How To Build A Successful Free or Paid Newsletter In 2026

The way to think about a free or paid newsletter is that it is a book that never ends. That, that is the way to think about it. So a nice little exercise for everyone here. Drop in the chat, what is a book that you've read in your life? Probably nonfiction. I mean, the same is true for fiction, but like use nonfiction as the example. What is a nonfiction book you've read in your life where you reached the end and you were like, Damn, I wish this would have kept going. I have more questions. I would love to learn more from this person. I want to hear more. What's a book that you wish kept going? So Natalie Almanac of Naval Ravikant. I agree. I love that book. Sushil Atomic Habits. Think and Grow Rich. Yep. The Dawn of Everything. I haven't read that. I'll have to check that out. What else? What's a book you read that you wish didn't end? The Akatar series. I'm not familiar with that one. I'll have to check that out too. The Creative Act. Okay. Hidden Potential. So I think it's worth asking yourself, what is it about these books that you wish didn't stop. So as a follow-up question, whatever book you're thinking of, whatever book you shared in the chat, go one step further and say what, what, what actually is the thing that you wish didn't come to an end? What, what about that book? Like I Will Teach You to Be Rich by Ramit Sethi, the core proposition of that book is here are a bunch of tactical things for how to save money every month. What does the person wish that didn't stop? Well, I wish that he would continue sharing more tactical ways for me to save money every month. Right. So whatever, whatever book and try to push beyond like one word, like act like actually tangibly, what do you wish didn't stop? You wish the author gave you more of what? Drop in the chat. Everybody need a little more coffee today? Feeling like a little slow on the uptick. What's ideas to think about? Push beyond that, Arnie. What types of ideas? More to talk about in the character stories. Okay. Maybe character profiles, maybe character backstories. Wish the author gave walkthroughs with existing ideas shared in the book. Okay, so step-by-step guides, more specificity. Haley, that's the best one I've seen so far. Adding on to Ramit's book, would have loved more on credit card management. Okay, so tactical ways to save money. One of the categories of how to save money is probably managing credit cards. Haley wishes— I wish that I had more on that specific subtopic, more on credit card management. Okay, so Naval, maybe more on starting an information company. Okay. Arnie, there we go. Way better. Things to say when people get offensive. The key to this little exercise is like before you can create something for other people, you should first audit, well, what do you consume yourself? What are the things that you wish didn't end? What are the things that you consume over and over and over again? What are the things that you want more of? And the more aware that you are of what you consume and of what you prefer, the easier it is for you to figure out, well, how do I create something for other people? The idea of a newsletter is a book that never ends is really like the encapsulation of that idea where a newsletter, like, I think one of the biggest things people misunderstand is that a person doesn't subscribe to a newsletter because it's a newsletter. The person actually doesn't care if it's a newsletter. What the person cares about is what is the thing that the newsletter is trying to give to them. It's some sort of idea, it's some sort of asset, it's some sort of answer, it's some sort of solution to a problem. The newsletter is just the vehicle that carries that, right? And so I think from a first principles perspective, a lot of times writers think, okay, I want to start a newsletter. The reader is going to love the fact that I have a newsletter. And it actually doesn't matter that it's a newsletter. The only thing that matters is what are you helping the reader with? What are you giving them more of? Okay, so, Natalie, I was just about to say that. So why has Write with AI been so successful? Okay, Write with AI is the number one paid education newsletter on Substack. Why has Write with AI been so successful? Because it does— because it's fire, that's right. But because it does one very specific thing. Does one very specific thing. If I give you a bunch of really great AI prompts, do you ever want the faucet of AI prompts to turn off? Drop in the chat, yes or no. You're at a faucet, you're getting really great AI prompts. Do you wake up one day and say, I want to turn that faucet off, I don't want the AI prompts anymore? No, of course not. Right. It is a book that never ends. And the book is called AI Prompts Forever. That's the name of the book. Okay. And so the question to ask yourself, whether it's a free newsletter or a paid newsletter, is what is the faucet of thing that the reader never wants to turn off? Okay, I'm gonna give another really interesting example. Anyone here familiar with the, the writer George Saunders? He's a, he's a well-known American literary writer. He's written a bunch of short story anthologies. He teaches at— I hope I'm not getting this wrong— Syracuse, I think. Isn't he a Beatle? No, no. So very talented writer, but a literary writer. And literary writers typically don't make very much money because they're focused on writing literature, which is the smallest category of fiction. And they're also focused on winning awards, and awards don't pay the bills. His Substack is one of the top 10, for a while it was the number 1, most successful paid literary Substack on Substack. And my, based on some napkin math, his newsletter, I am guesstimating, does somewhere in the ballpark of $70,000 to $100,000 a month. A month. For a literary paid newsletter, okay? It is a huge paid newsletter. He has like hundreds of thousands of free subscribers and, you know, average conversion rate, he's probably got a couple thousand paid subscribers. He's crushing it, okay? What most people don't know is the backstory to this. So let me tell everyone a little backstory here because this illustrates the point really well. So for the past 20 years, George has been teaching a class. I believe it's at Syracuse about Russian literature. And in that class, what he does is you sign up as a student, you know, there's— it's a very small, like, MFA program. So there's only like 6 to 12 students in his class. And in this class, he chooses different Russian short stories. The Russians were some of the greatest short story writers of all time. You're talking like, you know, Tolstoy and Chekhov and like just incredible writers. And so he picks these different short stories, and then throughout the semester they talk about them. The students read the short stories, they show up to class, they read the text, and Okay, he's been teaching this class for 20 years. Thanks, Val, for confirming. Yeah, at Syracuse. Okay, so maybe like 5 years ago, he has historically written almost exclusively literary fiction. 5 years ago, he wrote a book called A Swim in a Pond in the Rain. That book is a nonfiction book. The book is the book version of his class. So his class, he goes, you signed up as a student. I am going to select Russian short stories and we're going to talk about them. The nonfiction book is him selecting, I think it's like 5 or 7 really well-known Russian short stories. And the short stories are in the book and the book is structured where you read a part of the short story and then you read George Saunders' commentary on things he's noticing in the text. So it is the book version of his class. Does everyone follow? Drop in the chat. I want to make sure you understand this before I go to step 3. Okay. Everyone understand? Okay. Does anyone want to guess what the value proposition is of his paid newsletter? Based on everything that we've just talked about, what do you think is the value proposition of his paid newsletter? Yeah, it's the book that never ends. But so what kind? What? What? Yes. Like, like, theoretically, yes. But what? Yes. MD. It is his thoughts on Russian short stories. He runs— he's been teaching a class for 20 years. He turns that class into a book. And what is his paid newsletter? It is a swim in a pond in the rain, but it never ends. Every week he picks a short story. Every week he shares his commentary on it. Every week readers read the short story and the commentary and they comment on his paid newsletter. And that is generating him $1 million a year as a literary professor. Does everyone understand what I've just walked through? Okay. It is one of my favorite examples of this idea, which is a newsletter is just a book that never ends. And so if you subscribe to Story Club with George Saunders, the value proposition is essentially, "I loved your book." I love to swim in a pond in the rain. When it was done, what did I want more of? I wanted more short stories, and I wanted more of your commentary on those short stories. What is Story Club? It is the book that never ends. It is every week I give you a short story, and every week I share my thoughts, my commentary on that short story. Okay, now the important nuance to highlight here is that it's not just short story, we talk about writing. It's the fact that short stories are tangible, right? We associate short stories and books as tangible objects. So every week I am getting a mini book or a mini short story. So I feel like I'm getting an object. And then we talk about that object together. Write with AI is the same thing. Exactly, Natalie, you're beating me to the punch. Same wavelength. That's right. Every week, what do you get? You get a tangible prompt. You can save the prompt, you can copy-paste the prompt, you can bookmark the prompt, you can share the prompt. It is a tangible object. These are really the two big ideas to understand with newsletters is it's not about I have a newsletter and it's actually not about I have a newsletter on a topic because a topic is intangible. I can't hold a topic, right? The two big ideas for newsletters is it's a book that never ends and that book is giving me some sort of repeatable faucet of assets. So what is the asset that you never want to stop receiving? I never want to stop receiving Meta ads templates. I never want to stop receiving weekly workout plans. I never want to stop receiving 15-minute yoga routines. That I can do from my desk. I never wanna stop receiving cooking recipes or vegan cooking recipes or gluten-free and vegan cooking recipes. Each one of these things that I'm listing, there's a tangible component to it, right? I can save a recipe. I can bookmark a cheat sheet. I can share, I can collect. These different assets. And that, like, when, when that clicks, you, you, your newsletter is— you're in the 1%. And it's actually not that hard of a thing to accomplish. It's, it's just you have to start your thinking from that place. And what a lot of people do, and the mistake is they lean into, well, I'm going to start a newsletter about a topic. Right? Well, topics are commodities. I can go to Google and get infinite information on any topic I want. I can open ChatGPT or Claude and get infinite information on whatever topic I want. So having a newsletter on a topic is not nearly as powerful as having a newsletter on a topic that provides a faucet of assets. Repeatable assets. It's a book that never ends. Does that make sense? So, Sushil, follow-up question: How do you find ideas to keep it never-ending? So, anything that is tangible, you can repeat infinitely. Like, is there ever a world— if you're a fitness fanatic, is there ever a world where you want to stop receiving cutting-edge, new, science-backed exercises? Of course not. Like, you always want to know what's, what's the new thing, right? If you love cooking, is there ever a world where you want to stop receiving recipes? Of course not. There's all— there's infinite recipes. You always want to know more. If you love literature, you love reading short stories, is there ever a place— is there ever a point in life when you go, I no longer want to receive or read or talk about short stories? Maybe, but probably not. These are all endlessly repeatable, right? And so I think it's actually— it's easier to identify a tangible thing and then begin the exercise of how do I keep getting creative to repeat it infinitely, rather than not having the tangible thing and just going, I'm going to write about a topic. Broadly, you know, like, right, we've been running Write with AI for 3 years now. And I remember after like the first 3 months, we were like, wow, we've shared a lot of prompts. Like, how do we come up with more? And you do, because the world changes and the technology improves and you learn new things. And there's always ways to make things infinitely repeatable. So do these, these two ideas make sense for everyone? Before you start a newsletter, or if you have a newsletter, those are the two big questions. How do I make it a book that never ends? And what is the tangible component that I never want to end? What's the thing that I want to receive in the mail every single month? Has anyone ever subscribed to like a wine club? You subscribe to a wine club and they send you like 2 bottles of wine a month or something in the mail. So a buddy got me a subscription one year for Christmas and it was awesome. It's like every month a surprise showed up at my door and it's like, here's 2 new bottles for you to try. If you love wine, you never want the wine to stop coming to your front door, right? And so you want that same thing to exist in whatever topic you're talking about. So that makes sense. Okay. Because I'm going to build on this idea here for a second. So we all, we all understand that if you want to go down the rabbit hole, you should poke around Story Club. It's such a good example of this. Write with AI follows all the same rules. Okay. Okay. Now here's the really interesting thing about like info and newsletters in general. If you are executing those two rules that we just talked about, it actually doesn't matter, or it could be either free or paid. Those two rules are how you build a really great paid newsletter, but they are also how you build a really great free newsletter. And what's really interesting, and this, this is one of those things that, like, it has a big asterisk next to what I'm about to say. When you are executing those two rules well, it's a book that never ends, and the never-ending component is a tangible, repeatable thing. You could make that a paid newsletter, or you could make that a really great free newsletter. It actually doesn't matter. It's the same thing. And I think what a lot of people think is they think that there's this, like, big difference between free and paid newsletters. There's not. It seems like there's a big difference because typically most people don't follow those two rules. They make these mistakes and then they— it's like no one's subscribing to the free thing, but they don't realize it's the person's not subscribing because they're not getting the two things that we talked about. And then they're like, well, and how am I supposed to make this paid? The way that you build a successful paid newsletter or successful free newsletter is executing those two rules, plain and simple. The core difference is actually not whether or not you follow those two rules. The core difference is the business model. It's how do you make money. A paid newsletter is the product. A free newsletter is a means to the product. So the offer is the same. I still want people to read a book that never ends, right? Like, start writing online. This free newsletter of ours is really just the evergreen, never-ending version of my book, The Art and Business of Online Writing. That's basically what it is. It's a ton of the same ideas, but people have more questions. They have specific questions related to platforms. They have specific questions related to writing different types of assets. It's basically just the never-ending version of my, uh, book, The Art and Business of Online Writing. Okay, the core difference is that With Write with AI, the product is the paid newsletter in and of itself. And with Start Writing Online, the free newsletter is not the product. The free newsletter is the education piece to the product. And so what this means is you sort of have to decide which business model do you want. Do you want to build a subscription type business model, paid newsletter? Or do you want to build a digital product type of business? Free newsletter to low-ticket digital product. That's really it. One is the product. The other is the means to a product. I will tell you, I think that the easier, more lucrative path for the vast majority of people is to start with a free newsletter. It could be on Substack if you want. A free newsletter that sells readers on some sort of highly specific, highly tangible $350 digital product. I think it will teach you more skills. I think it will generate more revenue in the short term. I think it's sort of the, the predecessor to all the other things that you want to build. Like, if you can do that model, you, you can kind of apply those skills to anything else that you want to do. And that's what makes it so great. Paid newsletters are harder, but I'll tell you the reason they're harder is because most people don't do the two rules that we talked about. So if you actually execute on it's a never-ending book and the never-ending component is a tangible asset that people want to receive over and over and over again, you can build a paid newsletter. Those are the prerequisites. The problem is most people aren't able to do that, and they aren't able to do that because either A, they lack the framework, or B, even if they understand the framework, it's like it takes a little bit of practice to think in that direction because that's so not the way that most people think about this. So it really comes down to business model.