Packy McCormick: A Tactical Masterclass in Online Writing

What makes for a good title, thumbnail, first sentence? Born to Tell Dad jokes. I'd like a good pun. The goal is I want this to be the best piece that's ever been written about this company. I want people to be able to understand what they do in a way that they didn't before. The comment that I get from people after I write a deep dive in a company most often is like, "Finally my mom understands what I do." When you wrote the Great Online Game, did you expect that to break the internet? Today's guest is Packy McCormick, who writes a newsletter that's called Not Boring, and somehow some way he was a student in my very first Write of Passage cohort. I have watched this guy grow from publishing his very first piece to now how he's developed a sense of style using his wit, his humor, his love for dad jokes, bringing that all together to write about tech in a fun and vibrant way.

If that's something that you want to do, you want to think through, "Hey, I get really into topics and I want to write about those pieces. Hey, I want to develop a voice in my own work. I want to be thinking about how do I actually build a business around writing? How should I be thinking about subscriptions and advertising?" Packy's your guy. So if those are things that you're interested in, you're thinking about in your own writing, you're really going to like this episode.

All right, Packy, this is going to be a trip down memory lane. We go way back to the days

when you literally hadn't written anything and I was teaching Write of Passage in my bedroom. But one of the things that you've become a master at is packaging ideas, packaging pieces. So I want to start off by talking about how you think through the synthesis of a title, a thumbnail, and the first sentence. So I think this is going to be a good kind of preview for the whole conversation where there's a lot of things that I think maybe look like there's a bunch of thought, and I will literally, the last minute before I hit publish be like, "Oh." Every time I start writing a piece, I have a title up top, and sometimes it stays, because sometimes the title is almost like why I want to write the piece. I'm like, "Oh, that's a really interesting idea and a title." And so I put that up top. And then in brackets beneath it, I put, "Title image." And then I write the piece. And then I write the piece. And we can go into

the process and it's gotten uglier actually over time, the writing process. The last thing that I do is I'm like, "Did I make a good image? Do I need to go to DALL-E? Do I need to do something?" Hopefully I've drawn something that works as a title image, and then we'll throw that in as the last thing once I've finally written the piece. But yeah, it's a messy, messy process. What makes for a good title, thumbnail, first sentence?

I think what makes for a good title is... I mean, I was born to be a dad, and I was born to tell dad jokes. I like a good pun. I think if it can convey the idea, but be kind of fun and catch somebody's attention, that's a good title. The good thumbnail image, I think for pieces, and maybe it's because Twitter throttles links and I don't put them in there as much, I actually think that the more attention grabbing thing on Twitter is a really good bar chart or a really good chart of some sort or a really good number is what you'd want to actually put in the original tweet. I think the thumbnail is probably less and less important, which is probably why I put less and less time into it. Because before, if I could put the link in and then the title image would show up in full in the first tweet, that really matters. I think it matters less and less, and I think finding the shocking stat or shocking visual thing is a good thing to put in the thumbnail image.

Actually, I don't think I'm particularly good at the first sentence. But what I like to do is I will spend most of my time writing an essay on the introduction, on the first few paragraphs. The way that I think about and describe it is, if you're skiing a fresh run, figuring out your line ahead of time is really important. Once you figure out your line,

you just kind of go and you're going through the piece. So if I can figure out how to frame the thing, all the other sections kind of fall into place where I'm like, "I'll need to describe this if I'm talking about this. And here's a definition of a thing that I'm talking about, so I need to describe that word, that word, that word, or I'm saying this company does X, y and Z, I better say why the way that other people have done it doesn't actually make any sense anymore, even though you might think that the way that people do it will be the way that people always do it." And I think I establish as much of that as I can in the introduction and the rest of it kind of just flows from there. So that's an interesting analogy, so I'm going to follow it. We'll see if it's what the implications of it are, right or wrong. So what you're saying is that a good introduction, I was sort of applying that it's a hook.

What you're saying here is you're basically plotting your direction, plotting your arc, and it's both for you as the writer so that you can get momentum, but is it also for the reader that they can begin to see where they're going? Totally, and I think I could actually do a better job at both hooks and letting readers see where they're going. I think there's a lot of things that we talked about in Write of Passage or that people talk about generally, like write short pieces, let people know exactly what's going on up front. And I could probably get a lot better at that. I think it's more like I want to figure out the right interesting path through this piece, and I hope I help people up front with that, but I really try not to be hyperbolic. And there's maybe some sort of embarrassment if I'm trying to get too hooky in the beginning. And so I really just want it to be like, what's the most interesting way to tell this particular story that nobody's

told it before? I think that there is a lot of... I started thinking about it as beta content and then alpha content, and there's a lot of beta in just like, "Oh, AI is going to change the world." Who cares? Everybody's writing that thing. If you read another piece on that, you're not going to get any smarter on it. But maybe in 10,000 words and hopefully in the introduction, I can change the way that you think about an idea just enough that if you're not going to remember exactly what I wrote in the piece, but maybe it'll just shake something loose in your brain so that you think about the world in a little bit of a different way, or you're maybe a little bit more optimistic about something, and you think it's a little bit more likely that a thing like this might happen. And so I'm more going for that than like, "Oh, man, this is the hook that somebody is going to keep reading for." Yeah, I got this from Sam Parr when he came

on the show. He said that what works really well on the internet is these barbell pieces.

So there's some short pieces that say are a few hundred words. And I think of those as something that would be a screenshot essay or a little bit longer, right? Like a Seth Godin piece, right? There's a shortness, a compression to it. And then he said more than 2,000 words. And I like that way of thinking about it, because also that's sort of how my brain works, where I producing these short little bits, almost like a comedian. It sort of would be as long as a TikTok video or something like that, sort of in that screenshot, it's like, here's an idea that I can share. Sort of the pieces that Chris Dixon was writing for years, three or four paragraphs, one main idea, and it's just right to the point. And then on the flip side is the definitive take on something. And you do a good job of this, Mario Gabriel does a really good job of this, these long form pieces where you're basically throwing in the mic down, you're saying, "I really thought through this.

Here you go." And there's something about the middle where it doesn't quite work as well. I mean, every time I write a piece on a company, the first time I thought about it this way, I was writing about companies in the beginning that were either public, and so I just wanted a different way of looking at them, because I knew I wasn't going to be as good at analyzing a public company as the analysts who spent all their time thinking about it. But I was like, "What if you think about the company in this type of metaphor?" So that was one.

But when I started writing about private companies, and Stripe was the first one where it was like everybody's talking about Stripe, what is the thing that I can write about Stripe to make this the best piece that has been written on Stripe to date? And I think Mario has since written a great one, and Burn has since written a great one. So it might not be the best on the internet anymore about Stripe, but at the time it was definitely the best on the internet about Stripe. They would give it out to new employees when they brought them on board and all of that.

And so that is the goal whenever I write about a company. Still, whenever I write about a company, the goal is I want this to be the best piece that's ever been written about this company. I want people to be able to understand what they do in a way that they didn't before. The comment that I get from people after I write a deep dive on a company most often is like, I'll get employees at the company emailing me or the even, and say, "Finally, my mom understands what I do."

Which is cool, because I think it says a few different things. One, I'm writing about the types of companies that actually aren't that easy for the mom to understand what these people do, and those just, they've attracted me even more and more over time. But then two, my job I think is to be the kind of dumb guy, and I don't mean this to be self [inaudible 00:09:05] but the person who really needs to actually figure this out alongside the audience or just before the audience did and explain it in a way that a regular person can. And I think if you're too smart or too deep in an industry, it's hard to do that. But I'm just dumb enough that I can go into a new topic, a new company, a new space, and really just try to do all the research and work, and then put as much of the, "Here's what I'm learning as I learn it, and let me try to describe in a way that helped it click for me that I've possibly gotten." So that's a little bit of the goal with those.

One of the things that I've taken from comedians is, and this comes back to introductions, is how good they are at setting the scene quickly. So someone might say, "I was on a bus and all of a sudden there was a fire." Okay. That is not a good example, but you get the point, right? And what, it's like nine words and all of a sudden we have conflict, we see the scene, we understand what's going on, and if it was a comedian, they would say it way funnier than I just did. And in the Mario Gabriel piece on Stripe, his first sentence I think is, "What if Romulus and Remus had gotten along?" That's so good, because now you see it's a story about two brothers, a story about power and ambition and boldness, and you see that, okay, there's going to be a human component in this piece. Just one sentence, and you've set up that whole scene.

He's a master at that. I mean, I think talk about, I start out every one of my newsletters with, "Welcome to the X number of new smart curious people." And I think that I have a smart, curious audience of people. But talk about respecting your audience and the way that Mario does where he's like, "Oh, yeah, people are going to understand exactly what I mean when I say imagine if Romulus and Remus had gotten along." That's incredible. Yeah. Well, this is why I think that the big advantage that we have as online writers is the hyperlink, because what the hyperlink does is it allows us to embed context in a little blue text with a little underline, and we can say, "Romulus and Remus, okay, go read that on your own. Go read that on your own." And so much of what you're doing when you're writing is you're putting out into the world content ideas that then are going to attract a certain kind of person. And when you treat your readers like they're smart in that

way where you say, "What if Romulus and Remus got along?" And you don't take the time to explain it, you just say, "You're going to know what this is." Like Byrne Hobart does a great job of this. You're like, "I feel smarter when I read Byrne Hobart." It's like, "Ah, I've been invited into the esteemed legion of Byrne Hobart readers with The Diff." And you can do that, get those smart and curious people by using hyperlinks really well. Totally. Yeah. I'm always curious to see what the most clicked on link is going to be in a piece. And sometimes I'll embed a YouTube video, and that just ends up being, because everybody wants to hit the play button. But sometimes it'll be a link to some explanation of something that's like 2,000 words in a piece, and I'm like, "That was a good piece." If they're 2,000 words in trying to keep understanding what's going on, that is a really good piece. How have you gone about cultivating your

voice? One of the things that's happened is I think you use less pop culture references

than you used to. But when you started, you didn't have nearly the voice that you have now. And what's interesting is you have a very digital, modern contemporary voice, and it's distinct. How did you go about doing that? I mean, well, we'll do the Write of Passage plug here. I mean, I think more than any technical thing, I think the biggest idea that I got from it was the idea of the personal monopoly of finding the intersection of a few different things that you care about. And so I was incredibly on the nose about that. In the beginning it would be like, all right, there's going to be jokes, pop culture, business strategy, technology. I remember thinking specifically, and I've said this before, but I remember thinking specifically like, "Ben Thompson does the thing that I want to do, but he does it so well that there's no chance that I'm going to do that, but what if I counter position against him? He's never going

to be as silly as I am in the newsletters. He's like not going to write about maybe some of the weird topics that I write about. He's certainly not going to compare creative destruction to the Mickey Mouse Club. And so what if I do that and just really lean in hard to that?" And so the first 10 full essays that I wrote on Not Boring were, here's a pop culture thing, and here's how it's a thing that's happening in business or technology. Over time that really became like thinking of two essay ideas at the same time, where there'd be some really interesting things to write about in tech and business that I couldn't think of a great pop culture analogy for, but I still wanted to write about. So over time, I dropped that, but I wanted to keep kind of the fun, fresh, different voice that I had in the piece. I think frankly, maybe my voice has gotten a little bit more consistent, just obviously from writing hundreds and hundreds... I've written over, I've published over a million

words pretty easily at this point. And so it's probably developed just based on repetition. But I do also think that I need to start reading some more of my old stuff and get a little bit of that freshness and a reverence back. There's something weird that happens where in the beginning I was writing as a total outsider. I was writing about public companies. I was writing about people that I'd never met in my life, about categories that I'd never said anything about before. And now I'm writing about companies that I know well and maybe have invested in, certainly know the founders of, don't want to say anything mean about. And so I think maybe it just... And certainly there's also probably a, I know that when I've said something like this before, I've gotten dunked on for it. And so there's definitely a little bit of the defensiveness in there, a caution that I need to figure out how to remove. Oh, I feel you, man. I mean, the way that I was

thinking about what you just said is that when you first start, there's you. And it's timid you, it's scared you, it's, "Ah, I've never done this before." You. And over time, what's nice is that you becomes a little bit more confident. You're now, like, "Ah, people have read my stuff. That's a good thing." But the problem is there's a second character that emerges, and that is the caricature of who you are, and that is your perception of who you are and what people expect from you, and oh my goodness, who is Packy on the internet and who is Packy in real life?

And so now they're these two characters who are playing together. I'm like, "Which one is supposed to be driving the ship?" I mean, I guess the caricature, there's probably a utility to this caricature. But then it actually begins to limit the real David, and the real David is evolving, the real David is growing, and then the caricature says, "No, no, no, no, no, don't change this. You're the writing guy. You need to focus on this." And there's this tug of war that emerges over time. Yeah. No, I've been really proud about being very willing to shift topics or write about completely different things from week to week, and try not to become too much of a thing. I think there is a thread of optimism, but that is very much who I am and how I see the world. So that doesn't feel faking anything. But there just is... So I wrote a piece this week and I used a phrase that I'd heard from a founder that we'd spoken to that

I really like called cost physics. And I used the word in the piece or used the phrase in the piece, and then I was actually going to write a whole another piece, and might still do this, but write a whole another piece on the idea of cost physics, because I went and Googled it, and it wasn't a term. I went on Metaphor to look up other blogs on whether people had written about cost physics. Not a term. And did all these different searches. Finally, I did Twitter. And the first thing that comes up was essentially some anon account being like, "Cost physics, like what the fuck is this?"

And making fun of this thing, and saw this thread, they're making fun of this idea of, oh, look, VCs rediscovering manufacturing. The whole thing. Now I'm like, "Do I write about cost physics or is it dumb?" And I think it's a cool way of describing a thing that people might or might not think about, and so I'll probably still do it. But now there's this little like, "Oh, is this idea dumb?" In the back of my head that just wouldn't be there if nobody read my essays or cared about it.

Yeah. One of my favorite sentences that has been uttered on how I write so far is Kevin Kelly, a piece of writing advice where he goes, "Just tell your story with uncommon honesty." And I'm like, "Yes, that's what I want go for more and more." Is first of all, I need to figure out the truth for myself. I think it's Robert Trivers, he has this paper from the 1970s where he basically says that it's a feature, not a bug, that we deceive ourselves. And we deceive ourselves in order to protect ourselves. So the first thing is, what do I actually think?

How do I actually tell the truth to myself? And that's actually most of the work. And then the second thing is, okay, now that there's layers to the truth, how do I take that truth and with courage and conviction, put it onto the page to get that uncommon honesty? And if I can do that, I'm consistently surprised by how much it resonates. And I'm like, "Wait, what? That was the easiest thing ever. All I need to do is just talk about what happened."

Totally. Yeah. I see that all the time when I try to overthink something or over intellectualize it or sound smarter than I am, it comes across as flat. If I'm like, "All right, I'm excited about this thing." How do I get this excitement on the page without actually being so excited that people are just like, "Ah, he's just being excited about something again." But yeah, how do you get the genuine feeling that you have and the genuine way that you think about something? There's so many things in the world to write about. If in a week I'm choosing to write about something it's because I think it's one of the more fascinating things that I can think about. It's like, how do I get the fact that I think this is fascinating enough to write about, not perfect, not going to change the world inevitably, but one of the most interesting things that I can be writing about right now, how do I get that excitement, what got me interested in

the thing in the first place down onto the page? And talk to me about that feeling of excitement. What is that like when you're at the keyboard? How does that manifest itself? I'm at my desk, I'm sitting there, I'll get an idea. The first draft is never going to be good, but I just try to write a version of that draft while I'm still excited. I remember from Write of Passage the just write as much as you can, don't do any research, don't edit yourself. And I don't do that. I come to a new idea as I'm trying to do that. I start doing that, I start writing, I have the excitement, and I'm like, "I don't understand that, so let me go and research that thing so I understand it. Oh, this is actually the ties to this." So I'll download a book on the Kindle and reread it. And so every essay is a week long kind of process. If I'm lucky, I have the full week. Otherwise, I try to condense a week into four days of getting excited,

finding something that I need to research a little bit more, researching that thing, realizing like, "Oh my God, there's so much information here that I actually don't know how I'm going to condense it all into a thing. What have I gotten myself into?" Then get excited again. Then write. And then go through that process over and over and over again. And what the process actually looks like is, and what I've been doing recently is I open up a Google Doc, do the title, title image, start writing, do V zero is the first one, because I know it's just going to get scrapped and I'm going to use that as the doc where I dump all of the stuff that I cut from the other versions.

I've been going through six versions where I'll write it, I'll find a good section, or keep the introduction, find another good section, but completely start fresh and start fresh in a new doc, not try to edit myself at all. I'm like, "All right, I'm just going to try to capture that excitement and just start typing again." And that won't be it. So it's almost like if I find the ski run, I get to a spot where I just hit a wall and I'm like, "Oh, this is actually not the right path." And so I need to go back to the top and just start fresh again. And so I'll do that.

Wow. So you will go and you feel like you've done it wrong, and it's almost like you're doing a maze, and you go all the way back to the beginning and you try again. Yeah. Really? And as I'm doing it, I think I understand what I'm writing about a little better each time, and so I can go to the top of the maze and be like, "Okay, cool. I actually think this path might be the right one." There's definitely, and this is not an uncommon thing, there's nothing special about me here, but some sort of deadline really, really helps, and it just kind of all comes together and I can say it better when the deadline is approaching.

How that's manifested recently though is I will work on something for four days. I'll write six or seven drafts of the thing, and then invariably, 4:30 the morning that I'm going to hit send, I wake up to maybe edit, maybe rewrite, rewrite the whole thing from 4:30 to 8:55 AM. And there will be, it's not just completely fresh, and this is not for if I'm writing a deep dive on a company where I've spoken to the company a bunch, I've done a lot of research, I know the angle, those are going to be set in place a couple of days before, and that'll be editing at the end.

Or the other pieces, I think at the last 10 essays that I've written, I've rewritten at 4:30 in the morning, under the gun, texting my brother. We have sponsors in the newsletter, so texting Dan who's been running ad sales but is now focusing full time on his business, but texting him, being like, "Do you think sponsor X would mind if we sent tomorrow?" And racing and then texting him at 8:30 being like, "All right, actually I think we have something. I'll send it, we'll throw the copy in there." But that's been how it's been going, and I don't know if that makes the essays better and more raw. I don't know if it makes them worse. But for whatever reason, I need that amount of time pressure to get it done recently.

Wow. That sounds... My heart is beating so fast right now. I don't even know what to say. That sounds so intense and struck with panic. Just a little. I've gotten better at not panicking, just I guess again, from repetition. I'd been spending, I mean, before the kids, so we

have a three-year-old and a one-year-old, before the kids, I would just like, morning to night, all weekend, whatever I needed to do to write the piece. And now I've tried to... And then I actually took that into having the kid. And so my wife, Pooja, would, it was the best, would be like, "All right, cool, I'll take them." I was like, "I don't golf. Pretend that..." My golf is writing. Pretend that I'm golfing right now. I need six hours. But I'm not going to be drinking beers with the boys, I'm just like, I'm sitting there and writing, I need six hours. But it would just bring the stress into the weekend where I'd be with my family and then I'd be kind of on edge. And everybody could, I mean, the kids couldn't, but Pooja could certainly tell, "You'd rather be writing right now than sitting here, because you had an idea." And so I've really tried to remove the stress from the weekends and just batch... I started sending on Tuesday instead of Monday, so I at least have

that day to run through some more drafts. But I've really pushed all that stress into the last four and a half hours from 4:30 to 9:00. Yeah, it's funny that you say that, because I felt the same thing. Early on, my weekends were almost the time when I worked the hardest. It was like I didn't have to worry about people. I remember Saturdays and Sundays, I would just read and read and read and then I'd have double writing time. It was like double jeopardy, but for writing. And I would just do it all day, and I wouldn't have plans and stuff.

And then now it's got to the point where I do not work on Sundays. I just will not work on Sundays. Sundays are totally different. But every week I'm like, "You know what? This week I might not do it." But something happens on Sundays where I'm like, "Nope, you're not going to work." But one of the challenges that I've had to face is I used to rely on procrastination as a way to get me going, and it's like, I can't do that anymore. Yeah, it's really interesting. So and you've had Byrne on, he's one of the big examples I have in my mind of people who just are, one, just next level smart, and then two, I think have frameworks about how the world works and the ability to hang new information into things as it comes up in a way that it doesn't sound like his process is easy. He's also waking up at 5:00 AM to write and does it every day, which I don't understand. But his value add is that his horsepower and the way that he thinks about the world is just so strong

that that's what he's putting on the page. Whereas when I'm doing it well, I think the thing that I can do is just be the guy who's more obsessed with figuring out more about this topic than anybody else. And so that time crunch makes me feel like I lose a little bit of that superpower, right? This is my Packy riff on who you are. So it's like a bunch of friends, you're sitting around the table, you're laughing, maybe you've had two beers, okay, for the sake of the story, two beers. You know that moment where everyone's having a good time, but when the food is there, you're kind of focused on the food and then the food is done, but everyone knows they're still going to be there for a while, and that's often when the conversation gets really good.

You're like the funny friend who just got really into something. It's like a fairly intellectual group. And then you go and you tell everybody else of what's going on, and it's like that thing where there's some interruptions in the conversation, but everyone's laughing and having a good time. And then you get after the dinner, you're driving home, you're like, "Man, I learned a lot. I learned a lot." That's sort of like what you do, but for writing.

I will take that. I've never thought about it that way, but I really like that. That's what I want it to feel like, right? One of the reasons that I started writing Not Boring in the first place, that I called it Not Boring was that I was like, "This is the most fascinating stuff in the world." There is sci-fi happening, there's this drama happening, but there's these kids and just geniuses who are building these things for people, and the way that it gets written about is so dry.

I think business strategy is so interesting. And I like Richard Rumelt's Good Strategy, Bad Strategy I think is a little bit better written. Obviously Ben Thompson's stuff is really, really good. But most of the time people read about business, they're like, "Oh, you're talking about business. Please don't talk about business here. We're trying to have fun." It's like, what are you talking about? This is some of the most fun stuff imaginable. And my job is to try to convey why I think it's so fun and interesting to people in a way that they're like, "Oh, actually this is kind of cool." Well, I think this is one of the reasons

that people like Elon Musk so much, that Elon is a grade A entrepreneur, say engineer, and then also he's a memer, and he's funny. And because you get the laughs, then when he talks about, "Hey, here's how you need to think about strategy in a production line." I'm like, "Well, I like this guy, because he's making me laugh all the time." And then he has a meme that I just saw, which just like Emmanuel Kant, Genghis Khan. That was very good.

So I'm sure you'll probably interview Walter Isaacson at some point, and so apologies in advance, I'm sure he won't listen to my episode. I really liked the Elon book. I thought the central question of the book, which was essentially, would Elon be able to do all of this if he weren't this kind of crazy person? It was just such a nonsensical question, because the answer is so clearly no. Those two things go together so tightly. And that's awesome.

We are so lucky to have people in the world who... [inaudible 00:29:04] I won't get canceled here, I think the Clintons had a great marriage. I think if you are two people of eight billion who want to get together because you want to achieve these outlandish things that nobody achieves, and you don't have the most loving relationship and somebody... Okay, what a great partnership you were able to find where one of you was president and the other of you almost became president. That is a success in what they were going for in that marriage. And so the fact that there are some people who live unconventionally and are willing to do this crazy stuff to try to do these big things, I think is wonderful. And I think that's such a silly question, because like, no, you need that Elon crazy. And net-net, what a positive thing for the world that exists.

You're talking about flow. What does that practically look like for you? Flow is getting five pages into an essay and being like, "Whoa, I wrote five pages." And then going back and kind of reading it and being like, "Whoa, that was actually pretty good. And that's kind of what I wanted to say." And then I guess the obvious example is that the Will Ferrell debate scene in Old School where he just blacks out and came to and had said something really good where it's like, "Whoa, I actually, I didn't think that I was going to write exactly this when I started writing this thing. And now that I look back, that was better than had I over intellectualize it and thought about the words too much, something that I wouldn't have written." And so flow is almost a thing that I realized happened after the fact if I've written something good that I hadn't gone into that writing intending to say exactly like that.

One thing that I've noticed is, so I really struggle to get into flow when I'm typing. I don't know what it is, I feel like I probably have some early onset arthritis or something. It's just like when my fingers are moving, even just moving my fingers now they feel like compared to other parts of my body, it just like my fingers feel... Can hear them crackling a little bit. All right, what's going on, right? I can crack my fingers easily. I'm like, "What's going on with my fingers? They're just tight." And so much of my writing has been a quest to still write, but use my fingertips less. And what I've discovered is voice translation and voice transcription. So Superwhisper has helped me where what I do is I just pace around the room or I'll go on a walk, and I then get into a flow. And I've noticed that my ability, the number of words I can write in a single session has doubled. Huh. Do you end up having to go back and

edit more or differently or take your chunks of ideas and write them in words that you- There is no doubt that I have to edit more. There is no doubt. But I think that what I lose in the accuracy of what I write, I gain in flow. And all I'm trying to do, I'm not trying to make a statue, I just need marble. And as long as there's a statue inside that marble, it's a success. What do you have going into your walk? Do you have an idea for something and you just riff? Do you have a structure already? Yeah, so the way that an epiphany manifests itself for me is a full body experience. And generally it's one sentence. So I'll give you one right now that is percolating in my mind. So I was just talking to Michael Mauboussin, and he likes to quote this paper from 1980 called, it's a mouthful, On the Impossibility of Informationally Efficient Markets, okay? Where it basically says the whole point is you can't have

efficient markets for information. You actually just, because there's a cost of collecting data. And I want to take that idea and apply it to writing for people who say all the ideas have been shared, and basically say there's this concept in finance, and if you follow the logic of that and then you apply it to writing, it basically, no, you're wrong. It disproves what you're saying. So I have that idea. I have the structure in my head. I have the first part, I have the second park, the second part. So what I'll probably do is I'll probably go for a walk in Central Park right after this and talk that out. And then what I like doing is I'll probably talk it out and then as I'm talking through it, I'll discover things as I'm doing right now and then I'll say it again and again, and every time try to compress what I'm saying. And then once I hit the third time, I'll usually have the structure, take that, airdrop on the computer,

type it up, and the piece will be done. And do you feel like a crazy person walking around? Yes. Yes. What goes on in your head? Do you think, "Oh, people will think that I'm having a phone conversation so they won't think it's weird." Or can you think that people will be able to tell? What I like doing is I don't do AirPods, because I've had exactly this, I'm like, "Oh, am I going to look like some crazy person?" What I do is I get my phone and I take the bottom of my phone, I put it under my mouth, and then it's as if I'm doing some voice memo or something. So it only makes me mildly crazy. Perfect. That's great.

What's a time where you feel like you were really in a flow? It's maybe not even as much on the writing side. The times that I'm thinking about, I wrote this piece on Tencent and I ended up turning it into a two-part piece. This was fairly early on when I had nothing but time. This was early COVID, I was at my parents' house, nothing to do. My mom would cook meals, so absolutely nothing to do. And I was like, "You know what? I think the portfolio of investments they've made is super interesting. It doesn't exist anywhere. And so I'm just going to get into the internet and go to Chinese language sites and find all the, and cross-reference things with each other, and find as much of Tencent's investment portfolio as I possibly can and put it into a spreadsheet." And that was two days worth of just digging and finding something that contradicted and then having to find a third source. But it just

felt like by the end of it I was like, "Oh, no, no, I know where all the different things are hidden here and I'm not going to fall for that bad data source again, because I saw that over here." And it was just a couple of days of by the end I woke up and I was like, "Oh my God, that was a ton of work to do in a couple of days. And now I have this cool document." And I think more than anything I wrote in that piece, giving people a link to a spreadsheet. I did this with Sci-Fi Ideas recently, which is a really fun project actually. So there's this great, great site technovelgy.com. Technovelgy.com.

Where this guy just takes all of the sci-fi and lists out line by line, this book in this year said this idea or had this idea for this technology. And then he'll go back and link new news sources to when that thing actually came true. And so I did a project where I took as many of those as I could. I copied and past pasted from the web page into an Excel sheet. I used ChatGPT to format the spreadsheet and get it into a place that was consumable. And then I used two different Anthropic accounts, because I would rate limit the Anthropic accounts back and forth trying to have them explain whether that idea had come true or not on this 3,000 entry list.

And it was the same kind of thing where it was two days and finally when I cracked this, oh wow, this thing is actually starting to work. And everything that it's saying makes sense. I remember just sitting in the room, it was actually at my parents' house also, with the kids, but they were watching them now, which was great, just flowing back and forth between Anthropic and then taking the sheets out and putting it in this spreadsheet. And by the end I was like, "Oh my God, this is a really cool resource." And people, I think I still see people sharing this sci-fi idea bank, but it was just a couple of days of like, I'm going to flow on this research as much as I can.

So this is a inside joke that we have at Write of Passage, me and my ops guy, he looks at the website analytics and the most repeatedly read piece is Why Did the Boeing 737 Max Airplane

Crash? Which is just so random, because that has nothing to do with anything else I've ever written. Nothing. But the thing that reminded me of it is I found this leaked memo from 2001, and I'm like, "This memo, this memo, people explains everything that's wrong with Boeing." And I found this memo, and I had to do this crazy thing to download it at the time, it was like 50/50, am I going to have all my money stolen from me or am I going to get this memo? I get the memo and I just read it and he just says, "This is what's going to happen. This is what's going to happen if we start outsourcing." And that's what begins to happen. The 787 is built abroad, the 777 is this and that. And there is a moment when you find some source and you're like, "Boom, boom, boom, we struck gold. Eureka, let's write." Yes. And people love when you've uncovered a gem for them for sure. So there's the two different things. There's, can I give people this source in

my writing and let them see it for themselves, and they've definitely never seen this before and it explains how the world works in a really interesting way? Or there's the, yeah, you're reading something or listening to something and you get a quote and you're just like, "That's exactly my... Thank you. That's perfect. I'm going to rip that in." Both of those discoveries are amazing. Another great genre on this tack is YouTube interviews a very successful founders before they were very successful when they're just unhinged and you can see how desperate they are for success and how singular they are as human beings. They're just weird. I uncovered this Stanford interview video with Mark Zuckerberg in like 2005, it's like a minute and 26 seconds long, and it's blurry. But I forget what he says, but it's very insightful. But it was one of those things where media trained Zuck would never say that, and that genre, those early interviews are really good.

I mean, Zuck had another, when was the Kara Swisher interview where he was in the red chair and just sweating profusely? Yeah, and takes off the jacket, the sweater, and then it's like some symbol in the sweater. Yeah, I feel like after that is when he got media trained, because he got ripped apart for that so badly and he's a public company

CEO. The other amazing video from that genre is the Jeff Bezos one. And that's been shared a million guys, but Jeff Bezos is talking about Amazon. Great, great, great video. Yeah. You mentioned Anthropic. How do you use AI GPT in your writing process? I use it to explain things to me. So I'll say, "Here's a phrase, explain this." And then I can ask a bunch of questions about it. I'll ask it general questions about the topic that I'm writing about or ask it to explain it to me in a different way, and then kind of just use that in the way that I'm thinking about the piece. I started using in the past couple of months. I use them as an editor. And I don't know actually how much I actually take the feedback. I think ChatGPT and Anthropic and Claude are both pretty bad editors in different ways. And so some of it is just sanity checking that I'm not crazy and having the AI tell me nice things about

the piece that I'm writing, because like... It is so complimentary. It's like, "Wow, this is a very thoughtful reflection on something." I'm like, "Thank you." Claude in particular. ChatGPT, it can be a little more crotchety, but Claude in particular is like, "This is, I mean, what a contribution to the field and blah, blah, blah, blah. It's an A. And with this one tweak, it's definitely an A plus. Among the best things ever written." I'm like, "Perfect.

That was exactly what I'm going for." And so there is a little bit of, as I'm going through these drafts, I'm like, I'm halfway through the piece, I'm like, "Man, I'm stuck here." It's almost how I take a break from the piece is like, let me just dump it in here, have it tell me nice things, and maybe it'll say, "This thing is confusing." Or I'll also ask it to tell me, and ChatGPT is actually better at this one, "Is what I'm saying here right?" Or, "Your job is to cynically attack this. Where did I get this wrong?" On things that I'm trying to explain. And it's actually pretty good at that. I think the danger there is to then not add a bunch of qualifiers afterwards like, "Oh, I'm saying this, but also I understand that X, Y, and Z." There is a balance between being balanced and having writing that moves and has a point of view and all of that. But it is nice to know if there are any bodies that I just wouldn't know about to run it through for that reason.

You know what else it's good at? It is a bomb thesaurus. A bomb thesaurus. So what I do is I'll take a sentence, copy and paste the sentence in, put quotation marks around it, and then I'll say, "Read the sentence I just wrote, change the word elegant. Give me 10 examples of the word elegant. And the emotional tenor of what I'm trying to convey is this." So good. Yep, I will do that with a blank. And so if I'm like, "I don't know the right word."

I don't even put the word in, "Here's the sentence, fill in blank." And so it'll maybe give me that word. And it's sometimes right, sometimes not, but it'll get close enough. I don't then use it as a thesaurus and ask for 10 different versions, but it'll at least jog my brain on what's the word that I should be using here? If what I'm trying to say is not obvious. You were talking about using DALL-E for images earlier. How do you do that?

I went really hard on it in the beginning. And I think there are some people who have their own distinct style. There's someone, Megs on Twitter, who has this beautiful, I think she calls it techno Elysian. It's like robots in flaring robes, and has really honed the style. There's some people who have their very own style where they run the same prompts and ask for different things but have the same in the style of, the same words. And so they've started building these universes. I love that. If you don't do that, I think you can end up looking kind of generic in Midjourney or DALL-E. And so in the beginning I was like, "This is awesome. I will never have to draw something ever again. I'm just going to ask for the perfect image." And sometimes the images are perfect and sometimes they're not, but they all end up looking a little bit alike and you could tell that they're AI generated.

And so now I use them a little more sparingly. I used one because I just had no time the other day when I wrote my piece to make the title image. And so I'll do that if I'm totally out of time and can't draw something, can't think of something more creative. But I think I probably went from having five or six AI generated images in a piece to maybe there's one now.

How do you think about the business model of what you're doing? You have the sponsored post, you have the investing. Talk to me about that. Yeah, so I have a couple of pieces on the business. I have regular sponsorship at the top of the newsletter. I do these sponsored deep dives, which are definitely the most unique, and more people have started doing them. But certainly the most unique, it's essentially it's sponsored content that has a bad word, but I try to make it the best thing that's ever written on these companies. Regular sponsorship, super easy. That's just what half the newsletters do, you either go subscription or sponsorship. I thought that I was going to go subscription. I think there's a few reasons that I didn't. One, I just loved the growth in the beginning and I was like, "If I start paywalling even half of my content, it's not going to grow as much. And so I don't want to do that." And actually it's growing

bigger than I thought. And so I can get to a big enough audience size that I can pay rent. Oh, I can get to a big enough audience size that I can sell ads and pay rent and also be able to afford food and that sort of- You can get a latte every day. I can get a latte every day and not worry about it. And so as a grew, sponsorship revenue grew. And so that was great. Sponsored deep dives, I had a couple of companies that were like, "I love the essays that you write about companies. Would you write one of those on our companies as like a sponsored thing?" And I was like, "I don't know, that seems weird. I think the audience probably is going to hate that, but I'll try it once." And so I did one and people were like, "Oh, that's actually really interesting." And so then I did it again and again and again.

And those, you'll always get somebody who reads the piece and is like, "Stopped reading at the beginning as soon as I saw that it was sponsored." And that's totally fine. The interesting thing is the feedback I get from other founders, and when founders tell me what their favorite piece was, a bunch of the time it's going to be one of those sponsored posts, because the founder has, one, wanted me to tell their story and trusted me with the company's story, two, paid money for it, and three, invested a lot of time into telling me what they're going for and giving me access to their financials and things that only their investors would see. Sometimes we are an investor in the company, and so we have this behind the scenes access. And I'm trying to figure out what is a thing that this company does that's unique or a way that they think about the world that's unique.

Or even just I've written about Ramp a few times and they structure their engineering team in such a way, and I think it's more complex than this now, but originally their fintech company that also wants to move really fast. And so they hire for engineers who like to move carefully and don't like anything to break and are a certain type of person who just wants everything to be perfect. And they put them on the core kind of payment, money movement, anything that touches money team.

And there's that side. And then they have a bunch of cracked engineers who have won international coding Olympiads. And they have multiple of these people, they've brought people in for other countries who are just competitive coders and move really, really fast and break things. And they give them a bunch of new features that if they break, really not the end of the world. And so they can move really, really fast and kind of maintain security and uptime, all the things that you need as someone who companies are relying on to move money.

And it's a little insight like that. This is an interesting way to manage an engineering team at a fast-growing company that needs to be stable. People cite that to me all the time as something that they thought was interesting in a piece that I wrote. And I don't think that's access that I get without doing those posts. So I really like them. I'm writing fewer of those, just because they're such a huge time investment. But the way that I be filtering those is, there's 20 companies that want me to write one of those for every one that I do. And so I'm not going to be in that piece being like, "Is this company good or is this company bad?" It's more the filtering happens in selecting the companies. And then from there it's trying to tell the story in a way that nobody's told it before. And so I'm happy with those.

And then the fund, I think is... Before I started doing this full time, if you told me, if you'd asked me what I wanted to do once I retire, it would be I want to write, I want to talk to smart people and I want to invest. And that would be my life. I view the fund as, one, I worked in startups for a while before this. I don't like the idea of sitting on the outside and writing about things without any skin in the game or without taking a stance and then putting my money where my mouth is on certain things. So that's a piece of it.

And then two, they just feed each other so unbelievably well. I think one of the underrated things about the combination of writing and investing, it's obvious why writing helps on the investing side, it's access. If founders read the newsletter, that's super helpful. They know how I think about the world. It helps there. I think on the other side, a fundraising process is essentially the founder distilling everything that they know and the thing that they're willing to bet their whole career on into a memo or a deck or a conversation with you and explain...

I talked to a mining company yesterday, I talked to an energy company yesterday, talked to a biotech company the day before. And these people are motivated and incentivized to get you to understand why they view the world the way that they view the world in a short a time is humanly possible, or send you the memo where it's like, "All right, a month and a half, I've taken everything that I know and try to condense it in this memo and here you go. Here's the result of that." And so it is all of these behind the scenes works of these really smart people that you don't get access to unless you're investing. And so I think that's been really, really cool and kind of an advantage in the way that I am able to gather information.

Yeah, that's a beautiful answer. And it got me thinking about how the best part of the internet and the worst part of the internet are so close together. The worst part of the internet is people with loud opinions talking about things where they have no expertise. And the best part of the internet is people with loud opinions talking about things where they have a bunch of expertise and they say, "You're wrong. I've thought about this bunch. I'm going to write something. I'm going to share something that's going to show you why you're wrong. I'm not going to do it in a way that's attacking you, but I'm really going to spell, 'Hey, this is how I think about it.' And I'm going to try to persuade you." And this to me is my mission with my career with this podcast, with Write of Passage, is there are so many people in the world who have this core idea, something that they've spent years thinking about. Sort of like we were saying with the

founder, this is the thing that they're willing to bet their life on. How can I help them to refine, to polish that idea, to get it out onto the internet and actually go share that? Because those pieces when I read them are so much fun. I remember many years ago I read this piece on the evolution of the craft beer industry. And when a piece is really well written and the ideas are very clearly explained, it actually doesn't matter that much what it is. People are like, "Oh, well I'm not sure I'm going to be interested in reading that. I'm not interested in that." It's like when something is really well written, you can read about anything. This is what's so much fun about having a writer that you like. You talk to people who like Bill Bryson, Bill Bryson wrote A Short History of Nearly Everything, 1927, The Body. It's like these topics are all over the place, but they like Bill Bryson, and he just explains something well, and you just come to trust that

the writer will make whatever it is that they're writing about a worthy experience for you. It almost kind of reframes who you're trying to reach with Write of Passage or with this podcast, and who you're trying to get to, right? If Write of Passage, you're trying to find people who want to write, it really is... I've been thinking a lot about this. I don't think I could get to this kind of audience size or whatever right now. The thing that I gravitate towards more and more is there is this 19-year-old genius who wrote this one thing on a poorly formatted blog somewhere, and what a goldmine that I was able to find this thing. How do you find all of those people who deeply, deeply, deeply understand their thing and get them to get it on paper? And they don't have to be good writers. Your job is to help them become a good writer. But how do you uncover those deep, crazy, deeply understood ideas? I think that this is the fundamental pivot

point that the pre-internet world has versus the post-internet world is you use the word find. How do you find these people? And that is the question that you have to ask before the internet exists. With the internet, the word is attract. And someone who I look at whose done an exceptional

job is Tyler Cowan. He has his Emergent Ventures program and he writes this idiosyncratic blog that it also isn't just about attracting people, the right people, but about repelling the wrong ones. And in the physical world, you're like, "Why would I want to repel people?" But in the digital world, once you start dealing with any sort of scale at all, actually repelling the wrong people becomes super important. So when it comes to a question like this, the way that I think about it is what do I write? What do I say? Who do I have on this show that's going to attract the kinds of people who have that core idea inside of them that they need to express, but then also repel people who aren't going to be serious? I don't want someone who's going to show up to Write of Passage and then is going to say, "Yeah, I'm just not here to write something superb." I'm like, "Okay, then get out. Just go somewhere else. I'm not interested in having you."

And how do I get those people, all those people together? And then what you end up having is you have people who go through a cohort, then they say, "Wow, I've never been a part of a community like this." But all that begins way upstream, not with applications and stuff like that, but with attracting and repelling people. Yeah. You can challenge the how do you get them to write something really excellent, and it's almost like how do you... Because I think ideas, people or ideas or whatever who get bigger, and I've seen this in my own, you get less weird or you get less spiky or I can speak to more people. It's like how do you find the spikiest idea and add variants into the universe of ideas that people actually get to see?

Because what you have is an audience and a way to get people to express something and all of that, and what they have is this crazy idea that would get no audience otherwise, but might make a lot of sense. So there definitely is the great writing piece, but I think there's also just the how do you attract these people who have ideas that will change the way that people think a little but? People who don't write, I think overestimate how important good writing is in the way that your fourth grade English teacher tried to get you to write like some poet or some novelist and like, "Well, I struggled in fourth grade, therefore I'm not a good writer." It actually comes down to a sense of conviction, unique life experiences, and then going through the work of synthesizing and clarifying that, because give you the editors. We've got a bunch of editors. I'll tell you exactly what to do. What I need you to bring is some life experience and some sense of

conviction. I can help you find that, and then I will just walk you down the path. And as long as you have enough fuel in the tank, we're going to get there. Now, can we do this 100 times? I don't know. Can we do one really good piece? Totally. Yeah. I was thinking this coming into this, I've listened to the podcast, obviously follow a lot of the people that you've interviewed and I'm like, "I'm actually, compared to these people, I'm just not that good a writer. I don't have a process."

You had Tiago on. He's thought about the whole thing around it so much, and I'm like, "I don't know. I try to find time between when my kid's diaper needs to be changed and when I have another call, and then I just write something. And I don't think very deeply about the sentence structure and all of that." But I don't think... In some cases it does. Some people are excellent writers and you read them for their wordsmanship and all of that, but I don't think it matters as much as people think. So maybe this is just a PSA that if I can write, you can write. Because I think it can be intimidating to hear writers talk and be like, "Wow, they put so much into this." And it's not that... It doesn't have to be that much. Yeah. Yeah. Remind me how you got to writing long

form pieces. I think was the fellowship that we did, was that, when you wrote Conjuring Scenius, was that the first long form piece or was that when you were like, "Nah, I don't process at all and I'm just going to..." Because we did that over three months. And then you went from that to writing one of those every week. And I'm like, "What?" Yeah, it was interesting. So I guess where this started was I was at my last company. We brought in an exec team who didn't words very much, and I thought that I was going to lose my mind, and just at the right time, I saw one of your tweets talking about Write of Passage, so I'm like, "I'm going to do Write of Passage, because I need to do something with my brain."

You know what you wrote? You said, "My goal is to get 20 newsletter subscribers." Yeah. I tweeted that I needed... And it wasn't even a goal, it was an assignment from you guys, like, you needed to get 20 people to sign up, and so I banged a little bit on the internet. The first essay that I wrote actually was just, I think you said find a writer that you... The assignment was like, find a writer that you like and talk about their writing. And I chose Ben Thompson. And out of however many people were in that class, in our first group meeting, you were like, "This essay was the best that I've..." Whatever nice thing you said about it. And I was like, "Oh, I might actually be able to write. This is great." And so I wrote a couple of smaller essays through that. Started the newsletter as the assignment, and so every week would send out links. And it was just a thing. I heard Byrne talk about this idea of not wanting

to forget things that you read, and I was like, "That's great. I want to just send a link email out with five links every week because I don't want to forget all of the things that I read." My grandmother had Alzheimer's, my biggest fear... I have a terrible memory. My biggest fear is just losing my memory at some point. And so how do I do a better job of capturing the things that I'm consuming? And I was doing, here's what a billboard would cost and here's what the subway ad costs, and trying to break it down. I should go reread that piece. But did a few smaller ones when an idea struck me like that. I wrote a piece on this idea of natively integrated companies, like these full stack companies that kind of do everything themselves.

That's been an idea I've been obsessed with for a while. So wrote that on the side. But the Scenius piece was, I think 11,000 words. Worked with Tom White as the editor. And I was so deep in my head

on that, and that was one where I really had paralysis around how much information, how many smart people had thought about how these random groups of people who were incredibly productive pop up over time. And there's always another book on the ancient Greeks or on the Scottish Enlightenment, or on any number of things that I could have read to make that piece better. And then I just dump a bunch of words into a doc and Tom would read versions of it. And it was the first time I'd worked with an editor and be like, "Whoa."

Everybody who worked with Tom in that fellowship said, "This guy is so good at editing." He was amazing. Every person. He made me not feel terrible about myself even while he was like, "I don't think you're saying what you want to say here." Or, "You completely lose me in this way." I was talking to an editor yesterday and he said, "Give me some feedback." And what I said to him is, the art of editing comes down to telling people what they need to do, but in a way that doesn't make them feel bad about themselves. And part of that comes from the way that you communicate what's going on. Another part with good editing is not just condemning what is there, but providing a solution for what could be better, and then building some sort of comprehensive framework synthesis where you can say, "Hey, you get three lines, three words each, one, two, three. These are the three things that you're doing in your piece. And if you stop doing those

things, your writing will get so much better." And when you get editing that accomplishes all of those things, it is a delight. And sometimes you get this holier than thou editor who's like, "What the heck is wrong with you?" It's like Cruella de Vil just stepping on you and you're just like, "Ugh." And that is a terrible feeling. Or even just the, "Unclear." Or, "This section is [inaudible 01:01:23]." Yeah. Little things where you're like, "Can you tell me why?" But can you just go rewrite the sentence for me? What do you mean when you say that? It's not even rewrite the sentence, it's just, give me some help. It just, get me started. Get me started with some momentum. Just don't tell me it's unclear. Just say, "It is unclear, and if you did this, I'd be way better off."

100%. Yeah. More specificity. You can just tell when Tom's editing you, he cares and really wants to make it good, and it's his mission to make it good with you. I don't know what that flipped in me, but then you're right after that, I started writing 5,000, 10,000 word essays every week instead of in three months. I think there is something freeing about knowing that it's not the piece that I'm working on and it's just like, all right, I'm doing this every week, and so I'm going to just put as much information in this as I need to. It's not going to be perfect.

I struggle with this one a little bit. Or sometimes I'm like, "Should I just go schedule at this point and just write when I think that I have something interesting to say and really craft it?" I have no idea how I would be at that. Or if the body of work that builds on each other and feeds off each other is an interesting thing. Or if I have it in me to write the one piece that breaks the internet every once in a while. It might be worth experimenting with at some point just to see, but I haven't been able to make the leap into doing that.

When you wrote The Great Online Game, did you expect that to break the internet?

No. That one is like I wrote it, and this is when I didn't do this all the time, I had a draft on Saturday that I thought was not that good. And so I threw it out Sunday morning and I just wrote that piece in a day really fresh from my idea to publishing, which even now is rare that I'll have the idea write in a day. I was like, "That's a cool... It's interesting, but a throw away kind of piece that I don't think it's going to be anything special." And then it kind of took off.

It more than kind of took off. I feel like it was the talk of the town for a week. It was the talk of the town. And it's still the piece that people cite the most. And I think the thing that it did, and I don't know how to do this, and I'm sure that they're really great writers and cultural commentators who have developed the skill of doing this, but I think the thing that it did was was me putting into words the thing that I had noticed that didn't have a name that everybody else was like, "Oh, yeah, I also noticed this thing." And there's a little bit in that of there's noticing the thing... And people also just being told how to do something. It's the fact that The Great Online Game had a thing that you can go do and you can go play and like, "Oh, there might be this amazing opportunity on the other side."

If I'd known so many people were going to read it and refer to it, I actually probably might not have written it the same way, because I'd maybe be embarrassed to say, "This is how you should be on the internet." Because everybody can do their own thing on the internet, but it was really just like, not a lot of time, noticing a thing that like, "Wow, this is actually a really serious place now where it feels like you're just typing things, and then look what's happened here." I can't believe I've been sitting in my in-laws basement and I get to talk to all these people that I've always wanted to talk to and get to reach however many people were reading Not Boring at the time. It was less than 50,000 people reading Not Boring at that time. And so I just thought it was this magical thing, and then I think it was just the right balance of other people had noticed it and felt it a little bit, or some people wanted

something similar to happen to themselves. And so it just kind of captured all of that. I think you're speaking to something deeply paradoxical about writing is that when you try to write for the stadium, you don't hit the stadium. And when you try to write for the individual, you're so much more likely to hit the stadium. No matter how often I say that, I still try to write for the dang stadium. And then I'll write, I do a journal thing with a friend every day, and I find that so much of my best writing just comes in what I journal to him. And there's one person who reads it. And I think that to go back to one of the challenges of writing on the internet trying to reach an audience is you lose that letter to a friend feeling that there's an intimacy about that. Why don't you publish those?

These really, really, this has nothing to do with writing. It's so close to me that maybe I'll do it later in life when I'm in my 80s or something, but I really work hard on them and I write one every day. They're like 200, 250 words, takes about an hour and a half, and it's on the post side of my Bible study. And it's like, what did the Bible reveal that I need to know and who I need to be and what I need to do? And it's

the thought of publishing those is terrifying. Yeah. A separate question for you, because I've been curious about this. Are you familiar with Jesse Michels, American Alchemy? Yeah. Or American Alchemist. He, at one point on, I think he was on the Theory of Everything, the Theories of Everything podcast, and said something about the Bibles as almost these codes that were made to... Or the Gospels as these codes that were made to survive over to be Lindy, to be transmitted, to reveal more and more of themselves over time as people understood more and more about them. It's not a way that I thought about the Jesus parables or the way that he taught or spoke or anything ever before. And I hadn't given it a ton of thought since, but I think it's interesting, the New Testament's 2,000 years old.

Do you think we've lost... Do you think there will ever be looking back from 100,000 years, a text like that again? Or because we're not spoken word anymore, because the internet moves so quickly, because there's so many people producing content is impossible to get that spot ever? Yeah. Well, I think that there's two very different answers to that question, and it depends on what you believe about who Jesus was. And I think that there's no way to actually know. No matter what, there's a leap of faith. So I'm going to put both of these two ideas out there. And I think that there's very, very respectable arguments for both of them.

So the first I'll give the you're not a believer answer. I think that yes, it is possible. It takes somebody who, a person who has a real art and a knack for writing things that are worth memorizing, and they're probably going to be a poet who's just incredibly wise, and that would be their goal. How do you write things that people can remember over time? Then the religious answer of a Christian would say, well, Jesus was the son of God. And the reason that it is so profound is of course it is, God things and Jesus was fully man and fully God. And then even the other letters, the Holy Spirit was working through the hand of Paul and John and different writers in the New Testament, but this is actually a God thing, so it's really up to God and not up to man. So those are two very different answers.

Yeah, that one's hard to argue with. The non-believer one I think is so interesting, because I think one of the other things about it was... And it's impossible to read the Bible this way after having gone to Catholic school. It just seems so bland and old and boring and whatever, but it was so novel and so controversial, the things that Jesus is teaching and the idea that you should love people and the idea that people are worshiping somebody who was killed on a cross in the way that the slaves are, the Tom Holland argument about Jesus. It's almost impossible to create, maybe not, but to create something, to create a set of ideas that novel at this point, just because there's so many ideas. Any combination and permutation of things either has been tried or somebody will try and will tweet. I think that's another challenge to doing it. Even this wise, incredible poet, he is going to have a really hard

time shocking the world enough to stick. Yeah, I think that this is one of those arguments that I refuse to accept. And I actually don't know if I refuse to accept it because I'm right or because to accept this means to resign to this sort of end of history argument. But I think that people say a lot when they're talking about something like technological stagnation or why there's no new Shakespeare or something like that. They're like, no, all the ideas are out there and stuff. But I've just noticed, at least in my own life, oh my goodness, I'll discover something and then there's more there and there's more there. I just have a deep conviction that it's there. And I actually might be wrong, but I think that if I think that, then, oh, no [inaudible 01:11:08] new.

I'm on your team on this, right? I am certainly not a believer that we've... The whole point of Not Boring is that we have not [inaudible 01:11:17] that things compound on each other and all of these new things are possible. And so there's like there's plenty left to discover and there's so much left to explore, and we're on this little rock in this impossibly big universe. And so all of that I agree with. I think I'm probably also being short-sighted on the other side of this argument where it's just like there is this weird set of conditions where, to your point, there was oral history, things weren't allowed to be said, whereas now it's not that all the ideas are taken, it's just as soon as there's an interesting thing to say, a thousand... I'd run this exercise, I tweeted about this the other day, where I'll think of something and I'll be like, "Oh, that's a clever phrase." And then I'll search it and thousands of people have said

that thing before. And so there's a little bit of that. I think I'm probably being short-sighted on... We'll put neural links in it. There'll be the first great neural link communicator who's able to speak directly into people's brains, or there will be some other opportunity for that. Right. Yeah. I'm always amazed by two things, and they're directly intention with each other. The first is exactly what you're saying. Oh, everything, I mean, I've heard this, I've heard that, I've heard this, I've heard that. And at this point, I've just read millions and millions and millions of words. I've read so much that it's like a lot of things I just can tell are just regurgitated. It's like, okay, I know exactly where you got that from. You got that from this book, this chapter, and there's sort of an eye rolling that comes from it. But then, man, I'll find one tweet a week and someone will say something, and it's as if they've unlocked a new

feeling or a new way of describing something. Something happened yesterday. I was reading a essay from Amor Towles about the painting, Nighthawks, reading the piece. And he says, "What's interesting about this piece is that the predominant feeling is one of melancholy but..." Melancholy implies a sense of somber sadness. But he goes, "But given the context of the city of Manhattan, the melancholy here is actually happy." So he says, "Melancholy, but not in a sad way." And then he sort of starts going through it. And I'm like, oh my goodness, I never imagined that melancholy could actually imply a sense of happiness. But the way he said it was like five words, and he gave me, he gifted me this new emotion that I didn't know existed. It's like seeing a new color. And I'm like, "What?" And I think that the possibility for that is nearly infinite. That's amazing. And I kind of know what you're talking about, the sense of melancholy within New York City. Yeah. That's brilliant.

Yeah. Well, he's brilliant. He's brilliant. Where do you turn to for inspiration? Where do you find to be the most fruitful place to be looking that fuels your writing process?

My favorite thing to do every once in a while, particularly if I'm feeling stale, is to tweet and ask people for their favorite essays that are more than a couple of years old. And I have one time where I got a really great list that I'll keep going back to and back to. And they could be short little essays, they could be long in-depth pieces, but just rapid fire reading five or 10 great essays and different ways that people write about things. That just refreshes me. I'm like, "Oh, cool. That's how you write." So that's from the writing side of things.

And what is that? Is that with the quality of writing? Is it with the ideas? What's going on there? It's with the quality of writing. It depends on the piece. Some are just magically written. Some take an idea that I'd never thought of before, and just go deep on that idea and then talk about the world in a different way. What's one of those essays? I love the essay Becoming a Magician by Autotranslucence. Great piece. I love that piece.

Yeah, it's almost like ethereal, but you also really kind of feel it and you're like, "Oh, I know exactly what you're talking about where these people who are just so unbelievably good at a certain thing." You're like, there's just those little ideas. But there's a line in that piece that I think hits it. And I think that that's so much of what I'm going for with how I write is, how do we find these magicians? And the way that she defines a magician is somebody who's different than you, not in quantity, but in kind. So somebody where if you walked along that path, the path that you think that they're on and you walked a trillion miles, you would never get to where they are because there's something that they know that they're doing that you fundamentally cannot comprehend. And your attraction to them is the puzzle to try to figure out, what is it that they're doing? Yes. That one I try to read every time. It's

a list of, I don't know, it must be over 100 essays, but that is one that every time I go back. And why do you think it resonates with you so much? I can't even describe it. It's just that feeling, and maybe it's the great unlinked thing where it's finding something that I'd maybe thought before but didn't put into words. And I think that just captures that feeling for me so well that I go back and just try to get that feeling from the piece more than any particular sentence. The way that I think about consuming information is if I'm specifically researching a piece, I'm just looking for as much information and facts and whatever as I possibly can. If I'm generally reading, I have a terrible memory. I don't have the Ben Thompson, or Byrne Hobart, or Mark Andreessen, the three of their brains work like this, and I'm not inside their brain, but it seems like it from the outside, where you just have a framework

for things like a really strong base such that every new thing that you see and more capacity burn [inaudible 01:17:12] didn't have a good memory. I don't know if I believe that or not. And this framework where anytime you read something new, you're like, "Oh, that hangs right there on the frame, and that hangs right there and that hangs..." And mine is just like, it just jumbles. And I was upset about it, not upset, upset is way too strong a word, but try to do space repetition or try to remember things. And I was like, "You know what? I could do that and bang my head against the wall, and it's just not going to actually really get me anywhere. Or I can just try to put as much interesting stuff in my brain as humanly possible and hope that it bangs into each other and creates some weird idea that just pops out at a random time." And so I've almost given up on trying to memorize. And I would love to be able to do it,

and I think it's a waste of time for me personally to really try to memorize things. And so now I just try to have well-written things or interesting things or novel and weird things that can pop in and bounce around in my brain and hopefully turn into something interesting. Do you read a lot of books? I read a lot of books. Yeah. Fiction, non-fiction, sci-fi I was doing for a little while, a little bit less of now. But love just to, I think for what I'm writing about and what I do, I think there's something interesting about seeing 1,000 year from now ideas or 100 year from now ideas and inhabiting that world. I think most sci-di is actually pretty horribly written. And you read the prose and you're like, "Oh, this is not that good." But there is something about inhabiting a world that just assumes that all of the things that seem almost impossible right now just happened. And then coming back

to the present and then seeing just the ideas that are a year or two away and being like, "Oh, obviously something like that is going to happen. Is this the one? Or does the business model make sense right now? Or the cost of inputs, do they make sense for this to be a margin positive business?" But it's not like, "Oh, that's stupid or crazy." It's like, "Oh yeah, I recognize this idea from the future that this person is trying to build now." And so that's pretty cool.

As you look at your writing, what is the biggest thing that irks you about it? This is something maybe that more irks me about myself. I wish that I had just a little bit more technical depth on things or a little bit better of an understanding of exactly the next level down of how something works. And I think I have an okay level for at least tracking what's important about something and then being able to explain it back. And I think that's one of the things that I do well. But then there's, if you scratch three levels deeper, you've lost me. And just actually, I'd love to be able to have that gear. One of the things that I've really noticed in our time together today is how well you have surrendered and aligned yourself to, this is who Packy is, and I'm going to be that person. There have been multiple moments in this conversation where you've said, "I'm this person, so that's what I'm going to do. I'm not going to

fight it. I'm not going to fight it. I'm not going to go try to memorize. I'm an optimist. I'm going to lean into that because that's how it is. And someone might critique that, hey, my piece about some company is going to be optimistic." You just did it there. And I think that, look, this is probably a prerequisite for writing a piece every week, and I think that this is one of the fundamental arguments that I make for writing, that writing helps you learn about yourself. Why? Because you can lie to yourself for piece one, you can lie to yourself for piece two and piece three, but you can't lie to yourself for piece 200. By piece 200, writing about things that you don't want to be writing about sucks so much, sucks so much that you're just going to have to surrender and say, "This is who I actually am, because otherwise I'm not going to be able to write piece number 205." Yeah, I've never thought about it that way,

but not that you said it, it sounds so obvious. I've become a lot more at peace and just knowledgeable about, I guess, who I am through writing. In the beginning, I remember thinking, "Look, if I try to write very academic or sophisticated style, I'm just going to get really tired. I write too much. I cannot actually physically do this every... Pretending to be someone I'm not in these pieces is actually just going to be physically impossible. I won't be able to write every week if I do that." But you're right. Every little while there's something else that I uncover about myself that I just don't try to fight. And that's probably not great for audience eyes or great for a bunch of these things where it's like, oh, this week I'm interested in this wild biotech company, and the next week I'm talking about space. It's exactly what they tell you not to do audience building wise, but it's like I just get

so... If I'm going to put the effort into write this much every week, I want to find the thing that I'm the most fascinated by. I mean, it's the only choice. Yeah. I mean, you sort of said, "If I'm going to do it, then I want to write the thing I'm most fascinated by." Writing the kind of piece that you write every week is hard enough, the least you can do, and I think the only way you can do it is you have to be on fire for that idea. And here's the thing, you and I, I think our curiosities function in similar ways where sometimes we're like, "Why am I interested in that?" But you're just on fire for that idea, and your brain isn't in charge. There's something else that's like, you are the dog and there is something else that is the leash that you're just like... And you're yanking your brain to go follow that thing. Totally.

Is there anything else for us to talk about? I think, I mean, this was a little bit of therapy, a little bit of reunion. This was great. Yeah, no, it was a good time. Thanks for coming on, man. Thanks for having me.