How To Build A $200k/Year Paid Newsletter

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 category Pirates was a business that I started and then exited a year ago. Our current paid newsletter is right with AI 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 in this coffee with Cole, what we're going to 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 specific business model. And then finally we're going to talk about how long you should give your paid newsletter before you decide, 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. So 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 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 have free newsletters on the ghostwriting side. And both of those free newsletters funnel people into ship 30 for 30 or our premium ghostwriting academy. And so really you can summarize the model. Very simply. It's you earn a bunch of trust. I mean, you have to get people onto that email list, right? So it's right online. Get people to your free newsletter, keep giving them more, keep proving that you can help them and then keep nudging them and reminding them that you have another way to help them. You have some sort of product, you have a course, you have a program, and that's sort of Digital Products 101. The other way that you can monetize free newsletters, which I am not a fan of, is with sponsorships and with ads. I know plenty of people who do it. I know people who make great money doing it. My personal belief though is if you can acquire the skill of building digital products, why would you plug an affiliate greens, you know, or an affiliate greens affiliate code? Why would you do that when you could plug your own products? And I often find that the reason people fall into the model of having a free 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 that it's better or easier 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 know 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. And 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 specialize 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 an. It's a new category. So there aren't really any rules. People are figuring it out, right? 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. And so 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 to never end. I think that's the most helpful way of thinking about it. And part of that, 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, right? 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 for the sake of what we're talking about today, I'm not going to go down the free to paid rabbit hole. We'll save that for another cup of coffee. Got my nice little iced coffee here today. So today all we're going to talk about is the paid side, what it means to have the newsletter be the product in and of itself. Okay? 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. Okay? Just because your newsletter is paid doesn't mean people will pay you for it. All right? And a stress test, There's a reason why I evangelize all the things that I evangelize. 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. So what that means 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, and again, I've written, I mean, not only have I grown two different newsletters to multiple six figures, but 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 in the sense of not just did you enjoy this, but you know, 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. And as always, there are always outliers, there will always be success stories that prove some of these frameworks wrong. 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. So a good example of this would be like trends, the paid newsletter trends. 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. 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? Right? 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 going to go research this topic in depth, you're going to come to these interesting conclusions, and you're going to give it to me. And you're going to 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. And so high level, when you're thinking about paid newsletters, it's actually important as a writer to remind yourself that thinking about it like, 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. Okay, 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 going to give you 20 bucks a month and you're going to 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, right? So it's one thing if you go, I'm going to 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 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 research curation side. 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 insights, behind the scenes insights and industry expertise at scale, essentially. So 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 cup of coffee, you know, 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 that 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 newsletters 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. Okay? 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, to give me their time, energy, attention and money, of course it's not gonna work. And yet that's where everyone starts. Because I think I 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. And the whole idea of building a personal brand compounds this. Where people are like, oh, people wanna follow me? No, nobody wants to follow you. What they want to follow and what they want more of is content within a specific topic, 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. There's, 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, and 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, find 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? And 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 B, I've monetized my writing in so many different ways at this point that I know it wasn't a lottery outcome. You know, like I two different paid newsletters to six figures, multiple online course programs to multiple millions of dollars in revenue. I've done services, I monetized ghostwriting with an agency. I've done SAS, 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 isn't what happened. And so I can extract these frameworks and better understand like what were the patterns that led to these types of outcomes. And that's my goal here, is I want to share those with you. 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 researched 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. Okay. 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's something that you. It is an infinite game. You know, like 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 a paid newsletter. I think 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. Uh, 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, right? 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. Be a good one for the paid newsletter model? So the first one is your paid newsletter has to be infinitely repeatable. So what I mean by this, and this is where it helps to think categorically when a reader is subscribing to your paid newsletter. Again, think of it like a book that never ends. So 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 I'll talk you through that. 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 is infinitely repeatable. So I'll give you a quick example a couple years ago, I came up with the idea of wanting to do a paid newsletter around in the world of self publishing. I thought it would be really interesting. And this was sort of something that I was thinking I might want as a consumer as well. It'd be really interesting to have a paid newsletter where researched curation, 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 sort of the core of this category. Because if you're trying to make money and you want stock tips, that is an infinite topic. You're never gonna wake up the next morning and go, I don't want to know what the next hot stock is, right? And so I was thinking, oh, well, that works in finance. Maybe that'll work in one of my subcategories. 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, right? 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, and 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 happen? 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? Those. The reason that those industries tend to work well for research curation is 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 say, you know, 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. 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 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 I see that holds a lot of paid newsletters back is people go, you know, 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, 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 right with AI paid newsletter and 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. Right? 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 exchanges, 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, and 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? 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, 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, blueprint, 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. So 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, right? 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 to, 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. And you have to sort of. 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 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 this guy, 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 once you understand these skills. 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, right? 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, Right? 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 find 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 not feel unfulfill or 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, right? And so if you don't price anchor your paid newsletter, what happens is you essentially fall into the, 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 I, 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, they said, I write about like doing at home yoga routines. I don't really understand how to price anchor doing at home yoga routines. And, 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, 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 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, I was doing a lot, 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 a hundred 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, you, your low back won't hurt as much. So you could 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 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, right? So all of these are faulty beliefs. And so 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 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 subject of 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 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, 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 going to go write that. And that. I mean, if I look back on my own writing career, I think that was the thing that took me the longest to learn. Okay, last 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 six figures yet, but the trend line was, yeah, 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 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, 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, 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, it's, 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. The last thing I want to cover, and this is way more advanced, but this, I want to plant the seed and then, you know, maybe it'll bloom for you. 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, I think that more people with paid newsletters would make a lot more money if they did this. So the model that we really pioneered with Category Pirates was 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 so I realized that there was this opportunity where, you know, we would write about these similar topics, you would see these like a through line, like different paid newsletters would fall into different buckets. And after about six to 12 months, 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. And so what that looked like is we would pick these similar topics, you would see these like a through line, like different paid newsletters would fall into different buckets. And after about six to 12 months, 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. And so what that looked like is we would pick 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 in overtime. But as we got going, what this looked like is we would pick an overarching topic. We would 6 months, 8 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 marketing or to 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 category design, and then the third editing, and we're going to smash it together into a book. And so if your book was Snow Leopard and all three of those books are essentially a bunch of paid newsletters smashed together with a little bit of you look up category pirates books. The first one we did 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 was the category Design Toolkit, second one. We did was a beginner's guide to marketing or to category design. And then the third, it's become a multi six figure paid newsletter book was Snow Leopard or 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. And all three of those books are essentially don't do it. And they don't do it either because a bunch of paid newsletters smashed together with a little bit of, of some faulty belief. They think the reader's not going to want it twice. Which we found was the complete opposite. People who loved our paid newsletter wanted editing because there were some things that like didn't make sense. A print copy on their desk. Right. So out of the context of the paid newsletter. So I had to go back and just refine a couple things edited for a book. 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 Readzee R e e D S y dot com. You can load all the text into it, it'll export it as a file that you can upload to Kindle 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 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 in and of itself. But then we also double monetized it with print books, with ebooks and eventually 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 and know Snow Leopard went on to make tens of thousands of dollars as a self published Book, probably 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 more at this point it's probably crossed 100k at this point. So I share that as of some faulty belief, they think the reader's not going to want it twice. 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. Whether you go the paid newsletter route, whether you go the free newsletter route, whether you're just writing a ton of content online. This is probably a topic for another Coffee with Cole. But 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. It costs you. You don't have to buy any inventory up front 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 it's all print on demand. When you put something up for on sale for Amazon. When someone buys the art and business of online writing, for example, and it doesn't cost me anything, Amazon prints it on demand for you, extracts the printing cost and then gives me that all you have to do is create a KDP account, 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 with your Amazon account and you format, there's a great tool for formatting the ebook. Why wouldn't you just do the incremental effort, smash it together into a book and double monetize it. So I hope you enjoyed this episode of Coffee with Cole. 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 called Reedsy R E e d s y.com you can load all the text into it, it'll export it as a file that you can upload to Kindle. 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 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 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 at it for print. You're looking at upfront cost of maybe a thousand bucks. Like just dip your foot in the, 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, I mean if you have a successful paid newsletter, that's no problem, right? 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 in public, write multiple books in public. That's what I meant at the beginning where your paid newsletter can fund some of like having that benefit of subscription revenue that can fund, you know, oh, now I can put a book out that looks like a traditional self or 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. And so there's a reason why we've done it. We've done it with, right with AI. I plan on doing it more. I have a personal paid newsletter now called the Art and Business of Writing. 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. And I'm going to do the same. You're going to watch me do the exact same thing. Six to 12 months from now, you're going to see me publish a book. That book is going to be the culmination of a bunch of things that I wrote as paid newsletters under the Art and Business of Writing. I'm going, I'm doing it. So if you want to see how this works, feel free to just follow along and you know you will, you will watch me practice in public. But I just wanted to share that as a model because I think it's super interesting. So, okay, so you spend four or five grand, let me know. I mean the response from the first one on this was you double monetize your work and you know, Snow Leopard went on to make tens of thousands of dollars as a self published book. Probably was really, really great. I appreciated all the comments. Thank you everyone. Thanks. For those who said the studio didn't sound too bad, I'm getting it all soundproofed next week which will be very, very exciting. I'm excited to get some panels and stuff in here. Um, and also I am, I'm serious if you have any specific questions or there's specific things that you want me to dig into more at this point. It's probably across a hundred K at this point, so I share that as please let me know. Um, when I sit down to record these, the first thing that I do is I pull up the comment section. Whether you go the paid newsletter route, whether you go the free newsletter route, whether you're just writing a ton of content online, this is probably a ton of the most recent one and go what questions that people ask. So if you have any ideas or any topic for another Coffee with Cole. But I would really, really encourage you to explore the self publishing side of things because the, the self publishing ask thing that I could be helpful on. Like I said, this is my way of getting coffee at scale. So the same way if we were going to sit down for coffee and you were going to pick my brain, I really want you to get that benefit here. So leave comments, ask me questions, Happy to share and I'll see you in the next episode. Is so much easier than people realize. It costs you. You don't have to buy any inventory up front. 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. So I hope you enjoyed this episode of Coffee with Cole. 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, 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 in public, write multiple books 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 traditional self or 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. And so there's a reason why we've done it. We've done it with, right with AI. I plan on doing it more. I have a personal paid newsletter now called the Art and Business of Writing. And I'm going to do this. You're going to watch me do the exact same thing. Six to 12 months from now, you're going to see me publish a book. That book is going to be the, the culmination of a bunch of things that I wrote as paid newsletters under the Art and Business of Writing. I'm, I'm going, I'm doing it. So if you want to see how this works, feel free to just follow along and you know, you will, you will watch me practice in, in public. But I just wanted to share that as a model because I think it's super interesting. So let me know. I mean the response from the first one on this was really, really great. I appreciated all the comments. Thank you everyone. Thanks. For those who said the studio didn't sound too bad, I'm getting it all soundproofed next week, which will be very, very exciting. I'm excited to get some panels and stuff in here. And also I am, I'm serious, if you have any specific questions or there's specific things that you want me to dig into, Please let me know when I sit down to record these. The first thing that I do is I pull up the comment section of the most recent one and go what questions that people ask. So if you have any ideas or anything that I could be helpful on. Like I said, this is my way of getting coffee at scale. So the same way if we were going to sit down for coffee and you were going to pick my brain, I really want you to get that benefit here. So leave comments, ask me questions. Happy to share, and I'll see you in the next episode.