David Perell is known as “The Writing Guy” on Twitter, but did you know his email newsletter has over 40,000 subscribers? Not only that, but he sends THREE newsletters a week… every week! 

In this in-depth conversation, David shares exactly how he uses Twitter to grow his audience, how he maintains consistency with such a high rate of output, and how he’s built an amazingly profitable business by monetizing his newsletters with his breakthrough writing course.

We discuss the top 3 ways for a writer to make money from their work and reputation. Should you: 

• Become a consultant?

• Sell courses?

• Start a company?

David breaks down when each model makes sense, and whether people like Ben Thompson of Stratechery would be better off starting companies instead of selling paid newsletters. 

David explains why new writers should focus on quantity over quality—and when to flip that around. He also covers the small tweaks that turn your articles from flash-in-the-pan to evergreen. 

You’ll learn what to focus on when you’re just starting your newsletter, and the language to use on subscription forms to get people to sign up (hint: it’s not, “Sign up for my newsletter!”) Plus, how David sends 3 newsletters every week with less than 2 hours of work!

Episode Transcript

David: [00:00:00] This is one of the things I think a lot of people get wrong about getting more email subscribers is they’ll say something like sign up for my newsletter. No one cares. I say something like you will learn how to take ideas and then turn them into structured writing. Then you will learn how to distribute that structured writing.

And then you will learn how to build a system to do this. It’s very specific and it’s very useful to the reader in so far as you have those three things, your conversion rates will go way up.

Nathan: [00:00:34] Today on Art of Newsletters, I’m joined by David Perell, who has an incredible newsletter that he’s grown to over 40,000 subscribers. We dive into how he uses Twitter to grow his audience. He blows my mind with what he does on Twitter. we had a new, his research processes, how he sends out three newsletters a week really consistently.

And then the biggest thing is how he monetizes list. he just makes an incredible amount of money off of the courses that he puts out there really, really high quality. And I think it’s a great model for anyone looking to build their audience and earn a living from their audience in particular. So with that, let’s dive in.

All right, David, welcome to the show.

David: [00:01:14] Thank you, Nathan. I’m a huge fan of both you and the company that you’ve built. I ConvertKits one of the most important platforms in my life. And thank you very much for all that you do.

Nathan: [00:01:26] Oh, that’s great to hear. Well, I’m excited to share a lot of your story. We’ve known each other.

What? Only a year or two. Maybe not, not that long, but I dunno, we both admire each other on Twitter and you know, I see you post stuff and I’m like, Oh, That’s an idea that I had, but phrased way better. So I’m excited to tell your story and to share a lot of the tips and tricks for building a billion newsletter.

Why don’t we start just tell people about the Write of Passage, your newsletter, you know, kind of like give the high level view of the newsletter and your business and how it all works.

David: [00:02:03] Yeah. So the way that I think about newsletters is that I guess I would segment it into two buckets. The first is the weekly newsletters that I send, which are Monday, Wednesday, and Friday, Monday is Monday musing, sort of a update of my life.

And just the coolest things I’m learning. Wednesday is a email that comes out with every podcast that I publish. And that is quotes from the podcast links to YouTube videos. And then Friday. Is four or five links that I find every single week and that those are really the weekly ones. And then there’s a whole other thing or element to how I think about newsletters.

And I run a writing course called Write of Passage. And whenever we open for enrollment, which is twice a year, we have 10 days to basically take emails and. People who have signed up and said, Hey, I’m really interested in this. And then other people have just been following along. We might be able to tip over the edge and we have two enrollment periods to get them in the course.

And so for that, we use more advanced tactics like lead scoring, which we hadn’t had as native integration, which you have now in ConvertKit. And then also just sending out a very. Detailed and rigorous series of emails, mostly through the sequences tab. And then just through daily emails that we send to people who are interested in taking the course.

So that’s how I really think of it. It’s the weekly emails. And then when things get really crazy leaning on ConvertKit, to make sure that we get our emails sent out to prospective students.

Nathan: [00:03:46] Nice. So if we go and actually, if you wouldn’t mind sharing some numbers, what’s the, like how many subscribers do you have on the newsletter now?

And, and if there’s any revenue numbers, you’re okay with sharing.

David: [00:03:58] Yes. So we have 43,000 subscribers on the newsletter. And then for students, what we do is about 600 to 700 students a year, then the course. Is $3,000 as of now for the premium or for the standard edition and then about $5,000 for lifetime access.

But we also give about six figures in scholarships every single year. And so you can do the math there and it’s also growing so fast that any revenue number I gave now would basically not be valid in six months.

Nathan: [00:04:34] Yeah. That’s a good problem to have. I like that. That’s set up. So let’s go back and. You know, when you’re looking at first starting an email list or first starting a newsletter, what made you go down this road?

What was the spark that said, like, this is a good way to spend my time.

David: [00:04:51] Yeah. Everybody, who I spoke to and trusted, basically said something along the lines of at the end of the day, when it comes to selling products online, everything is in consequential except for the number of email subscribers that you have.

And I took that to heart. I started off on Twitter. Been trying to grow my YouTube channel, but email was the place where I would always be able to meet people. People check their emails very religiously. And also email is really good for retargeting people. We’ve never spent a cent actually in any kind of paid marketing affiliate or any kind of retargeting, but eventually down the line that might be an opportunity.

And having email makes that a lot easier. And then also. One of the things that was really important. I started off using sub stack and what sub stack didn’t give me was the ability to segment my audience. What happened when I first started selling, read a passage was say, I had 12,000 people on the list, but not all 12,000 of those people were actually interested in taking the course and say that you take 30% of my list.

They’re the people who are really interested in being students and write a passage, but the other 70 just don’t care. And I want to still be able to email them and I want to build relationships with them in whatever way, shape or form. But for those 30%. I want to be able to send them a lot of emails and actually they want to receive a lot of emails.

It’s not just me spamming or anything like that. They’re actually really curious in learning about the course. I got an email today. Hey, can you send me more email about what’s happening? And what I then saw was that I could segment my audience and basically say, these people are interested in this.

Those people are interested in that, which then allowed me to create different avenues depending on interest and what people wanted to do for my audience.

Nathan: [00:06:39] Yeah, that makes sense. So I’m a little torn on which way to go. We can talk platforms, which I want to get into. and maybe we’ll do that in a second, but in those early days, like, let’s say zero to a thousand subscribers, like, what was that process?

How did you pull that off? And then what, what did you learn from that on what you’d recommend for someone else? Just starting out?

David: [00:07:04] Let’s see. So I think that the beginning is hard because. There’s there. There’s this idea from the Bible called the Matthew principle where the basically it’s the rich get richer and the poor get poorer.

And I think it’s very similar with. With writing email. you see the same thing in society now where there’s a lot of people who struggle to make it. And then there’s people who are in what I call the dividend class, where they’ve invested so much, that they basically just live off the dividends of their investments.

And then all those investments continue to compound. This is a lot of how endowments work at universities. Right. there’s There’s actually something very similar in terms of. The way that building an online audience works. Paul Graham has this famous essay called do things that don’t scale. And when you start off, you actually want to do things that don’t scale in the same way that you would do with a startup and you are actually talking to people and you’re out at dinner with them—you’re saying, Hey, can you sign up for my list? I’ll literally sign you up right now. Or you’re Just posting, posting, posting all the time. And you have that email subscribe form at the bottom of every single page. You’re just trying to get the next subscriber, trying to get the next subscriber. Actually I think a lot of people, they start sending emails too early, but then they start capturing emails too late.

And what I mean by that is when you only have like 500 subscribers or something. Maybe even 300, I don’t know if it’s actually worth it to spend two, three hours every single week, trying to send out your weekly email, but what you should do from the second you start writing is you should start capturing emails and whatever you can do to do that, you should absolutely do.

One of the most common regrets I see on the internet is people say I started collecting emails way too late, and it ended up costing me millions of dollars in terms of potential revenue down the road.

Nathan: [00:08:55] Yeah. We’ve heard that from Pat Flynn and tons of people over the years. I mean, that’s actually a conversation that I had with Tim Ferriss.

Maybe, I don’t know, four or five years ago. he was capturing them who isn’t doing anything with them. And so they, they had the list went cold and, you know, he had to almost start from scratch. so in that time period, when you are capturing emails, but you know, you’re spot on that, right. You know, writing this Epic newsletter to 11 people was probably not the best use of your time.

What. What do you do to actually, you know, scale that, to go from, say the, maybe you get the first 25 subscribers from friends and family. what was that next step for you? Was it writing Epic posts and getting those shared or more direct outreach or what.

David: [00:09:40] Yeah. So it’s always a little hard to track, but one of the things that I would say is because you do bring up a good point about subscribers going cold.

You don’t want that. Right? And so the way that I think of emails is much more like a postcard. People think of emails. It’s like these big themes, it’s like a big project. And honestly, people should spend way more time writing books and essays that stand the test of time. Like your book, Authority, is just as popular now as it was, I think in 2012, 2013, when it came out and.

Then what you should do with your emails, sort of like what you do, right? It’s like really simple. It’s four or five sort of blocks and sections, and it doesn’t take you that much time. It’s really just like, Hey, thinking of you, you know, you should think of me. This is what I’m up to this week. And I read it honestly.

I don’t read most of the newsletters that I get, what they are for is basically, Oh, Nathan Barry ConvertKit, top of mine today. Oh, James Clear top of mine today. And you basically get these pains, which then, because you’re top of mind in all these people’s minds, you’re basically creating this digital serendipity for yourself, which is the point of writing online.

And what you do when it, what I did when it came to growing my list, was there a couple things I started off with lead magnets, which are. Which ended up actually not working out as well as I wanted them to basically people trading an email address for some kind of artifact. What worked really well was courses.

And that’s because Twitter is the main distribution channel for me. So what I try to do is I try to build my Twitter audience and then basically convert some percentage of people. Follow me on Twitter, into my email list and. What I found is that I’ve had seven day courses on writing. I’ve had a five, I have a five day one on how to use Twitter.

And I find that those convert really well. And they also are just so much more helpful than a lead magnet. Part of the reason why I wasn’t that excited about a lead magnet in addition to it not converting as well as I just wasn’t excited. It didn’t feel as useful to the reader as some kind of email course that I poured my heart and soul into.

And. Now, what I’ve found is it hasn’t plateaued, but the growth is sort of linear. And what I’m seeing is the people who are sort of in the next grade of email subscribers, they tend to be pretty direct about asking for emails. Like you go on the front page of James clear site and it says right there, you can download a free chapter of my book for an email address.

And then you’re on the page for probably 30 seconds. And then there’s a full-screen pop-up and. I’ve had to think a lot about, okay, what do I want, how far do I want to go in terms of asking for emails? But look, my site will do more than 2 million visitors this year, and I don’t think I’m converting enough of those people.

And so the courses they’ve done well, but I want to continue to do a better job of capturing subscribers.

Nathan: [00:12:31] Yeah. It’s an interesting balance, you know, and like James is also on ConvertKit and I know him well, and he’s got a specific subscriber number in mind that he’s. You know, targeting and close to hitting.

And so I think that’s part of the reason for the aggressiveness, but it also plays a big deal into the next book advance. And, and the next thing of when you’re like, I have a hundred thousand subscribers, I have 500,000 subscribers and then the publishers are like, hi we’d like to talk, you know, and, and the checkbooks come up.

And so,

David: [00:13:01] yeah, yeah, yeah. I call this the paradox of book publishing publishers want you. To have a audience of millions, of people who visit your site every year. They want you to have an idea that is proven to resonate, and they want you to have a big email list. But the problem is when you have all three of those, you don’t really need a publisher.

And so, and so the same things that publishers want is the same thing that makes it. So having a publisher just isn’t as important.

Nathan: [00:13:28] Well, I think you brought up a point, if we go back a little bit to the content of what you send your list. cause one thing that I do is I went to only sending when I had like a big article to write like my ladder is a wealth creation post.

And so what that meant is that I would email my list five times a year, maybe, which is terrible. Don’t do that. Like, unless you, I guess you’ve set that expectation then maybe, but I still wouldn’t recommend it. And then it felt like all the way on the other end was send out like a bulleted newsletter of like I’m going to be consistent no matter what.

And so what I’ve tried to do is find the hybrid of that, where I’m showing up every week at the same time. And then when, you know, with these are the four things I’m interested in, you know, the books, creators, you know, resources, new convert, kit feature, any of that. And then when I have one of those big, long form posts, that is the entire newsletter.

Yes. And if I was more on top of it, it would be like Epic essay once a month, you know? And then the other three Tuesdays of the month would be bullets or, I mean, ideally every other week or something like that. And because writing is not my primary focus that enables me to stay in contact with subscribers, stay top of mind without having to be like.

You know, have the content machine ready to put out an ethic essay every month or sorry, every week, which I’m, you know, I’m my, my day is just not set up to produce on that level.

David: [00:15:01] Yeah. And I think that also once you get to your stature, the actual thing that you should be producing changes. So when you first start out.

I recommend to everyone, just go for quantity, publish all the time and get to a place where you’re publishing every single week I have a friend named Nick Maggiulli He was working at a litigation consulting firm in Boston in 2017, new year’s day, 2018. He looks in the mirror and he says, I am going to publish. Every single week and I’m never going to miss a week since that time—it was actually since that day, he has never missed a single Tuesday. He’s now the chief operating officer at one of America’s top investment advisor firms. that newsletter has. Truly changed his life in terms of every single week being able to produce something. But I’ve been talking to Nick—and I’ve been seeing it in myself because I just published 50 articles in 50 days.

And so I felt what that was like, but I think that something begins to shift later on. Once you have that reach, once you have that distribution and once, you know, That you can write well, and you’ve learned the mechanics of what you need to do from a systems process, from a consumption process, from a production process, what you need to do to write.

Well, I think that. You want to shift more into quality, then when you do publish something, everything becomes exceptional. And that’s what I saw on your ladders of wealth creation posts, which will be read for the next decade. that’s then what you optimize for. And also that’s what I’m trying to do more with long-form essays.

I want to begin to be more like have a Paul Graham or a Tim Urban at Wait But why consistency? And I think that. For that, especially with the kind of work that you do, which is at the frontier, you’re talking with really high level people, which is what you get. But what you lose is you don’t have the time that creators like myself do.

And so what I would advise to you, and I think that it’s actually what you’ve been doing is publish fewer things of exceptional quality. And when you publish them, make them a big deal.

Nathan: [00:17:18] Yeah. That makes sense. And I think that there’s a lot that goes into that, of. Like a couple of these articles, I guess I did it with ladders of wealth creation and the billion-dollar blog and a few others.

When you come out with them, you treat it like a product launch. Like if you take this approach of I’m going to write six incredible essays this year. Yup.

Then you don’t get to just be like, I hit publish. I posted it to Twitter and I moved on and said, you have to say like, okay, what if this is the most important feature that ConvertKit came out this year?

Or this is the level of. I maybe it’s not me trying to hit the New York times bestseller list with my new book, but it’s like, you know, I just wrote a self published book that I really care about and I’m getting it out there. Like what’s the version of putting it out there and really promoting it, you know, actually emailing 10, 20, 30 friends or texting people and saying, Hey, I wrote this, I love your thoughts on it.

And making it like this real promotion and launch, rather than trying to write something Epic and then put it out there and be like, eh, I guess it just didn’t resonate. It’s like, So that it didn’t resonate. It’s that nobody actually read it because you treated it like, you know, Oh, I’m not a full-time writer.

I’ll just put it out there. So that’s what I’ve been trying to do of when I put in the time on the creation side to then also put in the time on the promotion side,

David: [00:18:37] I think that one of the things that’s been very surprising to me in writing a newsletter is. How much churn there is. And I don’t have particularly much churn, but there’s actually a psychological block there in that when you first start writing, you’re like, say that someone follows you on Twitter or someone follows you on Instagram.

You just have no idea who that person is. When someone unsubscribes to your email list, it’s like their email is right there and you can look at it and you can interpret that as. I don’t like you nor do I care anymore. Your work is trash and there is a certain just consistency. You just push through that.

I know that every Monday I’m going to send out my Monday musings too. 40,000 people. And like a hundred of them will unsubscribe. And actually in terms of the grand scheme of things, that’s a very good lack of an unsubscribed rating. But at the same time, it’s still a hundred people who have basically said, we don’t want to hear from you anymore.

And I got to deal with that every Monday. And. At the same time, there is the balance of how you continue to grow sort of in advance of that and get more subscribers than you lose every week. And there’s something to that that just sort of has to become second nature. You know, even this morning, I started off in a course by my friend, Allie, aldol on how to build a YouTube channel and.

It’s amazing how there’s like these ladders of difficulty. And at first you might struggle with perfectionism or you just don’t feel like, you know how to write. And this is sort of like what I would call like a level two struggle of realizing that a lot of people won’t resonate with your work and that’s okay.

But email makes that very visible.

Nathan: [00:20:31] Yeah. It’s I guess it’s the pro and the con of email. Right. You on one hand, you have that personal connection. People can reply or whatever else. And then, you know, the opposite is true. That if they’re like, Nope, I’m out of here, then that’s, that’s just as visible. And I remember, you know, in the early days of growing my list of looking at who wants subscribed and who opened and, you know, luckily once you get past a certain level, you don’t pay as much attention to those as, as much, it’s still totally a thing.

one thing that. you mentioned earlier that I want to dig in on his email frequency, right? You’re sending three times a week. You’ve got different different styles of content that are going out at each time, but I’d love a little more of your take on, you know, how often should you send to your list and then how do you find that balance between, you know, only sending great content versus showing up consistently.

And then as you talked about in the unsubscribes. The more you send, the more people are, you know, tend to unsubscribe.

David: [00:21:36] Yeah. So lots of ideas here. So first of all, I think that the increased. Relationships that you build with the people who you send more often to far outweigh the number of people who unsubscribe.

Yeah. Look, the number of people who aren’t. It actually just doesn’t matter that much. Like if you, if I was emailing someone four times a day, like it’d be different, but those people have just basically said, you’re not for me. And that’s fine. Like, it actually doesn’t bother me at this point. But what I really optimize for is the number of people who love my stuff and they want to hear more from me.

And I think that when it comes to email, let’s just, I’ll give you the premise that what you can do is you can have either B consistency. Or B content, and then you could have a content, a consistency. I think that out of those sort of pieces that you could pick from, I would go for B content with A+ consistency in my entire life of publishing a newsletter.

I have never once missed a Monday musings or a Friday Finds in hundreds of weeks. Not once. I did it today. it’s ritualistic for me now, in terms of the different kinds of content I call this burnt-ends content. And in the 1970s, there was a barbecue joint in Kansas city. I think it was Joe’s Bar-B-Que And what they would do is they would make the brisket and then there’d be the burnt ends at the end, they would throw them away. one day. There was a big line at Joe’s and the owners of the barbecue joint went out to the customers in line and started giving them the burnt ends And the customers are like, these are delicious.

What did you make with them? And they were just like, Oh, this was just the residue. Of the brisket and we would have thrown it away. Otherwise we would have done anything with it. Now we’ll give it to you. Last year, I went to Joe’s and the burnt ends are the first thing to sell out and the most expensive thing per pound on the menu.

How does that relate to writing newsletters? Every single thing that I write in terms of newsletters is the burnt ends of my intellectual life. On Mondays. I share the coolest things I learned this week. Those I already learned—I spend no extra time actually learning them. All I’m doing is compiling them into some kind of place.

And then I send it out on Wednesday. My assistant actually writes the entire email because what I have to do is I have to fill out a notion page for every podcast that I do. And from that notion page, we take. That. And the transcript we produce for the site, we have a way of compiling it and it goes right there.

I do a quick review and we send it off on Friday. I share my favorite links of the week, but I do no extra work to go find those links. I’m already reading them. All I do is type up a summary. And so I think that this is really key that I send three newsletters and spend less than two hours a week on those three newsletters, because it is all burnt-ends ideas.

Nathan: [00:24:46] Yeah, that makes a lot of sense. And I think that’s probably the biggest thing that differentiates these creators, who are able to stick with it for years. like what you’ve done, like so many, so many other people have done from someone who’s like, I’m going to start a newsletter. sub stack is trending to convert it as trending.

Let, let me spend something up. It’s super easy. I get five weeks in. I’ve got, you know, a hundred subscribers turns out it’s not for me. Nevermind. Let me shut it down. Is that. Like everyone’s looking at the work and they’re totally missing the system behind the scenes that creates it because if you’re coming every Monday, so the newsletter goes out at, I dunno, 10:00 AM.

And every Monday at eight you’re like, shoot, what am I going to send today? Like, that’s a problem. But if at the same time, there’s the system to bring up, you know, writing and research, or even just throughout the week. You’ve been saving things too. Instapaper or pocket or, you know, bookmarking then you’ve got all of these resources and you’re just scrolling back and be like, Oh, what’s the most interesting thing that I want to share.

And it turns a, you know, a painful, stressful problem into, you know, just a casual way to interact with readers.

David: [00:25:57] Exactly. It’s all these systems and you just get to a place where it sort of just files in with your life and you just. Read something or hear something said perfect. That’s for my music.

Perfect. That’s for Friday funds. And then you then create more assets. So one thing I do every single year—it gets me every year, three, 3,000 4,000 email subscribers I take all the coolest things. I. Posted in Monday Musings for the week, then I have this intuitive track based off the email responses that I get, which ones were the most interesting then I compile all the most interesting ones from every single week into a giant document that gets more than 100,000 views every year.

Then at the top, I say, subscribe If I have a 4% subscribe rate. That’s 4,000 people. Then I just did the same things with my Friday Finds I was looking today on ConvertKit I have a 5.68. Conversion rate from people seeing the form into subscribing. then I just add to that every single week I share it repeatedly.

And it then just becomes a bunch of these systems. And I think that this is one of the things that is crucial is to get less ephemerality out of the work that you’re doing. And you can just have very small tweaks and things to then take something that is only valuable today—next week, the week after—small tweak here, small tweak there, all of a sudden you have something that’s going to be relevant for a long time.

So for example, you could say. Say that you’re talking about politics, and you could say how to write a speech, a really good presidential inauguration speech that will only be relevant for a small time. Then maybe it’ll be relevant every couple of years. Or you could say how to write a really good political speech that will be relevant 50 years from now, every single day during that time.

it’s just small tweaks and framing that then allow you to get a lot more leverage out of the time that you spend, in investing. We talk about return on investment for every dollar you put in. How much then do you get out in creator mode? We should be talking about return on attention for every unit of attention you give.

How much do you get out?

Nathan: [00:28:06] I like that. if so we’ve talked a lot about the newsletter side of things. What do I want to go deeper for like those long form essays? And you talk about like these essays that stand the test of time. that’s harder to do. That’s another level of research. And so like pulling up these examples of Joe’s barbecue and things like that.

Right. You, you know, I imagine those came from research. So I’d love to hear more about your process for, as you are writing this essay, you know, to be able to pull from your research and pull in the perfect example or another story, like, how do you actually go about. Creating that system.

David: [00:28:43] Yeah. So let me just start by saying this is incredibly difficult and writing these long form essays.

I do them because they’re at the frontier of what I can do and. I’ve had to build years of expertise, writing all these short ones to then be able to write the long ones. And because they’re at the frontier of what I can do, I know that there’s not a lot of competition there in terms of being able to write something exceptional, but also every single one I’ve written has changed me as a person.

The Peter Thiel essay that I wrote sort of overtly was this essay about who is this famous investor? Who’s very controversial and how. Does he see the world differently? And what that was for me was having a lot of people. Talking to me about Christianity and me trying to figure out what my own relationship with Christianity was through an individual like Peter.

And in that essay saying, no, he’s not just a great investor. Then the people who kind of understood him said, okay, he’s not thought that, Oh, he was really into this idea called mimetic theory. And I said, no, actually it all comes up from Christianity and. Then I wrote What the Hell Is Going On?, which came from a difficult conversation.

I mean, at the Thanksgiving table where my entire family didn’t have the language to understand the world. And right now I’m writing an essay on how to save the liberal arts, because the trajectory of education is leading to education. That’s very vocational and not one that’s more contemplative and.

Each one comes from this burning desire. Some question that I have that I need to answer that crucially either no one has answered. Or a question that everyone is asking everyone thinks they’ve answered and have the wrong answer too. And so provided that I can find that I then write these essays, which are these sort of multi-year projects.

Sometimes. Usually I’ve done a lot of the research in advance and I’m probably 70, 80% of the way done with the research in advance. And then I begin to compile that into a central repository. He gets so many notes that I can’t help, but write the thing. And then I sort of take those Lego blocks tournament to sort of puzzle pieces and then try to piece this thing together.

And each one takes me hundred, 200 hours, but they are the most popular things I’ve ever published.

Nathan: [00:31:15] Mm. Yeah, I think it’s, it’s one of those things that. I find, I have to have those systems for logging examples in the stories in order to even be able to set, like, to make that possible. And but I think what you’re talking about is it has to first live as a question in your mind, like this thing that doesn’t quite make sense about the world, or you tried to explain to a friend and you totally botched it because you realized you don’t fully understand it yourself.

And any of those kinds of things. Then once you have that logged, it’s sort of like, it’s easier to find examples and fill it in.

David: [00:32:00] Yeah. I just want to sort of build on that. I think that that’s both the beauty and the struggle of this craft, which is these. Intuitions that no one can confirm or deny.

And you just trust yourself and you just sort of stubbornly March and say, there’s something there. I know it. And then you talk to people and you actually can’t articulate what it is that you say. You can only listen to what you feel. And like my next long form essay after liberal arts is. How time created a culture of anxiety.

And so I’m going to go back sort of through the history of the invention of the clock and look at how the clock is the fundamental technology of the industrial revolution. It wasn’t the steam engine. It wasn’t the train. It was the clock. And talk about how by splitting the world into these discrete units of seconds and minutes, and then taking us away from these naturalistic patterns of life, rising with the sun, going to sleep with the stars in the sky.

Working during the summer. This is why we don’t have school during the summer because we needed kids to be on the farm for the harvest. Right. But now we are much more aware of the clock like you and I today we start at four 30, we end at five 30 and that’s fine, but it creates this sort of fiasco and stress of always needing to be at the next place and the world isn’t sort of naturally like that.

And so. I obviously haven’t articulated this as much as I would like to, but I know that there’s something there and having that intuition, it there’s this certain self-trust that you need as a creator to say, okay, now I’m going to walk and follow that.

Nathan: [00:33:44] Yeah, that makes a lot of sense. And so I guess if I were to give specific advice to someone listening, it would be.

To pay attention and like be attuned to the things that stand out to you of whether that’s a question or something that you’re trying to explain and you can’t quite do, or that someone else says, and it just doesn’t sit right with you where you’re like, I’m not going to dive into the debate with you because I don’t understand what I think yet. Right. But I think you’re wrong.

And I’m going to make that note in my journal and research it more. And those are the kinds of things that when you write about that, that can have such a big impact, like on the billion-dollar blog post that I did, that came from a conversation with someone where they were basically talking about how influencers couldn’t build real companies.

And, you know, they would always be selling just selling attention. And I like had one or two examples of where that wasn’t true, but I didn’t yet have a framework for like, okay, what is true about how you transition from right. You know, an influencer who’s just like renting attention to someone who channels that into.

You know, a hundred million dollar you know, liquor, empire, or a beauty brand or something else. And so when those questions that there, those are the best things that when you dive in you can create an like, turn it into a real essay.

David: [00:35:12] Yeah. And I think that there was also something there for you, right?

This is a question that say ConvertKit does I think 20, $25 million. Last time I heard an ARR and. Now for you. I mean, that’s subscription money, so it’s like really sticky and that’s really great. But then for you trying to sort of ladder up this platform and your own story of writing for designers and then the founding this company, right?

Like there’s a, there’s a reason that you would write this essay. Not any stranger on the street. And I think that that’s important to that. We sort of feel called to write these posts in whatever way it is. And as you were talking about those conversations, there’s a word from the world of art that I think describes this really well.

And it’s the word resonate. And what resonate implies. It’s not just, I connected with something. Like if you see a really beautiful piece of art and you resonate with it, it actually hits your body before it hits your mind. It’ll give you the chills. It’ll make you shake. It’ll have your heart. Racing faster.

And if an idea repeatedly does that to you go write about it, go figure out what it is that is calling you. W what is your body telling you? And so I’m always sort of listening to the world for what resonates and trusting that sort of intuitive instinct for what I vibe with what I connect with. And then.

As long as it sort of relates in some way to what I was talking earlier about some kind of question that everyone’s asking and either people have the wrong answer to, or don’t quite understand if I can find those too, then it ends up being a really fruitful path for. Where I can direct my attention.

Nathan: [00:37:01] Yeah. That makes a lot of sense. Well, let’s turn our attention a little bit to list growth. You mentioned earlier that Twitter is the biggest platform for you, for distribution and new subscribers. Take me through your process there. What works for growing your audience on Twitter and what would you recommend?

David: [00:37:18] Yeah, so I think that list growth is honestly the biggest place where I have opened questions. And I think that that’s important because. Marketing in general is the things that work don’t always work forever. Like at some level, like building an email list will be a smart strategy for the next 10 years.

I know that, but the best way to grow an email list will often change. And one of the things that I’ve found that works really well, and this is what I do in terms of the actual, very tactical implementations of what I do online. It said, look for things that are working now. Where I have an advantage and that are working sort of disproportionately well and work well with how I like to create things.

And what I like doing is creating Twitter threads They’re fun. They take me like 45 minutes, they crush. And if I have a good one, it’ll get more than 1,000,000 impressions. And so I can know that if I get 1,000,000 impressions and I link to. One of my courses, the conversion rate on that is going to be 1 or 2% and that’ll lead to a solid 1,000 2000 subscribers.

And the challenge is with Twitter threads. It’s sort of like what we were talking about earlier in terms of systematizing and trying to sort of get things beyond you. This is about as labor intensive as it gets in terms of you have to earn every email subscriber, which makes it pretty intense at the same time, though.

It. With my reach on Twitter. I know that if I write something good, there’s enough seeding the distribution that it’ll spread and it’ll flow. What I do is I will reply to myself in tweets with the link to the course and crucially, what I do is I, this is one of the things I think a lot of people get wrong about.

Getting more email subscribers they’ll say something like sign up for my newsletter. I send one to two emails every month and you will get them straight in your inbox. Right. Very generic. And no one cares about, about your one to two emails. They want to know what are they going to learn and how are they going to improve by virtue of signing up.

rather than saying, you’re going to get one or two emails. I say something like. You will learn how to take ideas and turn them into structured writing. Then you will learn how to distribute that structured writing, and then you will learn how to build a system to do this. Okay. Now that’s very concrete.

It’s very specific and it’s very useful to the reader. Insofar as you have those three things, your conversion rates will go way up.

Nathan: [00:40:07] I think that’s great. And I mean, the call to action that you specifically mentioned of the free course. Is so compelling because it’s, it’s not this generic, like sign up for, to get more content and you can do the Haven, you enjoyed this threat.

I write about similar things here and like that’s far better than nothing. but yeah, if you have the specific call to action, that rolls from one thing right into another, it works really well like years ago. And that was probably 2013. I wrote this article for smashing magazine, which is a popular. design blog, and it was titled how to launch anything.

And it, it was long. It was a really long article for me at the time. Cause I usually wrote like one to 2000 word articles and this one was like 4,500 words. And I was like, Whoa, look how long this is. And now obviously like so many people write way longer individual articles. but I tried to put everything that I had into that article.

And then at the end, I said, Hey, I don’t want your education on product launches to end here. And so I put together this free course, so we’re going totally free content into free with an email, right. That, so this free course that over the next 30 days is going to teach you through case studies and everything else.

Exactly how to launch a product. We’re going to take theory and put it into practice. And because it was, you know, a really valuable article, follow it up with more free value. The team at smashing magazine was totally fine with me ending. The article with that, that picked up 4,000 email subscribers at a time.

Wow. That I had maybe five to 8,000 total on my list. So on percentage growth, it was, you know, crazy high and really what it was is delivering a ton of value upfront and then tailoring that into a perfect pitch for a lot more value. And I think that’s what people do with the best Twitter threads, right.

Where it hooks you in. You’re intrigued by this story. It’s, it’s pulling you in, you learn a lot from it. Like, Oh, I had no idea about this business or this tactic or whatever else. And then, you know, at the end, it’s a very relevant call to action rather than like a generic sign up for my newsletter. It’s the logical, logical continuation of whatever I just taught you.

But now behind an email opt in form Is there anything that you’ve learned on Twitter threads and that kind of thing. Like if someone’s getting started, they’re like, okay, David says Twitter threads work. Let me go write some, what are the, like the, a couple of high level things that you would say of like, do this? Not that.

David: [00:42:42] Yeah. So what I would do is I will, I’ll talk about my style and what works really well. So what you want is Twitter works really well for things that require not so much context. So you want to, if there needs to be context, do you want to. Get to the chase very fast. And there’s a, I always think of Casino Royale.

The movie starts with James Bond doing basically parkour running through Italy on top of these roofs. And it’s crazy for seeing it’s like eight minutes long and it’s Epic. And that’s how you want to think about a Twitter thread. Like you don’t need all this background story. You don’t need any of this, you know, hateful eight.

We’re going to go through the carriage forever. And Tarantino movies take like 90 minutes to get into the action. And. I’m much more of the James Bond style when it comes to Twitter threads, just get to it. And that’s what you want to do. First tweet. You want to say, this is exactly what you’re going to get.

Maybe something surprising. So I wrote a thread a couple of weeks ago about a golfer named Bryce into Shambo. Got I think 1.4 million impressions and. Fun fact about that. I almost didn’t publish it because I thought no one was going to read it, which gives you a really good sense of my ability to predict what’s going to do well.

I’m totally serious. I was like, and then I press send and I was like, this is going to just be a vanity. Post cause I really liked golf. And so I was like, you know, it’s just for me, but it crushed. And so I said, Bryson, which I believe Bryson is the world’s most innovative athlete. And then I said, now I’m going to show you exactly what he’s doing.

And I think that you want to. Just save people a lot of time and give them a lot of this rush of insight in a short amount of time. I think that that is even what good communication is that you, you have a lot of these little rushes of excitement within a sort of larger narrative that is being constructed.

And I think that the classic example here is comedy. That what comedy does is it goes from beginning of the show to the end of the show with some general themes. Whatever it is, but within it, there’s all these little mini stories that actually begin to weave the mosaic that is being strung together.

And. Any sort of two to three minute section has its own loud laugh. And I think that that’s what you want to do with the thread. So the theme is Bryce into Shambo, but each tweet has its own individual moment of insight, its own interesting idea. And what’s so cool about Twitter is every single idea gets its own replies.

And so there then becomes this conversation of all the individual ideas within what you’re sharing and. That’s why I like Twitter threads. It really forces me to compress what I’m saying and to focus on the essence of interesting-ness.

Nathan: [00:45:41] Yeah, that’s good. I think one of the first things that people miss about Twitter threads is they think of, Oh, this is a way that I can take that I can say something a lot longer.

And so let me just take this thing and say it in five tweets instead of one. And what you’re touching on is no, no, no. Each one, if at all possible. Like there’s rare exceptions, but if at all possible it’s possible is its own complete thought. And it has its own takeaways. It has its own image, you know, whatever else so that like every tweet stand up, stand on its own.

And what that means is right, that just plays into the idea of a headline, like, or a sentence. I forget it. What copywriter said it of, you know, basically every sentence his job is just to get you to read the next sentence. Yes. You know, and. If one of these tweets is just context or it’s just the extension of the previous tweet.

That’s not going to get you to keep reading because your signal to noise ratio of a sudden got skewed in a way that, you know, Twitter is not made for you have to be high signal on every single suite, even when it’s a long thread.

David: [00:46:49] Yeah. You know, and read a passage, one of the things cause the questionnaires, Oh, what do I write?

Went to Porter fret about? And the first assignment in Write of Passage is write an answer to your most frequently asked question. And I think that this is something that people should be thinking about all the time. What is a story that you tell a lot, but really here? What is a question that people ask you all the time?

Like, Nathan, I want to know from you. Out of all the interviews that you’ve done here, what are the things for people who have 50,000 email subscribers, which is where I’m about to get to, how should I get to 300,000? Say that that’s a very commonly asked question. I know that there would be an opportunity for you to write something really good on that.

And what’s interesting about that is you have this experiential knowledge, which is what I always try to go for when I write, because the thing with experiential knowledge is. By definition, it takes experience to gather whereas knowledge that you read or that you can listen to in a podcast. It’s not the same.

So for example, I had a student who was a financial advisor for FedEx pilots. That was his personal monopoly. That’s what he did. And he had experiential knowledge because guess what? He was a FedEx pilot for many years, which allowed him to. Which allows him to build trust with all of these pilots and.

There’s things that he just knows that you couldn’t read online. And I think that when it comes to Twitter threats, when it comes to writing essays that we were talking about earlier, when it comes to writing articles, I think it’s always just worth asking what are, what is the access, what are the keys that you have that others don’t have?

You have the keys to conversations with really interesting creators. You have the keys to see what it’s like to build a software company in the 21st century. You have the keys to have. Use the internet to build like tiny homes in, in, in Idaho and to think really deeply about what it means to build a remote first company.

These are things that you have the experiential keys to and in so far as you’re able to sort of take what sort of abstract in these hazy intuitions and turn them into these really concrete ideas. You can then end up with ideas and storylines that other people don’t have, because these are byproducts of who you are and how you’re already living. Right?

Nathan: [00:49:15] Yeah. Because a lot of sense, the last topic that I want to spend some time on is like monetization. Once you have the attention of an audience, and let’s say you’ve built it to maybe at least 5,000 subscribers and then obviously you’re at 40,000 and then we can go well beyond that too.

There’s a lot of different ways to monetize paid newsletters are incredibly popular. Now courses, you know like video courses or cohort-based courses are, are very popular. I did eBooks, you know, back in the day. what’s your take on it? Why are, I guess, sponsored sponsored newsletters, sponsored content is quite common as well, but what’s your take? Why did you choose what you did?

And then, you know, what do you recommend?

David: [00:50:01] Hmm. So I think that there, I’m just going to talk about the really lucrative ways to monetize, even though there’s a lot which you’ve discussed. I think that the three really lucrative ways are Really high-end consulting where you work for. Corporations. And every single gig is at least $50,000.

That’s where I would ballpark it. And you have multiple six-figure consulting gigs. So you know all about growth and you go work for Uber and you help Uber gain 2,000,000 new users and you are the person who drives that strategy. Number one. Number two is you run a course and that is basically productized consulting.

So what you do is you have a consulting package that you do, and then you say, I say the same things to every single person. Now what I’m going to do is I am going to. Turn that into a product and I’m going to lower the price, but get way more scale. And so in so far as you can do that, now, if you’re teaching fast-growing startups, how to grow even faster, your market just isn’t that big.

So consulting might be. The better strategy. Whereas if you’re teaching people to write, there’s so many people that want to learn to write that actually trying to productize and then get more scale is actually a better strategy. the best strategy of all is what you do, which is building a company that transcends who you are and what you are this founding influencer somebody who has unique knowledge and a personal monopoly in this area of interest.

And then. You write about that and you use that writing to hire people, to attract investors if you want, and then to ultimately build a company that transcends who you are, where you’ve built the systems and you’ve built the structure in place, but ConvertKit is so much bigger than Nathan Barry,

Nathan: [00:52:05] right? Yeah. And then, I mean, that’s where you get into brand and everything else. which can be a big factor in, in newsletters. I don’t know how much we want to get into it now. Right. But like Sam Parr with the hustle or the guys behind, you know, morning brew or any of those love those, they, they built something that is bigger than they are because they named it.

Right. whereas like, I don’t know, the Nathan Barry show, right. It’s kind of hard to swap out Nathan Barry in that, but if you, but at ConvertKit right being its own brand, it’s very easy for me to swap in, you know, Maybe not a new CEO, I guess I could. but even right, there’s a team of 60 people building that company. Now

I’d like to, I think, diving into a few of these other, other channels, right? If we’re trying to earn a living from a newsletter, right. Paid newsletters have become very, very popular lately. I’d love to hear your take on that. Like why do you have you know, why do you have a, a course rather than say a paid newsletter?

David: [00:53:11] Yeah. So I think that this is kind of a hot take, but I actually think that paid newsletters we’re way over-indexed on paid newsletters. So the, the thing is, I’m not saying that paid newsletters are a bad business, and I’m not saying that the world is bad for paid newsletters. I’m a huge fan of paid newsletters.

What I do think is. is An issue is there’s not a lot of people who are really serious about the opportunity costs of the upside of building a product versus the median range of building a paid newsletter. And I mostly don’t believe in subscription fatigue. And I think that the number of people willing to sign up for a paid newsletter, we’ve only scratched the surface there and for a certain kind of person who loves to write it is a brilliant job.

It is great. I’m not saying Ben Thompson should stop writing Stratechery and should go start a company that is not what I’m saying at all. I’m just saying if you are at some margin where you’re 50–50 on paid newsletters versus company, I would definitely not. Definitely. I would lean towards starting the company because I think the upside is so big.

And so I think that now relative to each other, paid newsletters is getting more hype than it should be relative to starting a company.

Nathan: [00:54:36] Yeah. I think that makes a lot of sense. And when you think about. Like the median returns, which, I mean, we’re seeing a lot of people getting to $10,000 a month, $20,000 a month off of a paid newsletter, which is incredible to just be able to focus on that, to just write that’s so good, especially for that type of person.

That’s good at showing up producing consistently on a deadline like journalists, you know, that is what you’re so good at. But then on the other hand, like I’m always encouraging people to look at the upside of the potential. Oh, there’s that to get a paid newsletter to a million or 2 million a year. Like that’s really, really tough.

It’s also really tough to get a course to that level, but there’s a ton of examples of people doing that on the course side and a lot fewer on the newsletter side.

David: [00:55:21] Right. And what’s going to happen is that we’re going to have Balaji Srinivasan has this idea of a founding influencer and that’s where things are going to go, where you’re going to be able to have your cake and eat it too, where you’re going to be able to create and make money as a creator.

But you’re going to have the. upside of a company. And that is what we’re trying to figure out as an industry in terms of how to monetize your creativity.

Nathan: [00:55:45] I love it. That’s a great place to wrap up. David, thanks for hanging out with us, taking the time to share all your insights. where should people go to follow your work

David: [00:55:53] twitter @david_perell, last name perell.com.

And the last name is spelled P E R E L L and obviously sign up for the newsletters.

Nathan: [00:56:06] That’s perfect. All right. Thanks for taking the time. We’ll catch you later.

David: [00:56:09] Thanks Nathan.