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Weekly deep dives into the Art & Business of Digital Writing, Ghostwriting, & Self-Publishing
Earlier this year, we crossed $20 million in lifetime sales as a writing education business. To give you some context. This is the aggregate amount generated from the following verticals. So ship 30 for 30. Premium ghostwriting Academy right with AI and our digital writing school. About a year and a half ago, I wrote a similar reflection piece on ten Lessons learned, selling $10 million worth of digital education products.
But a lot has changed in our business since then. You know, our portfolio of writing education businesses grew from ten full time team members to more than 30 full time team members. Our yearly revenue went from 6 million a year to over 8 million a year, spread across these different verticals. Our operational complexity, especially running our premium Ghost Writing Academy, is 5 or 10 times what it was a year ago, and we transition from being 100% dependent upon organic traffic to adding in paid ads.
So over the past year, we've probably spent upwards of $1 million on paid ads. So I thought it would be helpful to take a breath here at the 20 million lifetime revenue milestone. We're above it now and share some of our biggest learnings. If you run or have an interest in building a digital education business, I hope that this helps you on your own journey, because we've learned a lot of lessons the hard way.
And if you want help scaling your own digital education business, I'd love to work with you inside of our AI writing school. Lesson number one subjectivity doesn't scale. So anytime someone says to me, I want to scale my business, the first thing that I try to identify is what about their business is currently subjective because oftentimes subjectivity hides in plain sight.
So an example would be say you run an agency and you have one account manager who interfaces with clients and they're great. They work hard, clients are happy, and you think it's time to scale. The problem is a lot about that account managers role hasn't yet been defined. It hasn't been made objective. They do what they do intuitively.
So not based on a prescriptive checklist or a set of processes that you've built. And if you don't have these clearly defined processes, then you can't scale this person's role. They also keep clients happy because of bundled traits. They're personable or they're reliable. But these traits are bundled terms, meaning unless you can unbundle them into repeatable actions, you can't actually scale this person's personality.
And then the third is they solve problems based on their own level of personal motivation. So maybe they're really proactive because that's a quality that they value about themselves. But if this person's role is not gamified properly, with clear incentives that reward the right behaviors and disincentivize the wrong behaviors, then you can't actually scale this person's level of motivation, right?
Because it's going to be different with the next person that you hire. So on the surface, a great hire masks a lot of these problems. And it's not until you start unbundling their role and their motivations and their reward system and even their personality, that you begin to realize the level of specificity that you need to achieve in order to successfully scale someone's role within a company.
Subjectivity doesn't scale. Lesson number two if traffic is concentrated, you should scale vertically. And if traffic is decentralized, then you can scale horizontally. So the amount of things you can sell your audience is dependent upon whether the traffic you generate is concentrated or decentralized. So concentrated traffic means one personal brand building one email list, and decentralized traffic means multiple personal brands building multiple different email lists.
For example, in early 2026, we thought that we could scale our business even further horizontally by promoting a few people internally within our company to lead programs of their own. And we thought, okay, more offers equals more money. The problem is, these team members that we elevated didn't have audiences of their own. Traffic wasn't decentralized, it was still concentrated, which meant that their offers were dependent on our audiences, which ended up competing with our own offers.
So we learned the hard way that if traffic is concentrated to a single personal brand or in our case, my personal brand and Dickey's personal brand and one email list, then scaling horizontally doesn't work. You don't actually gain more. All that happens is you present your customers with more choices and it ends up cannibalizing your core business. This is different than what a company like Agora Financial has been able to achieve.
So their education, business and the traffic they generate is not concentrated to one personal brand. Their traffic is decentralized. Each personal brand and each thought leader has their own audience and their own credibility, which can then be monetized with their own stack of offers. So if I was trying to scale horizontally again, what I would like to do is partner with tangentially related creators who have built their own audiences in similar but different niches.
And then I would focus on just helping them with the back end, with operations, with offer construction and with LTV extension. But you can do that because they are decentralized, right? They aren't cannibalizing your personal brand or your core offer. Lesson number three, it takes about 20 live webinars to figure out how to make a webinar ROI positive.
In 2025, we decided that we wanted to try to scale PGA with paid ads and live webinars. The first webinar we ran was really just a forcing function for us to get a rep in the measure for success. Anytime you do something, the first time is quite literally to just do it. So that's all we focused on. The second webinar was a container to fix everything that broke during the first webinar.
So you got to do the second rep to learn and fix all the things that you figured out the first time. And then the third webinar was really the first rep where we knew enough that we could start to iterate and improve. But if I'm being completely honest, it took upwards of 20 weekly webinars to get it right.
So that's almost five straight months of running a weekly webinar. Each webinar was two 2.5 hours. It was the same slides sharing the same stories and the same insights. We were answering the same questions. We were giving the same pitch and still like it took 20 iterations before we felt like we had gotten it to a point where we could rely on it to perform at a certain level.
And I share that, because if you're thinking about scaling with paid ads and or webinars, I want a level set your expectations. Because before we held that first webinar, I thought, oh, great, we'll just do this once or twice and then it'll be on repeat like it'll be done. And that is not what happened. And I feel very stupid for thinking that that was what was going to happen.
We changed the positioning of the webinar a dozen times. I rewrote and rebuilt the slides of the webinar a dozen times. We held so many webinars week after week that I started to lose my voice. So that said, okay, if you're willing to put in the work, I can tell you webinars can perform very, very well. And now we view them as one of the highest ROI vehicles for acquiring new customers into our ecosystem of writing programs.
That's because they're incredibly effective at educating one to many people live all at the same time, but it comes with a lot of work. Lesson number four the more money you make, the more likely you are to spend money on the wrong things. Everyone loves to believe that more money would solve their current problems, but the reality is, the reason you have the problems you have is because you cannot effectively manage your current resources.
So more money doesn't make those problems go away. In fact, it is quite the opposite. More money just increases the likelihood that you will spend money on the wrong things. Some of the worst hires I have ever made were during periods where our business was generating the most revenue and the most profit, and some of the best hires that I've ever made were during periods where our business was very small and very lean, and I was being very conscious and critical of every single person I brought on.
And that's because when someone's monthly salary is a rounding error for the business, you don't scrutinize the decision as much, especially when you're growing and you're growing fast. It's so much easier, especially when you're stressed, to just say, whatever. We'll just hire someone that they'll do it. But when you remove all that excess cash flow and you ask yourself the same question, what?
I hire this person? All of a sudden you realize, no, I would not. And this is why you hear entrepreneurs talk so much about fighting to stay small. No matter how much you grow, you want to try to make level headed hiring decisions as if you were still that small, lean, cash conscious company. The nuance is yes. Oftentimes you have to spend money to make money or invest in talent proactively in order to grow to the next level.
So I'm not advocating for frugality. I am reminding myself in sharing this, to scrutinize the ROI of each person I hire, regardless of whether or not their cost is a rounding error for the business. Every dollar counts. Lesson number five limit sales people's commissions to their current employment. This is a pretty specific lesson that really only applies if you run a high ticket group, coaching program, or agency or B2B business where you have some sort of sales team.
But it was a painful one for us, so figured I'd share. When you hire salespeople, they are typically paid on commission, and if you need to limit their downside, you should do what's called a draw, which is where you protect their downside while letting them keep their upside. So this passes the risk along to the business instead of the individual.
So here's how it works. A typical draw would be like three grand to five grand per month. Think of this as their salary. The sales person gets this draw, so say three grand a month no matter what. So this protects their downside, but they do not unlock their upside until they generate three grand in commissions for themselves. So this makes their draw similar to like in advance.
For high performers, the draw doesn't matter because they're going to recoup and exceed their draw every month anyways. But for low performers, the draw gives them some runway to figure things out. But if 2 or 3 months goes by and they aren't able to outturn their draw, the answer is pretty clear that they aren't a good fit. The reason that you have a draw is primarily for the first 1 to 3 months of onboarding a new sales rep to mitigate their downside while they get trained.
I digress. The lesson is that when you provide salespeople with an employment contract, you want to explicitly state that they only receive commissions as long as they are actively employed by the company. So this prevents a few things. First, it simplifies accounting. You do not want to be continuing to track monthly payouts for people that you no longer even employ.
Second, it prevents salespeople from selling and bailing. Every so often, you'll run into a salesperson who gets a little liberal over promising customers, and then if when they leave, you're stuck paying them out. For a customer who may end up being unhappy, they might ask for a refund 30 days later. I want to say this is rare. Doesn't really happen that often, but when it does happen, it's one of those things where you want to kick yourself.
Third is it acts as a retention mechanism, so selling customers on recurring contracts or payment plans is a bit like a salesperson building up their own book of business and recurring revenue. And eventually what happens is there is no incentive for them to stay if they can just take all that revenue with them. So you want the stickiness of the revenue to be a motivator for them to stick around.
We made this mistake with the first handful of salespeople we hired for PGA, and it cost us tens of thousands of dollars in commissions that we shouldn't have had to pay out, but didn't explicitly name in our employment agreements. Lesson number six you can do more way, way longer than you think. One of my favorite hormone frameworks is more better new.
So first do more. Do as much as you possibly can. Then when you've maxed out effort, do it better and better and better and better. And then and only then, when you're doing as much as you can, as best as you can, should you consider doing something new or different. Unfortunately, I have continued to learn the hard lesson that you can do more way, way longer than you think.
So let me walk you through this very slowly, because this is taking me a long time to understand. Whenever you reach some sort of ceiling or a plateau, it is very easy to believe that you have maxed out your opportunity vehicle. You think there is no way that you can do more, but the truth is, you think that you've plateaued because you haven't yet been exposed to the next level of more.
It's kind of like being a middle school basketball player and thinking there is no way I could work harder. But then one day you go train with the high school kids and you realize, hey, on a second, there is a completely different level of effort that is available to me. So we experienced this. We've experienced it in a lot of different ways, but we experienced this when we joined Alex or Moses workshop.
And you think you're running so many ads until you sit in a room and hear someone explain how they're running literally a hundred times more ads than you. You think you're hiring so many people until you sit in a room and hear someone explain how they're hiring ten times more people, ten times faster than you. You think that you have such high standards until you sit in a room and hear someone explain their standards, then you realize that their standards are way higher than your standards, and you think that you're working so hard until you sit in a room and hear someone explain that their day starts earlier than yours and ends later than yours.
So the point is, anytime you feel like you've reached a more plateau, the answer is not actually to jump to doing something better, or especially not something new. The first answer is to find an environment that challenges your definition of more, because chances are, however, you are defining the max of whatever thing you're doing is wrong. Lesson number seven when you reach a better plateau, the impulse is to pick something new, which is a mistake.
When you have sufficiently maxed out more of something, the next step is to do it better. The problem with better is that it's incremental improvement, so doing something better is usually not some giant action or giant decision or big change. Better is more likely to be a thousand tiny upgrades made one at a time. None of which, by the way, in the moment lead to an exponential outcome.
But all of them added together over a prolonged period of time do so. As Hormuz puts it, it's 1000 golden bees and not one silver bullet, which means better requires a lot of patience and a lot of consistency. Two things that human beings are historically very bad at. As a result, as soon as you begin down the better path, the incremental improvement path, you are quickly confronted by a handful of very painful realities.
This is boring. This is tedious, this is monotonous. This is going to take forever. All of these things are what caused so many people, myself included, to come to this faulty conclusion that they should do something else so they think they should start something new. And that is almost always the mistake. The reason I say it's a mistake, and I continue to learn this lesson myself, is because people stop pursuing the better path for only two reasons.
First, they get bored. They get frustrated, they lose interest, or second, more commonly, they don't know how to do better anymore. When this happens and you decide that the right decision is to start something new, you actually create two different problems for yourself at the same time. So when you pick something new. First you start over. You're solving for boredom with novelty, which feels really good in the short term, but very quickly loops you right back to where you were before.
And second, you deprive yourself of learning the even better way to do what you were doing before. So the higher you climb, the better you get at something, the more nuanced the next improvement is. And sometimes you need to spend 2 or 3 months consuming lots of different thought patterns and different information and different ideas and different perspectives to learn how to do what you're already doing a little bit better.
The problem, though, is once you start something new. Well, now you have a new commitment. So a few months later, when you finally realize how to do the thing that you were doing before, better now, you can't do it. You don't have the time. You don't have the bandwidth because you've already started prioritizing something else, something new. Which is why I have set a new little rule for myself.
Any time I reach a better plateau, I will not start something new unless I have given myself at least three months of trying as hard as possible to expose myself to whatever the next level of better might look like in my current chosen domain. 99% of the time, when you give yourself this space to discover how to raise your own standard, the answer becomes very clear.
And the better you get at something, the more you actually learn how many more levels of better there are above you. Very rarely 1% of the time is the right answer. To give up, start over and choose something completely new and different. Lesson number eight there is no one right way to drive traffic to a business. There are so many different playbooks that work right now to drive traffic.
You could build an entire business off of YouTube organic. You could build an entire business off of just Instagram ads. You could build an entire business using LinkedIn cold outreach. You could build an entire business as a TikTok shop affiliate. You could build an entire business running live webinars. The list of things that you can do is literally endless.
But something that we come back to over and over again inside our own business is committing to play the game and running the playbook that we know works for us because there is no one right answer. And I promise the grass is always greener. It is so easy to see someone else succeeding online. Running a completely different marketing playbook is you and thinking, oh, I should do that.
I bet their model is so much better. I bet they don't have any of the problems I have. And none of that is true. As a mentor used to say to me all the time, you would say, Cole, you're going to have a bag of problems. Either way, you just get to pick the bag. There is no marketing playbook that is devoid of risk.
Volatility or some level of this is really annoying, which means the game isn't to bounce around and try every new playbook of the month. Just commit to a platform, or commit to a style of marketing and use it to build a great business for yourself. You do not have to do everything, just do the one thing that works for you.
Lesson number nine if you don't see traction with the budget version, don't spend the money on the premium version. The marketing channel that has taught me the most about budget allocation has to be YouTube. Everyone loves to believe, myself included, that the secret to YouTube is high production quality and a pro grade at home setup, and a teleprompter and a fancy camera and a scriptwriter and a thumbnail designer.
The reality, though, is none of these things matter if a the content isn't helpful or entertaining, depending on what your niche is, and b you are awkward on camera. So I have now published over 1400 videos on my YouTube channel, and I can tell you that many of my highest performing videos actually have the lowest production quality. For example, little story here.
Earlier this year, we doubled our entire video production team and started investing heavily into YouTube. So we hired a head of video content. We hired a lead editor, we hired a thumbnail designer. We had multiple shorts editors, and once a month we would spend five grand renting a huge Airbnb property here in Arizona to film an entire month's worth of content.
In eight hours, I would just wake up and just rip eight straight hours of videos altogether. Our monthly video production team costs were probably in the ballpark of around $50,000 a month, and the videos looked awesome. Like it was really cool. We captured a lot of epic looking content, until one day I recorded a loom video and published it onto my YouTube channel myself.
And that loom YouTube video outperformed almost every single high production video that we had just filmed, edited, and published over the prior three months. Which suddenly raises the question, what am I spending 50 grand a month for now, obviously, there is an intangible cost to building a brand, and you can make the argument that high production quality content builds a stronger relationship with customers or up levels the perceived value of the brand, blah blah blah.
The point is still the same whenever someone asks me how they can get started on YouTube or which camera they should buy, the first thing I tell them is to not buy anything. You should just record 100 loom videos of you talking over a Google doc or a notion doc. And the reason is because in the beginning you need to build a few skills.
So first you need to do it consistently. You need to prove to yourself that YouTube is a priority. Do you know how many people say, oh, I want to start prioritizing YouTube. And then they make two videos and then they stop. This is a skill that needs to be built. The second is you need to clarify your own thinking for video.
Video is a very different medium, and you can do that with just a Google doc. You don't need fancy cameras to clarify your thinking for a video. And third is you need to practice speaking on camera, which does not require a professional camera. There is literally zero point in increasing your video production costs when you haven't built the most basic skills or seen any traction from your efforts, because if you can't do it with the budget version, trust me, you're still not going to be able to do it with the premium version.
And this is coming from someone who has spent over $100,000 building this home studio. I would still tell myself the same thing. Start with 100 loom videos and this lesson applies to everything. Lesson number ten you can't automate what you can't articulate. The biggest benefit I've gotten from using AI has nothing to do with AI itself. The more I use AI, the more I realize that I am building the skill of prompting, not prompting AI, but prompting action.
Who takes the action is irrelevant. It could be a robot, it could be a human. Prompting is the skill of articulating what it is you want done, how you want it done, and how you define when it has been done successfully. I've been building education products and programs for over six years now, and after teaching tens of thousands of students about how to write in the digital age, I have accumulated a tremendous amount of pattern recognition around which actions lead, to which results, and which actions lead to overthinking or procrastination or lack of progress.
And whenever I think about the AI era we're in and where AI is headed, I always come back to the things that I've observed within our own writing programs. Most people want the shortcut, but the shortcut is always the longer road in disguise. Most people want to believe that there's a secret key on the keyboard that makes everything easy and automatic.
And yes, some things will get easier, but the work isn't going to go away. The work is just going to move somewhere else. Everything takes work. And third, most people call AI slop because they can't define what not slop is in the first place, which has nothing to do with AI, everything to do with their own lack of clarity.
All of these things are starting to create a pattern that I'm noticing over and over again, where the more people try to skip the short term pain of learning how to clearly articulate a thought or an insight, or a story or a task, the more they give up the long term gain of combining that clarity of thinking with AI leverage, because you can't automate what you can't articulate.
Lesson 11 when you find a marketing tactic that works, do as much of it as you can, especially if your business is built on organic marketing. The entire name of the game is finding platform arbitrage opportunities to generate high quality leads. So, for example, back in 2021 2022, Twitter's algorithm prioritized threads. These were long listicles consisting of like 10 or 20 tweets all strung together.
If you saw this trend and you built the skill of writing viral worthy threads, you could generate millions of views and tens of thousands of email subscribers with relatively low effort. I know, because we did. And this is how we built ship 30 for 30 into a multi seven figure writing program. In its first two years. All we did was right daily threads on Twitter and send people at the end to our free email course.
Start writing online. But marketing tactics don't stick around for very long. So by 2023, after Elon bought Twitter and renamed it to X, threads basically went extinct. But I've been writing online since 2007. I have seen dozens of these little marketing cycles where a tactic absolutely crushes for like 12 to 24 months and then completely disappears. So by the time the Twitter algorithm changed, we were already on to the next platform.
In 2023, we started republishing our most proven ideas and content on LinkedIn in the form of carousels. The next viral worthy format and LinkedIn very quickly started outperforming X in terms of lead generation. For us, even though our X audiences were like 3 to 5 times bigger. The point is, whenever you find a marketing tactic that works, do not take it for granted.
Recognize that you have just stumbled upon an arbitrage opportunity, and you should do as much of that marketing mechanism as possible, as fast as possible, because it is not going to last forever. And if you want to know what marketing tactic has been working the best for us and many other creators right now, it's viral drops. So we've been running these on X and LinkedIn and even Substack for the past year, sometimes multiple times a week.
A viral drop is where you package together some sort of asset for your target audience, and then send it to them in exchange for commenting and engaging with the post. The reason this works so well is because it creates a little flywheel, so you can only get the asset if you comment and engage. As more people comment and engage, the algorithm sees that engagement and shows the post to more people.
And as more people see it, more people comment and engage and it just repeats. We have had some viral drops get hundreds of thousands of views, attracting thousands of new email subscribers into our various funnels. And as soon as we started seeing this marketing tactic work, we ramped up the volume as much as possible. We went from doing these like once a month to once a week to multiple times per week.
That said, little context. A lot of people are very hip to this tactic now, and we're already seeing diminishing returns with it about a year later. So when you see a tactic working, you should exploit it, but also keep your eyes out for the next arbitrage opportunity, because the one that you currently have will not last forever. Lesson number 12 the best managers are interpreters and incentivized accordingly.
You enter the Valley of Death as soon as your company crosses about 15 employees. And the reason is because as a solo founder or a pair of co-founders below 15 employees, you can still manage your whole team. But once you cross around 15 team members, it gets to be too much. Which means you need managers. The problem with managers or department heads is they are typically pure costs, so their job is not really revenue critical.
It's more organizational, making sure that the business continues operating at a certain standard and doesn't break. They also tend to be expensive hires because in order to be a manager, you need to have enough working knowledge to manage the people doing the doing right. And all of these costs fall directly to the bottom line. So the business goes through this valley of death period where in order to grow further, say beyond 15 employees, you need department heads.
But the department heads are pure costs, and those pure costs have an immediately negative impact on your business profit in the short term, which means to get back to the same level of profitability or more, you need to grow beyond the capacity that you've just opened up within your business. This is why you hear entrepreneurs talk about how their business at ten team members was more profitable than their business at 30 team members, because as soon as you enter that valley of death, there is no middle ground.
You either expand the capacity of the business and successfully grow through to the other side, or you don't. And if you don't, then it doesn't make sense to have that entire layer of management in the middle. Now, building on this, all of these problems are compounded when your managers are not interpreters. So over the years, I have learned that there are typically two types of managers.
I call them blockers and builders. Blockers are managers whose value is protecting the team. The team's time, making sure what needs to get done gets done. They are fantastic at keeping an existing machine. Operating blockers tend to be better for departments that have already been built. They don't change much. They just need structure. They just need accountability. Builders are the complete opposite.
Builders are managers whose value is building a department from scratch, or scaling a department from its current stage to an entirely new level. Building managers are typically more entrepreneurial and have already built the thing you need them to build somewhere else. So in this case, you're really not hiring them to manage an existing thing. You're hiring them to build something new, and you're buying their pattern recognition for how to do so successfully.
Generally speaking, once your company crosses 15 full time employees and you enter that valley of death, it is a mistake to hire blockers instead of builders. Because if every department is still dependent upon you to make the strategic decisions, then you remain the company's biggest bottleneck. A company can only successfully scale through that valley of death. When each department has a builder at the helm, capable of growing it to the next level on their own.
Lesson number 13 whatever gets your attention grows and everything else atrophies. A painful lesson I continue to learn is that as long as you are the CEO and or primary operator, you cannot grow multiple things at the same time. You can't grow multiple businesses at the same time. You can't grow multiple departments at the same time. You can't grow multiple marketing channels at the same time.
The only way that you can grow multiple different things at the same time is if you have separate, self-sufficient, and properly incentivized operators in charge of each individual one, and even then the person has to have founder potential. It's really not about how hard they work or how much they care. It's about whether or not they can successfully grow something on their own with minimal to literally zero involvement from you, if that's the case, and if you have the resources to make that sort of bet on someone, then yes, it is possible to grow something in parallel.
But the vast majority of the time people rush this type of decision and don't realize that they are still the primary operator. Which means in any given season of life and business, you have to decide the priority and there cannot be multiple priorities. Priority means one the most important. The good news is whatever you decide to be, the most important will grow.
Anything that gets the majority of your attention will grow. It just will. Most things in life are simply the result of effort, and effort is the result of attention. So more attention equals more effort equals more growth. The bad news is, deciding one thing is the most important also means deciding a handful of other things are less important, and anything that gets less of your attention will either tread water and maintain its current level, or more likely, begin to atrophy.
I have seen this happen over and over again inside our business. Whenever we pick a new marketing channel to focus on and prioritize our other marketing channels, performance stays about the same and then starts to slowly go down. Whenever we pick a new product or a new offer to focus on, and we make that the priority, our other products and our other offers begin to go down in revenue.
And whenever we pick a new department to focus on and we say this is the priority, we're going to build this department, our other departments standard begins to dip, right? More things slip through the cracks. Performance begins to go down. There is no avoiding this problem, which is why business is mostly a game of choosing what trade is worth it at any given time.
Because anytime you prioritize or gain one thing, you will sacrifice and begin to lose another lesson. Number 14 customers don't want more information. They want better results faster with less work. This is one of those things that sounds very simple, but in practice is incredibly hard to execute and keep top of mind when you're selling any kind of info product or running a cohort or you have a training program, your impulse is to give customers everything you want to tell them, everything you know, you want to explain, every little nuance you want to share, random tangential facts or insights or just interesting information.
And that's because you yourself believe everything is important. The problem is nobody wakes up in the morning excited to learn everything. In fact, what customers want way more than to learn is to succeed. They don't actually care or want to know how the sausage gets made. They just want the sausage and they want it right now with minimal effort.
And if that sounds like a hard thing to deliver, that's because it is. Customers value less information, but faster, more guaranteed results way more than they do. Lots of information, but slower, more ambiguous results. So this means that you have to spend more time thinking about what to remove rather than what to add. Do customers really need ten modules?
How can you give them what they need in three modules? Do customers really need eight live sessions? How could you accomplish all of this in a single hour? Do customers really need to know all of these things? How can you give them a checklist to complete to accomplish the same end result in a fraction of the time? Over and over again, I continue to learn this lesson.
Customers don't actually want more stuff. What they want is a higher ROI on their time and their effort, leading to better results faster. By the way, this is fundamentally why you see so many people selling AI prompts and Claude skills now, because in this case, you're not selling information. What you're selling is copy paste this thing to get the same result I get, except in 30s was zero work.
That's why it's such a compelling offer. Lesson number 15 don't anchor your businesses profit or your personal income to your highest performing month. Every step function, change in business profit and or personal income changes the way you see the world. So when I was making ten grand per month in personal income, I thought 20 grand a month was life changing money.
Then when I was making 20 grand a month, I thought 40 grand a month was life changing money. Then when I was making 40 grand a month, I thought 80 grand a month was life changing money. And you probably know where this is going. When I was making 80 grand a month, I thought 160 grand a month was life changing money.
The goalpost never stops moving. The problem is, if you anchor yourself to your businesses highest performing month, then you will begin to make decisions in your life, assuming that that peak won't go away. And if I've learned anything in business, it is that what goes up usually comes back down, and what comes down usually goes back up. I made a whole YouTube video about this idea, which I like to call the genius idiot roller coaster.
When you're up, you think you're a genius. When you're down, you think you're an idiot. And neither extreme is true. So don't make forward leaning decisions based on your peak month. Instead, make decisions based on a rolling 12 month average. So this goes for hiring decisions inside your business. And this goes for personal finance decisions based on your personal income.
You never want to make forward leaning decisions based on an outlier month or an outlier quarter. Lesson number 16 if you truly want to scale your business, you have to be motivated by more than just money. Full transparency the decision we made in 2023 to move away from running ship 30 for 30 cohorts and begin building our premium ghostwriting academy began one of the hardest and most taxing work chapters I have experienced to date as an entrepreneur.
And yes, part of this decision was based on money. We felt we had reached a plateau running ship 30 for 30 as our core business, and wanted to pursue a new, potentially more lucrative business model. High ticket group coaching. Now looking back, I can say this was false. We just didn't know how to do what we were doing better at the time.
So we did what everyone does, which is decide to start something new. But I can only see that in hindsight. But the primary motivator for building PGA, at least for me, was that I wanted to level up as an entrepreneur. I wanted to take on more risk. I wanted to hold myself to a higher standard. I wanted to try to scale something again.
I wanted to build new skills. I wanted to put myself in a position where my deficits would be forced to grow and improve. So my primary motivator for building PGA was not to make more money. And I think to scale any business to a meaningful level, meaningful being like high seven figures or eight figures and above, money can't be the only motivator because it's too hard.
Over the past three years, I have experienced a tremendous amount of responsibility and stress. Just for context, I am already a millionaire, so incrementally more money is no longer motivating for me. What is motivating is knowing that I'm growing even if it's painful. So if you haven't achieved some level of financial abundance in your life yet, and or you don't value building the skills that come with high risk entrepreneurship, you are much better off not scaling your business, because oftentimes, scaling your business does not mean that you make more money, and certainly not right away.
Scaling often means sacrifice and making less money in the short term value of death in hopes of making more money later. So if you're only motivation is making more money now, then don't scale. Just stay small. Stack a little bit of profit by some bitcoin if you want to add a flavor of risk, not financial advice, and enjoy the fact that you operate a small business in cash flow machine that pays for your life and then some, you should only scale if your motivation to grow is more than just money.
Lesson 17 info plus software plus coaching equals compounding profit. One of the things we got accidentally right building ship 30 for 30 is we created a stack of offers that all compounded on each other. I want to be very clear. We did not do this intentionally. We didn't really understand what we were doing at the time. This was done very intuitively and just happened to be the right answer.
I can only see the framework now in hindsight. So ship 30 for 30 was a cohort based writing challenge. This was the info component. Yes, we were also selling accountability, writing with other people, it was gamified, etc. but people were mostly buying how to write online education. Paired with this accountability type, share was the SaaS platform that we built with founder Sam Shaw to pair with it.
So inside of ship 30, we taught people how to write atomic essays online, and then we built the software to help them write and design their own atomic essays. So the info fed the software. On the back of ship 30, we launched a backend upsell called Captain's Table, and this was like a lightweight community mastermind for ship 30 graduates who wanted access to more education and more live sessions with us.
So all of these things together created a pretty amazing flywheel. Chip 30 was a profitable business in itself, but ship 30 also meant that we profitably acquired type share customers. Type share customers became a secondary source of recurring revenue and ship 30 and type shares. Customers both became the people most likely to join captain's table. So whenever I'm building info, products or programs now, I think about how to replicate this stack of offers.
And a few years later, we did this within our premium ghostwriting Academy. Two PGA was a high ticket group coaching program, so this was the info component inside PGA, we educated students on how to use AI to help them land clients and fulfill on client work using our own software called Go Space. This was the software component, and then we would upsell PGA students and Go Space users to our backend program.
Liftoff. This was the continued coaching component, especially in the age of AI where you can vibe code custom software. You should think of software as a highly congruent and niche down product that you can include in your offer stack. The info component educates people on how to use the software. The software retains your power users, and your power users are the ones you upsell to coaching.
Lesson number 18 your team members watch what you do more than they listen to what you say. In 2025, our team grew from around 15 full time team members to over 30 full time team members. So in September we did like 900,000 in revenue and ran our first ship 30 cohort in over a year. In October, we did little over 700,000 in revenue and continued running weekly 2.5 hour free webinars to drive people to PGA.
In November. We did like 850,000 in revenue and ran a huge three day ghost writing challenge, simultaneously building our Black Friday product. November was nuts, and in December we did a little over 800,000 in revenue while still running weekly webinars, expanding the video production team and recording like 1 to 2 months worth of content proactively through the holidays.
I can confidently say that September to December 2025 is one of the most taxing stretches I have ever put myself through as an entrepreneur. The business also did the most revenue had ever done in four consecutive months. So good example of how results tend to follow extreme effort. But after all of that, early December I decided that the best thing for the business was not for me to take my foot off the gas.
Most people chill in December. They throw in the towel. It's the end of the year. They're just going to coast into Christmas. I typically do the opposite, but especially this year. I chose to not do that after that entire stretch and pushing to build an entire new product for Black Friday while having Covid. While doing this three day challenge, while running weekly webinars, I blocked two entire weeks off my calendar to do nothing except hold one on ones.
With all 30 plus team members. Our team had grown a lot in 2025, and we had just pushed everyone through like a hardcore season of intensity, so I felt like it was important to go above and beyond for each and every person and lead by example. And I can't tell you how many team members told me afterwards how much they appreciated it, and how rare it is for the CEO to still be so in the weeds, even as the company grows through multiple layers of management.
So it was a really good reminder of how much people pay attention to your actions and what you do much more than the things you say, but do not embody yourself. Lesson number 19 as soon as you know what to do. Stop consuming content. I'm saying this to myself as much as I'm saying this to you, as soon as you know what to do, the value of consumption falls off a cliff.
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Unknown
The entire point of consumption, at least through the lens of productivity, is to gather information and build pattern recognition of what actions to take that will lead to the outcome you desire. But as soon as you know what those actions are and you have a general sense of how to do them, then the value of more consumption goes down.
At that point, consumption is no longer a benefit. It is actually a distraction. The seasons of business where I have experienced the most progress are also the seasons where I have consumed the least amount of new content and taken consistent action in a chosen direction. And not surprisingly, the seasons of business where I have experienced the least amount of progress are also the seasons where I have consumed too much or consumed too many different things, causing me to chase too many different aspirations and take the least consistent action in any chosen direction.
The only time I have ever found high consumption to be productive is when you have maxed out more of what you're currently doing, but you aren't yet sure how to do it better. When this is the case, the right decision is to consume lots of different ideas and frameworks and ways of thinking, so you can decide what's worth prioritizing inside of your existing vehicle.
But where this becomes a mistake is when you max out more, you've maxed out ever you think you have, and then you go consume lots of different ideas and ways of thinking so you can entertain all the new and different things that you could possibly do. And very quickly this turns into productive procrastination and shiny object overload. Consumption should always be in service of taking the right actions in a specific chosen direction.
If not, then consumption works against you. And lesson 20. Every time you change what you want, you disrupt compounding and start over. This is probably the lesson that I've been thinking about the most. I became an entrepreneur in September 2016. That is when I quit my 9 to 5 job and went all in on working for myself. Since then, I have changed what I wanted more times than I'd care to admit.
So end of 2016, when I quit my job, all I wanted was to pay my rent as a freelance writer and ghostwriter and work toward becoming a full time author. That's what I wanted. Then in 2017, I changed what I wanted and decided to scale my ghostwriting work into an agency and build a real business. Then in 2018, I changed what I wanted and decided to bring on two angel investors inside my agency and try to scale to the moon as this like hybrid agency and software startup, which was a monumental mistake.
In 2020, I changed what I wanted, decided I didn't want to run a high risk startup or agency anymore, fired everyone, downsized, and went back to being a highly paid solopreneur. At this point, I circled back and said, I want to work toward being a full time author. I went back to my original want. Then in 2021, I changed what I wanted and decided to scale ship 30 for 30 with Dickey and build another business and paid newsletter at the same time called Category Pirates.
Then in 2023, I changed what I wanted and exited Category Pirates after growing it to multi seven figure business in two years, and decided that I wanted to build a more advanced business with Dickey, which is when we started PGA, our premium go training academy, and in 2025 I changed what I wanted and decided I wanted to try and scale PGA to the moon and spent hundreds of thousands of dollars on joining masterminds and spent millions of dollars running paid ads.
I decided I want to play that game, and I remember making each of these decisions. At the time, it seemed like the right decision based on the information and skills that I had. But looking back, I can see now the pattern with significantly more clarity. Every time you change what you want, you essentially start over. You disrupt compounding of your previous want and you swap it for something else.
So as I move into this next chapter of life in business, this is a lesson I'm taking to heart. I'm thinking about this a lot, and I'm trying very hard to only play games that I can see myself playing for ten years or more. Now. Obviously, if I acquire new information and decide the right decision is to change course, right, change what I want, I will.
But after a decade of being an entrepreneur, I can't help but wonder where I would be today if I hadn't changed what I wanted so many times and just committed to the same goal for ten years, instead of changing goals every 2 or 3 years.