12 Lessons Generating $20M+ Selling Writing Courses Online

We just crossed $20 million in lifetime revenue. So in 2021, my co founder and I launched Ship 30 for 30, which grew into the Internet's largest cohort based writing program, generating millions of dollars. Then in 2023, we expanded our portfolio of writing businesses by launching Write with AI, which is now the number one paid education newsletter on Substack. Does over $400,000 in annual recurring revenue. And as a vertical, it does over.

A million a year in revenue when.

You include other upsells and digital products. And in 2023, we Ghostwriting Academy, which is now the largest training program for freelance writers to reposition themselves as premium ghostwriters. We've had over 2,000 writers go through this program. We have a team of 30 full time team members who help us run it. And this program alone currently does around.

5 million a year in revenue.

And now our newest initiative going into 2026 is launching our digital writing school, which is a community and education program centered around writing online, building an email list and launching digital products. The three most important skills that you need to build in the digital age. So to celebr crossing the 20 million.

In lifetime revenue mark, I thought it.

Would be helpful to share some of my biggest takeaways. Building a portfolio of writing businesses to.

Millions of dollars in revenue, thousands of.

Customers, and building a company that employs over 30 full time team members.

All right, lesson number one is the operational complexity is the moat. So something I really learned this year is the amount of, the amount of things that we have to do to run businesses and verticals and campaigns and webinars and promotions and product launches like it's, it is so complex now. And I, the other day I was thinking back to when we first started Ship 30 back in like 2021, 2022, that business was so simple relative to what we have now. You know, it was just a cohort based writing program. You'd send emails, you would say cohorts starting next week, who wants to join? And then yeah, there was like a little bit of complexity. We had to, you know, start investing in a CRM. We would use airtable. We had to track customer purchases, like really basic stuff, but it was a pretty simple business. Now you know, if we want to run a webinar or a paid challenge, for example, and we want thousands of people to show up to that thing. I mean, you're talking complexity with measuring paid ads. You're talking like cross referencing customers in your CRM, making sure, like okay, well did they buy this product in the past? Did they not buy a product. How familiar are they with our ecosystem? So, anyway, all of this has really reinforced for me that the larger a business grows, the more the operational complexity of running that business is the moat. You know, there's a reason why we have, like, no competition. You know, there is no competition for pga, for example, our premium Ghost training academy. And the reason is just because we've grown through these layers of complexity that are very, very hard for just like a solopreneur or an average individual to rebuild for themselves. So it's not to say you can't start, you know, like a similar type of business, but when you're first starting out, it's so much more lean. You know, you don't have that complexity. But as you take on more complexity, that actually becomes not. It's like more than a differentiator. It becomes a defensive moat from other competitors entering the space. So that's been a huge lesson for me this year.

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The second lesson, this is probably the one I've spent a lot of time thinking about, is subjectivity doesn't scale. So when you're first starting out, like I remember early days when we started pga, we had one success coach, and she was really talented, really great. And I trusted her because she also worked on the ship 30 side with us. So I was like, all right, we're starting pga. I trust you. You're going to make sure students are happy. Do your thing. And in the beginning, that's fine. And when you have someone talented, you don't realize it, but you're basically relying on their subjective decision making. You know, you put them in a role and you go, oh, I trust that you'll make good decisions. The problem with that is that subjective decision making doesn't scale. So I'll give you an example. So now PGA has you know a department head and six success coaches. Well, the other day I was digging into our process for say, reviewing student assignments and something that I noticed that was very subjective is when a coach is reviewing an assignment, one coach might respond with a short slack message, another coach might respond with a long slack message, another coach might respond with a voice note, another coach might respond with a loom. You don't realize it, but that in and of itself means that each individual coach is having to make a subjective decision. When I'm reviewing assignments, how should I respond? And that's just the tip of the iceberg. When you start peeling that back, then you go inside of each individual subjective decision, you go, okay, so let's say we standardize. We say everyone needs to send a voice note. Well, you actually need to make that even more objective. How long should the voice note be? Is a 30 second voice note sufficient or does it need to be three minutes? How should voice notes be structured so you really don't realize it in the beginning whenever a business is small and lean. But so much of getting going is relying on this subjective decision making and your intuition. But subjectivity doesn't scale. And so the bigger a business grows and the more you have to systematize things, the game is actually all about removing subjectivity and making every single action in the business as objective as possible. All right, lesson number three is customers don't want more. They want more valuable outcomes faster with less work. So this is one of those. It sounds so simple. Like I bet even just me saying that you're like, yeah, of course people don't want more work. They just want the thing that they want faster and easier. Right. But it's really one of those things that's so simple that it's complicated. It has taken me a really long time as we've built these different writing programs to figure out and get to the heart at what is the real outcome that the person cares about. And everything else. All the other education, all the other learning, it's really, it's nice to have, it's interesting, people appreciate it, but it actually is not the measure for success. And what I continue learning as we build these new info products and education programs is the game is it's less, not more. You know, whenever I add more and more interesting things into a product or a program, it actually ends up confusing people because then they go, well, wait a second, do you want me to go left or do you want me to go right? You're presenting two different opportunities to me now and really the game of building successful education programs is about removing. It's going, no, let's get to the heart of what you actually care about, and let's remove every single tangential step. Let's remove every piece of, oh, that's interesting, but it's not actually important. And how do you. How do you whittle down a curriculum to. If you want this outcome, you have to take these five steps or these eight steps, and I'm going to make each step as simple and actionable as possible for you. So something I noticed with a lot of creators that are in info is they're constantly, like, trying to come up with ways to add more and more and more resources, but really more just ends up making it complicated. You know, the person doesn't want more. They just want to get their goal as fast as possible. All right, lesson number four. This one might be my favorite from the year. So wanting to start something new is almost always a signal you don't know how to improve the thing you already have, which is the real problem. So let me slow down and explain this because this has been a very painful lesson for me to learn. Whenever you're doing something, if you have a business or you have some sort of task inside that business, you will inevitably reach a point where you don't know how to do that thing better. And whenever you don't know how to improve something, your impulse is to start or find something new and different. So a very simple example is like, let's say you start a low ticket, offer a low ticket digital product, sell it for 300 bucks, and you get 50 people to go through it, 100 people to go through it. Well, most people will get to that first little plateau and then go, I think it's maxed out. You know, I think my market is saturated, or I think there aren't enough customers who want this thing. You know, they make up all these reasons, but really they're all rationalizations for the person doesn't know how to improve or further scale that thing. So what do they do? They go, oh, well, I should create a second product, or I should go create an upsell, or I should create a coaching offer, or I should create a mastermind. And what happens is whenever you jump to something new, you actually deprive yourself of the opportunity to figure out how to do the original thing that was already working better. The other thing that happens is at some point, inevitably in the future, once you start another new thing and another new thing, you will, because you continue to learn, you continue to try things, you will inevitably realize how to improve the first thing. Like it'll at some point, click, you'll go to an event, you'll hear something from someone, all of a sudden you'll realize, oh, this thing stopped growing because I needed to deploy more resources toward it. The problem is now you know how to improve the original thing, but you can't because you've already started another new thing or multiple new things. And so now, even though you know the original thing is what would move the needle fastest for you, you can't give it focus because you've already made commitments over here, you've already started something new. You know, now your focus is split. And I've really felt this in our business over the past couple years. Whenever I don't know how to continue growing or scaling something, the impulse is always, oh, well, we should do something new. We should add another product, we should add another service, we should add another program. And then you start this new thing. And then three months later you realize how to make the original thing better. But now your focus is split. So this has been a very painful lesson for me to learn. And I feel like, honestly, the only way to learn it is to keep making that mistake and keep getting frustrated. And then having to live with the frustration is what motivates you to go, okay, I'm not going to do that again next time. I'm not going to do that again. All right, lesson number five. If you're an entrepreneur, by definition, you are living in a constant state of max risk, which means the best thing you can do with your personal money is take minimal risk. This is actually something that a VC friend of mine in LA told me this years ago. We were out for lunch one day and I was just starting to make real money and I was asking him, you know, like, what I should do with it. Like, teach me. You know, this is a VC worth hundreds of millions of dollars. And he was like, Cole, the first thing you really need to internalize is that as an entrepreneur, you live in a constant state of risk. You know, there is nothing riskier that you can do with your money than start and run a business. And as you grow, and I'm feeling this now, you know, we employ over 30 full time people. We spend six figures on ads every single month. You know, you can see the P and L of our business swinging by hundreds of thousands of dollars every month. You just have to get comfortable with that level of risk. And his advice to me back then, which has taken me a long time to really understand, I feel like this year is the first year I really started to get it is when you're running a business, you are already in max risk. You know, your foot is on the gas pedal 100 miles an hour. And so if you're going to take money out of the business, you don't want to then go, well, let me take this money out of the business and then let me go, you know, buy a bunch of options on a risky company in the market, right? Like don't take the money out of the business and then go buy some speculative altcoin that someone on Reddit said is going to 100x. It's like, why would you already be in max risk and then take money out and then double down and then go pick another max risk thing? And so I've really taken that to heart this year. You know, not just in our business, but even personally. You know, I bought a house this past year, I got married, I want to start a family. All of those things make you want to actually take less risk. And so if I've learned anything this past year as so much risk has increased in our business, is that the more risk inside the business, the more you want to de risk your personal life.

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Lesson number six is a little tactical one. Only pay commissions to salespeople as long as they're part of your team or company. Do not pay commissions in perpetuity. So just a little nugget for anyone here who has a sales team or is building a Sales team. A mistake that we made when we originally hired our first couple closers for PGA was we said, you know, if you sell someone on a long term payment plan, for example, if you, if you leave the company as a closer, you still get those commissions. And we ended up having a couple of salespeople churn, but we were still paying them out commissions for like months. And that was one of those, it wasn't a huge deal, but it was one of those things where we wanted to clean that up and go, okay, long term. If we're going to build a sales team, you really want to insulate the, the commissions. And so if, you know, a closer sells someone on a payment plan and then leaves the company, they should forego those future commissions. This is also a really great way of retaining talent, you know, because if a closer builds a large book of business and they have all these outstanding commissions, well, they're not going to want to leave the company if that means all those commissions go away. So just a little small tactical thing for setting up contracts in the sales team. Lesson number seven is if you're an organic business and want to start running paid ads, you should mentally anchor yourself to needing to pay down a million dollars in ignorance debt, because it is a completely different skill. So this past year I can confidently say that we lit on fire $1 million learning how to run paid ads. And you know, I don't even know where we landed.

Like, maybe it ended up being break.

Even, maybe we ended up losing like 100 grand or 200 grand on it. But we spent a million dollars on experiments and most of them failed or most of them broke even at best. And I think when we started, you know, our business is primarily organic based and when we started running paid ads, I thought I was so ignorant. I just thought, oh, you turn on paid ads and then magically things start working and you realize, first of all, no. Second of all, it's a completely different skill. Third of all, it has a completely different risk profile than organic. Organic is easy mode. You just post content and you know, people show up and go through your funnel and then buy something. Oh, that's incredible. The problem is you don't have full control over that lever. You know, you're relying on the algorithm, you're relying on posts going viral. Paid ads are much more predictable, but they're also riskier in the sense that you might spend five grand only to realize that your funnel doesn't work. You might spend ten grand only to realize that this offer isn't the thing that people are interested in. And I have felt our risk profile go up and up and up. Like, two months ago, we did our first paid challenge. So people signed up for a paid challenge and paid a fee to come live. And we spent $150,000 promoting this thing. And it wasn't until after the fact that me and my co founder, Dickie were like, all right, what was the risk there? I mean, yeah, maybe we wouldn't have made our money back on the back end, but imagine if all those people bought tickets and then my Internet went out. Well, then what do you do? You know? And every time you run a different offer with paid, you don't really realize the risks until you're. You're too far in. And that's why whenever people say, like, oh, shouldn't I just run ads? Like, no, you need. You should mentally anchor to the fact that you need to light a lot of money on fire before you figure out how to do paid ads. Well, and so this year, I mean, I don't even know if I can say we figured out paid ads this year, but we definitely paid down a lot of ignorance, debt. Learning lesson number eight. What gets measured gets improved. What gets maintained atrophies. So this is just a truism for business that I continue learning in different ways, but unless you are actively growing something, it doesn't plateau and then just maintain. It dies. And it might die slowly, but everything is either growing or dying. And I think a fallacy that I certainly have had in the past, but I notice a lot of people carry with them into the game of entrepreneurship is they think, oh, once I build this thing up, then I can take my focus off of it, and then I can go do something different. But, oh, once I built that thing, it'll keep running. No, it might keep running, but it's going to start declining. And the rates of decline. We can debate some things decline faster than others, but everything is either growing or dying. It is not maintaining. And the inverse is also true. If you want to grow something, the very first step is asking yourself, well, how are we measuring success? That's why every time we start a new initiative, the very first thing we do is we set up a dashboard for it so everyone just has something to stare at and obsess over. And then second is we set up a dopamine channel, which is like a slack channel that pipes in a zap, where every time a customer purchases something, the zap sends notification to the dopamine channel so that we can see it we can feel it. And you tie a dashboard to a dopamine channel and now you have a feedback loop. You're like, okay, if I deploy effort into this thing, numbers in the dashboard go up, zaps to the dopamine channel go up, and now I can begin improving it. But again, the fallacy is thinking, oh, I build it and then it'll run forever. No, it won't. Things only run as long as you're deploying effort behind them. Then lesson number nine is every new type of marketing initiative or channel is a year learning curve. This has been another really hard one. This year we tried a bunch of different lead acquisition channels. We tried free webinars, we tried paid live webinars, like Paid Challenges. We tried a new low ticket funnel. So selling a low ticket digital product that then upsold into pga, our high ticket group coaching program. Even just those, those are three different marketing channels and initiatives. And again, I think a faulty belief that I have had for so many years is, oh, well, there's this new thing. Once I turn it on, I'm sure it'll work. We had to run 14 free webinars before we really figured out how to make that work as a channel. You know, our first low ticket digital product we launched and it was like, okay, I guess, but it was like 0.1, 0.2 ROAS. It was not profitable at all. It was like losing a lot of money on the front end. And I think where I've had to grow as an entrepreneur is starting new things and realizing that it's most likely not going to work the first time. It's probably not going to work the first 10 times. But that doesn't mean that as a channel or as a marketing initiative, it doesn't work. Just means you have a bunch of ignorance debt to pay down. So this year I've had to get really comfortable with kicking the, kicking the outcome further and further out on the time horizon and just trusting and going, you know, I'm gonna have to do 10 of these webinars or 20 of these webinars before we figure out how this works. And again, that goes back to the first lesson, which is, and that's the moat, you know, if you're willing to go through all of that growth and operational complexity and repetition like most people don't want to do that. So if you do it, that is what separates you from everyone else. Lesson number 10, a quick, quick and dirty one. Anytime anyone says it'll be fast and easy, you should assume it'll be slow. Hard and expensive. I have trained my brain to. I've rewired my brain. Literally whenever someone says, oh, cool, don't worry, it'll be. It'll be fast, it'll be easy. It won't cost that much. I literally translate what they say to me and I go, this will be hard. This will take a long time, and it'll probably cost two to five to ten times more than they think it will. It's just one of those truisms in building businesses is like, anytime someone says it's going to be easy, it is never easy. Ever.

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Lesson 11. When high performers reach a ceiling in their role, you either need to help them create a new role for them to grow into or elevate them into being intrapreneurs. So this is something that we've experienced this past year, which is we have a couple really high agency, high potential, very talented team members. And, you know, we want to give them more, and we don't necessarily have a role for them. And so that forces us to ask the question, okay, so they have a lot of talent, they have a lot of potential. So where do they go from here? And sometimes that means creating a new role for them to step into that has, you know, that leverages their skill sets or, you know, something that we're now experimenting with for the first time with two different team members is really empowering them to be intrapreneurial. You know, they're still inside our portfolio of businesses, but we're essentially seed funding them to build their own verticals. So this will be. It'll be really interesting to see how this plays out. In 2026, we're starting a handful of new verticals led by team members that we're really, you know, elevating into positions of essentially founders of their own verticals inside our portfolio. But, yeah, I'm Just excited to see where it goes. And, you know, that's the challenge when you employ people and you build teams is everyone has their own hopes, dreams, ambitions, goals. And you have to find a way to make sure that each individual person's goals sit inside your broader vision for the company and that, you know, you have a big enough vision for your company that they can see themselves growing within it. So that's definitely from a leadership perspective. That's something I've been thinking about and working on a lot. And lesson number 12, once you cross 3 million a year, one of your best investments you can make in business is video content, because the resonance and leverage is so high. So honestly, I really wish I would have done this sooner. Selfishly too, I wish I could go back and I had video content like summarizing lessons or sharing things from five years ago. I think that would be really great. But, you know, this year we'll. We'll do over 7 million in revenue. And if I could go back and do anything differently, I think once you cross like around that 3 million a year mark, I think video is such a high ROI investment because is such an incredible forcing function for you to figure out how to articulate all the things that you really want to scale. I think of creating content on the Internet as scaling yourself. Second is it acts as pillar content. You know, now we have a whole team, and so we can take YouTube videos like this and give it to the team and they can splice it apart, they can turn into shorts, they could extract threads from it, they could extract individual tweets. You can repurpose the content in so many ways. But the third, and the real reason is that video is just such high resonance. You know, like if we know if someone watches two hours of my YouTube, the likelihood that they want to join one of our programs goes up massively. And there's just something different. I mean, even me as a writer, I can acknowledge there's something very different about seeing someone and hearing them speak versus just reading their work. So I'm really glad that we're making this a priority. 2026 is going to be a big. A big year for video for us. But I wish I could go back, and I wish I would have started sooner.