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Paul Graham.
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Paul Graham is the business writer who became successful by breaking the rules of business writing. We learned it in school. We heard it.
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They said that your writing's got to be filled with jargon. He said, "Nope.
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I'm going to write with plain and simple language."
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And then they said that in order to be successful as an adult.
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If you want to write, you got to publish books.
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You got to publish PDF white papers.
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He said, "Nah, I'm going to write long form essays on the internet and I'm just going to publish them.
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I'm going to share them for free for anybody to read."
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And he's been enormously successful.
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I mean, sure, he sold a company to Yahoo, but that's not what he's going to be remembered for.
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He's going to be remembered for starting Y Combinator, which has gone on to create something like hundreds of billions of dollars in value for the companies that have gone through it.
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Reddit, Airbnb, Dropbox, bunch of them.
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But how has writing led to Paul Graham's success? What has he done? Well, you know it.
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He's written a bunch about startups and business and how to generate wealth and a bunch of other topics too that have given people like me have made people like me be really big fans of PG.
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But I didn't realize this until I started working on this episode that Y Combinator was actually born out of an essay on his site called How to Start a Startup.
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and his readers were some of the first applicants in YC.
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They heard about YC through his website.
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And then the first batch included the founders of Reddit, Twitch, and also Sam Alman, who eventually became the president of YC and is now the head honcho of the AI boom.
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But then his writing also attracted Patrick Collison, the founder of Stripe, which YC ended up investing in super early. So there you have it.
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I think PG is the guy that we should be teaching people to write like in English classes all around the world. and to Elm Mundo.
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But that's not going to happen.
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We're going to keep teaching people how to write like literature and novels and like teaching third and fourth grader Shakespeare.
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I don't really get why we do that.
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Because of that, we're bringing the Paul Graham master class to How I Write with David the Writing Guy. So, what is this?
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This is a deep dive about how PG or he writes, how he thinks about the craft, how he thinks about editing in particular.
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And what I've done is I've taken all of his best lessons and then I said, "Okay, let's structure this video in lessons that we're going to go through one by one. There's 11 of them."
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And then if you stay till the end, right at the end, I have an unreleased goodie in here about what Sam Alman learned from Paul Graham.
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They worked really closely together.
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Sam Alman ended up becoming the president of YC and PG has been a mentor to Sam and I'm not going to share that anywhere else.
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This is what Sam learned from Paul Grant. So, here we go.
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Lesson number one, write simply. Write simply.
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PG says that something comes over people when they try to be creative.
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When he's talking about designers, he talks about how they get all artistic with swooshes and swirls and curls, all that nonsense.
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Writers do the same dang thing.
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They'll write with words that sound nothing like how they talk or naturally express themselves.
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They'll use fancy language, SAT words, words with so many syllables that like you'd have to clap your hands to keep up with them all.
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I remember when I was in school, we used to say this word anti-isestablishmentarianism.
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Anti-isestablishmentarianism.
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It had so many syllables and we were like, "Wow, it's so impressive that you know that."
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And people will write sentences like, "And when the writing is convoluted, the readers obfiscate their inherent cander with deceptive sophistication and entanglement." It's ridiculous. It's ridiculous.
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It's better to just say writers use unnecessarily big words.
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Like you, like me, PG grew up writing needlessly complicated things.
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And what he was doing was he was writing a bunch of short stories that didn't have a plot.
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But then what he did was he was like, I need to impress my English teacher.
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So he would create characters with these strong feelings because he thought that that's what made stories deep, which is so funny when you think about where he used to be and where he is now.
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And then later on, that's what he did sort of when he was in elementary school and middle school.
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And then when he was applying to art school, what he tried to do, he was writing his essay and he tried to get all intellectual.
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He wrote this piece about Saison, you know, the French painter.
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Trying to get all intellectual and like sound smarty as possible.
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But what he learned, and I quote here, he says that you don't need complex sentences to express complex ideas. You don't need it.
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And actually, when you have all that complexity, it hurts your ability to communicate.
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And that's fundamentally what writing is.
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It's like you have an idea in your brain that you put onto paper and then you've written it and then there's a reader there and then they take those ideas and they put it into their brain.
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And so what you're trying to do is get that information transfer, right?
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And you can think that whenever somebody's reading, there's basically a finite amount of energy that they can expend.
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And they're sitting there, they're reading, and you can almost think of it, they have an energy budget for that time.
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And the easier it is for people to understand your writing, the more they can then focus on the ideas, which is what really matters, the ideas. The ideas.
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So once you really distill your writing down, you just make it so whoop, it's streamlined right into the brain and then they can focus on the ideas.
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And I noticed this over the past few days as I've just obsessed over PG's writing. It is so distilled. It's so distilled.
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And we're going to talk about this a lot more later on. And here's the thing.
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This is why PG likes to focus on simplicity.
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He says that when you're forced to be simple, you have to face the real problem.
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You have to face what you're actually talking about, what you're actually trying to say.
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And you can't hide behind the nonsense anymore.
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You have to deliver substance.
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You have to deliver substance. It's just right there.
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It reminds me of whenever I go get really high-end sushi, which is one of my favorite things to do.
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You go to a great sushi restaurant and they're generally just the higher end the place, the simpler the sushi.
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You go, you get sushi at the grocery store, you get these California rolls, there's all these sauces, these different foods.
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They're kind of coming together. high-end sushi.
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It's just fish, rice, maybe a light sprinkle of sauce. That's it.
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And it reminds me of another thing.
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So, when I was in college, I used to watch Casey Neistat's vlogs every single night. I love them.
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And Casey Neistat was once asked why his videos were so simple.
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He uses these standard Helvetica fonts, straightforward cuts, no filters, no color correction, stories that are easy to follow, basic accessible methods. Why? Why does he do that?
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Well, he says it's like a steakhouse.
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Great ones, they serve their fillets alakart.
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Steak plate, nothing else.
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Maybe a tinge of sauce like the sushi.
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But it's the bad steak houses that like douse their meat in A1 sauce.
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All this nonsense to distract you from the lowquality food that's right in front of your eyes.
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And that's why the first lesson from PG is just to write simply. Write simply. Focus on the ideas.
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Get rid of the ornamentation.
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It's going to force you to really make sure that the meat of what you're saying is quality.
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Lesson number two, great writing comes from great editing.
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Great writing comes from great editing.
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How does PG make his writing so simple?
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I'll tell you what, it's not about the first draft.
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It's about the obsessive editing that goes into it.
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It's easy to think of him as a great writer and then a great first draft writer.
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Oh, this guy, he sits down, he has all these perfectly formed ideas in his brain.
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You know, he lives in this small town in England.
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He's probably walking through the little countryside, the village.
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He's in his English manor house and he's just walking around with these perfect ideas, this all just ready to go.
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But no, that's not what being a great writer is about.
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It's about being a great deleter.
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It's about being a great deleter.
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That delete key, top right corner of your keyboard, that's the one that you got to get good at. Or the highlighting.
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Okay, this chunk, I don't need it in there.
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And it's because he's a great deleter that he doesn't waste words.
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And the thing is, you're sitting down, you're reading the piece, you're like, "Wow, this is so good."
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And it's so easy to just underestimate how much he's ended up deleting because you just you can't see it. You can't see it. It's not there.
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PG says, and I quote, "You want to be quick to cut.
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One of the most dangerous temptations in writing is to keep something that isn't right just because it contains a few bits or costs you a lot of effort.
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And for him, writing is sort of like the equivalent of line drawing.
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I'm going to use a bunch of painting and drawing metaphors here because that is true to PG.
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He spent a bunch of time thinking through software and drawing.
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I mean, actually, that's why his book is called Hackers and Painters.
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Hackers and Painters, sort of that left side of the brain, skepticism, rigor, logic.
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And painters, sort of that right side of the brain, imagination.
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And if you look at a line drawing, how are they done?
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Once again, you look at the drawing and it just seems so perfect.
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the swirl, the swoosh, the line, they're just all right in the right place.
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But like a good piece of writing that comes out through trials and trials of effort. You're trying something. H, not quite right. Try some over here. Ah, not quite right.
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And you're just going and going and going until you find the right shape.
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And just like we were talking about earlier with how you're writing and writing to get to a place where it's simple so that you don't have that ornamentation.
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It's the same thing with a line drawing, right?
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Every single stroke, that movement of the brush needs to be in the right place.
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And PG learned this from Da Vinci, Leonardo da Vinci.
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He says, "Some Leonardo heads are just a few lines."
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Talking about some of his drawings.
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You look at them and you think, "All you have to do is get eight or 10 lines in the right place and you've made this beautiful portrait."
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Well, yes, but you have to get them in exactly the right place.
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The slightest error will make the whole thing collapse.
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Line drawings are in fact the most difficult visual medium because they demand near perfection.
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And PG's essays are like a line drawing for writing.
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I mean, sure, there's some of those curves and there's some beauty and there's some poetry in there, but it's simple. It's simple.
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You don't have all that ornamentation.
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Just about everything that's unnecessary.
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Everything that doesn't contribute, it's been removed.
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It's been taken away so that only the essential stuff remains.
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I want to hear something funny.
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So, as I was prepping for this, I was like, am I going to include direct quotes?
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Because actually last night, I was helping a friend with a lecture that he's giving about Rouso, the philosopher.
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And I was like, dude, every single time that you go into the direct quote, I feel like it's really jarring because the way that Russo writes is so different from the way that people talk.
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But PG is totally the opposite.
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the opposite. I've kept a lot of quotes in here because I want you to hear something that the quotes use almost the same words that I speak with and that is one of the things that people love so much about PG's writing is just how he
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writes like you would talk simple straightforward common language and it gets me into what I call the paradox of writing which is that great writing looks ef effortless, but because the ideas are so clear, casual readers don't appreciate how much time it took to refine them. You see that in PG's
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You see that in PG's work where even for somebody like him, maybe even especially for somebody like him, you have to know that the majority of what he writes probably isn't that good. Yeah.
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I mean, I guess, sure, his first draft is probably better than yours, probably better than mine. Like, fine.
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But I actually don't think that's what makes the difference.
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And I bet if he was sitting right here with us, he'd say the same thing.
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That the difference really lies in the editing.
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It lies in the refinement, the deletion, the removal, and then the stuff that you read that I read where I'm like, "This is good. This guy is inspiring."
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That's just the small percentage of things that he chooses to keep.
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And I don't know what it is.
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Amateur writers time and again, they want everything that they write to be great.
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They're like, I'm a good writer because everything I write on paper is great.
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But this is a game of slugging percentage, not batting average.
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It's not what percentage of the things that I end up typing is really good.
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It is what how good are the really good things that I write and then how good can I be at deleting so that only the good things remain and those are the only things that end up publishing.
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trying to make everything perfect when you write all your perfect first drafts.
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That's just the wrong thing to go for.
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And PG says that one of the biggest things that holds writers back and actually anybody in general that holds people back from doing great work is the fear of making something lame.
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Most projects look lame at the beginning.
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And if you're going to write, if you're going to be successful in any endeavor, you have to get comfortable with the ugliness, the messiness, the sludge of an idea in its early stages.
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And then you just got to push through.
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And PG wants you to ask a question.
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Think about this for your writing.
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What could you achieve if you could turn off the fear of making something lame?
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How much more could you create?
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And this is what's so pernicious about the whole thing is nobody even knows that you made something lame. Like, you have no idea.
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I have no idea how lame the worst things that PG has written are.
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All we know is the stuff that he publishes tends to be pretty good.
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And we're like, nice, you're a good writer.
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The goal isn't for everything you write to be great.
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The goal is for everything you publish to be great.
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And there's a huge difference between those things.
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Somebody who writes way more junk than the average person in their first draft, but then only publishes what's excellent is going to have a reputation for being a great writer. So, how do you do that? How do you do that?
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How do you get yourself comfortable with the lameness of your early drafts?
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How do you get to a place where you're like, "Yeah, not a big deal.
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I know it's not that good, but that's fine."
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And what you could do is you can just change the frame of how you're thinking about this creation where in the world of painting, you're not making a painting.
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You're working on a sketch.
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In the world of software, you're not making some grand piece of software.
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You're just sort of hacking around.
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You're not working on an essay.
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You're just writing a letter to friends.
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Hey, maybe you're texting friends.
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I notice all the time people who sometimes say that they're bad writers are great text messengers.
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It's like they'll write ripping text messages to me. I'm like, it's funny.
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It's got a great main point. It's good examples.
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And then they sit down to write.
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They get all rigid and sclerotic and they're at the keyboard and now they have writer's block.
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Now they're just plagued and tormented.
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You got to get to a point where you can just have a lower standard for the initial things you create.
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And I know that that's counterintuitive, but sometimes that low standard actually helps you be creative, get stuff onto the page, get stuff going, and then yeah, once the project's rolling, sure, just convert it into something more.
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It reminds me of a few years ago in our second read of passage cohort.
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We had a student and she's thinking of joining the the the course.
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So, she writes me this brilliantly written email.
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And when I say it was well written, I mean it.
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It was like, "Here's my skepticism, my objections, here are my questions."
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And I was like, "Wow, she can rip. She is a good writer. Such good questions."
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And we end up getting her in the cohort and it's like a month later.
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We're at the end and she's about to publish this piece and she's like, "David, I'm just not a good writer. I can't publish. I have writer's block.
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I'm not confident at all in what I say.
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It's just really not a good writer.
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I I I don't think I'm ready to publish.
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and I read her writing and it wasn't very good.
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So I was like, "What's going on here?
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How could her email before have been awesome, fantastic, and then her writing wasn't good?"
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And it was because she was using the wrong frame.
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When she was writing me an email, she was writing directly to me and the stakes were low.
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When she was writing an article, she was now writing to an audience of people and the stakes were high.
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The writing wasn't the problem.
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The problem was the frame.
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She can write well in emails, but she freaks herself out whenever she writes for public consumption.
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And that's why PG says you got to focus on the editing.
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Great writing comes from great editing.
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And if you can lower the stakes in the early versions of a project, you're going to be better off.
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So then the question is, all right, well, how do you edit?
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Well, I do know one thing.
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I do know that he prints things out instead of editing on the computer.
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And I've done this a few times.
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If you plan to do that, here are some tricks that I've discovered.
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One is, so you print it out, you got the piece of paper, you're reading, just grab a highlighter and highlight every section where you feel stuck or frustrated.
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You almost think of like, imagine a flat surface.
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Imagine every place where you just have some bump in the road. Okay? And just highlight it.
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You don't need to fix it. Just that simple. Just highlight it.
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Get stuck, make a highlight.
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And read through the entire piece. Just go start to finish.
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Stop only to make highlights. be really quick. Zing, clip, zing, clip. Just little thing.
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And then take that and then go through the highlights on the computer and then that's when you do the fixing.
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So the consumption of what you're editing and the fixing of what you're editing, they happen at different times.
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See, the problem with editing, trying to make all the fixes in the moment is sometimes you get really distracted.
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And then I also like editing with a printed out piece of paper.
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I actually should probably do it more.
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And what I like about it is that when you're doing it on the computer, editing on the computer, it's really easy to get distracted and now you're get fixing things on the fly instead of staying in that reading flow.
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So, print out the piece of paper, get your highlighter, and just nick the parts that need improvement.
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And then you can also ask friends for help.
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You'll notice that if you scroll to the bottom of PG's essays, you'll see all these names.
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Patrick Collison, Sam Alman, Robert Morris, Jessica Livingston, his wife, and these are people who have helped him work on the piece.
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So, what does he do when he asks for help?
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Well, he does two things.
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There's two things that he wants to know from his readers.
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Number one, what parts bore them?
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Number two, what parts seem unconvincing?
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What parts seem unconvincing?
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The boring bits, those can usually just be fixed by cutting them.
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You can just get rid of them. No problem. but unconvincing.
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I didn't expect to see that.
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So, what does he do when he finds something that's unconvincing?
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Well, he does not immediately jump back into writing.
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Instead, what he does is he talks about the idea, talks about it with other people until he gets clarity.
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So, he basically has these sparring partners.
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He'll sit down, he'll be talking it out.
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And I don't know this to be a fact, but when I do that, the questions that people ask show me what parts of what I'm saying aren't all that clear.
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And then my answers help me to clarify what's going on.
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Because the thing is, this the curse of knowledge that once you know an idea fairly well, it's hard to remember what parts are obvious and intuitive and what parts aren't going to be easily understandable to the average person.
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Another tip, and I learned this from Tim Ferrris on a episode of How I Write, where what he does when he asks for friends is he says, "What is the 10% I need to keep no matter what?
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And then what is the 10% I'll cut if I absolutely had to cut it?"
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Talking to friends and asking for what is the 10% that you would cut?
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I think that's a good piece of advice.
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Yeah, you have you have total protective air cover from my my request.
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Similarly, like if you could only keep 20%.
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And if 20% sounds too abstract, you can just say one out of every five pages can stay. That's it. Which stay?
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Yeah, I'm giving you a chapter that's 20 pages, right? So there you go.
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The reason why I think that works is when you ask friends for help, they often don't want to give you negative feedback.
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But if you basically force them to say, "You got to get rid of this stuff."
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You're going to be better off because now they feel safe saying, "Hey, I don't think this part was good enough."
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And then you get that more that more honest feedback. Here's another one.
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This is one of my favorite analogies for editing.
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It comes from Neil Strauss.
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He says that uh editing is like getting the wrinkles out of a shirt.
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Some they're going to be easy to remove.
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You know, you just got that little wrinkle here, little wrinkle there, and then sometimes going to take a little bit more work, but with enough persistence, you always get there.
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You have a nice smooth shirt.
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And it's the same thing with editing where you're just looking what are the wrinkles, what are the wrinkles, what are the wrinkles, and those are the little nicks that you've highlighted.
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And PG is meticulous about editing.
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It has me feeling what I call the paradox of creativity where I say that your work is done when it's so simple that the reader, whoever is looking at your writing, they actually think they could have done what you did cuz it's so simple, so easy, which then means that they won't appreciate how hard you worked.
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So the paradox of creativity is that when you do a good job, people don't realize how hard you worked.
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And that's what I see with PG's essays.
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He says that he sometimes rewrites them, edits them, doesn't rewrite the whole thing, but rereads his essays 50 times.
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And he says, "Good writing is rewriting.
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Good design is redesign."
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It's actually rare that you get things right the first time.
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For me, I hear that, I just go, "Ah, that's such a relief.
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It's such a relief that I don't have to be perfect the first time.
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That gives me the freedom to fall, to fail, to mess up, to stumble and strut around like a two-year-old at the playground who's just like falling over and falling over.
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You know, they're just learning how to walk.
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That's sort of what the early versions of an essay are like.
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You should expect to throw away a lot of your early work. Just expect it. That's fine. Don't feel bad for it.
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Like in Leonardo's drawings, there are sometimes five, six, seven attempts to get it right.
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I learned this in the research for this episode that PG writes that the distinctive back of the Porsche 911, that famous car, it only came out of a redesign from an awkward prototype. How cool is that? How cool is that?
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And that's how PGs think about writing.
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That often when you're redesigning, you're rewriting.
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That's when you find things you would have never found without writing.
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The process of refinement isn't just about removal.
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It is inherently creative and you just discover things from the problems that inevitably emerge.
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Which takes me to lesson number three that writing generates ideas.
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You should expect 80% of the ideas that you have about a topic to come after you start writing the piece.
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And then like half of those pieces are going to be wrong.
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And this once again is why editing is so important.
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PG says, "The first words that you choose are usually wrong.
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You have to rewrite sentences over and over to get them exactly right.
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And your ideas won't just be imprecise, but incomplete, too.
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Half the ideas that end up in an essay will be ones that you thought of while you were writing it."
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Indeed, that's why I write essays, to find the ideas that I can only find by writing.
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And that means that the problem with not writing is that you're missing out on the ideas that writing would have generated.
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All those things that you're going to get by writing, that you're going to get by focus, if you do not sit down to the keyboard, you're never going to find those ideas.
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And the great misconception of writing is that people who write something brilliant, they just wake up every morning, they have all the ideas in their head, they just sit down and they type out a perfect transcript of what's magically in their mind.
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Every single day, there's this perfect revelation. But that's not true.
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Writing is how you discover those ideas.
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Rewriting is how you discover them.
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You go deeper and deeper until you find things that you hadn't seen before.
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And it's not just that experts tend to write.
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It's that writing leads to expertise.
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It's not just that PG writes well because he's an expert about startups.
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PG is an expert about startups because he's written so much about them.
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And that's why you should write PG gives us a chilling thought.
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He says, "If writing down your ideas always makes them more precise and more complete, then no one who hasn't written about a topic has fully formed ideas about it."
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Then no one who hasn't written about a topic has fully formed ideas about it. Huh?
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That's why lesson number three is writing generates ideas.
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You don't just write about the ideas that are already in your brain.
27:05
You use writing as a way to discover things that you've known that you didn't know that you knew.
27:14
What kinds of ideas should we be looking for?
27:15
Well, that brings me to lesson number four.
27:18
Find ideas that are general and surprising.
27:24
Those are the most valuable ones. general and surprising.
27:25
That's like the holy grail for PG.
27:30
He says that if you have surprise without being general, you have something like gossip.
27:33
Oh my goodness, you'll never hear what Katie did over the weekend.
27:37
Oh my goodness, can you believe what happened with Ben? Whatever.
27:42
It's surprising, but it's not general.
27:43
It's like that only applies to that situation in that moment in time.
27:48
And then sometimes you have something that's general like a general piece of knowledge or insight or wisdom but it's just not surprising.
27:54
And then you have a platitude work hard be kind.
28:02
It's like yes but it's not surprising.
28:04
So then if general and surprising is what we're going for in our writing, how do you find things that are general and surprising? And PG lays it out.
28:15
He says, "Here's one thing you can do.
28:19
Pay attention to what you find interesting.
28:24
What you find interesting, not what other people think is going to be interesting.
28:28
What you find interesting."
28:30
Because a bunch of really important discoveries, they've been made by people who've just been pulling on threads, following little trails of things that actually seem fairly insignificant at first.
28:41
Like Darwin goes to to the Galapagos and he's like, "How can they all be finches?" Innocuous question.
28:50
And you're just following your nose, following your curiosity.
28:57
PG says that when you find yourself very curious about an apparently minor question, well, that's an exciting sign. Follow that.
29:08
And see, if an idea feels incomplete, that's fine. It's standard, actually.
29:11
like you have this question and you're like, "Okay, I have this like vague hunch.
29:14
I think that there's something here."
29:16
That's part for the course. Don't worry about it. It's standard.
29:20
Once you start exploring a new idea, a new topic, your ideas are going to be largely mistaken.
29:26
They're going to be halfbaked.
29:28
You don't need the perfect idea at the beginning.
29:30
That's not what you're going for.
29:31
All you're going for is a starting point.
29:33
And once you have that, you can reread what you've written.
29:36
And time and again, just ask yourself, is this correct? Is this complete? Is this correct? Is this complete?
29:42
You'll notice a big theme is that first draft.
29:46
You just need the initial moment of inertia.
29:49
And it is that constant process of editing where PG isn't just thinking about those little hiccups on the road that you're reading that I was talking about earlier where you're sort of nicking with the highlighting pen, but you're also asking, is this correct? Is it true?
30:06
Is it is this correct and complete? Correct and complete.
30:11
And then you can think about your shower thoughts.
30:14
Everybody knows that trope.
30:14
Like what you're thinking about in the shower, that's where you come up with your best ideas.
30:18
There's something about the way that your mind wanders that helps you be generative. No doubt.
30:22
There's a kind of thinking that you can only do without trying.
30:26
And it's when we find the peripheral ideas.
30:33
That's when often we make these big discoveries.
30:36
You think of the parable of Newton.
30:38
He's sitting under the tree.
30:38
The apple falls on his head, comes up with a big idea, and PG goes even further.
30:42
He says it's hard to do a really good job on anything you don't think about in the shower. Huh. Okay.
30:50
That's how much he values this that sort of peripheral thought.
30:55
But here's what's strange.
30:59
He talks about how you can't exactly control what you think about in the shower.
31:02
Like when your mind takes the reigns and it just walks to the march of its own beat, it ends up in some strange and unexpected places.
31:12
But then those are the things that you should be writing about.
31:16
The things that are actually on your mind, not the things that you wish were on your mind.
31:20
The things that you're actually interested, not the things that you think you're going to look impressive for being interested in. I see it all the time.
31:28
A lot of writers get stuck because they write about what they think they should be writing about instead of what they actually want to write about.
31:36
It's like they write about their boardroom thoughts.
31:39
Like, what am I thinking about when I got my suit, my time on the 38th floor, the CEO of the company is there, my boss is there, I really need to impress them. Sit up.
31:47
Say what you should say in this moment.
31:52
Don't write about those things.
31:52
Just write about your shower thoughts.
31:54
And if you do that, you know, we're talking about the strange places that your mind goes.
31:59
You just have a nose for outrageous ideas.
32:00
PG says, "I love questions that seem naughty." Naughty in some way.
32:05
For example, by seeming counterintuitive or over ambitious or heterodox. Ideally, all three.
32:17
And in order to do this, you got to get comfortable with playing with ideas that other people would just reject for either seeming pointless or maybe even politically incorrect to talk about.
32:27
like, "Hey, you're not supposed to go there.
32:29
You're not supposed to go there."
32:31
One of the things I do, and PG does the same thing, is I spend a lot of time thinking about who are the people in my life who are the most generative.
32:37
It's not about talking to a lot of people.
32:41
It's about talking to the kinds of people who help you have new ideas.
32:43
For PG, that's uh Robert Morris.
32:46
He's one of the co-founders of YC.
32:48
He's credited at the bottom of so many of his essays.
32:50
And there's something about the way that his brain works with Roberts where he ends up finding a bunch of new ideas.
32:57
And here's the thing, it's not necessarily about talking to somebody smart.
33:02
It's about finding people who are generative.
33:06
People who are generative tend to be smart, but not all smart people are going to be generative.
33:11
Who are the people in your life who are generative?
33:15
Who are the people in your life when you talk to them, you leave with new ideas? You leave with energy.
33:19
You leave with new ways of seeing. for PG. That's Robert Morris. Who is it for you?
33:29
And it works the best when you can just explore.
33:31
Like you don't need a complete thesis in order to start writing.
33:33
You just need some kind of gap, some kind of wedge that you can follow so that then that idea can expand.
33:40
You don't even need answers.
33:42
Sometimes all the edge you need is a question, an interesting question about something that other people take for granted. just a question.
33:51
And like sometimes that interesting question that gives you an edge, he says, "Speaking of edge, professional traders, they won't trade unless they have one.
34:03
Maybe it's a convincing story about why they're more likely to make money than lose money with this trade."
34:10
and the equivalent for writers for you and your writing where what you can do is you can say I'm going to approach topics where I' have some sort of edge in terms of some new insight or some way of approaching it and over time I'm going to cultivate my taste for writing topics my taste for writing topics that are interesting to others fascinating to me shower thoughts where I have an edge There's a guy named Jim Simons.
34:43
He founded Renaissance Technologies, the number one best performing investment firm of all time in terms of year-over-year returns.
34:51
More successful than Warren Buffett. This the founder.
34:56
And what's so interesting about him is that he wasn't the best at maths, wasn't the best at trading.
35:04
What was his unique skill?
35:04
Well, there's this New Yorker profile about him and it says that he has excellent taste in picking problems.
35:14
Excellent taste in the most interesting questions to ask.
35:19
Sometimes you don't even need those answers before you write a piece.
35:20
It's just what is a really interesting question.
35:26
So with Simons, here's the backstory.
35:28
What he ended up doing was he founded a informal conference where the whole point was to bring people together to find projects that weren't being funded by other sources. So how did he do it?
35:39
Well, what he did was he brought in a bunch of really smart, well-informed people and then brought them all together to speak and then would make a gut decision.
35:47
And here's what Simon said.
35:50
Taste in science is very important to distinguish what's a good problem and what's a problem that no one's going to care about the answer to anyway.
35:56
That's taste and I think I have good taste.
36:04
And I think PG would say the same thing for questions.
36:06
You know, he recently wrote a piece where he was talking about the importance of questions and he ends the piece.
36:12
It's called the best essay and he says, "Well, how do you find good questions?"
36:16
Well, that is the most important question of all.
36:21
And one way to think about it is looking for maximally surprising ideas.
36:26
Maximally surprising ideas.
36:26
He's like maximally surprising.
36:28
That is something, a compass, a feeling that you want to shoot for in your writing. So what's a surprise?
36:34
He says that a surprise is something that not only didn't you know, but that contradicts something that you thought you knew.
36:44
And it's a good sign when people are laughing or chuckling while reading a draft of something that you wrote. But why is that? Why is that?
36:53
You're aiming for good ideas, right? Good ideas are serious.
36:57
And the answer is that surprises make us laugh.
36:59
Surprises are what you want to deliver because laughter, I love the Tom Stoppard line on this.
37:03
He says that laughter is the sound of comprehension.
37:07
So once somebody has that moment of epiphany, they laugh.
37:11
And if people are laughing, there's an element of humor through the wit, the wisdom or the insight of what you're saying. It's like, whoa.
37:17
That's how you know that you're on to something.
37:19
So then what you should be doing is you should just focus on things that surprise you.
37:27
And then you're like, okay, I'm going to focus on things that surprise me.
37:28
I'm going to trust that in my first draft.
37:32
And then like we were talking about earlier, if you need a fail safe, just ask your trusted friends.
37:35
Ask them to read drafts of what you've written.
37:37
If they think it's boring, cut it.
37:38
But use yourself as a proxy for the reader.
37:41
And PG says you should only write about things you've thought about a lot.
37:45
And anything you come across that surprises you, somebody who's thought a lot about the topic will probably surprise most readers.
37:55
So let's take a step back. Let's reflect.
37:58
That means that there are two ingredients for great writing.
37:59
The first is a few topics that you've thought a lot about.
38:04
And the second is some ability to discover what's unexpected and surprising about them.
38:09
And when you have that something that's unexpected and surprising, that's when you have insight.
38:15
That's when you have interestingness.
38:17
And yeah, that means being a little rebellious.
38:18
PG says, "Don't do as you're told.
38:20
Don't believe what you're supposed to and don't write the way that you're taught to in school." And this is me now.
38:26
Remember, look for things that are general and surprising.
38:31
But know that general and surprising doesn't always start off looking like a big breakthrough.
38:35
All you need, you don't need like force equals mass times acceleration or like some big insight like that.
38:43
That's not what you need at the beginning.
38:44
All you need is like a little wedge, a little wedge, like a little specific idea, tiny insight, an intriguing question, something that you just can't stop thinking about.
38:54
You're messing around with it. You're playing around.
38:55
And then you're trying to sort of take that insight.
39:00
You're trying to kind of expand it, right? You got the wedge.
39:01
You're trying to expand it into something that's general and surprising.
39:04
And once you find that, boom, let it rip. Foot on the gas, baby. Go all in.
39:10
Lesson number five, try painting. Try painting.
39:13
Well, PG's book is called Hackers and Painters.
39:19
And that's a good way to think about his writing, too.
39:21
So, he went to an art school in Florence.
39:23
He went to Risie, the Rhode Island School of Design.
39:26
Ended up dropping at both of them.
39:27
and he did a bunch of still life painting. Bunch of still life.
39:29
You know, you got a fruit, you got an apple, an orange or something like that.
39:33
You're just looking at it. You're trying to paint.
39:35
And this is going to be the longest quote, but I think it is so revealing of how painting can help you see and how seeing leads to great writing.
39:47
He says that in everyday life, we aren't consciously aware of how much we're seeing.
39:53
Most visual perception is handled by low-level processes that merely tell your brain that's a water droplet without telling you details like where the lightest or darkest points are or that's a bush without telling you the shape and position of every leaf.
40:10
This is a feature of brains, not a bug.
40:13
In everyday life, it would be distracting to notice every leaf on every bush.
40:17
But when you have to paint something, you have to look more closely.
40:21
And when you do, there's a lot to see.
40:24
You can still be noticing new things after days of trying to paint something that people usually take for granted, just as after days of trying to write an essay about something people usually take for granted.
40:35
And I notice that all the time that when I write things, I end up seeing things that have always been in my field of view that I've just never consciously realized.
40:49
And that's why so much of good writing when you're reading something, the reader, you as the reader, you're like, "Why did I like that piece?"
40:55
Because it made me see something that I've always known, but I never knew that I knew.
40:58
It was always there, but I could never put words to it.
41:02
You know, that's what painting can do for you.
41:04
Because painting helps you see.
41:05
And so much of good writing comes down to good seeing, not just with PG, but with so many other writers.
41:11
Robert Caro, biographer of Lynden B.
41:13
Johnson, one of my favorites.
41:15
When Caro would do interviews with people, he would sit down with the people who he was interviewing and he would ask, "What would I have seen if I was with you?"
41:28
And he'd do it over and over again.
41:30
He'd say, "What would I see? What would I see? What would I see? What would I see?"
41:35
And people would like, they'd get upset.
41:38
They'd get annoyed because he was asking the same question over and over and over again. What would I see?
41:44
But because of that, he would say he's writing about the Texas Hill Country.
41:49
There's a cabin and okay, maybe you have this like vision of like this wooden cabin in the Texas Hill Country.
41:56
But by asking people, what would I see?
41:58
He would get these details like there was no water, hot or cold, the bathroom ceiling, the panels were falling down, there's rats crawling all over the building, there's sewers backing up, the sellers flooded, the dumb waiters packed with garbage, the carpets were ripping.
42:15
Now you can feel this visual, this emotional intensity.
42:16
That's good writing and that's the kind of visual perceptiveness that painting gave po Paul Graham.
42:22
Now PG isn't nearly as descriptive in that way.
42:28
But I think that there's something to the painting that allowed PG to see because he's really observant.
42:32
He's so good at seeing something that other people have seen and getting to the core of what really matters here.
42:45
even in his oneliners for how to build a successful startup.
42:49
Make something people want.
42:51
That's just I'm going to see the thing and I'm going to synthesize the thing that everybody else knows but nobody else has synthesized and I'm going to turn that into a maxim or a mantra that's going to help startup founders.
43:01
Which leads me to lesson number six. Do hard things. Do hard things for PG. That's building VIA web.
43:08
That's going to painting school. building YC.
43:13
It's easy to look at somebody like him and think, "Oh, he must have just sat around in his office just thinking about ideas, stroking his beard."
43:23
But no, that's not how he did it.
43:23
He has a bunch of experience with startups.
43:28
He did all that work with the programming language, Lisp, sold via web to Yahoo, right?
43:32
All those sorts of things at YC.
43:34
constantly talking to founders, constantly talking to people who are at the cutting edge of startups, reading the YC applications.
43:41
And my bet, I think this pretty sure bet is that conversations with all those people led to the initial ideas behind his essays where what he would do is he'd have all these thesis and they weren't clearly formed ideas, but he'd say, "Okay, I have a little hunch about this.
44:06
Okay, now I'm going to go write about it."
44:07
And then he would be having conversations maybe in office hours with founders and person A, person B, person C, all these founders they come in, they got these questions.
44:17
How should I think about marketing for my startup? I'm 2 months in.
44:19
We have some initial traction and we're wondering if we should go to paid spend or build a sales team.
44:27
Okay, that's a question that a bunch of people are asking.
44:28
And now he's he's feeling like his answers, they're just not that good.
44:32
He doesn't have the language, the words, the clarity to express his ideas in a way that's going to help people. So what does he do?
44:37
He goes to the keyboard, he starts talking to people, goes to the keyboard, he starts writing.
44:42
And then if he follows that, maybe he finds that initial insight.
44:46
Remember the first draft won't be that good, but he's just looking for something that's surprising, that's intriguing, maybe the idea is top of mind while he's in the shower, and then he finds an insight that maybe even begins to make it more general.
44:56
And now we get to general and surprising.
44:58
And a lot of his writing is the fruit of conversations.
45:06
You can see it and all the people that he acknowledged in Hackers and Painters.
45:09
So, this is a little trick of how I like to learn about people's writing processes.
45:14
I'll take their book and I'll open up right to the end to the acknowledgement section and I will read who they do acknowledge, who they don't acknowledge.
45:21
Do they acknowledge their editors?
45:21
Do they acknowledge people that they worked with? PG.
45:24
It's a bunch of people that he worked with.
45:26
And he explicitly says that he poured poured over the ideas in the book with friends for years before he ever wrote it.
45:38
And doing hard things is how you get to that place. It's not a coincidence.
45:40
It's kind of obvious in retrospect, right?
45:45
This guy who was at the cutting edge of a bunch of startups at YC, meeting with thousands thousands of startups over the years.
45:56
He's the guy who had the ideas that then he just took the time to sit down, write an essay over and over again and then he becomes the guy who creates a lot of the language for how startups get built.
46:07
I'm not saying it was easy at all.
46:10
I mean, that must have been an insane amount of work.
46:13
Actually, I'm just blown away, truly flabbergasted at how he wrote these essays while building YC.
46:19
But it's a really good example of the quote from Naval Robocott where he says to write a great book you must first become the book.
46:28
And for PG to write a great essay you must first become the essay by doing hard things.
46:37
So if you're one of those people and you're like David I I hear what you're saying.
46:42
I know that I want to be riding a bunch.
46:48
I want to be writing a bunch, but I don't have the time.
46:55
I can't devote my whole life to writing. Well, PG didn't.
46:57
The fact that he was doing hard things that that gave him the the ammunition for the pieces that he ended up writing.
47:04
And then once he sat down to write, this leads me into lesson number seven.
47:08
He improved by cultivating his taste for great writing.
47:11
And that is our seventh lesson, to cultivate your taste for great writing.
47:18
People like to say that ah, you know, taste is subjective. Taste is subjective.
47:23
Oh, you know, you got your thing, they have theirs.
47:25
There's no such thing as quality.
47:27
But PG insists that's not true.
47:29
And PG says that you learn the hierarchy of quality once you start to get better at anything.
47:33
And if you're getting better at things, then it proves that the ways that you used to do things, they weren't just different, they were actually worse.
47:40
They weren't just different, they were worse.
47:41
like you've changed your ways because there are better and worse ways to do things.
47:48
And for PG, he saw this once he started copying the great masters in his paintings.
47:52
He would look at people like Rembrandt or Definitely Da Vinci and he looked at them and he's like, "Wow, these people are really actually better than me."
48:02
And what you're doing is you're trying to deconstruct what is the thing about their painting that actually makes them better.
48:08
what is the thing that little trick that they got going or what is the skill that they've built up over years and years that you haven't quite got to.
48:19
So once you do hard things, you then cultivate your taste for what great writing looks like.
48:23
And the more that you write, the more you really push to try to produce things of excellence, things that you're proud of, the better off you'll be.
48:30
And actually, you can just see at the level of a sentence, right?
48:33
Like you have two sentences and you can look at it, you'll be like, "This sentence is better than this sentence.
48:37
Okay, I'm going to try to do that.
48:38
But now, one of the things that I also do when I try to think, and this is a me thing, this is not a PG thing, but one of the things I try to do when it comes to my own writing is I try to find writers who do something really well and they just go all out on one vector.
48:53
So, I think of Gregory David Roberts and Shantam.
48:57
The lusciousness, the freshness of the way that he writes is intoxicating to me and I'm like, "Oh, I wish I could do that.
49:05
I wish that I could do that.
49:07
And the the more I read and the better I read, the better my taste for good writing is.
49:19
One of the things that I recommend is that if you want to refine your taste, what you can do is you can make a list of things that you love and hate. You can go to a museum. You can watch movies. You can read books.
49:31
And then just make a list of what did I love? What did I hate?
49:35
Like you leave the museum.
49:37
What are the five paintings that I love?
49:39
What are the five things that I hated the most? And why? And why?
49:44
And we're going to talk about this in a second with PG. But here's why.
49:47
What you got to get good at is trusting your intuition for what quality is.
49:53
Not getting caught up in what other people say.
49:58
Oh, some critic, some impressive person, some person who has a PhD.
50:03
It's not about what they think.
50:03
It's about what you think.
50:04
What is it that you actually think is of quality?
50:10
Which leads me to lesson number eight. To copy what you like.
50:15
Like just about everybody, you, me, all of us, Paul Graham got started with writing in school.
50:18
And it's so funny when you think about it.
50:24
He thought that fiction was like the highest form of writing because that's what his teachers focused on.
50:28
He thought then like these short stories, they were just the pinnacle of writing because they're used all the time when you're in a classroom.
50:37
And the reason that they're used is they're perfect for a classroom exercise.
50:40
Okay, you got four-page short story.
50:42
You can read it for homework that night or you can read it in class then do a quick reflection.
50:47
Short stories are popular in school because they're the best the they're the most congruent with how things work in school.
50:53
You got a little bit of time.
50:55
You have people who don't have big attention spans.
50:56
So, hey, we're going to read short stories.
50:58
So, he's like, "Okay, I'm going to copy that."
51:00
And then he became a philosophy major in college.
51:02
And he's like, "Yeah, these papers, they're wordy and they're need needlessly complicated.
51:06
It's like really hard to parse out what the main idea is, but like I'm Paul Graham."
51:09
And at the time, he's like, "This is impressive and I'm going to try to imitate them even though I find them confusing."
51:15
and he looks back on it, he's like, "What? What was I thinking?"
51:20
And he says, "To hell with the philosophy papers.
51:22
To hell with the short stories.
51:23
I'm only going to copy things that I genuinely like."
51:25
And in order to do that, you need to separate what you like from what you think is impressive.
51:31
This is what I learned from him.
51:32
That there's a lot of writing that you might look at and say, "Wow, there's a lot of work that went into this."
51:36
Or, "Wo, the author pulled off something really difficult."
51:39
But that does not mean that you like it.
51:41
And if you don't like it, you shouldn't copy it.
51:43
Don't copy something just because you think that you're supposed to.
51:49
And once again, here's another thing that PG learned from painting.
51:51
That he lives in Florence.
51:54
He's looked at all this art and he says, "You have to figure out for yourself what's good.
52:00
You can't be trusting authorities.
52:02
They're going to lie to you on this one." Okay?
52:06
So, you can't copy what is like high status to think is good. So, what should you do? It's easy to critique.
52:14
It's hard to give a suggestion.
52:14
He says, and I got a kick out of this.
52:17
I laughed when I heard this one.
52:21
He says that you should look into your guilty pleasures.
52:27
Look into your guilty pleasures.
52:27
There's two kinds of books.
52:29
The first kind is like you're reading something like Ulisses and you're on page 274 and you're like, "Wow, I'm such a scholarly or irrudite person for having read 274 pages of Ulisses. Look at me."
52:42
And those are books that you enjoy having read more than you enjoy reading them.
52:46
That isn't to say that we shouldn't read those books, but it is to say that we should be skeptical of copying them.
52:55
And then there's the second kind of book.
52:56
And these are things that you actually enjoy reading where instead of feeling impressed with yourself for read for reading, you're like halfway done.
53:04
Instead of being like, "Wow, I'm so proud."
53:05
You're actually like bummed and upset that you're halfway done with the book.
53:08
Darn, I want to keep reading this.
53:10
Those are the things that you actually really like.
53:11
Those are the things that you should consider copying in your writing because there's a kernel there.
53:17
There's something there that really resonates with you and you want to take that seriously. Don't ignore that.
53:20
And this leads me to the third trick here that the stranger and the lower status that thing is that guilty pleasure is that thing that you love that you want to copy, the more that you're probably on to something there, the more that you should probably look into that and begin to imitate there.
53:37
If you're interested in something that other people think, "No, no, no, no, no. That's boring. That's lame. That's low status."
53:43
Actually, go write about that. Go copy that.
53:46
Don't do not dismiss your own interestedness just because other people don't understand why you're so excited about it.
53:52
PG likes to ask, "What seems like work to other people that doesn't seem like work to you?"
53:57
And for him, he was writing school papers for his friends.
54:01
Like, he'd just do the homework.
54:02
There were these white papers that he would write.
54:04
and he enjoyed writing these papers for classes that he wasn't even taking. Loved it.
54:07
And his friends, they were like, "Yeah, sure.
54:10
You can go write my papers for me. No problem." So, he loves it. Other people dislike it. Boom.
54:14
That's something that for him is play to him looks like work to others.
54:20
And here's the equivalent for writing.
54:22
What is interesting to you but boring to other people.
54:25
What is interesting to you but boring to other people. Write about that.
54:39
Write about that interesting to you but boring to other people. And then write briefly. Be succinct.
54:47
But now that doesn't mean short.
54:47
I always think of it like a standup comedy bit.
54:51
Good bit, good Netflix special, hour 15, hour and a half, but it has all these 30 to 90 second story loops.
55:01
Open up a story, close the story loop, open up a story, close the story loop.
55:04
And each of those sections, those are succinct.
55:07
There's not a lot of wasted words.
55:08
PG says, "Say what you mean and say it briefly."
55:10
But brief does not mean short.
55:13
Those are different things.
55:14
A lot of his essays are long.
55:17
And now this is speculation.
55:17
PG says that in the world of software engineering, when you make code shorter, it often makes it more correct because it gets rid of conflicting assumptions. They're just gone.
55:28
And I got to wonder how true that is for writing that the shorter definitely the shorter something is the easier it is to see the moving parts.
55:38
And then when you can look at those moving parts you could say okay what's going on here? What's good? What's not so good?
55:42
But I think that that's an interesting thing to reflect on which is if shorter is more correct in code when is that true for writing?
55:56
Which leads me to lesson number nine.
55:59
Don't try to develop a personal style.
56:01
So PG goes to art school and there's a bunch of painters who want to develop a personal style and they're like, I want to be like Picasso where you can look at a Picasso, you can instantly know it's me or the colors of a Saison painting or like the light in a Rembron painting. I want to have that.
56:18
And PG is like, no, that's just stickick.
56:20
That does not sit well with me.
56:22
I'm not going to try to cultivate that consciously.
56:26
And PG says that if you just try to make good things, you'll inevitably do it in a distinctive way, just as each person walks in a distinctive way.
56:33
Like Michelangelo was not trying to paint like Michelangelo.
56:38
He was just trying to paint well.
56:40
And he couldn't help but painting like Michelangelo.
56:44
The only style worth having is the one you can't help. The one you can't help. Just do that. Just try to write well. Try to write truth.
56:52
Try to take all the lessons that we've learned today and just focus on that.
56:56
The style will emerge just as the way that you walk will emerge.
57:01
It's not even something that you need to consciously cultivate.
57:05
And that leads me to my final lesson.
57:08
PG's final lesson that when an ending appears, grab it.
57:10
Learn to recognize the approach of an ending and when one appears, grab it. So there we go.
57:16
Those are the lessons for Paul Graham.
57:20
Number one, write simply.
57:22
Then know that great writing comes from great editing, that writing generates ideas.
57:26
Look for ideas that are general and surprising. Try painting. Do hard things.
57:31
Cultivate your taste for great writing.
57:34
Don't try to develop a personal style. Copy what you like.
57:38
Write briefly and grab the ending when it appears. Hope that was fun. I enjoyed doing that.
57:46
And uh we'll do this again. Thanks.
57:50
Hey, thanks for listening to the episode.
57:51
As I promised, I'm going to share that Sam Alen clip with you.
57:54
What did he learn from PG?
57:56
Remember, he was the president of YC.
57:58
Worked really closely with with him.
58:01
And I asked him, what is it that you learned from PG about communication?
58:06
But before I get there, I want to tell you one more time about the right of passage boot camp.
58:09
The next one starts on April 8th.
58:11
And I would love to have you if you feel like listen to this episode, you want to get after with your writing.
58:17
That's what this is all about.
58:18
You you're like, "Hey, I got an idea that I need to share.
58:20
I have some story that I need to tell.
58:22
I have some message that I need to spread. I want to write.
58:26
I want to improve my writing.
58:26
I want to improve my ability to communicate and articulate ideas. That's what I'm about. But I need some help. Well, then come join us.
58:35
Come join us in the boot camp.
58:37
You can sign up at write a passage. com.
58:40
And now, as promised, roll tape.
58:45
What got you to start writing the personal blog?
58:47
I wanted to like practice writing.
58:49
I mean, I had this like sense I had watched Paul Graham, write and he's an amazing writer.
58:52
I never had any aspirations that I was going to be anything like that, but I I had seen how powerful it was for helping startup founders and for getting to invest in good startup founders.
59:03
Um, so I wanted to get I wanted to like try to get good at it.
59:08
Did Paul Graham teach you anything specifically about writing?
59:12
Yeah, mostly just by reading his essays.
59:13
I think like many other people, my introduction to the startup world and excitement about it came from reading PG's essays.
59:19
He's like an unbelievable writer and that was a topic of like great interest to me and many other people.
59:26
Um I think a whole generation of us like copied PG in all of these ways.
59:32
Uh, and so although he was never like, "Let me teach you a class on how to write," I and others clearly took a lot of inspiration cuz I think he just does it in a style that resonates so much, clarity, precision, density. Yeah.
59:49
Like if you go read average business book versus PG essay, it's like they're both business writing, but other than that, they're like different species. There's no posturing.
1:00:00
He says interesting stuff. He says it clearly.
1:00:02
He doesn't waste your time. Nothing feels fake.