Transcript: ‘How to Supercharge Your Writing With AI Tools’

The transcript of AI & I with Evan Armstrong is below.

Timestamps

Introduction: 00:01:04
How to develop good taste: 00:04:28
Dan uses Claude to articulate his taste in books: 00:13:34
How to use LLMs to explore art cross different mediums: 00:21:06
The way Evan chooses his next essay topic: 00:33:45
Go from research notes to clear thesis in Claude Projects: 00:38:20
How Evan uses AI to master new topics quickly: 00:46:51
Evan leverages AI to power through writer’s block: 00:59:21
How to use Claude to find good metaphors: 01:04:28
The role of AI in building an audience: 01:11:44

Transcript

Dan Shipper (00:01:41)

Evan, welcome to the show.

Evan Armstrong (00:01:43)

Thanks for having me. Long time coming.

Dan Shipper (00:01:45)

Yeah, I'm excited to have you. For people who don't know, you are the lead writer for Every. So, you write twice a week for Every. We've been working together for about three years—two years full-time. And of all of the writers that we've ever worked with, you're the one that survived the gauntlet and actually became a real writer. And I'm just psyched to have you on—both because I love hanging out with you and getting to work with you every day. And I think you're just you have that sort of rare combination of: you're really smart, you know a ton about business, you're funny as hell, and you actually want to be a writer. And it's just been such a pleasure to watch you go from being, I guess, a professional marketer, SaaS investor—a bunch of different things that you were doing—to now being a pro writer. So, welcome.

Evan Armstrong (00:02:39)

Well, thank you. I'm really excited to do this mostly because I'm going to chop up what you just said and, for my performance review at the end of the year, just play you back to you. That was the only reason. This is just to make sure that I hit my bonus for the year. That's the only reason I'm here today.

Dan Shipper (00:02:53)

I'm costing myself money.

Evan Armstrong (00:02:55)

Yeah, exactly. This is a very expensive podcast.

Dan Shipper (00:02:58)

Great. So, I think what we wanted to do is do a little bit of a non-traditional episode. That's a little bit less like me just interviewing you and more like us together talking about writing because we're both huge writing nerds, we love to write, we're both professional writers. And we're talking about writing, particularly in the context of AI. In each part of the writing process, how are we each using it? And to what effect? Where is it good? Where is it not good? All that kind of stuff. And you're actually teaching a course on this called, “How to Write With AI.” So, it's a good time for us to kind of explore together. And my hope is we both just come out of this, I mean, nerding out about writing, which is probably both of our favorite things to do. But also learning stuff from each other that we can apply to our process.

Evan Armstrong (00:03:46)

Yeah. I think when people picture Every, I think they envision it more editorially cohesive than it is, where— I would say, it's more contentious than people would think. We’re debating this stuff a lot. We're arguing over sentence structure. And I'm going to guess that today we're going to find out we use AI very, very differently in our writing process. Let's hope. I think that'd make a more interesting episode.

Dan Shipper (00:04:10)

It would. It would make it more interesting.

Evan Armstrong (00:04:12)

I think we're going to find we use it pretty differently.

Dan Shipper (00:04:15)

Okay, cool. Well, basically we've split up the segments—or the things we're going to talk about— into four sorts of distinct areas. One is taste: So, how do you know what good is? Two is the topic: How do you pick what you're going to write about? What do you write about? All that kind of stuff. Three is craft: So, that's actually, how do you do the writing? It's everything from outlining to writing to editing. And then four are the audience: How do you reach people?

And we did it that way because that's how your course is structured, and that sort of allows us to get the whole breadth of all the things you might use AI for in writing as a creative, intellectual pursuit. So why don't we start with taste? Can you tee it up? Talk about why taste, why is it important? And, yeah, we'll start from there.

Evan Armstrong (00:05:05)

Yeah, I think taste is a buzzy word and it's also a word that means nothing and everything in that taste is not— My line about this is that taste is not whatever people in Brooklyn are doing.

Dan Shipper (00:05:22)

I'm in Brooklyn.

Evan Armstrong (00:05:23)

I don't mean that as an attack against Dan, but more against the Brooklyn-industrial complex. They made our coffee too expensive and it's all their fault. Anyway, no, I think taste is the ability to articulate why something is good. You may say that you loved Dune: Part Two or you loved whatever latest article either Dan or I wrote, but being able to accurately describe why you liked a thing besides awesome, loved it—that's actually really hard. It's a discernible skill. And I couldn't really do it for myself until I started using AI more. And so I think it's an exercise that everyone who wants to write something good has to be able to say what good is.

Dan Shipper (00:06:06)

And what does that mean to you? What is good for you? How do you articulate it for yourself?

Evan Armstrong (00:06:12)

This is complicated. So, I think when we're talking about taste, you have to be, taste in what context? So in the capitalist context of taste, you're like, is my taste overlining with the problems that my product is solving? So Lenny—who's a friend of ours, he writes Lenny's Newsletter, does a great job. He has these four jobs to be done, and you gotta help me here if I'm missing some of them, but it's like, make me smarter, make me money, entertain me—he describes these jobs. And then there will be taste that goes next to those jobs. I have found that I am very bad as a writer of like, I gotta make a product. I'm just not good at it. I get bored, the writing is crappy. So, instead, what I have found is that good taste is basically things that I enjoy. So, I only write things that I would have a good time reading, and that usually ends up— Anytime I deviate from that, the audience doesn't like it, I don't like it, no one enjoys it. So, good taste is something that I like to smile while reading.

Dan Shipper (00:07:12)

And what do you smile about?

Evan Armstrong (00:07:15)

I think the peak of writing is the more boring the topic and the more entertaining it is, the more skill that's presented. So, you and I, Dan, we write about on one level, very boring things you mostly do, like, tokens. I'm talking about the next token, right? And I spent a lot of time on accounting, here's how finance works—no one cares. No one likes that. No one enjoys that. It's not fun at all. But, being able to crack jokes, to be able to make it accessible and have an energy to it, it's really hard. It's really, really hard to be accurate and enjoyable. And so for me, that's what I shoot for in my own taste, I'm like, is it something boring that I know I should know, but I don't? And I have a good time while reading about it. Very hard bar, but that's what I typically go for. Entertaining reading about boring topics is how I think about it. I'm curious, Dan, for you how do you articulate your taste? Where do you find your taste being fulfilled?

Dan Shipper (00:08:12)

That's a really good question. And I will say also, for me, this was one of my big unlock moments for AI, as I wrote this piece called “What I Do When I Can’t Sleep,” which is about using AI to discover my taste. And it sort of came at this particular time in Every history where we were kind of going through a little bit of an identity crisis—what are we going to be, what are we going to do? And I think I had to go back and think to myself: What do I want to do? Who am I? And both ChatGPT and Claude were incredibly good for identifying that. And I think the things that came out of it, for me, are going through the exercises, using those things to think about who I am and what I like. I really like writing that is intellectually stimulating, it's analytical, it's philosophical, but I really also like it when it's emotionally resonant, it's psychological or it pulls on your emotions in a certain way. I also like writing that's very very poetic and lyrical. So, an Annie Dillard-type person with the running joke at Every is that I relate everything back to Annie Dillard.

Evan Armstrong (00:09:31)

I'm laughing because literally, I think for most of your pieces I have to edit, I have to hold you back. You do not need to mention Annie Dillard here. This has nothing to do with her. You need to cut this section.

Dan Shipper (00:09:40)

I'm a broken record on Annie Dillard, but the Annie Dillard will continue until morale improves. So, I like that. I really like writing that is really accessible, even if it's dealing with a hard topic. So, Robert Sapolsky is a really good example of someone who I think does that incredibly well.

I also really, really love writing that is just practical. It's like, you can actually apply this or how it relates to you, even if it's somewhat esoteric. And I think generally the things that I'm drawn to are very interdisciplinary looks at the human experience, the relationship between humans and technology, the relationships between technology and creativity and psychology, and then sort of philosophy all bundled into that and business all bundled into that are the kinds of stuff that really, really get me going. And it's kind of interesting because it's it's one of those things that if I look back on my life, I can totally see that as a pattern and stuff I've loved for a long time, but I was never able to say it until Claude and ChatGPT told me like, hey, this is what's going on for you. And like you said, saying it, articulating it, it's so powerful because once it's articulated, it becomes something that you can aim at, you can aim yourself at, you can aim other people at, and you can start to refine how you write and what you're doing based on that. And I think that's sort of just this key underlying component to getting better.

Evan Armstrong (00:11:25)

I think it's interesting because for both of our answers there, if I had the stopwatch, I bet we both went on for two minutes. This is what I like, and it's kind of just an amorphous blob of things and emotions. And so when I think about taste, particularly when I saw you, because I was thinking about when you wrote that piece. That was June 23, 2023. After you wrote that, it wasn't that you could suddenly be like, I like Annie Dillard because she's lyrical and so my writing is gonna be more lyrical. Before that, your writing was lyrical. It wasn't like there was some huge shift in your writing, necessarily. It improved, of course, but the thing that I noticed is after you published that piece, you hit a new emotional plane where you're like, ah I am comfortable writing the way I want to write. Do you think that's a fair characterization of that change after you published that piece?

Dan Shipper (00:12:22)

I love that. I think that's so true. Yeah, I think part of it sort of relates to that piece I wrote, I don't know, maybe three or four months ago called “Admitting What Is Obvious,” which is admitting that I wanted to write as a core thing. And I think you're totally right. Articulating it gives you something to aim at and also allows you to incorporate it as part of your identity, which requires admitting who you are, which is actually very scary to do, because it feels like it's cutting off different other avenues that you can take. I like things that are not any of the things I mentioned. I like dumb, funny movies, or whatever, but that's not in my taste, and so that's scary to do. And it's also scary to feel like maybe you'll be ridiculed, like people won't like you if you say that you like this thing that no one else really likes—I don't know anyone that likes Annie Dillard except for me. They're out there, but I don't associate with them.

Evan Armstrong (00:13:25)

The Diller heads unite!

Dan Shipper (00:13:28)

And once you say it and you realize how basically no one cares and the people who do care are like, oh, that's kind of cool. It’s fun to watch someone just like something in public, then you're much more comfortable just owning it and being like, this is what I want to do. And I think you're totally right. It's such an important part of doing any kind of good creative work.

Evan Armstrong (00:13:51)

I'm curious, maybe we should talk about what you actually did in the article, for those who haven't—for the Every heads, beyond our deep-cut fans. What was the AI exercise that you did to develop your taste? I'm curious. Can we do it live? This is the AI & I show.

Dan Shipper (00:14:10)

We'll do it live. So, basically the way this worked—and I did this a long time ago. So, we'll see how well it does today. I'm sure it'll be good actually, but it'll be interesting to see how it updates. Basically I just had this note in my Notion doc. I was just thinking for a little while who do I actually just like as a writer. So, I started adding names and this was not just a one-time thing. It's a continual process because there's all these different contexts in which you're like, oh, I really liked that person, even though you forgot. So for a while I was kind of just updating this and I have Robert Sapolsky, Robert Pirsig. Sapolsky obviously does the really accessible deep science stuff. Pirsig is really accessible philosophy blended with fiction. Ursula K. Le Guin is really interesting psychological fiction. We've got Mary Oliver, that resonant prose. Bill Simmons, who's a very bloggy, funny, clear, simple kind of writer. So I just had all these people, right? And I have words for these people that— I can say all the words right now, but I could never say that before this exercise. So what I did was I just copied this into Claude and I was like, “Hey, here is a list of writers I like. Can you tell me the vibes of these writers in detail?” And then I just pasted my list and I went for it. And I kind of like asking for vibes from a language model—language models tend to do well with vibes—and it sort of gives me this really big list of things. “Robert Sapolsky: scientific, engaging, accessible,”—see that's a word that I used. “Pirsig: philosophical, introspective, Le Guin: imaginative, thought-provoking, feminist, Mary Oliver: nature-focused, contemplative, William James: philosophical, psychological, pragmatic.” And it sort of goes on. And one of the really interesting things here is you can even start to now like to pick out words that resonate with you. I don't know if you see any words here that you're like, ah that is actually something I hope to be.

Evan Armstrong (00:16:31)

I mean I have the highest of standards for myself. I should be all of these all at once. I don't know if you ever get that where I'm like, I should just be the best of every best writer and do it all in my 1,500-word blog post. I'm curious, one thing we should do is— You actually did not do this in Claude last time, you did this in ChatGPT.

Dan Shipper (00:16:58)

I did it in both.

Evan Armstrong (00:16:59)

Oh, you did it in both?

Dan Shipper (00:17:00)

It was both Claude and ChatGPT.

Evan Armstrong (00:17:01)

So listeners, you should know that Dan is a liar because in his post that I was reading this morning, he says ChatGPT.

Dan Shipper (00:17:09)

No, it's, it says, it says Claude and ChatGPT. You didn't read the post carefully enough.

Evan Armstrong (00:17:12)

Oh, oops. No. Okay. Here's the thing. Okay. No, this is—

Dan Shipper (00:17:20)

Don't come at me unless you've got—

Evan Armstrong (00:17:22)

No, no, no, no, no. Now you're changing the truth. You used Claude to do the notes part of the exercise. You didn't use Claude for the writer part of the exercise. Or maybe you did both and you just didn't include those details.

Dan Shipper (00:17:35)

I did both, but I just used one from ChatGPT and one from Claude.

Evan Armstrong (00:17:39)

The key to internet success is nitpicking needless details and starting a beef over it. So, this is what I'm trying to do here today.

Dan Shipper (00:17:44)

This is where it starts. This is how every beef of 2024 starts.

Evan Armstrong (00:17:56)

Yeah, this is how it begins.

Dan Shipper (00:17:50)

Okay. So, let’s keep going with this. So, basically so we've got this big list and you can start to pick out things that you think are interesting, but, to me, it's overwhelming. It's like, wow. How am I going to try to be all those things? It's impossible. So, one of the things you can do, which is really cool— Well, first, before I even get to the things you can do, I would press retry a few times just to see how it does it in different ways. You'll kind of explore the latent space and possibilities here.

And it may come up with different ways of describing things that might be better or worse. I don't think that one was particularly better. Yeah. I think this is slightly better because it's not necessarily citing their most important work, which I think is kind of irrelevant to this exercise. So, I'm going to go with this one and I'll say something like, “Can you synthesize the vibes down into something more compact? I want a summary that can help me express my taste. Do it in five sentences.” And we'll see what it does. What's really interesting about this is ChatGPT, when it does summaries like this, sort of tell me the vibes, and it gives you a big long list at the end. It usually has a summary paragraph that just tells you what it just said. And that paragraph is usually really good. Claude doesn't do that. So, it might be interesting to try this in ChatGPT after this, but ChatGPT—

Okay, it says, “Your literary taste gravitates towards thinkers who blend scientific rigor with philosophical depth, often exploring the intricacies of human nature and consciousness. You appreciate writers who can make complex ideas accessible, whether delving into neuroscience, psychology, or the cosmos. There's a strong current of introspection and mindfulness in your preferences, balanced by a dash of humor and pop culture savvy.” So, aside from the fact that it's like really complimenting me and gassing me up, this is actually really good.

And, for me, right now because I've seen this before, it's not a mind-blow moment. But when I first did it was like looking in the mirror for the first time and I was like, holy shit, this is what I look like, and I like it. And so that's the basic gist of the exercise is find people you like, throw it into ChatGPT, and have it synthesize something.

Evan Armstrong (00:20:17)

Sso you have this list and you've sat on it for a little over a year now. When you're editing a piece or writing a piece, do you ever find yourself mentally going through this checklist of attributes, or is it like— I'm curious how much this actually comes into play during your day-to-day process.

Dan Shipper (00:20:35)

It's not a checklist of attributes, but when someone gives me a piece and they're like, what do you think of this? Or should we publish this in Every? I am kind of explicitly being like, if I don't like it, I get a vibe that I don't like it. And then I can be like, well, it's just not accessible enough or it doesn't have that sense of curious optimism or it doesn't have the depth or the thoughtfulness or whatever. So in that sense, I totally do. And then another way that this works is when I'm editing myself, I do have some of those words in mind and I'm often either thinking about those words or I'm going back and being like, I feel dry. I don't have the vibe anymore, and I know that Robert Spolsky's got the vibe I'm going for, and I'm just gonna reread him. So, I'm curious for you, I know that you've done these exercises too. How are you tasting? How are you thinking about it and how are you identifying it with AI?

Evan Armstrong (00:21:39)

So I think I did it because I read this article. Or, you wrote this article last year and I was like, ooh, I should do that. So all credit to you for this exercise for myself. I didn't come up with this idea. I just copied you—the place that I took it differently is, I think I'm more multimedia than you are when it comes to tastemaking. I love cinema. I love exploring different forms of artwork and I find that informs what I write just as much as anything else, and so a lot of times, I will find the taste notes of what I'm looking for by talking— Well, talking first with Morgan, my wife, who's a humanities Ph.D. And so she has a much better articulation of all these things than either of us.

But if she's busy talking to ChatGPT about it and getting a better sense of if I liked a couple of movies, why did I like these movies? Or, if I liked a couple of posts, what artwork is related to these posts? Because I find that it's able to draw things that I haven't heard of, or I haven't been interested in, and it makes me more well-rounded. I worry when writers are like, I only read, because I think you can get in a little bit of a rut. Personally, I get into a little bit of a rut, and so I think it's important to be multimedia with your taste making. And so ChatGPT helps me do that.

Dan Shipper (00:23:15)

I'd be curious how you do that.

Evan Armstrong (00:23:18)

So read out to me five of the writers that you love right now, and make sure they're ones I can spell.

Dan Shipper (00:23:28)

Okay, cool. I'll give you a little bit of a list. And actually, before we do that, can you just introduce the exercise that you're going to do? Tell us what you're going to show me.

Evan Armstrong (00:23:38)

Basically my goal is— Those taste elements that you'd pulled out in your exercise where it was philosophical or lyrical. I think it's really interesting when you say, I like lyrical prose. How does that apply in other mediums? Because not necessarily— Lyrical is obvious in, say, a poem or in a song, but are there lyrical paintings? Is that a thing? And so, my big thesis when it comes to taste is that it's a blob of emotional permission to like what you want to like and it's not constricted to certain types of medium. So, it's not just writing. Being a great writer and having great taste as a writer does not mean you only read the best books.

It means you partake in the best movies, the best films, music, whatever it may be. So, what I want to do is take the list of writers that you have and then try to convince you to watch a movie because I've known you for years. I've given you like 20 movie recommendations. I think you've watched zero. So today we're going to fix that. We're going to fix it, Dan. If ChatGPT tells you, you'll do it. If I tell you, you ignore it. So, we're going to have ChatGPT do it for me.

Dan Shipper (00:24:53)

I love that. I also would like to do that with you too, just to see what we get. Because I really want to explore your taste too. So, let's start with what you want to do. So, yeah, let's pull up ChatGPT and we can see what it says.

Evan Armstrong (00:25:08)

Okay. So, Dan, who should I put in? Just give me five.

Dan Shipper (00:25:12)

Okay. So, I mean, we've already talked about Annie Dillard. I have to have her on any list. I would say Robert Pirsig. A more recent one is this guy H.D.F. Kitto. He's a classicist. He writes about Greece. He's amazing.

Evan Armstrong (00:25:28)

Is it kiddo like—?

Dan Shipper (00:25:30)

K-I-T-T-O.

Evan Armstrong (00:25:32)

K-I-T-E-O?

Dan Shipper (00:25:32)

K-I-T-T-O.

Evan Armstrong (00:25:34)

I like kiddo. K-I-D-D-O, but that's not right. Okay.

Dan Shipper (00:25:39)