Packy McCormick: How To Publish Your Best Ideas Online

What Makes For A Good Title Thumbnail For Sentence? Born to Tell Dad Joves. I like a good pun. The goal is like, 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,

can 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 humors, 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? Packies 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, way back to the days when you literally hadn't written anything and I was teaching read a 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 like literally last minute before I hit publish, be like, well, every every time I start writing a piece, I have a title up top. And sometimes it stays because like sometimes a title is almost like why I want to read the piece. I'm like, oh, that's a really interesting like idea

in 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 read the piece. So we can go into the process and it's gotten like 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 Dolly? Do I need to do something? Hopefully I've like drawn something that that works as a title image. And then we'll throw that in as like the last

thing once I finally written the piece. But that's, yeah, it's a messy, messy process. What makes for a good title thumbnail for sentence? I think what makes for a good title is, I mean, I'm like, I was born to be a dad. I'm like born to tell dad jokes. I like a good pun. I think if it's like if it can convey the idea, but be kind of fun and catch somebody's attention, like that's a good title. The good thumbnail image, I think for 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 like a really good bar chart or like a really good chart of some sort or a really good number. It 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 like 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. I actually 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. The first few paragraphs, the way that I think about and describe it is like if you're skiing a fresh run like figuring out

your line ahead of time is like really important. Once you figure out your line and you just kind of go and you're like going through the piece. If I can figure out how to frame the thing, all the other sections kind of fall into place from like, oh, I'll need to describe this if I'm

talking about this. And like here's a definition of the 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 understand, 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 be in to see where they're going? Totally. And I think I

can actually do a better job at both hooks and letting readers see where they're going. I think like, you know, there's a lot of things that we talked about in right of passage or that people talk about generally like right short pieces. Like people know exactly what's going on a friend. And I could probably get a lot better at that. I think it's more like, I want to figure out like the right interesting path through this piece. And like, I hope I have people up front with that.

But I like really try not to be hyperbolic. And I like, there's maybe like some sort of embarrassment if I'm like trying to get too oaky in the beginning. And so I really just wanted to be like, what's the most interesting way to tell this particular story that nobody's told it before? Like, I think that there is a lot of sort of thing about it is like beta content and then like alpha content. And there's like a lot of beta and just like, oh, we're, you know, like AI is going to

change the world. Like who cares? You know, like everybody's writing that thing. If you read another piece on that, you're not going to get any smarter on it. But like maybe in 10,000 words and hopefully in the introduction, I can like, change the way that you think about an idea just enough that like, you're not going to remember exactly what I wrote in the piece. But like, maybe it'll just like shake something loose in your brain. So that you think about the world in like a little bit of a

different way or you're like, maybe a little bit more optimistic about something. You think it's a little bit more likely that like a thing like this might happen. And so I'm more going for that than like, oh man, like that this is the hook that somebody's going to keep reading for. Yeah, I got this from Sam par when he came on the show. He said that what works really well in the internet is like these barbell pieces. So there's some short pieces that say a few hundred

words. And I think of those as something that would be like a screenshot essay or like 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 like producing these short little bits, almost like a comedian, you know, it's sort of would be like 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 like 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 Gabrielle does a really good job of this. These long form pieces where you basically throw 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 think that's, I mean, every time I read 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 analyst to spend all their time thinking about it. 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 I was like, everybody's talking about Stripe. Like, what is the thing that I can write about Stripe to make this the best piece that has been written on Stripe today? I think Mario has since written a great one and and Bern 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 like, that is the goal whenever I write about a company still, whenever I write about a company, the goal is like, 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, you know, they didn't before the comment that I get from people after I write a deep dive in a company most often is like, I'll get employees with the company emailing me or the founder even say, like, finally, my mom understands what I do, which is cool because I think it says a few different things. Like, one, I'm writing about the types of companies that like actually aren't that easy for them.

The mom to understand what these people do and those just are, you know, they've attracted me even more and more over time. But then to like, my job, I think, is to be like, the kind of dumb guy. And like, you know, they don't mean this to be like self-fitting. But like, the person who like really needs to like actually figure this out, belongs to the audience or like just before the audience did and explain it in a way that like a regular person can. I think if you're like too smart or

too deep in an industry, it's like hard to do that. But I'm like, just dumb enough that I can go into a new topic, a new company, a new space and like really just try to do all the research and work. And then like, put as much of the like, here's what I'm learning as I learn it. And like, let me try to describe it in a way that like helped it click for me. Then I possibly can. So that's a little bit of a goal with this. 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's, that's 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 Gabrielle 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, story about power and ambition and boldness. And you see that, okay, there should be a human component in this piece. Just one sentence and you've set up that whole scene. He's the master. At that, I mean, I think talk about it, you know, I start out every one of many of his letters with welcome to the X number of new smart curious people. And I think that I'm a smart curious

audience of people, but talk about respecting your audience in the way that Mario does. He's like, oh yeah, people are going to understand exactly what I mean when I say imaginative, 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 underlying. And we can say

Romulus and Remus, okay, go read that on your own. Yeah. 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 got along and you don't take the time to explain it, you just say you're going to know what this is like bird hobart does

a great job of this. Yes. You're like, I feel smarter when I read bird hobart. It's like, I've been invited into the esteemed leisure of bird 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, you know, 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 they're like, that was a good piece. If there are 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? Like 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, you know, we'll do the right 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 like finding the intersection of a few different things you care about. And so I was like, incredibly on the news 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 said this before, but remember this thing 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 counterposition against him? Like he's never going to be as silly as I am in the news letters. 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 like, what if I do that and just like really lean in hard to that? And so the first 10, like kind of full essays that I wrote enough worrying were here's a pop culture thing. And here's how it's like a thing that's

happening in business or technology. Over time, like 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 real 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, like maybe my voice has gotten, you know, a little more consistent just obviously from writing hundreds and hundreds I've pervidden over it, publish over a million words pretty easily at this point. And so it's probably developed just based on repetition. But I do also kind of think that I need to start reading some more of my old stuff and like get a little bit of that freshness and a reference back. There's something weird that happens

where in the beginning, I was writing as a total outsider. So I mean, 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, maybe have invested in, certainly know the founders of don't want to say anything mean about. And so like I think maybe it just like, and certainly there's also probably a, you know, like I know that when I've said something

like this before, I've gotten dunked on for it. And so like there's definitely a little bit of the like defensiveness in there, a caution that I like need to figure out how to remove. Oh, I feel you, man. I mean, the way the, the, the way that I was thinking about what you just said is that when you first start, there's you. And like it's timid you, it scared you. It's, I've never done this before you. And over time, what's nice is that the you becomes a little bit

more confident. You're now like, ah, you know, 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 Paki on the internet and who is Paki in real life. And so now that 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 Dave 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 like tug of war that emerges over. Yeah. No, I've been, I've been really proud about being very willing to like shift topics or, you know, like, write about completely different things

from week to week and like try not to become like too much of a thing. I think there is a threat of optimism. But that is like very much who I am and like how I see the world. So that doesn't feel like faking anything. But then they're, they're just is like, so I wrote a piece this week. And I used a phrase that I'd heard from a founder that we spoke and do that I really like

called cost physics. And I use the word in the piece or use the phrase in the piece. And then I was actually going to write a whole other piece and might still do this, but write a whole other 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 like did all these different searches, finalated Twitter. And the first thing that comes up

was like essentially like some non-account being like cost physics. Like what the fuck is this? Like, you know, and like making fun of this thing and like saw this thread kind of they're like, you know, making fun of this idea of like, oh look at BC's rediscovering like manufacture. You know, like the whole thing. Now I'm like, do I write about cost physics or is it like dumb? And I think it's a cool like 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 asses 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 to go for more and more is like, first of all, I need to figure out the truth for myself. I think

it's Robert Triver. She has his paper from like the 1970s. We 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 like, 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, that was the easiest thing ever. All I need to do is just talk about what happened, you know, totally. Yeah, I see that all the time when I try to overthink something or like over intellectualize it or sound smarter than I am. It just like, it comes across

as flat if I'm like, I'm excited about this thing. Like, how do I get this excitement on the page without actually like being so excited that people are just like, ah, like that is just being excited about something again. But like, yeah, how do you get the genuine feeling that you have and the genuine way that you think about something? Like, 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. And it's like, how do I get the fact that I think this is fascinating enough to write about not perfect, not like going to change the world inevitably. But like, one of the most interesting things that I can be writing about right now, how do I get that excitement? Like, what got me interested in the thing in the first place down under the page? And talk to you 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 like get an idea. The first draft is never going to be good, but I just try to like write a version of that draft while I'm still excited. I remember from right of passage, they're like, you know, just write as much as you can. Don't do any research. Don't edit yourself. Don't. And I don't do that. Like, I come to a new idea as I like, I'm trying to do that. I start doing that. I start writing. I have like the excitement.

And I'm like, I don't understand that. So like, let me go and research that thing. So I understand it. Oh, this is actually like the ties to this all like download a book on the Kindle and like reread it.

And so every essay is like 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. Like, what if I got myself into then get excited again, then write and then like kind of 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, I open up a Google Doc, do the, you know, 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 like, use that as the doc where I dump all of the bad, like the stuff that I cut from the other versions. I've been going through like six versions. We're all right. It. I'll find a good

section or like, you know, keep the introduction. Find another good section. But like completely start fresh and start fresh and new doc like not try to add to myself at all. And like, all right, I'm just going to try to capture that excitement and just like start typing again. And that won't be it. And so like, I get to, it's almost like if I find the skier on like, I get to a spot where I just like hit a wall and I'm like, oh, this is like actually not the right path. And so I need to go

back to the top and like, 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. And really, 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 like this path might be the right one. There's definitely, and like,

this is not an uncommon thing. Like, there's nothing special about me here. But like, some sort of deadline really, really helps. And like, I just kind of all comes together. I can say it better when I had 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, four, 30 the morning that I'm going to send. I wake up tilling maybe edit, maybe rewrite,

rewrite the whole thing from 430 to 855 AM. And like, there will be it's not just like completely fresh. And this is not for if I'm writing a deep dive on a company where I've like spoken to the company a bunch. I've like, done a lot of research. I know the angle like, those are going to be set in place a couple of days before. And that'll be editing at the end for the other pieces. I think at the last like 10 essays that I've written, I've rewritten at 430 in the morning,

under the gun, texting my brother. We've sponsors in the newsletter. So like, texting Dan, who's been running AdSales, but is now focusing full full time on his business. But texting him being like, do you think like sponsor X would mind if we sent tomorrow and like racing and then texting him at 830 mean that I actually think we have something like I'll send it. We'll throw the copy in there. But that's 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 like for whatever reason, I need like that amount of time pressure to get a done race. And wow, that sounds like my heart is so fast right now. I don't even know what to say. Like that sounds that sounds so intense and struck with panic. Does 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 one year old. Before the kids, I was just like,

you know, morning to night, all weekend, whatever I needed to do to raid the peace. And now I've tried to and then I actually took that into having the kids like my wife, Pooja, it is the best would be like, all right, cool. I'll take them, you know, like I was like pretend like I don't golf. Pretend that like my golf is right. Pretend that I'm golfing right now. For six, I need six hours. I'm not going to be drinking beers with the boys. I'm just like,

I'm sitting there right here. I need six hours. But it would just bring like this stress into the weekend where I'd like be with my family and then it'd be like kind of on edge and like everybody could I mean, the kids could input Pooja could certainly tell like, you'd rather be riding right now than like sitting here because like you had an idea. And so I've really tried to remove the stress from the weekends and like just batch. I started starting sending on Tuesday instead of Monday. So I

at least have that day to like run through some more drafts. But I've really like kind of pushed all that stress into the last, you know, four and a half hours from port. They're didn't mind. Yeah, it's funny that you say that because I felt the same thing like 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 I would just read and read and read and read and then I'd have like double riding times like double jeopardy but for riding, you know. Yeah. And I would just do it all day and I wouldn't have plans and stuff. And then now it's kind of the point where I do not work on Sundays. Like I just will not work on Sundays. Sundays are totally different. But every week, I'm like, you know what? This week I might 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 it's really interesting. So you've had, and you've had Bernani. 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 like the ability to hang new information into things as it comes up. In a way that it doesn't sound like, you know, his process is easy. He's also waking up at 5 a.m. to write and does it every day which I don't understand. But like his value add is that his horsepower and like the way that he thinks about the world is just like 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 like be the guy who's like more obsessed

with figuring out more about this topic than anybody else. And so that time crunch like makes me feel like I lose a little bit of that super power right? You know, you know, this is my this is my packy riff on who you are. So like it's like a bunch of friends, you know, sitting around the table, you're laughing, maybe you have two beers, okay, for the sake of the story, two beers. You know that moment where like 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 like 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 like 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 of it that way, but I really like that. That's what I wanted to feel like. Like 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. Like there is sci-fi happening. There's like this drama happening. But like there's these kids and like just geniuses who are building these things for people. And the way that it gets written about is so dry. Like I think business strategy is so interesting. And I like, you know, Richard Rommel's good strategy, bad strategy. I think it's like a little bit better written. Obviously

Ben Hopson stuff is like he's really, really good. But most of the time people read about business. So like, oh, you're talking about business. Like please don't talk about business here. Like 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 like try to convey like why I think it's so fun and interesting to people.

And a way that they're like, oh, actually, like 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 great a entrepreneur, say engineer. And then also he's a meamer. And he's funny. And because you get the laughs, then when he talks about, hey, you're saying you need to think about strategy and a production line. I'm like, well, I like this guy because he's he's he's he's waking me laugh all the time. And you know,

and then he has a meme that just how it's just like a manual Kant gangus cod. Yeah. That was that was very good. It's so it. I'm sure you'll probably interview Walter Isaacson at some point. Yeah. And so apologies in advance. I'm sure you won't listen to my episode. I really liked the Elon book. I thought the central like question of the book, which is essentially like, would Elon be able to do all of this if he weren't this like kind of crazy person.

It was just like such a nonsense question because the answer is like so clearly no. Like those two things go together so tightly. And that's awesome. Like we are so lucky to have people in the world who you know, like my lucky canceled here. Like I think the Clinton's that a great marriage. Like I think if you if you are two people of eight billion who want to get together because you want to achieve these like outlandish things that nobody achieves. And like

you don't have the most loving relationship and like somebody. Okay. Like what a great partnership you're able to find where one of you was president and the other of you almost became president. Like that is a success in what they were going for in that marriage. And so like the fact that there are some people who live unconventionally and are willing to like do this crazy stuff to try to do

these big things. I think it's wonderful. And I think that's like such a silly question because like no, you're like you need that Elon crazy and like net net what a positive thing for the world that that that exists. You're talking about flow. What is that practically look like for you? Flow is like getting five pages into an essay and be like, whoa, I wrote five pages and then go back and kind of reading it and be like, well, that was actually like pretty good. And that's like kind of

what I wanted to say. And then basically obvious example is like the the welfare all debates in in all school where he just like black sound came to and like it's that something really good. But it's like, well, I actually like I didn't think that I was going to write exactly this when I started writing this thing. And now that I look back, like that was better than I, you know, had I over intellectualized it and like thought about the words too much like something that I wouldn't

ever written. And so flow is like almost a thing that I realized happened after the fact if I've ever written something good that I like hadn't gone into that writing intending to 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 like 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's just like my fingers feel I can hear them crackling a little. I like what's going on right? I can crack my fingers easily. I'm like, what's going on with my fingers? You know, 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, voice translation and voice transcription. So super whisper has helped me where what I do is I just pace around the room where 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 like take your chunks of ideas and write them in words that there is no doubt that I have to edit more. There's 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? Yes. Yes. Do you have like 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 Mike Moboson and he likes to quote this paper from 1980 called It's a mouthful on the impossibility of

informationally efficient markets. Okay. We're basically says the whole one is you can't have efficient markets for information. You actually just because there's a cost of collecting data. But 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. Yeah. So I have that idea. I have the structure in my head. I have the first part. I have the second part. 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 I'll 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 air drop on the computer, type it up and the piece will be done. And do you feel like a crazy person walking around like? Yes. Yes. What goes on your head? Do you think like, 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 because I've had exactly this. I'm like, oh, you know, if I'm 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 memory or something. So it only makes me mildly crazy. Perfect. That's great. What's at time where you

feel like you were really in a flow? So maybe not even as much on the writing side. Like the times that I'm thinking about like I wrote this piece on 10 cent and I ended up turning into two-part piece. This was like fairly early on when I had nothing but time. This was like early COVID. I was at my parents house like nothing to do. Like my mom would cook meals. So like absolutely nothing to do. And I was like, you know what? I think they're the portfolio of investments they've

made is super interesting. It doesn't exist anywhere. And so I'm just going to like get into the internet and like go to Chinese language sites and like find all the like cross-references with each other and like find as much of 10 cents investment portfolio as I possibly can and put it into a spreadsheet. And that was like two days worth of just like digging and finding something

that's really contradicted and like then having to find a third source. But it just felt like by the end of it I was like, oh no, no, no, I know we're all the different things are hidden here. And like I'm not going to fall for that, you know, bad data source again because I saw that over here. And it was just like a couple of days of like by the end of my cup 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, like 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, technology.com, technovelgy.com where this guy just takes all the sci-fi and like lists out line by line, you know, this book in this year said this idea or you know, had this idea for this technology. And then he'll like go back and link new news sources like to when that thing

actually came true. And so I did a project where I took as many of those like I like copied and paced, paced it from the web page into an excel sheet. I used chat GPT to format the spreadsheet like get it into like a place that was consumable. And then I used two different and thropping accounts because I would rate limit the end thropping accounts back and forth trying to like have them explain whether that idea had come true or not on this like 3000 entry list. And it was the

same kind of thing where like it was two days. And like finally when I cracked this like, oh wow, like this thing is like actually starting to work and like everything that it's saying makes sense. I remember just sitting in the room. There's actually the staff my parents house also, uh, with the kids where they were watching the mountains great. Just like flowing back and forth between and thropping and then taking the sheets out and putting it in the spreadsheet. And by the end,

I was like, oh my god, like this is a really cool resource. And people I think say I still see people kind of sharing the sci-fi idea bank. But it was just like a couple of days of like I'm gonna flow on this research as much as I can. You know, so this is a inside joke that we have at writer passage me and my ops guy. He looks at the website analytics and the most repeatedly red 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 like crazy thing to download it at the time. It was like, you know, it was like 50 50. Am I going to have all my money stolen from me or am I going to get this memo? Yeah. You know, 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, that's right. You know, yes. And people love when you've like uncovered a gem. Yes. For sure. So there's like the two

different things. There's, can I give people this source in my writing and like, 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 like, you know, you're reading something or listening to something and you get a quote and you're just like, that's that's exactly my, thank you. Like that

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 of very successful founders before they were very successful. Yeah. 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. Like 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. And, but it was one of those things where media trains, Zach would never say that. And that genre, those early interviews are really good. I mean, Zach had another one was the carousel swisher interview, where he was in the red chair and just sweating profusely. Yeah, it takes off the jacket of the sweater. And then it's like some symbol in this sweater. Yeah, I feel like after that is what he got media trained.

Yeah. Because he got ripped apart for that. So badly, he's a public company CEO. The other amazing video from that genre is the Jeff Bezos one of that's been sharing a million dives that Jeff Bezos is talking about Amazon. Great, 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. Like so I'll say like here's a phrase, explain this and then I can ask

a bunch of questions about it. I'll like 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 it 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 GPT and anthropic and Claude are both pretty bad editors in different ways.

And so some of it is just like making like sanity checking the democracy and having the AI dummy nice things about the piece that I'm writing because like it has so complimentary. It's like, wow, this is a very thoughtful reflection on something. I'm like, thank you. Claude in particular. Cheggy PT is like a little, it can be like a little little little more cross-ity. But Claude in particular is like, this is I mean like what a contribution to the field and like,

full of the law. It's an A. And with this one tweak, it's like definitely an A plus among the best things ever written and like perfect. Like there's exactly what I'm going for. And so there is a little bit of like as I'm going through these drafts and like I'm halfway through the piece and like, man, I'm stuck here. Like I'm just going to, it's like almost how I take a break from the

pieces. Like, let me just dump it in here and have it tell me nice things. And like maybe it'll say like, you know, this thing is confusing or I'll also ask it to tell me and Cheggy PT is actually better. This one is what I'm saying here right or like how like where would you like your job is to like cynically attack this like where did I get this wrong? Yes. Unthings and I'm like trying to explain and it's actually pretty good at that. I think the danger there is to like then not add

like a bunch of qualifiers afterwards like, oh, you know, like I'm saying this. But like also I understand that like X, Y and Z like there is a balance between being being balanced and like, you know, having writing that moves and like has a point of view and all of that. But it is nice to know like if there are any bodies hidden 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 the source. A bomb the source. So what I do is I'll take a sentence, copy and paste the sentence and 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 what I'm trying to like the emotional tenor of what I'm trying to convey is this. So good. Yep. I will do that with the blank. And so like if I'm like, I don't know the right

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

That is I think what really hard on it in the beginning. And I think like, you know, that there are some there are some people who have their own distinct style. There's someone Meg's on Twitter who has like this beautiful. I think she calls it like techno-alisian. It's like robots and flying robes and like has like really honed the style. There's some people who have like their very own like style where they run the same prompts and like ask for different things. But

have the same like 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 like kind of generic and mid-Journey or Torr Dali. And so in the beginning, I was like, this is awesome. Like I will never have to like draw something ever again. I'm just going to ask for the perfect image. And sometimes the image is a perfect and sometimes they're not. But they all end up looking a little bit alike. And you could

tell them they're they're I generated. And so now I use them a little more blood-wrestlingly. I use one because I just like had no dime the other day. I want to write my piece to make the title image. And so I'll do that if I like if I'm totally out of time again. Trust I think I can't take a silly more creative. But I think I probably went from having like five or six edge generated images in a piece to like maybe there's one. 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. They do these sponsored deep dives, which are definitely the most unique. And more people started doing them, but like certainly the most unique. It's essentially it's sponsored content that is like a bad you know has a bad word. But I try to make it the best thing. It's ever

been on these companies. Regular sponsorship. Super easy. That's just what you know what well the half the the newsletter's due. 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 love 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 you know, I can get to a big enough audience size that I can like pay rent. Oh, I can get to a big enough audience size that I can sell ads in like pay rent and also be able to afford food. And they that started to get a latte every day. And get a latte every day and not worry about it. And so as a crew, you know, sponsorship revenue grew into that was great. Sponsored deep dyes. I had a couple of companies that were like I love the essays you read about

companies. Would you write one of those on our companies is like a sponsored thing? And I was like I don't know that seems weird. Like I think the audience probably is going to hate that. But I like I'll try it once. And so I did one and people like that's actually like really interesting. And so then I did it again and again and again. And those are you know, you'll always get somebody who reads the piece and is like stop reading in the beginning with soon as I as soon as I tell

that it was sponsored. And like that's totally fine. The interesting thing is like the feedback I get from other founders or 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 trust me with the company's story to pay money for it and three invested like a lot of time and like telling me what they're going for and like giving me access to their financials

and things and 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 like what is a thing that this company does that's unique or the way that they think about the world that's unique or even just like you know, I've written about ramp a few times and like they they structure their engineering team in such a way. I think it's more complex than this now, but originally they're a FinTech company

that also wants to move really fast. And so they have like they hire for engineers who like to move carefully and don't like anything to break and like and like our certain type of person who's like just wants everything to be perfect. And they put them on the core kind of like payment money movement like anything that touches money tea and there's there's that side. And then they have a bunch of like cracked engineers who have won international coding Olympia ads and like they

have multiple of these these people. They've like brought people in for other countries who like 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 like really not the end of the world. And so they can move really, really fast and kind of you know, maintain security and uptime like all the things you need is someone who companies are relying on to move money. And so a little insight like that.

Like this is an interesting way to manage an engineering team at a fast growing company that needs to be stable. People like say that to me all the time is something that they thought was interesting and a piece that I wrote. And I don't think that's access that I'd get without you know doing doing those posts. So I really like them. I'm writing fewer of those just because they are such a huge time investment. But the way that I view filtering those is there's 20 companies

that want me to write one of those for everyone that I do. And so you know, I'm not going to be in that piece being like is this company good or is this company bad? It's like more of the filtering happens in selecting the companies. And then from there it's you know 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 like you know, before I started doing this full time. If you told me like if you would

ask 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 like that would be my life. I do the fund is like one I worked in startups for a while before this. I don't like the idea of like sitting on the outside and writing about things without any skin in the game or without like kind of taking a stance and then putting my money where my mouth is on certain things. So that's a piece of it. And then too like they just

feed each other so unbelievably well. I think one of the underrated things about the combination of writing and investing. It's it's obvious why writing helps on the investing side. It's access if founders read the newsletter that's super helpful. They know I think about the world. It helps there. I think on the other side. A fundraising process is essentially the founder distilling like everything that they know and like the thing that they're willing to bet their whole career on

into a memo or a deck or a conversation with you and like explain. I talked to a mining company yesterday. I talked to an energy company yesterday. I talked to a biocut the biocut company the day before and these people are motivated and like incentivized to get you to understand why they view the world the way that they view the world in like a short a time as evenly possible

or like send you the memo where it's like all right a month to half. Actually everything that I know and try to condense it in this memo and like here you go here's the result of that and so it is all these like behind the scenes works of these really smart people then you don't get access to unless you're investing and so I think that's been really really cool and I kind of a 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 a 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 right of passage is there are so many people in the world who have this core idea. Some of them 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 on the on 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 like 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 you know 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 anything. I read you know this is what's so much fun about having a writer that you

like you know you talk to people like Bill Bryson. Bill Bryson wrote a short history nearly everything 1927 the body it's like these topics are all over the place but they like Bill Bryson and he just explained 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's almost like kind of reframes who you're trying to reach with writer passage or with this podcast and who you're trying to get to write like if write a passage you're trying to find people

who want to write it really is like 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 like the thing that I gravitate towards more and more is like there is this 19 year old genius who wrote this one thing on a

poorly formatted blog somewhere and like what a old mind that I was able to find this then like how do you find all of those people who like deeply deeply deeply understand their thing and get them to get it on paper and like they don't have to be good writers like your job is to

help them become a good writer but like how do you uncover those deep crazy will deeply understand ideas I think that this is the fundamental pivot point that the pre-internet world has versus the 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 who's done an exceptional job is Tyler Cowman yeah he has his emerge adventures program and he writes this idiosyncratic log 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 become 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 the 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 a passage and then it's going to say yeah you know I'm just not here to write something superb I'm like okay then get out just go somewhere else like 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 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 like applications and stuff like that but with attracting and repelling people

yeah even challenge the how do you get them to write something really excellent and it's almost like how do you because I think ideas like you know people or ideas or whatever who get bigger and I've seen this in my mind like you get less weird or you like get less spiky or I can speak

to more people it's like how do you find the spikiest idea and add like variance into the like universe of ideas that people actually get to see because like 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 they're like might make a lot of sense so they there definitely is the great writing piece but I think there's also just like the how do you how do you attract these people who have ideas that will change the way that people think a little bit people who don't write

I think overestimate how important good writing is in the way that like 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 I'll give you the editors we got a bunch of editors I'll give you I'll tell you exactly what to do yeah 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 gonna get there now can we do this a hundred times I don't know can we do one really good piece totally yeah I was thinking this coming into this I listen to the podcast obviously

you know follow a lot of the people that you've interviewed and I'm like I'm actually like I'm just like not that good writer like I don't have a process I don't like you know do you have Tiago on like he's thought about like the whole thing around it so much and

I'm like I don't know like I've tried a fine time between like when my kid stiper needs to be changed and what I have another call and like then I just write something and like I don't think very deeply about like the sentence structure and all of that but I don't think it it in some cases it does

like some people are excellent writers and like you read them for their like their wordsmanship and and all of that but I don't think it matters as much as people think so maybe this is just a PSA that like I can write you can write because like I think it can be intimidating to like hear

writers talk and be like wow like they put so much into this and it's like it's not that like it 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 Senus was that the first long

form piece or was that when you were like no I don't like process at all and I'm just gonna because we did that over like three months and then you went from that to writing one of those every week I'm like what yeah it's interesting I'd I guess where this started was I was at my last company

we brought in an executive and Mooted Lightwords very much and I thought that I was gonna lose my mind and like just at the right time I saw one of your tweets talking to my right at passage so I'm like I'm gonna do you write a passage because I need to do something with my brain you know what you

wrote you said my goal see it 20 newsletter subscribe yeah I tweeted that I needed and it wasn't even a goal it was an assignment for me that's for guys like you needed to get 20 people to sign up and so I like banged a little bit on the internet the first essay that I wrote actually was just like

I think you said like find a writer that you the assignment was like find a writer that you like and like talk about their writing and I chose Ben Thompson and and out of however many people were in that class in our first crew meeting you were like this essay was like the best that I whatever nice

thing you said about it was like oh I might actually like be able to write this is great and so wrote a couple smaller essays through that started the newsletter as the assignment and so every week would send out links it was just like a thing you know I heard burn talk about this idea of

like not wanting to forget things you read and I was like that's that's great like I want to just like 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 like my biggest fear I have a terrible memory my biggest fear is just like just losing my you know my memory at some weight it's like how do I do a better job of capturing the things that I'm consuming and I was doing you know here's what a billboard would

cost and here's what the subway add cost and like trying to break it down I should go have reread that that piece but did a few like kind of 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 that's when I had been obsessed with for a while so wrote that on the side but the seniors piece was I think 11,000 words worked with Tom White as the air and I was so deep in my head on that and that was one where I like really had paralysis around like how much

information how many smart people had thought about like you know 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 in the Scottish and Lightmen or on any number of things that I could have read to make

that piece better and then I just like dump a bunch of words into a doc and Tom would read versions of it was the first time it 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 was maybe

not feel terrible myself even while he was like I don't think you're saying what you want to say here or like you completely lose me you know you know 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 you're 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 whole year than now editor who's like what the heck is wrong with you it's a Corella Deville just like stepping on you and you're just like ugh and that is a terrible feeling or even just be like unclear or like this section is off yeah you know like little things where you're like can you tell me what you're right but like can you just like go rewrite the sentence for me like what do you mean when you say that it's not even rewrite

the sense it's just give me some help it just get me started get me started with some momentum I 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 value you can just tell when Tom's editing like he cares and like really

wants to make it good and it's like mission to make it good with you I don't know what that flipped to me but then yet 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 like

the piece then that I'm working on and it's just like all right I'm doing this every week until like I'm gonna just put as much information in this as I need to it's not gonna be perfect I I struggle with this one a little bit or sometimes like should I just go off schedule at this point

and like just right when I think that I have something interesting to say like a really crafted I have no idea how I would how I would be at that or like you know there's you know if the body of work they kind of like built on each other and piece off each other is the interesting

thing or if like I have it in me to write like you know 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've been not you know I've 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 that one is like I wrote it and this is what I didn't do this all the time I like had a draft on Saturday that I thought was not that good and so like I threw it out Sunday morning and I just wrote that piece in a day like fresh from

my idea to to publishing which even I was like rare that I'll have that Dn rate in a day I was like that's like cool like it's interesting but throw a kind of piece you know paid that I don't think it's gonna 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 it was weak it was the talk of the time and it's still like 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 and I'm sure that they're like really great really great kind of like writers and cultural

commentators who are like I haven't developed the skill of doing this but I think the thing that it did was like was me putting into words the thing that I had noticed that didn't have a name that everybody else was like oh yeah like I also noticed this thing and there's a little bit in

that of there there's noticing the thing and people also just like you know being told how to do something it's like the fact that the great online game like how to think that you can go do and you can go play and like oh there might be like this amazing opportunity on the other side

like if I'd known so many people were gonna read it and like refer to it I actually probably might not have written it in the same way that maybe be embarrassed to say like this is how you should be on the internet because like 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 they get feels like you're just typing things and then like look what what's happened here like 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 you know get to reach however many people you know we're reading that boring at the time it's less than 50,000 people reading that boring at that time as 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 I 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 yep and then I'll write like I do a journal thing with a friend every day and I find that so

much 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 like like this has nothing to do with writing it's about it's so close to me that it it maybe I'll do it later in life you know 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 right on 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 it's the thought of publishing those is terrifying yeah a separate question because I've

been curious about this I be familiar with Jesse Michaels he does American Alchemist he at one point on I've for I think here's on the theory of everything theories of everything back asked and said something about the Bibles is like almost these like codes that were made to

you know the gospels as these like codes they were made to survive over like to be lindi to be transmitted to like 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 you know pep the Jesus parables or you

know the the way that he taught or spoke or anything pepper before and I haven't given it a ton of thoughts since what I think it's interesting the New Testament's 2000 years old do you think we've lost that 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 like 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 you're there's a leap of faith yeah so I'm gonna 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

um 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 gonna 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 said these 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

different John and different writers in the New Testament but this is actually a God thing so it it it's really up to God and not up to man so those are two very different answers yeah that one's that one's hard argue it the non-believer one I think is 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 like it just seems so bland and old and boring and whatever but it was so novel and like so controversial the the things that you know Jesus is teaching and like the idea that you

should love people and the you know the idea that that you know people are worshiping somebody who was killed on a cross in the way that the slaves are the time I'll argument about Jesus it's almost impossible to create maybe not but like to create something to create a set of ideas

that novel at this point just because there's so many ideas like any combination and permutation of things either has been tried or somebody will try and we'll tweet I think that's another challenge to to do it even this wise incredible poet is gonna have a really hard time

shocking the world enough to to stick yeah you know I think that this is 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 because I'm right or because to accept this means to resign to this sort of like 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 something like that they're like no you know 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 they're like oh no I think new I'm on your team on this right like I I am certainly not a believer that we

like the whole point of not worrying is that we have not said and that that things compound on each other and all of these new things are possible and it'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 like all of that I agree with I think I'm probably also being shortsighted on the other side of this argument where just like there is this like weird set of conditions where to your point there was oral history things weren't allowed to be said whereas like now it's just it's not that

like all the ideas are taken it's just like as soon as there's an interesting thing to say a thousand I'd run this exercise as we did about this the other day where I think of something I'm going to be like oh that's like clever phrase and then I'll search it and like thousands of people have said

that thing before and so that there's a little bit of that I think I'm probably being shortsighted on we'll put neural links in it that would be the first great neural link communicator who's like able to speak directly into people's brains or you know like there will be some other

opportunity for that right yeah I you know I'm always I'm always amazed by two things and they're directly in tension with each other the first is exactly what you're saying oh everything I mean I just 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 I know exactly where you got that from I got that from this book this chapter and there's sort of an eye rolling that

comes from it but that man I'll find like one tweet a week and someone will say something and it's it's as if they've unlocked a new feeling or a new way of describing something so they happen yesterday I was reading a essay from Immortals about the painting Nighthawks reading the piece

and he says what's what's interesting about this piece is that the predominant feeling is one of melancholy but like a 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 he says

melancholy but not in a sad way and then he starts starts starts going through it 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 like 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 I kind of know like that 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 like the most the most fruitful place to be looking that that that that fuels your writing process my favorite thing to do every once in a while if particularly I'm feeling stale is to tweet

and ask people for their favorite essays that are like more than up a few years old and I've one time really 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 like five or

10 great essays and different ways people write about things like that just refreshes me and like oh cool like that's that's here right so that's from the 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's with it depends on the piece like some are just like magically written some taken idea that I'd never thought of before and just like go deep on that idea and then you know talk about the world in a different way um what's one of those essays I love the essay becoming

I'm in a magician by auto-translucence great piece I love that piece yeah there's just like it's it's you know it's like almost like ethereal but like you also like really like kind of like love feel it and you're like oh I know exactly what you're talking about where these like people

who are just so unbelievably good at a certain thing like there's just those little ideas but there's a 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 like 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 there's like it's a list of I don't know must be over a hundred essays but like that is one that every time I go back and

what do you think your resume to do so much it like I can't even describe it is just like that that feeling and and maybe it's the other great online game thing where it's like finding something that I'd maybe thought before but didn't put into words and I think that just captures like that

feeling for me so well that I that I go back and you know just just try to get that feeling from the piece more than any particular sense like the way that I think about consuming information is like if I'm specifically researching a piece like I'm just looking for like as much information

and facts and whatever as I possibly can if I'm generally reading I just like I have a terrible memory I don't have like the Benton saying or Bernhobert or Mark Andreessen the three of their brains work like this and I'm not inside the brain but it seems like it from the outside where

you just have like a framework for things like a really strong base such that every new thing that you see and like more capacity burns that they've never got a memory I don't know if I believe that enough but that and it's like you know this framework where anytime you read something you're like

oh that hangs like right there on the frame and that hangs right there and that hangs and mine is just like it just jumbles and like I was upset about it not upset upset is way too strong word but like you know try to do space for petition or try to like remember things and I was like you know

what I could do that and like bang my head against the wall and it's just not like it's 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 like hope that it bangs into each other and creates like some weird idea that just pops out at a random time and so I feel like almost given up on trying to memorize I'm like I would love to be able to do it and I think it's a waste of time for me personally to like really

try to memorize things um and so now I just try to like have well-written things or interesting things or novel and weird things uh they can pop in and bounce around in my brain and hopefully turn into something interesting do you read a lot of books every a lot of books yeah fiction non-fiction

sci-fi I was doing for a little while a little bit less of now but like love just to you know I think for for what I'm writing about and what I do I think there's something interesting about seeing like a thousand year from now ideas or a hundred year from now ideas and like

in happening that world like I think most sci-fi is actually like pretty horribly written and like you read the pros and you're like oh this is like not that good but there is something about happening in the world where that just like assumes that all of the things that seem like

almost impossible right now just happened and then coming back to the present and then seeing like just the ideas that are like a year or two away and you're like oh like obviously something like that is going to happen is this the one or like does the business model make sense right now or the

the cost of inputs to they make sense for this to be a a margin positive business but it's not like oh that's stupid or crazy it's like no yeah like I recognize this idea from the future that this person is trying to build now and so that that's pretty cool as you look at your writing what is

the biggest thing that irks you about it this is something maybe more more self like I wish that I had just like a little bit more technical depth on things probably a little bit better of like understanding of like exactly like the next level down of how something works and I think I have

an okay level for you know for at least rocking what's important about something and then being able to like explain it back and I think that's one of the things that I do well but then there's like that you know if you if you scratch three levels deeper like you you've lost me

uh and just like you know it'll 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 like how how well you have surrendered and aligned yourself to this is who packiest and I'm gonna be that person there have been multiple

moments in this conversation where you said I'm this person so that's what I'm doing I'm not I'm not gonna fight it I'm not gonna fight it I'm not gonna go try to memorize I'm I'm an optimist I'm gonna lean into that because that's how it is and someone might critique that hey my

peace about some company is gonna be optimistic you just did it there you and I think that look this is probably a pre-requisite 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 gonna have

to surrender and say this is who I actually am because otherwise I'm not gonna be able to write piece number 205 yeah I've never I've never thought about it that way but now that you say I did sounds so obvious I've become a lot more at peace and just knowledgeable about about I guess who I am

through writing in the beginning I remember thinking like look if I try to write like very like academic or sophisticated like I'm just gonna get really tired I like I write too much I cannot actually physically do this every like pretending to be someone I'm not in these pieces is actually

just gonna be physically impossible I won't be able to work if I if I do that but you're right like every little while there's like something else that I uncover about myself that I just like don't try to fight and that's probably not like great for audience eyes or grave for like you know

a bunch of these things or it's like this week I'm interested in this like wild biotech company and like the next week I'm talking about space it's exactly what they tell you like not to do audience building wise but it's like I just get so like if I'm gonna put the effort into

write this much every week I want to find the thing that I'm like the most fascinated by I mean a silly choice yeah I mean I you sort of said if I'm gonna do it then I want to write the thing I'm most fascinated by like writing the kind of piece you write every week is hard enough yeah

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 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 like yanking your brain to go follow that totally you know is there anything else for us to talk about I think I mean this was like a little bit of therapy a little bit of reunion this is great yeah that was a good time thanks for coming on man thanks for having me