a new app or, um, you know, getting an email, that's like the onboarding, like all of those experiences are a lot like, you know, going to a party and a great party.
22:45
Someone greets you, shakes your hand, looks you in the eye, like, makes you feel welcome.
22:48
Hey, these are your friends. Let me take your coat.
22:51
Like, the drinks are over here.
22:52
They hand you, you know, a glass of champagne.
22:54
Like, you're having a great time.
22:56
And so, um, I think online spaces are very similar.
23:01
And then, you know, writing is a very key, important, probably the most important part of, uh, great interaction design, actually.
23:09
I remember when I was spending a lot of time working with companies, like, almost all of it was.
23:15
Uh, a lot of people think, think of design.
23:17
They think of, Oh, what color is the button or, you know, sort of these personal aspects.
23:23
And then I think of it is like almost entirely social.
23:26
And then software is basically the codification of, you know, a conversation that would normally like for everyone.
23:34
If you have 10, 000 users, you're having that 10, 000 conversation 10, 000 times and you can actually evaluate these things on a purely social level.
23:42
Like, Is it, um, the right amount of information? Are you being rude?
23:47
Like, You know, basically, great design is just, um, a good party.
23:51
Well, it's funny to read your writing back in high school, because it was so purply.
23:55
It was over the top, and...
23:57
But, you're gonna say it's terrible.
24:00
I don't think it was terrible.
24:01
It was just very different, and it was over the top.
24:03
But, I actually really admire the way that you were going for it.
24:07
Actually, that's something that I've really admired about...
24:09
All your writing that I've read from literally 25 years, I actually feel like you're always going for, you're always pushing the limits in what it is they're trying to do, but you do say, and it's advice for others, but I think it's really advice for yourself, is
24:23
that great writing is a matter of fact, and I think that When you say that great writing, as a matter of fact, that's a weightier sentence from you, considering that you used to do exactly the opposite. Oh, I had no idea. Oh, I had no idea.
24:36
But I just, I was, you know, drunk with words, is what my, uh, English teacher would always say. Yeah. I just loved words.
24:44
I actually, uh, left to my own devices, I probably would have studied, uh, rhetoric at UC Berkeley instead of computer engineering at Stanford. Is that right? Yeah. No complaints over here.
24:54
It all worked out, but... Yeah.
24:57
And how does your background as a web developer shape your writing?
24:59
I think in the end it comes back to the design aspect.
25:02
Um, I want a great, I actually got to work at, uh, this design firm called Adjacency.
25:07
It was, uh, the design firm that figured out how to make webpages look like magazines and not like, you know, under construction sign.
25:17
It was like sort of 1996.
25:19
It was actually like technically a difficult thing.
25:21
Like you had to, uh, 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. Mm hmm.
25:39
So I always spent time around people who tried to push the boundaries of the medium itself.
25:46
I mean, I think McLuhan's a great example of, you know, the mediums, the message, and, uh, I can totally see that, right? Like the web is. hyper democratized.
25:57
Like there's not really, I like it that way.
26:00
I mean, there's just not a lot of, um, there, there isn't a lot of, you know, sort of ceremony to a website.
26:10
Like it sort of loads and it's there.
26:12
Um, you know, the opposite I think of is, you know, for a wedding, you have to get very fancy stationery. Right.
26:19
Like a webpage, um, is actually somewhat adversarial even.
26:24
Um, one of the things that we talk about often, uh, when working with founders is that You know, when you design your, your home page or like your communications, uh, you have to know that, um, you know, unlike being in the real world or unlike in a book, for instance, you basically are, uh, at competition with every other web page and every other thing that's interesting on the internet. Right.
26:49
You know, every website that you could design has to sort of compare with, you know, going to X on your phone or, um, literally the front page of Reddit and the front page of Reddit is.
27:02
really, really hard to compete against.
27:04
And so in the, on the one hand, it's, you know, no circumstances, just, I mean, no, um, it's just very raw.
27:12
And then literally you have five or 10 seconds or less to prove your value.
27:17
And so it is at once like very raw, but also a perfect competition for human attention.
27:24
What advice do you have for writing a good YC application or just broadly any grant application or something like that?
27:32
I guess personally, I always like, um, very plain spoken and then if I can learn something immediately, that would be, that's the part that I like the most. Why is that important?
27:43
Um, at least for YC, we get a lot of applications. And then.
27:50
Um, when we see something that's novel, it's a little bit obvious, you know, I think that there are tons of, for whatever reason, like I'll give you one, one example that's very, very common.
28:01
Like people love to create apps that help people travel with their friends.
28:07
And when you read, like, I mean, there are crazy stretches when you're reading sort of, uh, what people want to devote their lives to.
28:15
You might read, like, 10 or 15 different things in a row that, you know, have been tried thousands of times, like, same thing over and over again.
28:24
Um, and so the tricky thing is, like, I don't have any advice for that.
28:27
Like, you know, it's almost like the trick to, you know, good writing is being good.
28:32
I don't know how this is terrible.
28:33
Well, I mean, what I'm hearing from you is...
28:35
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.
28:48
Yeah, almost did it It's like where does your magnetic north point towards does it point towards more distinctiveness more individuality more weirdness and I'm gonna go do that, I'm gonna go be okay with people making fun of me, Auntie Sue 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.
29:14
Conformity is actually totally what society, uh, teaches you to do. Of course.
29:19
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 what way?
29:27
You are more or less expected to, uh, write a book report about things, you know.
29:32
It's people, I mean, my experience generally is that school doesn't teach you to be unique.
29:39
Tries to teach you to be, you know, a B, a B plus and then I find middle of the bell curve. Exactly. Yeah.
29:48
If you can be right there, you don't have to be an A plus. It's fine.
29:50
Um, and then I guess simultaneous to that.
29:54
Now we live in this Internet age where.
29:56
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
30:12
I think he says there's literally only one person who could be you and that's you right like the in a world where the internet exists and um But you know being incredibly weird and unique and yourself and having the courage to do that Is really, really important. Mm hmm. Mm hmm.
30:33
How does good documentation work as someone who has no experience coding?
30:39
What, how does good documentation read and is it different from reading an essay? Hmm.
30:45
I guess documentation is really about understanding, so it's Um, I guess the best way to test if the documentation is good, uh, 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?
31:09
And did I get anything wrong?
31:11
Um, with documentation, which is really important for, uh, developer tools and cloud stuff.
31:17
It's kind of like kind of crazy, how important it is.
31:21
Um, 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.
31:28
And, uh, the funniest thing is you have to prevent yourself from saying anything.
31:32
You just have to let them struggle and then have them ask the question.
31:36
Uh, and then the cool thing about that exercise is it's self correcting.
31:40
So the second you see someone struggle or fail to learn how to use something or understand your essay, um, anything that you say.
31:49
To their response basically is literally the thing that needs to find itself back into the writing originally like great writing almost certainly.
31:58
Done right like hits that level perfectly like you shouldn't be explaining absolutely everything.
32:04
You should just explain Exactly what you know 80 90 percent of people need to hear to actually understand what you're saying. How many?
32:13
Influencers have you invested in at YC and is that a path you want to go down more or is?
32:20
writing and running startups directly Oh, I think they work really well together, honestly.
32:26
Um, I think great writers have this capacity to actually just communicate very clearly and then convince things of people.
32:34
And, uh, 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, um, 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, yeah.
33:02
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.
33:13
And so great communication is, um, sort of that 75 IQ thing, like reaching the 75 IQ from the 150 IQ personified.
33:24
What have you learned about effective writing from reading the Bible?
33:29
I guess the number one thing from Girard is actually just this idea of monesis period that, um, writing is, um, the most potent form of representing your experience and, you know, how the world works.
33:46
And then ideally it is, um, beneficial, right? And, and it can spread.
33:53
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.
34:02
Like I couldn't start a company on my own.
34:04
Like, you know, I, if you look at it like modern man can do very little on their own.
34:10
And so the through line for writing is that you need to be able to communicate. Yeah.
34:17
I'm always amazed at how simple the writing in the Bible is, and I'm obsessed with this line that Jesus's presence isn't in his presence.
34:29
And what that means is that he is in so many rooms around the world today.
34:34
He has had so much influence over the years.
34:38
And he's shaping the world every single day, and it comes from scripture, but he's not present in those rooms.
34:45
And I think that that reveals something about great writing.
34:49
You see the same thing at Founders Fund, where Founders Fund orbits around Peter Thiel.
34:53
Peter's been talking about problems with stagnation and the same theses for, for years. And...
35:01
He very clearly shapes the decisions that happen there, and it's affirmed that he has his fingerprints all over.
35:08
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 in every single meeting.
35:14
And that idea that through writing, through narrative, through really good one liners, through stories, that you can be present in a room, in a space, without actually being present there, I find to be very compelling. Yeah.
35:27
I mean, in that respect, like, uh, one of the things I'm certainly learning as a leader is like, you know, sometimes you just become an idea, actually.
35:36
You're sort of personifying, um, you're almost like a human magnet in, in, of, and in and of a sort because, um, and Peter actually has done this incredibly well.
35:47
Like I'm still trying to figure out how it works exactly. Yeah.
35:51
Um, you know, some of the best people I remember hiring at Palantir literally You know, some, uh, college senior at Columbia studying CS, super smart emails, Peter, Peter forwards the email to, to me, we hire him.
36:08
He turns into our best PM working on all this stuff.
36:11
Um, and then, you know, ends up becoming a great CEO in their own right.
36:14
This is the, uh, CEO of Adapar actually. Oh, wow.
36:18
And, um, I think that there's something incredibly impressive about.
36:25
You know, in this age of the internet, you know, you don't have to actually market anything other than what you stand for and what you believe.
36:32
And, um, people who are like minded, they will literally just seek you out.
36:38
You've written that the two elements of effective writing are vulnerability and novelty.
36:43
Vulnerability and novelty.
36:44
Why did you choose those?
36:46
Well, vulnerability is just necessary.
36:49
I mean, I think it's almost, it's, it's a hack.
36:52
But I think from my background and from how I approach writing as a child. I mean just being...
36:58
Being open about who you are and being real and authentic or is it something else?
37:02
Not just that, like, there are certain things that sort of scare you, you know, things that people might not be okay with, um, because we want acceptance, right, but at the same time, like, I mean, it's crazy vulnerable, right, like, things that could open you for
37:20
attack or, um, or close people off, um, 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 seemed to make it okay for people to do so. That's certainly what I'm experiencing now.
37:42
That's certainly what I'm experiencing now. Yeah.
37:45
Um, but I will say like, I was crazy vulnerable earlier when I had nothing.
37:50
And, um, it did not have the same effect.
37:53
So I actually think that there's...
37:55
A really strange inversion that takes place. Say more about that.
37:59
I remember being like, uh, a freshman in college at Stanford.
38:02
And, um, you know, I've, they're definitely like, absolutely obsessed with words.
38:08
And sometimes I would, like, Yes, I think I, like, sent some, uh, you know, overshare type emails to, um, I think my provost at, uh, Stanford, and he literally just, like, didn't know what to do about it.
38:22
Like, you know, I just, it was just awkward because Um, 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.
38:34
And that's like sort of why maybe they got into Stanford in the first place.
38:38
Like they had everything together.
38:40
I feel like I had so little together at some point.
38:43
Um, I had to learn to control the vulnerability a little bit, like what was the right amount for the right person.
38:51
How do you think about doing it now?
38:54
I guess these days, you know, now that I'm in sort of like this power armor sort of situation, like, um, I'm pretty much an open book. Yeah.
39:03
Like Achilles of Silicon Valley when you're in it. Weirdly. Yeah. Yeah.
39:09
I wonder what, where, what exactly my heel is.
39:10
Well, hopefully I don't find out.
39:11
I did not mean that as part of the metaphor.
39:15
It might be this, it might be vulnerability, right?
39:18
But so far, um, I was saying earlier, uh, you know, I have this weird tendency of doing, uh, therapy with my therapist and then going on a podcast.
39:28
And, uh, last time I did it was, um, with Justin Kahn.
39:33
And so that was the first time I publicly talked about, you know, my father, uh, you know, and sort of the type of trauma and abuse I experienced, like, you know, adverse childhood experiences are a thing that I think people really need to come to terms with and very few people talk about it.
39:50
And, uh, I guess now I realize being vulnerable allows people to see not just my humanity, but also see the humanity in their in themselves. And that like.
40:01
This is something that they need to integrate and, you know, do something about.
40:05
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.
40:18
And I think that, for me, why do I write?
40:21
It's because I need to verbalize experience.
40:25
My experience is to have a sense of groundedness or get my bearings in reality. Yeah.
40:34
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.
40:42
Or, you know, there are these things that, uh, Stanford called like tea groups, for instance, like founders come together and, um, 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.
41:03
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?
41:18
Yeah, well, we talked about vulnerability talked about novelty.
41:23
I guess I think people are really obsessed with novelty.
41:28
And when people first start writing, um, they're not really writing for their audience.
41:34
They're actually writing for either themselves or people they look up to.
41:38
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.
41:46
And then, um, that may be true for some people, but I actually think it's, uh, exactly the opposite of what people should try to do, at least initially. Like the things that.
41:55
Seem to be most helpful for a lot of founders actually There's sort of the things I find myself giving advice about like sort of every single day.
42:04
Yeah And those aren't novel things.
42:06
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 it's almost too obvious, um, you know, and the opposite of that is trying to write like, you know, the way the velvet underground push forward rock music or something.
42:26
It's like, it's exhausting.
42:27
Like you can't do it that way. You know?
42:30
All creative acts really are, like, sort of establishing, you know, you as an individual. Yeah.
42:39
Sort of sounds like artistry at that point.
42:40
How do you think about the establishment of you as an individual and the creating of style and identity and things that have that repetition?
42:49
For example, if I see one of your YouTube thumbnails, I'm like...
42:52
That's one of Gary's videos.
42:53
I know exactly what that is.
42:54
How do you think about that and 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?
43:06
I guess the hard part is going back to authenticity and vulnerability, it feels like.
43:11
If you want to change it, you should just change it. Honestly.
43:14
Um, I sort of, I often think about, uh, how bands have like their one hit wonders. Yeah.
43:21
Um, and then when they have their second album, there's like a whole aspect of second album syndrome. Same with second books. Yeah, exactly. Right.
43:30
Um, I, usually it's what you spend 10, 20 years, maybe your whole life building up this one body of work and then boom, you're a success.
43:38
And within, you know, 12 or 18 months, you got to hit them with like the next thing.
43:44
And how could you do that?
43:45
That would like match that first, like magnum magnum opus. It's just. Almost too difficult.
43:51
You have this advice about filmmaking.
43:56
You say you create, you create until your fingers bleed and then you create some more. It's intense.
44:04
I guess, um, more and more, it sounds like artistry. I don't know.
44:09
I mean, I think like starting companies is a little bit that I think, um, you know, YouTube videos done, right?
44:15
Like sort of leave people changed.
44:17
Um, I think what you're doing here is absolutely that.
44:23
Yeah, we're on this earth on just like this sort of like snap of the finger.
44:30
And then the difficulty is how do you make something that's actually worth, like, other people paying attention.
44:35
What have you created that you're the most proud of? Other than family.
44:39
Other than all that stuff.
44:40
I mean, I guess the, the reality is I actually started a venture capital firm and gave it up.
44:46
So I didn't, I didn't create YC.
44:48
I created this seed investment firm called Initialized. Yeah. So, um. YouTube videos?
44:55
The obvious one is there's my top viewed video is, uh, how to get rich.
45:03
And, uh, I almost feel silly.
45:05
It seems to be a fairly effective title.
45:07
Yeah, but I feel good about it in that I'm taking this, like, very base thing that's, you know, sort of...
45:15
Almost too flippant and then I drop in, uh, 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, uh, 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? Yeah.
45:42
Well, if we were sitting down on that couch and you're like, David, David, David, I have to show you something that you've made, what would it be? That I've made? Shoot.
45:51
When I look at, um, 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.
46:00
Um, I might be a very different type of creator.
46:04
Like I, I actually just try to create regularly and I sort of don't know what's going to come back. Right.
46:13
And, um, I'm hoping, like, the thing I'm most proud of I haven't created yet, actually. Yeah.
46:20
But, I mean, that's the tricky thing, like, I came up through blogs, I came up through YouTube videos, like, these things are not books. Mm hmm.
46:28
Like, they are, uh, almost meant to be, you know, watched and then sort of, like, let go, right? Mm hmm.
46:37
And that's why I sort of feel impelled to, like, continue to create, um, cause, I don't know. You know, I think that. My story's not done yet.
46:45
I'm still trying to figure out this thing, and I'm trying to figure out.
46:48
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.
47:04
Early on in your blog, it's very raw.
47:06
It is, hey, this is what's on my mind.
47:08
This is what I'm thinking about.
47:10
These are the things I like.
47:11
Here are the things I don't like.
47:12
Here are the things I'm struggling with.
47:13
Here are the things I'm excited about. This is what's going on.
47:15
I'm just going to pour out my soul onto the page.
47:17
And that seems to be your style.
47:19
It is very much what's topical, what's top of mind.
47:24
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.
47:30
They're just sort of the river, the river, just sharing what's top of mind and getting it out there, the flow.
47:35
Yeah, that seems to be just what I can fit in, in my busy schedule.
47:39
Yeah, I, you know, maybe this is just.
47:41
It's a function of like, you know, my writing has never been my like number one thing.
47:47
It's always been like, you know, grinding as a founder, grinding as an engineer.
47:52
And then even blogging, it was just something that I, I did for fun on the side.
47:57
Like it wasn't, I, I, I have still yet not made it my primary thing. Yeah.
48:02
Um, but I am proud of even just walking around, whether it's like in startup land or just even walking around in the city, sometimes I'll run into someone and they'll walk up to me and just start talking to me. Yeah.
48:15
Uh, and I might not know them, but I like to sort of carry on.
48:19
You know, my side, it's a parasocial relationship, but that doesn't prevent me from just playing along on my side because I realize this person often they've spent like 10, 20, 30 hours with me. Yeah.
48:33
And so I actually feel sort of obligated to, you know, sort of hear about them. Like.
48:38
They spent 20 hours with me, I need to know, like, something about them, like, let me get to know them.
48:42
So, that, that I find very, very fun and interesting.
48:47
What kind of writing do you do at YC?
48:50
Writing to all the founders, writing to all the people who work at YC? Oh, the internal stuff. Yeah.
48:58
Well, what's weird now is realizing there are over 10, 000 people who have, who are part of the community. So that's founders. Yeah. Yeah.
49:08
10, 000 founders and alumni.
49:09
And then if you know, you extend it to employees, it's hundreds of thousands to millions.
49:14
So, you know, one of the things we realize is.
49:18
That's so big that like we should sort of think of even those communications as like media actually. Of course.
49:24
Like how do we think about helping those sets of people and then getting those people connected?
49:29
And then the scale is crazy.
49:30
Like this past weekend we had 2, 700 people together and um, it felt like a massive reunion cause literally everyone who you could meet, we all had the same set of values and um, it felt like home.
49:44
Well what's cool about YC is how many good writers have come through it.
49:48
I mean, obviously it's founded by Paul Graham, but Sam Altman's a hell of a writer. Absolutely. His blog's great. Yeah.
49:58
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.
50:09
And insofar as that's a cultural shift, that's one we're celebrating.
50:13
Well, we need to keep going.
50:15
I mean, the outcome is that we just want more abundance.
50:17
Like, we just want more people to actually succeed.
50:20
Um, I think the thing that got me was realizing when you read Paul Graham's essays, it was like, you know, even the term or phrase, um, you know, solving the money problem was, Like you would just see immediate recognition in that.
50:34
And it's like, Oh, I think about that all the time.
50:36
And, um, you know, working really, really hard on a startup that solves problems that then solves the money problem for you.
50:44
Um, if you just recognize that, that will just attract all the same people who are trying to do that.
50:51
What should writers learn from successful founders?
50:55
I guess the best founders have a very clear outcome in their mind.
50:59
Like when you meet Brian Chesky, he's like, how do I connect people?
51:04
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.
51:14
Like when you meet most people, it's like, Oh, I want to be more famous.
51:17
I want to be, I want to have more money.
51:19
I want to spend more time.
51:21
Vacationing someplace fancy, like those are all like very surface level.
51:25
Like the thing that I really am impressed by for certain founders is that they like pick this thing that.
51:32
You know, it's sort of like what we talked about earlier with, um, with movie making great filmmakers are like, you know Let me just do this until my fingers are raw and they're gonna keep doing it, right and I think that's hard Honestly, it's really hard we're
51:49
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. Like, all of these things were happening to me.
52:05
Like, all of these things were happening to me.
52:08
I had, like, certain skills.
52:10
I had, you know, certain things that I, like, didn't understand.
52:14
Um, I was dealing with, like, something that, you know, honestly, even now, like, I haven't really written about what really happened to me as a child.
52:23
Like, I can refer to it, but, like, it's... Still way back there.
52:27
And um, I think it's how you figure out who you are.
52:32
Yeah, 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?
52:42
Amen, 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 good? What's going on?
52:53
You seem a little you seem a little off And I said, yeah, well, I just published this, this essay.
52:59
And I feel like I had carved out a part of my identity. I had put words to it.
53:06
Deep things that had happened in my life beliefs that I hadn't made sense of things that felt 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.
53:27
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 at You would think, oh, I'm trying to attract a big audience, I'm gonna write things that everyone has gone through, I'm gonna focus on scale, share everybody's experiences.
53:44
And actually, it's the opposite that really resonates.
53:48
It's writing about yourself.
53:49
What is the pain, the emotion, the drama.
53:51
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.
54:09
There's something paradoxical and profound about that.
54:11
I guess that's what media is to me.
54:13
It's actually less the like outcome of some process and more about building relationships.
54:23
Understanding my, my place in the world and, you know, sort of helping other people understand theirs. Mm hmm.
54:31
Vannevar Bush and the mimics, that's something that seemed to be very striking for you early on.
54:37
Yeah, I mean, it seems like it's here and it's called, uh, a large language model. Yeah. Say more.
54:43
Um, I guess the mimics was just an interesting exercise in how do you actually...
54:48
How do you have human computer symbiosis?
54:50
How do you actually have a computer that, you know, computers do all the things that humans are terrible at.
54:55
It's great at math, it's great at remembering things, but it's kind of terrible at, um, reasoning.
55:02
And, you know, I think the memex had this, all these aspects of, Um, how do you extend human capability by doing, you know, helping humans do those things that humans are bad at while relying on, um, you know, human intuition and reasoning.
55:20
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.
55:31
And it seems like, you know, your GPT 4 session.
55:36
Has this capability of reasoning and so, you know, I, you know, now that I say it like it's possible that the memex is an antiquated notion like the idea.
55:46
It's almost like the idea that, uh, you know, pre right brothers.
55:49
We thought maybe you'd have to flap your wings to fly. Right?
55:53
And instead, you know, the, the action of flight is like radically different than birds.
55:57
Actually, that's a great analogy.
56:00
Graphomania, the desire to write books to a public of unknown readers. You talk about this.
56:05
It's from Milan Kundera, from the book of Laughter and Forgetting.
56:09
Why do you think that resonated with you?
56:11
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.
56:20
It was so cool to see man Like I'd 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 has so clearly been with you the entire time.
56:40
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.
56:48
I would have thought about who you are much more in a resume way. Yeah, that makes sense.
56:54
I guess I was writing all that stuff just because, I mean, some of it was actually, frankly, the love of the technology itself.
57:00
I think when I was putting together a lot of those websites, I was just obsessed with the craft of making a website, period.
57:08
And, um, I think I was influenced by a lot of the crazy writing about what the internet could be.
57:15
And I wanted to have my voice out there.
57:17
And I distinctly remember putting my zine online and we got tons of comments.
57:24
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, right?
57:44
So, uh, but that was the beauty of it that, um, without their permission, you know, without their 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.
58:12
Like, that's the world that we live in now, like literally 30 years later, uh, I'm amazed at what's happening a little scared, but still absolutely amazed.
58:24
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.
58:36
If you're a great writer, like, there are, there's a bigger audience than has ever existed, and especially because it's completely democratized.
58:46
Yeah, well that's what really excites me about online writing, is you can be whoever.
58:51
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.
59:02
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.
59:15
Uh, so Gary, thank you so much.
59:17
This was, this was a blast.
59:18
It was really fun to research for this, and it was even better to do the interview.
59:22
Thank you so much for having me.