Complete Guide to Starting a Newsletter (Beginner's Masterclass)

How do you build a paid newsletter? How do you build a six figure paid newsletter? How do you build a multi six figure paid newsletter? Well, I can tell you because I've done it twice. I've built two paid newsletters to multiple six figures in recurring revenue. The first one was category Pirates. This became a top five business paid newsletter on substack in less than a year. And the second is write with AI, our current paid newsletter. And, and in its first 18 months or so hit six figures and multiple six figures and very recently hit about 200 grand a year in recurring revenue. So what we're gonna do is talk about what goes into building a paid newsletter. Specifically, what are the differences between free and paid newsletters? The only two types of newsletters that I've seen that have the ability to go paid and my personal checklist. This is something I've been refining over the past couple years for determining whether a newsletter has that subscription potential because not all topics lend themselves well to that spec specific business model. And then finally we're going to talk about how long you should give your paid newsletter before you decide, you know, does this have future potential or is this a bet that didn't pan out? Should I just cut the cord on it? So the first thing I want to jam on, which is very high level, is the difference between free and paid newsletters. Broadly speaking, a free newsletter, if that is the model that you want to go with you. I want to run a free newsletter. And then how do I monetize that? Well, that means you're either monetizing via ads or, or you're monetizing via digital products. So for example, there's a big vertical, there's a big part of our business where this is the model. So we have free newsletters. On the digital writing side, we newsletter with ads is because that's one of the most popular models out there. It's also very easy to understand. Truthfully, I think the root of that though, the root faulty belief that people have is they for some reason think it's better or easier to to plug someone else's product than it is to build a product of your own. So the same person who goes, I'm afraid to be salesy, I don't want to pitch my list is also the person who goes, and by the way, check out affiliate greens. No, not affiliate greens, it's athletic greens. Why was I thinking it was affiliate greens? Athletic greens, right. So for whatever reason, they think you might as well call it affiliate greens. They think that there's something better or less salesy about plugging other people's products when in reality it's really the same thing. And you should feel even better about.

Plugging your own products.

Right. So that's the first big model. And if you have a free newsletter and you want to start free and then you upgrade to paid, that's sort of Digital Products 101. The next level though, and it's a very different business model, is having a paid newsletter. And it's worth putting into context. Paid newsletters are a newer category. So I remember 2018, I tried starting my first paid newsletter. This was actually right before Substack came out. Substack was really the company that pioneered the paid newsletter category. And I remember I was trying to start a paid newsletter and there really weren't tools for it. I had to duct tape together three, four, five different SaaS tools. It sounds so silly to look back on. You would have thought that there was technology for this a lot earlier. But even in 2018, paid newsletters were not very common. And so it really wasn't until Substack came along and said, you know what, we're going to special in this type of business model. And then as soon as they came out and they were venture backed, raised a ton of money. Then you saw other platforms like ConvertKit Go, oh, we also provide the functionality for paid newsletters. And then that's just sort of the natural progression, you know, as one new category gets explored, then other people pile in and that's just how it works. But paid newsletters as a business model are still pretty new. And whenever there's a new business model that allows for a lot of freedom, you know that there's price discovery, like how much should you charge for your paid newsletter? Well, it's a, it's a new category. So there aren't really any rules. People are figuring it out. But what I've learned now, growing two paid newsletters to multiple six figures in annual recurring revenue, is that it is a very different type of product. It's very, very different than having a free newsletter that nudges people to some sort of course or digital product or program. Think free to paid, right? Versus the newsletter being the product in and of itself. Okay. The way that I like to think about paid newsletters is actually don't think of it like a newsletter. When you think of it like a newsletter, your brain associates it with all of the things that are part of a free newsletter. And actually that's not really true. A paid newsletter is more like an evergreen book. So what I mean by that is imagine you start reading a book on a topic and you love it so much. It's so helpful. It is exactly what you're looking for for this specific area of your life. And then think about that feeling you feel when you finish the book. And the book could have been super comprehensive, but you go, I really wish they would have covered this a little bit more in depth. Or I wish they would have answered this question. Or you know what, after reading it, I have a follow up like, where do I go from here? That is really the need that a patent newsletter solves. It's the ability to write a book, quote, unquote, on a topic forever. And when you can do that on a specific enough topic in a helpful enough and tangible enough way, what the person is really buying is they're buying for the book, the most helpful way of thinking about it. And there's a reason why platforms like Substack have this sort of community element or a comment section. You know, you can respond to the post and you can interact and you can get to know your readers, right? What is the ultimate purpose of that? Well, the purpose is if you were going to write a book that never ended, you would want to write with your readers, right? As they read a chapter, quote, unquote, they would give you feedback, they would give you ideas, they would ask you questions, and then in the next chapter you could answer them. And that's basically all a paid newsletter is. And so understanding these two models, right, free to paid is the newsletter is really an attention asset, a trust building asset that nudges people up to some sort of product, right? Whereas a paid newsletter is the product, the person is paying for the thing. And so because there's those core differences, the way that you go about these two things is very, very different. So when you're thinking about a paid newsletter, I think one of the biggest mistakes that people make is they think if I make my writing paid, people will pay me for it. And that couldn't be farther from the truth. Just because your newsletter is paid doesn't mean people will pay you for it. The stress test is if you can't get people to read your free stuff, chances are they aren't going to pay for the paid stuff. Okay? So you have to understand that as a business model, the moment you say, I'm starting a paid newsletter, it is, you've moved beyond the part of the relationship where you go, you're going to read my writing like it's not it's beyond that now. Now you are in a very clear value exchange. And the problem gets compounded when the paid newsletter business model is a subscription. When someone is paying you per month or. And usually with things like Substack or other paid newsletter platforms, you have a monthly option, you have a yearly option. Well, whether someone buys monthly or yearly, what that really means is they are making the same purchase decision over and over and over again, either every month or every year. And when a customer has to make that purchase decision over and over again, what that means for your writing is you go, I basically have to resell the value of my newsletter every time I write something. So if you're sitting there and you go, well, that sounds really hard. How do I do that? Okay, from what I have learned, I've just written so many pieces like this, hundreds and hundreds and hundreds, where I have gathered so much signal around what readers find valuable. Not just did you enjoy this, but open your wallet. Would you be willing to pay for this? And would you be willing to pay for this over and over and over again? And so there's two types of newsletters that I think have the highest likelihood of being successful as paid newsletters and newsletters that don't fall into one or two of these categories. As always, there are always outliers. But I would say broadly, if you don't fall into one of these two categories, you're going to struggle. And you could even say it differently and say the paid newsletter model probably isn't the best model to monetize what you're trying to write about. The first type of newsletter that has the potential to go paid is what I like to call researched curation. A good example of this would be the paid newsletter trends. But essentially what you're buying is you're buying someone else or a team of people to go research something about a specific topic. They take the time to do that. They develop expertise in doing that. They develop pattern recognition in doing that. They you really like the conclusions they come to. Like, it's one thing to research it, but it's another, like, how do you interpret what you've researched? And so what you're really buying for 10 bucks a month, 20 bucks a month, 50 bucks a month, whatever it is, you're buying all of that effort. So that's the value exchange. The value exchange is, hey, you're gonna go research this topic in depth, you're gonna come to these interesting conclusions, and you're gonna give it to me and you're gonna do that every week or every other week, or every month and I'm going to give you 20 bucks. And that's the value exchange. High level. When you're thinking about paid newsletters, it's actually important as a writer to remind yourself that am I a good writer? Yes or no? That's not really the value exchange. You could be a really terrible writer. But if you, if you deliver on that value exchange, then the quality of the writing actually comes second or third or fourth or fifth or tenth, it doesn't really matter. The thing that matters is are you delivering on it? And one side of the extreme, right, one of these categories that tends to do very well for paid newsletters is when the thing the reader is buying is basically leveraged labor or time and effort, they're like, I'm gonna give you 20 bucks a month and you're gonna go research this thing for me, okay? And then depending on the thing that you're researching, right, and how it's price anchored depends on what you can get away with charging. So it's one thing if you go, I'm gonna go research, I don't know, like agriculture or industrial farming, you know, versus I'm going to go research startup trends and I'm going to help give you business ideas and business models, right? So depending on what you're researching sort of changes who your target reader is and maybe what their threshold is for what they'd be willing to pay. So research, researched curation is one type of paid newsletter. On the other side of the spectrum, the other type of paid newsletter, and this is, uh, the two paid newsletters that I've built have both been in this bucket.

But I've seen a lot of people.

Find success in the researched curation. But the other extreme is what I call original thinking. So in this paid newsletter, what the reader is really buying, what the value exchange is, is they are buying behind the scenes insights and industry expertise at scale essentially. Think about, you get interested in a topic, you want to accelerate your pattern recognition for that topic, you want to accelerate your growth curve, you want to pick the brain of some really smart person, that person probably isn't selling their time, you probably can't get them to hop on a zoom and grab a digital cup of coffee with you, right? And if you could, it might be really, really expensive. So a way that that type of creator can get around that problem and a way that that type of consumer can get access to that person's brain is by having an original thinking paid newsletter, which essentially means these are all the things that I would tell you if we were in person. I'm just going to give you access to all of the things I've learned behind a paywall. And again, depending on what you price anchor to and depending on how you help that target reader solve a problem, unlock a specific outcome, whatever it is, then that is what affects how much you can charge. And I have found if you aren't in one of these two categories, researched curation or original thinking, it's very hard for a paid newsletter to work. And what happens, unfortunately, is most people who start paid newsletter letters don't do either of these. They do this weird middle ground where they go, subscribe to my writing. Okay, nobody cares about your writing. Nobody cares about my writing. The only reason that people pay for my writing is because I make it very clear, this is what you want, this is what you value. I will deliver on that value exchange. And in return, here's how much it costs. But when you walk up to the market and you go, I'm special, I believe that I'm a talented writer. I took all this time to write this thing and other people deserve to give me their time, energy, attention and money, of course it's not going to work. And yet that's where everyone starts. Because I think blame everything on the traditional education system, but we all sort of grow up in this world thinking that we are what's special, that we are what's important, you know, and the whole idea of building a personal brand compounds this. Where people are like, oh, people want to follow me? No, nobody wants to follow you. What they want to follow and what they, what they want more of is content within a specific topic, helping, helping them solve a specific problem, helping them unlock a specific outcome. So it has very little to do with you and how much you love your own writing. And it has everything to do with who you are helping and how you can help them in their life, solve problems, unlock outcomes, whatever it is. Now, of course, whenever I explain this, there are always outliers, there's always the random person, for whatever reason, they have just this really unique writing voice and they defy all these rules and people find them super entertaining or thought provoking or whatever and like they break the framework, but that person is successful. And I think it's really important whenever you're studying something, I don't just say this for what we're talking about here. I mean, whatever you want to get interested in in life, it's really important to.

Sure.

Motivation, inspiration, find what lessons you can extract from the outliers. But remind yourself that it's not a great strategy to look at someone who won the lottery and ask for financial advice. Right? So outliers are usually not great examples of, well, you know, show me the pattern. What's something that I can replicate? There's a reason why, you know, I take the time to share a lot of these learnings and a lot of these things that I've experienced because a, I don't think I'm an outlier. But baby, I've monetized my writing in so many different ways at this point that I know it wasn't a lottery outcome. Two different paid newsletters to six figures, multiple online course programs to multiple millions of dollars in revenue services. I monetized ghostwriting with an agency. I've done SaaS, we have typeshare, I've self published 10 books. I've done multiple six figures publishing books. So I've monetized my writing in just about every way possible. And so I know that it wasn't, you know, just I woke up one morning, I closed my eyes, I took a swing and I hit a home run and wha. Bam. Like that. That isn't what happened. So if you're thinking of starting a paid newsletter, it needs to be in one of those two categories. It needs to be researched curation or it needs to be original thinking. If you are an expert in an industry and you have an extreme information advantage, I would encourage you to do original thinking. If you aren't an expert in an industry or you don't feel like you have a ton of pattern recognition or frameworks to share with people and that you can monetize, I would encourage you to go the research curation route. And you can always go back and forth like it's not one size fits all. But that's generally how I would think about it. Which sort of takes us into what are the criteria that I look for when thinking about this type of business and business model. I'm sure I will start other paid newsletters in the future. I think it's an amazing business when you can get it right. It's very high margin. It is an infinite game. When you find a topic that you really, really enjoy writing about and you understand the value exchange and you can deliver on that value exchange for readers very, very well. This is one of the best business models that you could have as a writer and it's very foundational. I like thinking of a paid newsletter as this mini engine that gives you subscription revenue. It allows you to write with readers and really get to know them. That subscription revenue can sort of fund the next thing that you want to build, maybe on top of it. It's an amazing nucleus to have in the middle of your ecosystem, but it is a little bit harder, and it's definitely harder for the brand new beginner. I've never written anything before on the Internet. I would not encourage you to start with paid newsletter. It is a great business model that is better served a bit later. Much easier to just start for free and evolve from there. But let's say you're sitting there, you've been writing online for six to 12 months, you've clarified a niche, or at least the direction of a niche. You've started building an audience, you've started building trust, you've been writing with people, you've gathered some feedback, you understand what questions people are asking, you've done a lot of that upfront work and you go, I'm thinking about starting a paid newsletter. Okay, well, these are the four criteria that I think about when I'm stress testing myself. You know, would this topic be a good one for the paid newsletter model? So the first one is your paid newsletter has to be infinitely repeatable. What I mean by this, again, think of it like a book that never ends. You want to frame your paid newsletter and you want to pick a topic that is something that you could write about forever. And so if you're doing a researched, curation paid newsletter, you want to think, what is something that I could research and curate forever. Right? I will never run out of things. And I'm going to give you an example of an idea I had for a paid newsletter that didn't meet this criteria. And it took me a while to realize why it wouldn't work. And then the other side is if you have an original thinking newsletter, you want to frame it around a topic where it's an infinite game for yourself. You're like, I'm passionate about this and I will never stop being passionate about it. I want to write about it forever, I want to think about it forever. And even if it's not quote, unquote, forever, right? You can have a paid newsletter for five years and decide you're done with it, but you want that framework. You want to start from a place of what, what is infinitely repeatable. I'll give you a quick example. A couple years ago, I came up with the idea of wanting to do a paid newsletter in the world of self publishing. This was sort of something that I was thinking I might want as a consumer as well, I thought it would be really interesting to have a paid newsletter where you're constantly sharing like what are the cutting edge things that are happening in self publishing? And the model that I was using in my head is I was saying, well, this exists in the world of finance, right? I mean financial paid newsletters were the ones that originally pioneered this category. You know, you go look at a company like Agora. Agora's the largest paid newsletter portfolio in the world. Essentially it's a billion dollar company that's a combination of paid newsletters and digital products and online courses. But its engine is really paid newsletters. And financial paid newsletters have always been, been sort of the core of this category. Because if you're, you know, trying to make money and you want stock tips, that is an infinite topic. You're never going to wake up the next morning and go, I don't want to know what the next hot stock is. And so I was thinking, oh well that works in finance, maybe that'll work in one of my subcategories, you know, maybe that'll work in self publishing. And it wasn't until I started getting into it and exploring the idea that I started to realize that self publishing as a category and as an industry doesn't move that quickly. You know, it's not like Amazon's updating its ebook algorithms every 24 hours. A lot of the things that are changing in that industry happen over six months or 12 months or two years or five years. And as I started to explore it, I realized, eh, this actually isn't as quickly as I would need it to. This isn't an infinitely repeatable topic. I think it's something I could write about every six months. Right. But it's not something like stocks that are changing minute to minute. And so that's the sort of questioning you want to go through is, is this an infinitely repeatable topic? And if it's research curation, how quickly can I deliver on that value exchange for readers? Right. How often can I present new information? Is it something where there's always something new happening? Right. There's a reason like finance, there's always new stocks, politics, there's always some new law or drama or conflict or. Right? The reason that those industries tend to work well for research curation, because there is always something new happening basically every minute. And so that's one of the components that you're looking for on the original thinking side. You also want to pick a topic that you would feel comfortable and you would be excited to write about infinitely because you don't want to go, I'm going to start writing about this thing and you go, I have three things to say about that and then I'm done. Well, that isn't infinitely repeatable. You're going to run out of things to say. Right? So that's criteria number one. Criteria number two is that again, there are outliers that prove this wrong. But I would say as a rule, it's a very, very help helpful place to start. Your thinking is your paid newsletter has to provide readers with something tangible and not intangible. So one of the mistakes that holds a lot of paid newsletters back is people go, you can read about X topic, they're sort of just promising like the writing generally. But if you look at the most successful paid newsletters, almost all of them in some way promise some sort of tangible benefit or tangible asset. So what I mean by that is in the world of financial newsletters, for example, you will see it's very common for people to go, and in every newsletter we give you a new report. Well, what is a report? A report is a tangible asset. It is essentially an object in the digital world, right? Or something that we used when this clicked for me, this is why I was so excited to start our write with AI paid newsletter is we say in every issue, we explain a framework and then we give you an AI prompt. What is a prompt? A prompt is a tangible asset. You can feel the prompt, you can hold the prompt, you can copy, paste the prompt into ChatGPT or Claude. We did this again with Typeshare. What's the value exchange of Typeshare? Well, when you subscribe, typeshare is basically SaaS is really just an advanced version of a paid newsletter. Side note, but what we do with Typeshare, the value exchange is we will give you templates. What are templates? Templates are tangible objects in the digital world, right? Or you see this with really well researched paid newsletters. Every issue we will give you an in depth case study, right? What is a case study? Is a tangible asset. So as often as possible, I think one of the most important criteria is how do you make your newsletter tangible? Because as a general rule of thumb, in the digital world and especially in the world of info and education, we like to refer to it as digital air. And so when someone is buying digital air, the whole game is how do you make the air feel as tangible as possible possible? How do you, how do you make the air feel like an object or Said, most specifically, how do you make digital air feel like an analog object? And the way that you do that is you find a way where in each issue you are associating the writing with some sort of tangible object template. Case study, prompt, report, what blueprint like something that feels tangible. Third criteria is, as much as possible, you want your paid newsletter to have an objective outcome versus a subjective outcome. So this is a copywriting technique that I've really been clarifying and letting crystallize over the past year, which is most people speak in subjective outcomes. A subjective outcome is. If you say something like, like, this paid newsletter will help you master productivity. Well, if you ask 10 different people, hey, what is your interpretation of the phrase master productivity? What would that mean to you? You will get 10 different answers. And the reason you get 10 different answers is because it is a subjective outcome. There's nothing specific and objective about it. And what happens is when you speak in subjective outcomes, you are essentially killing word of mouth because you are adding subjectivity to the conversation. You are leaving room for interpretation. And when you leave room for interpretation, each individual person has to come to their own conclusion of what that means. And when each individual person has to come to their own conclusion of what that means, each person will come to a different conclusion. And when each person comes to a different conclusion, guess what? They are all going to talk about your paid newsletter in a different way. And when everyone talks about it in a different way, that is the opposite of word of mouth.

So you have to really follow that.

Logic line all the way down. The key is when you can find a way to speak in objective outcomes. So a very easy one using this example would be instead of saying, I will help you master productivity, it would say, I give you the, you know, tools, systems and automations so that you can go from project manager to VP of operations. Okay, That's a very objective outcome. And it's objective because you either got promoted to VP of operations or you didn't. And so when you speak in an objective out, when you speak in objective outcomes, you ask 10 different people, hey, what's your interpretation of that? They will all mirror that back to you. And when 10 people all mirror the same message back to you, guess what? Now word of mouth can accelerate, because now you have everyone saying the same thing. And so I would say, by far, this sort of thinking is the hardest component for people. If you're sitting there and you go, that sounds really hard. Well, first of all, I always like to preface. Okay, so did you expect that having a 99% margin business that allowed you to work from your sweatpants from anywhere in the world and have people see you as an authority would just, just be easy, right? Like, everyone wants these unbelievable outcomes, and then the moment they're confronted with even a little bit of friction, they're like, I don't get it. I thought this was. I just smashed my keyboard and money rains from the sky, right? So yes, your brain should hurt a little. And yes, you should sit there and go, I don't know if I quite get it yet. But let me, let me keep pushing, Let me keep pushing, because now that I understand how to do this, I will continue building successful paid newsletters and I will continue building successful products because I know objective outcomes are more beneficial than subjective outcomes, just like speaking in tangibles is more valuable than speaking in intangibles. So you have to look at this through a lens of skill building, not as, hey, Cole, can you just give me the answer and then I'm done. And then the fourth, this is another one that takes some time to sit with. The fourth criteria is that your paid newsletter has to be price anchored to some sort of upside. It has to be price anchored to either you have an existing problem, I will help you solve that problem. When I help you solve that problem, you will save X amount of money or stop losing X amount of money. Or it could be something that's more tangential. Like, it could be tied to happiness, fulfillment, things that are intangible. But you have to find a way to make those intangibles feel tangible, right? So it's not just like, I will help you feel less unfulfilled. It's like, hey, when you're unfulfilled, that leads to XYZ, which causes 1, 2, 3, and all of that we could napkin math into is probably costing you amount of money per year, right? So you have to find a way to price anchor to either the downside or ideally, the upside when you acquire these skills. That is what separates someone here from someone over there. Once you acquire these skills, earning potential can go up. People who have these skills tend to make 2x more than the person who doesn't have this type of skill. And so if you don't price anchor your paid newsletter, what happens is you essentially fall into the trap of going, hey, read my writing for 20 bucks a month. And that's not what the reader is interested in. The reader is not interested in paying you $20 a month to read your writing. The reader is selfish. The reader cares about Themselves. The reader wants to know how you can help them. And the reader wants to know what is the value of them being helped. How much better would their life be? And whenever I explain this, the objection that sort of pops up from people is they go, well, I don't know. I don't know the exact answer. I don't know exactly how much money they make. I don't know how much more money they would make. I'm afraid of making a promise that that maybe isn't real. That's fine. All of these are guesses anyway. But you can napkin math it. You know, like, I remember we had a situation like this. I was doing a live workshop maybe a year ago, and the example still sticks in my mind. But someone was asking, I write about doing at home yoga routines. I don't really understand how to price anchor doing at home yoga routines. And they were so in the space of, you know, yoga is about being happier and being more flexible and enjoying your life and being more present. Like all of these things are so intangible, I don't understand how to price anchor it. And I go, okay, well, let's go inside the mind of a potential customer. I am a potential customer. I sit all day. I have low back problems because I sit all day. I enjoy going to yoga. All of these things are true. This is actually me. I enjoy going to yoga. The problem is I really struggle to get there. And so what happens is, you know, I can't tell you for how many months I've paid for a yoga membership 10 minutes away. And I keep telling myself that I'm going to get there, but I'm just so busy with work and I really struggle to make it happen. I'm lucky if I get there on a Saturday. That's about it. But I know that yoga would help me a lot and it would probably help my lower back issues and it would probably make me happier. How do you price anchor to someone like that? Well, it's actually very easy. Napkin math. If you were talking to me, you would go, hey, Cole, you're a busy entrepreneur. You probably sit at your desk all day, right? You might even have some low back and hip problems as a result of it. And you might have been paying for a yoga membership for the past year. And you feel guilty because you're not using it and you really wish you could go, but you just can't get there for maybe more than once or twice a month. And so if you think about it, the cost of your yoga membership, you know, say it's 100 bucks a month and you barely get there one or two times a month. That means each time you go to yoga costs you 50 bucks. Or if you want, my paid newsletter is only $10 a month. That's a tenth of the price of your yoga membership. But I will give you routines that you can do at home.

And not only will I give you.

Routines that you can do at home, but I actually understand that you're a really busy entrepreneur. And so the routines that I specialize in are really quick, bite sized 15 minute yoga routines. And actually one of the things I recommend is using your desk chair to do some of these stabilization exercises. So that way when you go back to sitting all day day, your low back won't hurt as much. So you can either keep paying 100 bucks a month for the yoga studio that you never go to, or you could pay $10 a month and I'll give you everything you need and then you'll actually get the yoga routines done. Because like I said, they're bite sized. You can get them done in 15 minutes. That is the whole game. And the only reason that I'm able to articulate that is because I have gone through that same script or that same exercise over and over and over again in a hundred days. Different industries. And so anytime someone says, I don't think that my topic can be price anchored just means they haven't built the skill yet. It does not mean this doesn't work for your industry. It does not mean, oh, people in your niche don't want that or they'll be turned off by that. No they won't. No they won't. You might not even be interested in yoga. And just listening to me articulate it, you're probably like, oh, that makes a lot of sense. I probably need that too. So all of these are faulty beliefs. When I'm thinking about what sort of paid newsletter to build, these are the different criteria that I'm looking for. Let's just recap them one more time. Paid newsletter has to be infinite, infinitely repeatable. Paid newsletter has to be tangible versus intangible. You want to find ways to promise tangible assets in the digital world. Your paid newsletter has to be objective in terms of the outcomes that it helps people unlock. The more subjective the outcomes, the worse it's going to perform, I'm telling you right now. And then number four, your paid newsletter has to be price anchored to some sort of upside or helping the person mitigate some sort of downside. If your paid newsletter can't Check all four of those boxes. There's a very high likelihood that, that you are falling into the trap of I just want people to read my writing and pay me for it. And I think this is one of the hardest things for newer writers to really wrap their heads around is it's almost like you have to go through this whole unlearning process and then sort of retrain your brain to not start from a place of I wrote it, other people should care about it. You have to do the inverse. You should go, what do people care about? I'm gonna go write that. And that. I mean, if I look back on my own writing career, I think that was, was the thing that took me the longest to learn. Okay, quick thing. How long should you give your paid newsletter? General rule of thumb, I would give it about six months. I think in six months you will get a good signal as to whether or not there's real potential here. Category pirates was trending toward six figures in the first six months. It wasn't quite there yet, but you could see, oh, we give this a little more time and it's going to get there. Right? With AI was the exact same thing. Within six months. We hadn't hit hit six figures yet, but the trend line was, yep, if we just keep going, it's going to get there. Inversely, if you spend six months and your paid newsletter is only doing like a couple hundred bucks a month, it's one of two problems. Either you don't have a traffic engine, so you've started a paid newsletter prematurely, you're not writing on social platforms, you don't have a way of bringing people from free to paid, or you haven't checked off the criteria that we talked about here. And I see it all the time. I see people who have amazing traffic engines and then they start, start a paid newsletter and it just doesn't take. And it is almost always because some part of those four criteria isn't happening. So I would really, really encourage you, you know, make sure that you're going through and stress testing these different things. Don't give it two weeks and then call it. Don't give it a month and then call it. Don't even give it three months and then call it. I would give it a full six months, be very consistent, treat it like a true business and then come to your conclusion. And by the way, I've done this, I've launched other paid newsletters, gave it six months and then went, eh, you know, this really isn't trending the way I thought it was, let's kill it. That bet isn't panning out, and that's just part of the game. Sometimes they take off, sometimes they don't. But you want to make sure that you're giving it a real shot. Otherwise it's not a great science experiment. Right. If you want to run a clean science experiment, you want to have as many healthy variables as possible. And this is way more advanced. But this, I want to plant the seed and then, you know, maybe it'll bloom for you in a couple years. When I was building category Pirates, we developed a really interesting publishing model. And I am now doing it again. I'm going to replicate it for myself, but I want to share it because I've never seen anyone do it. And I think that more people with paid newsletters would make a lot more money if they did. This category Pirates started as a paid newsletter. That paid newsletter was 20 bucks a month, 200 bucks for the year. And we aimed to do one very, very long form piece. It was five to 8,000 words, very long form, original thinking every week for a while that got to be a lot. So then we moved to an every other week cadence. And we realized that because the pieces were so long and so in depth, like most people couldn't read it in a week anyway, so we could bring down the volume a little bit. And after about six to eight months of doing that, I started to realize that there was so much value in these long form paid newsletters that it was almost like people were missing it because there was so much packed in there. And we would have people read and send us positive comments. And obviously people were getting a lot out of it. But it sort of started to occur to me our archive was getting bigger and bigger and all of these valuable pieces were like buried in the archive. And a lot of times you don't always go back through the archive and decide to read everything, especially if you're a new customer. And after about six to 12 months, I realized that if you strung a lot of those newsletters together, you essentially had a book. And so what we did is we basically had the paid newsletter fund, our self publishing empire. Over time, this became more conscious. In the beginning, we did it accidentally, and then we sort of dialed this in over time. But as we got going, what this looked like is we would pick an overarching topic, we would go, we're going to write about this topic for the next six months, eight months, 12 months, and then at the end, we're going to take all the pieces on that topic, we're going to do a little light editing and we're going to smash it together into a book. And so if you look up Category Pirates books, the first one we did was the Category Design Toolkit. Second one we did was a beginner's guide to category design. And then the third book was Snow Leopard. And all three of those books are essentially a bunch of paid newsletters smashed together with a little bit of editing. Because there were some things that like didn't make sense out of the context of the paid newsletter. So I had to go back and just refine a couple things edited for a book and then put up for sale on Amazon. And what that allowed us to do was monetize the content a second time. So not only did Category Pirates become a multi six figure paid newsletter in and of itself, but then we also double monetized it with print books, with ebooks, and eventually later with audiobooks. And then the self publishing side of the business also grew to multiple six figures. And I see so many writers that have this opportunity right under their nose and they just don't do it. And they don't do it either because of some faulty belief. They think the reader's not going to want it twice, which, which we found was the complete opposite. People who loved our paid newsletter wanted a print copy on their desk, right? So, okay, that belief doesn't exist. Or they just didn't want to go through the work or they, or they misunderstand how easy self publishing is. And just to give you a quick little crash course on that, all you have to do is create a KDP account with your Amazon account and you format. There's a great tool for formatting the ebook called Reedsy R E E D S y dot com. You can load all the text into it, it'll export it as a fil can upload to Kindle and then you get a cover designed. And then if you want to do print, you know, I would go find someone who wants to format it for print. You're looking at upfront cost of maybe a thousand bucks. I mean if you have a successful paid newsletter, that's no problem. Right? That's what I meant at the beginning, where your paid newsletter can fund some of these other problems or some of these other projects. Maybe if you want to make it look super great, like Snow Leopard as a project looks so great that probably cost us all in four or five grand. Okay, so you spend four or five grand, you double monetize your work. Work and you know, Snow Leopard went on to make tens of thousands of dollars as a self published book. Probably more at this point. Probably crossed 100k at this point. I share that as Whether you go the paid newsletter route, whether you go the free newsletter route, whether you're just writing a ton of content online, I would really, really encourage you to explore the self publishing side of things because the, the self publishing aspect is so much easier than people realize. You don't have to buy any inventory up front. Want it's all print on demand. When you put something up on sale for Amazon, when someone buys the art and business of online writing, for example, it doesn't cost me anything. Amazon prints it on demand for you, extracts the printing cost and then gives me the royalty. And that's how easy it is. And a lot of people don't realize that you can do that with all of the content you're creating in your newsletter. And especially if you have a paid newsletter and even more especially if you have an original thinking paid newsletter because you're already taking the time to essentially write a never ending book. So if you're taking the time to write a never ending book, why wouldn't you just do the incremental effort, smash it together into a book and double monetize it. I am a big, big believer in paid newsletters. I think they're a super cool business model. I also think that they are one of the hardest. So whenever I see a beginner say I'm going to jump right in and start a paid newsletter, I discourage them from doing that. I don't think that it's the business model to start with. I think you are way, way better off starting with a free newsletter and then upsell nudging people to like a tier one online course or a cohort based course or even something even simpler like one on one coaching, like just dip your foot in the water of monetizing. But then as time goes on, as you refine frameworks, as you clarify your niche, as you understand your information advantage, there is a place where in your portfolio that's the way I think eventually that's where you want to get to in your portfolio as a digital writer. Having some sort of paid newsletter, having that forcing function to basically write a book and in public having that benefit of subscription revenue that can fund, you know, oh, now I can put a book out that looks like a traditionally published book, but I can do it self published. I can own all of it, right? Having the paid newsletter as the nucleus of your portfolio is Very, very powerful.

How do you market a six figure paid newsletter? What marketing strategies do you use to attract free subs and convert them to paid subs? Well, I can tell you because our paid newsletter, right with AI just crossed $300,000 in annual recurring revenue. And in this video, I'm going to get super tactical and walk you through exactly how we market our paid newsletter, how we get customers, how we upsell them, how we convert, you know, free to paid, and all the different little copywriting things that we do to incentivize people, how you think about offer creation, what you should pay while behind your paid newsletter, things like that. So first, it's important to understand just the model and almost supply chain for a paid newsletter business. The first component is you have to be writing somewhere for free. Doesn't matter where it is. X, LinkedIn, Instagram, Facebook, could be Snapchat for all I care. All you're doing is generating traffic, then you're driving that traffic to some sort of free newsletter. And the purpose of that free newsletter is A, to take all of the people that enjoy reading the short form stuff on social and you show I can give you more. Right? And B, is to get them on an email list because you sort of need them on an email list in order to do some of these things to incentivize them and educate them on why they should upgrade to paid. And usually there's two types of content that people are ultimately buying when it comes to a paid newsletter. You know, what makes them pull out their credit card and decide to become a customer. The first is some sort of exclusive content. So this could be data, research, trends, insider stories, behind the scenes content, things that you wouldn't normally share out in public, or maybe things that require a bit more context, a bit more explanation. They certainly don't lend themselves well to like Twitter short form for example. But usually it's something like that, something exclusive or the other type of content is expert content. So think of this as you're paying to have coffee at scale with someone who has decades of experience or has really unique information or knowledge or insight about a specific industry, a specific problem. You're like, I want to hear it from you, right? So it's almost always either exclusive content or expert content. And usually whenever I start getting into this, you know, the question people ask is, okay, well should my free newsletter be separate from my paid newsletter? You know, and can they be both? Which is better? What platform should I use? Should I use substack? Should I use ConvertKit? Should I use Beehive. So let's break this down real quick. So first of all, our paid newsletter right with AI is on Substack for two reasons. One is that Substack works sort of like a newsletter feed, if you think about it that way, where both of your free issues and your paid issues are organized into one feed. And the primary reason and why you would do this and why Substack does this is because they know, and we know as the creator or the writer, that the reason someone's going to upgrade to paid is they need to first read some of the free stuff. They need to know, is this something that I'd be interested in so it makes sense to curate them into the same field. And then second is Substack. You know, it's not just a tool. It has this growing community element. And so there is a lot of benefit for us in using Substack because we've found that we can then tap into some of that larger distribution. And I really like Substack's ecosystem. It's very clear that they are trying to not just be a tool, but a publishing platform. And so whenever I see stuff like that, I tend to like to deploy effort there and to double down on those types of platforms because I know, you know, for context, Substack raised a ton of money, venture capital, and they're pouring all that money into hoping to build this publishing platform. And so whenever I see a ton of venture money going into a platform, I know you're going to push this really hard. You're trying to incentivize people to use this. I'm probably going to get a nice little traffic arbitrage by tapping into this. And so that's why we chose to build right with AI on Substack. The reality is though, you can do this on Convertkit, you can do this on Beehive. A lot of these platforms have similar features. But I think a cool data point is that almost 20% of our paid subs are coming from Substack's internal recommendation feature engine right now. So that means 20% of the people that are paying us, we didn't drive the traffic to from social media. They are coming from Substack's ecosystem and exploring around. They discovered right with AI and then they chose to subscribe. That's pretty powerful. 20% isn't nothing. And Convertkit and Beehive have sort of similar features. But I think truthfully, that this recommendation engine substacks is the best and it also leads to the highest quality of subscribers so that's why I like it. Now, if you're trying to figure out which platform to use for you, here's a really easy framework to make the decision. So first, if all you want is just a paid newsletter, you're like, I just want to write, I want to paywall.

Some of it.

You should use Substack. It's the easiest to use. It has a very simple feature set. It's very easy to get up and running. It's nothing like super crazy advanced. And that's sort of the benefit of it. If you want to build a digital products business and you want your newsletter to essentially be the engine of that business, I would recommend using ConvertKit. This is what we use for all of our businesses. All of our primary email funnels are built on convertkit. We have funnels for ship 30, we.

Have funnels for PGA.

We have funnels for typeshare. We have funnel. We have separate funnels even for right with AI in some circumstances. But the majority of the business is really us just driving traffic to substack. We have one funnel where we collect emails through a educational email course and.

Then we tell people about right with AI.

So ConvertKit is a really, really great engine for digital product businesses in the sense that you're collecting emails and then you're upselling people on products. You're putting them into FOMO sequences. You can have abandoned cart sequences. And these are more advanced things. So if you're starting in the beginning and you're like, I just want to be able to pay wall some content. You don't need all of this. Just use Substack. But if, and I wouldn't even make this decision day one, I would say as you get going, if you find that you need some of these more advanced features, I would use ConvertKit. Beehive is a little bit of the in between of these two. And in my opinion, Beehive is actually best not really for a paid newsletter, but for a publication. If you notice, a lot of Beehive's features are really centered around building the landing page of your quote unquote paid newsletter. But really it is actually more like a publication. And a great case study here is Milk Road. Milk Road is a crypto paid newsletter, but really it's a crypto publication and it was built on Beehive. But that's a great thing to look at as the type of thing you can build on Beehive. And Beehive has a bunch of these advanced features. I think it's really good if you Enjoy having all of those different levers to push and pull. But if all you want is just a simple paid newsletter, again, I would go with substack. So think of Substack as the really simple option, ConvertKit as the really advanced option, and then Beehive as sort of the in between. All right, next, how often should you be publishing newsletters? So very simple cadence that anyone can follow is if you want to build a paid newsletter business, you should aim to write one free newsletter a week and one paid newsletter a week for two specific reasons. So first is you want to consistently publish free content because that is your marketing engine. That's how you're going to get people introduced to the things that you write about. That's how you're going to get distribution onto your paid newsletter or your just quote unquote newsletter feed. You need to write things for free to bring people in. Then you want to have the second thing go out each week, which is the product itself, Right? It's the actual paid newsletter. So you go, all right, I'm getting you into the ecosystem. Now, here's the thing that I'm promising you. Right here is the paid newsletter. And, and one of the benefits of and why I love the paid newsletter model is that the longer that you write both free issues and paid issues, both of these archives grow and grow and grow. It's a little harder to understand on the free side. But on the paid side, it's very easy. When you start a paid newsletter, say you have one issue or two issues behind the paywall, well, that's sort of valuable. But when someone pays, they are buying the next thing or the next things that you're writing, right? That's really the trade. But the more paid newsletters you write, the bigger your archive gets. That means that the immediate value of your paid newsletter goes up and up and up over time. So each new person who pays you isn't just getting access to the next paid thing that you write, but they're also getting access to all of the things that you've written in the past, which makes the purchasing decision easier and easier. That's why I love paid newsletters as a business model, because they really compound in value over time. Now, whenever I explain this cadence, of course everyone asks, well, could I publish two free newsletters a week? Sure. Could you publish two paid newsletters a week? Sure. Could you publish five paid newsletters a week? Sure. Could you publish a paid newsletter once every other week? Sure. The reality is all of these cadences work. The question that you need to ask, and I like thinking of this in a very simple equation. The question you need to ask is, what is the value that I'm promising? And value equals the quality of information that I am giving the reader divided by the time of consumption. So how long it takes them to get through it. Or said really simply, value equals information divided by time. Okay, and if your paid newsletter, I'll walk you through two different examples. If your paid newsletter is a financial paid newsletter and you are sharing cutting edge stock tips, right? Well, in that scenario, those stock tips or those trades might only be able to get executed in a 24 hour window or a 48 hour window or maybe like a week long window, right? So it makes sense to share more information to the reader on a faster basis, right? Because in that scenario, value equals information divided by time. The information that you're giving them doesn't take very long to consume. You're like, like, this is the stock you should buy. Like, great, thanks. So you could send that every single morning and it wouldn't be overwhelming to the reader, right? On the other end of the spectrum, this is what we ended up doing. The first paid newsletter that I built a different business was Category Pirates. And with Category Pirates, we did the complete opposite. We were not writing short emails, we were writing essentially 10,000 word paid newsletters. We ended up calling them mini books just to set the expectation with readers. We were like, when this hits your inbox, this is not a newsletter, this is a mini book. Because these things are so long and so jam packed with thinking and value and frameworks. And in that scenario, value equals a ton of information, but also requires a lot of time to consume. And so if we were to go, you know what, let's ramp up the volume, let's send one of these a day to readers. Well, they would find that really overwhelming because it's actually too much, right? Which is very different than sending someone one short stock tip every morning. And so what we ended up doing with Category Pirates, we started by doing it on a weekly basis. And we found that even on a weekly basis it was too much. So we ended up getting to a publishing cadence of publishing one of these mini books, AKA paid newsletters every other week. But that made sense because the value equals information divided by the time investment, right?

So when you're trying to figure out.

Well, how much should I write? What should my cadence be? You need to start with that and figure out, well, what is the value that you're promising?

What is the quality of information you're.

Giving the reader and what is the time investment for them? And so the higher quality the information, the lower time investment, the faster the cadence can be. Right? Whereas the higher the time investment, the lower the cadence should be. But either way, it doesn't really matter if it's weekly or bi weekly or two times a week or five times a week or whatever it is. You still want to hit that barbell of some free and some paid, because the free is your marketing engine and the paid is the actual product. Which leads to how do you upsell free readers to paying subscribers? And I'm going to get super tactical here, because if you just do these one or two things, this is what drives 90% of the outcomes. So the first is because the most effective way to bump free subs to your paid list is to just send them snippets of the paid newsletter every.

Time you write it.

And Substack has this really cool feature where you can insert. You can choose where you insert the paywall. And so what we do is with write with AI every single week, we have some sort of free content that goes out. And then when our paid newsletter goes out, we just intentionally put the paywall about 25, 30% of the way through and then send it to the whole list. So all the paying subs get the full paid newsletter. They're on the paid list. That's what they're paying for. But then the free subs are also receiving that. But there's a paywall after that 30% mark. And so they're getting the snippet of the paid thing. And if you just think about it, how do you get more people to buy? Well, you remind them that you have something for sale. And so that model, you know, it's such a simple thing, but. But I find not very many people choose to do it. But all you have to do is just keep reminding your free list, hey, by the way, yeah, you're getting the free thing every week, but we have the paid thing over here. And let me just keep giving you the snippet. So in substack, you just take that paywall, you put it about 30% of the way page of the. All the way down the page, and then you send the paid newsletter to your whole list. Paid people get it, free people get the snippet. Which leads to something even more tactical.

That you can do, though.

And I think that this, like, the first thing is just make that the habit, right? But this is the more advanced, like in the weeds. This is how you start to Optimize. What you want to do is you basically go back through the paid newsletter that you've written and very intentionally drop the paywall wherever there's a cliffhanger. So you're not just putting the paywall arbitrarily 30% of the way down the page. What you're doing, and I'll walk you through an example here, is you essentially begin the paid newsletter by walking the reader through whatever thing you're explaining. And then right as you're about to give them the thing, right as you're like, you go, oh, okay, and here's my framework for doing it, or here's the prompt that we use for doing it, right? Or here's the checklist that we go through. Right as you're about to give them something really tangible, really specific, that's where you put the paywall. Because it's that moment that the reader sits there and goes, oh, I now feel the FOMO feeling, right? Like, you explained a little bit of the idea. And then you're like, and this is how you would go about it. And then let's move into the next stage. And this is the thing that I would use. And then, like, right before it, that's where you put the paywall. And this is a very subtle little copywriting thing where we've seen the data internally on this with Write, with AI, where when we do this intentionally, the conversion rate of those newsletters is always so much higher than when we just arbitrarily throw the paywall somewhere. And so there's sort of an art to writing your paid newsletters, and you'll get better and better at this over time, but there's an art to, you know, entering the paid newsletter. Here's the idea we're going to talk about today. I'm going to give you a little bit in that first 30% so that you're. This feels substantial. There's value here. But then right as I'm about to give you the answer, right as I'm about to give you the tangible thing, I put the paywall. And if you do that every single week and you send that snippet with that cliffhanger paywall to your free list, you're gonna see, like, the better that you get at that, the higher and higher the conversion rate is going to be. So that's. It's a. It's a small thing, but that's one of those easy levers that you can push and pull. Another really tactical thing that you can do. And this is just sort of like baseline best practice is you want to have a couple CTAs that you just copy paste as a template at the end of every one of your newsletters and every one of your paid newsletters. So for example, Our Right with AI newsletter ends with P.S. can you refer this issue to a friend? P.S. can you gift this paid newsletter to a friend? And then one more PS Please comment with ideas you'd like covered in future issues, biggest takeaway from this newsletter, et cetera. And these are really simple things. It's not like any one of these is going to make your paid newsletter, but it's just a great best practice. It's like, why would you not do that every single week? So you just want to bake in little referral, slash engagement tactics into your workflow. And also it's just helpful to remember whenever you're creating content, no matter how good the content is, people aren't going to remember to send it to their friends or remember to comment unless you prompt them them. So it's such a simple thing, but you have to be the one to remind them over and over and over again otherwise they're not gonna, they're not gonna do it. And then the very last thing you know, this is one of those it's so simple, it's complicated is on the front end marketing side, how we drive traffic to write with AI is all we do is once a day I write something short form on x, sometimes on LinkedIn. But really we use X to drive.

A lot of our traffic. I know I'm going to get this question.

It's not because like oh, LinkedIn sucks for driving traffic and is X better? No. Like any platform you can make work, we just tend to prioritize X for.

This because we prioritize LinkedIn for PGA.

I write some sort of short form post about writing with AI and then I link to our paid newsletter or I link to our educational email course where I give away some of my favorite prompts. And then once people are on our list we tell them, hey, by the way, we have a paid newsletter called Write with AI and that's it. Like that is the whole traffic engine. We don't run ads. We don't have some big fancy affiliate marketing army. We don't have influencer partnerships. All we do is just write on social about the same topic in short form and then remind people to hop over to our paid newsletter. And obviously the paid newsletter needs to be high quality enough. It needs to be good enough to warrant someone wanting to pay But a lot of times, and I talked about this in a previous video that I'll link here, is when you're thinking about what makes your paid newsletter, it all comes down to what you're promising the reader. It needs to be tangible, it needs to be objective, it needs to help them solve a problem. And so when you do that, right, that's 90% of the game. The rest of it is really easy. It's like write on social platforms about the same topic, drive the traffic, send add snippets of the paid thing to your free list and remember to paywall right at the cliffhanger so that people feel that little bit of FOMO in every single issue and go, oh, I actually want this. Let me upgrade to paid. And if you do that, that's how you grow a really great, successful paid newsletter. That is everything we've done to build right with AI to 300k a year. So I'm not withholding anything. There's no part of our funnel that I'm not telling you about. There's no secret sauce or this magical button that I'm pressing that you don't know about.

Okay?

It's literally just that flow and we just repeat that flow over and over and over again and right with AI just crossed 300k annual recurring revenue. We've been at it for probably a year and a half. So that's everything. I just wanted to share our entire, you know, marketing system for write with AI. I hope this helps you with your own paid newsletter. And the biggest thing that I can emphasize is don't get caught up with all this shiny object, like all the.

Different things you can do with marketing.

And some big fancy funnel. It's really not about that, that it's just write about the topic that you know a lot about for free on social. Drive that to a newsletter. Remind your free subscribers that you have this paid thing for sale and make the paid thing really tangible and really.

Objective and help them solve problems and.

You will have a successful paid newsletter.

I have built two paid newsletters on substack to multiple six figures in annual recurring revenue.

Category Pirates to 200k per year and.

Write with AI to 300k per year. And after doing this not once but twice, I finally feel like I have the framework for being able to launch new paid newsletters and scale them to six figures over and over again. So if that's what you want to do, here are the six steps to six figures on substack. Step one, Pick a topic attached to a traffic Engine. This is one of those ideas that is so simple but people overcomplicate it. You launch a paid newsletter. How do you get people to find out about your paid newsletter? Well, you have to write about the same topics for free somewhere else else. And if I could summarize a paid newsletter business, that's pretty much it. You write online for free about a topic you tell people. I also write about this topic on my paid newsletter over here. And then you do that every day, multiple times per day for years. So for example, our paid newsletter Write with AI.

How do we get people to find.

Out about Write with AI? Well, my co founder Dickie and I write about writing with AI on X and then tell people. Oh, and by the way, we also write more about this over here and then we send people to our subscription and we've been doing that once a day, every day for almost two years. And again, it's so simple. But people want to believe there's something more. Like Cole, there's something you aren't telling me. No. The boring work is the moat. The secret is consistency. So if you want to build a paid newsletter, you need to attach it to a traffic engine. AKA you need to write about those same topics for free somewhere else and then remind people over and over again. By the way, I also have this paid newsletter where I talk about the the same topics, just more in depth over here. Step number two, make your newsletter tangible. This is probably the hardest one for new writers to wrap their heads around. So if this doesn't click right away, that's fine. I promise one day you're going to be walking through the grocery store looking for bananas and all of a sudden it's going to hit you. As a general rule, readers value tangible ideas more than they value intangible ideas. For example, just notice how differently these two sentences feel in your brain. Sentence number one, I'll explain to you how to build your first paid newsletter. Or sentence two, here's my six step checklist to build a $100,000 plus paid newsletter on substack. It's the same idea, it's the same topic, but the first sentence is intangible. I'll explain. Now, you can't hold me explaining in your hands. There's no weight to it. It doesn't feel like an object. But the second sentence, which is the title of this video for a reason, is tangible. I'm not explaining. I'm giving you a six step checklist, which is the digital equivalent of me handing you a physical object. It's a checklist. You can hold it in your hands, and so as a result, you value it more. Which is probably why you clicked on this video, too. If you want to build a lucrative paid newsletter around a topic, this is the secret. You have to make it tangible. So, for example, what was the original idea for Write with AI? Was it for us to explain how to write with AI? No, because that's intangible. The idea.

And I remember, remember where I was.

When it hit me, because we were flying to Los Cabos for the eight figure boardroom Mastermind, like two years ago.

And the idea was to have a.

Newsletter that gave writers ChatGPT and Claude prompts. Okay, what is a prompt? A prompt is a tangible asset. I'm not explaining things to you. I'm giving you a digital physical object. And that's all we do in every single issue of Write with AI. We explain how to do something and then we make it tangible by automating that idea in the form of a prompt.

Prompt.

And I promise that Decision is probably 90% of the reason why Write with AI has grown so quickly as a paid newsletter. Because it's extremely tangible. When someone pays to subscribe, they aren't just paying to read. They're aware of the trade in their mind. I give you $20 per month and you give me tangible ChatGPT and Claude prompts. Which means if you want your paid newsletter to be successful, you have to find a way to make whatever thing you're writing about tangible. Now, whenever I explain this, people think about it for like three seconds and then their brain starts to hurt and.

They shout back, I don't know how, Cole. It doesn't work for my niche. I don't want to do it. I can't do it.

I need my mom. Mom.

Okay, relax.

Yes. This means you have to use your brain for longer than three seconds. I'm sorry, but learning how to make your ideas tangible is one of the most powerful skills you can build as a writer because it means you can monetize any idea at any time. You can now sell digital air. So. So just to show you how this works, let's take some far out examples. Let's say you want to start a paid newsletter on. And then we'll pick some really obscure ones. Let's say you want to start a paid newsletter on Kindle Unlimited book trends.

A paid newsletter on Russian literature, and.

A paid newsletter on kitchen remodeling.

Okay, these are all great topics.

Now, how do we make them tangible? Well, the question to ask is what object might each reader value? So maybe in our Kindle Unlimited paid newsletter, we can say, in each paid newsletter, I pick a different subcategory on Kindle and I give you a heat map of the most profitable keywords, key phrases, and content angles in that subcategory. Oh, a heat map.

Right.

That's tangible. I can hold a heat map. I can collect heat maps. I can touch and feel and hold the weight of a heat map. Okay. Boom. Our Kindle Unlimited paid newsletter. Just 10x in perceived value.

All right, how about Russian literature?

Well, instead of just saying, I write about the art of Russian literature, which is what most people would do, do. You can make this tangible by saying, in each paid newsletter, I pick a different Russian short story or novel, I analyze it, and then I give you an annotation guide of all the things you should highlight, underline, and circle as you read it so you can recognize all the different storytelling mechanisms being used. Oh, an annotation guide that's tangible.

Right.

And I bet even as I was saying it, as soon as I said the word annotation guide, you could feel it click in your brain, right? That's the tangible thing you're listening for.

You see how this works?

Okay, let's do one more. Kitchen remodeling. Instead of saying, I write about how to remodel your kitchen, you make it tangible by saying, in each paid newsletter, I pick a different kitchen style, explain why it works and which type of house this would work best in, and then give you an itemized purchase list.

So you can recreate the kitchen of.

Your dreams in your own home. Oh, an itemized purchase list. Right. Tangible. So then once you figure out how you can make your paid newsletter tangible, that's what you lead with with weekly Kindle Unlimited heat maps, weekly Russian literature annotation guides, weekly kitchen remodeling purchase lists. And you can see, this is how we execute our Write with AI paid newsletter to a T. Weekly ChatGPT prompts for writers. Step three the one free, one paid strategy. So, quick, crash course on how substack works. There's two things you need to understand. The first is that substack is becoming a platform in and of itself. So it's not just a publishing tool. It's also an ecosystem of readers and writers. So even though I still think, going back to step one, that you need your own separate traffic engine, like writing on X or writing on LinkedIn or Instagram or wherever, you can tap into a lot of readers just by writing consistently on substack so, for example, not just a publishing tool, it's also an ecosystem of readers and writers. So even though I still think, going back to step one, that you need your own separate traffic engine, like writing on X or writing on LinkedIn or Instagram or wherever you can tap for write with AI. In our analytics, we can see that almost 20% of our paid subscribers have come from inside Substack's network. Again, I still think it's worth having an outside traffic source, but I'm very bullish on this trend continuing to accelerate. And I talk a lot about this phenomenon in my book, the Art and Business of Online Writing. But something that I look for whenever I'm writing online is who's backing the company. And if you don't know, Substack is backed by some of the biggest venture capital firms in the world, like Y Combinator and Andreessen Horof, and Substack has raised over $90 million so far. Quick crash course on Silicon Valley startup economics. Just follow the money. If a platform raises $90 million, they are going to spend a ton of those resources trying to get people onto the platform because they need their metrics to go up and to the right to continue raising more and more money, which is the attention arbitrage opportunity. Substack is going to keep pouring millions and millions of dollars into getting more readers onto the platform because that's how they rationalize their valuation. Which is why I am going to keep building our presence here to ride that wave of increased attention. So if you think of Substack as a distribution platform in and of itself, then the next question is, well, how do you get the readers on Substack to find out about your paid newsletter? You write one free newsletter per week, and you write one paid newsletter per week. And you do that consistently, forever, for a couple reasons. The one free, one paid strategy works so well because every time you hit publishers, you're tapping into Substack's Explore algorithm, increasing the chances of the next reader discovering who you are and discovering your paid newsletter.

But the one free, one paid strategy.

Also works well because your free content is what acts as the appetizer to your paid content, which is like the main course. So, for example, when you go to someone's substack, the first thing a new reader does because they can't read the paid content is to look for something free so you can get a sense of what that person writes about. So you can get strategic here and make some of your best content free and then pin it to the top of your substack. So new readers immediately understand the value.

Of what you write about.

For example, when I was building New reader does because they can't read the paid content is to look for something free so you can get a sense of what that person writes about. So you can get strategic here and make some of your best content free and then pin it to the top of your substack so new readers immediately understand the value of what you write about. For example, when I was building category pirates, this is what we did. We wrote this massive in depth newsletter covering all the high level principles of category design. Absolutely one of our most valuable newsletters ever. And then we made it free and pinned it to the top of our substack. Step number four, you send paid snippets to your entire free list. Alright, so now we're starting to get into the weeds of execution here. The one free, one paid strategy is your baseline. If you can't consistently write one free and one paid newsletter on a specific topic, attached to a traffic engine for months, months and ideally years on end, nothing else matters. I can give you all the hacks and tips and strategies and techniques in the world. It's not going to make a difference. You have to be consistent before you can be prolific. But hey, if you're still watching, I'm just going to go ahead and assume that you're being consistent or you plan on being consistent.

Right?

Promise. So the next thing you want to do to keep your paid newsletter base growing is very simple. On substack, your free readers and paid readers are automatically segmented. So if someone subscribes but doesn't buy, they're on your free list. Category pirates. This is what we did. We wrote this massive in depth newsletter covering all the high level principles of category design. Absolutely one of our most valuable newsletters ever. And then we made it free and pinned it to the top of our substack. And if someone subscribes and buys, they're on your paid list. And this is great because every time you hit publish, you can decide, do.

I want this to be read by.

Everyone so both free and paid readers? Do I want this to only go to the free list so you can pitch free subs without pitching people who are already subscribed on the paid list?

Or do you want this to only.

Go to your paid list so you can give your paying subscribers maybe more content? Step number four, you send paid snippets to your entire free list. All right, so enter access to something that you don't want your free list to get to follow up on the one free, one paid strategy when we do this, what we do is we send one free post to everyone. So free list and paid list, but we actually do the same thing with our paid posts using a cool feature inside substack called the paywall preview. So what you can do is you can choose where you insert the paywall in the post, which means you can make maybe the first 20%, 30%, even 50% of the post free to read by anyone. And so what you do is you send the paid post to both your free list and your paid list, which means you're paying subscribers. They get the whole thing. That's why they're paying. But the people on your free list only get to read in that preview section. And this is amazing. It's a great way to soft sell and remind everyone on your free list. Hey, by the way, if you want to keep reading, you upgrade to paid. But this is only the beginning. Here's how you can take this to level 10. Step number five. You put the paywall preview at a cliffhanger. So most writers don't do this and it is causing them to leave so much money on the table. It's one thing to give free readers a preview of each paid post, but it is a hundred times more effective if you can strategically put the paywall somewhere they feel fomo because that's the real intention of a paywall. Right when it's starting to get good.

Or right when you're about to give.

The reader the thing thing. If they get hit with a paywall, the likelihood that they decide, now we're starting to get into the weeds of execution here. The one free.

Eh, you know what?

Screw it. And they just upgrade.

It goes up.

One paid strategy is your baseline. If you can't consistently write one free and one paid newsletter on a specific topic attached to a traffic engine. So you don't want to throw the paywall preview just anywhere in your paid newsletter.

What you want to do is you.

Want to put it right before you give the reader the tangible thing that you're promising them. Because again, the true value of your paid newsletter isn't really the writing. It's the tangible asset that you were prom for months and ideally years on end. Nothing else matters. I can give you all the hacks and tips and strategies and techniques in the missing it's the ChatGPT prompt. It's the Kindle Unlimited Heat map. It's the Russian literature annotation guide, right? So you actually want to give the explanation the free education away for free in the preview and then right as you say. All right, so so here's your Kindle Unlimited heatmap for the week. That's where you drop the preview paywall. And now the free subscriber has to make a choice. They either abandon the newsletter right there.

Right as it was starting to get.

Good, or they upgrade to paid. Step number six Leverage Substack Notes so lastly, Substack recently added this feature called Notes, which is basically Twitter X. But on Substack it's short form posts that you can make that get distributed in their Notes feed. And again, this is just another way to get your writing in front of more readers. So in addition to the one free, one paid strategy, I would also just republish all your short form content on Substack. It's a very easy double dip. So for example, once per day we just take one of my tweets from X and repost it on Substack. And we've been getting a lot of really great traction. Substack also has this cool feature where it will show you how well it's not going to make a difference. You have to be consistent before you can be prolific. But hey, if you're still watching, I'm just going to go ahead and assume that you're being consistent or you plan on being consistent.

Right?

Promise. So the next thing you want to do to keep your paid newsletter base growing is very simple. On Substack, you're free. Much money you've made turning free readers into paying subscribers from your notes. So don't overcomplicate this one. Substack has a growing ecosystem and now it has an algorithm. So republish your short form content content on substack and introduce more people to your writing. That's it. Now, whenever I explain how to write and scale a six figure paid newsletter, I always get a barrage of questions. Free readers and paid readers are automatically segmented. So if someone subscribes but doesn't buy, they're on your free list. So here are some of the most common questions people ask in case you're sitting there wanting clarification on something or you have a faulty belief about how this won't work for your niche. Alina asks a couple really good questions. So one how long should a newsletter be considering the short attention span all around of readers? Number two, would you start charging immediately or give it away for free first? And three, my worst nightmare about newsletters, millions of unopened emails around the World. My inbox is terrifying. I now open one out of every 10 emails. You know, basically, should you be worried about newsletters in general? So, three really good questions here. So first, I wouldn't think in terms of word count count. I would think in terms of giving the reader a tangible asset that is going to help them in some way. If you can accomplish that in 400 words, that might be all the reader needs. Whereas Maybe you need 2000 words in order to really dig into that particular topic. My perspective is word count is a.

Horrible measure of value.

Just focus on giving the reader something that actually helps them. And if someone subscribes and buys, they're on your paid list. And this is great because every time you second question, I would start charging immediately.

Yeah, I would just start with the.

One free, one paid strategy. You're going to learn very quickly whether or not you're giving people things that they would be willing to pay for. And everything that you're trying to learn from free content should be happening on the social side. Anyway, hit publish. You can decide, do I want this to be read by everyone so both free and paid readers?

Do I want this to only go.

To the free list so you can pitch free subs without pitching people who are already subscribed on the paid list list or do you way so you should be learning what things people value by writing on X or writing on LinkedIn. Your newsletter is really just the doubling down. You want this to only go to your paid list so you can give your paying subscribers maybe more content of all of the things that you see working in your traffic engine. And then third, just this question around the newsletter category as a whole. This is everyone's fear and it's really just a faulty belief. It's a faulty belief to think you know, there's a gazillion emails. No one's going to read my email. The people who need your content will read your emails and read everything from you and the people who don't need your content won't. And that's just how the game works. Pedro asks, you have 2,000 subscribers, a 40% open rate and a 5% click through rate. But you want to improve the latter two metrics. So what are the two things you would do? This is a fun question. So just to level set, 40% open rate is pretty good. The vast majority of newsletters fall in the 30% to 50% open rate range range. If you have below 30%, you have a problem, something's going on. Maybe you have deliverability issues. Or you just have a really cold list, you're not keeping up with them frequently enough, you have some sort of other issue if it's below 30%.

If you have an open rate above.

50%, you're crushing it. So I don't think there's very much to worry about here with a 40ish percent open rate. And the lever for increasing the open rate is almost always just improving the subject lines. And how you do that is make them more tangible. Right? Here's the asset you're going to get inside of this email for click through rate. That's not actually all that important of a metric. What matters is the action the person is taking on the back end of that click through rate. So are they buying a product? Are they filling out an application? What are they doing on the back of that click through rate? Because it doesn't really matter how many people enter access to something that you don't want your free list to get to. Follow up on the one free one page strategy when we do this, what we do is we send one free post to everyone. So free list and paid list. But we actually do the same thing with our paid posts using a cool feature inside substack called the Paywall Preview click. What matters is if they click and then take the action that you want them to take. But again if you want to improve the click through rate, same thing, you just make it more tangible. So don't just say click here to find out how to xyz. You know, you make it tangible by promising something like click here to get your paid newsletter checklist list. The more tangible it is, the more the person is going to value it, the more they're so what you can do is you can choose where you insert the paywall in that they're going to click, the more they're going to take an action. Alexander asks how do you combat the diminishing returns experienced by long term subscribers of a paid newsletter? In other words, what strategies do you use to continuously provide fresh post? Which means you can make maybe the first 20%, 30%, even 50% of the post free to read by any and so what you do is you send the paid post to both your free list and your paid list, which means you're paying subscribers. They get the whole thing, that's why they're paying. But the people on your free list only get to read high value content and keep your long term audience engaged. This is a good question, but before I answer it I just want to point out most people who ask this question or ask a version of this question. Don't even have a paid newsletter to begin with. So they're trying to solve a problem.

They don't have you yet.

Write one free and one paid newsletter every week for 18 months and then worry about this. But let's pretend you've already done that. Okay? So if you've nailed the tangible promise of your paid newsletter, you shouldn't have this problem. When you subscribe to write with AI, for example, you don't just want one ChatGPT prompt, you don't want five, you don't want 10. You want new ChatGPT prompts as a writer forever. And you're probably never going to stop wanting ChatGPT prompts. Or if you want to start self publishing books on Amazon and playing the Kindle Unlimited game, you don't want want one subcategory heat map. You don't want five, you don't want 10. You want a thousand of them. And you want to keep getting them for years into the future so that you can keep your finger on the pulse. That's why nailing the tangibility of your paid newsletter is so important. Because it's the asset. It's the infinite collectibility of the asset that people want, not just them reading your writing. All of the newsletters that struggle with churn problems take this approach of come read my writing. And it takes so long to untrain that in your brain. Like people are not subscribing just to read your writing. They want something in exchange and they want something tangible in exchange. And ideally they want something tangible that they can keep getting new versions of over and over in that preview section. And this is amazing. It's a, it's a great way to soft sell and over and over and over and over again into the future. And two questions to wrap things up. Mia asks, can a woman in her 40s with no prior experience still thrive in this field? And Arna asks, what topics could a 16 year old write about in his newsletter? Do I need prior experience in a particular field in order to write about it? So this is a good question to end on and it's actually the same question just asked from two completely different vantage points. So just to level set here in these questions, this is what every single beginner says at every age, in every industry. Everyone in the beginning takes their experiences for granted. Even some of the most accomplished people in the world do this.

This.

So quick story for you. Years ago, when I first moved to Los Angeles, I met this really successful tech entrepreneur and angel investor. He had this massive, like Iron man style house up in the Hollywood Hills and he just sold his company for a gazillion dollars. Anyway, long story short, I went to his house one day and we were just talking and he was telling me all these frameworks he had for building tech startups. And I was just sitting there like, mind blown, because I'd never heard anyone articulate these kinds of ideas before. And so I told him, you know, this is really incredible stuff. I think this would help a lot of other aspiring entrepreneurs. Have you considered writing about these things online? And he looked at me, just genuinely confused in his $6 million house overlooking the entire city of LA. And he goes, why do you think this is valuable? And I realized in that moment, even the most successful people in the world take their knowledge for granted. We all do, because we're so familiar with what we know that we can't actually understand how or why that information would be valuable to someone else. So to answer both of these questions, can you write as a woman in your 40s? Yes. The mere fact that you're a woman in your 40s means you've had a ton of experiences that a lot of the world hasn't. Mind everyone on your free list. Hey, by the way, if you want to keep reading, you upgrade to paid. But this is only the beginning. Here's how you can take this to level 10. Step number five. You put the paywall preview at a cliffhanger. So most writers don't do this and it is causing them to leave so much money on the table. It's one thing to give free readers a pad. And can you write as a 16 year old? Of course you can. You know more than all the 15 year olds and the 14 year olds. Depending on the subject matter, you might even know more than the 19 year olds or the 20 year olds. The point is, we all take the information we have for granted. It's just the writers who make the most money have recognized that and take it upon themselves to bundle it up, organize it, make it tangible and monetize it. Preview of each paid post. But it is a hundred times more effective if you can strategically put the paywall somewhere they feel fomo. Because that's the real intention of a paywall. Right when it's starting to get good.

Or right when you're about to give.

The reader the thing.

If they get hit with a paywall, the likelihood that they decide, eh, you.

Know what, screw it.

And they just upgrade. It goes up so you don't want.

To throw the paywall preview just anywhere in your paid newsletter.

What you want to do is you.

Want to put it right before you give the reader the tangible thing that you're promising them. Because again, again, the true value of your paid newsletter isn't really the writing, it's the tangible asset that you were promising. It's the ChatGPT prompt, it's the Kindle Unlimited Heat Map, it's the Russian Literature annotation guide, right? So you actually want to give the explanation, the free education away for free in the preview. And then right, as you say. All right, so here's your Kindle Unlimited Heat Map for the week. That's where you drop the preview paywall. And now the free subscriber has to make a choice. They either abandoned the newsletter right there.

Right as it was starting to get.

Good, or they upgrade to paid. Step Number six Leverage Substack Notes so lastly, Substack recently added this feature called Notes, which is basically Twitter X, but on substack it's short form posts that you can make that get distributed in their Notes feed. And again, this is just another way to get your writing in front of more readers. So in addition to the one free one paid strategy, I would also just republish all your short form content on Substack. It's a very easy double dip. So for example, once per day we just take one of my tweets from X and repost it on Substack and we've been getting a lot of really great traction. Substack also has this cool feature where it will show you how much money you've made turning free readers into paying subscribers from your notes. So don't overcomplicate this one. Substack has a growing ecosystem and now it has nalgram. So republish your short form content on Substack and introduce more people to your writing. That's it. Now, whenever I explain how to write and scale a six figure paid newsletter, I always get a barrage of questions. So here are some of the most common questions people ask in case you're sitting there wanting clarification on something or you have a faulty belief about how this won't work for your niche? Alina asks a couple really good questions. So 1. How long should a newsletter be be considering the short attention span all around of readers? Number two Would you start charging immediately or get.