The Art & Business of Writing is my free newsletter on how to write in the digital age, and how to make money doing it. New posts every Monday!

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Dear Writer,

I made my first $1 writing online in 2014.

I wrote a viral answer on a little-known website at the time called Quora about my bodybuilding transformation, and how I had gone from weighing less than 100 pounds as a senior in high school to putting on 70 pounds of muscle and becoming a shredded bodybuilder by age 24.

And at the top of the short story I wrote, I put a Before & After image—showing the transformation:

That Quora answer ended up on the front page of Reddit, and accumulated over a million views in just a few days.

And I got probably a hundred emails from guys who said, “I look just like you did, and I want to put on muscle too.”

Which is how I came up with the idea for my very first digital product:

That Quora answer ended up on the front page of Reddit, and accumulated over a million views in just a few days.

And I got probably a hundred emails from guys who said, “I look just like you did, and I want to put on muscle too.”

Which is how I came up with the idea for my very first digital product:

An eBook called Skinny to Shredded.

And I made two of them:

• Skinny to Shredded: Workout Routines

• Skinny to Shredded: Nutrition Guide

I spent the entire weekend putting them together:

• I bought www.nicolascole.com - which is the same domain I use as my primary website today.

• I built a simple 1-page website using Squarespace.

• I wrote both eBooks in Microsoft Word.

• I used some pictures I’d taken with my bodybuilding friends at the gym, and some I’d taken from trying to become a fitness model

• And I asked a designer at the advertising agency I was working at if she would help me create the covers (and I bought her lunch as a Thank You)

Then, Sunday night, just two days later, I turned my website live, made my eBooks available for sale, and added a link to the products at the bottom of that viral Quora answer.

It’s still there on Quora if you want to take a look.

And I will never forget sitting in our Monday Morning All-Hands meeting.

My phone in my pocket was just buzzing non-stop.

• Stripe notification

• Stripe notification

• Stripe notification

By lunch, I had earned more money selling eBooks than I would make working my full-time job all week!

That simple eBook series is how I made my first $1 online.

And my first $100.

And my first $1,000.

And my first $5,000.

For months thereafter, it just kept selling. Not a ton. But enough to put an extra couple hundred bucks in my pocket each month—which was a lot for me back then.

More importantly, it introduced me to the idea of leverage on the Internet. You can create something once, but continue to sell it forever. Even a decade later, whenever I tell this story, people STILL ask me where they can buy those old eBooks.

That moment of making my first $1 online changed my life, and introduced me to a completely different way of thinking about what it means to provide for yourself in the digital age. The old path of “go to college, get a job, work for 40 years, then retire” isn’t the only path anymore. If anything, it’s dying and no longer a viable path at all. And it’s being replaced by a new path that is more flexible, more lucrative, and most of all, more fun.

(And remember, I was doing all of this back in 2014… before all the incredible tools and platforms we have today!)

If I was starting over today, here’s the full roadmap I would follow to make my first $1 online—and hopefully a lot more.

And for context, since I launched that first digital product way back in 2014, I have generated over $30,000,000 across 8 different business models building digital products and providing services online:

1. I have generated over $1,000,000 self-publishing non-fiction books.

2. I have generated over $1,000,000 with paid newsletters.

3. I have generated over $1,000,000 with SaaS.

4. I have generated over $3,000,000 with consulting.

5. I have generated over $3,000,000 with low-ticket digital products.

6. I have generated over $5,000,000 with cohort-based courses.

7. I have generated over $5,000,000 with ghostwriting services.

8. And I have generated over $10,000,000 with high-ticket group coaching.

I only share that so you know where my advice is coming from, and to also show you there are lots of different ways to monetize your knowledge online.

So first, let’s walk through the roadmap at a high-level. And then, go through each step—so that by the end of this, you know exactly what to do, why you should do it, and how to make your first $1 online (and hopefully, a lot more money thereafter).

The Roadmap To Your First $1 Online

There are 7 steps to making money online.

None of them are hard. And the roadmap from where you are today to where you want to go is very straightforward.

The hard part is staying committed long enough to see your sacrifices turn into Stripe notifications.

The roadmap goes like this:

• Step 1: Pick a niche. The most effective way to make money on the Internet is to become known for a niche you own—and the smaller, more specific the niche, the more likely you are to become what I like to call “Niche Famous.” You want people to associate you with that niche. Because the more people associate you with a specific niche, the more products and services you can launch within that niche over a prolonged period of time. One of my favorite examples is Ryan Holiday. What’s his niche? Stoicism. He writes articles about Stoicism. He has a newsletter about Stoicism. He has a podcast about Stoicism. He’s written 10 books about Stoicism. And guess what? When he goes to his publisher and says, “I’m ready to write another book,” and they hand him another 7-figure advance, what do you think the topic of the book is going to be? The book is going to be about Stoicism! This is the whole game. You don’t want to become known broadly. You want to become known for a niche you own. And I’m going to walk you through my framework for identifying the perfect, most lucrative niche for you.

• Step 2: Start writing online. The way you validate demand for any product or service you want to monetize inside of a niche is to start writing online. And by the way, if you don’t know what niche or topic you want to commit to, then the answer is to write about anything and everything that is interesting to you and see what “sticks.” What’s resonating with readers? What do they want more of from you? What questions do they have? I usually tell people it takes at least 30 days of writing and publishing every single day to gather enough data to get a sense of which direction you should move next—which is the whole reason why we started Ship 30 for 30. It’s a 30-day writing challenge that holds you accountable and forces you to write and hit publish every day for 30 days. By the end of the month, you have 30 pieces of published content (the foundation of your library), and more importantly, you have 30 data points. Those data points will tell you where there’s customer demand.

• Step 3: Start a newsletter. To sell any product or service, you need emails. To build an email list, you need to write online. And to effectively write online and build a niche audience, you need to commit to a niche. See how each of these steps connect to each other? Think of your email list as the engine of your entire business. The more people you have on your email list, the more money you will make. And I’ll walk you through my strategy for turning social content into weekly newsletters, but the big idea here is that your newsletter should really just be the longer-form version of the same topics you are writing about online.

• Step 4: Create an offer. Once you’ve committed to a niche, started writing online about that niche, and started a weekly newsletter in that niche, now it’s time to make your free readers a paid offer! An offer is just how you solve someone else’s problem. And how you solve someone else’s problem is what dictates your business model. For example, if you solve someone else’s problem with information, maybe your business model is selling eBooks (like I did), or starting a paid newsletter, or launching a course. If you solve someone else’s problem with custom-tailored advice, maybe your business model is selling consulting. If you solve someone else’s problem by doing the work for them, maybe your business model is selling services. You get the idea. And I’ll help you decide which offer and business model is right for you, based on your chosen niche, skills, and goals.

• Step 5: Make your first $1. If you have a product for sale, in a niche, that helps someone solve an urgent, painful, and ideally expensive problem in their life or business, and you write about that same topic on a social platform every single day for 90 days in a row, you will probably make your first $1 online. You might even make your first $1,000 or $10,000 online. I have no idea. I don’t have control over the decisions you make or how consistent you are. But what I do know is that it is very, very, very hard to not-make-money online if you have a helpful product for sale, in a niche, and then you consistently create helpful content in that niche for a prolonged period of time. None of these things are hard. The hard part is not giving up before it happens. (And by the way, putting a product up for sale, or starting to sell a service, is very simple. I’ll walk you through it.)

• Step 6: Gather testimonials. The biggest mistake I made with my first digital product is that I put it up for sale, I made some money, and then I never improved the product and I never collected customer testimonials to use in future marketing. In hindsight, I bet I could have made my first $100,000 online if I had just done those two simple things: make the product better, and use customer testimonials to sell more products. Which is exactly what you should do—and I’ll give you a checklist you can use, once your product is live and selling, to generate even more revenue.

• Step 7: Monetize in more ways! The last step, once you’ve made your first $1 online, is to start stacking different business models on top of each other so you can generate more revenue per customer. For example, if you have a paid newsletter, why can’t you downsell subscribers on specific eBooks? If you sell services, why can’t you upsell your best clients on even more expensive consulting? If you sell courses, why can’t you cross-sell other courses and digital products? I have generated millions of dollars selling individual products and services. But I have generated tens of millions of dollars, selling “other things” to existing customers. This is the whole secret to making money online, and why the hardest part of the journey is starting. Because once you start becoming known for a niche you own, start writing online, start shipping your weekly newsletter, and start making money, momentum begins working in your favor.

So, that’s the roadmap.

Is it simple? Yes.

But is it easy? Absolutely not.

“How to make money online” is literally one of the most popular topics on the Internet. Everyone wants to do it. But the reason not everyone is successful is because they think there’s some secret key on the keyboard that, when you press it, gives you “passive revenue” with no work required.

And that’s just not true.

Making money online, in any niche, selling any type of product or service, takes work.

But once you build the skills, master the fundamentals of writing online, and learn how to monetize in multiple different ways, you can make money forever.

So, I want to set you up for success.

Let’s walk through each step—so you know exactly what to do, why it’s important, and how to do it correctly.

Step 1: Pick a niche.

Your niche should be an industry where you have what I like to call an Information Advantage.

An Information Advantage just means you know more things about this industry than the average person.

For example:

• If you’ve worked as a nurse in a hospital, you have an Information Advantage in healthcare.

• If you played hockey as a kid, you have an Information Advantage in athletics.

• If you are obsessed with Pokémon cards, you have an Information Advantage in collectables.

The easiest way to identify where you have an Information Advantage is to audit these 3 areas of time spent:

• Jobs: Any job you’ve ever had has given you an inside look at that particular industry. Which means you know things (even if they’re simple, fairly basic things) the average person does not—because they’ve never worked a job in that industry before. For example, if you’ve worked in retail, you inherently know more about “working in retail” than someone who has never worked in retail before. This also applies to people close to you who hold jobs of their own. For example, my dad is a spine surgeon. Just by being his son, I have soaked up lots of random knowledge and terminology when it comes to spine surgeries. In a small way, this gives me an Information Advantage.

• Hobbies: Anything you’ve ever gotten interested in, either as a kid or an adult, means you spent a prolonged period of time learning about it. Which means you have an Information Advantage, and know things the average person doesn’t. For example, if you spent your college years teaching yourself music production, then you know more about “music production” than someone who has never taught themselves that skill before. This also applies to people close to you who expose you to hobbies and interests of their own. If your best friend is a pilot and flies planes, you probably don’t even realize how much you’ve learned just by being their friend and listening to them talk about their interest. In a small way, this gives you an Information Advantage.

• Experiences: Anything you have personally experienced means you have an Information Advantage in that particular experience—and the more rare or unique the experience, the more rare and unique the Information Advantage. For example, if you’ve experienced a parent overcoming a sickness, that’s an Information Advantage. Or if you’ve experienced traveling to a certain country, or done something crazy like jumped out of an airplane, those are Information Advantages. You know more about those things than people who have never done those things before.

For example, back in 2016, I was a columnist for Inc Magazine. I wrote a daily column about creativity and business. So when I started ghostwriting and providing writing services to founders and business owners a year later, in 2017, and they would ask me to help them get their own writing in major publications, I could tell them. Because I was already doing that for myself.

I had an Information Advantage.

You should not choose a niche, or pick a topic without some sort of Information Advantage.

This is probably the biggest mistake people make when they decide to start writing and creating content online, with the hopes of one day making money.

They think their niche can be ANYTHING. And it can’t. No one is going to listen to you talk about a topic you know nothing about. The ONLY reason “people follow people” online is because there is an Information-Advantage-trade happening.

• You know things about this topic most other people don’t.

• People follow you to learn those things in a fraction of the time—so they don’t have to go through all the work you had to go through in order to learn the things you know now.

That’s it.

And if that doesn’t convince you to start with a niche where you already have an existing Information Advantage, here’s an even more logical way of thinking about it.

When it comes to making money on the Internet, there are lots of marketing & monetization skills you need to learn.

• You need to learn how to write clearly

• You need to learn how to generate infinite ideas within a niche

• You need to learn how to hook people’s attention

• You need to learn how to retain people’s attention

• You need to learn how to move readers from social platforms over to your email list

• You need to learn how to write compelling emails—compelling enough to keep them subscribed, and ultimately buy something of greater value

• You need to learn how to build a landing page

• You need to learn how to write a landing page

• You need to learn how to process payments on a landing page

• You need to learn about upsells and downsells to increase each customer’s lifetime value

The list goes on and on.

And none of these skills are hard to learn. Each one maybe takes 5 or 10 hours to reach a moderate level of proficiency. That’s nothing. That’s a Saturday morning. That’s a weekend.

But now imagine trying to learn all of these skills, while simultaneously applying them to a niche you know absolutely nothing about. You have no Information Advantage.

Well, if you thought building all those marketing & monetization skills was “a lot of work,” congratulations, because the work just doubled. Now you have to learn all of those things AND start from the very beginning learning about an industry you’ve never worked in, never had a hobby in, and never experienced—but you picked it because it seemed popular, or lucrative, and you thought that was a shortcut to success.

So, here’s a little secret for you: the shortcut is always the longer road in disguise.

And you would get to where you’re trying to go a whole lot faster if you just started with something you already knew a lot about.

Now again, an Information Advantage does not mean you have to have won some huge award, or made millions of dollars. An Information Advantage quite literally just means you know more than someone who hasn’t done that thing before. A silly example I like to use with students inside our AI Writing Skool is: imagine you love reading Thrillers, and you want to start writing online about the best Thrillers to read. You want to start a Thrillers Book Club.

So, what’s your Information Advantage?

Well, it might be something like: “Over the past 10 years, I have read over 500 Thrillers.”

That’s all it has to be.

Your Information Advantage is just context.

It helps the reader understand why they should listen to you.

And you might not realize it, but you look for this signal every single day when you scroll on your preferred social platform. The next time you’re scrolling X or LinkedIn or TikTok or Instagram Reels or YouTube, pay attention to what grabs your attention. It’s almost always a piece of content that does 3 things:

• Speaks directly to a niche interest of yours.

• Promises to help you either solve a problem or help you achieve an outcome.

• And starts with some form of context—meaning the writer or creator tells you their Information Advantage.

Usually something like:

“I’ve been an interior designer for 10 years. So if you want to remodel your kitchen, let me give you a few tips to make it look professional without blowing through your budget.”

This simple “hook” is doing all 3 of those things!

• It’s speaking directly to a niche interest: interior design.

• It’s promising to help achieve a desired outcome: remodel your kitchen without blowing through your budget.

• And it begins with the creator sharing their Information Advantage, which is really just context to why you can trust them: they’ve been an interior designer for 10 years!

So when you “niche down,” all you’re really doing is committing to write and create lots and lots of content about a specific topic in an industry where you have some sort of Information Advantage.

Now, whenever I explain this idea of niching down in an industry where you have an Information Advantage, I always get asked the same 3 questions. And the thing is, they’re not even really questions. They’re more objections to this strategy, phrased as questions. So not only do I want to answer them for you, but I want to help you understand why these objections are incorrect and just clever ways you’ve convinced yourself to avoid taking action.

Question #1: “But Cole?! If I pick a niche, won’t that exclude certain people? Won’t that mean I’ll be limiting my opportunity? I won’t make any money!”

This is, by far, the biggest question and objection people have when it comes to niching down.

First of all, people think that when they pick a niche, that means they “can’t speak to everyone.”

And that’s correct. You can’t speak to everyone. Because when you try to speak to everyone, you end up speaking to no one.

For example, just think about who you follow on social media.

Do you follow one person for “everything?” No, of course not.

• You follow one person for fitness advice.

• And you follow another person for travel recommendations.

• And you follow another person for investment strategies.

• And you follow another person for news and trending topics.

• And you follow another person for memes and pop culture.

It would be impossible for you to speak on “all topics” for “all people.”

Second, it’s not until you commit to a niche for a prolonged period of time that you realize just how deep each niche can go.

For example, I’ve been writing about digital writing and writing on the Internet since 2015. That’s over a decade! And today, after writing thousands and thousands of articles and newsletters and Tweets, and making YouTube videos, and writing books, and recording podcasts, all on the same topic, I am STILL coming up with new ways of explaining concepts to readers.

The deeper you go in a niche, the more you realize how much more there is to say.

But if you haven’t done this work yet, then yes, it’s very easy to think that you can write about 10 different niches and be the best person to listen to in each of them.

We call this blissful ignorance.

Question #2: “But Cole?! What if I have lots of interests, and lots of Information Advantages? Which one should I pick?”

I get it. I have lots of interests and Information Advantages too.

• When I was 17 years old, I was one of the highest-ranked World of Warcraft players in North America. I have an Information Advantage in online gaming.

• When I was in college, I completely changed my physique and became a bodybuilder. I have an Information Advantage in fitness and bodybuilding.

• When I graduated from college, my first job was working as a copywriter at an advertising agency. I have an Information Advantage in advertising, marketing, and how ad agencies work.

• When I quit my job in 2016 to work for myself, I started and scaled a ghostwriting agency to millions of dollars in revenue. I have an Information Advantage in ghostwriting.

I’ve built multiple 7-figure companies. I also love wine and luxury sports cars. I’m a tequila snob. My siblings and I all grew up playing piano and violin, and I played classical piano for 20 years.

All of these are potential “right” answers.

So, here’s the exercise I coach writers through inside our writing programs to help them identify the best Information Advantage for them.

• First, list out every Job, Hobby, and meaningful Experience you’ve ever had. What you’ll find is you have a lot of different Information Advantages to choose from—most of which you probably take for granted.

• Next, looking at that list of 10 or 20 Information Advantages, stack-rank them by knowledge. Out of that entire list, which one do you know the most about? Then which topic second? Which topic third? You should end up with a list that is organized from most-knowledgeable to least-knowledgeable. For example, one of my best friends is a therapist and I have been in therapy for over a decade. I’m a huge proponent of it. So yes, I do have an Information Advantage in this area, but I would hardly consider myself qualified on the topic. So that would probably be near the bottom of my list.

• Lastly, take the top 3-5 Information Advantages you are most knowledgeable about from your list, and start writing about those topics online. You don’t have to commit to a niche yet. But at least this gives you some direction. These are the topics where you possess the most working knowledge. So, write about them, and then out of those 3-5 topics, see which one or two perform the best.

And the way you should measure performance is:

1. Which of these topics do readers find most interesting? You can identify this, even in small ways, by looking at views, likes, and comments relative to all other posts. For example, if you write 10 Tweets and 9 of them all get 100 views but 1 of them gets 300 views, that is a 3x difference. That is a data point! A lot of times, people discount these early signals because they think what they’re looking for is a post with a million views. That’s not true. There might be more zeroes, but the logic is the same. Write lots of things. Look for the tiny outliers. Double-down on those. Repeat for a decade.

2. Which of these topics do YOU find most interesting? As you write about these 3-5 different topics where you have a strong Information Advantage, I promise, you will very quickly start to realize which ones you enjoy writing about the most and which ones you thought you would enjoy writing about but actually find boring. This is an important part of the learning process.

The final answer to what your “niche should be” is then the result of this exercise, checking these 3 boxes:

• ✅ It’s a topic where you already possess a strong Information Advantage.

• ✅ It’s a topic you see performing well with readers in the form of engagement (even if it’s small).

• ✅ And it’s a topic YOU enjoy writing about—and the more you write about it, the more you realize you have to say.

Whatever topic checks those 3 boxes should be your niche.

And if you want to make money online, then you should commit to that niche for a prolonged period of time.

Because none of the outcomes you desire happen overnight.

Question #3: “But Cole?! I understand all of that… but I want the shortcut. I just want money to rain down from the sky. Can you just tell me what the most lucrative niche is so I can do that?”

Here’s the honest answer:

The most lucrative niche for me is going to be different than the most lucrative niche for you.

That’s because how lucrative a niche is has very little to do with “the niche itself,” and much more to do with the writer or creator who commits to it.

For example, I could tell you that the most lucrative niche in the world right now is advice for Millennial women dealing with postpartum depression. If you write about that topic and launch digital products in that niche, you can crush and probably make loads of money. Why? Because that demographic is chronically online, they love to shop, they have high purchasing power, they tend to control a lot of the purchasing decisions for the household, and they have an urgent and painful problem they desperately want help solving.

OK great, there’s your answer.

The problem is, you aren’t going to go pursue that niche.

Why?

• Because you probably don’t have an Information Advantage in that niche. So now you see the problem. You can’t help people solve a problem you’ve never experienced and know nothing about.

• And because you probably aren’t interested in that topic. So even if you “know” it has the potential to be lucrative, you aren’t going to stay consistent and disciplined and interested long enough to successfully monetize it.

Which is why I tell writers, over and over again:

The best niche is the one you don’t give up on.

Whatever topic you know you will still be interested in 10 years later is the right answer. Because I promise, it doesn’t matter how lucrative you think another niche is… if you don’t have an Information Advantage in it, and you aren’t genuinely interested in continuing to learn about it, you aren’t going to succeed. You’re going to get really excited about it for 2 days and then give up. You’re going to get bored. And when things get hard, or monotonous, you aren’t going push through. And then you’re going to avoid taking accountability for your lack of commitment and blame the niche instead, hoping that if you pick a different niche, an even more seemingly lucrative niche, the problem will magically disappear and THEN money will rain down from the sky.

This is the vicious cycle people stay in for years, sometimes decades.

The problem is never the niche.

The problem is you keep trying to find the shortcut, instead of just committing to a topic you know a lot about and want to help other people become knowledgeable about too.

Step 2: Start writing online.

Once you’ve identified your niche, the easiest way to validate demand for any future product or service is to start writing online.

And there are 5 formats you need to learn how to write if you want to build a niche audience.

Format #1: Short-Form

These are bite-sized pieces of text-based content, like Tweets. But these can also double as scripts or talking points for short-form videos, TikToks, Instagram Reels, YouTube Shorts, etc.

Format #2: Atomic Essays

These are 300-word essays short enough to be written in 30 minutes or less, but long enough that you can start to practice all the fundamental skills of writing online: headlines, formatting, writing rhythms, etc. This is a format we invented for our beginner writing program, Ship 30 for 30, and it has since become an Internet phenomenon. Even people who have never taken Ship 30 write Atomic Essays using our software, Typeshare.

Format #3: LinkedIn Carousels

These are listicles turned into multimedia slideshows that are the highest-performing format on LinkedIn. These Carousels can also double as Carousels on Instagram, or other image-based social platforms like Pinterest.

Format #4: X Articles

These are 800+ word blog posts published as articles on X, but can also be republished across your website, Medium, even your weekly newsletter. Long-form articles can also be the foundation of your entire content strategy, and you can extract dozens of short-form posts from each one.

Format #5: AI Prompts

Lastly, you can get leverage on your writing skills by turning your favorite AI platform into your own personal Writing Assistant—and then turning those prompts into more content/assets for your niche. For example, since my niche is “Digital Writing,” I often share writing, editing, brainstorming, and outlining prompts with my audience.

I train writers & creators on how to write all 5 of these formats inside our AI Writing Skool.

So if you’re brand new to writing online, this is an easy place to start. Because each format has different rules, and each platform has different nuances. I like to think of each format and social platform as a different “sub-language” of Digital Writing—or writing in the digital age.

Now, I know what you’re probably thinking.

“But Cole?! Which platform is the best? How do I go viral? What time of day should I post?”

To which I (kindly) say: you’re asking the wrong questions.

Everyone loves to get fixated on all these little incremental decisions that, in the long run, really don’t matter.

My personal point of view, and the POV I’ve been preaching for over a decade, is that there is no “one perfect platform” and the performance of any individual post is not what’s important. I’ve gone viral more times than I can count, across a wide variety of different platforms. I’ve generated over a billion views on my writing. And I’m telling you, going viral is not what solves your problems, or allows you to build a business and make money online.

My entire thesis for writing in the digital age is that it’s all about the library.

Let me walk you through this:

• The bigger your library of content in a niche, the wider your footprint, the more likely you are to become “Niche Famous.”

• The more you establish yourself as a leading voice in a particular niche, the more people who become interested in that niche become interested in listening to you.

• The more people who follow you, the more you email list grows, the more potential customers you will attract.

• The more customers you attract, in a niche, the more you can sell those customers (not once, but many times over many years).

• The more you successfully monetize a niche, the more excess cash you will be able to reinvest in yourself, your own content, and continuing to expand your footprint in your niche.

Until eventually, you and the niche become synonymous. You have successfully become known for a niche you own.

On top of that, your library of content is yours. You own it. Which means you can do whatever you want with it.

• When a new social platform comes out, you can copy/paste all your highest-performing posts over to that new platform and power-level your niche dominance there too.

• You can turn Tweets into TikToks, TikToks into Instagram Reels, Reels into YouTube Shorts, a bunch of shorts all on the same topic into a YouTube long-form video, etc.

• You can turn articles into newsletters, newsletters into articles.

• You can smash 10 articles or newsletters on the same topic together and self-publish it as a book on Amazon.

• You can turn your book on Amazon into a lead magnet to capture more emails.

• You can expand your book into an online course.

• You can expand your course into a coaching program and curriculum.

The list goes on and on.

In fact, if you want an example, this is what I did with my last book, Writer Career Paths.

I wrote this entire book online. I wrote each chapter as a newsletter, first.

Then, when I was done, I smashed all those newsletters together, did a little light editing, and self-published it on Amazon.

And now that book generates an extra $1,000 per month.

The point is, the most valuable asset you could possibly build for yourself is a library of content, in a niche, over a prolonged period of time.

Because you can re-use all of that content, and double and triple and quadruple monetize all of that content, for decades into the future.

The library matters more than virality.

Step 3: Start a newsletter.

I have been writing online since 2007.

Over the past 20 years, digital distribution and social platforms have changed a lot—the biggest change being from follower-based content to interest-based content.

For example, back in the early 2010s, if you had 10,000 followers and you made a post, that post got shown to a meaningful chunk of your followers. That was the whole point of building an audience on social platforms. More followers meant more distribution.

But then, around 2016, social platforms started to change. Your newsfeed stopped being about who you followed, and started being about topics of interest—showing you posts from people you didn’t follow, but who created content within a niche the algorithm knew you cared about. All of a sudden, followers didn’t matter. What mattered was how well your content performed when the algorithm presented it to groups of people interested in that topic. If people engaged, platforms would distribute your content to wider and wider audiences (causing you to “go viral”), and if your content didn’t perform, then your distribution would fall of a cliff—regardless of whether you had 1,000 followers or a million followers.

Today, followers are an almost meaningless metric.

I have helped over 15,000 people start writing online, and beginners love to think that “more followers” will somehow solve all their problems.

A couple things here:

First of all, everyone starts at zero. When I started writing on Quora back in 2014, right out of college, I didn’t create a new account, “win the lottery,” and get a 5,000-follower head-start. Every single person, who has ever built an audience online, started at 0.

Second, followers are a lagging indicator. You write valuable content in a niche and THEN people follow you. People don’t follow you and THEN you start writing valuable content. You have to build the skill before people will give you their attention.

Third, social platforms are no longer follower-based. They are interest-based. Which means having more followers doesn’t actually give you an advantage. You could have hundreds of thousands of followers and still write content that only gets 1,000 views. I know, because I have over a quarter million followers on X and the majority of my posts reach less than 1% of that audience. Conversely, you could start a brand new account, have 0 followers, and go nuclear viral on your first post if the content is good enough. I just watched it happen. I went on this brand new podcast on YouTube, and the guy’s very first interview, on a brand new channel with 0 subscribers, got 500,000 views in its first week.

Which means the whole point of writing and creating content on social platforms is not really to build an audience on rented, digital land.

The point is to do two things:

• First, just focus on building a library of helpful content in a niche over a prolonged period of time.

• And second, use the distribution social platforms provide to bring your rented audience over to an owned platform, like email.

How do you do that?

By starting a weekly newsletter—and then reminding readers on social platforms, “Hey, by the way, I also write about this same topic, even more in-depth, over here.”

Your newsletter is just the expanded version of your social content.

It’s just “more.”

In Ship 30 for 30, we call this Lean Writing.

Lean Writing is the strategy of expanding short-form content into long-form content, and compressing long-form content into lots of short-form content.

This is how you go from…

• A ****Viral Tweet

• To an ****Atomic Essay

• To a ****LinkedIn Carousel

• To an X article

• To an eBook

• To a paid digital product

• To an online course

• To an entire business

Every single idea or topic you write about in a niche can be expanded or compressed into a wide variety of different content formats.

For example, I recently wrote a long-form newsletter on the 6 Revenue Streams To Become A 6-Figure Fiction Writer. 3,500 words. Lots of examples. Lots of images. It took me almost 10 hours to write, start to finish.

But I could also compress this entire 3,500 newsletter into 280 characters, by just writing a Tweet that lists out the 6 revenue streams to earn 6-figures as a fiction writer:

• Books

• Beta-Reader Community

• Paid Newsletter

• Digital Products

• Affiliate Commissions

• Paid Workshops

So, why would someone read a 3,500 newsletter on the exact same topic if they could just read the 280-character Tweet that gives them all the answers?

One word:

More.

The only difference between short-form and long-form content is More.

• More tips

• More stories

• More lessons

• More reasons

• More mistakes

• More examples

• More explanation

More, more, more.

Your newsletter does not, and should not be about a completely different topic.

It should be about the same topics, in your chosen niche, just More.

Step 4: Create an offer.

Writing and creating content on social platforms is how you get access to unlimited distribution. Each social platform has hundreds of millions, if not billions of users. I promise, no matter what niche you pick, your target readers are there. You just have to stay consistent long enough for them to find you—and for your content to appear in their feed.

Your newsletter is how you retain your most engaged readers, and build a list of potential customers. Anyone who voluntarily moves from a distracting, fleeting social platform over to your email list is essentially raising their hand saying, “I am interested in this topic. I find the content you are creating helpful. And I might even be willing to give you money if you help me solve even more urgent, more painful, more expensive, more valuable problems in my life and/or business.”

Which means your Offer is really just how you solve someone else’s problem, or help them unlock a desirable outcome. And there is no one right answer. In fact, there might be multiple right answers. You could help someone by selling them more advanced information. You could help someone by coaching them 1:1. You could help someone by doing the work for them. Eventually, as you build each of these marketing & monetization skills, you may end up helping them in all of these different ways! That’s the goal.

The magic word here is Congruence.

Where beginners tend to mess up is they think their Social Content needs to be different from their Newsletter, which needs to be different from their Offer.

No, no, no.

Your Social Content is the short-form version of your Newsletter Content.

Your Newsletter Content is the longer-form version of your Social Content.

And your Offer is the even longer, even more valuable version of both your Social Content and your Newsletter Content.

For example, I write about Digital Writing, how to write on the Internet, and all the different ways you can monetize writing in the digital age.

• I write about these topics on social platforms like X, LinkedIn, and Substack, and create videos on these topics on YouTube and Instagram.

• But I also write about these same topics in MORE depth and MORE detail in my Art & Biz of Writing newsletter.

• And then I also write about these same topics, in even MORE detail, with MORE examples, giving writers MORE templates, and MORE AI prompts, with MORE access, answering MORE questions on live sessions and in 5-day sprints, or 2-week bootcamps, or 30-day cohorts inside our AI Writing Skool.

Think of it like a supply chain.

You want to move rented readers from social platforms… over to an owned platform like email… all the way to the end with some sort of paid product, community, or service.

And when it comes to supply chains, Simplicity Is Velocity.

The more congruent each step is to the one before it, the more likely people are to keep moving from Point A to Point B to Point C.

The less congruent each next-step is to the one before it, the less likely people are to keep moving—because they don’t know what to expect next.

What kind of Offer should you create?

Well, there are 9 business models you can choose from—and they all work.

I know, because over the past decade, I have generated over a million dollars in revenue inside each of these different business models:

• Software - We did this with our SaaS platforms Typeshare and Ghostbase. With AI, the average person can now vibe-code a lightweight piece of software and charge a subscription fee for using it. This is the hardest Offer type for the average person to execute, but it’s becoming easier and worth mentioning.

• Self-Publishing - I’ve written 10+ books on Amazon, including the best-seller The Art & Business of Online Writing. You should think of your newsletter as a vehicle for writing book chapters on a weekly basis. And as your pile of newsletters on a topic begins to grow, eventually you will be able to smash them together and self-publish them as a product.

• Digital Products - I have built nearly a dozen different stand-alone digital products at this point, including Category Newsletter Creator, Low-Ticket Launchpad, Substack Starter Kit, and Self-Publishing Studio. A digital product is usually a text & video course on a specific topic, helping your target customer solve a specific problem and/or achieve a specific outcome. The average price point for these types of digital products is between $99 and $350.

• Agency Services - From 2017 to 2021, I built the first ghostwriting agency for founders & executives, scaling to millions of dollars in revenue. Providing a service, or scaling into an agency, just means instead of teaching someone how to solve a problem or achieve an outcome themselves, you are getting paid to do the work for them.

• Paid Newsletters - Our paid newsletter, Write With AI, is one of the biggest education newsletters on Substack. It does over $300,000 in annual recurring revenue, and over $1,000,000 in annual revenue as a vertical within our portfolio of writing businesses. Paid newsletters are where you gate highly specific, technical, or exclusive content behind a paywall, usually charging $9 to $49 per month, depending on the category of content.

• Paid Communities - We run a large community called AI Writing Skool that does over $500,000 per year in annual recurring revenue, and over $1,000,000 per year as a vertical between sprints, bootcamps, and cohorts. A paid community is basically like combining a paid newsletter and a suite of digital products together, and usually costs between $9 and $99 per month, again depending on the category of content.

• 1:1 Coaching/Consulting - In 2023, I built and exited a company called Category Pirates that was another 6-figure paid newsletter on Substack with a multi-7-figure consulting business on the back of it. Coaching or consulting is really just the high-end version of a digital product. Instead of selling people a text & video course for them to go through on their own, coaching usually just means repeating all that same information to someone on a 1:1 call (or set of calls), live. You’re just personalizing it to them.

• Cohort-Based Experiences - I am the co-founder of the largest writing challenge on the Internet, called Ship 30 for 30, that has helped over 15,000 people start writing online and generated millions of dollars in revenue. A cohort-based course usually combines a digital product-style curriculum, with live sessions and community elements that last for a finite amount of time. In the case of Ship 30 for 30, students would participate in the challenge for 30 days.

• Hybrid 1:1 + Group Coaching - This is the model we’ve run for our more advanced program, Premium Ghostwriting Academy, which has has helped over 2,000 students enter the lucrative world of ghostwriting and has generated over $10,000,000 in total revenue. Group coaching is typically in the price range of $5,000 to $10,000 and involves pairing students with coaches to guide them through a constructed curriculum—along with live sessions, community elements, and ongoing education. This is, by far, the most complex Offer type because it involves so many different fulfillment mechanisms.

I share all of this to help you understand that every single business model and offer type can work—and has the potential to scale to millions of dollars in revenue.

Each one just requires different skills, and has different pros and cons.

So, let me give you a quick crash course on how you should make this decision for yourself.

The Right Offer For YOU: Skills x Time Horizon

A lot of times, people choose to pursue a business model or Offer type because it seems lucrative, or easy, or they see someone else succeeding with it and think, “I guess that’s what I should do too!”

But the truth is, these are all bad ways of making this decision.

Every Offer type can be lucrative. Every Offer type can be scaled to millions and millions of dollars in revenue. And I promise, the grass is always greener on the other side of the fence. Every Offer type seems easy when someone else is doing it, and every Offer type seems hard and annoying as soon as you choose to pursue it.

Which means the right way of making this decision comes down to two things:

• Skills: What are you good at? What do you want to get good at? What type of business do you want to run?

• Time Horizon: How fast do you want or need to make money? Do you need money NOW in order to pay rent at the end of the month? Or would you rather make less money now but more money, in a more scalable way, later?

Let’s walk through a few examples so you understand:

Skills

If you really enjoy working with people, and want to continue building skills where you interact with students or customers live, then you should probably pursue an Offer type that involves those elements:

• Cohort-based Courses

• Paid Communities

• 1:1 Coaching/Consulting

Conversely, if you hate interacting with people and just want to write and create content, maybe you shouldn’t pursue a community-oriented Offer type and pick something more asynchronous:

• Digital products

• Paid newsletters

• Self-publishing

• Software

There is no one right answer. But it would be a mistake to pick an Offer type that involves a handful of skills you don’t have, don’t enjoy, and don’t want to do on a consistent basis—even if that Offer type appears to be more lucrative, or you see someone else’s succeeding with it. And the reason is because if it’s not something you inherently enjoy, care about, and want to get better at, you will give up. You will get bored. You will not have the intrinsic motivation to push through moments of frustration.

So, pick an Offer that aligns with your skills.

Not what you see someone else succeeding with online.

Time Horizon

The second variable is your Time Horizon: how long can you wait to make money?

For example, if you need money NOW, you should start with a service. Why? Because services will always generate the most revenue the fastest. Why do services generate the most revenue the fastest, you ask? Because you don’t need 1,000 customers. You don’t need 100 customers. You don’t even need 10 customers. You need 1 client to pay you $3,000 per month. And that is significantly more achievable in a short amount of time relative to all other business models and Offer types.

The problem with services, however, is while they are quick to generate cash, they are also quick to plateau—and require exponentially harder skill sets in order to scale. It’s fairly common for people to go from $0 to $10,000 per month providing services, but much less common to see people do what’s required to scale from $10,000 per month to $50,000 or $100,000 per month and build a million-dollar business.

Conversely, Offer types like paid newsletters, paid communities, software, anything recurring tends to grow much slower in the beginning. Why? Because the less you charge, the more customers you need. And the way you typically attract these customers is by creating content online—and creating content takes time. So these business models tend to be much slower to start. But the trade-off is once they begin to work and build momentum, they can scale significantly easier than services, or 1:1 coaching and consulting.

So a lot of the decision of which business model and Offer type to choose comes down to what skills you have and want to improve, and the time horizon over which you will measure success.

And the answer to which business model and Offer type is right for you entirely depends on where you’re at on the journey. For example, I’ve reached a point where I don’t need to make money NOW. Grinding out an extra $5,000 doesn’t do anything for me anymore. Which means all of my decisions need to be in service of sacrificing money NOW to build something much more scalable in the future. But 10 years ago, when I was first starting out, that was not the right answer for me at that time. 10 years ago, I wanted money NOW. And I was willing to grind in order to make it happen because $5,000 was a lot of money back then. In fact, that was my entire net worth!

So, let me make this decision easy for you.

If you are brand new to making money online, even though all of these business models and Offer types are available and potentially lucrative, I would encourage you to start with these two:

• Digital Products: A $99 - $350 text & video course teaching people how to solve some sort of problem or achieve some sort of outcome in your niche.

• Services: A $3,000 - $5,000 per month recurring service where you do the work for someone else, most likely a business owner of some kind.

These are the two business models and Offer types most likely to generate money NOW.

More importantly, every other business model is really a more advanced version of one of these two Offer types. So I’d recommend doing the beginner versions first, and then look to add the other more advanced and complex monetization models to your business thereafter.

Step 5: Make your first $1.

Here’s a riddle for you:

If you do not have a product or service for sale, how much money can you make?

The answer is $0.

In order to make your first $1 online, you have to have something for sale. It is impossible to generate revenue if you do not have an Offer. Which means, if you want to make money online, your first measure for success is not to build the “perfect product” or become a world-renowned industry expert so that you can one day launch the most innovative service ever created.

Your first measure for success is to have something for sale.

Then, and only then, are you able to generate any revenue at all.

Perfectionism is the enemy of progress.

Inside our writing programs, I preach this idea of Practicing In Public.

Nothing will teach you more about your own writing than doing it in front of other people. And nothing will teach you more about how to improve your product or service than charging money for it. The faster you put yourself in that position, the faster you will learn, the faster you will improve your product or service, the faster you will make money online.

Unfortunately, a lot of times people postpone building products or providing services because they’re afraid of disappointing customers. They’re worried their product won’t be good enough, or their service won’t help someone. But the truth is, even if that were to happen, disappointment is a positive signal. Now you know what to fix! Now you know what to improve so that it doesn’t happen again.

The first digital product you create is going to be your worst one. The first time you provide a service is going to be the worst version of that service. It’s inevitable. But you cannot get to the second version until you provide that first version. And oftentimes, we are much more critical of ourselves than customers are of us. Looking back, my first digital product was horrible. There were so many skills I didn’t have yet, and so many things I would do very differently today. But customers weren’t nearly as critical. In fact, many of them loved it!

The point is, you can’t learn how to write the perfect piece of content, or build the perfect digital product, or provide the perfect service by thinking about it by yourself.

You can only learn how to improve something once it’s in front of someone else.

Then, improvement becomes obvious.

“But Cole?! Shouldn’t I wait until my audience is bigger before I launch my product or service?”

You can—but my advice would be to have something available for sale sooner rather than later.

For a few reasons:

• First, having a paid Offer elevates your perceived value. When you have a digital product, or say you provide a service for a certain type of person, people assume you are established. Because established people have businesses and make money! So having something for sale actually makes it easier to attract your target readers and potential customers, and further positions you as a leader in your chosen niche.

• Second, as your audience grows, you might as well monetize on the way up. Every writer or creator I know wishes they had started monetizing sooner. The reason is because building an audience online takes a lot of effort. So if you’re going to prioritize that much effort into something, you might as well collect revenue along the way. There’s very little to be gained by delaying monetization. You don’t necessarily “make more money” later as a result.

• Third, this thinking implies customers only buy once. And that’s not true. The longer you write within a niche, and the more products or services you provide within that niche, the more repeat customers you will attract.

So the sooner you monetize, and have something for sale, the sooner you will begin to build your recurring or re-occurring base of customers.

Step 6: Gather testimonials.

The moment someone hands you money, the improvement cycle begins.

Without question, this is the biggest mistake I made with my fitness eBooks way back in 2014. I ended up selling thousands of copies of those eBooks to customers all over the world and didn’t once ask for feedback, launch updated versions, or ask for testimonials to use in future marketing.

If I had, I could have easily turned that fitness eBook series into a 6-figure, maybe even a 7-figure business.

So, let’s make sure you don’t make the same mistake.

Once you have a product or service for sale, here are the highest-leverage things you can do to improve that product or service, and generate more revenue.

Improvement Tip #1: Ask for feedback.

If you sell a digital product, you should email every single person who buys and ask them:

• “How did you find me & my product?” This will tell you which of your marketing efforts are working, and which of your social platforms are bringing you customers.

• “Was there anything missing from the product that would be helpful?” This will give you insight into what could be improved.

And as an incentive, you can give every single customer who gives you feedback free access to any future upgrades you make to your product.

The advanced version of this would be to email every single person who buys your product and ask if they would be open to a 30-minute Zoom interview—and you can give them some sort of bonus or additional asset in exchange. I cannot emphasize how valuable these customer interviews are. Customers will literally tell you the answers.

• They will tell you what was confusing.

• They will tell you what was missing.

• They will tell you what they would have paid more for.

• They will tell you what other questions they still have.

• They will tell you why they bought your product in the first place.

Everyone loves to overcomplicate how to build great digital products or provide valuable services. But the truth is, it’s not complicated at all. It’s just tedious.

Talk to every customer. Record the conversations.

Then go back through each call recording and take their exact words—how they phrased their biggest problem, what they found confusing, etc.—and use their words to improve the product and improve the marketing.

If you want to make more money, talk to more customers.

And if you sell a service, you should ask these same questions to every single one of your prospects and clients:

• “How did you find me & my service?” Again, this will tell you which of your marketing efforts are working, and which of your social platforms are bringing you qualified clients.

• “What’s the biggest problem in your business right now?” This will tell you what they care most about, which should be what you anchor the value of your service to. And this will also tell you what other problems you should potentially charge even more money to help them solve, upselling the client on additional services.

• “Is there anything about my process you find confusing, or would like me to change?” The more you can ask clients directly how they would prefer to receive information, communicate, or work with you, the better you will understand how to help them. You will also spot patterns between clients or client types, making it easier for you to anticipate these preferences with clients in the future.

When you ask people how to improve, or what you could do differently to make them happier, they will always tell you.

But a surefire way to make less money is to not ask at all.

Improvement Tip #2: Launch updated versions.

When customers or clients give you feedback, that feedback usually leads to two types of upgrades:

• Feedback to improve the existing offer. As a general rule of thumb, until your product or service is generating at least a million dollars per year, the answer is not to jump around and launch more products or more services. The right next step is to keep improving the product until it’s good enough to become a 7-figure business. This is what I did with my ghostwriting agency, which I scaled to millions of dollars in revenue. And this is what we did with Ship 30 for 30, which crossed a million dollars in revenue in its first year operating as a cohort-based course.

• Feedback to expand the offer into an upsell. Sometimes, customer interviews reveal other problems you can help them solve—either with information in the form of digital products, or additional services. In this case, it’s actually counter-productive to try to solve more and more and more problems within your original product or service. Trying to solve too many “different” problems ends up making that product or service more confusing—not necessarily more valuable. Instead, you’re better off breaking out these problems and monetizing them as separate products or services, otherwise known as “upsells.”

This is why the hardest part of writing and making money online is “starting.” Because once you start writing, and especially once you launch your first product or service, you very quickly realize how much more you have to write about, and how many more products or services you could provide people to monetize over and over again.

Improvement Tip #3: Gather testimonials.

Lastly, while testimonials or case studies are certainly not required in order to launch your first digital product or service (remember, everyone starts at zero), they are incredible assets to have for all your future marketing.

Your goal, for your first 1,000 customers, is to collect 1,000 testimonials.

You should ask every single person who buys something from you:

• “Would you mind sharing a testimonial?”

• “How did this help you?”

• “What problem did you have, and were you able to fix it?”

• “What outcome were you hoping to achieve, and were you able to achieve it?”

Testimonials themselves are valuable. But in all honesty, what is even more valuable is what each testimonial teaches you about your target customer.

Their words will become your marketing copy.

Their stories will become your transformation thesis.

Their fears will give you ideas of helpful content you can create and share.

Nothing will make you more money than talking to your customers.

I repeat:

Nothing will make you more money than talking to your customers.

Step 7: Monetize in more ways!

Once you’ve started writing on social platforms, once you’ve started moving rented readers over to your owned email list, and once you’ve launched some sort of product or service (and made your first $1 online), there’s only one step left.

Do it again, do it more, and do it in more ways!

Volume wins.

The first big idea I want to share here is that there are two ways to scale a business:

• Traffic: Offer more people the same thing.

• Upsells: Or offer more things to the same people.

The goal is obviously to do both.

Traffic means marketing. Once you have a product or service for sale, how much money you make is directly correlated to how much marketing you do and how much better you do it. So, as a beginner, more marketing first means doing more of it: post more times, across more platforms. And then once you’ve maxed out “more,” do it better. How can you make each post perform 2x better? 5x better? 10x better? If you want more insight into this More/Better/New framework, I recommend reading this piece I wrote on 20 Lessons Selling $20M of Online Writing Courses.

Upsells means helping people solve more problems. If you sell digital products, that means creating other “different” digital products helping people solve other “different” problems. And if you sell services, that means offering other “different” services helping clients solve other “different” problems in their business. This is how you extend LTV: the lifetime value of each customer.

From here, you can then add other offer types to monetize in more ways.

The ultimate goal is to become a Full-Stack Writer.

This won’t happen overnight. In fact, it probably won’t even happen in your first year.

But eventually, where you want to end up is with a business that services different customers, at different price points, with different Offer types.

Take a look at our Digital Writing business vertical, for example:

• The Art & Business of Online Writing: Our most entry-level offer is actually my book. It’s $9 for the eBook or $19 for the print book, and covers all the fundamental principles of writing in the digital age.

• Write With AI: Next is our paid newsletter on Substack. It costs $20 per month, and provides readers with additional digital writing education as well as exclusive AI prompts. This services a diverse range of customers, and is very price-accessible.

• AI Writing Skool: Our next most expensive offer is our paid community on Skool. It costs $99 per month, and includes a lot of the same information we share in our paid newsletter, Write With AI, but also gives students “more”: more AI prompts, more templates, more trainings and mini-courses, and more access to us. Members of AI Writing Skool can come ask questions every Monday, workshop their writing, and jump in the hot seat and get feedback on anything they’d like. They also get free access to our 5-Day writing sprints, and 50%-off any 2-week bootcamps we run.

• Digital Products: Next, we have audience-specific stand-alone digital products people can buy individually, depending on what they’re interested in, what problem they want to solve, or what outcome they’re looking to achieve. These include Category Newsletter Creator, Low-Ticket Launchpad, Substack Starter Kit, Self-Publishing Studio, Decision Journaling, LinkedIn AI, and GhostwriterGPT.

• Ship 30 for 30: Lastly, we have our cohort-based writing program. It’s a 30-day writing challenge, and for that month is significantly more hands-on than any of our other offers. Which is why it’s also more expensive.

Each of these Offer types serves a slightly different type of customer, at a different price point, all focused on digital writing education and writing with AI.

And the more ways you monetize, the more “different” types of customers you can help, the more you will extend the average lifetime value of each customer, the more you can reinvest in the creation of new products & services.

Which is how you make money in a niche forever.

—Cole

Founder of Different Publishing (you can find my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Ship 30 For 30

Co-Founder of Premium Ghostwriting Academy

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Dear Writer,

In 2026, there are 5 text-based formats you need to know how to write, if:

• You want to build an audience

• You want to become known for a niche you own

• You want to get leverage out of your library

• You want to pull short-form out of long-form, and expand long-form out of short-form

• And most of all, you want to make money online from your content directly—or use your content to drive customers to your business.

Because if you can write online using these 5 types of formats, you can write anything.

You can write & self-publish books.

You can build a category-defining free or paid newsletter.

You can turn proven short-form content into viral long-form content.

You can expand long-form content into digital products, cohort-based curriculums, even coaching and consulting frameworks.

These 5 formats are the foundational pieces of everything else you could ever want to write and create.

But before we talk about the 5 formats, we need to back-up one step.

Where should you be writing online in 2026?

Back in 2010, the answer was to start a blog.

Then, in 2014, the answer was Facebook and Quora.

Then, in 2016, the answer was Quora and Medium.

Then, in 2018, the answer was Medium and LinkedIn.

Then, in 2020, the answer was Twitter (now known as X).

Then, in 2023, the answer was X and LinkedIn.

My point is, every two or three years, “where” you should be writing online changes. This is because new social platforms emerge, old social platforms degrade or even die, and algorithms continue to change and prioritize new content formats and, sometimes, suddenly punish other content formats.

So the name of the game isn’t really learning how to write and “growth hack” one platform and then never have to adapt ever again.

No, the name of the game is to understand that the game is always changing, and build the skills that allow you to change with it.

This is why my entire point of view for writing online is based on this idea that your Library is more valuable than Virality.

The performance of any individual piece, on any one platform, doesn’t matter.

Going viral is cool for like two days. It’s a dopamine rush. But then, 48 hours later, your reach reverts back to your previous baseline and you go right back to doing exactly what you were doing before—which is just consistently playing the lottery game that is writing online.

I call it a Lottery Game because you don’t have control over when you win the lottery.

In fact, more often than not:

• The pieces you work really hard on, and think are going to go viral and get a ton of positive feedback, end up flopping.

• And the pieces you write really quickly, and debate even publishing at all (because you don’t think it’s any good), end up going viral.

I just had this happen.

I spent 20 hours writing this long-form piece on 20 Lessons Learned Selling $20,000,000 of Online Writing Courses.

These are very expensive lessons I’ve had to learn building our portfolio of writing businesses. And it took a lot of time for me to write and crystallize all these lessons into a 10,000-word essay and newsletter.

I was sure it was going to go niche-viral in our little corner of the Internet.

And then I posted it, and it completely flopped. In fact, it’s one of my lowest-performing pieces ever.

So, this is not something you only experience as a beginner. I’ve been writing online for more than 15 years and I still experience this on a daily basis.

Writing online is a lottery game. You won’t know what’s going to work.

Which means the only thing you have control over is 3 things:

• Where you write

• What you write

• And how many days, weeks, months, and years you write for

So, let’s start at the beginning:

The 3 best platforms for text-based content in 2026 are:

• X

• LinkedIn

• Substack

And here’s why.

X has over 500 million users. It also is the platform with the highest-capacity to go viral—meaning as far as text-based content goes, it is where you are most likely to hit a home run and reach millions of readers. It also has the most flexibility in terms of the types of content you can publish: you can write stand-alone short-form tweets, you can connect tweets into threads, you can post medium-length essays into expanded posts, you can write full-blown articles and embed images. You can do a lot on X today that you couldn’t do on Twitter 5 or 10 years ago. Which is why we recommend every single writer start on X first.

LinkedIn has over 1 billion users. Think about that. It’s a gigantic platform. But LinkedIn also has all kinds of benefits for writers. First of all, it’s primarily a text-based platform. Yes, people post images and videos, but text is by far its most common content type. Second, LinkedIn as a platform has the largest number of affluent users. So especially if you’re writing and creating content in an industry where your goal is to attract qualified readers and prospects, LinkedIn is your best bet. Third, LinkedIn has a severe mismatch between creators and consumers. Most writers think LinkedIn is just a job-searching platform. But remember… it has over a billion users! So just by writing and creating content on LinkedIn instantly puts you in the top 1% of writers on the platform.

Substack has raised $100M in venture funding and is growing fast. Lastly, Substack has a lot of potential and for the past few years we’ve been making a big bet by publishing a lot of content on the platform. Because, as a general rule of thumb, just follow the money. Substack has raised over $100M from some of the most well-known venture capital firms in Silicon Valley, and have been very effective at convincing legacy journalists to leave major publications like The New York Times and start their own newsletters on Substack instead. Substack also has two different components to their platform: they have the newsletter-publishing side, and then Substack Notes which is the social content side. When you publish newsletters on Substack, you get to tap into Substack’s social feed and distribution.

This is a huge benefit.

Just look at our Substack paid newsletter, Write With AI, for example:

Yes, we drive external traffic to this newsletter. But more than 55% of all our email list subscribers have come from inside the platform’s recommendation engine.

That’s a lot of free growth!

So, you see, choosing WHERE to write online is half the game.

You always want to be writing in the digital environments most likely to give you distribution.

And the best platforms today will not be the best platforms tomorrow.

Which is why, what matters more than anything else, is that you are building a valuable library of content, in a niche, over a prolonged period of time. That way, whenever a new platform emerges, or an old platform dies, your library retains its value. And all you have to do is copy/paste your entire niche library over to the next platform—and capitalize on the next new arbitrage opportunity.

So now you know where to write.

Next, let’s talk about WHAT to write.

The 5 Best Writing Formats In 2026

Since the social platforms that provide the best distribution for text-based content are always changing, that also means the “formats” that perform best on each platform are also always changing.

For example, back in 2021, the best writing format and the one that provided the most free distribution was Twitter Threads.

These were strings of stand-alone tweets connected into a Thread—with the first Tweet being some sort of “hook” that got readers to click into and scroll through the entire Thread.

Back in 2021, if you were even halfway competent at writing Threads, you were able to get exponentially more reach and engagement on your writing than if you were to post the same exact content on any other social platform. This is what I mean when I say, every few years, the best platforms change, but so do the best formats on each platform. And if you can learn how to spot these trends, you can capitalize on them. For example, writing Twitter Threads is how we built our writing program, Ship 30 for 30, to millions of dollars in revenue in its first year.

All me and my business partner, Dickie Bush, did was write threads on writing-related topics…

At the end of the thread, link to our Start Writing Online free 5-day email course…

And then pitch subscribers on our email list on the next cohort of Ship 30 for 30.

So, what are the best formats right now on X, LinkedIn, and Substack?

Let’s walk through each one.

Format #1: Tweets

Tweets are short-form text-based posts, basically bite-sized thoughts compressed into 280 characters or less.

I find writers and creators struggle with this format more than any other format on the Internet. That’s because, as 17th-century French mathematician and philosopher Blaise Pascal put it so eloquently, “If I had more time, I would have written a shorter letter.” Writing something short that is clear and memorable is very hard.

It’s a skill.

But these short-form text posts (or “tweets” as they were known back in my day), are really the foundation of all great writing.

• A single-sentence tweet is the same thing as a great first sentence in a longer piece.

• A two-sentence tweet is the same thing as a hook—either in text, or in a TikTok.

• A succinct paragraph tweet is the same thing as a paragraph in a longer-form essay.

On top of that, short-form written content is really a game of rhetoric.

The best book I’ve ever read on the subject of rhetoric, and how this can apply to short-form content on the Internet, is The Elements of Eloquence by Mark Forsyth.

In the book, he lists out timeless writing mechanisms for making single phrases striking and memorable just by altering their wording. For example, there’s a reason why people remember this iconic phrase from John F. Kennedy’s inaugural address in 1961: “Ask not what your country can do for you—ask what you can do for your country.”

That’s a great line.

But it’s memorable because it uses an age-old rhetoric mechanism called an antimetabole—repeating the same words in reverse grammatical order.

Another more modern example would be entrepreneur, Alex Hormozi, who is known for his short-form content on X.

But if you look closely, the vast majority of his tweets are packaged using these timeless rhetoric principles.

For example, this one where he says, “The goal of youth is optionality. The goal of adulthood is commitment.”

There are two different rhetoric mechanisms working here.

• The primary one is what’s called an Antithesis. This is an obvious observation (the goal of youth is optionality), followed by a non-obvious observation (the goal of adulthood is commitment).

• And the secondary mechanism is what’s called Parallelism. This is where two sentences use identical grammatical structures, “mirroring” each other.

And there are dozens and dozens of these different types of rhetoric mechanisms you can use to make your short-form content sharper, clearer, and much more memorable.

Format #2: Atomic Essays

Atomic Essays are 300-word visual essays to master the fundamentals of writing online.

The Atomic Essay format is actually a format we invented for our beginner writing program, Ship 30 for 30. And the reason we encourage writers to practice with it, especially if they’re brand new to writing online, is because an Atomic Essay is small enough that you can write in 30 minutes or less, but long enough that you can begin to practice the 5 fundamental skills of writing anything in the digital age:

1. Headlines: What are you promising to give the reader if they click and give you their attention?

2. Hooks: How do you hook the reader’s attention in the very first sentence?

3. Formatting: How do you organize your main points into clear sections using headers?

4. Writing Rhythms: How do you alternate sentence and paragraph lengths to make your writing more dynamic and easy to read?

5. Bulleted Lists:

As soon as you have these 5 foundational skills, you will notice yourself using them everywhere—from text and Slack messages to emails and even presentation decks.

And the Atomic Essay format is the easiest, smallest container to practice all of these skills simultaneously.

Format #3: LinkedIn Carousels

LinkedIn Carousels are multimedia slideshows that grab readers’ attention and have the highest likelihood of going viral on LinkedIn.

Carousels have been the best-performing format on LinkedIn since 2024. And no matter how many other formats we test, we find ourselves always coming back to Carousels.

However, writing and building a viral-worthy Carousel in your niche is very different from simply writing a text-based post.

Because Carousels combine multiple forms of media.

First of all, Carousels are visual-first. This means you have to navigate different word-count constraints relative to other social platforms and content formats. Each slide can only hold so many words. Which means each idea needs to be compressed into its smallest, most actionable form.

Second, Carousels lend themselves better to certain topics. Since Carousels are multimedia slideshows, prompting readers to click through slide-by-slide, the vast majority of Carousels that perform well (and go viral) do not cover nuanced topics, require a lot of explanation, or tell longwinded stories. The best Carousels are almost always listicles, sharing “10 tips” or “9 mistakes” or “8 reasons” or “7 prompts.” So choosing the right ideas to turn into LinkedIn Carousels is half the battle.

Third, Carousels involve more skills than just writing. AI has certainly made this easier, but you are still the one responsible for the most important variable, which is your taste. You have to be the one to use AI to design a brand kit you like. You have to choose the images. You have to assemble the content in a way that is visually pleasing to the reader.

And if this sounds like a lot of work, just remember: the skills are the moat.

The reason Carousels perform so well on LinkedIn is because the vast majority of people don’t know how to create Carousels, and aren’t willing to spend a few hours learning how.

But their loss is your gain!

If you can learn how to create this content format, you will immediately elevate the perceived value of your content on LinkedIn.

And don’t worry, you can build this skill in stages.

• If you want a beginner-friendly option to get started, you can create lightweight, text-only Carousels using Typeshare.

• If you want something slightly more advanced, you can create more branded-looking Carousels using Gamma.

• And if you want something pro-grade, you can design your own brand kit and design studio inside Claude Design or ChatGPT.

Lastly, you can squeeze even more juice out of your Carousel Library by republishing them on other platforms.

LinkedIn Carousels can easily be turned into Instagram Carousels and graphics.

LinkedIn Carousels can also be republished on visual platforms like Pinterest.

There are dozens of different ways you can reuse this content. So don’t think of Carousels as LinkedIn-specific. Instead, think of Carousels as a content format—and you can reuse and republish that content format across any other social platforms that allow you to publish something visual (which is essentially all of them).

Format #4: X Articles

X Articles are 800+ word, thought leadership-style, blog posts.

Once you’ve learned the fundamentals of writing online, your library of articles is where you will begin to build the most leverage. This is because articles are a writing format that can be reused, republished, expanded or compressed in infinite ways.

• Articles can be spliced apart, creating dozens of short-form posts.

• Articles can be copy/paste republished across multiple platforms.

• Articles can be sent to your email list as newsletters.

• Articles can be expanded into book chapters.

• Articles can be read aloud as YouTube videos.

• Pieces of articles can be read as Instagram Reels, TikToks, or YouTube Shorts.

The list goes on and on.

Unfortunately, a lot of writers and creators don’t know you can do this.

Either they never realized they could take the same content and copy/paste it to a second, third, or fourth platform… or they thought, if they did, they would get in trouble.

And that’s not true.

This is why my entire thesis for writing on the Internet is about building your library, building your library, building your library. Because it’s yours. You own it. Which means you can republish it wherever you want. You can cut it apart. You can smash it together. You can take a paragraph from one article and a different paragraph from another article and create something new. You can turn free content into paid content, and splice paid content into free content.

This is what writing online is all about.

So the bigger your library of articles grows, the more content you will have to play with—making it easier and easier to write new things using ideas and stories and frameworks you’ve already written down before.

This is leverage.

AI Prompts are prompts you write for yourself, but can also be used as assets all along your content supply chain system, marketing, and as digital products in your business.

We’re still very early in the age of AI. But already, it’s clear that most people only think about how to use AI themselves—failing to realize that every single thing you use AI to do effectively for yourself, simultaneously creates an asset or a product you could give away (or even sell) to your readers and target customers.

So, every time you use AI, you have to remember you’re tapping into 3 forms of leverage.

First, personal leverage.

As I like to say often inside our AI Writing Skool, “You can’t automate what you can’t articulate.”

So first, you have to learn how to do something. You have to acquire a skill.

But then as soon as you have that skill, now in the age of AI the very next thing you should do is get some leverage on that skill. You should train AI on some component of that task, or set of tasks. Now, AI doesn’t have to be able to do all of it, 100%, end-to-end. But if it can help you do a singular piece of that task, except 10x faster, that’s leverage! And the more areas of your life and business you can make those upgrades, build those systems, and get leverage, the better.

But writing a prompt, or using AI to get leverage on a task for yourself is only the beginning.

Second, marketing leverage.

The single most valuable type of marketing, ever, is where you give your target customers something for FREE that saves them time or helps make them money.

Which means, every time you write a prompt for yourself, you aren’t just automating yourself or your own work. What you’re also doing is creating an incredibly compelling and valuable marketing asset—an incentive for your target customers to take some kind of action.

For example, you can say, “I built this prompt for myself. It now saves me 5 hours per week. I want you to have it for free. All you have to do is give me your email.”

There is no better marketing than that.

And I believe the masses still haven’t realized this opportunity exists inside every single niche on planet earth. Everyone is asking themselves how they can use AI in their life and their business right now. Which means, no matter what your niche is, you have the opportunity to help give people the same prompts and systems you’re building for yourself.

Third, business leverage.

The same way your library of content can be compressed or expanded, free content can become paid content and paid content can be spliced apart into free content… the same is true with AI prompts, Claude .Skills, and other technology assets.

Every time you create a prompt, or build a system for yourself, what you’re really doing is creating an asset—a product. And you can do all sorts of things with these products.

• You can give them away for free as incentives in your marketing.

• Or, you can sell them as stand-alone digital products.

• Or, you can combine them into a more expensive prompt pack.

• Or, you can combine them into a prompt pack and give it away for free as a bonus inside one of your other products, platforms, or services.

• Or, you can make them monthly unlocks as part of your paid community as a retention bonus.

• Or, you can make them downsells for when someone doesn’t purchase your more expensive product or service.

The list goes on and on.

My point is, anytime you build something for yourself, you have to recognize that you can “sell your sawdust.”

And in the age of AI, prompts are products.

—Cole

Founder of Different Publishing (you can find all my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

Co-Creator of AI Cole

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Dear Writer,

Earlier this year, we crossed $20,000,000 in lifetime sales as a writing education business.

This is the aggregate amount generated from the following verticals:

• Ship 30 for 30: The largest cohort-based beginner writing program on the Internet.

• Premium Ghostwriting Academy: The leading training program for freelancers to become premium ghostwriters.

• Write With AI: The #2 education paid newsletter on Substack, on how to use AI as a writer/creator.

• Digital Writing Skool: How to make your first $1 online building/selling digital education products. (This includes all of our one-off digital product drops as well.)

About a year and a half ago, I wrote a similar reflection piece on 10 lessons learned selling $10,000,000 worth of digital education products.

But a lot has changed since then.

• Our portfolio of writing education businesses grew from 10 full-time team members to more than 30 full-time team members.

• Our yearly revenue went from $6M to $8M, spread across these different verticals.

• Our operational complexity, especially running our Premium Ghostwriting Academy, is 5-10x what it was a year ago.

• And we transitioned from being 100% dependent upon organic traffic to adding in paid ads. Over the past year, we have spent upwards of $1,000,000+ on paid ads.

So I thought it would be helpful to take a breath here at this $20M Lifetime Revenue Milestone and share some of our biggest learnings.

If you run, or have any interest in building a digital education business, I hope this helps you on your own journey.

And if you want help scaling your own education business, I’d love to work with you inside our AI Writing Skool!

Lesson #1: Subjectivity doesn’t scale.

Anytime someone says to me, “I want to scale my business,” the first thing I try to identify is what about their business is currently subjective.

Oftentimes, subjectivity hides in plain sight.

An example would be: 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 Manager’s role hasn’t yet been defined.

• They “do what they do” intuitively—not based on a prescriptive checklist or set of processes. And if you don’t have these clearly defined processes, then you can’t scale this person’s role.

• They 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 actions that can be replicated, you can’t scale this person’s personality.

• **And they solve problems based on their own level of personal motivation—**maybe they are proactive because that’s a quality 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 scale this person’s level of motivation.

On the surface, a great hire masks a lot of these problems.

And it’s not until you start unbundling their role, their motivations & reward system, and even their personality that you begin to realize the level of specificity you need to achieve in order to successfully scale someone’s role within a company.

Subjectivity doesn’t scale.

Lesson #2: If traffic is concentrated, scale vertically. If traffic is decentralized, scale horizontally.

The amount of things you can sell your audience is dependent upon whether the traffic you generate is concentrated or decentralized.

• Concentrated traffic means: one personal brand building one email list.

• Decentralized traffic means: multiple personal brands building multiple different email lists.

For example, in early 2026 we thought we could scale the business even further horizontally by promoting a few people within our company to lead programs of their own. “More offers = more money,” we thought.

The problem is, these team members didn’t have audiences of their own.

Traffic was not decentralized. It was concentrated. Which meant their offers were dependent upon our audiences—which ended up competing with our own offers.

We learned (the hard way) that if traffic is concentrated to a single personal brand (or in my & Dickie’s case, two personal brands) 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, cannibalizing your core business.

This is different than what a company like Agora Financial has been able to achieve. Their education business and the traffic they generate is not concentrated to one personal brand. Their traffic is decentralized, each personal brand and “thought leader” having their own audience, and their own credibility, which they can monetize with their own stack of offers.

If we were to try to scale horizontally again, what I would do is look to partner with tangentially-related creators who have built their own audiences in “similar but different” niches—and then help them on the back-end with operations, offer construction, and LTV extension.

Lesson #3: It takes 20 live webinars to figure out how to make a webinar ROI positive.

In 2025, we decided we wanted to try to scale PGA with paid ads and live webinars.

• The first webinar was just a forcing function for us to get a rep in. The measure for success was, quite literally, to just “do it once.”

• The second webinar was a container to fix everything that broke during the first webinar.

• And the third webinar was the first rep where we knew enough that we could begin to iterate and improve.

But it took upwards of 20 weekly webinars to get it right.

Each webinar was 2+ hours. The same slides. Sharing the same stories and insights. Answering the same questions. Giving the same pitch. And still, 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.

I share that because if you’re thinking about scaling with paid ads and/or webinars, I want to level-set your expectations.

Before we held that first webinar, I thought, “Great, we’ll do this once or twice and then it’ll just be on repeat.” That is not what happened. And I feel stupid for ever thinking that’s 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!

(That said, if you’re willing to put in the work, webinars can perform very well. And now, we view them as one of the highest-ROI vehicles for acquiring new customers into our ecosystem of writing programs.)

Lesson #4: 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. “More money” doesn’t make those problems go away. In fact, it’s quite the opposite. More money just increases the likelihood you will spend money on the wrong things.

• Some of the worst hires I’ve made happened during periods where our business was generating the most revenue.

• And some of the best hires I’ve made happened during periods where our business was very small and very lean.

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 growing fast. It’s so much easier (especially when you’re stressed) to just say, “Eh, whatever, let’s hire someone for that.”

But remove the excess cash-flow and ask yourself the same question (”Would I hire this person?”) and all of a sudden you realize… no way!

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 a small, lean, cash-conscious company.

(*The nuance here is: yes, oftentimes you have to spend money to make money, or invest in talent proactively in order to grow to the next level. I’m not advocating for frugality. I’m reminding myself, in writing 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 #5: Limit salespeople’s commissions to their current employment.

This is a pretty specific lesson that only applies if you run a high-ticket group coaching program, agency, or B2B business, but it was a painful one for us.

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. This passes the risk along to the business instead of the individual.

Here’s how it works:

• A typical draw might be $3k-$5k per month. Think of this as their “salary.”

• The salesperson gets this draw (say $3k/mo) no matter what. This protects their downside.

• But they do not unlock their upside until they generate $3k in commissions for themselves. This makes their draw similar to an “advance.”

For high-performers, the draw doesn’t matter because they’re going to recoup and exceed their draw every month.

And for low-performers, the draw gives them some “runway” to figure things out. But if 2-3 months goes by and they aren’t able to out-earn their draw, the answer is pretty clear they aren’t a good fit.

The reason you have a draw is primarily for the first 1-3 months of onboarding a new sales rep.

I digress.

The LESSON, though, 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.

This prevents a few things:

• It simplifies accounting. You don’t want to be continuing to track monthly payouts for people you no longer even employ.

• It prevents salespeople “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. (This is rare, but worth planning for these types of outlier situations.)

• It acts as a retention mechanism. Selling customers on recurring contractors or payment plans is a bit like a salesperson building up their own “book of business” and recurring revenue. And eventually, there is no incentive for them to stay if they can just take all that revenue with them. 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.

Whoops.

Lesson #6: You can do “More” way, way longer than you think.

One of my favorite Hormozi frameworks is More, Better, New:

• First, do More

• Then, do it Better

• Then, and only then, consider something New

Unfortunately, I have continued to learn the hard lesson that you can do “more” way, way longer than you think.

Let me walk through this slowly.

Whenever you reach any sort of ceiling or plateau, it’s very easy to believe you have “maxed out” your opportunity vehicle. You think there’s no way you can do “More.” But the truth is, you think you’ve plateaued because you haven’t yet been exposed to the next level of “More.” It’s the equivalent of being a middle school basketball player and thinking, “There’s no way I could work harder!” But then one day you go train with the high-school kids and you realize, hang on a second, there’s a completely different level of effort that is available to me.

We experienced this when we joined Alex Hormozi’s ACQ Workshop.

• You think you’re running “so many ads” until you sit in a room and hear someone explain how they’re running 100x 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 10x more people, 10x faster than you.

• You think you have “such high standards” until you sit in a room and hear someone explain their standards, and you realize their standards are way higher than yours.

• You think you’re working “so hard” until you sit in a room and hear someone explain their day starts earlier than yours and ends later than yours.

• Etc.

The point is, anytime you feel you’ve reached a “More” plateau, the answer is not actually to jump to something “Better” or “New.”

The first answer is to find environments that challenge your definition of “More.”

Because, chances are, however you’re defining the “max” of whatever thing you’re doing, is wrong.

Lesson #7: When you reach a “Better” plateau, the impulse is to pick something “New” (which is a mistake).

Building on the above…

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. Doing something “Better” is not usually some giant action, decision, or change. “Better” is more likely to be 1,000 tiny upgrades, made one at a time, none of which in the moment lead to an exponential outcome, but all of them added together over a prolonged period of time do. (As Hormozi puts it: “1,000 golden BBs, not 1 silver bullet.”)

Which means “Better” requires a lot of patience and consistency—two things humans are historically very bad at.

As a result, as soon as you begin down the “Better” path, you are quickly confronted by a handful of painful realities:

• “This is boring!”

• “This is tedious!”

• “This is monotonous!”

• “This is going to take forever!”

Which is what causes so many people (myself included) to come to the faulty conclusion that they should do something else.

They should start something “New!”

Which is almost always the mistake.

The reason I say it’s a mistake (and I continue to learn this hard lesson myself) is because people stop pursuing the “Better” path for two reasons:

• They get bored, frustrated, or lose interest

• Or they don’t know how to do “Better” any more

But when this happens, and you decide the right decision is to start something “New,” you actually create two different problems for yourself at the same time.

First, you start over. You’re solving for “boredom” with novelty—which feels great in the short-term, but very quickly loops you back to where you already were before.

Second, you deprive yourself of learning the “Even Better” way to do what you were doing before. The higher you climb, the “Better” you get at something, the more nuanced the next improvement. And sometimes, you need to spend 2-3 months consuming lots of different information to learn how to do what you’re already doing, “Better.”

The problem, though, is once you start something “New,” now you have a new commitment.

So, a few months later, when you finally realize how to do the thing you were doing before, “Better,” you can’t do it. You don’t have the time or the bandwidth—because you’ve already started prioritizing something else, something “New.”

Which is why I’ve set a new little rule for myself.

Anytime I reach a “Better” plateau, I will not start something “New” unless I have given myself at least 3 months of trying as hard as I possibly can 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 time 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” 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 #8: 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 YouTube Organic

• You could build an entire business just on 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 is literally endless.

But something 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’s very easy to see someone else succeeding online running a completely different “marketing playbook” as you and thinking, “I should do that! I bet their model is so much better! I bet they don’t have any of the problems I have.” But that’s not true.

As a mentor used to say to me all the time: “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 annoying.”

Which means the game isn’t to bounce around and try every new playbook-of-the-month.

Just commit to a platform and/or style of marketing, and use it to build a great business for yourself.

You don’t need to do “everything.”

Lesson #9: 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

• Pro-grade at-home setup

• Teleprompter, fancy camera

• Script writer, thumbnail designer

• Etc.

The reality, though, is none of these things matter if a) the content isn’t helpful (or entertaining, depending on your niche) and b) you’re awkward on camera.

I have now published over 1,400 videos on my YouTube channel.

And I can tell you that many of my highest-performing videos have the lowest production quality.

For example, earlier this year we doubled our entire video production team and started investing heavily into YouTube.

• We had a Head of Video Content

• We had a Lead Editor

• We had a Thumbnail Designer

• We had multiple Shorts Editors

And once a month, we’d spend $5,000+ renting a huge Airbnb property for a day to film a month’s worth of content—8 hours straight.

All together, our monthly video production team costs were in the ballpark of $50,000/mo.

And the videos looked great. We captured a lot of epic-looking content.

But then I recorded a Loom video one afternoon and published it to my YouTube channel myself. And that Loom video outperformed almost every high-production video we had filmed, edited, and published over the prior 3 months.

Which suddenly raises the question, “What am I spending $50,000 a month for?”

*Now, obviously there is an intangible cost to building a brand. And we could make the argument that high production quality content builds a stronger relationship with customers and up-levels the perceived value of the brand, blah blah. But the point is still the same.

So whenever someone asks me how they can get started on YouTube, or which camera they should buy, etc., the first thing I tell them is to not buy anything and just record 100 Loom videos of you talking over a Google or Notion doc.

Because, in the beginning, you need to build a few skills:

• You need to “do it” consistently—and prove (to yourself) YouTube is a priority.

• You need to clarify your thinking for video—and that can be done with a Google doc.

• And you need to practice speaking on camera—which does not require “a professional camera.”

There is, quite 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 yet.

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 lesson applies to everything.

Lesson #10: 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 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 have been building education products and programs for 6 years now.

And after teaching tens of thousands of students about how to write in the digital age, I’ve accumulated a tremendous amount of pattern recognition around which actions lead to results and which actions lead to overthinking, procrastination, and lack of progress.

Whenever I think about the AI era we’re in, and where AI is headed, I always come back to things I’ve observed within our writing programs.

• Most people want the shortcut—but the shortcut is always the longer road in disguise.

• Most people want to believe 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.

• 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, and everything to do with their own lack of clarity.

All of these things are starting to create a pattern 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, an insight, a story, 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.

For example, back in 2021/2022, Twitter’s algorithm prioritized Threads—long listicles consisting of 10 or 20 Tweets strung together. If you saw this trend, and 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 7-figure writing program in its first year.

All we did was write 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.

By 2023, after Elon bought Twitter and renamed it to X, Threads basically went extinct.

But I have been writing online since 2007. I have seen dozens of these little marketing cycles where a tactic absolutely crushes for 12-24 months and then completely disappears. So by the time the Twitter algorithm changed, we were already onto the next platform. In 2023, we started re-publishing our most proven ideas and content on LinkedIn in the form of Carousels (the next “viral-worthy format”) and LinkedIn quickly started outperforming X in terms of lead generation—even though our X audiences were 3-5x bigger.

The point is, whenever you find a marketing tactic that works, don’t take it for granted.

Recognize that you’ve just stumbled upon an arbitrage opportunity. And you should do as much of that marketing mechanism as possible, as fast as possible, because it’s 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 is Viral Drops.

We have been running these on X, LinkedIn, and Substack for the past year, sometimes multiple times per 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 & engaging with the post.

The reason this works so well is because it creates a flywheel:

• You can only get the asset if you comment & engage

• As more people comment & engage, the algorithm sees that engagement and shows the post to more people

• As more people see it, more people comment & engage

• Etc.

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.

(*That said, a lot of people are hip to this tactic now, and we’re already seeing diminishing returns with it now a year later. So, when you see a tactic working, exploit it—but keep your eyes out for the next arbitrage opportunity, because this one won’t last forever.)

Lesson #12: The best managers are Intrapreneurs—and incentivized accordingly.

You enter the “Valley of Death” as soon as your company crosses about 15 employees.

The reason is because, as a solo founder or 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.

But the problem with managers, or department heads, is they are typically pure costs. Their job isn’t really revenue-critical. It’s more organizational, making sure the business continues operating at a certain standard and doesn’t break. They are also expensive hires, because in order to be a manager you need to have enough working knowledge to manage the people “doing the doing.”

And all of these costs fall directly to the bottom line.

The business goes through this “Valley of Death” period where in order to grow further (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’s 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 you’ve just opened within your business.

This is why you hear entrepreneurs talk about how their business at ~10 team members was more profitable than their business at ~30 team members. Because as soon as you enter the “Valley of Death,” there’s no middle ground. You either expand the capacity of the business and successfully grow through it, or you don’t. And if you don’t, then it doesn’t make sense to have an entire layer of management.

All of these problems are compounded when your managers are not Intrapreneurs.

Over the years, I have learned there are 2 types of managers:

• Blockers

• Builders

“Blockers” are managers whose value is protecting the team, the team’s time, and making sure what needs to get done gets done. They’re fantastic at keeping an existing machine operating. Blockers tend to be better for departments that have already been built, don’t change much, and just need structure and accountability.

“Builders” are managers whose value is building a department from scratch, or scaling a department from its current stage to an entirely new level. Builder-managers are typically more entrepreneurial, and have already built the thing you need them to build somewhere else. 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 doing so successfully.

Generally speaking, once your company crosses ~15 full-time employees and you enter the “Valley of Death,” it’s 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 your company’s biggest bottleneck.

A company can only successfully scale through the “Valley of Death” when each department has a Builder at the helm capable of growing it to the next level.

Lesson #13: Whatever gets your attention, grows. 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 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 one. And even then, the person has to have “Founder Potential.” It’s 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 zero involvement from you. If that’s the case, and you have the resources to make that bet on someone else, then yes, it’s possible to grow something in parallel. But the vast majority of the time, people rush this decision, and don’t realize they are still the primary operator.

Which means, in any given season of life & 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 = more effort = 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 is 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 but starts to slowly decline.

• Whenever we pick a new product or offer to focus on and prioritize, our other offers begin to go down in revenue.

• Whenever we pick a new department to focus on and prioritize, our other departments’ standard begins to dip, more things slip through the cracks, and performance begins to go down.

There is no avoiding this problem.

Which is why business is a game of choosing which 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 #14: Customers don’t want more information. They want better results, faster, with less work.

This is one of those things that sounds so simple, but in practice is incredibly hard to execute and keep top of mind.

When you’re selling any kind of “info” product, cohort, or 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 takeaways. 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 want to know how the sausage gets made—they just want the sausage. And they want it now. With minimal effort.

If that sounds hard to deliver, that’s because it is.

Customers value less information but faster, more guaranteed results MORE than they do “lots of information” but slower, more ambiguous results.

This means you have to spend more time thinking about what to remove rather than what to add.

• Do customers really need 10 modules? How can you give them what they need in 3?

• Do customers really need 8 live sessions? How could you accomplish all of this in a single hour?

• Do customers really need to know “all this stuff?” How can you just give them a checklist 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.

*(This is fundamentally why you see so many people selling AI Prompts and Claude Skills now. Because you’re not selling “information.” What you’re selling is: “Copy/paste this thing to get the same result I get in 30 seconds with 0 work.”)

Lesson #15: Don’t anchor your business’s 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.

• When I was making $10k per month in personal income, I thought $20k/mo was life-changing money.

• When I was making $20k per month, I thought $40k/mo was life-changing money.

• When I was making $40k per month, I thought $80k/mo was life-changing money.

• When I was making $80k per month, I thought $160k/mo was life-changing money.

The goal post never stops moving.

The problem is, if you anchor yourself to your business’s “highest-performing month,” then you will begin to make decisions in your life assuming that peak won’t go away.

And if I’ve learned anything in business, it’s 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 Rollercoaster.

So, don’t make forward-leaning decisions based on your “peak month.”

Instead, make decisions based on a rolling 12-month average.

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 quarter.

Lesson #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’ve experienced to-date.

And yes, part of that 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. (Looking back, I can say now 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 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. My primary motivator for building PGA was not “to make more money,” and I think to scale any business to a meaningful level (meaning high 7-figures or 8-figures and above), money can’t be the only motivator.

Because it’s too hard.

Over the past 3 years, I have experienced a tremendous amount of responsibility and stress.

I’m already a millionaire. So incrementally “more money” is no longer motivating for me.

What IS motivating is knowing I’m growing. Even if it’s painful.

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, then you are much better off not scaling your business. Because oftentimes, scaling your business does not mean you make more money—and certainly not “right away.” Scaling often means sacrifice, and making less money in the short term, in hopes of making more money later.

So if your only motivation is “making more money now,” then don’t scale. Just stay small. Stack profit. Buy some Bitcoin if you want to add a flavor of risk (not financial advice). And enjoy the fact that you operate a small business and cash-flowing machine that pays for your life and then some.

Only scale if your motivation to grow is more than just money.

Lesson #17: Info + Software + Coaching = 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 clear: we did not do this intentionally. We didn’t really understand what we were doing at the time. This was done intuitively, and just happened to be the right answer. I can only see the framework now in hindsight.

• **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, etc., but people were mostly buying “how to write online” education paired with this accountability.)

• **Typeshare was the SaaS platform we built (with Sam Shore) to pair with it.** Inside Ship 30 for 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 for 30, we launched a back-end upsell called Captain’s Table. This was like a lightweight community/mastermind for Ship 30 graduates who wanted access to “more education” and “more live sessions with us.”

All of these things together created a pretty amazing flywheel:

Ship 30 for 30 was a profitable business in itself.

But Ship 30 also meant we profitably acquired Typeshare customers.

Typeshare customers became a secondary source of recurring revenue.

And Ship 30/Typeshare customers both became the people most likely to join Captain’s Table.

Whenever I’m building info products/programs now, I think about how to replicate this stack of offers.

A few years later, we did this within our Premium Ghostwriting Academy too.

• PGA was a high-ticket group coaching program. 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 Ghostbase. This was the “software” component.

• And then we would upsell PGA students & Ghostbase users to our back-end program, Liftoff. This was the “continued coaching” component.

In an age where you can vibe-code custom software, you should think of software as a highly congruent & niched-down product 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 #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.

The last quarter of the year was insane:

• In September, we did $901,508 in revenue—and ran our first Ship 30 for 30 cohort in over a year.

• In October, we did $710,756 in revenue—and continued running weekly 2 1/2-hour free webinars to drive leads to PGA.

• In November, we did $856,363 in revenue—and ran a huge 3-day ghostwriting challenge, while simultaneously building our Black Friday product.

• And in December, we did $817,107 in revenue—while still running weekly webinars, expanding the video production team, and recording 1-2 months worth of content.

September to December, 2025, is one of the most taxing stretches I’ve ever put myself through as an entrepreneur. The business also did the most revenue it had ever done in 4 consecutive months, so good example of how results tend to follow extreme effort.

But even 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 of the year and decide to coast into Christmas.

I did the opposite.

After that entire stretch, and pushing to build an entire new product for Black Friday while having COVID (again), I blocked two entire weeks of my calendar to do nothing except hold 1:1s with all 30+ team members.

Our team had grown a lot, and we had just pushed everyone through a season of intensity, so I felt 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.

It was a great reminder of how much people pay attention to your actions and what you do, more than the things you say but do not embody yourself.

Lesson #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.

The entire point of consumption (at least, through a 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 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’s 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 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’ve ever found high-consumption to be productive is when you have maxed out “More” of what you’re currently doing, but aren’t yet sure how to do it “Better.”

When this is the case, the right answer is to consume lots of different ideas and frameworks and ways of thinking so you can decide what’s worth prioritizing inside your existing vehicle.

But where this becomes a mistake is when you max out “More,” then go consume lots of different ideas and ways of thinking so you can entertain all the “New and Different” things you could do. 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.

Lesson #20: Every time you change what you “want,” you disrupt compounding and start over.

Lastly, this is probably the lesson I’ve been thinking about the most.

I became an entrepreneur in September, 2016. That’s when I quit my 9-5 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.

• End of 2016, all I wanted was to pay my rent as a freelance writer/ghostwriter and work toward becoming a full-time author.

• In 2017, I changed what I wanted and decided to scale my ghostwriting work into an agency and “real business.”

• In 2018, I changed what I wanted and decided to bring on two angel investors inside my ghostwriting agency and try to scale to the moon as a hybrid agency & software startup (massive 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.

• In 2021, I changed what I wanted and decided to scale Ship 30 for 30 with Dickie, and build another business and paid newsletter called Category Pirates at the same time.

• In 2023, I changed what I wanted and exited Category Pirates (after growing it to a multi-7-figure business in 24 months) and decided I wanted to build a more advanced business with Dickie—which is when we started our Premium Ghostwriting Academy.

• In 2025, I changed what I wanted and decided I wanted to try to scale PGA to the moon and spent hundreds of thousands of dollars on joining masterminds and millions of dollars running paid ads.

I remember making each of these decisions. And at the time, it seemed like the right decision based on the information and skills that I had.

But, looking back, I can now see the pattern with significantly more clarity.

Every time you “change what you want,” you essentially start over. You disrupt the compounding of your previous “want,” and swap it for something else.

As I move into this next chapter of life and business, this is a lesson I am taking to heart. And I am trying very hard to only play games I can see myself playing for 10+ years. Obviously, if I acquire new information and decide the right decision is to change course, 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 10 years, instead of changing goals every 2-3 years.

Dear Writer,

You should announce your goals to the world, and then you should document where you are today.

One of the most common questions I get asked by other writers & creators who want to start writing online is, “Cole, what’s the point? Why should I document and share anything about my life or where I am right now? I haven’t achieved anything yet. Who is going to want to pay attention to me?”

The answer is: nobody… yet.

You don’t document for other people. You document for yourself.

People like Gary Vaynerchuk have been preaching this for decades. In fact, I vividly remember sitting in the office of my first job out of college watching Gary’s first YouTube episode of #AskGaryVee and thinking, “This is what he means. He’s going to look back on these videos and be so happy he documented the journey.”

And that inspired me to do the same.

Back in 2014, I started recording as many random moments on my iPhone as possible. I didn’t know what I was going to do with them yet. I didn’t know whether they would hold any value, or if I would stand by the things I was saying a decade later. All I knew was that, at some point in the future, I would value the fact that I kept a time capsule—and that I documented myself along the way.

Unfortunately, I fell into the same trap everyone does:

• I recorded footage

• I would write blog posts or newsletters, announcing my goals to the world

• I’d get all fired up about “documenting the journey” and all the ups & downs of getting there

• And then I’d overthink, get in my own way, and end up not hitting publish

I was no more immune to these uncertainties than you, or anyone else.

A Video From 2016 Cole

But the other day, I was going through old photos on my phone—a quick trip down memory lane.

And I came across a video I had completely forgotten about. I don’t remember recording it. I don’t remember sharing it with anyone.

But from what I can gather, I must have recorded this sometime between October to December, 2016.

Some things going on in my life at that time:

• I had just herniated a disc in my neck weightlifting, was on painkillers, unable to lift, was depressed, and could feel my identity changing.

• I had just quit my 9-5 job working as an entry-level copywriter at an advertising agency downtown Chicago (September, 2016).

• I had just started making “real money,” going from my ~$44,000/year full-time salary to ~$20,000/month (~$250,000/year) ghostwriting like 4-5 hours per day.

• I had just published my first book—a coming-of-age memoir about becoming one of the highest-ranked World of Warcraft players in North America, called Confessions of a Teenage Gamer.

• I was still living in my studio apartment on the north side of Chicago. My income had gone up dramatically, but my lifestyle hadn’t changed yet.

• I had just started dating a girl long-distance who I’d met in LA (but lived in Arizona), who now, 10 years later, is my wife.

• I had just reconnected with one of my best friends from college, who lived in Atlanta, and we started visiting each other more talking about how we wanted to “start a business together.” (He became my co-founder in 2017 and together we built a ghostwriting agency to millions of dollars in revenue.)

• And I was going through a really hard time with my family, trying so hard to believe in myself and pursue my dream of building a life for myself as a full-time writer while dealing with their disapproval and their own uncertainty about what would happen if I “failed.” (When I told my dad I was going to quit my job and go all-in on writing, the first thing he said was, “How are you going to afford health insurance?”)

Basically, I recorded this video at the exact moment every major variable in my life was changing.

My identity was changing.

My relationship status was changing.

My income was changing.

My lifestyle was changing.

My goals were changing.

And I didn’t know how any of these variables were going to play out. Maximum uncertainty.

The only thing I did know was that I would figure it out—by any means necessary.

So when I recorded this video, I wasn’t really recording it for anyone else.

I was recording it to my future-self, for my present-self.

When I came across this video and watched it the other day, almost a decade later, I felt so emotional. It was like opening a time-capsule and being able to re-experience a previous chapter of life. I felt so proud of 2016-Me. Because I owe who I am today, and all the things I have achieved, to him.

Chicago Cole.

He was the one who woke up early and stayed up late.

He was the one who chose to write every Saturday and Sunday for as many hours as possible.

He was the one who put his goals and aspirations above everything else.

And he was the one who had enough foresight to pick up the camera and say, “This is what I want out of life, and I’m going to go get it. Watch.”

I share all of this because there’s no reason why you can’t do the same.

In fact, part of “documenting the journey” means admitting to yourself that you don’t know how it’s going to play out. You don’t know whether or not you’ll “be successful.” You don’t even know if the version of success you think you want is what you’ll actually get. You don’t know. Maybe it’ll turn out even better than you imagined!

The point is, the reason documenting the journey holds so much nostalgia and long-term value isn’t because of the known. It’s because of the unknown.

If there was a 100% chance things went exactly the way you thought they would, there would be no journey. Because there is no risk.

The risk is what makes it interesting.

And the risk is what makes it rewarding.

So, start now.

It’s never too late to begin documenting where you are on your journey, working in the direction of wherever it is you want to go and whatever it is you want to achieve.

And I promise, wherever you are today… 10 years from now, you will wish you had started sooner.

—Cole

PS: Let me know if you enjoyed this little blast-from-the-past. I have tons of old footage I have never shared. But I will, if you find it as interesting and helpful as I do.

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Want to write online, build your personal brand, start (or scale) your newsletter, and monetize? Come write alongside me inside our AI Writing Skool!

Dear Writer,

In my book, Writer Career Paths, I talk about how the highest-earning writers in the world are all fiction writers.

• J.K. Rowling: Billionaire

• James Patterson: $800M+

• John Grisham: $500M+

• Stephen King: $500M+

• Agatha Christie: $100M+

The only exception to this rule (that I’ve found) are copywriters who end up building businesses of their own—which I would say makes them more “entrepreneurs” than “writers.” For example, I have a friend & mentor who is a copywriter-turned-entrepreneur worth hundreds of millions of dollars.

But in terms of pure “writer”-related career paths, if you want to make the most money you can over the longest time horizon, fiction wins by a mile.

The problem is…

Selling books is hard—because publishing is a very challenging business model.

• Books are one-off purchases. There’s no subscription revenue, unlike say a Substack paid newsletter.

• Books are price-capped. You’re unlikely to be able to charge more than $5 or $10 for an eBook, or more than $20 or $30 for a print book. Even with a collectors edition, you’ll probably max out between $50 and $100.

• And books are physical goods. eBooks are digital, which have no marginal cost. But print books have all sorts of marginal costs: printing costs, warehousing costs, shipping costs.

So how much money does the average novel make?

And is there a difference between self-published novels and novels with traditional publishers behind them?

Well, the average self-published book only sells between 50 and 250 copies over its lifetime. 90% of self-published books sell fewer than 100 copies total. And if you think things get better or easier with a book deal, it’s only marginally. The average debut author with a book deal sells between 500 and 2,000 copies.

So let’s be extremely generous and say:

2,000 copies x $20 per book x 15% royalty (which is above industry standard) is $6,000 pre-tax.

Not a lot of money.

Fiction is what I like to call a Lottery Game.

If you want to make money fast as a writer, you shouldn’t write fiction and you should pick a different business model.

You should write non-fiction and:

• Launch a paid newsletter

• Start a paid community

• Or sell digital products

These business models, paired with writing that helps a specific reader solve a specific problem in their life or business, will almost always generate more revenue faster than fiction. (I know because I’ve generated over $20,000,000 in revenue writing non-fiction and selling these types of products.)

But…

If you want to make the MOST money you can as a writer, and you’re willing to play the long game, you should write fiction.

Because:

• Fiction retains its value exponentially longer than non-fiction. The average non-fiction book has a shelf-life of <5 years. Whereas the average novel has a shelf-life of forever.

• Fiction lends itself better to volume. Even the most prolific non-fiction writers can only write so-many-books on the same topic. But the most prolific fiction writers can write infinite mysteries, or fantasy stories, or romance-thrillers.

• And the more fiction you write, the longer each customer’s lifetime value (LTV). More books in your library means more products for your target reader to buy. So the more fiction you write, every net-new reader you attract is a more valuable customer—because they won’t just buy and read one of your books, they’ll binge your whole library.

But I actually don’t think it needs to be an Either/Or.

Fiction writers would make so much more money if they paired their books with other business models that are more lucrative in the short term.

So if you want to become a 6-figure fiction writer, there are 6 revenue streams you should consider building for yourself:

1. Your library of books—and I’d actually recommend writing both fiction & non-fiction.

2. An early-reader paid community—unlocking subscription revenue, and giving readers early access to books in-progress and before they’re published.

3. A paid newsletter—another subscription revenue source, where you can either share book excerpts, behind-the-scenes content, or How To resources to help readers who also want to write like you.

4. Digital products—monetizing all your frameworks for how you “do what you do.”

5. Affiliate partnerships—easy passive revenue for recommending tools you use, or promoting other authors’ books on Amazon you’ve enjoyed.

6. And live paid workshops—giving readers and fans a different level of access to you and your writing.

This is how you reduce your reliance (and risk) on purely selling books, and make your writing business more defensible and profitable.

Let’s walk through each one:

Share The Art & Business of Writing

Revenue Stream #1: Write Lots Of Books

If you want to make money as a fiction writer, you have to realize you’re playing a volume game:

Freida McFadden, a big-name psychological thriller writer with books like The Housemaid turned into a movie starring Sydney Sweeney, has written over 30 novels—with over 250 titles on Amazon, including different formats (eBook, audiobook, and print books) translated into dozens of languages.

Seth Ring, a hugely successful indie LitRPG writer, has written over 50 novels across more than 8 major series’.

And maybe the greatest example of all:

James Patterson has written over 100 novels, and on Amazon has over 1,600 titles listed across different formats and translations.

The point is, Volume Wins.

Very rarely do you see a Fiction Writer consistently earning 6 figures or above, year after year, without volume. J.K. Rowling is a complete outlier—the equivalent of winning the Powerball of fiction. But everyone, if you want to have a long-lasting career, is expected to write and write a lot.

The reason is because fiction readers tend to be Superconsumers. Meaning the average serial fiction reader doesn’t just read one novel per year. Most read a novel per week. Just look at BookTok if you don’t believe me. So, as an author, you need to be publishing books often enough to keep readers coming back again and again—servicing that demand, but also extending the lifetime value of each reader you attract.

Revenue Stream #2: Launch An Early-Reader Community

Early 2026, I went to a Fiction Writing Mastermind held by 7-figure indie fiction author, Seth Ring.

And my biggest takeaway for how he consistently drives book sales and reviews at launch is by building an Early-Reader Community.

This is a paid subscription—his is $50 per month—that gives readers:

• Early access to your book-in-progress

• The ability to make suggestions and be part of the writing experience

• And a private community (usually hosted in Discord or Slack) where they can interact with you, the author, as well as other superfans of your fiction

And this Early-Reader Community actually does 3 really valuable things all at once:

• It creates a revenue stream of subscription revenue. Beta-readers have to stay subscribed in order to receive the ongoing benefits.

• It creates a private, incentivized group of readers—who are 10x more likely to leave reviews on the day or week of your book’s launch.

• And these readers double as “editors.” They read your story before it gets published and not only leave suggestions and feedback, but help you catch spelling, grammar, and consistency mistakes as well.

All of these benefits are costs for the average author.

But by treating each of these as benefits inside a subscription service you provide your most avid readers, you can flip all of these costs into revenue.

Share

Revenue Stream #3: Launch A Paid Newsletter

Every writer should have a newsletter.

The reason is because your newsletter is your engine.

When you try to get a book deal, for example, the size of the advance you get is directly correlated to how big your email list is.

• If you have no email list, or a small email list, except a small advance.

• If you have a big email list, expect a larger advance.

This is because your email list is the most reliable metric publishers use to anticipate book sales. Even more than followers—because social platforms have changed over the years, and followers are no longer an accurate metric. You could have a million followers but make a post and only have 1,000 people see it. Whereas if you have 1,000 email subscribers, with a 70% open rate, that means 700 people will see it. Email is far more valuable than social.

And if you decide to self-publish, the same is also true: your email list is the greatest predictor for how many copies you will sell, and how many reviews you will attract, in the first week of your book’s publication.

But every writer should also consider building a paid newsletter as well.

Paid newsletters are one of the simplest but most lucrative business models for writers.

• It’s subscription revenue—you charge $10 or $20 per month for readers to get access to content they can’t get anywhere else.

• It’s a very simple business to run—you don’t need to learn any advanced entrepreneurial skills like phone sales, automations, or how to hold in-person events. All you have to do is write exclusive content and put it behind a paywall.

• And it’s a forcing-function for you to get paid to build an audience of superfans—because readers who subscribe to your paid newsletter are essentially raising their hand saying, “I love what you do, and I’m happy to give you more money in exchange for more content.”

So if you want to start a paid newsletter, the platforms I’d recommend considering are:

Substack

This is the easiest one, very simple, and free to use.

There’s no monthly fee, but they do take 10% of your revenue.

However, Substack is also a platform in-itself, so yes you give up 10% but Substack also brings you readers. For example, I have a huge paid newsletter on Substack called Write With AI that does over $300,000 per year in annual recurring revenue. And I have no problem paying Substack $30,000 per year because over 55% of all our subscribers have come from inside Substack’s network.

That’s free growth.

Patreon

In the fiction world, a lot of writers launch paid memberships on Patreon.

For example, this is where Michael Chatfield, who is a 7-figure fiction writer, hosts his membership site.

Patreon is like Substack just with more functionality. But ultimately, they achieve the same end-goal, which is creating a paid tier of access to exclusive content that unlocks subscription revenue from your most loyal readers.

Skool

The third option is to launch a paid Skool community.

• A paid newsletter…

• Is pretty much the same thing as a Patreon membership…

• Which is pretty much the same thing as a Skool community.

They’re just different platforms, with different functionality, but the end-game is the same: exclusive content and subscription revenue.

In the world of fiction, a good example to look at is Story Hacker AI by my friend Jason Hamilton.

Revenue Stream #4: Upsell Readers On Digital Products As A Fiction Writer

As a fiction writer, some percentage of readers want to know how you “do what you do.”

And they will happily pay you in exchange for giving them the secret sauce.

For example, imagine if James Patterson had a thriller-writing course. Actually, he does, it’s just on Masterclass and it’s more edu-tainment than purely actionable education.

But imagine if he had a $350 digital product on his website where he showed you:

• 10 outlines from his 10 best-selling novels

• A step-by-step walkthrough of how he goes from idea to outline to written chapter

• Templates you can use to quickly create high-quality thriller plots for yourself

• And a behind-the-scenes screen-recording of him writing 5 chapters right in front of you

If you love James Patterson, and you wanted to write thriller novels too, what are the chances you spend $350 to learn directly from him?

The answer is very, very high.

And to put that in context, if the average James Patterson novel is $10, that means 1 digital product sale is worth 35 copies sold.

Which is why I tell all writers—both non-fiction and fiction writers—to consider having at least ONE digital product as an upsell to your readers, where you teach them how you “do what you do.”

Because some percentage of people who READ your fiction will also want to WRITE fiction too.

I have been doing this for years.

I have generated over $5,000,000 selling stand-alone digital products.

These are $350 text & video courses, each focusing on different writing-related skills.

• Ship 30 for 30—a 30-day writing program for anyone who wants to start writing online, build an audience & personal brand, and dominate a niche of their own, including daily assignments, templates, and even AI prompts.

• Self-Publishing Studio—how to write, publish, and market a non-fiction book in 14 days.

• Substack Starter Kit—how to start a free or paid newsletter on Substack.

• Category Newsletter Creator—how to build a category-defining newsletter and use Kit to run your entire digital product business as a writer.

• Low-Ticket Launchpad—how to create & sell a $350 digital product online.

• LinkedIn AI—how to build an audience on LinkedIn and use AI to scale your content & engagement.

• Decision Journaling—how to build a daily writing habit and use journaling as a mechanism to make hard decisions in your life.

• Ghostwriter GPT—The 10 AI prompts you need to run your ghostwriting business.

And I plan to continue building more and more cutting-edge digital products in the writing world, including doing the same in the realm of fiction.

Revenue Stream #5: Make Extra Money As An Affiliate

One of the easiest revenue streams to add to your monetization stack as a writer is to be an affiliate for other products and platforms you use and regularly recommend yourself.

For example…

• We host all of our digital products and communities on Skool. So when we talk about Skool, we give readers our affiliate code.

• We run our entire business and all our email automations using Kit. So when we talk about Kit, or train writers on how to set up different sequences inside of Kit, we also give them our affiliate code.

• Our primary company websites are all built and hosted on Webflow. So when we educate writers on how to set up a website, and we recommend they use Webflow, we also give them our affiliate code.

The important thing to note here is that you often talk about the platforms and products you use without even realizing it. You aren’t “promoting” them. You’re just genuinely telling people what you use and why you like it.

And this work (that you’re already doing) that very easily be turned into a passive revenue stream just by signing up as an affiliate for each product or platform you regularly talk about.

Especially as an author, you should also sign up as an Amazon Affiliate.

Authors tend to read and talk about books—a lot.

So, every time you talk about or recommend a book in your content, and link to it on Amazon, you should use your Amazon Affiliate Code! It’s a very easy way to collect some incremental revenue in exchange for doing the work of a) creating content, and b) marketing other people’s products.

*I hear often from writers how they don’t want to sign-up and become an affiliate because they don’t want to be sales-y. Or that being an affiliate is deceptive. Or they just want to promote other people’s stuff “for the sake of it.” Fine. I’m just letting you know you’re leaving money on the table, and there’s nothing wrong with being an affiliate. There’s a reason affiliate marketing is one of the largest marketing industries on the planet. It’s very effective because incentives are aligned!

Revenue Stream #6: Monetize Your Writing Skills With Paid Workshops

The single easiest way to charge more and make more money as a writer is to provide customers with more access to you.

And the simplest, easiest way to “sell” increased access without signing yourself up for hours and hours of obligations is to hold a one-to-many paid workshop on Zoom.

• Pick a topic—something you want to show and teach other people how to do.

• Pick a time constraint—most paid workshops are between 1 and 3 hours.

• Charge money—I would recommend no less than $20 and no more than $150 per ticket.

• Include bonuses—and give away tangible assets (mini digital products like templates, worksheets, etc.) to sweeten the deal of someone signing up.

• Upsell something at the end—like another relevant digital product, or your paid newsletter, Patreon, or community, or maybe even a book you just published.

Paid workshops are amazing because they are paid events that provide one-time LIVE access to you, but more importantly, tell you who on your email list is willing to pay you more money in exchange for more information and/or access. (Pro tip: this list of people almost always ends up becoming your list of Superconsumers who buy nearly everything you create. You want to know who those people are!)

For example, back in 2023 when ChatGPT first came out, and we started incorporating AI into our daily writing workflows, we “double-monetized” that skill by also teaching other people how to “do what we were doing” on a live workshop.

And we made an extra $63,000 in revenue in 72 hours, just pitching our email list on a 2-hour live workshop with us.

If you want some insight into how we did this, I recommend watching this video:

And something advanced you can do after holding a paid workshop, by the way, is unlock another revenue stream by:

• Selling the recording for a cheaper price—so if the paid workshop is $99, maybe you sell the recording for $49 afterwards (monetizing the content again).

• As you run more paid workshops, you begin to compile a vault of recordings—and the vault can be sold as a bundle (say $350) or added as free bonuses or incentives when selling another digital product or paid workshop.

• And if you have a paid newsletter or run a membership or Skool community, you can give members free access to these paid workshops and store the recordings behind the paywall—meaning your paid workshops act as retention mechanisms for your monthly recurring subscribers. (So it doesn’t really matter if you sell a new customer, or retain an existing customer, revenue is revenue.)

There’s levels to this strategy!

Most Writers Struggle Because They Only Have 1 Revenue Stream

Your big takeaways here should be:

• As a Fiction Writer, your primary business model will always be writing and selling books. This is because the whole point of writing fiction is to participate in the Lottery Game. Most of what you write won’t make very much money. But once a book breaks out, you can achieve an outlier event.

• But, you don’t want to be solely reliant upon one revenue stream. Book sales are very volatile, and a volatile financial life doesn’t make for a great state of mind (certainly not conducive to creativity!).

• By only writing books, you end up leaving a ton of money on the table. Your readers would love to pay you for more information, access, and/or exclusive content. Let them!

• And by building other revenue streams, you don’t just “make more money.” You make yourself more defensible! You become less reliant upon any one individual revenue stream, and instead can build a more well-rounded writing business.

So, stay focused on writing books.

But also… monetize the attention your books attract with some of these other business models.

—Cole

Founder of Different Publishing (you can find all my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

Co-Founder of Velocity

Co-Creator of AI Cole

The Art & Business of Writing is my free newsletter on how to write in the digital age and make money doing it. New posts every Friday!

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Dear Writer,

I am a big fan of “Speedwriting”: setting a timer and seeing how much you can accomplish within that predetermined container of time.

And let me give you some context as to why:

Back in 2017, I started my first business.

It was a ghostwriting agency, called Digital Press.

I am not exaggerating when I say that from late 2016 (when I was ghostwriting on my own), through late 2019 (scaling our agency to 23+ full-time employees, 80+ clients around the world, and $2M in yearly revenue), I was ghostwriting somewhere in the ballpark of 3-5 articles per day, for 3-5 different clients, 6-7 days per week.

When I audit the different chapters of my life, and the periods when my skills as a writer improved the most, I can say, without question, 2017-2019 was when I saw the most growth. Not just because of the amount of volume and hours of practice I was racking up each week, month, and year. But because the majority of this practice had to happen in very inconvenient containers.

• I was traveling a lot for work, visiting clients → still had to ghostwrite articles.

• I was traveling to Atlanta to see my co-founder → still had to ghostwrite articles.

• I was traveling to Arizona to see my then-girlfriend → still had to ghostwrite articles.

• I was driving around LA to pitch or meet with clients → still had to ghostwrite articles.

I did not have the luxury of sitting quietly in my apartment for six uninterrupted hours. In fact, if I wasn’t traveling and writing articles in airports, cabs, or hotel rooms, I was ghostwriting articles in my apartment in strict 45-minute time blocks between sales calls, or employee calls, or employee interviews, etc.

(I wish I had AI technology like Ghostbase way back then!)

For example, here’s a picture of me (in a bathrobe) trying to take a vacation in Cartagena, Colombia, with my now-wife (back then, we had only been dating a few months), ghostwriting an article before dinner—which is how I paid for that dinner.

I share all of this because I think, especially when it comes to writing, writers like to believe they need the “perfect environment” in order to write.

And what I ended up learning was: that’s just an excuse to avoid doing the work.

If you practice only writing when you’re in the “perfect environment,” then writing only happens in those rare moments. But if you practice writing in “any” environment, no matter how uncomfortable, then you will build a tremendous amount of resilience. YOU will decide when you want the writing to happen—opposed to deferring responsibility and expecting “the environment” to decide for you.

Which is why I’m such a big fan of Speedwriting.

What Is Speedwriting?

Speedwriting is where you pick an asset (the “type of thing” you want to write) and then begin to benchmark your ability to create that thing within a specific container of time.

Think of it like training to run a 5-minute mile.

If you were to train for a 5-minute mile, what would you do?

• You’d decide, “I want to set the goal of being able to run a 5-minute mile.”

• You would run a mile—and time yourself.

• And then you would take your time and look for areas of improvement.

• Then you’d try again, measure your time, and look for areas of improvement.

• And so on.

And you would repeat this process, over and over again, until you could successfully run a 5-minute mile.

Well, the same thing is true for writing—specifically, training your brain to write a certain type of asset within a container of time.

This is what I did ghostwriting 800-word thought leadership articles.

Since most of my writing had to be done in tight windows—usually between sales or team calls—my container of time was about an hour.

And you want to know what happened?

Somehow, I’d find a way to get that piece written inside that container of time. (Sometimes I wouldn’t. Sometimes I’d fail. Sometimes I’d have to come back for a second round later. But over time, I was able to more consistently achieve the end goal of “writing an article” within that container of time.)

And from here, I began to tighten the window of time:

• Could I write an article in 45 minutes?

• Could I write an article in 30 minutes?

• Could I write an article in 15 minutes?

As my skill improved, I would challenge myself by tightening the time window more, more, more, more.

Until eventually, 3 years later (2019), there were some clients whom I could ghostwrite an entire 800-word article for in 11 minutes (my record to-date).

No edits. No rewrites later.

Blank page to finished draft sent to the client in 11 minutes.

And seeing my growth, and my ability to do that, completely changed the way I think about writing—specifically, Speedwriting.

How To Write FAST

I’m going to let you in on a little secret.

The whole key to Speedwriting is not actually effort.

You get marginally faster when you are solely focused on “working harder.” Because the truth is, there’s only so fast your fingers can type, and there’s only so intensely you can focus. Very quickly, “effort” gets maxed out.

Which means speed improvements need to come from somewhere else.

Here’s the secret to Speedwriting: you have to upgrade your mental models for “how you work.”

The biggest step-function changed I’ve ever experienced in writing non-fiction was when I changed from writing “linearly” to writing in blocks.

Let me explain:

• Most writers write linearly. They open a blank document. And then they start at the very top, and work their way down. They write the first word. Then the second. Then the third. Then they don’t like the third word, so they delete it. Then they decide they don’t like the first two words, so they start over. And they repeat this process of slowly inching their way down the page until they’re “done.” (This is incredibly inefficient.)

• What I ended up doing is writing in blocks. Instead of writing linearly from top to bottom, I would start by dividing the page up into sections (blocks). And then fill each section with notes. And then re-write my notes, inside each section, as prose.

I even game this framework a name.

I call it Prepping The Page.

Here’s a throwback video I recorded back in 2021 showing exactly how I do this—specifically with articles/essays.

The Benefits Of Block-Writing (“Prepping The Page”)

Now, why is this so effective as a mental model?

For a few reasons:

1. First, it forces you to make the highest-leverage decisions first. When you write linearly, you waste a lot of time obsessing over things like sentence structure, word choice, and grammar. But all of these variables are, to put it bluntly, worthless, if they are not organized into the correct sections, organized in the right order. Prepping The Page, and thinking in “sections-first,” forces you to clarify your thinking before you dive into the writing.

2. Second, it reduces the likelihood you will be stricken by Writer’s Block. All of a sudden, you aren’t staring at a blank page. You are staring at a page, organized into sections, with the “thing you’re trying to say” already decided inside each section. Now, the writing is easy! All you have to do is re-say your ideas, organized into each section, better (in prose).

3. Third, it breaks your “sprint” up into sections—which makes it feel more approachable. Instead of feeling like you have to write a whole <asset>, you can see each section as a mini “mile marker,” tracking your progress.

This block-writing technique is now how I write everything.

• This is how I write articles/essays.

• This is how I write emails (and entire email campaigns).

• This is even how I write books.

And it’s one of the primary techniques I teach inside our beginner writing program, Ship 30 for 30—as well as our ghostwriting program, Premium Ghostwriting Academy.

For example, check out the below video where I apply this same strategy to writing an entire email campaign for Black Friday:

Speedwriting Books

But my favorite use case for this mental model has been how it has changed the way I write books.

• My first book, Confessions of a Teenage Gamer, took me 4 years to write. That’s because I was writing linearly (and it was very painful).

• My second book, The Art & Business of Online Writing, took me 4 months to write. This is when I started experimenting

• My third book, The Art & Business of Ghostwriting, took me 4 weeks to write. This was the project I really started to figure out how to apply “Prepping The Page” to books.

And now, I can write an entire non-fiction book in a week (if I want to).

*Obviously, some projects—depending on the subject matter and my familiarity with the topic—take longer. But my point is, this framework has had an exponential impact on my ability to write fast.

And just so you know (if you want to write a non-fiction book yourself & use this technique):

Next week, I’m hosting a 2-week bootcamp called Self-Publishing Studio, showing you how to write a non-fiction book from scratch (without using AI, but also using some insane prompts I’ve created if you want some help).

This includes:

• Coming up with the Perfect Book Title

• How to write your Origin Story Introduction

• How to outline a non-fiction book start to finish

• How to expand your outline using The 10 Magical Ways

• How to self-publish your book on Amazon (full step-by-step guide)

• And the most effective marketing strategies for selling your non-fiction book (the same strategies I’ve used to generate over $1,000,000 in self-publishing royalties)

I have written and self-published 10 books. And I’m so excited for this bootcamp because book-writing is a topic I haven’t talked much about.

So if you’ve been wanting to write a book of your own, hop aboard!

My goal is to help you make 10 years of progress in 2 weeks.

Click here to join the Self-Publishing Studio Bootcamp.

My 25-Minute Book Outlining Process

And if you want a high-level overview of how this works, I recommend giving this video a watch:

My point is… the way you get better at writing, faster, is by doing the following:

• Pick an asset (the type of thing you want to write)

• Set a time constraint

• Try to create that asset within that time constraint

• See how far you get (time yourself)

• Look for what could be improved (it’s usually the mental model you’re using to approach the work to begin with)

• Try again

• Repeat forever

Don’t edit.

Don’t overthink.

Just time yourself. Get to work. And watch how, somehow, your brain adjusts to the container you’ve given it.

(Parkinson’s Law: work expands so as to fill the time available for its completion.)

Cole

Founder of Different Publishing (you can find my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Ship 30 For 30

Co-Founder of Premium Ghostwriting Academy

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

PS - I wrote this newsletter while my dog was barking at the plumber who had to come by my house to fix a toilet.

Stop waiting for the perfect environment to write.

Want to write online, build your personal brand, start (or scale) your newsletter, and monetize? Come write alongside me inside our AI Writing Skool!

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

Dear Writer,

One of the greatest “surprising but believable choices” ever made in the history of storytelling is in Star Wars V: The Empire Strikes Back.

Near the end of the movie, and during the epic lightsaber battle between Luke Skywalker and Darth Vader, we finally learn the truth. Vader says, “Luke, I am your father.” And we see young Luke Skywalker crumble under this realization.

• This is Surprising, because the story has clearly pinned Luke and Vader against each other. And we don’t expect these enemies to share something so deeply personal: they’re family.

• But this is also Believable, because there are only so many Jedi in the world, and in hindsight, the clues make sense. Luke hasn’t known the identity of his parents, but he’s been told his father was a powerful figure.

A story is not merely “a series of things that happen.” Or even, “a series of consequential things that happen.”

The best stories, the ones that lodge themselves into our minds and stay there for decades, are “a series of Surprising but Believable things that happen.”

That’s why generations of sci-fi fans continue to recite that iconic line: “Luke, I am your father.”

Believable Is Boring

Here’s a “Believable” story:

• A boy’s mom asks him to walk down the road to the gas station to buy her a jug of milk

• The boy, young, only in middle school, walks down the road to the gas station.

• He asks the gas station attendant where the milk is.

• The gas station attendant points to the milk in the refrigerators along the back wall.

• The boy grabs a gallon of milk and walks it back to the counter.

• The gas station attendant takes his $5 bill and hands him the change.

• The boy walks the jug of milk back home.

Everything about this story is Believable—which is fine, that’s what grounds it in some sort of reality. But from a plot perspective, Believable is Boring. Nothing really happens!

Now, it’s worth pointing out that there is still value in “Believable but Boring” stories.

In fact, this is a lot of what gets produced in the world of Literary Fiction.

Most Literary Fiction isn’t about anything Surprising—and if there is a Surprising element, it happens once and that’s about it. The rest of the story is straightforward, oftentimes mundane.

Which is why the “value” of Literary Fiction tends to rely on other storytelling variables besides just plot. If a story is Believable but Boring, then the value has to come from somewhere else: maybe it’s the voice of the narrator that keeps you interested; maybe it’s the beautiful language, the colorful description, the visceral metaphors; or maybe it’s the narrator’s commentary on themes in society that resonates with your point of view, validating or stress-testing the way you see the world.

The point is, the “value” of a story can be any number of things. There is stylistic value. Plot value. Thematic value.

But if you want to maximize the plot value, specifically, then you’re playing a game called: How Do I Make As Many Surprising But Believable Choices In The Story As Possible?

Surprising Is A Shtick

If Believable is one side of the spectrum, then Surprising is the other.

But Surprising decisions, by themselves, are not valuable.

For example, here’s a “Surprising” story:

• A boy’s mom asks him to walk down the road to the gas station to buy her a jug of milk

• The boy, young, only in middle school, walks down the road to the gas station—but gets abducted by an alien.

• He asks the the alien where the milk is—and the alien says, “It’s time you die.”

• The boy dies—but then gets reborn as a purple cow.

• As a purple cow, the boy befriends a leopard who only communicates in show tunes.

• Together, they decide to start their own 2-person show-tune traveling band.

• And on the road, the leopard finally confesses his love to the boy, who decides he can no longer be a purple cow, and begs the aliens in the sky to return him home.

• The aliens do return him home, but weld a purple cow tattoo onto his arm so he’ll remember this journey forever.

• His mom then asks why he didn’t bring home any milk.

Wow! Everything about this story is Surprising!

But does that make it “good?” Not really. A lot happens—but the happening doesn’t hold very much value. It’s just one Surprising thing after another, with no real intention or, and this is the key word, Believability.

Which is what makes Surprising a Shtick—a very easy mechanism to overuse.

The Stress-Test Of Surprising But Believable Choices

So, what are the limits of Surprising but Believable choices?

In creative writing, the limit is typically referred to as “the suspension of disbelief.” Surprising but Believable choices don’t have to be realistic (sci-fi/fantasy proves this). It’s about whether or not each choice is believable within the rules of the story. A reader will happily accept a futuristic mechanical dragon powered by an ancient dragon heart if the magic system of the story has logic that can support it. But a reader will reject a character in a medieval fantasy world suddenly checking their email on a flip phone because that would break the rules of the story—it would be Surprising, but it wouldn’t be Believable.

Here are some easy giveaways a piece of writing has failed the stress-test of successfully navigating the suspension of disbelief:

• The story contradicts its own internal logic: A character suddenly has a skill they’ve never shown before, or experiences something that doesn’t make sense in this world.

• Coincidences solve problems instead of the characters having to figure things out on their own: This is commonly known as deus ex machina, a plot device where an unsolvable, hopeless problem is suddenly and abruptly resolved by an unexpected, unlikely intervention ****(like a new character, ability, or object) ****that was not previously foreshadowed. It’s a “contrived” ending to a situation that feels unearned, often favoring luck over character action.

• Dialogue sounds like a writer talking, not a person: This is where the writer peeks their head out too far from behind the curtain, and makes their presence too felt (often over-sharing their own personal beliefs, opinions, etc.)—which breaks the suspension of disbelief and mysticism of the story. As readers, this is the moment we realize this fiction world is indeed… fictional.

• Research fails conspicuously (wrong gun, wrong law, wrong era, etc.): This is an easy one to avoid. Do your homework.

• Stakes deflate (no one really gets hurt, nothing really changes): This is what’s known as a Red Herring, which is a distraction, clue, or piece of information intended to mislead or divert attention. Murder mysteries notoriously overuse this mechanism, trying to make every action in every scene leave you questioning: “Wait.. are they guilty? Or wait… is this other person guilty? OR WAIT… IS IT THIS OTHER PERSON WHO IS GUILTY?”

Now, here’s how to think of Surprising but Believable choices as a skill that you can improve.

Writing Exercise: Practice Making Surprising But Believable Choices

In any given situation, characters have multiple different choices they can make.

And it’s not that any choice is “right” or “wrong” (so long as the choice doesn’t break the suspension of disbelief). It’s just that some choices are more Surprising (aka: effective & memorable) than others.

For example: let’s say you’re writing a story about a high school football star who gets into a near-fatal car accident.

Whenever something “happens” in a story, you (the writer) have to make a choice.

What happens next?

And 3 categories of choices immediately present themselves:

• The Believable but Unsurprising Choice: The high school football star gets hit by a drunk driver. (We’ve all seen this movie a hundred times. Very predictable.)

• The Unbelievable Choice (breaking the suspension of disbelief): The high school football star gets hit by his arch rival’s mother who wants to murder him to see her own son succeed. (Surprising, sure. But Believable? Ehhhh… that’s pretty extreme.)

• The Believable but Surprising Choice: The high school football star gets hit by his alcoholic coach and mentor, whom we’ve watched struggle with alcohol the whole story, and whom we’ve also watched the high school football star try to help and repeatedly fail. (Now that’s a story!)

Notice how none of these choices is “the right choice” to make in the story (right and wrong are subjective). They’re just different available moves on the chessboard.

But, like chess, some moves are more effective than others.

And you must search a little harder, and stare at the board a little longer, to discover those Surprising but Believable moves.

How To Practice Making Surprising But Believable Choices

First, make a list of things that “happen” in your story:

• Main character, a mechanic on a remote desert planet, discovers a foreign ship has landed in his backyard.

• When main character explores the ship, he tries to steal the comms system but accidentally discovers a map.

• When the main character returns home with the comms system and map, he’s jumped by a group of rebels who have been searching for the same map—and taken hostage.

Next, within each “action,” build your pattern recognition by coming up with ideas inside all 3 categories of choices:

• The Believable but Unsurprising Choice:

• The Unbelievable Choice (breaking the suspension of disbelief):

• The Believable but Surprising Choice:

This will help you learn to recognize which direction your ideas tend to default.

(Pro tip: the brain almost always tilts toward the Believable but Unsurprising Choice first, second, and third. You usually have to sit there and think about it for longer than 30 seconds to see the Believable but Surprising Choice on the chessboard.)

Your list should look something like this:

• Main character, a mechanic on a remote desert planet, discovers a foreign ship has landed in his backyard.

  • The Believable but Unsurprising Choice: The main character recognizes the ship. It’s the same type of ship as every other ship on this planet.

  • The Unbelievable Choice (breaking the suspension of disbelief): It’s a ship from a completely different time period—a Pirate Ship!

  • The Believable but Surprising Choice: The main character doesn’t recognize the ship, but when he gets closer, he realizes the logo on the side of the ship is the same logo on the leather-bound cover of his father’s old journal—and no one has seen his father in years.

• When main character explores the ship, he discovers a map.

  • The Believable but Unsurprising Choice: It’s a regular old map, wedged into the corner, that the character finds easily.

  • The Unbelievable Choice (breaking the suspension of disbelief): He doesn’t find the map, the map finds him! The map jumps off the table and walks over to the main character, introducing itself.

  • The Believable but Surprising Choice: The character sees a brand-new communications system in the cockpit and decides to try to jack it—maybe it’ll be worth some money. But as he tries to break it off, he accidentally triggers the system to show him a holographic display, a map. And on the map, it shows the same logo again, with coordinates to a home base on a planet the character remembers hearing at some point in the past. Maybe that’s where his father is?

• When the main character tries to return home with the map, he’s jumped by a group of rebels.

  • The Believable but Unsurprising Choice: The main character, carrying the comms system hoping to sell it in town, gets jumped and they steal the comms system for themselves. Map gone.

  • The Unbelievable Choice (breaking the suspension of disbelief): The main character gets jumped, but then two seconds later the crew says, “We know your dad. We’re here to take you to him.” (This would be a mini deus ex machina, the coincidence ruining the stakes of the story.)

  • The Believable but Surprising Choice: The main character gets jumped by a group of bandits who also saw the ship crash, and take him hostage. The main character offers them the comms system, thinking they just want the loot, and that’s when they reveal their true identity. They are part of a remote, secret group affiliated with the ship’s logo, tasked with bringing the map back to home base. And that’s when the main character asks to come along, saying that’s where he thinks his dad might be.

You should be able to see how there are many different “right” answers as to where you could take the story. And every time something happens, a new set of choices present themselves—over and over again.

Storytelling, then, is just a game of stringing together Surprising but Believable choices.

Which is what makes this such a valuable skill to build.

The Art & Business of Writing is my free newsletter on how to write in the digital age, and how to make money doing it. New posts every Friday!

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

And if you have any takeaways/questions, drop me a comment.

Cole

Founder of Different Publishing (you can find my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Ship 30 For 30

Co-Founder of Premium Ghostwriting Academy

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

Co-Founder of Velocity

Dear Writer,

Objections are not facts.

This is something I find myself coaching writers through on a weekly basis inside our Premium Ghostwriting Academy. Every Monday morning, I hold a Hot Seat session—students can sign up, ask questions, and workshop live. And just about every Monday morning, someone presents a scenario in which a client shared some sort of objection, and the writer wasn’t sure what to do or what to say, so the deal fell apart.

We’re going to fix that today.

But first, let’s talk about Objection Handling as a skill.

Objections are signals of a lack of education.

This is the first big reframe I like to help writers internalize.

When someone has an objection, 99% of the time that objection is not rooted in any “truth.” In fact, in all my years of ghostwriting, I’ve learned that the vast majority of people (including very smart, very accomplished, very successful founders, executives, and investors) don’t know why they want what they want, or why they think what they think. They might say to you, “I don’t think email marketing works for my target customer,” but just because they said it doesn’t make it true.

When a client says an objection, what they’re really saying is: “I don’t know how this works. And because I am uneducated, I am going to default to ‘No.’”

And this is where a lot of writers stop.

I remember when I first started ghostwriting as a 26-year-old. I was broke. I was living in a run-down studio apartment in Chicago. And I was talking to CEOs of multibillion-dollar companies. In the beginning, I had a very hard time not taking every word these incredibly accomplished people said to me as “fact.”

It wasn’t until, about two years later, after working with 100+ different clients, that I started to realize: yes, these people might be very successful, very wealthy, very smart… but when it comes to the thing I specialized in, which was ghostwriting and writing online, I knew more than they did. I didn’t know more, broadly. I knew more, specifically. And that realization completely changed the way I thought about working with, and selling, my writing services to clients.

You cannot overcome a client’s objection if you are unsure of the answer yourself.

This is where power-leveling your own knowledge becomes a crucial part of building the skill of overcoming client/customer objections—which is the whole secret to increasing your rates, charging more, and making more money.

If you aren’t intimately familiar with how something works (like how different social algorithms work, how newsletters get set up, what makes for a valuable piece of content, etc.) then when a client hits you with an objection—”I don’t think my target audience is on LinkedIn”—the conversation is going to crumble. Not because you aren’t talented. Not because what the client is saying is actually true. The conversation is going to crumble because, on some level, you aren’t sure whether they’re right or wrong. Your uncertainty is the culprit.

But now I want you to imagine that you spend 12 hours per day, 7 days per week, writing on LinkedIn. You study it obsessively. You’re always reading about it. Your feed is intentionally curated with other creators who also write about social content, so you can keep your finger on the pulse. And, you write content for yourself. You’re always practicing, experimenting, striving to have a complete and total understanding of how “this thing” works.

Then, one day, you hop on a sales call with a client. And that client says to you, “I don’t think you can get very much distribution on LinkedIn.”

• The “uncertain” writer here accepts this as fact. A successful person said it, so it must be true, right?

• But what the “certain” writer hears is a lack of education. Of course the prospect would think that… they don’t know anything about LinkedIn!

This is a very hard thing to explain to beginner writers (and even seasoned veterans who are stuck in their ways). We are conditioned in society to not question what an authority figure says—and as a writer, you are always providing writing services to figures of authority (business owners, entrepreneurs, big creators, etc.). So when presented with an objection, it’s very easy to default into the mindset of assuming: well they said it, so it must be true.

And that’s wrong.

If the client was educated, they wouldn’t have that objection.

As a business owner myself, I can see this in the way I make decisions.

When I am extremely educated about something, particularly how to solve a problem, I don’t need to be educated on “how it works.” I know what I’m solving for, and I understand the risk-reward of the experiment.

For example, tons and tons of business owners have an objection against creating content online. “I just don’t see the ROI the same way I see an ROI when I run Facebook ads.” When I hear someone say this, I know two things to be true:

• They are educated about Facebook ads.

• They are uneducated about organic content.

As a result, it’s common for these types of people to “object” against investing the time, energy, and attention into creating content online.

Conversely, we spend ~$50,000/mo+ on creating organic content.

Inside our company, we employ:

• Our own internal copywriters/ghostwriters

• Virtual assistants to help with cross-posting

• Tech operators & automation builders

• Video editors

• Designers

Could I tell you, down to the dollar, with 100% certainty, that when we spend $50,000 on our organic content team we generate $100,000 in revenue?

Of course not. Organic doesn’t work that way. It’s not like running Facebook ads—and I know that because I’m very educated about it.

Sales is Education

If you understand the above, and are able to recognize that objections are not “facts,” then you will naturally come to the next conclusion—which is Sales is Education.

So many writers (and freelancers/solopreneurs in every industry, across every discipline) don’t understand this. They think sales is about “selling,” about “persuading,” about “convincing,” and it’s not.

• If someone is uneducated about something, they will default to No.

• If someone is educated about something, they will default to Yes.

Let’s use a silly example, and even remove the objection of money:

Pretend your friend is trying to “sell you” on why you should start playing Pickleball.

And you know nothing about Pickleball. You are uneducated.

Even if your friend is “convincing,” does that mean you’re instantly going to take their word for it and start prioritizing Pickleball every Wednesday? Of course not. As a result, you default “No.”

But your friend doesn’t stop! So finally, one day, you relent.

What happens next?

You ask questions!

• “OK so how does it work?”

• “Is it hard to learn?”

• “Do you need a special racket?”

• “Where are there Pickleball courts around here?”

Questions are objections in disguise.

Your questions are actually all the reasons why you haven’t started playing Pickleball yet.

When you say, “No thanks, I don’t want to play Pickleball,” you are not stating a fact. You are admitting a lack of education. That lack of education shows up in the questions you ask. And as each question of yours gets answered, you will either:

• Become more and more open to the idea of playing Pickleball.

• Or, you will come to the conclusion that you don’t want to play Pickleball because now you know exactly what it entails.

The outcome of “the sale” isn’t what matters.

What matters is recognizing that the path to either outcome is the same: it’s education.

• The most effective way to “sell” someone is to educate them.

• And the most effective way to help someone, even if they don’t buy… is to educate them.

*(NOTE: A dead giveaway on a sales call that a client is interested, even if they say they’re not, is they will start asking you questions. “So how long does that take, usually? And what should I do if XYZ happens?” The mere fact they’re asking questions means they are trying to better educate themselves on how to make an informed decision.)

So, how do you educate instead of sell?

My Irresistible Offer Script: 8 Simple Steps

I have taken thousands of sales calls, and closed hundreds of high-ticket clients.

And I follow the same 8 steps every single time:

1. Here’s a problem you have in your business. You might not know you have this problem, or you know you have this problem but don’t know how to fix it (or just haven’t gotten around to it).

2. Here are the reasons why you have this problem. Let me educate you on what’s causing it.

3. Here are the consequences of this problem. Let me make you aware of the bad things that are happening as a result—as well as the other bad things that will continue to happen if you don’t fix this problem (and fast).

4. And here’s the ultimate negative outcome of this problem. It’s probably costing you in ways you aren’t even aware of. It’s making you stressed, keeping you from being able to spend time with your kids, etc.

5. Now, here’s an easy and reliable way to fix this problem. I know, because I spend all day, every day fixing this problem for people. I specialize in it. And the way you solve this problem is by <the product/service I provide>.

6. And here’s why this solution is so effective. Forget me for a second. Let me educate you on why this approach is more effective than all the other potential solutions (you may or may not have tried) that are out there.

7. Here are the benefits of this solution! It leads to lots of good things—let me tell you, specifically, what those good things are.

8. And here is the ultimate positive outcome we can unlock together. Let me paint you a picture. This problem is gone. But more importantly, this will help you solve for that ultimate negative outcome you told me about. Finally, stress-free! Finally, more time to spend with your kids!

Why is this considered to be an Irresistible Offer?

Because either way, you’re helping the customer/client.

• Either you sufficiently educate them to the point where they want to hire you.

• OR you sufficiently educate them to the point where they can make an informed decision about why the problem you’re proposing to fix (and the solution you’re proposing to fix it) isn’t actually a priority.

This is something a lot of people fail to realize about the sales process. The goal is not actually to “sell” every single person you talk to—because not every person is going to be ready for your help. They might not be ready because of timing, or budget. They might not be ready because, despite your 30 or 60 minutes of education, they still don’t fully “get it” yet. Etc.

So, going back to first principles, the goal is not necessarily to sell 100% of people. Obviously, you want to get good enough at educating prospects that a good percentage of them buy (industry standard would be to close 30% of your sales calls). But what about the rest of them? How do you increase the likelihood they come back around and want to work with you… eventually?

By helping them.

It’s so unbelievable simple—and yet, the simplicity is what makes it complicated.

People are more likely to work with you when they feel you have their best interests in mind.

And you don’t communicate that by “convincing” or “persuading” them to do something they don’t fully understand.

You do that by educating them to the point where they begin to sell themselves.

The Art & Business of Writing is my free newsletter on how to write in the digital age, and how to make money doing it. New posts every Friday!

Click here to watch the video version of this newsletter on YouTube.

Click here to listen to the audio version of this newsletter on Spotify.

And if you have any takeaways/questions, drop me a comment.

Cole

Founder of Different Publishing (you can find my books here!)

Co-Founder of AI Writing Skool

Co-Founder of Ship 30 For 30

Co-Founder of Premium Ghostwriting Academy

Co-Founder of Typeshare

Co-Founder of Ghostbase

Co-Founder of Write With AI

Dear Writer,

What is “writing?”

It’s a silly question when you think about it. Writing is words. Writing is communication. Writing is thought, articulated. Writing is documentation. All of these are correct answers—but they’re also unhelpful answers. Because each of these words, or sentences, intended to describe “writing” is a bundled term. What are “words?” What is “communication?” And so on.

I am now approaching the milestone of 20 years spent writing online.

• I started writing online in 2007, with a gaming blog about World of Warcraft back when I was a junior in high school.

• And since then (coming up on 2027), I have written thousands of newsletters, thousands of articles, ghostwritten thousands of opinion pieces and columns for executives, ghostwritten books, written 10+ books of my own, and built multiple 7-figure writing-related companies across a wide variety of different business models.

Needless to say, I’ve been doing this for a long time.

And still, I continue to ask myself: “OK… but what is writing?”

I am always in search of new frameworks to help me unbundle that bundled term, so that I might better understand what it is I’m actually trying to achieve by sitting here, stringing words together, for the benefit of my own understanding, sure, but to ensure there is value being provided to you, too.

So, I’d like to share with you a recent “lightbulb moment” I’ve had, and a new framework for unbundling that pesky word, “writing.”

The EDAN Framework

Oftentimes, when we read a piece of writing, we tend to perceive the thing only in its entirety. “This is a great book” or “this is a great essay” or “this is a great paragraph.” But there are two problems here. The first is that “great” is yet another bundled term. What does great actually mean? And second, a great book is really just the culmination of lots of great chapters or essays, which is really just the culmination of lots of great paragraphs, which is really just the culmination of lots of great sentences, which is really just the culmination of… what?

Exactly.

In order to understand what makes for “great writing,” we must look beyond any piece of writing in its entirety, and begin to unbundle it. We have to get down to the sentence level. And even then, we have to push past settling for bundled reactions—”I like this” or “I don’t like this”—so that we can analyze what’s actually happening. Whether you “like it” or “don’t like it” is irrelevant.

The more helpful question to ask is: “What is the writer doing here? And is it effective?”

And recently, I’ve realized that writing (particularly fiction, although there are elements of this framework that apply to non-fiction) is really just a game of four different choices:

EDAN stands for:

• Explanation

• Description

• Action

• Narration

At any given time, you (the writer) are choosing between these different “moves on the chessboard.” You are trying to decide between (E) Explaining some sort of context to the reader, (D) Describing the setting or character or situation and letting the reader extract meaning and context on their own, (A) using Action to move the story forward and/or reveal something about a character’s motives, or (N) using Narration to make the narrator’s POV (or your POV as the writer) explicit and known, overtly stating “the purpose” of the story.

Each piece here—EDAN—accomplishes something different, in a different way. And so it’s not that any piece is “right” or “wrong.” It’s that, depending on what you’re trying to say, and the feeling or takeaway you’re trying to elicit in the reader, you might consider choosing to “say it” using one piece over another.

So first, let’s walk through each one with an example.

And then, let’s take things up a notch and look for ways to combine these pieces together—which is the secret to “great writing.”

Explanation

Explanation is context.

In the writing cliché, “Show, don’t tell,” Explanation is the telling. And there is a lot of value in telling the reader why something is important, or giving them context to how a character’s actions should be perceived.

For example:

Let’s say you are telling a story—doesn’t matter if it’s fiction or non-fiction—about this time in high school when you asked an old friend to be your best friend again.

The asking, “Hey, do you want to be my best friend again?” is an action. You are doing something. You are asking. But if that’s all we get is the action, without explanation or context, then we as readers have no idea how to perceive that action. Are we happy about it? Are we disappointed? Is the act of asking consequential in any way? We don’t know. It’s just action for the sake of it.

What gives that action meaning is context.

And one way of providing context is through Explanation—which often shows up as backstory.

Notice how the meaning of this action changes when we precede it with context:

“We hadn’t talked all summer. Not since his mom died, and my parents’ got divorced. Not since he started smoking cigarettes and hanging out with the skater kids. Not since I had started playing video games more, a lot more, my mom said I was addicted, maybe I was coping with the divorce. Not since last year, sophomore year. We had both changed so much. But this year was a new year. So the very first day of Junior year, before the bell rang for first period, I did it. I just walked right up to him and said, ‘Hey, do you want to be my best friend again?’”

~

The Explanation (the backstory, the context) preceding the action is what gives it meaning. And we are explicitly telling the reader what that meaning is—which isn’t the “only way” of creating meaning, it’s just a choice.

Description

Description is implied meaning.

If Explanation is explicit (you’re literally Explaining to the reader why something is, or is not, important), then Description is implicit.

This is the predominant quality of Classic Russian literature. If you’ve ever read Tolstoy, Nikolai Gogol, Anton Chekov, etc., then you know… the Russians (especially in classical literature) don’t “tell” you very much. They describe the character, the situation, and let you (the reader) infer the meaning on your own.

It’s worth noting that Description is the hardest “choice” to execute well, as a writer. And it is also the choice that asks the most of the reader. It’s significantly easier (as a writer, and for the reader) to just say, “So that’s why I was sad—because my parents got divorced,” rather than describing a scene in which that sadness, and what caused it, has to be inferred.

Sticking with our high-school-best-friend example, notice what happens when we swap all of the Explanation with Description:

“The summer was hot and long. His parents house had a For Sale sign in front. When I’d drive by, I’d stare at the rickety porch we used to sit on and just talk, talk for hours, Mountain Dews in our hands. One of those days, when a moving truck was outside, and parked behind it was a van with a logo on the side that said Naperville Foster Care, I walked up to that porch. A pile of half-smoked cigarettes sat in the corner, where we used to sit as kids. Inside the door, I could see the movers packing boxes, and he was just standing there, holding onto his backpack, the only thing he had left. We nodded at each other and that was about it. Then he followed the movers out, they locked the door, and the lady in a uniform with the same logo on it, Naperville Foster Care, had him sign something on a clipboard before opening the sliding door to the van, letting him in, before driving off. I just stood there, watching. We had both changed so much. But this year was a new year. So the very first day of Junior year, before the bell rang for first period, I did it. I just walked right up to him and said, ‘Hey, do you want to be my best friend again?’”

~

Notice how the story ends up landing in the same place, at the same action, but the road we took to get there is completely different.

Again, it’s not that Explanation is better than Description, or Description is better than Explanation. They’re just two different colors, two different moves on the chess board, pick your analogy.

We can think of “style” then as the deliberate choice a writer makes, in any given moment, any given sentence or paragraph, and the degree to which they want to give the reader explicit context or implicit context (or some combination).

Action

Action is movement.

The reason I like thinking of Action as movement is because if we unbundle the word “action” then what we find are two distinct groups of actions:

• Weak Actions: A weak action is something that “happens” but doesn’t actually move the story forward in any meaningful way. For example, “I took a step forward. I picked up the handheld mirror. I looked at myself. I stared, long and hard. Then I put the mirror back down.” Technically, these are actions. And technically, we could potentially increase the meaning of these simple, weak actions by adding Explanation or Description. But all in all, these are weak actions. Not much happens, in the sense that the story isn’t taking leaps forward.

• Strong Actions: A strong action is something that “happens” and is consequential. It reveals something about the character and/or moves the plot of the story forward. For example, “I picked up the handheld mirror, looked at myself, and then threw it across the room. I didn’t see her walk in, and the mirror grazed her left cheek. Then the mirror exploded against the back wall, glass shattering into a million pieces, some of which ricocheting into her hair and eyes.” Notice how each action is consequential. And it’s “the consequences” that give it meaning.

In college, my creative writing teachers used to call this the Rate of Revelation: the speed at which you reveal new information to the reader. This idea can be applied to any of the 4 pieces in this writing framework, EDAN, but it is most easily recognized in Action.

You do not want “action for the sake of action.”

You want actions that lead to consequences.

It’s also worth pointing out that Action, by itself, holds very little value.

Action is probably the weakest choice of the 4—EDAN—because its value relies on its relationship to the other pieces on the chess board. For example, the action of “crashing a car,” despite it being a strong and consequential action, has opaque meaning. What are the consequences of crashing this car? Are we worried for the main character? Or are we actually cheering them on—was crashing this car a moment of redemption?

The action itself is not enough.

We need to know how to perceive the action (with context, implicit or explicit), which is why Action is almost always best when paired with some form of Explanation or Description.

Narration

Narration is point of view.

In 1st-person fiction, the narrator is the main character. In 3rd-person fiction, the narrator is usually oscillates between omniscient and the close-3rd narration of a character’s inner experience.

Either way, Narration can be best thought of as the author’s and/or character’s point of view of the world and their coinciding beliefs. This is typically when we see the author’s head peek out from behind the curtain.

Sticking with our high-school-best-friend example, notice what happens when we add in some Narration:

“We hadn’t talked all summer. Not since his mom died, and my parents’ got divorced—and that’s the thing about divorce is it’s selfish because it hurts the people around you more than it hurts the people getting divorced. Not since he started smoking cigarettes and hanging out with the skater kids. Not since I had started playing video games more, a lot more, my mom said I was addicted, maybe I was coping. Not since last year, sophomore year. We had both changed so much. But this year was a new year. So the very first day of Junior year, before the bell rang for first period, I did it. I just walked right up to him and said, ‘Hey, do you want to be my best friend again?’”

~

The bolded sentence above is Narration.

It’s not Explanation in the sense that it’s not really backstory. And it’s not Description because it’s not really describing anything. And it’s not Action because there’s no movement, nothing is happening. So what is it? It’s the Narrator’s point of view. It’s an opinion about the way they see the world:

“…and that’s the thing about divorce is it’s selfish because it hurts the people around you more than it hurts the people getting divorced.”

Narration is a powerful mechanism for using stories to give commentary on specific themes. However, it’s also a very easy mechanism to overuse. If you tell the reader, “Here’s exactly what I think about what’s going on,” over and over again, then you remove all room for interpretation. You’re telling the reader how to feel without giving them the opportunity to infer meaning for themselves.

Writing Is Like Chess

This is an analogy I plan on writing more about (separately), but just to touch on it quickly here:

Writing is like chess. If you ask me, “What’s the best way to play chess?” then where do I even begin? There are infinite ways to play the game of chess, infinite moves on the chessboard, and infinite moves-in-reaction-to-your-moves, and so on. There is no one right way to play chess.

Now, are there better moves than others? Yes, of course. Chess is a game of decision trees: when I do this, you should do that. But even still, in almost every scenario, there will be multiple right answers. And more importantly, depending on the way you prefer to play, there will be different right answers for you compared to the right answers for me—depending on whether you prefer to play more defensively, or aggressively, and so on.

Writing is the same sort of game.

There is no one right way to write a book, or an essay, or a short story, or even a paragraph or sentence. There are infinite options, as well as multiple different right answers depending on the style of writing you want to produce.

Which is why I find the EDAN framework so helpful.

Too often, I see writers obsess over the “right” way to write. Which is unproductive. That’s like asking which is correct: moving one pawn or another pawn, using your bishop or using your knight. None of these choices, in and of themselves, is right or wrong. They are all just different options that sit on a spectrum of “more effective” and “less effective” relative to all the other pieces and options on the chessboard. Context matters.

So, what does this have to do with writing?

The first takeaway here should be that in order to learn how to produce great writing, you must first unbundle the term “great writing” and try to identify the individual parts that create the sum you desire (”a great piece of writing”).

I have isolated these parts here for you with the EDAN framework:

• Explanation

• Description

• Action

• Narration

The second takeaway should be that each of these different pieces hold different utility—the same way a bishop can only move diagonally, a knight can only move in L-shaped patterns, a rook can only move forwards, backwards, and laterally from side to side, and so on. But each piece’s utility is only maximized when considered in the context of what else is happening on the chessboard (or relative to what else is being said in a piece of writing).

• Explanation gives explicit context.

• Description gives implicit meaning.

• Action gives movement.

• Narration gives perspective and point of view.

Which means the advanced version of this framework is understanding each individual piece’s utility, and then finding unique combinations to maximize that utility by pairing pieces together—across a chapter, in a paragraph, or even in each individual sentence.

Let’s walk through a few different combinations:

Descriptive Explanation

Descriptive Explanation is when you add descriptive elements to explanation and backstory. Think of the Explanation as “what you need to know,” and the Description as “the way I tell you.”

For example, here’s our original Explanation example:

“We hadn’t talked all summer. Not since his mom died, and my parents’ got divorced. Not since he started smoking cigarettes and hanging out with the skater kids. Not since I had started playing video games more, a lot more, my mom said I was addicted, maybe I was coping with the divorce. Not since last year, sophomore year. We had both changed so much. But this year was a new year. So the very first day of Junior year, before the bell rang for first period, I did it. I just walked right up to him and said, ‘Hey, do you want to be my best friend again?’”

And here’s the same Explanation but with each sentence adding in Description:

“We hadn’t talked all summer, it was a brutally hot summer. Not since his wrinkly-faced mom died, and my bickering parents’ got divorced in the most dramatic way possible, my dad taking his wedding ring off and flushing it down the toilet. Not since he started smoking those Menthol cigarettes and hanging out with the skater kids who had long hair and wore hemp-rope necklaces. Not since I had started playing video games more, specifically Final Fantasy, a lot more, my mom said I was addicted, maybe I was coping with the divorce. Not since last year, sophomore year. We had both changed so much, like he’d even gotten one of his ears pierced and I had started wearing baggy pants and oversized T-shirts. But this year was a new year. So the very first day of Junior year, my backpack heavy with all my new textbooks and empty notepads, before the bell rang that loud and annoying sound for first period, I did it. I just swaggered right up to him and said, my voice cracking, ‘Hey, do you want to be my best friend again?’”

~

Notice how the Explanation is still what’s sitting in the spotlight, it’s the predominant thing we’re trying to achieve with this section.

But it comes to life when description is added throughout the explanation.

You should think of this like a volume knob you can turn up and down, all the way down to the sentence and word level. For a single sentence of Explanation, you could have no description (0), you could have some description (3), you could have lots of description (7), or you could have an overwhelming amount of description (10).

Descriptive Action

You can do the same thing by combining Description and Action.

Broadly speaking, “Explanation Action” isn’t a great pairing because these two pieces accomplish very different things. Imagine you’re watching a fight scene (Action), and then halfway through the fight scene everyone pauses and the narrator Explains to you what’s happening and why it’s important. Kinda ruins the momentum of the moment. (That’s not to say you can’t make it work. You could make the pause dramatic, and have the main character address the reader/audience directly, and make the Explanation intentionally dysfunctional. Etc.)

Descriptive Action is a much more effective pairing.

• Sometimes this means taking a passage that is primarily Description, and adding Action.

• And sometimes this means taking a passage that is primarily Action, and adding Description.

For example, here’s a passage of Descriptive Action:

“His parents house had a For Sale sign in front. I drove there in my beater Honda, the front right wheel almost flat, thwapping as I pulled into the driveway. I stared at the rickety porch that we used to sit on and just talk, talk for hours, Mountain Dews in our hands. The porch had faded in color, used to be white but now the paint was chipped and worn from the weather and I could see the greyish wood underneath. A pile of half-smoked cigarettes, the thin kind, sat in the corner, where we used to sit as kids. I stomped on the pile of cigarettes and then walked my ashy shoes inside. I saw the movers packing boxes, and then I saw him. He was just standing there, holding onto his backpack, that red backpack he’d had since middle school. And even though we hadn’t talked all summer, without even thinking about it, I walked right up to him and gave him a hug.”

~

What are the Actions in this passage?

• Driving to the house

• Staring at the porch

• Stomping on the pile of cigarettes

• Giving the friend a hug

These are the Actions that create movement in the passage.

But each Action gets amplified when paired with Description. Not only can we “see” each Action more clearly, but we can also infer its meaning.

Narration Explanation

A less conventional pairing would be Narration Explanation, where you are Explaining something to the reader (providing context/backstory), but also inserting the narrator’s point of view.

For example, here’s a passage of Narration Explanation:

*I am going to underline the pieces of Narration.

“We hadn’t talked all summer. Not since his mom died, and my parents’ got divorced—and that’s the thing about divorce is it always hurts the people around you. Not since he started smoking cigarettes and hanging out with the skater kids. Not since I had started playing video games more, a lot more, my mom said I was addicted, maybe I was coping with the divorce. I probably was, because coping is one of those things everyone else knows you’re doing except you. We had both changed so much. But this year was a new year. So the very first day of Junior year, before the bell rang for first period, I did it. I just walked right up to him and said, ‘Hey, do you want to be my best friend again?’”

~

Notice, these little pieces of Narration gives us some insight into how this narrator sees the world, their opinions, their beliefs, etc. And that Narration can be sprinkled into an Explanation.

Combining EDAN At The Sentence-Level

Now, can we take this one step further?

You bet we can.

In a single sentence, you could theoretically use all 4 pieces:

• Explanation: I will bold this.

• Description: I will italicize this.

• Action: I will leave this as plain text.

• Narration: I will underline this.

Here’s an example of a sentence using all 4 pieces of EDAN:

“My parents divorce and the way it was ruining my idea of marriage is probably why I reached onto my overpriced mahogany bedside table, grabbed my brand new baby blue iPhone, picked it up, looked at myself in the black mirror of its screen hungry for my attention, saw my girlfriend text me a heart emoji, I knew she was cheating on me, at least I had my suspicions, and chucked my phone across the room, its innards exploding against the back wall, which is the wrong way to deal with your problems, breaking things, I know, but I didn’t care.

~

Notice how much is happening!

Now, whether you “like” what I’ve written here is not is besides the point. Maybe you read the above passage and thought, “Wow, that’s really well-written.” Or maybe you thought, “I hate how that’s written.” Or maybe you thought, “It’s nice, but I would have liked more Explanation.” Or maybe, “It’s nice, but I would have liked more Description of the room.” And so on.

This is what I mean when I say writing is an infinite game—with infinite combinations, none of which are right or wrong.

But an effective place to start, when trying to learn how to “write great things,” is to understand the pieces at your disposal, what each piece does by itself, and how each piece gets maximized when combined with other pieces.

If you want a fun writing exercise…

The next time you sit down to read something, see if you can identify which of the 4 EDAN pieces are being used in every single sentence.

(This exercise will make your brain hurt—in the best way. And help you start to see how great writing is assembled down at the sentence-level.)

The way I like annotating this is:

• (E) Next to any Explanation

• (D) Next to any Description

• (A) Next to any Action

• (N) Next to any Narration

Some sentences and phrases you may find are multiple of these pieces smashed together. That’s OK. It’s worth sitting there for a few seconds and letting your brain think through the different combinations.

Because again, there are multiple right answers.

Dear Writer,

One of the most common questions I get asked these days is:

“Cole, how is AI going to change things for writers?”

And the answer for each Writer Career Path is somewhere between “marginally” and “exponentially.”

Will AI render the craft of writing obsolete over the next decade? Of course not. In fact, the counterargument I often present pessimists is, “What skill do you need to have in order to use any of these consumer AI models and platforms? In order to prompt you have to… that’s right… you have to know how to write.”

Writing just might be (if it’s not already) the single most valuable skill of the next few decades.

The next analogy I like presenting is to look at previous innovations in meaningful industries:

• The Industrial Revolution and the invention of the tractor didn’t destroy farming. It scaled farmers exponentially, and led to the globalization of trade.

• Photoshop didn’t destroy the animation, sketching, drawing, or design trade. It lowered the barrier to entry and allowed exponentially more people to become professional designers. (And then Canva did the same thing, lowering the barrier to entry further, allowing non-designers to become reasonably proficient.)

• Instagram didn’t destroy the photography business. It lowered the barrier to entry and allowed exponentially more people to become photographers.

The list goes on.

All throughout history, new technologies have had net-positive effects on society. These technologies reduce costs, democratize access, increase competition, and accelerate innovation. Now, have some industries declined, or been rendered irrelevant in the process? Of course. But these losses sit in a broader context of an abundance of opportunity.

And if you don’t believe or agree with me, let’s just invert the question:

• Would you trade access to the Internet (digital paper) to keep the once-booming physical paper industry? Of course not.

• Would you trade modern pharmaceuticals to maintain the sales of outdated, now-terrifying medical devices from the 1900s? Of course not.

• Would you trade your iPhone for a rotary phone because you don’t want the rotary phone companies to go out of business? Of course not.

Over and over again, innovation doesn’t destroy industries. It changes them, augments them, and provides opportunity for people to develop new skills. And more times than not, these new skills lead to increased productivity, less work (or less “taxing” work, as seen with the decrease of blue collar jobs and the increase of white collar jobs), and more income—for both these new businesses, as well as their employees and shareholders.

Now, the big counter-argument here is that “AI is going to be different.”

And I agree, yes, it will.

But I also disagree, and no, it won’t.

I can’t speak for all industries. However, I’ve been writing on the Internet for over 15 years now. And, without patting myself on the back too hard, I have been right about every major writing trend of the past two decades.

• I started writing online in 2007, back when the masses called “blogging a fad.”

• I started self-publishing on Amazon in 2013, back when the masses called “self-publishing a scam.”

• I started a ghostwriting business in 2016, back when the masses called ghostwriting “unethical.”

• I started a paid newsletter business in 2017, back before Substack raised hundreds of millions of dollars, pioneered the category, and started educating journalists on how much more money they could earn starting their own 1-person publication (aka: a paid newsletter with subscription revenue).

• I started a cohort-based writing program in the pandemic, when the masses thought the sky was caving in, opportunities didn’t exist anymore, and society was going to collapse.

• Etc.

Now, admittedly, AI is a completely new and different technology than we’ve ever known. So despite having been “right” many times in the past, I have no idea what’s going to happen in the future—especially the further out we project.

My goal here is simply to give you my best guess on how I see AI augmenting each of the major Writer Career Paths for the next decade:

1. Writer Career Path #1: Literary Writer

2. Writer Career Path #2: Genre Fiction Writer

3. Writer Career Path #3: Non-Fiction Writer

4. Writer Career Path #4: Newsletter Writer

5. Writer Career Path #5: Content Writer

6. Writer Career Path #6: Ghostwriter

7. Writer Career Path #7: Copywriter

8. Writer Career Path #8: Writerpreneur

9. Writer Career Path #9: Category Copywriter

Let’s dive in.

Writer Career Path #1: Literary Writer

Of all the Writer Career Paths, literary writing is likely to be the least affected by AI.

In fact, I can imagine a world where the entire purpose of the literature genre is to produce work that is AI-Free. Book awards will require author confirmation they did not use AI in the writing process. Curated best-selling lists (like the New York Times or The Wall Street Journal) for literary novels will require the same. And much of the status associated with being a Literary Writer won’t just be the quality of your work, but the fact you didn’t use AI to produce it.

Other things I anticipate happening:

• Authors adding badges or watermarks to their novel covers proclaiming their work is AI-Free (marketing to a specific type of reader).

• AI-Free writing & publishing conferences.

• An increase in demand for analog, legacy writer experiences: writing retreats, book clubs, in-person workshops, etc.

A fascinating (and favorite) example of this is George Saunders’ paid newsletter on Substack, Story Club. This newsletter is the complete opposite of the AI-everything narrative that seems to be devouring everyone’s social algorithms. And yet, it’s the most popular Literature paid newsletter on the platform with thousands of paying subscribers and one of the most engaged comments sections I’ve ever seen.

Clearly, despite all the innovation forward since the days of Tolstoy, Dostoyevsky, and Nabokov, there is still significant demand for “the good old days” of literary writing. And I believe, as AI accelerates other Writer Career Paths, it will actually have an inverse effect on literature. AI will make literary readers even more committed to the genre. And AI will challenge literary writers to test their skills against these new technologies—the same way Grandmaster chess players do, despite supercomputers having the capacity to perform the same skills, better and faster.

Another good analogy here would be classical music. New innovations like modern recording equipment, Auto-tune, and now AI, have certainly augmented the music industry—and shifted customer demand to newer, faster-growing categories (punk rock, trap, EDM, etc.). But these innovations have not “killed” orchestras or most parents’ desire for their child to play a musical instrument.

Literature will follow a similar trajectory.

Writer Career Path #2: Genre Fiction Writer

AI and its impact on genre fiction is most likely going to exist on a very wide spectrum.

• On one end, you will have something similar to the AI-Free movement we will see in literature.

• In the lower-middle, you will have fiction writers who use AI for brainstorming, worldbuilding, feedback on their writing, editing, etc., but who still prefer to do most of the “creative work” and writing themselves.

• In the upper-middle, you will have fiction writers who use AI not just for these same tasks, but to also build systems for themselves—acting as a 1-person publishing company orchestrating an army of agents. And in the process, many of these fiction writers will inevitably lean on AI to take on more and more of the writing itself.

• And on the other side of the spectrum, you will have savvy digital marketers disguised as fiction writers using AI to spam-create as many stories as they can, in specific genres, to dominate search algorithms and brute-force victory through volume.

So, what is AI’s impact going to be on the world of genre fiction—and the career path of becoming a successful Genre Fiction Writer?

Well, it depends on what kind of writer you want to be, what outcome you’re trying to optimize for (is it money? is it creative freedom? is it leverage?) and how you want to play the game—because there will be multiple “right answers.”

In addition, I believe AI-forward Genre Fiction Writers will likely be the first ones to build the bridge between genre fiction and the inevitable rise of a new AI-powered Hollywood.

Film studios have already started pivoting away from taking risks on brand new screenplays from unknown writers, and started prioritizing buying up best-selling novels from writers with existing audiences and then adapting these stories for film and television. And it’s reasonable to assume this trend will continue, faster and at a fraction of the cost, with AI video-generation platforms. Major film studios already act as venture capital firms—each film, a “startup.” So once the majors—Universal Pictures, Paramount, Warner Bros., Disney, Sony, Amazon, etc.—harness AI video platforms that can create entire shows and films in 1/100th the time for 1/100th their typical investment, the entire game will be to buy up as much IP as possible. Each major film studio will have their own AI video model (or they will all license the most powerful one). Each will spend billions and billions of dollars buying up as many “proven” novels and short stories as possible. And they will feed those novels into their AI video models to produce 100x more movies and TV shows for consumers to choose from.

This mega-trend is something I think about a lot—and makes me very excited for Genre Fiction Writers.

There will be a ton of money chasing proven, high-performing fiction stories.

Writer Career Path #3: Non-Fiction Writer

Non-fiction writing is likely to be one of the Writer Career Paths most impacted by AI.

Because the truth is, in the context of writing non-fiction business, finance, or life advice books, the vast majority of “authors” care very little about the craft of writing. These are founders, CEOs, speakers, influencers, celebrities… people who want to be seen as an “industry authority” more than they want to be seen as a writer. And so, for them, writing a book is more of a means to an end than it is a career path or calling. (Not that there’s anything wrong with that.)

That said, yes, there is a small percentage of Non-Fiction Writers who don’t fit this bill. I’m guessing writers like Nassim Nicholas Taleb, Ray Dalio, Elizabeth Gilbert, Margaret Atwood, etc., couldn’t care less whether their next book leads to an increase in speaking gigs or lead flow for their business. These writers enjoy the craft of writing, see it as a vehicle for crystallizing their own thinking, and derive significant joy (or status—nothing wrong with that either) from sharing their clarified insights and stories with the world. For them, the journey is the destination.

Will AI render these types of committed writers irrelevant? Of course not.

In fact, I would argue it will have the opposite effect.

Since publishing a non-fiction book is the new “business card,” AI is going to lead to a dramatic increase in the number of business owners, startup founders, executives, motivational speakers, etc., who publish books. And these books will be filled with commoditized insights. They won’t say anything new. They’ll simply repeat conventional wisdom, sandwiched between stories personal to the author—which, ironically, will accelerate the deterioration of publishing non-fiction books as an effective “positioning strategy.”

But… as AI increases the supply of business owners, influencers, and celebrities who “write books,” the inverse effect will be an increase in demand for non-commoditized insights. From innovative, credible thinkers, non-fiction book buyers will care less about “how much” AI was used in the creation of the book and more about how different, unique, and valuable the insights are inside.

Here’s the spectrum of AI usage I can imagine unfolding in the world of non-fiction book writing:

• On one end, you will have the literary equivalent: creative non-fiction writers and memoirists who essentially write “true novels.” These writers lean heavily, almost entirely on personal stories—maybe the hardest and least likely thing for AI to “automate,” unless given training data on everything you’ve experienced in your life to-date.

• One notch up, you will have Nobel prize-winning academics who, at most, use AI to assist with deep research. But these writers will still spend a considerable amount of time manually reading, interviewing, experimenting, synthesizing their hypotheses and takeaways, and then crystallizing their insights in prose form.

• Next, you will have Hybrid Non-Fiction Writers: part writer, part marketer and AI maestro. I can imagine writers like Ryan Holiday falling into this category—people who are care deeply about the craft of non-fiction writing, but who are also business savvy and eager to leverage these new technologies to produce more high-quality work, faster.

• Next, you will have the vast majority of business owners, founders, executives, investors, influencers, and celebrities. These people just want a book with their name on it—and oftentimes hire ghostwriters (or soon to be AI Ghostwriters) to help them achieve that goal as quickly as possible. There is nothing wrong with wanting to “publish a book” as a marketing and positioning strategy. It’s just worth acknowledging that as AI makes this easier, at lower and lower costs, this “marketing trick” will experience diminishing returns.

• And lastly, you will have AI-spammers: savvy digital marketers who use these new technologies and tools to discover pockets of demand on Amazon for hyper-specific keywords, and then use AI to pump out self-published books to capture that demand at lightning speed. This is already Amazon’s biggest problem, and as AI models improve, and as more AI-powered publishing tools get created, this problem will only increase at an exponential rate.

Separately, AI will have a massive impact on the different business models non-fiction writers use to monetize their “thinking.”

If you think about it, what is a “book?”

A book is just a long-form training prompt for human beings. It’s a bunch of clarified insights stuck inside one person’s brain, put down on paper (translation: given leverage), with the hope of those insights landing in lots of other people’s brains—and successfully changing those people’s behavior.

• A finance expert writes a book about finance to help other people solve financial problems in their life, business, etc.

• A nutritionist writes a book about nutrition to help other people solve health problems in their life.

• A therapist writes a book about marriage counseling to help other people solve problems in their own marriages.

• Etc.

Now, there is a subset of non-fiction that is “entertainment.” This could be memoirists like David Sedaris who write essays and short stories based on real-life events and experiences. But this could also be academics, columnists, or just everyday “thinkers” who write books about true topics—history, economics, life advice, etc.—that are interesting, maybe even entertaining, but do not change your behavior as a reader. Authors like Malcolm Gladwell come to mind here. When you read a Malcolm Gladwell book, you learn a bunch of dinner-party facts that are both interesting and, at times, entertaining. But at the end of the book, you aren’t really supposed to “do” anything with that information.

The vast majority of non-fiction books are, fundamentally, intended to change reader behavior. They teach you “how” to do something—or “why” something is the way that it is (with the hopes of your newfound perspective, in some way, changing the way you live your life). And so, pure entertainment aside, that means most non-fiction books are really just long-form prompts for human behavior.

So, if your goal is to help people with your writing—to give leverage to your unique insights, “scale” your learnings into the brains of lots and lots of other people, and successfully change their behavior—then it’s worth considering a book might no longer be the most effective vehicle to accomplish your goal.

Because here’s what happens:

• You write a non-fiction book, sharing your insights.

• Some people read it (not “all people,” just some).

• Only a percentage of those people end up reading the entire book.

• And only a percentage of that percentage actually implement the things they learn from your book.

Now consider, if instead of “publishing a book,” you take all your same “How To” insights and leverage them with AI:

• You write a long-form mega-prompt (which is really no different than writing “a book”—because a book is just a mega-prompt for humans).

• You wrap that mega-prompt inside a digital education product (an online course, for example) or a SaaS wrapper (a consumer-friendly digital platform or tool).

• Now, instead of “reading” your book and manually putting your insights into practice, customers can “use” your prompt and automatically implement your insights into whatever action you are helping them take, or task you are helping them “do.”

• And because your insights have successfully automated an “action,” or increased the reliability of an action being executed successfully, you end up helping a greater percentage of people successfully change their behavior—and unlock the outcomes of these new behaviors.

But it doesn’t stop there.

With all that in mind, consider how this new way of seeing non-fiction knowledge also changes the business model of monetizing “How To” information.

Selling books is a challenging business model. “Books” as a category are stuck in the $10-$50 per copy range (depending on format: eBook, paperback, hardcover, exclusive leather-bound, etc.), with a pretty rock-hard ceiling at $100 per copy—and that’s for a super-ding-dong “Collector’s Edition.” On top of that, books are stand-alone products. You buy one, and then you’re done. And only a small subset of customers become repeat buyers, usually buying additional copies as gifts.

• Books have very little pricing power

• And books have no recurring revenue

Which is why the vast majority of non-fiction authors (even the most successful ones, like James Clear, Jen Sincero, Ryan Holiday, etc.) monetize in lots of other ways besides just the sale of their books. They sell courses and workbooks and journals and merchandise; they get paid to speak at events; they hold workshops; they get hired as consultants; and so on.

All AI is going to do is add more (and more lucrative) monetization options.

For example, why write a stand-alone $20 book when you could…

• Take the same information, turn it into a mega-prompt bundled inside an online course, and sell it for $350?

• Or take the same information, wrap it in SaaS, and charge $20 per month to use it?

• Or take the same information, break it apart into smaller chunks, and drip it out each week as a paid newsletter for $20 per month or $200 per year?

• Or take the same information and sell it as a B2B consulting roadmap for $20,000?

• Or take the same information and turn it into a PDF of differentiated IP and training data for a specialized AI model, and sell that PDF of differentiated insights to a huge company for $200,000?

The point is, AI is going to unlock so many more, and more lucrative, revenue streams for “differentiated thinkers” to monetize their insights.

And as these “thinkers” start to wake up to the-value-of-their-value, it’s not unreasonable to consider that in the age of AI, commodity non-fiction books are going to increase exponentially (easy to write, cheap to produce), whereas non-commodity, highly differentiated non-fiction thinkers will choose not to write books at all.

Writer Career Path #4: Newsletter Writer

Newsletter Writers will likely follow a similar trajectory as Non-Fiction Writers.

AI is going to make it easier and cheaper for everyday people to:

• Launch (free and paid) newsletters

• Write content

• And “scale” that content with more content (newsletters being chopped into Tweets and LinkedIn posts and even AI-generated Instagram Reels and TikTok videos).

Now, I actually don’t think this is a bad thing—or even all that different from the way the world is right now. In every industry, on every platform, “content” is already incredibly saturated. And yet, new and interesting creators emerge every single day. People brand new to long-established platforms create new accounts and end up building meaningful audiences. And for years, the masses have been saying “email is dead”—yet, every year, more people launch newsletters, and more people make money from email.

So all AI is going to do is take these existing, escalating trends, and make them move faster.

That said, there are a couple things AI will change for Newsletter Writers:

First, AI is going to add leverage. This is true for every Writer Career Path, but I’ll stick with Newsletter Writers for now. There are a lot of manual tasks involved in publishing a weekly (or whatever cadence) newsletter. And we aren’t far from AI agents being capable of doing 80% of those tasks: uploading drafts to your preferred email platform; evaluating weekly data; feeding that data back into a spreadsheet; analyzing that data and coming to iterative conclusions; etc. As a result, there will be newsletter writers capable of producing millions, maybe even tens of millions, maybe even hundreds of millions of dollars in subscription revenue, with zero employees and almost no costs—because they will have significantly more leverage.

Second, AI is going to give rise to a tidal wave of niche-specific newsletters. It will become very easy to spin up a weekly newsletter in any niche that exists and have AI “run” it autonomously. Obviously, at this point, your “goal” as a writer is no longer to do the writing, but to use writing as a means to achieve some end. As a result, we’ll start to see more savvy newsletter writers act as 1-person publishing houses—orchestrating an army of AI agents to operate hundreds, maybe even thousands of ultra-niche newsletters (the same way savvy digital marketers do with ultra-niche self-published books on Amazon).

Third, AI may lead to a new sub-category of paid newsletters (or new sub-category of all “content”), which is Personalized Newsletters. In a not-so-distant future, I can imagine AI unlocking the ability for every single person on your email list to receive a “different” version of that week’s newsletter—depending on their preferences, background, and beliefs. A simple example would be AI knowing if the subscriber is female, and to change the examples in that week’s newsletter to be female-oriented—whereas if the subscriber is male, to change the examples to be more male-oriented. Or, more specifically, AI might know one female subscriber is a Democrat whereas another female subscriber is a Republican, and to tailor the examples, stories, or perspectives in that newsletter accordingly. Obviously, there are some terrifying implications of this sort of echo-chamber technology, but it’s “possible” and likely not far away.

And fourth, since paid newsletters are significantly more profitable and scalable than writing non-fiction books, more non-fiction writers are going to pursue this business model instead. Again, a high-quality non-fiction book usually takes 1-3 years to write. Then, when it’s done, the most you can sell it for is maybe $30. On top of that, customers give you money once, and that’s it—very few repeat purchases, and no recurring revenue. But if you were to take all the same content, the exact same words, but call it a “paid newsletter” and drip chapters (or pieces of chapters) out weekly, suddenly you can charge $20+ per month (or $200+ per year), generate subscription revenue (making your business more predictable and defensible), and “get paid up-front” to write the book you were already going to write. And so we will see more of these writers choose to start paid newsletters instead of writing books—and then use AI to scale their 1-person publishing businesses.

Writer Career Path #5: Content Writer

This is another career path that is going to be heavily impacted by AI.

Remember, most companies and business owners use the term “content writing” as an umbrella term that encompasses all writing. But that’s not true. Sales copywriting—assets that sell and persuade customers—is not “content writing.” And ghostwriting—thought leadership content co-created with founders, executives, investors, etc.—is also not “content writing.”

Generally speaking, “content writing” means creating educational, somewhat commoditized content on behalf of a company.

This could be:

• SEO blog posts

• Website content

• Technical walkthroughs and FAQs

• Company announcements and press releases

• Etc.

And the truth is, all of these content types will be the first to get eaten by AI. They are the easiest to write, easiest to automate, and easiest to “scale” with agents.

Which means this Writer Career Path is going to very quickly transform from being a “writing” role into an “AI management role.”

And this same trend is going to be true for lots of other jobs in lots of other industries as well: Independent Contributors becoming AI Managers.

The future of Content Writing is not going to be you, sitting by yourself with a cup of coffee, getting paid to manually write thoughtful SEO blog posts about life insurance, drop-shipping, or liposuction.

Instead, the Content Writing career path is going to become a fiercely competitive game of leverage. Companies will want to know how much “content” you can produce as an individual using AI—and will make decisions on who to hire, employ, and keep on staff based on volume more than quality (since, using AI, quality will become generally commoditized).

Which means there will really only be 2 types of Content Writers:

• The 10x Content Writer: Someone who doesn’t just use AI to produce ten times more volume than all the other content writers, but also develops their own unique prompts (aka: intellectual property) to produce differentiated and valuable content for a specific industry or type of company. These 10x Content Writers will earn a massive premium on their skills. Everyone else will struggle to find jobs and be stuck in a race to the bottom on Upwork and Fiverr.

• The AI Agent Orchestrator: The other type of Content Writer will ascend out of being a high-leverage Individual Contributor and into an AI Manager responsible for overseeing agents. Instead of doing the writing, or even using AI to do the writing, they will simply build and oversee the systems that use AI to do the writing.

All that said, it’s important to remember that Content Writing as an industry isn’t going to “die” as a result of AI. In fact, quite the opposite. AI is going to exponentially increase the number of companies that want to produce content. It will just appear as though opportunities are vanishing because a small number of AI-leveraged Content Writers will be able to take on ten times as many clients.

So, this Career Path isn’t going anywhere. It’s just changing.

And if you lean into it, and learn how to use AI, there’s no reason why you can’t be the one to capitalize.

Writer Career Path #6: Ghostwriter

In many ways, AI is going to change Ghostwriting the same way it’s going to change Content Writing.

• There will be 10x Ghostwriters—Individual Contributors who leverage AI to take on many more clients than the average ghostwriter.

• And there will be AI Agent Orchestrators—Ghostwriters turned Managers who develop systems that allow them to ascend out of the work and become solely responsible for quality control. (For example, I anticipate a rise in 1-Person Ghostwriting Agencies. No employees, just an army of agents.)

But here’s the nuance a lot of writers miss:

The fundamental reason why business owners hire ghostwriters in the first place is because they lack confidence in their own ideas. I know because I’ve ghostwritten for hundreds of incredibly accomplished CEOs, billionaire Silicon Valley founders, investors, Grammy-winning musicians, Olympic athletes, you name it. And the vast majority, nearly all of them, in some way or another needed help not just crystallizing their thinking but feeling comfortable sharing their thoughts, insights, stories, and perspectives online for everyone to read and judge.

So, will AI models and agents be able to produce similar quality work? Yes.

Could these business owners, founders, executives just “talk” to ChatGPT or Claude and clarify their thinking on their own? Of course.

But do they? No.

Because they don’t have the time to do it themselves, and more importantly, because even the most successful people in the world have a hard time getting out of their own way.

They are hiring you to manage them.

Which is why I firmly believe ghostwriting will be one of the most defensible Career Paths for writers over the next few decades.

For the following reasons:

• Reason #1: Demand for building a personal brand is only going up. Every single business owner, influencer, podcaster, coach, YouTuber, Silicon Valley founder, investor, and author is realizing they need to build a personal brand. Why? Because having a strong digital presence and a growing audience makes everything easier. It gives you leverage. It means you can acquire customers for free (and not have to spend any money on ads). It makes your career more lucrative and defensible. The list goes on. The problem is, all these people have a shortage of time. And so the only way to “scale themselves” online and build their personal brand is by working with a ghostwriter. Which means as long as demand for personal branding continues to goes up, so will demand for ghostwriting.

• Reason #2: The entire point of ghostwriting is to create “differentiated” content. This is the only way to build a successful personal brand. You can’t stand out by publishing commoditized insights the way companies do with SEO blog posts. It just doesn’t work. So when a business owner hires a ghostwriter, they aren’t just hiring “a writer to write words.” They’re hiring a thinking partner. And the more successful the client, the more value they are going to place on the collaborative element of your work together.

• Reason #3: Writing is only a small piece of the value you provide as a Ghostwriter. In fact, a lot of the value lives in all the tasks that surround the writing: interviewing the client, asking thoughtful questions, being able to do your own research, being able to expand on the client’s ideas, managing the clients expectations, coaching them through their own faulty beliefs and irrational objections, etc. The highest-paid ghostwriters in the world aren’t “the best writers.” They’re proficient writers, but they get paid a premium because they’ve acquired all the other necessary skills to manage and work with these types of busy, successful people.

Writer Career Path #7: Copywriter

The impact AI is going to have on the Copywriter Career Path is going to be somewhere between Content Writing and Ghostwriting.

• Copywriting will be more defensible and lucrative than commoditized Content Writing.

• But I actually think it will be less defensible, and potentially less lucrative than Ghostwriting.

The reason is because copywriting is all about writing things that “sell”—primarily ads, emails, direct response landing pages, and video sales letter scripts. And these “sales” assets are much closer to commoditized content.

For example, how do you sell “weight loss?”

• You educate people on things that make them gain weight.

• You educate people on the bad things that will happen if they don’t lose weight.

• You educate people on the good things that will happen when they finally lose the weight.

• And you motivate people to take action by showing them how their life could be different—if you buy the solution you’re pitching to solve their problem.

It really doesn’t matter what kind of weight loss company you’re running or product you’re selling. The “way” you sell weight loss is pretty universal—making it somewhat commodity information.

Which is why 80% of copywriting jobs are going to follow the same trajectory as content writing jobs:

• 10x Copywriters: These will be Individual Contributors who use AI to create ten times as many ads as the average copywriter, but also learn how to use AI to produce new types of advertising creative. For example: creating video ads using AI-video generation platforms, or using low-code tools to produce beautifully designed ad graphics in a fraction of the time, for a fraction of the cost.

• AI Agent Orchestrators: Then there will be the Copywriters who ascend out of “doing the work” and into “managing the robots that do the work”—since the vast majority of ads will be able to be written by AI models trained on all the other ads that have worked for companies and products in the past.

Now, that said, I do believe the top 1% of Copywriters will actually fall into neither of these buckets.

This is where Copywriting and Ghostwriting differ. The world’s highest-paid ghostwriters are usually existing, successful authors and journalists—people like Mark Manson (who ghostwrote Will Smith’s memoir), or J.R. Moehringer, an American journalist who ghostwrote Prince Harry’s memoir. This is the peak of this career path, and these writers charge millions of dollars to ghostwrite books for celebrities, politicians, and high-profile CEOs.

But not tens of millions. And certainly not hundreds of millions.

Copywriting, on the other hand, is a lottery game. When played at the highest level, the world’s richest copywriters either build companies themselves OR get paid a percentage of the profits they deliver. These are the Tai Lopez’s of the world—entrepreneurs who master the art of creating differentiated, hypnotic ads and ad angles customers can’t help but pay attention to. And they generate hundreds of millions, sometimes even billions of dollars in revenue as a result.

These types of Copywriters aren’t going to be “replaced” by AI.

They’re going to leverage AI. They’re going to build teams that use AI. They’re going to capitalize on AI.

But it will be at their directive.

Writer Career Path #8: Writerpreneur

You should notice by now that AI is going to impact all the Writer Career Paths in similar ways, just with different path-specific nuances:

• AI is going to give writers more leverage.

• AI is going to increase a writer’s expected output.

• AI is going to lower the barrier to entry and increase baseline quality.

• AI is going to allow talented Individual Contributors to ascend to Agent Managers.

• AI is going to unlock more, and more lucrative monetization opportunities.

And all of these things are going to change the career path of being a Writerpreneur.

In fact, it’s already happening.

Soon, there will be two different types of Writerpreneurs:

• A Writerpreneur who sells digital education on “how to” do something.

• Or, a Writerpreneur who teaches people “how to use AI” to do something.

I’ll use myself as an example here.

I teach people how to start writing online with our cohort-based writing program, Ship 30 for 30. Sure, we also give people AI prompts, and provide some baseline AI education. But fundamentally, I am a writer teaching other people how to write. And I “make money” by packaging all my learnings into an online course for other people to use. I am monetizing “How To” do something.

But, another option, would be instead of teaching people how to start writing online, I could teach business owners “how to build an AI agent” to write online on their behalf. But this would be a very different type of education. I’d be talking a lot less about writing principles, and instead a lot more about AI frameworks, platforms, and systems.

So there’s an interesting divergence that is about to happen—across every form of digital education, in every industry.

Some people will specialize in teaching “skills,” and it will likely become a baseline expectation for them to include or speak to how AI can be used in conjunction with those skills to be successful, more efficient, more profitable, etc..

But other people will specialize in teaching “meta-skills”—how to train and leverage AI to accomplish a task instead. These customers will be less interested in learning “How To” do something themselves, and more interested in learning how to build an AI-powered system to do it for them.

My awareness of this mega-trend is half the reason why I started Write With AI. Because as much as I am a purist and feel strongly it’s important for people to learn the fundamentals of writing, I’m also aware that a large number of people just want to “skip to the answer” and have AI do it for them.

And I’d like to be able to serve both types of customers.

Which means, if you want to be a Writerpreneur, now is a good time to ask yourself:

“Do I want to teach people how to do something themselves? Or do I want to teach people meta-skills and how to use AI to do it for them?”

Both have plenty of potential. And education that has nothing to do with AI (like gardening, dating, or yoga) isn’t going anywhere.

They’re just different types of customers.

Writer Career Path #9: Category Copywriter

Lastly, how will AI impact the career path of being a Category Copywriter—aka a very expensive messaging consultant?

A lot, and not at all.

In this career path, AI is going to be less of a “replacement” and more of a brainiac assistant happy and willing to work on your behalf 24 hours per day, 7 days per week. It will be your researcher, capable of doing detailed market analysis. It will be your spreadsheet number cruncher, your presentation builder, your fact checker. Most of all, it will be your thinking partner.

Because the truth is, even if you trained an AI model on your own Category Copywriting principles and frameworks capable of doing everything you do, that’s still not why companies hire consultants. (This is something a lot of people don’t understand.) Companies don’t hire smart people to give them the answer. They hire smart people to give them conviction in an answer—and to stand by it no matter how many objections get thrown their way.

Because the truth is, no “message” in and of itself is perfect. There can be multiple right answers. Which means what a company is really buying (from you, the Category Copywriter) isn’t the perfect and only answer. What they’re buying is your individual taste: an answer you feel strongly is correct-enough, and when stress-tested by the executive team’s fears and questions and uncertainties, doesn’t break.

Now, will AI reach a level of intelligence where it can replace “human conviction?”

I actually think yes.

There will come a time when the world’s most successful companies trust AI models more than they do the taste of world-class writers, designers, and consultants.

But it’s important to understand society is going to have to undergo a massive rotation before this becomes conventional wisdom. Right now, we can barely trust robots to successfully perform 100% of an entry-level task—like answer customer support emails. And so, regardless of how smart these AI models become, however quickly, it’s still going to take society a good while to trust robots more than humans.

Especially when it comes to the entire messaging strategy of a multi-billion-dollar company.

Now Is The Greatest Time In History To Be A Writer

With all the above in mind, net-net, I believe now is the greatest time in history to be a writer.

Yes, AI will change what it means to be “a writer”—and it will change each individual Writer Career Path in different ways. But AI won’t destroy these career paths, replace writers, or render the craft of writing obsolete. In fact, quite the opposite. AI is going to be a brutal forcing function for everyone to become a writer—because writing, clarity of thought, and the ability to articulate your desired output is a prerequisite to use any of these new consumer AI models.

Dear Writer,

So you want to be a Category Copywriter?

Then let’s start by defining the difference between Sales Copywriting and Category Copywriting.

• Sales Copywriting is when you write words with the singular goal of increasing customer purchases now. You do this by finding lots and lots of different ways to articulate the benefits of the solution and/or the negative consequences of the customer’s problem. You’re “selling them” on taking action—and educating them on the bad things that will happen (or continue to happen) if they don’t.

• Category Copywriting is when you come up with 2 or 3 words that define the strategy of all the messaging that happens thereafter. The goal here isn’t necessarily to drive customer purchases now, but to create a moat of differentiation that creates net-new demand for your net-new category over a long time horizon.

Said more simply: Sales Copywriting is sales (or persuasion), which tends to have an incremental and more immediate impact on revenue. Whereas Category Copywriting is categorical differentiation, which is exponential—meaning as demand for your category grows, so too will demand for your company/product (because you “own” the category).

It’s winner-takes-all.

The Art of Category Copywriting

Category Copywriting is the nucleus of any company, product, or personal brand’s messaging strategy.

It’s the 1, 2, or 3 words that dictate all the words that get used thereafter, at scale, in every context, across every messaging platform—in sales, in brand marketing, and even in quarterly earnings reports.

This is something that took me a decade to understand. And unfortunately, it’s something I notice even writers with 30 or 40+ years of experience fail to wrap their heads around. That’s because it’s so simple, it’s complicated.

Let me give you an example:

In 2004, Elon Musk invested $6.5 million in the Series A round of a little upstart called Tesla. At the time, nearly every car sold (in the world) was gas-powered. Electric vehicles were considered impractical or failed experiments, and while the Toyota Prius (hybrid, not full EV) was starting to gain traction, pure EVs were virtually nonexistent in mainstream production.

What’s the net-new category? Again, it’s so simple, it’s complicated.

You have Gas Cars.

And then Tesla said, “We make Electric Cars.”

Same mega-category (Cars), but a different modifier (“Electric”)—one single word that has created two generations of differentiation and trillions of dollars in economic value. Tesla’s market cap today (at the time of my writing this) is $1.08 trillion. Then add in all the other Electric Car companies trying to capitalize on the exponential growth of the Electric Car category (and chase Tesla’s dominance within it).

One word (“Electric”) created trillions of dollars in value.

Now, imagine if Tesla in 2004 had hired a Sales Copywriter and said, “We want to make a car, and we want to communicate to customers why our car is better than all the other gas-powered cars out there.” What would a Sales Copywriter do? How would a Sales Copywriter use their skills to differentiate Tesla? Well, they would try to sell! They would try to persuade! They would try to convince customers why a Tesla is faster, or cheaper, or easier to use, or cooler to drive—compared to the competition.

Which is precisely the problem.

Most Sales Copywriters lack a “category lens,” meaning they can’t see the forest from the trees. Because it doesn't matter how convincing or persuasive your copy is… if you still call it a “Car” and don’t add (and then relentlessly evangelize) a net-new categorical modifier (“Electric”), you might sell a few cars today but you won’t win the differentiation war, build a messaging moat, and create a category that trillions of dollars of value can pour into over the next two decades.

Because it’s this modifier word, “Electric,” that has dictated quite literally every single decision the company has made since its inception:

• Product Roadmaps: Tesla has built and vertically integrated all sorts of electricity-based products, including building their own battery technology, software, charging stations, and today, AI-powered autonomous driving networks.

• Company Messaging: All of Tesla’s messaging (and Elon’s personal Twitter/X account) is about building zero-emission electric powered vehicles—and more grandiosely, becoming a “multi-planetary species.”

• Legacy Category Education: Tesla also frequently talks about the problems with the legacy category of gas-powered cars, and publishes impact reports on the progress they’re making to transition the world to sustainable energy.

Notice how Tesla spends very little time, energy, or resources promoting Tesla, the brand. They spend all their resources educating the masses on the net-new category of Electric Cars. Because if the Electric Car category grows, and Tesla “owns” the category, then as demand for Electric Cars goes up, so will demand for Tesla.

Which is why the entire game of Category Copywriting is to strategically use language to create separation in the customer’s mind (at the highest level) between the old and the new—what “is” and what “can be.”

Here’s how:

Category Copywriting Skill #1: Thinking In Modifiers

One of the most valuable skills to develop as a writer, but especially as a Category Copywriter, is to constantly be thinking in “modifiers.”

Because any modifier, placed in front of almost any word, dramatically changes its meaning—and as a result, the “direction” in which the reader interprets the message and begins thinking thereafter.

Some examples:

• The word “money” can be modified and its meaning changed drastically by adding “saving money” or “spending money” or “stealing money.”

• The word “life” can be modified and its meaning changed drastically by adding “saving life” or “taking life” or “sabotaging life.”

• The word “building” can be modified and its meaning changed drastically by adding “wood building” or “steel building” or “web3 building.”

Notice how one single word, strategically placed in front of the original word, completely changes a) your interpretation of the word, b) the meaning of the word, and c) the “direction” in which you begin to think.

The art of Category Copywriting is this skill executed at the highest level.

It is, quite literally, the compass you place inside your target customers mind—telling them, not just the message, but the direction in which you would like their attention to move.

Category Copywriting Skill #2: Naming & Claiming Categories

Building on “Thinking In Modifiers,” the next skill is learning how to effectively Name & Claim a new category.

This means coming up with 1, 2, or 3 words that accurately, uniquely, and immediately communicate what makes you “different.” (More than 3 words and you begin to write a sentence, which is an explanation. The customer doesn’t want an explanation. The customer wants 1, 2, or 3 words they can hold on to and repeat forever.)

The single biggest mistake founders, executives, investors, and accidental Category Copywriters make when trying to Name & Claim a new category is the use of adjectives.

If you take an existing mega-category (“Cars” or “Food” or “Beauty,” etc.) and attempt to modify it with an adjective to achieve differentiation, you accomplish nothing. Adjectives are weak modifiers—because they don’t actually change the meaning of the original word.

Watch:

• “Car” modified with an adjective becomes a “Better Car.”

• “Suitcase” modified with an adjective becomes a “Stronger Suitcase.”

• “Lipstick” modified with an adjective becomes a “Cheaper Lipstick.”

• “Pillow” modified with an adjective becomes a “Lighter Pillow.”

If you notice, adjective-modified products, services, companies, and marketing messages exist everywhere. This is what the masses believe marketing and advertising to be all about: communicating how you are {insert adjective} compared to the competition—better, smarter, stronger, cheaper, etc.

Instead, the secret is to modify an existing category with a stand-alone Noun or Verb that has its own individual meaning. Because when you combine two stand-alone words with separate meanings, 1 + 1 = 3.

• “Paper” modified with a noun becomes “Wrapping Paper.” New category.

• “Coding” modified with a noun/verb becomes “Vibe Coding.” New category.

• “Water” modified with a noun becomes “Vitamin Water.” New category.

• “Tape” modified with a verb becomes “Snore Tape.” New category.

• Etc.

The more the modifier word stands alone—and an easy trick for this is to think in Nouns & Verbs—the more net-new meaning and differentiation it creates when combined within an existing mega-category.

*NOTE: Grammatically speaking, many nouns & verbs act as adjectives when combined with another word. But that is in the context of a complete sentence. Naming & Claiming a category is not that.

Now, can you achieve categorical differentiation by using an adjective?

Yes, it’s possible:

• “Urgent Care” modified with an adjective becomes “Holistic Urgent Care.” New category.

• “Phone” modified with an adjective becomes “Smartphone.” New category.

• “Food” modified with an adjective becomes “Fast Food.” New category.

• Etc.

But over the years, I have found that nouns & verbs tend to produce more effectively named categories than adjectives. More importantly, “thinking” in adjectives, tends to lead to lazy comparison messaging: better, faster, stronger, smarter, cheaper, etc.

And that’s not where you want to be.

Category Copywriting Skill #3: Crafting A “Controversial” POV

Once your new category has been Named, it’s time to go out into the world and "Claim” it.

And the way you do that is by giving your new category a “controversial” POV.

Now, when I say “controversial,” I don’t mean for controversy’s sake. The secret here is for your new category’s POV to, in some way, go against the grain of conventional wisdom in the legacy category. Because when a message says something “different,” then guess what? It is!

This POV gets communicated in the company’s “tagline.”

Some of my favorite examples:

• Invisalign: “The clear alternative to braces.” - This tagline is brilliant in the sense that it is drawing a category comparison (braces = old category), but also saying the opposite of conventional wisdom in orthodontics. Braces are visual. Everyone hates how they look. But what if your braces were clear… even invisible? That’s a different POV!

• Zbiotics: “Drink before drinking.” - The new category here is Pre-Alcohol Probiotics. And so this tagline evangelizes that new category by succinctly explaining, “If you drink this, first… all the problems with the category of ‘alcohol’ go away.” That’s a powerful and different POV!

• iPod: “1,000 songs in your pocket.” - This is one of the most well-known product-category taglines of all time. What gets missed here, though, is that it’s actually drawing a category comparison between the legacy category (CDs) and this new category of portable music player. When the iPod was launched in 2001, you could barely fit a CD of 12 songs in your pocket. So saying you could hold 100x that was actually a categorical POV.

This is the entire purpose of your company, product, or personal brand’s tagline: to summarize your net-new category’s POV in a single sentence.

Because this succinct POV becomes the “script” your customers will repeat and use to talk about (and market) your company or product to other potential customers.

Marketing The Category (Not The Brand)

All these skills ladder up to the most important skill of all, which is a relentless commitment (despite all the people in the world proclaiming otherwise) to stay focused marketing your net-new category.

Not your brand.

As the Category Copywriter—whether you own your own business, or you’ve been hired to lead the messaging inside someone else’s—it is your job to carry the torch. You are the Chief Evangelist. And since one of the greatest misconceptions in all of marketing is that differentiation is the result of “building a brand,” this requires commitment. A lot of people will tell you you’re wrong. “Brand, brand, brand. Tell customers why we’re better than the competition!” But it’s your responsibility to hold steadfast, market the category, and trust that as the category grows… so will your brand.

For example…

If brand is all that matters, why did Google+ fail as a social platform? Google is one of the most well-known brands in the world. Google has more cash than most small countries. How could they fail? Because Google’s value as a brand sits in a different context. They are known for “search,” not “social.” And you can’t just take your brand into someone else’s category and expect to win—no matter how much money you have.

So, how do you market the category instead of your brand?

• You use those 1, 2, or 3 words you came up with for your net-new category… everywhere, all the time, forever. This is how you “become known for a niche you own.” Repeat them ad nauseam. Make them synonymous with everything you do.

• You market the problems with the legacy category. You spend at least 50% of your messaging efforts making sure people understand everything that is wrong with “the old way of doing things.” The nuance here is you are not trying to convince customers other brands are bad. What you’re doing is separating the way things used to be—the old category—from the way you believe things are and can be in the future—your new category.

• You market the benefits of your net-new category. You spend the other 50% of your messaging efforts educating people on all the fun, exciting, new, and different benefits attached with your net-new category. Again, the nuance here is you are not telling customers how great you, your company, or your brand is. You’re telling them about this new category—in which you just happen to be the leading, dominant player.

Which is why I say: broke writers get paid to write lots of words. Really rich writers get paid to write 1, 2, or 3 words that dictate the direction of a company's entire messaging strategy.

Now, a couple parting thoughts:

Is it possible to build a successful company and generate millions of dollars without any categorical differentiation? Yes. I know plenty of entrepreneurs and Sales Copywriters who have, and preach this business strategy. You just probably don’t know their names because they never became “known for a niche they owned,” and never gave you the language to market their categorical differentiation for them. Missed opportunity, if you ask me.

Is it possible to build a huge audience without any categorical differentiation? Also yes. And many do (and go on to make terrific, sometimes huge amounts of money). But I would argue many of these creators actually do have some sort of categorical differentiation—they just don’t know it, and haven’t acquired the skill of Naming & Claiming it. If they did, they would become far more widely known, and make even more money.

There are many different philosophies when it comes to marketing messaging, and plenty of success stories all across the spectrum.

But to become a Category Copywriter, this has to become your way of seeing the world.

Time Horizon

I graduated from college in 2013—which is the moment I started taking my career as a writer “seriously.”

And I didn’t land my first really lucrative Category Copywriting client until 2022, so nearly a decade later.

The truth is, Category Copywriting as a Writer Career Path isn’t something you unlock for a long time. The reason is because it is very advanced, second only to committing your life to become a Literary Writer. It takes a while for these principles to embed themselves into your head, your way of seeing the world, and your pen. Furthermore, most Category Copywriting opportunities come as a result of your network, through referral or high amounts of social credibility. And it takes a while to build a reputation that warrants these types of introductions.

My advice: learn these skills and practice them on yourself (“you” should Name & Claim your own category, too!). But don’t worry about monetizing them for at least a decade.

The other Writer Career Paths are much better for making money, faster.

The Business of Category Copywriting

In its simplest form, Category Copywriting is really just “consulting” with an emphasis on writing.

The key, however, is to get companies (and their founders, executives, and at times, investors) to understand that you aren’t being paid to “write.” If that were true, how could you possibly rationalize charging more than a few dollars for the 1, 2, or 3 words you’d be writing when Naming & Claiming a company’s new category?

In the context of Category Copywriting, word count is a horrible measure of value.

Instead, what you’re being paid to do is “think” strategically at the highest level—and then distill all that thinking into a very small, extremely dense grouping of words that, quite literally, dictates all of the words that company uses moving forward. Which is why charging per word, per hour, or per any unit of time or effort doesn’t make sense. Because if you are successful at helping a heavily funded venture-backed startup, or a publicly traded company successfully Name & Claim a new category and differentiate themselves from any and all competition, the “value of your value” could amount to millions, tens of millions, hundreds of millions, even billions of dollars of net-new demand.

Which is why most Category Copywriting deals are structured in stock options—or some blend of cash and equity.

Case Study: Category Pirates

In 2021, I co-founded a company called Category Pirates with two other entrepreneurs—Eddie Yoon and Christopher Lochhead.

The business started as a paid newsletter on Substack where we wrote about Category Design principles and how companies could reliably differentiate themselves. But the success of that paid newsletter led to companies reaching out, asking if we would help them execute these frameworks ourselves. And since one of the crucial parts of that work was helping Name & Claim a company’s new category, I played the role of Category Copywriter.

We grew the consulting portion of this business to millions of dollars in revenue.

I worked with companies all across the spectrum: Silicon Valley venture-backed startups, 9-figure e-commerce brands, even publicly traded companies with billion-dollar market caps. Some deals were all equity. Some were all stock options. And some were a blend: cash now, with potential upside later.

I exited the business in 2023. But this was my introduction to monetizing my talents as a writer through Category Copywriting & messaging consulting. I was no longer getting paid to write “lots and lots of words” (as I had as a ghostwriter). Instead, I was getting paid to come up with 1, 2, or 3 words that dictated a company’s entire messaging strategy—and I was given “upside” to capture a small portion of the value I created.

My Recommendation:

I know how tantalizing the idea of getting paid lots of cash and stock options for writing “a couple words” sounds.

But this is harder than it sounds. And my recommendation would be to pursue this career path last.

• It’s one of the most advanced career paths for writers.

• These types of opportunities tend to only present themselves after you’ve spent a decade building your network and credibility in an industry.

• And landing these opportunities is heavily dependent on your ability to “sell” the value of your value to a seasoned founder, executive, or investor.

More importantly, while there is a lot of potential upside in this type of work, Category Copywriting deals also come with the highest amount of risk. Out of the 20 or so equity and stock option deals I’ve done, only 2 have made me any money. The rest were all bets that went to zero, consuming a lot of my time and energy without putting anything in my pocket. (I should note, in nearly all of these cases, these companies ignored my advice and inevitably fell back into “comparison” messaging.)

As a beginner, and even intermediate writer, it just doesn’t make sense to take these kinds of swings when you’re still struggling to make $10,000 or even $20,000 per month and have a five-figure net worth. You have a much higher likelihood of success pursuing one of the other Writer Career Paths, first—and saving this one until you’re a millionaire.

Yes, Category Copywriting is the ultimate dividend on your talents and reputation. These are great deals to do when you’re “retired,” or when you have already made your money elsewhere. But until then, these high-risk types of deals are a distraction.

Take the cash instead.

Sincerely,

Cole

Dear Writer,

So you want to be a Writerpreneur?

This is a career path that began to emerge in the early 2000s.

Before the dawn of the Internet, writers were largely held hostage by legacy media and publishing companies. If you wanted to write a book, you needed a publisher. If you wanted to write opinion columns, or cover the news, you needed a publisher. Anything you wanted to write and share with the world had to be “chosen” by someone with distribution—which meant the number of available Writer Career Paths were limited to the platforms and publishers willing to back new writers.

But with the Internet, to quote a dot-com cliché, distribution became democratized.

Facebook, Twitter, Amazon’s Kindle Direct Publishing platform, etc., changed the power dynamic between writers and publishers. Suddenly, publishing your stories and insights didn’t require permission. All you had to do was press a button and your words could be viewed by anyone else with an Internet connection. But democratized distribution also caused an evolution in business models. The singular “you’ll-get-paid-what-we-decide” legacy publishing deal or columnist contract was no longer the only option.

We now call this buffet of new business models The Creator Economy:

• You can build an audience on a social platform and/or an email list, and sell your writing or related products directly to your readers. (Facebook/Meta, Twitter/X, LinkedIn, Instagram, YouTube, etc.)

• You can sell your writing (or related products) on your own website. (Squarespace, Wordpress, Shopify, etc.)

• You can sell your writing (or related products) on an aggregation platform with its own distribution engine. (Amazon, Google, etc.)

• You can sell access to your writing (or related products) through a monthly subscription and/or donations. (Substack, Patreon, etc.)

Write what you want. Charge what you want. And earn what you generate for yourself: end-to-end control—from first impression to final sale.

It’s an incredible era to be a Writerpreneur.

The Art of Writerpreneurship

Here’s the playbook for success in the digital age as a Writerpreneur:

• Pick a niche.

• Attract a social audience.

• Build an email list.

• Launch digital products.

• Spin the flywheel forever.

It’s simple in theory, but each step requires its own set of skills.

Of all the Writer Career Paths, being a Writerpreneur is the least writer-ly and requires the most digital savvy. This is both the pro and the con of “freedom of expression.” Everyone says they want creative freedom until they feel the burden of infinite choice. If you want to “just be a writer,” then take the publishing deal where you get paid a minimum-wage advance and a measly 10-15% royalty on your book sales. Just don’t be surprised when you see some Internet Writer earning 100x more than you. That was the trade—the decision you made! You traded not-needing-to-learn-any-other-skills for exponential upside. You chose to “just be a writer.” So you can’t simultaneously expect the same outcomes as someone who chose to be a writer PLUS everything else.

The more creative freedom you want, the more skills you must acquire in order to successfully leverage and monetize that freedom. Writerpreneurs aren’t the most talented, and certainly not the most literary writers. But they don’t have to be. That’s because “writing” is only a small part of the totality of what they do. Which means, if you want to unlock the rewards that come with being a Writerpreneur, then you need to embrace building these other non-writing skills.

*Quick Context: I have generated over $20,000,000 as a Writerpreneur through a wide variety of digital business models. I have also trained thousands of writers on all the following skills, and watched hundreds of them go on to generate tens of thousands, hundreds of thousands, even millions of dollars themselves.

Writerpreneur Skill #1: Pick An Infinite Niche

The first step to becoming a Writerpreneur is picking a niche.

The writers who make the most money in the digital age aren’t just “known.” The game isn’t about fame, or reach, or how many social media followers you have. The writers who make the most money are known for a niche they own. Because what readers are really buying—with their attention, but also their hard-earned money—isn’t “the writer.” It’s the writer’s position in a niche they care about. They are attracted to the topic, first—and the writer who delivers that topic to them, in a way they enjoy and find helpful, second.

Of course, telling a writer to “pick a niche” usually causes an existential crisis:

• “If I pick the wrong niche, I’ll have wasted years of my life.”

• “If I pick a niche, I’ll be stuck there forever and never be able to change it.”

• “If I get too niche, I’ll never be able to build a big enough audience to make any money.”

• “If I pick a niche, that means I won’t be able to talk about all my other interests—and I’m a whole person! I don’t want to limit myself like that!”

• Etc.

All of these are faulty beliefs—and clever ways writers talk themselves out of taking action.

The reason I say picking a niche is a “skill,” is because it’s a skill to identify a niche opportunity and trust it—especially when everyone else around you says that niche is “too small.” It’s a skill to stick with a niche even when it doesn’t seem to be very promising, or growth has slowed. And it’s a skill to not niche-flop every time you see someone else succeeding with some new shiny object.

The fundamental reason so many writers struggle as Writerpreneurs in The Creator Economy isn’t because of lack of talent, or lack of intelligence, or even lack of differentiated ideas. The core reason is because they give up. Some give up before they’ve even started. Others give up when they aren’t magically a millionaire three weeks into the journey.

Which is why my advice (to all Writerpreneurs) is not to try to pick a trendy, seemingly lucrative niche—but to pick an Infinite Niche: something you are intrinsically curious about, a topic you think about all the time, and something you could write about forever.

(And yes, if you ever want to change niches later, you can. It’s not a marriage decision. But this is a good place to start.)

Writerpreneur Skill #2: Create A Niche-Specific Library Of Content

The second step is creating a lot of content, for free, in public, within that niche.

This is what builds your distribution—a web that stretches across the Internet attracting readers into your ecosystem who are interested in “that thing” you’re writing about.

For example, if someone becomes interested in “Digital Writing,” they are going to come across my work on the Internet. They just are. Not because of how many social media followers I have, or because of my name and personal brand. The reason they will come across my work is because I have spent a decade creating content on the topic of “Digital Writing.” I have a massive library of content in that niche. Which means the moment someone becomes interested in “that niche,” they will discover me.

This what so many aspiring Writerpreneurs get wrong. You are not monetizing “yourself” or your personal brand.

You’re monetizing your niche, and your leadership position in it.

Writerpreneur Skill #3: Build A Niche-Specific Email List

The third step is bringing your “rented” audience (on any social platform) over to an “owned” email platform.

Because you don’t own your social media followers.

But you do own your email list.

Another misunderstanding people have about the Writerpreneur career path is that you make money by selling digital products to your social audience. And that’s not entirely true. Yes, some followers will buy your products through social channels, but all the money gets made by selling through email. Why? Because email is more direct (you aren’t speaking to an algorithm, you’re showing up inside someone’s personal email inbox); email is more reliable (again, not relying on an algorithm to “show” your content to your followers); but most importantly, email tends to be longer form. You can give more context, tell longer stories, and make more convincing pitches as to why someone should trade their hard-earned money in exchange for your writing.

So if you want to make money as a Writerpreneur, then you have to realize that the size of your social audience isn’t the most important metric.

The number that really matters is the number of subscribers on your email list.

Writerpreneur Skill #4: Launch Niche-Specific Digital Products

The fourth step is to monetize all this niche attention you’ve aggregated via email.

And as a Writerpreneur, you can monetize audience attention in all sorts of different ways:

• SaaS: Digitally savvy Writerpreneurs can take their writing skills and wrap them in a SaaS platform and/or AI platform. This is one of the more advanced ways of monetizing your talents, but it’s becoming more and more popular as tools get easier to build and AI does more of the coding. For example, Dan Koe has done this with his AI Writing software tool, Kortex. And we’ve done this with our SaaS platform, Typeshare.

• Paid Newsletter: Think of a paid newsletter as the longest-form, most in-depth, most “exclusive” version of all the same content you write about for free on social platforms, and the same content you write about in your free weekly newsletter. Paid newsletters are an amazing business model because they unlock subscription revenue—a historically rare (if not impossible) business model for writers. Instead of selling a stand-alone book for $20, you can charge $20/mo for ongoing access to the content in your paid newsletter (aka: “a book that never ends”). We have done this with our paid newsletter, Write With AI (which, at the time of my writing this, currently does $400,000+ per year in annual recurring revenue).

• Low-Ticket Digital Products: This is the most common monetization model for Writerpreneurs. You write social content in a niche. You attract a nice audience. You bring that niche audience over to an email list. And then you sell those people a hyper-relevant, hyper-specific text and video course—usually priced somewhere between $149 to $350. For example, I write about Digital Writing, but I also write about Ghostwriting and AI Writing. So every time I write about one of these (related) topics, I send that social traffic to a different email list/newsletter. And then once every couple months, we pitch each individual email list on a different hyper-relevant, hyper-specific low-ticket digital product.

• High-Ticket Digital Products: This is the harder, more advanced version of selling Low-Ticket products. High-Ticket usually means selling education plus some amount of accountability, accessibility (to you), community, and support. A good example of this would be our Premium Ghostwriting Academy. This is not “just” a text & video course on ghostwriting. You also get access to a private Slack community, a private channel with me and our entire team, a 1:1 Success Coach to hold you accountable through the program and review all your assignments, weekly live sessions with our leadership team, and a weekly program-wide Hot Seat live session with me. All of these other hands-on benefits are why High-Ticket programs tend to be in the $3,000 to $20,000 range.

Now, Writerpreneurs can also write books—and either go the traditional publishing/book deal route, or self-publish. Writerpreneurs can also launch physical products or offer services. And Writerpreneurs can also sell ads in their free newsletters.

Being a Writerpreneur—someone who has a social audience, dominance in a niche, and a niche-specific email list—allows you to monetize in more ways than any other Writer Career Path. It’s incredibly liberating, and also lucrative. But again, all this creative freedom comes with the burden of infinite choice.

That’s the pro/con.

Writerpreneur Skill #5: Stick With A Niche For A Decade

I have been writing on the Internet since 2007.

Over the past two decades, I have seen a lot of digital writers and creators come and go. Many find success in a niche, quickly gain traction, make some money, reach a peak, and then quit.

To “beat them,” you didn’t have to be better than them.

You simply had to keep going.

But look around: all of the Writerpreneurs who make millions of dollars on the Internet have been writing about a particular niche for years. Not days. Not weeks. Not months. Years—and eventually, decades.

This is the big insight that takes beginner Writerpreneurs a long time to fully understand. Your success has very little to do with your ability to write something that performs well in the short term. In fact, it’s irrelevant. The real “game” you’re playing is long-term niche dominance.

Because…

• The more content you create in a niche, the wider your web grows.

• The wider your niche web, the more people you will passively attract into your corner of the Internet (with less and less effort as time goes on).

• The more niche-specific readers you attract, the larger your niche-specific audience will grow, the faster your niche email list will grow, and the more trust and authority you will build in that niche.

• The more trust and authority you have in a niche, the easier it becomes to monetize (because readers believe, “I get so much value out of your free content… I can only imagine the value of your paid content!”).

• And the more niche-specific digital products you build, and the more customers you make happy, the more likely those customers are to buy your next product, or subscribe to your next paid newsletter, etc. (And recurring existing customers means you have to spend less effort and/or resources trying to find net-new readers to turn into customers).

It’s not a game of personal branding.

It’s a game of niche dominance.

Other Writerpreneur Skills

Of course, “writing well” on the Internet is a core skill of being a Writerpreneur.

Which includes the following sub-skills:

• Hooks: It doesn’t matter how entertaining or valuable the content is—if you don’t learn the skill of crafting hooks that “sell” readers on why they should give you their attention, they won’t.

• Formatting: Writing on social platforms is not like writing a book, and very few of the legacy formatting techniques apply. Digital Writing is all about single-sentence openers, bulleted lists, short paragraphs, listicles, even text plus media. You have to learn how to format your writing for digital readers.

• Social Platform Languages: X (Twitter) is its own language. LinkedIn is its own language. Medium is its own language. Each Digital Writing platform has its own nuances, preferred formats, editing functions, and even inside jokes. So it’s not enough to just “be a good writer.” You also need to know how to write well within the constraints and culture of each platform.

• Engagement Tactics: “Publish and they will come” is half-baked advice. Yes, writing and hitting publish on a consistent basis is required, but you also need to build the skill of promoting your writing as if you were hustling mixtapes out of the back of your car. This means engaging with other writers, participating in your niche’s broader community, collaborating with other creators, even appearing as a guest on relevant podcasts. Self-promotion is required.

And by the way, if you are interested in this career path and want to accelerate the acquisition of all these skills, I encourage you to come join us in Ship 30 for 30. This is our beginner writing program, and specifically designed for Digital Writers who want to capitalize on this new Creator Economy.

But in addition to writer-specific skills, Writerpreneurs also must build a suite of non-writing skills:

• Platform Skills: The same way social platforms should be considered their own sub-language, so should “hosting” platforms, community platforms, payment processing platforms, marketing platforms, and so on. In fact, many of these platforms are so robust that other entrepreneurs and Creators build entire careers out of mastering just one of them. As a Writerpreneur, part of the job description is keeping tabs on all the new platform innovation happening in the digital world, and knowing “enough” to either do it yourself or intelligently hire someone else to help you.

• Automations: This is an emerging skill, but is quickly becoming a baseline expectation for Writerpreneurs. Tools like Zapier (which allow for low-code or no-code automations between platforms) can unlock a tremendous amount of efficiency. And so it’s no longer enough to just “write,” or “write and monetize.” If you want to make hundreds of thousands, or millions of dollars as a Writerpreneur, incorporating automations into your 1-person publishing empire is table stakes at this point.

• Miscellaneous: Growth tactics, negotiating partnerships, affiliate marketing campaigns, paid advertising… the list of “other skills to build” is quite literally endless. That’s not to say you HAVE to acquire every single possible skill (lack of focus and specialization is just as big of a mistake), but the joys of Writerpreneurship and the freedom that comes with it ultimately means “everything” is an option.

Case Study: Justin Welsh

One of the best examples of what it means to be a successful, digital-first Writerpreneur is Justin Welsh.

And his “Career Path” is very simple:

• He picked a niche: Solopreneurship, and how to build an Internet cash-flow business with 0 employees.

• He started writing about the niche of Solopreneurship on X and LinkedIn.

• Over time, he moved that social audience over to a weekly newsletter called “The Saturday Solopreneur” (which he promotes in almost every single social post he writes).

• He then launched a variety of different low-ticket digital products, teaching people how they can get started as Solopreneurs too: LinkedIn OS, Content OS, and Creator MBA.

• And he has done this for 5+ years, writing about Solopreneurship (and almost nothing else) every single day on social platforms, and in his newsletter, over and over and over again.

And Justin Welsh has generated millions of dollars in revenue with his 1-person business.

And he did it by dominating the niche of Solopreneurship.

Justin and I have become friends over the years, so he was kind enough to share a little private Q&A here:

1. Have you written about / do you remember some of the big inflection points for you as a writer online? When was the first moment where you realized "this is working" and you had real confidence in the path forward?

“I started writing on LinkedIn in late 2018, and much like any new writer, I basically heard crickets. I made a commitment to continue writing, and in May of 2019 a piece of content I wrote got 1M+ views on the platform. That was when my eyes were opened to the power of digital writing and my ability to succeed if I continued.”

2. When were you "working the hardest" on this new path? What did that workload look like? And when did you start to feel the inflection point where you could work less but growth kept going up?

“I think the hardest I worked was in 2023. Before this, I kept my business lightweight and simple, and most of my revenue was driven by writing on social media. It wasn't all that complicated. But in 2023, I worked on building "defense,” so professionalizing my brand, redoing my site, building an SEO strategy, getting better email automation, installing better metrics, etc. It's been one hell of a lift and short-term stressful. But all of this is what helped me hit that next inflection point.”

3. How long did you wait to launch your first product / why / what was the thinking there? If you could go back, would you have launched a product sooner?

“I waited until 2020 when I had about 21,000 followers on LinkedIn. Back in the day, that was a lot. So I launched a simple $50 course on how I wrote on LinkedIn. My thinking was that people needed to learn how to use the platform effectively, and I didn't want to exclude people by making it some big, expensive course. Over 18 months, it sold about $75,000. I don't wish I had started sooner or waited longer. I think the timing was just about right for my business.”

4. What are the other ways you're monetizing in addition to your low-ticket digital products? What's the vehicle / price point?

“I also sell $6,000 in sponsorships each week for my newsletter and have a $9 subscription email that has about 2,500 customers each month.

5. Can you share revenue numbers for your 1-person business?

“I generate roughly $195,000 per month in revenue:

• $146,000 average in course sales (75%)

• $23,000 in subscription emails (12%)

• $26,000 per month in sponsors (13%)”

6. Do you see yourself ever taking the next step, getting a publishing deal & writing a book? (That seems to be a theme for Writerpreneurs these days.)

“I don't think so, but maybe. The book process feels like having a job: Deliverables, deadlines, pressure, etc. I make a great living without those things. I'll consider self-publishing as well.”

8. What does "success" mean to you on this writing path you've chosen for yourself?

“Success to me is dual-sided. One side means being able to help people achieve their goals and build their own internet companies. The other side is building my business model in a way that lets me do what I want, when I want, with whom I want and very little of what I hate doing.”

Time Horizon

I have found a lot of success with the Writerpreneur Career Path.

But I have also become friends with many other Writerpreneurs succeeding in The Creator Economy. And I have trained thousands of writers (in our beginner writing program, Ship 30 for 30) on how to pick a niche, build an audience, and start launching digital products on the Internet.

And over and over again, I tend to notice the following:

Month 1:

This is where 90% of people start and stop.

They buy a course, or they watch some viral YouTube video from a guy in a Lambourghuini talking about how he “makes money while he sleeps,” and they get all fired up about building an audience online. They take two steps forward, they write and publish two pieces of content, and then when they don’t wake up that third day with thousands of followers and millions of dollars, they give up. They say, “X (Twitter) is broken. LinkedIn is saturated. YouTube is rigged. Nobody can make money on the Internet anymore.”

And then they call digital products/online courses a scam.

Months 1-6:

Only 10% of people make it through the first month.

The ones who do are either very bought in on the process. They understand that Rome wasn’t built in a day, and great things take time; or, they accidentally found a little bit of success in the beginning (a post randomly went viral) and that has “shown them the light” of what’s possible, and now they’re hooked.

More importantly, these people tend to have an emotional connection to whatever topic they’ve chosen to write about. They aren’t just trying to “get rich quick.” They’re trying to make a difference, and share their knowledge with the goal of helping other people. This is what keeps them writing day after day, regardless of whether their content performs well or not.

Ironically, it’s this detachment from short-term outcomes that makes them more successful over the long run.

Year 1:

Of the 10% who stick with it for 1-6 months, less than 1% stick with it for 6-12 months and beyond.

Which is also why, generally speaking, I tend to notice most Writerpreneurs start seeing real success right around the 1-year mark. 99% of the competition has quit! Furthermore, it takes time to figure out what niche you feel excited to write about every single day for a decade. It takes time to build your library of content, and attract a social audience. It takes time to bring that audience over to a newsletter, and build a high-value email list. And it takes time to not just create digital products, but launch them, market them, and iterate with feedback from your customers.

So, how “fast” can you make money as a Writerpreneur?

Of all the Writer Career Paths, certainly faster than being a Literary Writer, Genre Fiction Writer, or Non-Fiction Writer, that’s for sure. But not quite as fast as providing a service—like being a Copywriter or Ghostwriter (unless you already have an existing and growing niche social audience).

The Writerpreneur Career Path takes time to build momentum, so it’s typically slower to start. But because the products you end up selling are digital, when things get going… they are much more scalable. This is how people like Justin Welsh are able to generate millions of dollars in revenue with 0 employees.

So if you want to pursue this career path, I would strongly encourage you to choose a niche and give yourself at least a year.

Because most of the time, Writerpreneurs don’t have a “niche problem” or even a “talent problem.”

They just have a consistency problem.

The Business of Writerpreneurship

The way most Writerpreneurs make money is by selling education online.

• Some also sell physical products—journals, merchandise, coffee table books, etc.

• Some are affiliates for other products—like coffee, energy drinks, software, etc.

• And some sell experiences—events, small in-person workshops, masterminds, etc.

As a Writerpreneur, just about any business model under the sun is “possible.” But the primary, and most popular business model (and the one that tends to be the most lucrative and least operationally complex) is selling education.

And when it comes to selling education, there are 6 different vehicles to choose from:

Vehicle #1: Low-Ticket Digital Product

The first, and the vehicle I recommend all beginner Writerpreneurs start with, is selling a low-ticket digital product.

This could be:

• [$20]: A PDF download

• [$49-$99]: A PDF download + video(s), a template pack, or a paid email course.

• [$99-$350]: A text & video course

Now, obviously the value here (for the customer) isn’t the fact you’re giving them a PDF document, or a bunch of text and video modules. The value is the information you provide inside those assets. Oftentimes, beginners get very caught up and overwhelmed trying to figure out if selling a stand-alone PDF is better than selling a template pack, or if a template pack is better than a 3-module mini-course, or if a mini-course is better than a paid email course, etc.

The truth is, they all work. What matters more is the value of the education you are providing, the pain and urgency of the problem you’re helping the customer solve, and how easily you can help them solve it.

Now, that said, I have sold millions of dollars worth of low-ticket digital products on the Internet. And I can tell you that while all these different mediums and price points “work,” the best low-ticket digital product to sell is a stand-alone text & video course for $350.

For the following reasons:

• First, a text & video course can provide “obscene value at a laughable price.” If you pick a tangible, painful problem in your niche, and are able to help customers solve it with actionable education, the price tag of $350 becomes negligible. For example, we have sold digital products at this price point and watched customers implement our teachings and go on to generate hundreds of thousands of dollars in revenue. That’s an insane ROI. (Find me a stock that yields that kind of return!)

• Second, there is a clear pricing ceiling for asynchronous text & video courses right around $350. This is one of the biggest mistakes I see Writerpreneurs make: they build a text & video course and then try to sell it for $500 or $999 or $2,459—not realizing that once you cross the $350 pricing threshold, the way the customer evaluates the purchase changes. And typically, at these higher price points, the customer is expecting something more experiential. They want community, they want 1:1 coaching, they want live sessions, they want access to you and/or a team to help them implement their learnings and answer their questions. So if you’re going to sell an async text & video course, be sure to keep the price point at $350 or below.

• Third, you have to learn how to sell something stand-alone before you can sell something recurring. Another mistake a lot of beginner Writerpreneurs make is they try to jump straight to more advanced vehicles. They think their first product should be a paid newsletter, or a recurring community—not realizing that recurring products are really just “ongoing” versions of stand-alone products. And if you haven’t figured out how to sell people one thing, what makes you think you’re going to be very good at selling them new things every month?

Which is why I say: the single easiest way to build these skills and start monetizing as a Writerpreneur is to sell a stand-alone $350 text & video course that helps customers in your niche solve a specific problem and unlock a specific outcome.

And I would strongly encourage you not to move on to these other more advanced vehicles until you do!

Vehicle #2: Subscription (Low-Low Ticket)

The second vehicle for monetizing education is through a subscription to your content. And the most popular version of this vehicle today is a paid newsletter.

For example, I have a paid newsletter on Substack with my business partner, Dickie Bush, called Write With AI.

This paid newsletter exclusively helps people learn how to write with AI. Every week, we write two paid newsletters sharing different writing frameworks, and then pair those frameworks with an AI prompt we’ve written to automate that framework. That’s the promise, that’s what readers expect, and we deliver on that promise every single week.

And at the time of my writing this, we have 1,700+ paying subscribers, and Write With AI generates over $400,000 per year in annual recurring revenue.

Now, here’s why monetizing via a subscription is so great:

• First, recurring revenue is the holy grail. Selling stand-alone products (whether it’s digital education, or books) is a game of churn and burn. It’s a great place to start, but as time goes on it takes more and more effort to acquire new followers, turn those followers into email subscribers, and then convert those email subscribers into customers. That’s not to say subscription businesses are “easy,” or take less effort—in some cases, they take more effort! But when executed correctly, subscription businesses tend to be more lucrative, defensible, and predictable.

• Second, your list of paying subscribers is also a list of your highest-intent customers. This is an opportunity a LOT of Writerpreneurs completely miss. If someone is actively paying you $20 per month for access to your content, they are 10x more likely (than all your free subscribers) to want your help solving more, more advanced, or different but related problems—and will happily pay you a premium to do it. For example, we now aim to launch one new stand-alone digital product ($350) specifically to our Write With AI list of paying subscribers each quarter—further extending customer lifetime value.

• Third, a paid newsletter has no marginal cost. It doesn’t matter if you have 10 paying subscribers or 10,000 paying subscribers, it still takes the same amount of time each week to write your newsletters. This is where your leverage as a Writerpreneur starts to compound. You don’t need to hire people as your business grows. You don’t need to incur costs to warehouse physical products. A paid newsletter is one of the most profitable, and least operationally complex business vehicles on the planet—especially when built on organic traffic (opposed to cold ads).

So, if paid newsletters are so great, when should you start one?

Well, the way I like thinking about it is that a paid newsletter is just a book that never ends.

Which means the answer is… you should start a paid newsletter once you’ve validated (with a $350 low-ticket digital product) what sort of “book” someone would want to read for months, or years, or decades.

Vehicle #3: Cohort-Based Course

The third vehicle for monetizing education is to run a cohort-based course.

This is different than building and selling an asynchronous text & video course. With an async course, all you’re selling is “the information.” And that’s fine! But in order to get above the $350 pricing ceiling, you need to provide more than just “the information.”

For example, most cohort-based courses also include experiential elements, such as:

• Live Sessions, where you can learn directly from the person running the program.

• Homework Assignments, where you can put your learnings into action.

• Community, where you can interact and learn from other people in the program.

• Small Group Breakout Rooms, where you can connect with other likeminded people directly.

• Templates, to help you implement all this new information faster and more effectively.

• Gamification, rewarding students for completing assignments, engaging in the community, or consistently putting their learnings into practice.

• And anything else that increases the likelihood of students being successful.

That said, there’s no “one right way” to run a cohort-based course. Some cohorts are 30 days, others are 5-day sprints, and some are 6-month commitments. Some lean more heavily on the live sessions for instruction, whereas others provide most instruction and education asynchronously and reserve live sessions for Q&As.

All that matters is whether or not your students successfully solve the problem(s) you promised to help them solve, and unlocked the outcome(s) you promised to help them achieve.

So, when should you start a cohort-based course?

• Signal #1: When you’ve successfully sold a $350 async text & video course, and want to move up to the next pricing tier ($500 - $999). Like I said, in order to get above that $350 ceiling, you’re going to have to add “experiential” elements to your digital education. The mistake Writerpreneurs make though is not recognizing this means building a different business. Because when you change the business model, the business changes.

• Signal #2: When you’re ready to handle more operational complexity. Speaking from experience (because we ran Ship 30 for 30 as a cohort-based course for 3 years, holding 20 live cohorts and teaching over 10,000 people how to start writing online), running a cohort-based course at scale is significantly harder than selling asynchronous text & video courses. Because now you need real-time customer support, automations to track people’s progress, advanced email marketing segmentation, gamification systems… all sorts of stuff to keep people engaged from the beginning to the end. (At least, that is if you want to do a good job.)

• Signal #3: There’s a tangible benefit for the customer for them to learn live in a cohort, opposed to asynchronously. This is the big one. I would not recommend building a cohort-based course because this business model sounds fun to you. Instead, I’d ask the question, “Is this experience going to help the customer in a way I’m unable to help them asynchronously?” If the answer is No, then you’re better off just selling an async text & video course. But if the answer is Yes, then you should embrace the challenge of building a program that is more likely to help the customer achieve their goal(s). For example, what made Ship 30 for 30 so successful wasn’t “the information.” It was the fact that it held people accountable and challenged them to write online, every day, for 30 days. Was “the information” helpful? Of course. But what was more helpful was having a program that forced action.

Vehicle #4: Recurring Community

The fourth monetization vehicle is to build a recurring community.

Generally speaking, the default price point for this vehicle is around $99/mo. Some communities charge as little as $5/mo (which is a massive mistake, and almost always the result of the creator’s own faulty beliefs around money and what they can charge). Other communities charge a little more: $149/mo, $199/mo, maybe $249/mo, etc. And some communities, depending on who the target customer is, the target industry, and the problem you’re promising to help them solve, can be as high as $999/mo.

But for the sake of simplicity, let’s default to $99/mo.

There’s 3 things customers expect when paying a monthly membership to a recurring community:

• Text & Video Curriculum: As soon as someone joins, they are going to want to go through some sort of “course” that helps them get started immediately.

• Monthly Unlocks: In addition to a baseline curriculum, there’s usually some sort of expectation around monthly content drops: new modules, new templates, new “what’s-working-right-now” strategies, etc. These monthly unlocks also act as incentives to keep customers from churning and cancelling their subscription (because there’s always something new, right around the corner!).

• Live Sessions: This is entirely up to you, and depends on what type of community you want to build, but typically there’s also an expectation for there to be a live component. It could be a weekly Q&A call, a monthly “masterclass” type call, bi-weekly guest speakers, etc.

But “communities” are a bit of a black box, in the sense that you can add whatever features and benefits you want inside.

You could also include:

• Member Introductions: Having some sort of system for connecting people within the community, facilitating friendships or partnerships, and proactively helping people build relationships.

• Gamification: Competitions, leaderboards, prizes, and anything else that incentivizes members to take action and participate in the community. (Community platforms like Skool have many of these features built-in, making them easy to deploy.)

• Content Vaults: As you run your community, you can upload live session recordings, guest lectures, etc., to a vault that grows in value over time. (Pretty soon, you’ll be able to say things like: “Over 100 hours of masterclass replays inside!”)

Now, if you notice… a recurring community is significantly more work than building a low-ticket ($350), asynchronous, text & video course. Which is why I always recommend to start there, first.

The faulty belief Writerpreneurs have though, and the reason so many choose to make their first monetization vehicle a recurring community, is that “it’s cheaper” ($99/mo vs $350 one-time). And they think “cheaper” automatically means “more people will buy.”

Which is both true, and false.

It’s true in the sense that, yes, you may get more “customers.” But everyone forgets to do the math. If you have a $99/mo community, and the average customer only stays for 2 months (and then cancels), that means the average lifetime value per customer is $198.

Said differently: if you had just sold a $350 digital product instead, you would have “less customers,” but you also would have made more money with a much simpler business.

We have a saying inside our company, as a reminder to ourselves how hard recurring communities are to build, and it goes like this:

“Everyone loves the idea of recurring revenue, until they realize they’ve just signed themselves up for recurring work.”

Vehicle #5: High-Ticket Group Coaching

The fifth, and most operationally complex monetization vehicle, is to build a high-ticket group coaching program.

This is where you train a very specific person, on a very specific set of skills, almost always price anchored to the value of the customer improving their life in one of four major categories:

• Health: How to lose weight, how to gain muscle, etc.

• Wealth: How to make more money, how to invest money, etc.

• Career: How to change careers, how to get promoted to a specific role, etc.

• Love: How to date, how to find find your soulmate, etc.

Think of this monetization vehicle as the expert version of selling a low-ticket digital product, combined with elements of building a recurring community.

This is because High-Ticket Group Coaching programs typically involve:

• An Asynchronous Curriculum: This is the “core” education of the program, and includes text & video modules helping the target customer solve very specific problems to unlock very specific outcomes.

• Weekly Live Sessions: These could be with you, your team, or some combination of the two.

• 1:1 Coaching: High-Ticket programs almost always involve some sort of direct coaching. The model is typically one coach is responsible for anywhere from 10 to 100 students, depending on the level of depth and accountability that is being promised.

• A Private Community: Another benefit of the program is usually access to all the other people who are struggling with the same things, and all learning how to improve together.

• Gamification: Internal challenges, rewards for completing assignments, community swag, etc., are all things customers expect from these types of programs.

For example, our Premium Ghostwriting Academy is a high-ticket group coaching program. It is 16 weeks, provides a full text & video curriculum, but also includes a private community for ghostwriters, 1:1 coaching, weekly live sessions with me and our team, internal challenges & rewards for completing assignments, and a slew of bonus resources only for people inside the program.

This heightened level of support, accountability, coaching, and access (to you) is why most High-Ticket Group Coaching programs are priced in the $3,000 - $15,000 range. Because it would be impossible to provide this level of personalized support and coaching in a $99/mo community (you wouldn’t have the margin to support the size of team required).

Vehicle #6: Mastermind

The sixth, and most expensive monetization vehicle is to build a mastermind.

To put it very simply: a mastermind is really just a more expensive Group Coaching program, for a more affluent customer, with less emphasis on “coaching” and more emphasis on “the other people in the mastermind.”

For example, most masterminds include the following:

• Digital Curriculum: This is a text & video curriculum usually focused on an “expensive” problem that a very specific sort of customer needs help solving. For example, in 2023 we joined a mastermind (for $68,000) that specialized in helping entrepreneurs build a sales team to scale a High-Ticket Group Coaching program to millions of dollars in revenue. And that might sound like an astonishing amount of money, but the digital education we received from joining that mastermind is literally how we built a sales team to scale our own High-Ticket Group Coaching program—generating north of $10,000,000 in revenue. So, yes, it was worth it.

• In-Person Events: For most masterminds, the primary benefit is being in the same room as “other people at your level” 2-4 times per year. Now, a lot of people think this means “networking”—and yes, there’s some value there. But, speaking from experience, the real value of being in the same room as “other people at your level” is that it desensitizes you. You sit in a room and talk with a bunch of people making more money than you, or working with cooler clients than you, or achieving the things you want to achieve, and you suddenly realize, “Wait a second… they aren’t any smarter than I am!” That realization, and the confidence that comes with it, is what you’re paying for.

• Guru Access: Lastly, half the reason why people join masterminds is to learn directly from someone in particular. It’s not just that you want to learn “how to do something.” It’s that you want to learn how to do something from someone specific. And this person might hold a monthly call where they field questions from mastermind members. Or, they might promise a 1:1 call with you each month for 30 minutes. The level of access is up to the person.

Now, when you should you start a mastermind?

Well, I’ll tell you when most entrepreneurs/Writerpreneurs decide to start masterminds. It’s after they’ve made their money using one (or several) of the other monetization vehicles, and have reached a level of financial comfort, proficiency, and credibility in their industry.

And at that point, a mastermind is really just a vehicle for them to monetize their network and their existing knowledge.

My Recommendation:

There are so many ways to monetize the craft of writing—which is what makes the Writerpreneur career path both liberating and, at times, frustrating. When you have infinite options, which direction should you go?

If your goal is to make as much money as possible by writing—which means you are less interested in acquiring other skills like building and scaling a sales team, learning how to run paid ads and build funnels, etc.—then here’s my prescriptive answer:

• Step 1: Pick a niche.

• Step 2: Attract a social audience.

• Step 3: Build an email list.

• Step 4: Launch low-ticket digital products.

• Step 5: Build a paid newsletter.

This is the most “writer-ly” version of the Writerpreneur career path, the easiest to learn and simplest to execute, and the least operationally complex—while still having the potential to be obscenely lucrative.

Anything beyond this inherently means leaning more toward “entrepreneurship,” and further and further away from “writing.”

Dear Writer,

So you want to be a copywriter?

That must mean you love sales!

The correct use of the term “copywriting” has to do with “sales copywriting,” as in writing words with the singular goal of increasing customer purchases.

Copywriting examples:

• Writing Video Sales Letter (VSL) scripts—to drive/increase purchases.

• Writing ads that drive click-throughs, opt-ins, and purchases.

• Writing landing pages that drive/increase purchases.

• Writing sales emails that drive/increase purchases.

• Etc.

Copywriting is a very specific “world” of writing—and, from my experience, an “insider” community. If you’re in the Copywriting world, everybody knows everybody and it’s a competitive & lucrative space to be in. But if you’re NOT in the Copywriting world, chances are you have no idea this community of writers exists—and if you were to step inside of it (especially if you were, say, a Literary writer), you would be shocked at how differently Sales Copywriters think about language, persuasion, and human psychology.

Quick Context: I have generated millions and millions of dollars as a Sales Copywriter—both for myself and my own businesses, as well as for other businesses. I have also been mentored directly by some of the most successful sales copywriters in the world, and have been “in the room” at some of the most insider-y Sales Copywriting masterminds.

Copywriting vs Ghostwriting vs Content Writing

In the short-term, Content Writing, Ghostwriting, and Copywriting can all earn you about the same amount of money. (There are tons and tons of writers who provide these services and all hover in the $5k/mo - $25k/mo range.)

That said, there are some core differences between these 3 services:

• Content Writing: Usually “content for the sake of content,” and almost always the ongoing creation & management of a company’s blog. However, less “digital-marketing savvy” companies tend to refer to the creation of any asset as “content writing/marketing.” Since these services are the most vulnerable to AI, this is the least valuable service of the three services listed here.

• Copywriting: Any written asset specifically engineered to “sell” the reader on something. It could be an email. It could be an ad. It could be anything. But Copywriting is sales.

• Ghostwriting: Any written asset specifically engineered to “educate” the reader on something. Similar to Copywriting, this could be anything from social content to weekly newsletters to YouTube scripts. But Ghostwriting is education.

The major difference with Sales Copywriting, however, is that the best copywriters in the world (the top 1%) can negotiate revenue share deals—which is where you’re able to jump out of trading hours-for-dollars and into a more scalable & lucrative vehicle. (This never happens in the world of Content Writing. Although it can happen, in different ways in the world of Ghostwriting—like negotiating a royalty on a book you ghostwrite.)

For example: There’s a little-known book in the Sales Copywriting world called The 16-Word Sales Letter. The author, Evaldo Albuquerque, was a highly successful copywriter within Agora Financial—one of the most well-known publishing companies in the world and the pioneer of the “paid newsletter” category. (Their yearly revenues reportedly exceed $1 billion.) And in this book, Albuquerque explains how he has generated hundreds of millions of dollars for Agora Financial through his sales letters—of which he was paid a percentage, making him rich.

The Art of Copywriting

Copywriters are master communicators, not necessarily “master writers.”

Which is ironic, because writing is a game of communication and clarity of thought. It’s just the masses tend to associate “great writing” with “beautiful writing,” which is not always the same thing as “effective communication.” Someone can be a beautiful writer and an average communicator (eloquent sentences that say nothing novel). Conversely, someone can be an incredible communicator and a mediocre technical writer. But that’s fine, because in Copywriting, the beauty of the sentences doesn’t matter. What matters is the psychology behind the message.

Let me tell you a story:

When I was 27 years old, and had just moved to Los Angeles, I got introduced to arguably the most successful Sales Copywriter on the planet: Craig Clemens. He and his brothers had built a billion-dollar company called Golden Hippo, and Craig’s superpower was his ability to write compelling VSLs (video sales letters) for their portfolio of health & wellness brands.

Well, Craig and I bonded over our shared love of writing and, one day, he invited me over to his house to give me a crash course on Copywriting—since, at the time, I knew nothing about it. I had studied fiction writing in college, and become a proficient Ghostwriter, but didn’t know a thing about “writing words that sell.”

So, I drove up the Hollywood Hills to his ultra-modern home—the same house Britney Spears & Justin Timberlake used to live in—and sat next to him at his kitchen table. Through the floor-to-ceiling glass windows, I had a bird’s eye view of the entire city of Los Angeles. Behind us in the kitchen was a staff of personal chefs preparing lunch.

He opened his laptop and pulled up the VSL script that had put their company on the map. Then he turned the word document toward me and said, “This script sold over a hundred million dollars of probiotics in our first year.” The fact that this Google Doc of words in front of me had led to $100M+ in sales, in a single year, was hard for me to comprehend.

But what was even harder to understand was that, when I started reading, the script was full of incomplete sentences… spelling errors… and weird tense changes that, on paper, would absolutely be flagged by an English teacher for being incorrect.

And so my first impression of Copywriting was that it wasn’t “real writing.”

Oh, how wrong I was.

When I would ask Craig what his favorite books were on writing, he wouldn’t name the literary world’s canon—On Writing by Stephen King; Bird by Bird by Anne Lamott; etc. Instead, he cited books on psychology, and obscure case studies of little-known marketing campaigns no one knew about, but had changed the world. Like this one: in 1929, American Tobacco Company wanted to promote their Lucky Strike brand, specifically with the goal of increasing cigarette sales among women. So they hired the “father of public relations,” Edward Bernays (Sigmund Freud’s nephew), to come up with a campaign. Bernays then arranged for women to hold cigarettes up in the air as “Torches of Freedom” during an Easter Sunday Parade in New York to associate smoking with women’s independence and empowerment. Before Bernays’ campaign, it was largely taboo for women to smoke in public—but afterward, newspapers and ads began showing smoking as a fashionable and even emancipatory act for women.

What does that have to do with Copywriting? Everything.

Craig helped me realize that Copywriting is the art of getting inside the reader & potential customer’s brain—oftentimes understanding them even better than they understand themselves. And what moves them to “buy” isn’t some clever combination of sales-y phrases (a reductive understanding of the craft), but your ability to articulate the customer’s life experience even better than they can. Because when you can name, in excruciating detail, their hopes, dreams, pains, problems, ambitions, dreams, and deepest desires, they trust you. And when they trust you, they come to the conclusion you are the best person to help them—which is why they buy.

Run-on sentences, grammatical errors, and tense changes all came second to this priority number one, which was making the customer feel understood.

Over the years, Craig became a close friend and mentor and completely changed the way I thought about writing. We rarely talked about individual sentences, word choice, or any of the minutia most “real writers” spend their lives obsessing over. Instead, all of our conversations sat way up high in the hills, and were rooted in deep questions about human nature. “What do people care about? What are they afraid of? What do they want, more than anything else in the world?”

This is what the art of Copywriting is all about.

Case Study: Gary Halbert

Does that mean Copywriting isn’t “creative?”

Of course not!

If Hemingway had fallen in love with advertising instead of literature, he would have become Gary Halbert.

If you aren’t familiar, Gary is one of the most successful Copywriters ever. And he generated hundreds of millions of dollars in revenue for his clients long before the age of Internet marketing. He dominated during the golden era of direct mail in the 1970s through the early 2000s, and helped pioneer many of the tried-and-true direct-response advertising strategies still around today.

However, in my opinion, the sales letters Gary wrote for his clients aren’t even his most impressive body of work.

His greatest contribution to the art of Copywriting is a paid newsletter he started in the late 1980s, called The Gary Halbert Letter.

It was a newsletter printed and sent through physical mail where Gary would share marketing insights, critiques of advertising, and stories from his personal life that he tied back to sales psychology. It cost a couple hundred dollars a year for a direct-mail subscription, and by the early 1990s, The Gary Halbert Letter had become a go-to resource for direct response insiders and aspiring copywriters. This is also where he would bundle in other special offers, or promote upcoming seminars where he taught copywriting & persuasion.

The reason I associate Halbert with Hemingway is because, if you’ve read Hemingway, then you know he is best known for his short, terse style. Reading old Halbert Letters, their styles are nearly identical. Both short, terse, simple, yet profound. You can tell in Gary’s personal newsletter that he’s more than just a copywriter. He’s an artist, dissertating about copywriting, persuasion, and psychology. And these newsletters he wrote are timeless. Sure, the tactics are outdated, but the writing is not.

Fun fact, in 2018, I found a website that had compiled every single issue of The Gary Halbert Letter, printed them out, and organized them in chronological order into two massive three-ring binders. The entire collection cost approximately $2,000.

They’re sitting on my desk right now.

The Copywriter Career Path

So, what is the career path for becoming a Craig Clemens or Gary Halbert?

How do you get paid millions of dollars to “write words that sell?”

There are three levels, and generally speaking, this is the order in which most copywriters ascend:

• Level 1: Tactical. There are a lot of tactical copywriting jobs in the world, because there are a lot of things that need to be created/written when constructing a sales funnel or maintaining a direct-response marketing campaign. These tactical jobs usually involve building or writing smaller assets: newsletters, abandoned cart sequences, short ad scripts, landing page copy, etc. At this level, your compensation is almost always tied to time or effort in some way. You’re either getting paid per hour, or per month—or you’re getting paid to create a specific asset as a stand-alone project. You can make great money at this level, but this is where the vast majority of copywriters stay stuck.

• Level 2: Strategic. The next level-up usually gets unlocked only once you’ve proven your supernatural ability to “write words that sell” inside a company, or by selling products on your own. Once your skill is undeniable (and irreplaceable), you can start to negotiate upside, usually in the form of a revenue split—which means collecting some sort of royalty on sales you generate inside a funnel you have ownership over. This is how Evaldo Albuquerque at Agora Financial made his millions, as do many other under-the-radar copywriters within massively successful companies.

• Level 3: Ownership. The last level, which is really the final destination of all writer career paths, requires you to be entrepreneurial. The highest-paid copywriters in the world eventually realize, “Wait, hang on a second… why don’t I just do this for myself?” This means more risk, sure, but it also can mean 10x more upside. For example, Craig Clemens didn’t make millions of dollars cashing royalty checks from writing someone else’s funnel. He made millions of dollars by starting his own company and writing “words that sell” his own products.

Copywriting Book Recommendations

If you’re brand new to the world of Copywriting, here are some good places to start:

• Positioning by Al Ries & Jack Trout: This book is considered the Bible of product positioning. It explains the importance of figuring out the unique “position” in which your product can sit in the target customer’s mind—and how to use persuasion to reinforce that unique & differentiated position over and over again.

• Copywriting Secrets by Jim Edwards: Written by another copywriting legend, this book is a great “tactical guide” on how copywriting strategies actually get executed in written text. It’s less psychology, more How To—a great read for beginners.

• Very Good Copy by Eddie Shleyner: Another great tactical read for beginners, this is full of little “nuggets of wisdom” that sit at the intersection of copywriting psychology & How To tactical advice.

There are hundreds of books on the topic of Copywriting though, so these are just a couple of my favorites.

The truth is, no book or course or training will teach you more about copywriting than you trying to sell a product or service on your own.

All the best Copywriters are self-taught!

Copywriting Skills

So, if you want to become a proficient copywriter, what skills do you need to build?

And maybe more importantly, what are the best ways to practice them?

Skill #1: Customer Research

Fundamentally, you will not be able to write copy that converts unless you know everything there is to know about your target customer.

Craig Clemens shared an amazing exercise with me that he does before writing any piece of copy for any product. He will first read as much as he can about the target industry. Then, he will identify the archetype of person who would be considered the ideal customer. And then he will write an entire first-person narrative from that person’s point-of-view—almost like an autobiography. He’ll give them a name. A backstory. A past. A future. And he’ll get as detailed as possible about who they are, what they care about, what they’re afraid of, what mistakes they’ve made in the past, what “solutions they’ve tried” that didn’t work, their goals, their hopes, their dreams and ambitions, until it feels like this fictional character is as real as a friend in real life. This first-person narrative might be dozens of pages.

Then, and only once the character feels real, does Craig start writing copy.

Because now he knows exactly who he’s talking to.

Practice Recommendation: To practice this skill, I highly recommend using AI. Have detailed conversations with ChatGPT, Claude, or Gemini. Ask AI to educate you on the industry you’re trying to write within, and use AI to help you build this first-person narrative of your target customer. The more up-front work you can do, and the more clarity you have over exactly who this person is, the more persuasive your copy will be.

Skill #2: Experimentation & Specialization

There are so many different types of assets a Copywriter can create—which means there is tremendous benefit in copywriting “lots of different things,” but also benefit in eventually specializing in just one.

For example, writing an hour-long VSL is a completely different skill than writing a short-form newsletter. The structure is different. The pacing is different. The amount of time and space you have to play with is different. The medium is different (a VSL is intended to be read aloud, whereas a newsletter is intended to be skimmed quickly and quietly in someone’s inbox).

So, if you’re a beginner, I would recommend experimenting with as many different copywriting opportunities as you can. Because each “thing you write” will teach you something that will make you a better copywriter overall.

But eventually, you will want to specialize. Not forever—you can always “change your specialization” later. But for periods of your career, you will see more rewards by specializing in one specific type of copywriting, or creating one specific type of asset, because then you’ll start to become known as the go-to-person for that specific thing.

Practice Recommendation: Do free work. There is no faster, more effective way to experiment and power-level your skills as a writer than to do free work. And by the way, I drink my own Kool-Aid here. Whenever I am trying to learn a new skill, the first thing I do is ask around for opportunities where I can help other people for free—just to get some reps in, experiment, and learn.

Skill #3: Industry & Business Model Expertise

The same way different copywriting assets have different structures, pacing, and rules, so do copywriting assets for different business models in different industries.

For example, writing a persuasive newsletter in health & wellness is very different than writing a persuasive newsletter in financial services. Why? Because there are actually laws in health & wellness about what you can and can’t say as it relates to the promised benefits or outcomes of health products. And those laws are different from financial services laws about what you can and can’t say as it relates to promised financial returns.

These industry-specific nuances are more important and valuable than most copywriters realize. In fact, when you are being hired as a copywriter, this is arguably 50% of the value you provide. Which is why you want to avoid “bouncing around” copywriting any asset for any company in any industry—because there’s no compounding of knowledge.

Practice Recommendation: Try to commit to one industry for at least 4 years. The more time you spend copywriting in a single industry, not only will you become more proficient but you’ll also become more in-demand. The “value of your value” will start to compound, because you speak the language.

Skill #4: The No-Sell Sell

This is a core principle I teach inside our Premium Ghostwriting Academy—because the truth is, many of the tried-and-true copywriting principles also apply to ghostwriting, and vice versa.

Bad copy is when you make the sale overt: “Buy now and save 20%!”

But great copy is when you make the sale feel like free education.

Dentists do an amazing job of this. I went to the dentist recently, and she was trying to sell me on Invisalign. Now, did she “sell me” on why Invisalign is so great? Nope. What she did was give me a 15 minute free consulting session on why my teeth were crooked in the first place, and all the bad things that were going to happen if I didn’t fix them.

“See this tooth right here?” she said, pointing to it on the screen in front of me. “This tooth is grinding against this one. And as they grind, that’s what’s causing your TMJ. And over time, this is also what causes your teeth to break down—which means, later in life, you will probably need to get a handful of root canals.”

The more she educated me on the problem, the more I started to sell-myself on the solution.

And at the end, the problem felt so visceral and urgent that I ended up buying Invisalign.

Practice Recommendation: Again, nothing will teach you more about how to write effective copy than trying to sell products or services yourself. And taking that a step further, nothing will accelerate your learning faster than phone or in-person sales. In hindsight, I think this is why I picked up copywriting so quickly. By the time I got introduced to the art of copywriting, I had already held 1,000+ sales calls and closed hundreds of ghostwriting clients on the phone. “Writing copy” was really just the same skill, except writing instead of speaking.

Skill #5: Objection Handling

Maybe the most important skill of all is learning how to anticipate the objections your target customer(s) will have—and proactively addressing them ahead of time (in your copy).

And over the years, I’ve come up with a very simple framework for how to do this.

After using copywriting to sell millions and millions of dollars of my own digital products, I have learned that all questions are really objections in disguise. “Will this work for me? Can I do this as a beginner? What do I do if something bad happens?” All of these aren’t actually questions—they’re objections phrased as questions.

Master copywriters then anticipate all of these objections by proactively answering these questions in their copy.

Practice Recommendation: This is where AI can be tremendously useful. Before you begin writing any piece of copy, you should have a firm understanding of all the questions someone might ask before, during, or after your “free education.” So, what should you do? Tell AI all about your target customer, and have it help you identify all the questions this sort of person would probably ask you if you were having this conversation with them in-person. Then, proactively answer their questions (and overcome their objections) in the writing.

Time Horizon

Like most forms of writing, copywriting is fairly easy to learn but takes a lifetime to master.

If you can sell even a single dollar’s worth of digital or physical products using copywriting, congratulations… you’re ahead of 99% of people. Because the truth is, the hard part isn’t really learning how to “write great copy.” The hard part is having the courage to put your reputation at risk and sell something in the first place.

Once you “start,” getting good is just a matter of practice. The more hours you put in, the more skill you acquire.

Over and over again, I am humbled by the “infinite game” that is copywriting. Every year, I feel like I’ve learned all there is to learn about writing effective copy, and every year I find some new nuance that makes me look back at all the copy I’ve written in the past and think, “Man, I had no skill back then!” That’s just how it goes.

But, to give you some reasonable expectations in terms of time:

• Year 1: $5k-$20k/mo: There is absolutely no reason why you can’t start making 6 figures as a ghostwriter and/or copywriter in your first year. And I will tell you (because I’ve trained a lot of these types of writers) the biggest bottleneck here isn’t the person’s “ability to write great copy.” It’s all the faulty beliefs they have around pitching clients, doing cold outreach, and pounding the pavement to find work. The writers who embrace the sales side make the most money. Everyone else sits on Upwork and waits for someone to pay them $10/hour.

• Years 2-5: $20k/mo - $40k/mo: Generally speaking, this is where the vast majority of ghostwriters & copywriters get stuck. And it’s a combination of lifestyle comfort (right around this level is when the desire to “work harder and make more money” starts to fall off a cliff for most people) and capped business model. Especially if you’re just working for yourself, it’s hard to get much higher than $30k or $40k per month because you’re constrained by time. You only have so many hours in the day, and you can only work with so many clients at a time.

• Years 5-10+ is Infinite: Most millionaire ghostwriters & copywriters don’t even begin reaching 7+ figures in annual revenue (personally) until the 10-year marker. Part of it is that it just takes a long time to develop that level of mastery. But more often than not, the “big change” writers see here in terms of income has less to do with writing proficiency and more to do with choosing a different monetization vehicle. Instead of getting paid to write copy for other people, for example, many of these copywriters decide to just start companies of their own—meaning their upside is infinite.

The Business of Copywriting

There are 3 things every single business on planet earth needs help with:

• Traffic: Letting more potential customers know you exist.

• Opt-In: Getting more potential customers on your email list and deeper into your educational/sales funnels—nurturing them to buy.

• Conversion: Getting more customers to buy.

So whenever someone says to me, “Cole, copywriting is so saturated, there aren’t any opportunities,” I know they are an uninformed beginner. Because the truth is, the amount of copywriting & ghostwriting opportunities in the world endless. Look around. Is your favorite restaurant down the street even running localized ads? Why doesn’t your friend’s e-commerce company have an abandoned cart sequence? Don’t you think the home page of that cold plunge company you were just checking out would convert better if it had a VSL from the founder?

Copywriting opportunities are everywhere.

Because every business wants to generate more traffic, get more potential customers on their email list, and turn more email subscribers into long-term buyers.

The Copywriter Business Model

As I explained earlier, there are a couple different ways copywriters can charge:

• Level 1: Effort - The most common business model for copywriters is to simply charge per hour, per month, or per asset. Said differently, you’re being paid for your time and effort. This isn’t a bad place to start, but if you want to make serious money as a copywriter then you will have to eventually ascend to Levels 2 & 3.

• Level 2: Revenue Share - This is where you can start earning hundreds of thousands, even millions of dollars as a copywriter. And the honest answer here is, “You get what you negotiate.” Every opportunity is different. For example, some companies like Agora Financial have an entire staff of master copywriters, each of whom they pay a revenue-share split based on performance. In other cases, you might be able to negotiate a much smaller revenue share with a solopreneur or small business owner—if and when you’ve proven yourself to be “indispensable.”

• Level 3: Entrepreneurship - Lastly, the real uncapped upside only occurs if you choose to take on the majority of the risk yourself. Now, it’s worth noting that a lot of times talented copywriters will skip Levels 1 & 2 and jump straight to Level 3. This is what I did. I had sold millions of dollars of my own products, writing copy for my own companies, before I had ever been hired to write for other people. (Your individual success also creates a flywheel of opportunity, because the more you achieve on your own, the more other people will want to pay you a premium to help them generate a similar result.)

Levels 1 & 3 are fairly straightforward, but I’d like to give a little more context on how Level 2 works.

When you are a copywriter negotiating a revenue-share deal, typically what happens is the following: first, the company gives you detailed metrics on how a specific funnel is performing, including current traffic and conversion rates. Then, you negotiate some sort of revenue share on the increased impact you have on that funnel above baseline metrics. So for example, if the funnel was converting on average at 10%, then anything above 10% could be attributed to “your efforts” and you would get paid a percentage of that upside. Industry standard as far as royalties go is anywhere from 10% to 50% of the upside—depending on how much leverage you have, and the sort of outcome you successfully generate.

Some rough math to show you how this works: if a funnel is doing $1,000,000 per month in revenue and converting at approximately 10% from the product’s landing page, then you could negotiate a revenue-share deal by rewriting the entire landing page and increasing the conversion rate to 20%. That “delta” between the 10% conversion rate the company had before, and the 20% conversion rate you are responsible for driving, is then what you would get paid on.

I will tell you though, from my experience, these types of revenue share deals are very relationship & reputation driven. You won’t find these opportunities on Upwork, or even by cold-pitching clients. Typically, these opportunities either come as a result of years working with a specific company or client, or your reputation attracting people who want to work with you, and only you.

Which is why most copywriters don’t start unlocking these opportunities in the first five, or even ten years of their careers.

My Recommendation

If you are a beginner or aspiring professional writer, I would pick either ghostwriting or copywriting.

Both of these career paths have the highest likelihood of increasing your income the fastest—because both are directly correlated to helping businesses make more money. With ghostwriting, you help companies and founders educate their target customers… which makes them more likely to buy… which makes the business more money. And with copywriting, you help companies “sell” their target customers… which means answering all their questions (aka overcoming all their objections)… which makes them more money.

Both of these are amazing career paths to use to power-level your skills and your bank account.

Furthermore, the reason I would advocate for every writer to study copywriting no matter what career path they choose is because copywriting is all about psychology, and psychology is the secret to all great writing.

You are in the business of “selling” readers on your ideas.

Dear Reader,

Back in January, 2025, I flew to Las Vegas to attend Alex & Leila Hormozi’s Acquisition.com Workshop Event.

I wrote up a full review of the workshop event here. (Nutshell: It was awesome.)

At the end of the event, we decided to double-down and buy their upsell: two advanced small-group workshop events with their portfolio team later in the year. This is the same team of people responsible for scaling the various departments of all the portfolio companies they invest in—several of which have crossed the $100M mark. It was $35,000 (at the time… I hear they’ve since raised the price, as they should), and included a full deep-dive analysis of your business.

Well, it’s now March, 2025, and I’m writing this in the lobby of the Wynn Hotel the day after we attended our first small-group event with their portfolio team.

First, I’m going to do a quick recap and review of the event.

And then I’ll get into crystallizing my messy notepad of takeaways here for you.

Acquisition.com VAM Workshop Review

I am a big believer in investing in yourself.

So much so, that over the past few years I have invested north of $300,000 in education programs, workshops, and masterminds to help accelerate the growth of our writing businesses. That probably sounds ludicrous to most people—and if you don’t have a business vehicle into which you can pour said knowledge, you would be right.

But here’s what I know:

1. All of my mentors do the same thing. Many of them still, even after building $100M and $1B+ companies, continue to spend $250,000 - $500,000 per YEAR in continued education and keeping their finger on the pulse.

2. You can make every investment ROI positive. Oftentimes, you aren’t just buying information that will help grow your business. You’re also buying access to serendipitous knowledge “you didn’t know you didn’t know.” You’re buying validation that what you think is the right next decision is the right next decision. You’re buying confidence in your ideas. You’re buying a sounding board to stress-test your ideas. Etc.

3. I’ve invested $300,000+ but made millions. We just crossed $15M in lifetime sales in just the past 4 years. (To be honest, it’s actually closer to ~$18M because we also accept payments in other payment processing systems, but this Stripe screenshot below is nice and clean so we’ll go with that.) If you gave me the option to save that $300k and still generate the same end outcome, but it would take 5 more years… I’d trade the $300k every time.

Now, do you NEED to do this? Do you NEED to invest this much in yourself?

Of course not. The Internet is free, as are most AI tools.

And if you’re just starting out, don’t have a business, and don’t have any (or very much) revenue, then spending $35,000 for an advanced workshop is probably unnecessary.

But as you get going, I think it’s one of the best things you can do for yourself and your business.

Some napkin math:

• $35,000 for this event

• Our business currently does approximately ~$6M/year in top-line revenue.

• That’s 0.5% of our revenue.

Do I think I’ll learn at least 1 thing that will grow our business by more than 0.5%?

If so, then it’s an ROI-positive trade.

VAM Offer Stack

“VAM” stands for Value Acceleration Method.

This is Acquisition.com team’s process for growing companies in their portfolio. The “pitch” to businesses who attend the entry-level workshop is: “This is exactly what we would tell you to do if we invested in your company.” Pretty compelling pitch, especially for businesses (like ours) who love learning from Alex & Leila Hormozi and their team.

I’m probably missing a bunch of things here, but here’s the high-level offer stack of the VAM Workshop:

• 2 events per year

• You choose the dates—but goal is to space them out by 3-6 months so you can make progress, come back and ask more questions, make progress again, etc.

• You work individually with the best person on their portfolio team who can help you solve your specific constraint in your business (marketing director, sales director, hiring director, etc.).

• That portfolio team member also puts together a full analysis of your business + in-depth slide deck on all the upgrades / changes they would recommend to remove the core constraint in your business so it continues to grow.

• We paid $35,000 but I know they’ve raised the price since, and will probably continue to raise the price because they have so much demand (as they should).

For example, right now our core constraint is on the CRO side.

CRO stands for Conversion Rate Optimization.

In a nutshell: we have plenty of traffic, but we are “leaking” a good amount of quality leads all throughout our funnel. Which means how we grow the business by 50% or even 100%+ from here isn’t some “big” strategy or game-changing idea. It’s just months of really, really boring work tweaking every single tiny variable in our funnel:

• How can we increase the opt-in rate of our landing page by 5%?

• How can we increase the number of leads who fill out an application for our Premium Ghostwriting Academy by 5%?

• How can we increase the number of leads who fill out an app but haven’t booked a call by 5%?

• Etc.

This is the process of going from $5M to $10M.

It’s not some big change. It’s just a million tiny tweaks that slowly but surely allow for more throughput in your funnel—grinding the business up to the 8-figure mark.

So, for $35,000 here’s essentially what we bought:

1. We bought someone smart telling us that. Which, to be honest, we didn’t know.

2. We bought someone smart telling us WHY we should do that. Also very important, because there are currently 8,754 other shiny objects trying to distract us right now, so having clarity that “this” is the only thing that matters to really grow the business is monumentally helpful.

3. And we bought someone smart telling us HOW we should do it. We bought the ideal scene, teleporting us into the future. Now we know what to do, why it’s important, and how to immediately start making these changes.

I would be shocked if we don’t hit 8 figures in revenue this year.

Again, laughable ROI on the 5-figure investment we made.

To Recap:

• Workshop was amazing.

• If you’re below $1M in revenue, I’d recommend the entry-level workshop.

• And if you’re above $2M in revenue, I’d recommend investing in this more advanced, small-group workshop.

We’ll be back in Las Vegas in September for our second event—and hopefully, we’ve made all these improvements by then (we will) and we can get to work on removing the next constraint in our business, taking us into multi-8-figure territory.

For what it’s worth: years of being a ghostwriter has allowed me to talk to a LOT of very smart people in business. Founders of billion-dollar companies. Insanely successful Venture Capitalists. C-level executives at some of the largest publicly traded companies in the world. You name it.

And truthfully, I think Alex & Leila are the best at creating business frameworks.

A lot of people are good at the game of business. But not very many can articulate how to replicate that success in a reliable way.

Can’t recommend entering their ecosystem enough.

5 VAM Workshop Golden Nuggets

So, with all that in mind, what are some of the biggest things I learned?

Honestly, a lot of it was stuff I know I know, I just needed to hear again. And that’s OK. Sometimes you need to hear the same thing 10 times, in 10 different ways, from 10 different people in order for it to finally “click.” This is what so many people don’t understand about education, and the art of learning: just because you “heard” it doesn’t mean you learned it.

You’ve only “learned” once the learning successfully changes your behavior.

So until then, find more ways to hear it again.

1. The 4 Levels of Growth ($0 to $100M)

I found the distinctions between these levels really interesting & pretty spot-on to what we’ve personally experienced:

• (Level 1) $0 to $1M: Validating the core product/service. If you can’t cross $1M/year with the core product/service, something about it isn’t working. Could be the marketing, but it also could be the offer or the business model. Something is broken.

• (Level 2) $1M to $3M: Don’t get distracted. We experienced this so much at this level. Once you cross $1M you think “I can do everything!” And you can’t. You can do ANYTHING, but you can’t do EVERYTHING. Sequence matters. And the reason most people get stuck here is because they allow themselves to get distracted—instead of just taking the core product/service that is clearly working and pumping as much marketing volume into it as possible.

• (Level 3) $3M to $10M: People. Above $3-5M/year, chances are, your team has grown to a point where you are FAR more reliant upon other people. Long gone are the days where you (the founder/creator) could just grind for a weekend and have a meaningful impact on the business. Now, it’s about empowering other people to build with you—and trusting them to get things done on their own, the right way. (This is where we are right now.)

• (Level 4) $10M to $100M: Hiring subject matter experts who know way more than you do about a specific vertical in the business. Prior to $10M, a lot of times the founder/creator will play a role within the business, learn it, figure out how they want it done, and then hire someone else to “manage” it. But more and more, I’m seeing how/why that doesn’t make sense the bigger the business gets. Above $10M, you don’t build new departments yourself. You don’t know how! And you now have the cash flow to go hire someone who has already spent 10-20+ years doing the exact thing you want to go build. Go hire & empower that person for each vertical within the business.

“You just need to hire great people” is one of those things you hear successful people in business say over and over again, but it’s hard to really grasp what that means until you experience it yourself.

2. Employee Retention Framework

This is something I’ve always know intuitively, but it was really helpful to hear someone articulate this in a way that was tangible.

Employees need to be constantly re-sold on the vision of the business, and their individual vision inside the business.

3 ways you can incentivize team members longer:

• Mentorship: Give people the opportunity to learn things above and beyond their specific role.

• Identity: Give people ways to crystallize their own individual identity within the team, and can see the direct impact of their contributions to the larger whole.

• Leadership: Give people opportunities to experience leadership moments, even if it’s small—like leading a call, or being part of a presentation.

As our team grows, and we need to think more and more about “people,” I found this framework really helpful for creating systems that constantly reinforce each person’s role on the team (and how much we appreciate each individual person!).

A secondary framework I really liked here is changing how you reward team members with variability:

• Quickly: The moment someone on your team performs an action/behavior you want to reinforce, how can you quickly validate that action/behavior with validation, approval, or some sort of reward?

• Randomly: How can you reward team members with variability, so that rewards or validation don’t become “expected” and lose their value? *(Hedonic adaptation is real, and we tend to appreciate things that are “unexpected” more than things that are expected and eventually become boring.)

• Publicly: How can you celebrate different team members beyond just 1:1 interactions (on team calls, during department meetings, etc.) so their efforts are recognized by the larger whole?

3. How To Charge More

This is a framework I actively teach inside our Premium Ghostwriting Academy, but I heard an additional tactic here I really loved—which I’m going to steal :)

Whenever you are thinking about how to charge more for your product or service (but especially services), here are 3 ways to go about it:

• First: Set a date for when the new pricing will take effect, over-communicate, and raise prices. Go to all your clients and just tell them, “My business has been growing a lot. I’ve decided to raise prices to better reflect the value we provide. We’ll be adjusting our pricing on {Specific Date}. I’ve really loved working with you, so if you’d like to keep things rocking & rolling we can bump you up to our new pricing tier. And if this is out of budget, just let me know and we’ll work on a transition plan.”

• Second: A clever little tactic you can use to make your “new price” even more digestible is price anchor to something even higher and then downsell to the “real, new price.” For example, let’s say you want to raise your prices from $3,000 per month to $5,000 per month. Well, how do you make that seem like a steal? You say, “We’ve decided to raise our prices to $7,000 per month, but I’ve really loved working with you, so I’d be happy to meet you in the middle, give you a discount, and only increase your retainer to $5,000 per month.” You end up in the same place, but now it feels like a discount.

• Third: For long-term customers/people you genuinely like working with, down-sell them to keep the old price IF they pre-pay. This is the new tactic I hadn’t thought of, and really like. Let’s say you’re increasing your retainer from $3k/mo to $5k/mo. You can say to the client, “We’ve decided to increase our prices to $5k per month, but I’ve really loved working with you so I’d be happy to honor your original pricing if you pre-pay for the next 6 months.” This allows you to pull a ton of cash forward, AND takes the risk of them churning down to zero.

4. Ads 70/20/10 Framework

This is something I’ve heard Alex Hormozi talk about probably 10-20 times in his own content, but again… sometimes you just need to hear it again, in a different way, from a different person, for it to click.

As we look to scale our retargeting & cold traffic ads throughout the year, here’s the testing framework their portfolio team uses:

• 70% of ads = “more.” So just take the ads that are sort-of-working and create more, slightly different variations. This means tiny tweaks like: same ad, different filter; same ad, different background music; same ad, different person reading the script, etc.

• 20% of ads = “adjacent.” Take your best-performing ads and re-launch with a more meaningful change. The meaningful changes are usually “new hook” (first 3-5 seconds), “new CTA” (last 5-7 seconds), or “new/change social proof” (hook or throughout).

• 10% of ads = “new.” Only a small number of your new ads should be completely new. This is your experimental bucket. Just try things. And if something works, do “more” small variations. And then when you find a winning variation, do “more adjacent” variations.

A lot of boring work, but this is how you figure out which ads can scale to the moon.

5. Operationalizing Behavior Framework

This is one of my favorite Alex Hormozi-isms: unbundling words & operationalizing behavior.

Something they do internally, especially with sales training, is they give salespeople (in their own company, but also their portfolio companies) a massive checklist of all the “behaviors” they need to execute in order to have a successful sales call.

And they get super granular.

Literally things like:

• “Did you greet the prospect at the beginning of the call addressing them by name with excitement in your voice?”

• “Did you nod your head when the other person was talking?”

• “Did you show understanding by repeating the last thing they just said to you back to them?”

• Etc.

This might sound ridiculous, but it’s not. This is the level of detail beginners need.

Otherwise, what happens is you just say, “You need to be more confident…” and nobody knows what that means. “Confident” is a bundled term. And you need to UNBUNDLE it into actions in order for it to be understood and, more importantly, implemented—causing a change in behavior.

I’m going to look to create this internally for our own Sales & Success teams, but also create this for our ghostwriting students who are brand new to holding sales calls.

In Conclusion

Super fun event.

Excited to see how much we implement/grow over the next 6 months.

Pumped to be back here in September for the second small-group workshop event.

And onwards to $10M+ we go…!

Dear Writer,

So you want to be a Ghostwriter?

I started ghostwriting for founders and C-level executives in 2016—back when there was a stigma attached to the word. Hiring a ghostwriter sounded like you were somehow “cheating.” And still, despite that stigma, I very quickly went from making slightly above minimum wage to upwards of $20,000 per month as a full-time ghostwriter.

Today, nearly a decade later, and ghostwriting is one of the fastest-growing and most-popular jobs for writers (and the stigma is completely gone). So much so, that you can now find pieces in major publications like, “Want To Earn Six Figures As A Writer? Try Ghostwriting,” in the The Wall Street Journal, or “How A Ghostwriter Makes $200,000 Per Year Writing Tweets” in Business Insider.

There are 3 industry-wide tailwinds causing this surge in ghostwriting’s popularity as a career path for writers:

• Tailwind #1: Every day, more and more companies know they need to create content online. This tailwind started in the early 2000s and has been accelerating ever since. As the Internet grows in scale (and “eats” the analog world, turning it digital), so too does the number of companies that want to participate in this digital-first economy.

• Tailwind #2: Every day, more and more founders, business owners, executives, etc., want to build personal brands. This is a secondary effect of Tailwind #1. As the Internet grows, and more companies want to participate in the digital-first economy, the people who run or work within those companies also want to participate, scale their knowledge & insights online, and become known in the digital world. After all, people don’t want to hear from brands. People want to hear from people.

• Tailwind #3: Smart people are (increasingly) insights-rich and time-poor. Especially in the digital world where an hour can feel like a lifetime, a lot of the “game” for businesses (and their founders, executives, investors, etc.) is staying relevant, everywhere, all the time, forever. The problem is, the most knowledgable people in every industry usually are also the people with the least amount of time—meaning the only way for them to participate in the digital world is by hiring some help.

Aka: a ghostwriter.

Now, here’s where there’s a misconception.

Ghostwriting doesn’t mean “I write for you, and put words in your mouth, with zero oversight.” In fact, it’s quite the opposite. Ghostwriting is the art of saying what the client has already said, thought about, or clarified themselves, over and over again on the Internet. You use and re-use their own words to create new versions of their core, most valuable insights and ideas.

Remember: these people—founders, executives, investors with decades of experience—are insights-rich and time-poor.

Whereas you, the writer, are (usually) time-rich but insights-poor.

Which is what makes smart people & ghostwriters such a perfect match.

What about AI?

The next question people ask, whenever I talk about ghostwriting being such a lucrative opportunity for writers, is some variation of, “But what about AI?Why would a CEO hire a ghostwriter when they could just use ChatGPT?”

I’ll tell you why: because ghostwriting isn’t just about writing.

A lot of the value you provide as a ghostwriter is:

• On the front-end: Interviewing the client, coming up with high-quality & differentiated ideas, helping them clarify their thinking, etc.

• And on the back-end: Setting up and optimizing their profiles, connecting accounts, building email automations, segmenting lists, etc.

Considering most people don’t even know how to set up a basic filter in Gmail, do not underestimate how difficult all of these things are for the average person to execute—let alone a busy, time-poor executive or startup founder. (I’ve had ghostwriting clients tell me that our weekly content calls were so helpful that they felt like “business therapy” sessions.)

And sure, while there may come a point in time when you can open an AI tool and just say, “Make me a thought leader in my industry online,” and a hundred AI agents spring into action to do all of these things for you, we are still a very, very far away from that happening.

AI isn’t going to steal a ghostwriter’s job.

AI is going to make ghostwriters 10x more efficient and effective.

For Beginners: 7 Ways Ghostwriting “Pays” You

I have generated millions of dollars in revenue for myself as a ghostwriter.

But in all honesty, the financial side of this career path isn’t even its primary benefit.

I cover all of this in my book, The Art & Business of Ghostwriting, so here’s a compressed explanation of why I’m such a big fan of ghostwriting as a career path—particularly for beginner writers:

1. Ghostwriting pays you to learn.

Ghostwriting is sort of like going to school for free, except better. Because instead of learning passively from “a teacher,” you learn directly from someone who is actively doing that thing you want to learn about, at a very high level, in the real world. You get to learn from the source. You get to ask them any question you want. And then, you get to send them an invoice… and they pay you!

2. Ghostwriting pays you to practice.

As a beginner writer, your primary bottleneck isn’t money. It’s time. You need to rack up as many hours of practice as possible in order to “get good.” Which is why I strongly encourage beginner writers to start ghostwriting on the side (or, even better, become a full-time ghostwriter!) so you can get paid to practice. This is a much better strategy than working a non-writing job during the day and only having 1-2 hours to “get good at writing” each night.

3. Ghostwriting pays you to build a network.

I am not exaggerating when I say that because of ghostwriting I now have a multibillion-dollar network. If my entire life burned down and I needed a job tomorrow, there are hundreds of founders & CEOs I could call and ask for an opportunity—because they all used to be my clients. If I wanted to raise money for a new venture, there are hundreds of angel investors, venture capitalists, and high-net worth individuals I could call—because they all used to be my clients. If I was trying to get connected with someone, get access to an exclusive event, or even just needed advice on a business decision, there are hundreds of smart people I could call—because they all used to be my clients.

4. Ghostwriting pays you to know about trends early.

I’ll give you a crazy example. When I was 26 years old, at the very beginning of my ghostwriting journey, one of my first ghostwriting clients was a cryptocurrency entrepreneur. The topic of our first article together was on the future of Ethereum—back when ETH was approximately $20. By the end of our content call, not only had I learned a tremendous amount about this new technology, but I had “found out” about Ethereum before the masses. I got off our call and was so convicted in the technology that I bought $20,000 of it—almost all of my savings at the time. But 2 years later, as crypto started taking off as an industry, that $20,000 turned into $250,000. Not a benefit I expected from ghostwriting!

5. Ghostwriting pays you to experience different lives.

I’ve ghostwritten for billionaires. I’ve ghostwritten for some of Silicon Valley’s most successful tech entrepreneurs. I’ve ghostwritten for quirky venture capitalists, ego-maniac founders, socially awkward CIOs, cutthroat executives, Grammy-winning musicians, Olympic athletes, New York Times best-selling authors, you name it. And every time I would ghostwrite for someone new, I would see the world in a slightly different way.

6. Ghostwriting pays you to learn how to write in different voices.

There is a trope in the writing world that one of the hardest parts about becoming a writer is “finding your voice.” Well, here’s what ghostwriting taught me: you don’t “find” your voice. You create it. After ghostwriting for so many different types of people, in so many different industries, I’ve learned that “voice” is really just a combination of variables—tone, vocabulary, formatting, structure, etc. And as you master each one, you become more capable of creating any voice you can imagine, including the voice you desire most for yourself.

7. Ghostwriting pays you to write about topics you’re passionate about, but don’t have the credibility or experience to write for yourself (yet).

Finally, ghostwriting is sort of like being an actor… except on a page instead of a stage. You get to write about all sorts of things you probably never considered writing about yourself. For example, I love personal finance. I love learning about money and investing. But I never (especially in my 20s when I was broke) thought of myself as someone who could write about those topics because I wasn’t an expert, hadn’t made millions of dollars, etc. But as the ghostwriter of a millionaire FinTech entrepreneur, or real estate investor, or venture capitalist, I could.

The Art of Ghostwriting

So, how do you become a ghostwriter?

The first thing you need to understand is there is a direct correlation between how many different skills you bring to the table and how much you get paid. This is true for just about any job in modern-day society, but it is especially true in the world of ghostwriting.

In order to be a successful, well-paid writer or ghostwriter, you can’t just “be a good writer.” That’s not enough. And there’s a reason why we train writers on all of these skills inside our Premium Ghostwriting Academy.

Because you must be more than a writer—which means acquiring the following Hard & Soft skills.

The Hard Skills

There are 5 Hard Skills every ghostwriter needs in order to be seen as a trusted collaborative partner and not just a “hired hand” freelancer:

1. Project Management

2. Interviewing & Idea Generation

3. Writing (In Their Voice)

4. Platform Expertise

5. Technology Expertise

Let’s walk through each one.

Project Management

Freelance Writers make such little money because they act like low-level employees, waiting for the client (the “boss”) to tell them what to do.

Premium Ghostwriters do the opposite. Writing is just a small part of their value. They also act like Project Managers—taking the client by the hand, walking them through their process, over-communicating and giving them reassurance all along the way. If you want to know why Premium Ghostwriters tend to make significantly more money than Freelance Writers, this is a big reason why.

Because they don’t act like “freelancers.”

They act like 1-Person business owners.

Interviewing & Idea Generation

Next, most people don’t know what they want to write about—smart, successful, wealthy clients included. And even if they do, most of the time they have very little clarity over how to communicate their ideas well. The vast majority of the clients I’ve worked with, including some of the smartest people I’ve ever met, true industry experts, couldn’t wrap their heads around how to organize a very simple 800-word article on one specific topic.

Which is why your value as a ghostwriter starts long before the writing.

It’s your job to help the client identify the right topics for them, based on their unique industry insights, credibility, or personal experiences, and then organize their ideas into content their target reader finds value in consuming.

Writing (In Their Voice)

Third, you have to consciously build the skill of writing well in other people’s voices.

It doesn’t matter if what you write is smart, or compelling, or valuable… if it doesn’t sound like the client. And trust me, they will let you know. They will come back to you and say, “This doesn’t sound like me.” And if you don’t have clarity over what they mean, you’re not going to keep that client for very long.

Now, luckily, learning how to ghostwrite in other people’s voices is a pretty easy skill to build—if you know what to look for. I explain this in-depth in my book, The Art & Business of Ghostwriting, but here are the sparknotes.

The vast majority of clients can be reverse-engineered into these 5 archetypal voices:

• The Storyteller: Someone who speaks primarily in stories. You can recognize this voice by cues like, “You know, back when I was building my first company…” or “Let me tell you about the first time I…”.

• The Opinionator: Someone who speaks in strong opinions. You can recognize this voice by cues like, “I just think it’s crazy that…” or “Something a lot of people get wrong is…”.

• The Fact Presenter: Someone who leans on research or data to back up what they’re saying. You can recognize this voice by cues like, “According to Harvard Business Review…” or “Did you know that 47% of consumers…”.

• The Frameworker: Someone who speaks logically, step by step. You can recognize this voice by cues like, “If I was trying to build an app, there are three things I would do…” or “Here’s a reliable framework for making hard decisions…”.

• The F-Bomber: Someone who leans on expletives and controversial language to make their point. You can recognize this voice by cues like, “The number one rule I have at my company is Figure It The Fuck Out…” or “Stop bitching and start working.”

I’m sure, even with just this little bit of explanation, you can recognize who in your life—family members, friends, your boss or manager, or any of your existing clients—fits one of these five archetypes.

This is the first key: knowing how to recognize which archetype is the client’s voice. The second key is knowing how to replicate that voice over and over again for every client that fits that specific archetype.

Platform Expertise

Fourth, the ghostwriters who earn the most money specialize—either by service or by platform (or both).

This is because writing on LinkedIn is different from writing on X, which is different from writing on Medium, which is different from writing on Quora, which is different from writing thought leadership articles on a company’s blog, which is different from writing free newsletters, which is different from writing paid newsletters, and so on. Each type of writing, on each platform, you should think of as a slightly different version of the Digital Writing language—sort of like how both America and the United Kingdom speak English, but use different words, with different meanings, spoken in different accents, with different pronunciations.

So, pick a platform. And become the go-to ghostwriter for that specific platform.

Technology Expertise

And fifth, building on the above, is your ability to not just write… but scale your client’s library of work using technology.

This means not just having proficiency over a platform, but living at the cutting-edge and constantly experimenting with new ways of writing, publishing, scheduling, and tapping into the viral formats of the moment.

Especially in today’s digital-first, AI-forward world, this is a skill that requires constant evolution. Just because you know how to use a specific social platform, email marketing tool, or website builder today doesn’t mean you will know how to use it tomorrow (or that it will even remain relevant!). These tools and platforms are constantly changing—which means you need to remain curious and open to changing with them.

The Soft Skills

In addition to the Hard Skills, there are 3 Soft Skills that separate the highest-paid ghostwriters from the mediocre ones:

1. Close Listening

2. Radical Honesty

3. Information Advantage

Over the years, I’ve learned these Soft Skills play a massive role in how long clients decide to work with you, and the degree to which they let you into their lives.

Close Listening

A brutal truth in life is that most people don’t listen.

When you are talking, the other person isn’t really hearing you. What they’re hearing is their own thoughts interpreting what you’re saying and trying to decide what they should say as soon as your mouth stops moving.

“Close Listening,” on the other hand, is an almost meditative practice. You have no inner monologue fighting for your attention. You are completely tuned-in to the other person: what they’re saying, how they’re saying it, but most importantly, what they’re not saying.

I truly believe this Soft Skill is the reason why I was able to ghostwrite for such insanely successful, high-profile clients at such a young age. Because I listened. Unlike even seasoned writers, journalists, and publicists twice my age, I didn’t “try” to listen. I didn’t wait for the client to stop talking so I could say something that showed them how smart I was, too. I just listened, mirrored back to them what I had heard, and helped them clarify their own thinking.

Having this skill feels like a cheat code in life because so few people have it (or chose to consciously develop it), but everyone values it.

If you can listen, closely, people will open their entire world to you.

Radical Honesty

Another unfortunate reality about the business world is that most people don’t tell each other the truth.

If a client is being difficult, most freelancers just bite their tongue and say, “You’re right.” If a client has a bad idea, most agencies just validate their egos so they can keep the retainer payments coming in. These bad habits make things easier in the short term, but always lead to long-term condemnation.

Which is why, whenever I am mentoring other writers and ghostwriters, this is the rule I tell them to live by: It’s the client’s money, which means it’s the client’s final decision. But it’s your responsibility to tell the truth.

The faulty belief here, and why so many freelancers and agencies struggle with this, is because they think “going against the client” is what leads to conflict. And the vast majority of the time, it’s the opposite.

Telling the client the truth, and doing so with compassion, is what earns their respect.

Information Advantage

The last skill to build, and this is where all the compounding happens, is having an Information Advantage in the industry you’re writing within—which is really just a fancy way of saying “having a personal interest.”

For example, imagine you are a ghostwriter but, as a hobby, you’re obsessed with aviation. You love planes. You love watching aviation videos on YouTube. You’re constantly researching planes for sale on secondary markets, just for fun. And then one day, you find yourself at a dinner party… and the person next to you is an entrepreneur working on a new piece of aviation software technology.

Now, what are the chances you and that entrepreneur not only become instant friends, but naturally want to find some way to work together?

I’ll tell you: the chances are very, very high.

There is something magical that happens, especially in the world of ghostwriting, when a client in a specific industry sees you have a true personal interest in their same industry. Immediately, all traditional qualifications go out the window. They couldn’t care less about where you went to college, how many years you’ve been working as a ghostwriter, or any other fancy accolade.

Personal interest, and the result of that personal interest—which is an Information Advantage—trumps all, and is the reason why that sort of client will want to work with you, and only you.

Now, none of these skills are difficult to build. They just require conscious practice.

But again, how much you earn as a ghostwriter is directly correlated to how many of these skills you acquire.

Ghostwriting Is A Dividend On Your Talent

A different way of thinking about ghostwriting is like this:

All ghostwriting really is, is a dividend on your talent. It’s a way for you to monetize skills you already have, or are actively building on your own as a writer.

• If you write short-form content for yourself on X or LinkedIn, you can monetize that skill by ghostwriting short-form content for other people on X or LinkedIn in your industry.

• If you have a weekly newsletter, you can monetize that skill by ghostwriting newsletters for other people in your industry.

• If you write articles on Medium, or answers on Quora, you can monetize that skill by ghostwriting thought leadership articles for other people in your industry.

• If you write books, you can monetize that skill by ghostwriting books for other people in your industry.

• Etc.

All you have to do is offer the skills you’re already practicing on your own, as a service to other people, and you will double or triple your income.

Easily.

Case Study: Neil Strauss

Neil Strauss is one of the best examples of what it looks like to be a writer who collects a dividend on their talent through ghostwriting.

Strauss started his writing career out of college at an American news and culture publication called The Village Voice. From there, he went on to have his own Pop Life culture column at The New York Times, as well as land a contributing editor role at Rolling Stone. He wrote cover stories on musicians and pop-culture icons ranging from Kurt Cobain to the Wu-Tang Clan.

This was in the late-90s and early 2000s, back when journalism was one of the leading Writer Career Paths. Of course, we all know the end of that story: by the 2010s, Facebook and digital media had started eating the world, magazines started shutting down, and newspaper sales started falling off a cliff; and by the 2020s the career path of being a freelance journalist and contributing writer had been put out to pasture. Today, the vast majority of these writers have either been let go, plateaued, or forced to change career paths altogether.

Strauss, on the other hand—whether he saw where the world was headed, or was simply following his curiosity elsewhere—decided to explore other career paths much earlier than many of his peers.

By the early 2000s, he had already co-written/ghostwritten books like The Long Hard Road Out of Hell, an autobiography with Marilyn Manson; The Dirt, a collaborative autobiography with Mötley Crüe; and How To Make Love Like A Porn Star: A Cautionary Tale with Jenna Jameson, taking his journalism skills but bringing them into the more lucrative world of books.

He also began writing “Gonzo Journalism” style books of his own—his best-known work (and one of my favorite books, ever) being The Game: Penetrating The Secret Society of Pickup Artists. It is an investigative reporting memoir of Strauss’s multi-year journey into the “seduction community” where men share psychology strategies to pick-up women. The book, published in 2005, quickly became a New York Times best-seller, and a year later Sony optioned the rights to turn it into a film.

Today, not only is Neil Strauss one of the best-known non-fiction authors in the world, but he is also one of the highest-paid ghostwriters for celebrity memoirs.

In fact, you have probably read his most recent work and didn’t even know it was him: Rick Rubin’s best-selling book, The Creative Act.

Time Horizon

Your time horizon for success as a ghostwriter depends heavily on three variables:

• Which service you want to provide

• Whether you want to get paid in status or money

• And the degree to which you build your own credibility as a writer along the way

Let’s walk through all three, and I’ll explain why:

The Service

Of all the “written” services a ghostwriter could provide, books are the hardest: the hardest clients to find, the hardest clients to land, the hardest projects to execute, the longest to complete, etc.

Conversely, learning how to write short-form LinkedIn posts or weekly newsletters for a business owner isn’t very hard. It’s an easy skill to learn, and clients are everywhere.

So your time horizon for both “success in general” (which we should really call Status) and profit is dependent upon which service you want to provide, and for whom.

Speaking from experience here, book ghostwriters (especially for celebrities and mega-high-profile CEOs) tend to receive the most status. They also get paid the largest lump sums of money. It’s very common for someone at Neil Strauss’s level to get paid anywhere from $250,000 to $2,000,000 to ghostwrite or co-author a book. And at first glance, that might seem like an exorbitant amount of money… until you ask the question, “Over what time horizon?”

Most book projects take anywhere from 2-4 years to complete.

So $300,000 seems like a lot of money until you divide it by three and realize you could have made a whole lot more than $100,000 per year as a ghostwriter providing easier, more efficient services.

Which is why, instead of pursuing books, I encourage every ghostwriter to provide one or multiple of these three services:

• Educational Email Courses

• Weekly Newsletters

• Social Content

These projects are easier to land (much easier than convincing a high-profile celebrity to trust you to write their memoir), much easier to execute, and almost always more profitable.

Status vs Money

The next variable is whether you want to get paid in Status or Money.

When I was living in Los Angeles in my late-20s, I did a lot of ghostwriting projects that didn’t pay me very much money (many times, not at all), but paid me tremendously in status. I got to go to dinner parties in Hollywood Hills I never otherwise would have been invited to; I got to attend VIP events, drive sports cars, and hang out with mega-millionaires; and I got to listen in on conversations that were way above my pay grade.

You can unlock a tremendous amount of status as a ghostwriter because, when you are someone’s “ghostwriter,” they inherently want you around them—a lot. They want you to “soak up what they know.” They want you to become familiar with their world. And the more high-profile the client, the more incredible (and sometimes, insane) their world can be.

It’s very cool.

Now, the con of getting paid in Status is that status-doesn’t-pay-the-bills.

At a certain point, you will have to decide which is the priority: whether you want to work with someone because of who they are, who they can introduce you to, what you can learn from them, etc.… or what they’re willing to pay you.

My personal take here is that you want a bit of both. You need to make a living, but you should also reserve 10-20% of your capacity for clients whose value extends beyond “just money.” Some of my favorite clients, and the ones who taught me the most about business, were clients I worked with at a discount (or in some cases, for free) simply because I wanted to learn.

Your Own Credibility As A Writer

Neil Strauss has ghostwritten for Rick Rubin.

Mark Manson has ghostwritten for Will Smith.

Tucker Max has ghostwritten for Tiffany Haddish.

Notice a trend?

The more successful you become as a writer on your own, the more other successful people want and trust you to be their ghostwriter. And this isn’t just true for books. I know writers in every possible vertical—sales copywriters, social media writers, newsletter writers, content writers, you name it—who, because of their success in their respective vertical, get hit up constantly from other people wanting help doing that same thing, for themselves.

Which is why I like to think of ghostwriting as a dividend on your talent.

Whatever you’re good at writing, for yourself, I promise, there are hundreds of thousands, if not millions of people out in the world who would love to pay you to help them do the same.

The Business of Ghostwriting

How do ghostwriters make money?

There are three ways most ghostwriting projects or retainers get structured:

1. Flat-Rate, Per Project

2. Monthly Rate, Per Recurring Service

3. Up-Front Cash, Plus Performance Upside

Let’s walk through each one.

Flat-Rate, Per Project

Some ghostwriting services provide the creation of an asset with a clear end point.

For example, the primary asset we train ghostwriters on how to write, build, and sell inside our Premium Ghostwriting Academy is a 5-Day Educational Email Course—which is a high-value opt-in for businesses and/or people with personal brands to capture customer emails. This is an asset that takes about a month to build, but then can run via email forever. And for this project, we recommend ghostwriters charge a flat rate of $5,000.

Whenever you’re ghostwriting fixed assets that don’t have any sort of recurring nature, charging a flat-rate per project is the way to go.

Here are some other ghostwriting projects where a flat-rate makes sense:

• Website Copy: Once the website copy is created or “fixed,” the project is usually considered done. You don’t need to “keep creating” or “keep fixing” the copy every month, month after month.

• Automated Email Sequences: Things like Upsell Sequences, Book-A-Call Sequences, Abandoned Card Sequences, etc. Once one of these sequences has been created, it usually doesn’t need to be continuously tweaked. It’s done, it’s created, and now it’s running on autopilot.

• eBooks or Books: These are projects with clear end-points. Once the book is “done,” you don’t continue to tweak and re-write it over and over again—which is why books are usually billed at a flat-rate.

Pricing

When you’re ghostwriting an asset with a clear beginning and end to the project, and you decide to charge a flat-rate, there are a couple nuances in how pricing typically works.

If the project is $5,000 or less, it’s standard for the client to pay 100% up-front. Work begins after you’ve received a paid-in-full invoice.

If the project is more than $5,000 (especially once you cross $10,000), it’s standard for the client to want to pay in installments—usually 50% at project kick-off, and 50% upon project completion. If you are charging for a project in this price range, I would encourage you to proactively offer this to the client as a show of good faith.

The project should have a clear end, measured either by milestone completion or time. Despite charging a flat-rate, it’s very common for these types of projects to “run on indefinitely.” So it’s very, very important that you establish when the project is actually deemed completed.

Monthly Rate, Per Recurring Service

Other ghostwriting services create recurring assets with clear deliverables but no clear “end point” in the engagement.”

(Some recurring clients churn after a month, and others stay with you for years!)

For example, after a ghostwriter in our Premium Ghostwriting Academy lands their first Educational Email Course client, we then show them how to upsell the client with two options:

• More Flat-Rate Projects: After a client has a high-value opt-in like an Educational Email Course, now they probably need a few automated email sequences. If they are a services business, they probably need a Book-A-Call Sequence. If they’re a digital project business, they probably need an Upsell Sequence. Etc. So the ghostwriter can extract more revenue from the client by upselling them on additional flat-rate projects (helping them solve the “next problem” in their business).

• Recurring Services: The other option, after a client has a high-value opt-in like an Educational Email Course, is to upsell them on recurring services. If the client needs to increase the amount of traffic going to their Educational Email Course, they probably need a Social Media Ghostwriter. And if the client needs to increase the number of free email subscribers who eventually convert into paying customers, they probably need a Weekly Newsletter Ghostwriter. Both of these services are recurring in the sense that, once you start creating social content or writing weekly newsletters, you don’t really ever want to “stop.”

Nothing “Recurs” Forever

Now, a common misconception is that “recurring revenue is better than project-based revenue.”

And in theory, that’s correct. Money coming in every month is better than having to chase down new money every month.

The problem is, even recurring revenue doesn’t “recur” forever.

Just because you sold a client on a recurring service—like Social Media Ghostwriting or Newsletter Ghostwriting—doesn’t mean they are now contractually obligated to pay you your monthly retainer, every month, for the rest of your life. What’s really happening is the client is re-selling themselves on that “recurring service” at the beginning of every month. If they are happy with the work, they stay on. And if they’re not, they leave. (And if you’re thinking, “But what if they sign a contract…?!” that doesn’t matter. They’re going to cancel, and you’re not going to sue them, and you’re both just going to move on with your lives.)

Both project-based services and recurring services have the potential to generate plenty of revenue for you as a ghostwriter.

So don’t rule out project-based services just because they aren’t recurring.

Pricing

The vast majority of recurring ghostwriting services fall in the $3,000 to $7,000 per month range.

• If you’re charging less than $3,000 per month for a recurring service, you are most likely undercharging. Not because you don’t have the skills, or the credibility. But because you have some faulty belief swirling around inside of you insisting you “can’t.”

• And if you’re charging more than $7,000 per month, it’s because you have some sort of other strong variable working to your advantage. You might have a huge personal brand with a ton of public credibility, or an insanely valuable network you’ve found a way to monetize, etc.

Best practice for these recurring services is to bill the client in-full at the beginning of the month (or whenever the engagement officially starts), and then every 30 days thereafter.

Up-Front Cash, Plus Performance Upside

Now, there is a third way to charge as a ghostwriter, and that’s some blend of up-front cash and long-term upside.

For the vast majority of beginner and even intermediate ghostwriters, not only are these kinds of opportunities rare, but I would discourage you from taking them. These are high-risk, high-reward projects. So until you’re in a strong position of financial independence, I would just take up-front cash and forgo any long-term upside. (For context, I have done dozens of these types of deals over the course of my career and I’ve only had one actually be ROI positive. The rest all lost me money and were a massive waste of time.)

But, just to future-pace a bit for you, here’s how these projects typically go.

Think of Up-Front Cash and Long-Term Upside as two different levers:

• Cash Up, Upside Down: If the amount of Up-Front Cash you receive for the project goes up (which means your “risk” in participating in the project goes down—since more of your compensation is guaranteed), then it makes sense for your Long-Term Upside to go down. The client is the one taking on more risk, which means they are entitled to more of the long-term rewards.

• Cash Down, Upside Up: If the amount of Up-Front Cash you receive for a project goes down (which means your “risk” in participating in the project goes up—since less of your compensation is guaranteed), then it makes sense for your Long-Term Upside to go up. You’re now sharing a larger chunk of the risk with the client, which means you are entitled to more of the long-term rewards.

Ghostwriting books as a service is a good example of this.

When you enter the upper-echelon of ghostwriting books, and you are a successful writer and have leverage of your own (like Neil Strauss, Mark Manson, etc.), you now have some negotiating power. Which means you could charge for the project in all sorts of different ways.

In this hypothetical example, and using round numbers, let’s say you typically charge $500,000 to ghostwrite a book for a celebrity.

• Option A: You could take all $500,000 up-front but forgo any back-end, long-term royalty. This would be zero risk for you but also zero long-term upside.

• Option B: You could take $350,000 up-front but ask for a 1% perpetual royalty on the back-end. This would mean putting $150,000 of your guaranteed compensation “at risk” for a chance at earning more than that in the future, based on the performance of the book.

• Option C: You could take $100,000 up-front but ask for a 10% perpetual royalty on the back-end. This would mean putting $400,000 of your guaranteed compensation “at risk” for a chance at earning much more than that in the future, based on the performance of the book.

• Option D: You could take $0 up-front but ask for a 50% perpetual royalty on the back-end. This would mean taking on the most risk, forgoing any guaranteed compensation but sharing equally in the long-term upside of the book.

There’s no right answer. It’s completely up to you how much risk you want to take on, and how much upside you think there is in the project.

You can also use these pricing mechanisms to structure much smaller ghostwriting deals, if you’d like. For example, you could reduce the amount of cash you take up-front for ghostwriting social media content, but create an incentive where you get paid $1,000 for each post you write that receives over a million views. Or, you could take no cash to ghostwrite someone’s paid newsletter, but share in the profits 50/50. Everything in life is negotiable.

But I will tell you this: in all my years doing performance-based deals, I’ve learned that the deals you want, people won’t give you; and the deals you don’t want, people will offer you all day long.

Which is why I tell ghostwriters, just take the up-front cash.

Case Study: Digital Press

“But Cole… is ghostwriting scalable?”

“But Cole… are there really clients out there who will pay me thousands of dollars?”

“But Cole… how am I supposed to get ghostwriting clients if I can’t talk about my work, and can’t use testimonials?”

Trust me when I say that, in the beginning, I had all of these same questions (and faulty beliefs) too.

In 2016, when I told one of my closest friends I had quit my 9-5 job and was making $250 per article ghostwriting for business owners, he didn’t believe me. He, like everyone else, pushed back and said, “Why? Couldn’t they just hire some freelance writer on Upwork for $20 per hour to do the same work?”

18 months later, and our ghostwriting agency had 80+ clients and 23 full-time employees (ghostwriters, editors, and salespeople), generating $180,000 per month in revenue.

Forget $250 per article—we got all the way up to charging $2,500 per article.

One of the hardest lessons I’ve had to learn in business is that anytime I think something isn’t “scalable,” it’s not because that’s true. It’s because I don’t believe it to be true, because I’m incapable of seeing the skill gap between who I am today and who I would need to become in order for “this thing” to be scalable.

I remember charging $250 per 800-word article and thinking, “This is crazy expensive.” Then I started charging $500 per article and thought the same thing. Then $800 per article and thought the same thing. Then $1,000 per article. Then $1,500. Then $2,000. Then $2,500.

You will always be able to find reasons why you shouldn’t or can’t do something. You could point to any product or service on planet earth and make a good case for why that thing can’t succeed or scale. But there’s a cliché saying in the business world that I’ve come to love over the years, and it goes like this: “If you want to be right, be pessimistic. If you want to get rich, be optimistic.”

Despite everything I’ve shared with you here, I’m sure you can think of 100 reasons why ghostwriting won’t work, or won’t work specifically for you. And you know what? You’re probably right.

But do you want to be right? Or do you want to get rich?

If you want to be right, you will talk yourself out of every opportunity.

If you want to get rich, you have to be willing to embrace the unknown, go on the journey, and figure out how to make it work for you.

My Recommendation

If you are a beginner or aspiring professional writer, I would strongly encourage you to start ghostwriting.

For three reasons:

1. Ghostwriting is your fastest path to $10,000 per month. No other Writer Career Path can get you there faster, with less risk. Ghostwriting requires no advanced skills, no huge audience, and no up-front costs to start.

2. Ghostwriting pays you to practice. Remember, your primary bottleneck to “getting good” at writing is time. How do you solve for time and money at the same time? Ghostwriting, where you can power-level your earnings and get paid to practice all day long.

3. Ghostwriting is a dividend you can collect on your talent for the rest of your career. The more successful you become as a writer yourself, the more your talent is worth, the more you can earn as a ghostwriter. It also makes your earnings more predictable, and your career more defensible. You will never go hungry as a writer.

Your big takeaway here should be: no matter what Writer Career Path you choose to pursue, you should consider double-monetizing it with ghostwriting.

Anything you get good at writing for yourself, you can get paid a premium to ghostwrite for other people.

The following is a bonus chapter from my forthcoming book, Writer Career Paths.

Dear Writer,

So you want to make as much money as possible, as fast as possible, do ya?

Well, not all Writer Career Paths are created equal. Each one pays you in different ways (status vs money), over different time horizons, with different ceilings. For example: some pay you faster but aren’t as scalable, whereas some are slower but compound like crazy.

As a reminder, the 9 Writer Career Paths for making $1,000,000+ are:

1. Literary Writer

2. Genre Fiction Writer

3. Non-Fiction Writer

4. Newsletter Writer

5. Content Writer

6. Ghostwriter

7. Sales Copywriter

8. Writerpreneur

9. Category Copywriter

So, let’s talk about which paths to pursue when, and why, to make the most amount of money as fast as possible as a writer.

Level 1: $0 to $1

Everybody wants to know how to make $1,000,000 before they’ve even made a single dollar.

Which is a mistake. Because the decisions you make to go from $100k/yr to $1M/yr are very different than the decisions you make to go from $0 to $1.

So, let’s start here.

In the beginning, broke aspiring writers like to believe their primary constraint is money. “If only I had a book deal” is probably the most popular of their self-acquittal nomenclature. In reality, money has nothing to do with it. Their primary constraint is time.

Which means, in the beginning, time is the variable to solve for—not making money.

Let’s walk through the logic:

• In order to earn money from your writing, you have to first “get good” at writing.

• “Getting good” at writing means you have to invest lots and lots of time into building the skill.

• But “getting good” at writing is only 50% of the game. The other 50% is “getting good” at monetizing your writing (the business side).

• And “getting good” at monetizing your writing means you also have to invest lots and lots of time into building the skill of monetizing your writing.

• All of which means you need to engineer a life that allows you to invest the most amount of hours-per-day possible into your pursuit of “getting good” at writing, as well as “getting good” at monetizing your writing.

It’s just hours.

So, in the most objective and unemotional way, if you say you want to become a successful writer (regardless of which Career Path you choose), and lots and lots of hours are required in order to get there, and your life isn’t engineered in a way that allows for more than 1 or 2 hours of writing per week (or per month!), then you aren’t going to reach your goal.

It’s not that you aren’t talented.

It’s not that you aren’t creative.

It’s literally just math. Pretend The-All-Knowing-Writer-Gods said, “If you reach 10,000 hours of ‘getting good’ at writing and 10,000 hours of ‘getting good at monetizing your writing,’ you will make millions of dollars. Guaranteed.” Pretend the outcome is fixed, objective, and measurable. Then, it’s just hours. Things like talent and creativity are irrelevant. (You can decide whether or not these things matter AFTER you’ve put in 20,000 hours.)

So, aspiring writer, what does it mean to engineer a life (and daily/weekly schedule) that optimizes for time?

3 Options To Power-Level Yourself

The way most people think to solve for “time” is by saving up a sum of money and throwing caution to the wind. They quit their job, run away to a cabin in the woods, and then spend 3 months in a state of stress, anxiety, and depression because they’ve given themselves a very small window of time to produce something genius that, they hope, will also (they’re not sure how, but they hope) make them millionaires so they never have to worry about money again.

This is a recipe for disaster, and rarely ever works.

Instead, here are a few options I’ve found that work much better, are lower stress, and increase the likelihood you accomplish your goal of “getting good” at writing:

Option #1: Work the most lucrative but lowest cognitive-load job you can find.

Part of why so many people struggle to find time to write is because their day-job is draining.

It’s not that they don’t have time when they get off work. It’s that they are so brain-fried that they need to spend those last few hours each night recovering (or coping) in order to endure the next day of work, and so on. And no amount of watching motivational YouTube videos about how you need to “just do it” solves the problem. Eventually, if “getting good” at writing is important enough, you need to consider finding a different job. And if this is the route you decide to go, you have to remember it’s not money you’re solving for—it’s time.

• Find a job that pays you the same as what you earn now, but is far easier and less mentally taxing. This will allow you to make use of those last few hours each night because you won’t be as drained from the day.

• Find a job that pays you the same as what you earn now, but is fewer hours. If the job you’re working now expects you in the office from 8am to 7:30pm every night, then finding a different job that is just 9-5 immediately gives you 3.5 more hours each day to invest in your writing. Huge upgrade!

• Find a job that pays you less than what you earn now, but is easier, fewer hours, and/or allows you to “practice on the clock.” If the job you work now requires you to be “on” all day, what might it look like to consider working a simpler job that doesn’t require as much from you? Like working the front desk of an apartment complex. I’m always seeing those guys sitting there on their phones with nothing to do. You could take that job and practice writing one, two, three, four more hours each day… on the job!

For example, this is what Brandon Sanderson, one of the best-selling science fiction writers in the world, did in his early years. After graduating from college, he took a job as the night desk clerk at a hotel because they allowed him to write while at work. These are the kinds of decisions you need to consider making if becoming a professional writer is “that” important to you.

There’s no right answer. However you get there is up to you.

But the point is, you have to solve for time, first.

Because if you can’t solve for time going from $0 to $1 as a writer, then even if I hand you $100,000 in cash tomorrow, you’re still faced with the same problem. You might be a little richer, but you’re still stuck—with no path forward to “getting better” as a writer.

Option #2: Get paid to practice.

The other option is to find a full-time job that is writing-related (if you’re not working one already).

Which essentially means getting paid to practice.

This is what I did.

My first (and only) job out of college was working for an advertising agency downtown Chicago. For the entire first year, I got paid to write social media content and blog posts for brands—like a local pizza chain, a burger joint, a coconut water company, and even a female gynecologist and sex-after-menopause expert (I learned a lot). The second year, I got paid to proofread proposals for website redesign projects, brand strategy retainers, even national brand campaigns. The third year, I got paid to write taglines, billboard ad copy, and the little blurbs that appear on a product’s packaging. And the fourth year, I got paid to run entire projects by myself, pitch and land clients, manage accounts, and even run accounting for my small department.

Now, was this job my be-all-end-all? Of course not.

It was very taxing, very demanding, and paid slightly above minimum wage. But I saw it as an opportunity to acquire all the same skills I was going to have to acquire anyways. I was getting paid to practice. And after 4 years of working at this advertising agency, when I finally decided to quit, I felt incredibly prepared for the real world as a writer, working for myself.

Option #3: Get paid to practice with a lucrative side-hustle.

The third option, and this is what I encourage most people stuck in a full-time job to do, is to get paid to practice by starting a lucrative writing-related side-hustle—aka Ghostwriting.

This accomplishes a few different things, all at the same time:

• First, it’s much easier than trying to find a new full-time job that pays you to practice. It just is. Easier to get started. Less mentally taxing. Etc.

• Second, it de-risks everything. A lucrative side-hustle means you’re less reliant on your full-time job; a lucrative side-hustle means you have a path forward incase you get laid off; a lucrative side-hustle means you can eventually quit your full-time job (unlocking even more hours to “get good” at writing); a lucrative side-hustle gives you more disposable income, faster, to reinvest in yourself or your future runway; etc.

• Third, it pays you to practice. More time spent writing is the goal. It doesn’t matter if you’re writing for yourself, or someone else. Writing is writing.

• Fourth, it holds you accountable. When you “work for yourself,” even on the side, you can’t talk yourself out of taking action as easily. Your clients will hold you accountable simply by having the expectation that you do what you said you were going to do. This forces a lot of quality hours of practice.

Which is why I tell every single aspiring writer the very first career path they should pursue is Ghostwriting.

Ghostwriting costs $0 to start.

Ghostwriting pays you to practice.

Ghostwriting can be done in addition to a full-time job.

Ghostwriting gives you a path out of your full-time job, allowing you to earn more AND reclaim more hours in your day (which you can reinvest in “getting good” at your own writing).

And Ghostwriting will hold you accountable. Watch how fast “Writer’s Block” evaporates when you have a client emailing you asking, “Hey, where’s that draft you said you were going to send me by today?”

The Big Mistake

Now, before we move on, here’s where people go wrong.

First of all, if any of the above makes you feel uncomfortable, good. Confronting the fact that, right now, your entire life is engineered AGAINST your goals as a writer is the first step. You aren’t getting in enough hours of “getting good.” And the solution isn’t telling yourself, “I know, I know, I just need to do it.” You won’t. You can’t. Because if you could, you would have done it already.

The thought of quitting your high-paying, high-status job for something that pays less and comes with zero status but might give you an extra 2-4 hours per day to work on your writing should be uncomfortable. Switching careers and trying to find a job that “pays you to practice” should feel scary. Even taking a job and saying to yourself, “I’m not going to care about getting promoted, making more money, or even pretending to be a productive employee—I’m just going to preserve my mental energy and write as many hours as I can in a day, on the clock or off” has an element of risk to it.

But that’s the point. And that’s what’s required.

Either you engineer your life with “getting good at writing” at the center of it, or you forever treat it as a hope and a dream and watch it never become a priority.

But the bigger mistake writers make, should they go through the hard work of engineering their lives with “getting good at writing” at the center, is they unlock more hours each day to write… and then fill them with non-writing activities.

• Scrolling TikTok

• Watching YouTube videos

• More time with friends!

• Etc.

Contrary to popular belief, the hardest part about becoming a writer isn’t making time to write. Because the decisions that unlock “more time” are all fairly logical. Again, it’s just hours. Right now, you don’t have enough of them. So go find a different job, or a less demanding one, or one that pays you to practice, etc.

The much harder task begins once you have the hours. Because now, you have to do something with them. This is where all the emotional stuff enters the equation:

• “I’m not good enough!”

• “What if people don’t like it?!”

• “What if the things I write don’t make any money?”

• “What will my parents, my friends, my siblings, my co-workers, my next-door neighbors think of me?!”

And the longer you sit in “all that free time,” the worse it gets.

In which case, 3 things happen:

1. The writer copes, and fills their free time with non-writing activities. They watch more movies. They scroll social media. They have the time, they just choose to squander it (but convince themselves that’s not what they’re doing the entire time).

2. The writer goes back to their old life. The discomfort was too much for them. They weren’t declared The Next Great Writer Of Our Generation in the first 24 hours, concluded they weren’t good enough (or the world had conspired against them), and now they can live the rest of their life in peace knowing they “tried.”

3. The writer gets to work. The only thing that makes the discomfort of all this free time go away is doing the thing you said you were going to do. And the flywheel goes like this: the more you write, the better you feel; the better you feel, the more you write; the more you write, the better you get, the better you feel, the more you write; and so on.

Going $0 to $1

Once you’ve solved for time—which might take a day or a year, depending on the way your life is currently engineered—now you can focus on making money.

Which means it’s time to go from $0 to $1.

Now, as far as Writer Career Paths go, all of them have the ability to make you a single dollar:

1. Literary Writer

2. Genre Fiction Writer

3. Non-Fiction Writer

4. Newsletter Writer

5. Content Writer

6. Ghostwriter

7. Sales Copywriter

8. Writerpreneur

9. Category Copywriter

But “money” on its own isn’t a very helpful metric. The real equation is money over what time horizon.

Because while it is possible to earn a dollar from all of these career paths, can you write a literary novel in 24 hours and put it up for sale? No. Can you write a Genre Fiction story in 24 hours and put it up for sale? Not a very good one! Can you write an entire non-fiction book in 24 hours and put it up for sale? No. You get the point.

So, in the beginning, and once you’ve solved for time (with “getting good at writing” at the center of your life), the next thing to decide is which Writer Career Paths have the highest likelihood of earning you the most money over the shortest time horizon—so that you can unlock the first life-changing milestone: earning $10k per month, consistently, as a writer.

Level 2: $1 to $10,000/mo ($50k Net Worth)

All 9 Writer Career Paths can make you money.

But these 6 take years to successfully monetize—because they require a higher level of skill and proficiency, and because they require a larger time investment in order to produce something you can sell:

• Literary Writer: Writing “good” literature requires the most advanced levels of proficiency, and literature as a category is one of the smallest markets in fiction, making it the hardest to monetize. Any writer who wants to “earn money” should prioritize this Career Path later in life—not when you’re first starting out and trying to pay your rent.

• Genre Fiction Writer: Genre Fiction is a giant category, making it very easy to monetize. But writing good, “addictive” fiction takes time. And more than that, all the Genre Fiction writers who make the most money also build audiences for themselves—which also takes time. So, high upside here, but too long of a time horizon. Not a great place to start.

• Non-Fiction Writer: The same goes for Non-Fiction Writers. To write a quality non-fiction book, you must either research a specific topic in-depth, or live that topic and build unique, differentiated frameworks from your experiences—both of which take time (usually years). Great career path for later, but again, too long of a time horizon to start making money now.

• Newsletter Writer: Newsletter Writers are really just digital-first versions of Non-Fiction Writers and authors. And knowledge aside, the real bottleneck to building a lucrative paid newsletter is having an audience online—which takes time. So again, great career path for later, but not very effective at generating money now.

• Writerpreneur: The same goes for selling digital products and being a Writerpreneur. Everyone thinks selling digital products is easy, but it’s not. You must first spend years acquiring some sort of Information Advantage, then build an audience online, and then acquire the skills of packaging and selling your Information Advantage in the form of a digital product. Amazing career path for later, but still not the fastest one for making money now.

• Category Copywriter: The most lucrative Category Copywriting opportunities are equity or stock-option deals with large publicly traded companies or heavily-funded startups. And the vast majority of the time, these opportunities come through direct relationships built over long time horizons. Again, amazing career path later in life, but very rare for beginners or even advanced writers to unlock in their first decade in the field.

If you notice, all of these Writer Career Paths have to do with creating products. Writing a book is a product. A paid newsletter is a product. Text and video courses are digital products. Category Copywriting is the exception. It’s a service, but much closer to “consulting” than actually sitting down and getting paid to “write lots of words” (like Ghostwriting, Content Writing, Sales Copywriting, etc.).

When you see creators online talking about how much money they make selling digital products (myself included), it’s easy to think this is the best way and fastest way to make money as a writer.

But it’s not.

The fastest way to go from $1 to $10,000 per month—the first big milestone you need to hit as a writer—isn’t by selling products.

It’s by selling services.

Which, if you notice, are the remaining 3 Writer Career Paths!

• Content Writer

• Ghostwriter

• Sales Copywriter

It is significantly easier to get 1 person to pay you $5,000 to help them build an Educational Email Course, or $3,000 per month to help them create social content or send a weekly newsletter, than it is to find 100 people to buy your $50 digital product every single month. And not only is it easier, but it can happen exponentially faster—because services don’t require you to invest tons and tons of time into building any sort of assets.

You don’t have to spend years building an audience.

You don’t have to spend years writing a book.

You can just reach out to people, point out a problem they have in their business, and then offer to help them solve it.

Now, I’m not going to cover the 100+ faulty beliefs people have here around being able to charge money for a service—like “I don’t have any credibility!” or “Nobody is going to want to work with me without having testimonials!” All of these are wrong and self-inflicted, and if you’d like help overcoming these faulty beliefs, I’d love to work with you inside our Premium Ghostwriting Academy.

The point is, your fastest path to consistently generating $10k per month as a writer isn’t by selling products.

It’s by selling a service.

Solve For Time… Again!

Now, why is $10k per month such a huge milestone?

Well, for starters, according to 2022 data, only 18% of Americans make over $100k per year, and only 34% of US households make a combined $100k per year or more. So if you are consistently generating $10k per month, not only is that an incredible outcome as a writer… but that’s an incredible outcome, period.

Second, if you’re working a full-time job and are able to consistently generate ~$10k per month on the side (as a Ghostwriter, for example), this is the point at which it starts to get harder and harder to rationalize keeping your full-time job. Not just from a financial upside perspective, but again, from a time perspective. How much more could you not just earn, but practice, if you had 8 more available hours each day? (And if you’re reading this thinking, “Who in the world could possibly generate $10k per month with their Ghostwriting side-hustle, while working a full-time job?” I can tell you we’ve seen it happen over and over again inside our Premium Ghostwriting Academy. So yes, it’s possible.)

Third, $10k per month is usually where you start to feel financially “safe.” Because unless your spending has accelerated as much as your income, you should be in a position to save an extra $1-2k per month—which is where the compounding begins. For context, over 50% of Americans have less than $500 in savings, which means you’re now on the path to outpacing the majority of Americans every single month, month after month.

But the real outcome, and why $10k per month is such an important milestone, is because this should be where you have both the confidence and financial cushion to bet on yourself. If you’re working a full-time job, quit. And if you’re already working for yourself, double-down. The thing you want to optimize for again is time.

• Can you quit your full-time job so you have 8+ more hours each day to write (or provide writing as a service, and get paid to practice)? If yes, do it.

• If you’re already working for yourself, how can you be more productive? How can you take on more clients? Or how can you work with fewer clients, at higher prices, to re-allocate more time to your personal writing?

• What other time-consuming responsibilities can you now “buy” solutions to? Can you hire a virtual assistant? Someone to clean your apartment or house? A part-time chef to help you meal prep for the week? How much more time can you reclaim to reinvest and double-down in accelerating your skills as a writer?

At this level, I promise, the extra $500 or $1,000 per month you save by not having an assistant, or a housekeeper, or a part-time chef, etc., isn’t worth it.

Solve for time. Solve for time. Solve for time.

Because the more time you have to “get good” at writing, and “get good” at monetizing your writing, the more money you will make, and the faster you will make it.

The Big Mistake

Now, here’s the big mistake writers make at this level—and I’ve watched it happen in our writing programs a thousand times.

The moment a writer starts generating ~$10k per month, shiny object syndrome kicks in, and all of a sudden, they want to do something different:

• “I should start a newsletter!”

• “I should start a YouTube channel!”

• “I should start creating digital products!”

• “I should create a different offer, for a different type of client!”

• Etc.

I’ve also mentored over 12,000 writers, so I can tell you why this happens.

First, the writer is euphoric. $10,000 per month is a lot of money. The first time I made $10k per month, I felt like the richest person on the planet. And if you hit this milestone in your 20s or even early 30s (before having a family, kids, “adult responsibilities,” etc.) the feeling gets compounded. You’re richer than all your friends, and all of your friends’ friends. And it’s in this euphoria you begin to think, “I can do anything!” (Big mistake.)

Second, the writer has some sort of faulty belief around the earning potential of the service they’re currently providing. If a single client leaves, you think, “My niche is saturated! It was a fad! It’s all over!” If a viral YouTube video pops-up on your home page from some guy talking about how he makes $800k per month working 4 hours per day, they think, “Omg! I’m doing it all wrong! I should pivot!” When you land a new client and revenue goes up, you think you’re a genius—and when you lose a client and revenue goes down, you think you’re an idiot. I call this the Genius-Idiot Rollercoaster, and riding it is just part of the growth process.

Third, the writer hasn’t gotten burned yet. When you’re on the up-and-up, you think you can do everything, pursue every idea, and never fail. But the moment your income starts to go down, watch how quickly you throw all those shiny-object ideas to the wayside—so you can refocus on the one thing that was making you money. The more times you get burned, the more you learn how hard it is to do one thing well.

These are all lessons you’re going to have to learn the hard way.

I can point them out. I can educate you about them, why they happen, and tell you what to do instead. But you’re going to make these mistakes anyways, and that’s OK. I made them too. The key is to recognize when you make them, and then get back to business-as-usual as quickly as possible.

Don’t chase something new.

Just keep doing what you’re doing—because if it got you from $0 to $10k per month, chances are, it can also get you to $20k per month or more.

Stack Net Worth To $50k

The last thing I want to note here, piggybacking on the importance of not getting distracted:

Every time you change something in your business, even if you think you’re changing it for the better, you are adding in a new element of risk. So when you hit $10k per month, you have to fight the impulse to start changing things. Because change is risk. And whatever you’re doing right now is working, so don’t change it.

Instead, just keep doing what you’re doing. Sure, look for ways to improve, but you want to reduce the amount of “big changes” you make to near-zero. You’ve finally built something that is working, and generating you serious money. Let it run! And don’t get in the way!

This was one of the biggest mistakes I made early in my career. The moment I hit $10k per month as a ghostwriter, I wanted $20k/mo. And the moment I hit $20k/mo, I wanted $40k/mo. And so on.

There’s nothing wrong with wanting to keep increasing your income. The problem (and the mistake I made) is when your pursuit of “more revenue” outpaces your ability to stack profit. Because in order to keep increasing your income as a writer, your business has to change, or your vehicle/career path has to change—which almost always means a period of reinvestment. Which means adding in new elements of risk. And if you don’t allow yourself to pause and “stack cash” at each level, that means your risk continues to climb but your financial safety net never gets built.

Which is what happened to me.

I scaled my ghostwriting agency from $0 to $180,000 per month in 18 months, never once taking profit off the table and letting my net-worth stack. I just kept reinvesting the profits back into the business in order to grow to the next level.

Had I slowed down, paused at each level, let my machine run and stacked some cash, I would have been a millionaire in my mid-20s.

Instead, I kept increasing my risk, built a multi-million dollar ghostwriting agency “on paper,” but had less than $10,000 in my personal savings account. And in the end, the business had grown so quickly and gotten so messy that I couldn’t sell it, and I was so burned out that I just decided to shut it down completely.

So, don’t make the same mistake I did.

As soon as you hit $10k per month in income, don’t worry about doing anything new. Take money off the table, de-risk yourself, and let your net worth stack until you hit ~$50k in liquid assets.

Then, move on to Level 3.

Level 3: $10,000/mo to $20,000/mo ($100k Net Worth)

Going from $10k per month to $20k per month is all about accelerating what’s working.

• Don’t change anything.

• Don’t start something new.

• Don’t say “yes” to that random opportunity your uncle called you about.

Just keep doing the thing that got you from $0 to $10k per month, better.

One of the big pitfalls people run into at Level 2 is hitting $10k per month by duct-taping three or four different income streams together: you’re a ghostwriter, you own a rental property, you run affiliate marketing for your cousin’s fitness coaching program, etc. And these people add insult to injury by thinking having multiple revenue streams increases their perceived value. They think it’s “cool,” and makes them seem like a seasoned serial entrepreneur.

In reality, it’s a neon sign announcing to everyone you have no clue what you’re doing (yet).

If the way you hit $10k per month is by combining a bunch of different income streams, you’re going to run into a brick wall when you hit Level 3. Because as a general rule of thumb: the higher you climb in income and net-worth, the fewer things you can do well. Anyone can figure out how to make a couple grand a month performing a service. What’s much harder, and why so few writers unlock the highest levels of income, is figuring out how to do one thing so exceptionally well that you have almost no competition and all the rewards go to you.

It has taken me a decade to learn this lesson. And the older I get, the more I realize how few things I actually need to do in life in order to be fulfilled, successful, and financially free… AND… how impossible it is to do more than one thing, well, at a time.

So, if you hit $10k per month by providing 3 different writing services (while simultaneously building your Airbnb empire), do not pass Go and do not continue on to Level 3. Clean things up. Pick one thing, and get that one thing to $10k per month.

Then, when you are consistently generating $10k per month and you’ve successfully put ~$50k away, move on to Level 3 and accelerate.

Don’t Change Career Paths!

In today’s digital-first world, there is absolutely zero reason why you can’t hit ~$20k per month performing a service:

• Content Writing

• Ghostwriting

• Sales Copywriting

The mistake writers make, again right around $10k per month, is thinking that now is the perfect time to “diversify” and start adding something different into the mix. Specifically: launching digital products.

No. No. No.

If you are at ~$10k per month and you add in something different, you have to realize you just slashed your productivity in half. Because now… you’re chasing two chickens instead of taking care of one. Which means there’s a switching cost. Which increases your stress and decreases your efficiency. Which almost always means you end up making the same amount of money you were making before, except with more headaches and less clarity on how to scale from here.

It’s a disaster.

Instead, you have to remind yourself that going from $0 to $10k per month was the hardest part. And most of the time, getting from $10k to $20k per month can happen in a fraction of the amount of time—if you do the right things, say “No” to any and all shiny objects, and stay focused.

The advice I give every single ghostwriter in our Premium Ghostwriting Academy is to not even entertain the idea of doing anything else until you’ve hit $20k per month.

And when you get there, realize that you’re now in the top 5% of earners in the world.

Let your machine run!

Don’t change anything, and don’t get in your own way.

Stack Net Worth To $100k

Getting to $20k per month is a monumental milestone as a writer.

And if you want to get there as fast as possible, and power-level both your skills and your net worth along the way, you should go all-in on providing a service.

But the real goal at Level 3 has less to do with income and more to do with net worth.

A couple things happen when you hit $100k in liquid assets:

• First, your ability to make long-term decisions goes up exponentially. You don’t have to make short-sighted decisions, or take on mediocre client work just to pay your rent next month. $100k means you can start thinking in 6-12 month increments, and can make decisions based on where you want to be next year. This allows you to take bigger bets, which lead to bigger payoffs.

• Second, your “scarcity mindset” starts to evaporate. Having 6-12 months of runway in liquid assets, as well as all the confidence you’ve acquired in order to get there, completely changes your headspace. As a result, your energy changes. You don’t come off as desperate for opportunities (like you were back at Level 1). Instead, you seem more self-assured. You know your worth. And, no surprise, more and more people want to work with you. You begin to “attract,” and no longer need to chase.

• Third, you now have money to reinvest in yourself. The other 6 Writer Career Paths that have to do with creating products all require some level of entrepreneurship and financial investment to execute well. Which is why it doesn’t make as much sense to pursue these when you have $0. You don’t want to launch digital products when you’re broke. You want to launch them when you can invest a few thousand dollars into the project to make it look high-grade and professional, and for that investment to not be “all your savings” and stress you out. (The same goes for Category Copywriting, which is the outlier. These deals are typically incentive-based, meaning high-risk and high-reward. You don’t want to take on these kinds of deals when you’re cash-poor.)

In addition, something interesting happens at the $20k per month and $100k net worth mark.

You start to question how much more you really need to be happy.

A phenomenon I’ve observed is that the vast majority of people think they need more money than they actually do. They think in order to travel, stay in lavish hotels & Airbnbs, eat at Michelin star restaurants, wear nice clothes, buy cool sneakers and watches, drive a sports car, and fly first class, that they need a hundred million dollars.

In reality, you can essentially do all of that when you’re making $20k per month pre-kids. (With kids, it’s probably closer to $30k-$40k per month without being stressed by any of these novelty purchases.)

The only thing that’s actually expensive, and still out of reach, is a nice house.

So again, don’t worry about solving problems you don’t have yet. Get to $20k per month, first. Then, let your machine run and stack cash until you’ve hit $100k in liquid assets. And once both of those things are “done,” and Level 3 is complete, watch how much your mindset starts to shift.

• Some people realize this is more than enough for them, and instead of “making more money” they’d rather focus on maximizing work-life balance and having more free time.

• And some people realize how much more potential they have and decide now they want to 10x their income from here.

Wherever you go next is up to you.

Level 4: $20,000/mo to $50,000/mo ($250k Net Worth)

Most people never get through Level 2, and even fewer get to the end of Level 3.

So if you’re here, congratulations. Making $400,000 or more per year means you’re in the top 2% of earners in the world.

Not bad for a writer!

Now, Level 4 is where things start to change—or I should say have the option to change:

• Option #1: You can keep scaling the service that got you here. For example, I scaled my ghostwriting agency well above $20k per month, eventually maxing out at ~$180,000 per month in revenue. So whenever writers tell me their service is capped, I have to remind them… it’s not. It just requires new and different skills to keep scaling—skills you haven’t built yet.

• Option #2: You can switch Career Paths and change to selling products. This is what I did after I shut down my ghostwriting agency. In 2021, I started a cohort-based writing program called Ship 30 for 30 with my co-founder, Dickie Bush. It was $800, each cohort would attract anywhere from 300 to almost 1,000 writers, and we scaled that business to $1M in revenue in the first 12 months—and $3M in revenue the year after.

Both scaling services or pivoting to products can work.

But the mistake is thinking you can do both.

If you want to pursue Option #1, that inherently means scaling yourself and the service you’ve been providing (like Ghostwriting) into an agency. It means hiring people. Training people. Building systems. It’s not that services aren’t scalable—it’s that they require very different skills in order to be scaled. So if you pursue Option #1, know those will be the skills you’ll be acquiring.

If you don’t want to build these skills, and instead want to pursue Option #2, you need to start deprioritizing the service you’ve been providing until you no longer offer it at all.

Again, this is what I did.

Back in 2020, my previous co-founder and I decided to scale back our ghostwriting agency, fire all our employees, and go back to just the two of us working with a much smaller number of clients who paid us a premium. And we did that for about a year so we could recover from burnout and figure out what each of us wanted to do next.

Then, at the beginning of 2021, I started Ship 30 for 30 with Dickie. And at the time, I was still ghostwriting (making ~$20k per month) because that’s how I was paying my bills and stacking my net worth. But as Ship 30 for 30 continued to grow, that inherently meant I had less and less time to ghostwrite, which inevitably made it harder to rationalize spending time ghostwriting (even if I was making great money doing it). Until eventually, by the end of the year, I had offloaded all my ghostwriting clients to someone else, stopped ghostwriting altogether, and had built Ship 30 for 30 into a 7-figure cohort-based writing program.

It was a slow transition that took an entire year.

The mistake, and what would have kept Ship 30 for 30 from scaling to $3M the next year, would have been thinking, “I bet I can keep ghostwriting on the side!” And trust me, at the time, turning-off a $250,000 per year income stream with the hopes of “making more” from a different Writer Career Path was scary. I debated it for months. But deep down, I knew it was the right decision.

Chase two chickens… and you catch neither!

The Exception: A Hybrid Agency

Now, there’s an exception to the “scale services or pivot to products” rule.

It’s called building a Hybrid Agency.

If you hit ~$20k/mo by providing a writing service and you decide to scale yourself into an agency, the next milestone I encourage writers to aim for is ~$60k/mo. At this level, your agency should look something like this:

• 12-15 clients

• $4k-$6k per client, per month

• 1-3 Writers

• 1 Account Manager

• 1 Virtual Assistant

When I was building my ghostwriting agency, this was the point when things were the best. My co-founder and I were completely out of the work. The business was profitable and healthy. And both of us were still making $15-20k per month but working 4 hours per day or less. We checked in on employees and continued to take the sales calls, and that was about it.

Which is why this is a great milestone on the mountain to pull over, set up camp, and start building digital products.

The reason you can “do both” at this stage is because you’ve once again solved for time. You’re out of the work. You’ve passed off fulfillment to other people. Creating digital products isn’t a “competing interest.” In fact, there are a handful of reasons creating digital products and building a Hybrid Agency actually makes your business stronger:

• Reason #1: Digital products are really just public-facing internal training documents. When you hire Writers to take over the writing, you’re going to have to train them, give them resources, and templatize as much of their role as possible. That’s a digital product. Or when you hire an Account Manager to talk to clients, manage projects and expectations, etc., you’re going to have to train them, give them resources, and templatize as much of their role as possible. That’s another digital product. So don’t think of “creating digital products” as some completely different thing. Just take your internal education, package it up, frame it appropriately for the target customer, and put it up for sale. This is what’s known as “selling your sawdust.”

• Reason #2: Digital products are 99% margin and require 0 fulfillment. If your agency is doing $60k/mo and your digital products start generating $10k per month, you just grew your business by 16%. Except you didn’t just grow top-line revenue by 16%, you grew profit by 16%. That goes straight into your pocket.

• Reason #3: Digital products make your agency more defensible, because they create a flywheel. 90% of the customers who buy your digital products buy them because they can’t afford your services. Great, you just monetized a whole new tranche of the market you weren’t serving before! But 10% of customers who buy can afford your services. And most of the time, when these customers buy a digital product, they educate themselves, realize “wow, this sure does take a lot of work,” and then just look to hire someone instead. And since you’re the one who just educated them, who do you think they reach out to first? You!

If you hit ~$60k/mo as an agency, then the next step is to get to ~$80-$120k+/mo with a Hybrid Agency.

Except remember… all that digital product revenue is 99% margin.

Which means you aren’t just growing your business.

You’re growing your personal take-home income.

Now, you might be thinking, “Cole… why didn’t you do this?” Because I hadn’t solved for time. When I was building my agency, I didn’t have time. We just kept scaling the service. And when I decided to scale my agency back down, I didn’t have time then either. My co-founder and I were back in the work—he talked to clients, and I did the ghostwriting.

If I could go back and do it again, I would have deliberately stopped growing our agency at ~$60k/mo and then started building digital products and moving to this Hybrid Agency model.

I just didn’t know enough at the time. I was young, inexperienced, and enamored with how quickly our business was growing.

Whoops.

Career Path Recommendations

Here are the Writer Career Paths that will get you from $20k per month to $50k per month the fastest:

1. Newsletter Writer

2. Ghostwriter

3. Sales Copywriter

4. Writerpreneur

You can get to Level 4 and above with both products and services, but there’s a nuance I want to point out: all of these career paths have to do with helping other people and/or their businesses generate more revenue.

• If you’re a Ghostwriter, you’re creating assets that help businesses educate customers and ultimately make more money.

• If you’re a Sales Copywriter, you’re writing things that turn prospects into paying customers, helping the business make more money.

• If you’re a Newsletter Writer, and you decide to start a paid newsletter, the fastest-growing and most-profitable newsletters are almost always anchored to helping a specific person, in a specific niche, build a skill to make more money.

• And if you’re a Writerpreneur, and you decide to start selling digital products, the most lucrative digital products are almost always anchored to helping a specific person, in a specific niche, build a skill to make more money.

I am axing Content Writer from this list, at this stage, because while you can build a Content Writing agency and scale to this level, Ghostwriting and Sales Copywriting tend to be far more lucrative. Content Writing is a great place to start as a beginner, but you will inevitably outgrow it and specialize in either Ghostwriting or Sales Copywriting.

Stack Net Worth To $250k

Level 2 ($10k/mo) is about growing.

Level 3 ($20k/mo) is about accelerating.

Level 4 ($50k/mo) is about scaling.

Once you get above $30k per month, this is where you start to really feel the gap between you and “everyone else.” You can live comfortably. You can save effortlessly. And in the range of $30k-$50k per month, there isn’t much on planet earth you “can’t do.” Even the most expensive hotels (unless you’re renting an entire penthouse floor, which is completely unnecessary) cap out around $2,000 per night, which you can now afford.

Now, here’s the problem.

At this level, you will feel extremely cash-flow rich. I remember when I hit this point, and there were some months where I would treat myself to every luxury I could possibly think of—wagyu steak dinners, $200 shots of tequila, first-class flights, you name it—and at the end of the month I’d still be able to save $10,000 or more. It was extremely jarring.

But being cash-flow rich and net worth rich are two completely different things.

When you’re cash-flow rich, you start to forget how hard it was to “make money” in the beginning. And without even meaning to, you take it for granted. You expect it. And because you expect it, you stop monitoring your spending because you assume your money-stream will just keep flowing next month. And sometimes it does. But sometimes, it doesn’t. And if you aren’t careful, your lifestyle can very quickly outpace the reality of your net worth—which puts you right back where you started, just with more zeroes coming in and more zeroes going out. Each month will feel like you’re living paycheck to paycheck, rich and broke at the same time.

Of all the levels, this is the one that requires the most emotional discipline.

The challenge is no longer figuring out how to make money as a writer. You did it. You figured it out. Now the challenge is protecting what you’ve built, letting your machine run, and building the foundation of your financial future.

Not Financial Advice

This is not financial advice, and I am by no means qualified to tell you what to do with your money. (I barely passed algebra in high school.)

That said, I have generated over $20,000,000 in revenue from my writing and writing-related businesses at the time of my writing this book. And I have personally made millions of dollars as a writer. So while I would encourage you to do your own research, and talk to your own financial advisor, I think it would be helpful to share a few mistakes and lessons I’ve learned along the way.

First, the impulse at Level 4 is to buy a house. Don’t. I know conventional wisdom says “buying a house is your path to financial freedom.” It’s not. Buying a house as a primary residence is not an asset, it’s a liability. And when you buy a house, you have to take all that liquid capital you just spent however-many-years accumulating and dump it into something that is illiquid, at risk of burning down, and won’t turn a profit unless held for 10+ years. If you want to make a lot of money as a writer, and build real wealth, the last thing you want to do is take all your available capital and lock it up in one of the slowest, least-profitable assets on earth.

Second, no big purchases over $10,000. Even with $250k in liquid assets, $10k is 4% of your net worth. That’s a meaningful chunk of cash! So just because you feel cash-flow rich, or because you now have 6 figures in liquid assets, don’t go and buy a $20,000 watch, or splurge on some fancy vacation. Sure, treat yourself to things within reason, but no singular purchase should exceed ~2% of your net worth.

Third, don’t underestimate the impact of just “stacking cash” month after month. This is the point when the math on your personal finances starts to play tricks on your mind. With $100k-$250k in liquid assets, the way you perceive $10,000 changes. Suddenly, an extra $10k doesn’t seem like “that much money.” Again, it’s only 4% of your net worth! And technically, you’re right. $10k relative to $250k isn’t “that much.” The problem is when this turns into a behavior you repeat month after month after month—and instead of saving $10k per month, you spend it. Well, a year later, that’s an extra $120,000 you didn’t add to your net worth, which is a ~50% increase in your total assets!

My biggest piece of advice at this level—and this is what I did, too—is when you enter the $30k-$50k/mo range, freeze your lifestyle.

• No big purchases

• No big changes in spending habits

• No big identity changes (“I’m a Rolex guy now!”)

However you’ve been living up to this point, stay there.

And stay there for at least a year.

If you can fight the urge to upgrade your lifestyle, this will be one of the most profitable years of your entire life—and will completely change the trajectory of your financial future. Because you’ll be “living” like you’re still earning ~$20k/mo, but you’ll be saving at 2-3x the rate.

A single year of discipline here is the equivalent of a decade or more of saving for the vast majority of people in the world.

Change nothing. Upgrade very little.

Just let your machine run, and your net worth stack.

Level 5: $50,000/mo to $100,000/mo ($500k Net Worth)

Welcome to the big leagues.

If you’re making $50k-$100k per month as a writer, you’ve made it.

This is rare air. Earning over $700,000 per year in America puts you in the top 1% of earners. This means, as a writer, you’re right up there with executives at publicly traded companies, software developers flush with stock options, hedge fund portfolio managers, and private equity managing directors. You should be proud, regardless of which Writer Career Path got you here.

Aside from buying a mansion and flying private, there’s almost nothing you can’t do at this financial level. Even some of the world’s most exclusive and highest-status experiences become available. In addition, if you’ve reached this level, chances are you’ve become friends with other powerful and wealthy people along the way—opening even more doors of opportunity.

Which is why the entire game changes at Level 5.

Stack Net Worth To $500k

There is a big difference between earning $50k/mo and $100k/mo.

At $50k/mo, most of life’s luxuries are “options,” but you still have to weigh doing them or not. You still notice the money being spent, and your net worth isn’t high enough where you can spend aggressively and “not care.” You also don’t have a (multi-million dollar) house yet, so you’re lifestyle-rich but haven’t fully graduated to the highest level.

But at $100k/mo, all of that changes. Post-tax, that’s ~$60k/mo. You can rent a baller house for $10k-$15k/mo (depending on where you live). You can drive a high-end sports car for ~$4k/mo, or a supercar for $5k-7k/mo. You can eat at the nicest restaurants, shop for new clothes, and fly first-class, all of which maybe adds up to another $10k/mo. Which means, even despite massively upgrading your life… you still have ~$30k/mo leftover!

This is where your financial position in life completely changes.

If your cash flow is high, and you feel secure in the vehicle that is producing $50k-$100k/mo in income, go ahead and upgrade your lifestyle, but the path forward is still the same: just keep doing what’s working, don’t overspend too much, and let your net worth stack.

Then, once you hit $500k in net worth, it’s time to do some hard reflection.

What Got You Here Won’t Get You “There”

The same way Level 2 ($20k/mo & $100k net worth) makes you question how much more you need to be happy, the same happens at Level 5—except it’s more extreme.

First of all, this amount of money coming in each month is absurd. When I hit this point, I spent a lot of therapy sessions processing through my newly established and privileged position in life.

Because there’s a funny thing about hitting $500k in liquid assets.

And the funny thing is… while you’re probably richer than all of your friends, and maybe even your parents (depending on how you grew up), you’re still a small fish in a big ocean relative to the truly wealthy people in the world.

Which is why $500k is where the game changes.

It’s very hard to cash-flow your way to millions of dollars in liquid assets.

For example:

• $100k/mo take-home income, so $60k/mo post-tax…

• $30k/mo in spending, so $30k saved…

• If you save $30k every month, it will still take you 66 months (or 5.5 years) to hit $2,000,000 in net worth…

• And it will take you ~10-15 years to get to $5,000,000 in net worth (depending on both spending habits and how you choose to invest the money you earn).

And $1M or $2M net worth might seem like a lot of money, but I promise, when you get there, it’s not. Even $5M isn’t a lot.

There’s an amazing quote from the show Succession where two of the main characters, Connor Roy and Tom Wambsgans, summarize this level perfectly:

“You can’t do anything with $5M. $5M is a nightmare. Can’t retire. Not worth it to work. Ah yes, $5M will drive you un poco loco my fine-feathered friend. Poorest rich person in America. The world’s tallest dwarf. The weakest strongman at the circus.”

You get the point.

If you’re not at this level yet, I can understand how what I’m telling you right now seems absolutely insane. So let me break it down:

If you have all $5,000,000 invested in a 5% treasury account (“passive, risk-free income”), that’s $250,000 per year pre-tax. Now, this might seem like a lot of money, but consider what this means:

• If you’ve reached Level 5, this is actually a massive down-grade from your current cash flow. So “shutting down your business” or primary revenue stream and retiring, unless you’re OK with the lifestyle downgrade that comes with it, isn’t really an option. At this point, you’ve gotten used to being cash-flow rich!

• But even if you don’t shut down your business, this extra “passive” income only marginally increases your monthly cash flow. Which means it will still take years, even decades, to get to higher levels of net worth.

So, you’re comfortable. But you’re also stuck.

There’s almost nothing in the $2M-$5M net worth range you couldn’t do in the $250k-$500k net worth range—because your cash flow is still the same. The only real difference is that once you have $1M-$2M in liquid assets, you can very comfortably buy a nice house without dumping 100% of your available capital into a horribly unprofitable asset.

This is what I did. I rented until I had $2M in liquid assets, and then I put $600k down and bought a really nice first house.

But $100k/mo and $500k+ in net worth is where you plateau. You essentially have everything you need to live an incredible life, and if you just stay the course you will continue to stack your net worth in a consistent and reliable way. That said, you won’t be able to fly private. You won’t be able to buy one of those sick $10M all-glass modern mansions in the Hollywood Hills, or a penthouse overlooking Manhattan.

And for 99% of people, this is more than enough.

But for 1% of people, this is the point where you really wake up to your own potential and decide you want more. Everyone’s motivations here are different, so I’ll just speak for myself: the reason I wanted “more from here” wasn’t out of greed, but curiosity. I’m obsessed with personal growth, and I always want to find out what else I’m capable of—and achieving new levels of income is an easy (and fun) way of measuring some of that growth.

When you plateau at $100k/mo and $500k-$2M in net worth, you realize you won’t actually “feel” any lifestyle changes unless you double your cash flow and/or 10x your net worth.

Which means the next level is $200k/mo+ and/or $10M in net worth.

And the only way to get “there” is to change the path you’re on.

Writer Career Paths To $10M

At $500k net worth, you basically have two choices:

• Decide the level you’ve hit is enough for you, and just keep on keeping on, let your net worth stack slowly, and solve for time again—optimizing for work-life balance, happiness, and joy.

• Or, decide the level you’ve hit isn’t enough for you, and start looking for a larger opportunity vehicle to hit higher levels, faster.

Now, I want to preface what I’m about to say: the vast majority of people (myself included) tend to believe whatever thing they’re currently doing “isn’t scalable,” but whatever thing someone else is doing, is. This is almost always wrong. Most businesses, in most niches, have the potential to become a $10M or even $100M business in terms of intellectual property or enterprise value. The question is whether you stick with it long enough, and successfully acquire the right skills in order to get it there.

So while some Writer Career Paths have the potential to generate different financial outcomes, your baseline default should be: “If I stick with this for 10+ years, and become one of the best in the world at it, I will make a fortune.”

Now, that said, some Writer Career Paths at this point start to make more sense than others.

For example…

• Ghostwriting or Sales Copywriting Agency Owner: If you’ve stuck with one of these all the way to Level 5, your next logical step is to “build to sell.” Instead of spending 10+ years cash-flowing your way to $2-5M in net worth, you can sell your agency and pull a lot of that time/cash forward. And since now you have all the skills to successfully monetize your talents, you can very easily start a new or related business after the sale to start generating cash again.

• Non-Fiction Writer: If you’ve been writing in an industry for 5-10 years, you now have a tremendous Information Advantage. Which means it’s time to write a book! This is actually how Ryan Holiday got started as an author. He first was a marketer, then built his own marketing agency, and then started writing non-fiction books and eventually became a full-time non-fiction author and speaker. Writing a book (or multiple books) in a niche power-levels your perceived value and unlocks all sorts of new money-making opportunities. (It’s also much easier to become a successful Non-Fiction Writer when you have a profitable cash-flowing business to fund your own marketing. Why do you think every book Tony Robbins publishes is a New York Times best-seller? Because he has a billion-dollar business to fund his book launches!)

• Writerpreneur: While you can unlock high levels of cash flow selling digital products as a writer, it’s very hard to turn these into sellable assets. The reason is because they usually become synonymous with the creator—introducing “key man risk.” In order to turn a digital product or education business into a sellable asset, you must remove yourself entirely from the marketing and ongoing management of the business. This is what Alex Hormozi did, and eventually sold his education business GymLaunch for $46M.

• Category Copywriter: If you can’t build equity in a business you own, the next-best alternative is to receive equity in someone else’s business you believe has upside potential. This is what makes Category Copywriting such a lucrative vehicle, and one that makes more sense to pursue later in your career. You can get paid in equity to help companies clarify their category messaging, and with the right company that equity has the potential to turn into millions of dollars. (These types of deals are very rare, but they happen.)

• Genre Fiction Writer: Lastly, if you have any aspirations of being a fiction writer, this is the point on the journey where this career path starts to make the most sense. Writing fiction isn’t a great path to pursue if you’re trying to “make money now.” But when you’ve already learned how to monetize your writing talents by providing a service, and you’ve already power-leveled your net worth to $250k-$500k, suddenly writing fiction has a lot less risk but a ton of upside. Remember, of all the Writer Career Paths, the top Genre Fiction Writers are actually the wealthiest of them all! (James Patterson, John Grisham, Stephen King, etc., they’re all worth hundreds of millions of dollars.) It’s what I like to call a Lottery Career Path, meaning the vast majority of the time you lose, but when you win… you win big.

This is where I am on the journey, right now.

My degree is in Fiction Writing. And when I graduated from college a little over a decade ago, my dream was to become a full-time author.

Unfortunately, maybe just like you, while I wanted to “do what I loved,” I also wanted to make money. My apartment was a piece of shit. So much so, I deliberately didn’t date very much in my early twenties because I was so ashamed of bringing a girl back to my apartment and them seeing my one-room shack. So, instead of starting out by writing fiction, I got a job in advertising, then moved into ghostwriting, then scaled my ghostwriting agency to millions of dollars in revenue, then started writing non-fiction books, then pivoted to digital products, then scaled those digital products to millions of dollars in revenue, until eventually reaching Level 5 and deciding… “what got me here won’t get me there.”

And if I want to achieve my goal, which is a net worth of $100M or more from my writing, then I need to keep picking bigger & bigger opportunity vehicles.

(If James Patterson can be worth close to a billion dollars, why can’t I make a measly hundred million?)

For me, that means building the largest digital writing education business on the planet, and on nights and weekends allowing myself to take bigger bets by starting to explore the Genre Fiction Career Path, and after that, the Literary Writer Career Path. And because of the financial position I’ve put myself in (mastering many of the other Writer Career Paths, first), I can now invest significant resources and take massive bets writing fiction without “risking it all” or feeling like I need to write the next Game of Thrones out the gate or I won’t be able to pay my mortgage.

These are the benefits of figuring out how to make money as a writer, first.

And why I would encourage you to consider moving through these Writer Career Paths in a similar order.

Outliers

Now, are there examples of writers who did the complete opposite of what I’m sharing with you here and found just as much, if not more, success?

Absolutely.

There are writers who graduate from Iowa’s Writer’s Workshop MFA program, land a book deal, publish a literary novel, and “overnight” skyrocket themselves to fame and fortune. I know this happens, and I’m not trying to pretend like it doesn’t.

What I’m trying to give you is the roadmap that leads to the highest likelihood of financial upside with the lowest amount of risk.

And while these outlier success stories exist, they are very far from the norm.

Whereas going from $0 to $10k/mo as a ghostwriter is completely doable, and hardly a “lottery outcome.”

The vast majority of the time, when a writer says to me, “It’s so hard to earn a living as a writer,” it’s because the career path they want to start with (“I want to write the song of my soul!”) isn’t the one that is most likely to give them the reward they seek (money now).

The irony of all this, of course, is that writing is a game of mental clarity. The best writers are the clearest thinkers. And yet, most writers don’t have the least bit of clarity when it comes to the trajectory of their careers, which moves on the chessboard lead to which outcomes, when, and why. They’re talented, but they’re writing in the dark.

I hope this roadmap gives you some candlelight.

Dear Writer,

So you want to be a Content Writer?

Over the past 20 years, the title of “Content Writer” has become a sort of umbrella term for all types of business-related writing: blog posts, SEO content, branded social content, website copy, newsletters, sales emails, even SMS campaigns, you name it. In many ways, the title of Content Writer is no different than the title of Freelance Writer, except for the fact that Freelance Writers typically work for themselves, whereas Content Writers are typically hired to do the same work for a company on a full-time basis.

Put simply, a Content Writer is someone who creates and manages written content for businesses and organizations.

Since many of these titles get used interchangeably (Content Writer, Freelance Writer, Copywriter, and Ghostwriter being the Big 4 most people refer to incorrectly), here’s how I differentiate between each of these different career paths—listed in order of perceived value:

Freelance Writer

This is the lowest perceived value title.

Freelance Writers typically operate in a mindset called “I’ll write anything, for anyone, in any industry, at any time.” As a result, they have zero pricing power and zero leverage. They have one client paying them to write short-form LinkedIn content for a dog food brand. They have another client paying them to write weekly newsletters about liposuction. And they have another client paying them to rewrite the website copy for their enterprise software solution.

Since most Freelance Writers charge per hour (or worse, per word), this creates a negative feedback loop cycle: to land clients and beat-out other Freelance Writers applying for the same gigs, they think they have to compete on price; since they compete on price, they earn less and less from each client; since they earn less, they need to say “Yes” to any and all new clients, every any industry, requesting any service; all of which crushes their ability to create efficiencies, let alone become known for a niche they can own, keeping them stuck in a churn-and-burn business model.

I discourage every writer I meet from calling themselves a Freelance Writer.

Content Writer

Content Writers are, in many ways, glorified Freelance Writers.

Instead of doing “anything” for “anyone” in “any industry” and working for yourself, Content Writers are typically hired by one company and then asked, as a full-time employee, to write “anything” for “any initiative” inside the company. This is more efficient (for the writer) than being a Freelancer—who is not only juggling different clients in different industries, but is also responsible for finding clients to begin with—but not by much.

But let’s clarify this even more:

There are two types of content all companies create (or should create):

• Brand Content: This is content designed for reach, with the goal of “reaching” as many qualified customers as possible—introducing them to you, your business, and most importantly, your position in the larger category.

• Marketing Content: This is content designed for people to take action, click on something, and put themselves in a position to buy (or sign-up, depending on the end-goal metric of the business). We can boil this action down to one word: sales.

The vast majority of people—from Freelance Writers to executives of publicly traded companies—think these two types of content are the same thing, and they’re not. Worse, they call it all “marketing” or all “content,” not realizing Brand and Marketing Content fulfill different goals, and require very different skill sets in order to be executed well. Which ultimately means hiring different types of writers.

As a Content Writer, most of the assets a business hires you to write fall on the Brand Content side.

Things like:

• Brand blog posts (including SEO and/or thought leadership)

• Brand website copy (Home page, About page, etc.)

• Brand daily/weekly/monthly newsletter

• Brand social accounts & content

• Etc.

Again, the goal of these assets usually leans more “reach” and educational, and is written from an all-encompassing Brand Voice.

Which is different than writing things that sell.

Copywriter

Copywriters are not Content Writers.

If Content Writers are responsible for Brand Content, then Copywriters are responsible for Marketing Content. But when I say “marketing,” I am using that word with nuance. Marketing Content is not about amplifying reach (that’s what Brand Content is for). Marketing Content is specifically designed to get a reader, listener, viewer, follower, website visitor, etc., to take action.

And this is a very, very different skill than writing educational Brand Content intended to increase the reach of your business’s digital footprint.

Copywriters are more valuable than Content Writers, who are more valuable than Freelance Writers. And the reason for the hierarchy should be clear, but let’s recap it one more time:

• Freelance Writers write “anything” for “anyone” in “any industry,” meaning they have zero pricing power and zero leverage.

• Content Writers write “anything” for “any initiative” inside one company, usually as a full-time hire—meaning they have some leverage and opportunity to build efficiencies for themselves, but incrementally so.

• Copywriters write “specific things” for “specific initiatives”—either working for themselves, or as a full-time hire—with the “specific goal” of getting potential customers to take action (sales). As a result, Copywriters are usually paid more than Content Writers, who are usually paid more than Freelance Writers.

It’s the specificity that creates the pricing power and leverage.

As a Copywriter, most of the assets a business hires you to write fall on the Marketing side. For industry veterans, this is usually clarified further and called Direct Response Marketing—meaning marketing that leads to some sort of directly measurable customer response:

• Emails (or email campaigns) that drive sales

• Promotion or product-specific landing pages that drive sales

• Social content CTAs or viral loop strategies that drive sales

• Digital ad copy (Google PPC, Facebook, Instagram, etc.)

• Analog ad copy (billboards, magazines, direct mail, etc.)

• VSL (video sales letter) scripting

• Etc.

It’s rare that a Copywriter will be hired to write things like company SEO blog posts or social content, just like how it’s rare that a Content Writer will be hired to script a VSL. And that’s because these two types of content—Brand (Education) and Marketing (Sales)—require very different skill sets, and as a result, require hiring two very different types of writers.

Ghostwriter

Ghostwriters are the top of the hierarchy.

For a couple reasons:

1. The term “Ghostwriter” has the highest perceived value. When you hear the term Freelance Writer, you probably imagine an unemployed twenty-something sitting at a coffee shop hacking away at another blog post nobody is going to read for minimum wage. When you hear the term Content Writer, you probably imagine the same sort of person, except they work for one company and have years of experience writing about one niche topic (liposuction, for example), making them slightly more valuable. And when you hear the term Copywriter, you probably imagine a shifty fellow who you wouldn’t necessarily trust to babysit your kids, but who is a ninja with words and can get people to buy via email. But when you hear the term “Ghostwriter,” what comes to mind? Someone who works behind the scenes? Someone who is selective, and an expert in their craft? Exactly. This is high perceived value.

2. The term “Ghostwriter” implies working with one individual. More specifically, it implies working with a very powerful, very successful individual. You don’t associate the term “Ghostwriter” with your local bike shop. You associate it with a celebrity who wants to write a book, or a CEO who wants to build their personal brand on the Internet. Again, high perceived value.

3. Ghostwriters work with industry leaders, who are the gatekeepers to all other opportunities. This is the real reason Ghostwriters are more highly valued than all other writing roles within companies—even if the work itself is the same. When you get hired as a Ghostwriter, you usually start out working directly with the founder, CEO, etc. And if you can earn their trust, who do you think they are going to ask first for additional help writing… anything? The Ghostwriter. It doesn’t matter if the business needs 800-word blog posts, or a 60-minute VSL script. If the founder/executive/leadership team enjoys working with a Ghostwriter, they are always going to give the next opportunity to that writer, first.

Which means calling yourself a Ghostwriter gives you the most pricing power, the most leverage, and the ability to unlock opportunities on both the Brand (Educational) Content side, as well as the Marketing (Sales) Content side.

Whereas Content Writers and Copywriters are typically siloed to one or the other.

The Art of Content Writing

Now, all of that said, Content Writers can still be extremely valuable to a company—and can be an amazing career path if monetized correctly.

For example, a 2024 CMI report found that 80% of survey respondents said creating brand awareness was their number one goal, with 72% of respondents wanting to build credibility and trust, and 68% saying educating audiences with their content is a top priority.

So let’s talk about the skills required in order to be a prolific Content Writer.

The Big 3 Content Writing Skills

There are 3 skills that separate the top 1% of Content Writers from the other 99%:

• Skill #1: An Information Advantage. This is true for every writing role in every industry, but is epitomized in content writing. It is very hard to write compelling educational content about a specific industry/category if you do not have some sort of Information Advantage in that industry/category. Translation: you must know more about this topic than most people. Industries like medicine or finance are good examples. If you are not familiar with the lingo of these industries, you’re going to create lukewarm, commodity content. Whereas if you’ve been in either of these industries for years (or decades), it almost doesn’t matter how well-written the content is… it’s going to be valuable because you’re communicating an Information Advantage! (This is also why Content Writers in one industry typically stay writing in that industry for a very long time—because their Information Advantage compounds.)

• Skill #2: Proficiency Creating “Actionable” Content. There are really only four types of content in the business/non-fiction world. In our writing program, Ship 30 for 30, we call this the 4A Framework. There’s Aspirational content (“I did, you can too”), Analytical content (“Here’s what I think, based on data”), Actionable content (“Here’s how to… step by step”), and Anthropological content (“Here’s the psychology behind why”). By a wide margin, the vast majority of content writing for businesses falls in the bucket of Actionable content—explaining “How To” do something to a reader. An extreme example would be a company like Apple, which has thousands of Content (or Technical) Writers on staff responsible for creating “How To” content for users. Remember when you didn’t know how to change the background of your iPhone and turned to Google for help? Somebody had to write that!

• Skill #3: Simplifying Difficult Concepts. The best Content Writers are not “verbosity machines.” In fact, one of their biggest value-adds is the ability to take complicated ideas or frameworks and break them apart into easy-to-follow steps. This is especially true for industries like technology, medicine, finance, or crypto where the founders or executives may possess a tremendous amount of industry knowledge (extreme Information Advantage!) but have a very hard time explaining it in Layman's terms. Which again reinforces the value of Brand (Educational) Content, and a Content Writer’s role within it: you can’t expand the reach of your brand to wider and wider audiences if everyday people don’t understand what you’re saying.

Unfortunately, most Content Writers do not possess any of the above skills—and instead measure their value by word count or hours worked.

Which is why most Content Writers don’t earn very much money.

According to Glassdoor, the estimated total pay for a Content Writer is $67,157 per year, with an average salary of $61,034 per year. And according to Indeed, the average Content Writer makes approximately $21-25 per hour.

Not bad, but nowhere near what you can earn as a Copywriter or Ghostwriter.

The Content Writer Career Path

Being hired as a Content Writer for a company, especially in an industry where you have a strong personal interest, can be an amazing way to “get paid to practice writing.”

Unfortunately, the pro of this career path—lots of jobs available, and more being created each day—is also the con. Lots of jobs equals lots of competition, which means fewer opportunities to move up in an organization. Most Content Writers stay Content Writers for a very long time (putting a ceiling on their earning potential). And the only ones who elevate from there inevitably move out of “the writing” into some sort of leadership role where they become responsible for managing and overseeing other writers (becoming more like Editors). And even if you get “here,” your earnings are still capped in a big way.

Just to show the discrepancy: according to Salary.com, as of 2025 the average annual salary for a Digital Content Writing Manager is $130,780. And as far as writing jobs go, this is pretty great. Until you compare this number to what someone like Evaldo Albuquerque made copywriting for Agora Financial. In his book, The 16-Word Sales Letter, he reveals his copy drove over $120 million in revenue for the company, of which he was compensated based on performance (translation: he probably made a few million dollars from his efforts).

Now, Evaldo is certainly an outlier. But it’s important to look at the outliers of each career path to get a sense of where the theoretical ceiling is—and then work backwards.

And the Content Writer career path ceiling is pretty low, relatively speaking.

Case Study: Steph Smith

So, how do you break through this ceiling?

How do you avoid the trap of being hired as a Content Writer, and then staying a Content Writer for 20 years hooked up to a drip where, at best, you receive a 1-3% raise each year?

In short: you have to build leverage—either within the company, or outside of your full-time job on your own.

Steph Smith is an amazing example.

By every definition, she had reached the top of the Content Writing world from a career path perspective:

• As a manager, she led a 30-person publications team and operated 6 technical blogs.

• And helped build the Hustle, one of the world's largest email newsletters, creating and scaling their premium publication, Trends, to thousands of subscribers and millions in ARR... in under two years, leading up to an 8-figure acquisition.

From here, had she not built any leverage, it’s reasonable to assume the rest of her career would have been “more of the same.” She probably would have bounced between companies every 2-5 years, each time getting a title promotion but incrementally increasing her salary. And she probably would have worked on other very cool, but similar projects: building the same sorts of teams, and deploying the same types of strategies over and over again.

Nothing wrong with this career path!

But how was she able to avoid this fate, leapfrog all of her peers, and end up being hired by one of the most well-known venture capital firms in the world (a16z) as their podcast host—now making a living as a full-time creator?

By building leverage.

Instead of continuing to climb the conventional ladder of the Content Writing career path, Steph took all of her knowledge about Content Writing and did the following:

• Started writing online, accumulating over 150,000 followers on X alone.

• Built her personal website to hundreds of thousands of page views, and her newsletter to 350,000 subscribers.

• And then compiled all of her content writing knowledge into a multimedia book, called Doing Content Right, which she shared has done over $250,000 in sales.

Pretty cool, right?

So, how do you build leverage—specifically as a Content Writer?

The 3 Ways To Build Leverage As A Content Writer

There are three types of leverage you can build in the Content Writing world:

The first is Operational Leverage. If there are only 24 hours per day (and really only 8-12 working hours per day), and only 7 days per week, then how does one writer “work more?” By themselves, they can’t. But if they can train other writers to write the same way they do, they can “produce more” through operational (or labor) leverage. This is where a writer becomes a department head/manager, who may one day even become a CMO and/or build a company of your own where you assemble & train content writing teams for other businesses.

The second is AI Leverage. Within the same constraints (hours per day, and days per week), another way of “producing more” is by using AI instead of other humans. For example, our paid newsletter Write With AI gives writers, creators, and business owners prompts to increase the efficiency and quality of their writing using AI. I believe the AI wave will fundamentally transform most Content Writers into Prompt Writers to give themselves, as well as the companies they work for, more leverage—but more on this later.

The third is Attention Leverage. This is where you step outside your role within a company and begin building yourself as a creator—like Steph Smith. Attention is leverage because the more people who look to you for expertise, the more opportunities you have to monetize that expertise and the more defensible you are. An audience is an asset.

Said differently, imagine a Content Writer who doesn’t have any of the above:

• No Operational Leverage—they can write well, but they are capped by hours in the day and days in the week.

• No AI Leverage—they can write well, but they can’t use technology to produce any more, any faster.

• No Attention Leverage—they can write well, but have no audience of their own, meaning they are beholden to the company they work for (or some new company) to give them opportunities to grow or earn more.

The vast majority of Content Writers in the world have zero leverage. They’re talented. They’re loyal. But they have very little control over their earning potential.

And to add insult to injury, these writers also think the way they break through this ceiling is by “becoming a better writer.”

And how well you can write has very little to do with it.

The Business of Content Writing

I started my career as a Content Writer.

When I graduated from Columbia College Chicago, my first (and only) job was at a small advertising agency in the city where I would write content for brands. At any given time, I was responsible for 5 to 8 different clients, and for writing everything from social content for a local restaurant’s Facebook page to blog posts about, yes, liposuction or hair removal.

I was a glorified Freelance Writer making slightly above minimum wage.

Well, after working at this agency for about a year and a half, I sat down with my boss and asked him for a raise. I made my case: how I worked hard, showed up early and often stayed late; how I had become responsible for some of our biggest accounts; how my skills had improved and I needed less and less oversight; all the things I thought led to making more money. I was in for a rude awakening. My boss said, very directly, “All of those things are true. But they don’t make the business more money. And I can’t rationalize paying you more for this role.”

I was 24 years old. And that was the moment where I realized everything I had been told about success in the world was wrong. It had very little to do with hard work, and much more to do with impact. And if I wanted to earn more money, he explained, I needed to find a way to make the business (our little agency) more money too.

One way of solving this problem would have been jumping ship and trying to find another agency or brand willing to pay me more for the same work—which I entertained. One day, during lunch, I walked down the street and interviewed at a bigger agency in a nicer building with sexier amenities (like cold brew on tap and Ping-Pong tables in the lobby). The interview went well, but it quickly became clear to me that a raise in the short-term didn’t solve my long-term problem. As a full-time Content Writer, I couldn’t see a path to achieving my goals and making more than $100,000 per year. And the only path where that seemed like an option meant becoming some sort of manager and no longer writing, which was the thing I really wanted to do.

Many writers find themselves at this same fork in the road, and many lack a framework to figure out where to go from here. I know I did.

So, I’d like to give you some options:

3 Ways To Elevate Out Of Content Writing

In my opinion, of all the career paths, Content Writing is a terrific place to start but a terrible place to end up.

The reason it’s a great place to start is because Content Writing jobs are low risk (if you write a mediocre blog post it’s not like the brand implodes). This is also what makes them low reward. Which means it’s a great way to get started as a beginner, get paid to practice, and start building up an Information Advantage in a given industry. But at some point (not after 3 weeks, more like 3 years), you’re going to need to move your skills into a different vehicle—otherwise your skills and earning potential are going to plateau.

So, here are some options.

1. Pivot into Ghostwriting.

This is what I did.

Not long after my raise request, my boss informed the office he was looking for some extra help writing emails and structuring proposals for clients. Unpaid. Everybody else kept their eyes on their laptops in front of them, hoping to disappear and not get chosen as tribute, whereas I willingly raised my hand. I didn’t yet know how to elevate out of being a Content Writer, but I figured more time with the guy who owned the business signing my paychecks was probably a good investment in my future.

That turned out to be one of the best decisions I ever made.

He didn’t give me a raise. Instead, he had me sit in his office with him and transcribe emails to potential clients, industry peers, and executives at other companies as he would orate. I was practicing the art of becoming a ghostwriter and I didn’t even know it—and I did this for 2 more years with him before eventually quitting and deciding to work for myself (where I went on to generate millions of dollars as a ghostwriter for founders & executives).

If you are currently working a full-time job as a Content Writer, chances are, you have the same opportunity I did. Go to your boss, or even your department head/manager, and ask if they’ve been thinking about writing online, sharing their insights at scale, or building their personal brand. The vast majority will say, “Actually, funny timing… this is something I’ve been thinking about for quite a while.” Offer to be their personal Ghostwriter for free, and start racking up hours of practice.

If you aren’t currently working a full-time job as a Content Writer, or for whatever reason your boss/manager says “No,” go find someone else in your network who needs a Ghostwriter. I promise you, opportunities are everywhere. And the easiest, lowest-pressure way to get started is to ghostwrite for one person, for free, until you feel competent in your skills.

Then, once you feel like you’ve got a handle on things, start selling your services.

You’ll earn way more as a Ghostwriter than you ever will as a Content Writer.

2. Build an Information Advantage and then become a Writerpreneur.

The second option is to capitalize on the long-term value of your Information Advantage.

One of the benefits of being a Content Writer in a specific industry is that you’re essentially getting paid to learn about that industry. You aren’t just “writing.” You’re learning, and then crystallizing those learnings into written content. Don’t underestimate the value of this value!

If you’ve been writing educational content for years in a specific industry—doesn’t matter which or how obscure it is; in fact, the more obscure and niche, the better!—a different way of monetizing your talents is to package your insights up into digital products. Let me give you a perfect example. If you are a Content Writer in the financial world, then you know something a lot of Content Writers who aren’t in the financial world don’t know: there are actually laws around what kind of financial advice you can give (in the form of content online). Think about the value of this knowledge.

A not-so-savvy Content Writer will spend their entire career continuing to write educational content for brands in the financial world, making incremental more money each year until eventually plateauing. And they will spend every year thereafter, seated on this plateau, believing that if they could just work a little harder, or become a little better of a writer, they will (one day) make more money. But it never happens.

A savvy Content Writer, on the other hand, can see the dead-end ahead of them. They can also see the value of their value. And this Content Writer might one day take all their insights about what financial planners can-and-can’t-say in their content online and package it up into a $350 text & video course called something like, oh, I don’t know…

“The Compliant Content Blueprint: A Definitive Guide for Financial Advisors on What You Can—and Can’t—Say Online.”

This is leverage.

But this kind of niche digital product can’t be created without an Information Advantage. So, you should see your years of working as a Content Writer in the financial world as the “investment” you had to make in yourself to acquire this knowledge—which you can (and should) monetize later.

3. Build an Information Advantage and then become a Newsletter Writer.

The next-best vehicle for monetizing the Information Advantage you acquire by being a Content Writer in a specific industry for a long period of time is to launch a paid newsletter on that same niche topic.

This is particularly true in journalism.

More and more each day, columnists at newspapers and magazines are realizing they are essentially glorified Content Writers. And if they don’t swap vehicles, they are going to stay stuck at wherever they’ve plateaued. (Similar to the Content Writing world, the only way to elevate to becoming a higher-paid journalist usually means becoming a manager—aka Editor-in-Chief).

So, what are they doing?

They’re leaving the magazine or newspaper (aka the brand) and starting paid newsletters of their own. Said differently, they are launching their own 1-person journalism publications.

And you can do the same in any industry or niche, and anywhere you have some sort of Information Advantage.

The Future Of Content Writing

Now, let’s pretend you don’t want to pivot out of Content Writing.

Well, let me tell you where I believe this entire industry is headed.

Two words: Prompt Writing.

In the early 2000s, when “content on the Internet” was first starting to become a thing, the vast majority of companies downplayed its impact. In fact, they couldn’t even wrap their heads around how their fax machine brand, or candy brand, or spa brand could even create content online. What were they going to do? Post pictures of their fax machines?

Today, in 2024, over 200 million small businesses are on Facebook alone.

Over the past 25 years, the rate at which companies and individuals have decided “we need to create content online” has gone parabolic. And every year that goes by, the curve on the chart gets steeper and steeper. Which means brand, educational content isn’t going away anytime soon.

In late 2022, when ChatGPT stepped on the scene, the overwhelming reaction was, “This is the end. AI is taking over. We’re all out of a job.” Writers especially. I can’t tell you how many times a day I see a comment on something I’ve written online from an aspiring writer who says, “What’s the point? AI is going to destroy our jobs anyways.”

This is where looking at history is important:

• When Photoshop launched in 1990 (can you believe that?), it didn’t destroy the job of the Designer. No, it turned designers digital, and lowered the barrier to entry to become a designer. Photoshop created exponentially more opportunities, and exponentially increased the amount of design in the world.

• When Instagram launched in 2010, it didn’t destroy the job of the Photographer. No, it turned photographers digital, and lowered the barrier to entry to become a photographer. Instagram created exponentially more opportunities, and exponentially increased the amount of photography in the world.

• And when ChatGPT launched in 2022, it didn’t destroy the job of the Writer. No, it turned writers digital, and lowered the barrier to entry to become a writer. And ChatGPT (and other AI writing platforms) will create exponentially more opportunities, and exponentially increase the amount of writing in the world.

So, are companies and individuals all of a sudden going to stop creating branded, educational content? No. Quite the opposite. More and more companies and individuals understand the value of creating content online every single day.

Which means, if more and more individuals and companies want to create content online, they are going to need more Content Writers (more jobs, not less!). And if “more content” is the goal, they are going to want those Content Writers to produce as much quality content as possible.

So, going back to the constraint we talked about earlier: if there are only 24 hours per day, and 7 days per week, how do Content Writers produce more quality content than they’re already producing?

By using AI Leverage.

The highest-paid Content Writers of the next two decades are going to follow the same path hand-drawing designers did when Photoshop was invented. They’re going to defer as many “manual” tasks as possible (all the low-leverage stuff) to technology, which will allow them to spend more time on higher-leverage and more creative tasks (like coming up with compelling ideas, or even better, creating new high-leverage prompts).

In our Write With AI newsletter, we call this the 10/80/10 Rule.

• You do the first 10% of the work of coming up with the prompt.

• ChatGPT does the middle 80% of the execution.

• You do the last 10% of edits to polish it off before publishing.

Now, does this scare you?

Is there a voice in your head right now, screaming, “Well I don’t want to learn how to write prompts! What happened to good o’l fashioned writing? Doesn’t anybody care about art anymore? What is wrong with our world?!”

If so, I get it. And there’s a deeper moral question here I’m sure Socrates would love to have a go at.

But it doesn’t matter.

The world is moving in this direction. It’s happening, whether you like it or not. And you can either build new skills, stay relevant, and make a ton of money being on the cutting-edge of innovation. Or, you can fight it, fail to adapt, and join the cohort of Content Writers protesting outside about how AI stole their jobs, all the while failing to realize AI didn’t steal their job. Their job just changed, and they didn’t want to change with it.

The choice is yours.

My Recommendation

If you are currently working as a Content Writer today, I would strongly recommend you start thinking about different ways to build leverage:

• Operational Leverage: This means you want to elevate into some sort of managerial role and train other writers to “write like you,” allowing you to produce more through labor.

• AI Leverage: This means you want to elevate your own personal efficiencies and train technology to “write like you,” allowing you to produce more through AI-labor.

• Attention Leverage: This means you want to monetize the value of your value by packaging up your insights (either writing-related or industry-related) into digital products or assets you can sell to a niche audience.

It honestly doesn’t matter which form of leverage you pick. All 3 have the potential to make millions of dollars.

But pick one and get going.

The only mistake you can make is failing to make a decision at all.

As a recap:

• Content Writers are essentially full-time, glorified Freelance Writers.

• Content Writing means creating brand (educational) content for a business.

• The 3 skills you want to focus on building as a Content Writer are: an Information Advantage, proficiency creating “actionable” content, and the ability to simplify difficult concepts.

• If you want to pivot out of Content Writing, your 3 best options are: bring your skills into the world of Ghostwriting (higher perceived value), monetize your Information Advantage by packaging & selling digital products, or monetize your Information Advantage by starting a paid newsletter on the same niche topic.

• If you don’t want to pivot out of Content Writing, but also don’t want to plateau, embrace AI. Spend as much time as possible learning how to write effective prompts. And then look for ways to use those prompts to either increase your own efficiencies (getting more done in less time), adding increased value to the company you work for (internal leverage), and/or monetizing “the value of your value” in a different way by selling those prompts to other Content Writers and/or businesses who employ Content Writers.

Dear Reader,

To kick-off 2025, I spent $5,000 (and my co-founder, Dickie, also spent $5,000) to attend a 2-day business workshop at the Acquisition.com headquarters in Vegas.

And if you’re wondering, “Vegas? Did you hit the casinos before the event?”

• Yes… I did gamble.

• Yes… I did lose all the cash I brought ($3,000) at the roulette table.

• Yes, it all started with a tequila espresso martini around noon, and it ended with several Classe Azul Reposados on-ice and me betting it all on red (it was black).

• And yes, before the trip, I had one of my friends connect me to a guy whose entire business is to book dinner reservations at impossible-to-get restaurants, who yes… successfully got me and my wife and her parents a table at Delilah. (If you know you know.)

That was the first two days.

The latter two days was spent main-lining business information from 8:30am to 6pm.

And if you’re also wondering, “But Cole… $5,000? Was it worth it?”

The answer is Yes. Very much so.

And you’ll understand why by the end of this post.

Acquisition.com Workshop Review

Some quick context:

• The workshop is 2 days long (from 8am to 6pm).

• The workshop costs $5,000 per head. (I went with Dickie so each of us paid $5k.)

• The room held approximately 100 people, give or take, with a mix of solo founders/business owners & co-founders (like us) going together.

• 60% of the workshop was listening to different topic-specific presentations by each of the subject matter experts on their team—who also run different divisions inside Acquisition.com, which manages a portfolio of businesses. (So for example, we heard from their Head of Recruiting, Head of Business Strategy, Head of Marketing, etc.)

• Each presentation was helpful in its own way, and the only thing that made one presentation “more helpful” than another would be the relevance of that topic to your specific business. (For example, the Hiring presentation we didn’t find as “helpful” because that isn’t our core problem right now. But I guarantee everyone else in the room who has “hiring” as their core problem found it very relevant/helpful.)

• 20% of the workshop was then sitting in small groups with these subject matter experts and getting to ask them questions. (This was probably the most valuable part of the workshop for us.)

• The other 20% of the workshop was then presentations and/or Q&As with Alex and Leila.

Some tangential "things-to-know”:

• The event is catered (breakfast & lunch).

• They did an amazing job having gluten/dairy-free options (usually “the” reason why I hate going to events, because most people don’t do this and, since I have food allergies, I basically don’t get to eat the entire day). I was extremely grateful for this, and also appreciated their attention to detail here.

• The team was all warm and welcoming. Nobody made you feel like you didn’t belong there, no matter how big or small your business was.

• The Acquisition.com headquarters isn’t far from the Vegas strip, so it’s convenient to get to from both the airport and whatever hotel you stay at.

And just, in general, I really appreciated their attention to detail.

The event was extremely well-run.

Who Is The Acquisition.com Workshop For?

There were some businesses in the room doing $250,000 per year in revenue, and others doing $12,000,000 in revenue.

In my opinion though, you will get the most out of this workshop if you are at-or-above $1,000,000 per year in revenue, regardless of what your business is, does, or who it serves. Reason being, so many of the things you need to hear, learn, or do below $1M/year in revenue are already in the free content & resources Alex and Leila share online.

Now, is there benefit hearing it again in-person? Sure.

But you’ll get more juice out of it if your business is at a lightly more mature place.

For context, last year our business did $6,000,000 in revenue, so we were almost exactly in the “middle” of the room as far as low & highs go.

And we walked away with way more than $5,000 worth of value (the price of the ticket).

Acquisition.com Workshop Upsell: Value Acceleration Method

Now, like any good info business, at the end of the workshop they pitch you on “more” help & access to their portfolio team.

Here was the offer:

• $45,000 (or $35,000 if you sign up before the event is over).

• You come back for 2 smaller workshops with their team later in the year (you can pick the dates that work best for you).

• Before you come back, their portfolio team does a massive audit of your business and then when you come to the workshop they basically tell you, “If we were to invest in your business and treat you like a portfolio company, here’s what we would tell you to go do.”

• You go execute. You see how much you grow/they see how well you can execute, and then you come back for the 2nd workshop and do it again. (At least, that’s my understanding.)

Well, we have never made an investment in ourselves we didn’t make ROI-positive.

So we walked up to one of the sales guys after the pitch and said, “Do us a favor and take our money.”

We got a ton of value out of the first workshop. But we’re flying back out to Vegas in a few months to be part of this smaller group and get their portfolio team’s take on what else can be improved in our business.

And I guarantee you it will yield more than $35,000 in revenue for us.

“Is The Acquisition.com Workshop A Scam?”

During this pitch process, I overheard two entrepreneurs in the corner talking about how they “don’t like to get pitched” and how “it’s probably a scam.”

Let’s unpack that.

• Are there scams in the world? Yes.

• But are most “scams” actually scams? No.

People who call something a “scam” are really just low-information buyers who lack the appropriate context or information to make an educated decision for themselves.

And do you want to know the root of that problem?

Usually it’s some sort of faulty belief… like thinking, “If someone charges me money, they must be out to get me.”

Not much you can do to help these people. Their entire life is anchored in a constant state of suffering, and they are hell-bent on finding proof that their point-of-view (“I’m right!”) is correct.

Sadface.

My Answer:

So, is the Acquisition.com Workshop a scam?

Or are Alex & Leila “scammers?”

No. They are two of the most impressive entrepreneurs I’ve ever met (and I’ve ghostwritten for hundreds upon hundreds of Silicon Valley founders, venture capitalists, C-level executives of publicly traded companies, billionaires, etc.). And the way they have built these workshops is nothing short of amazing.

I was taking notes the entire time—not just on the content, but their attention to detail and how they ran the event itself.

15 Takeaways To Scale Your Business

Now, with all of that out of the way, here are all the “nuggets” I wrote down (in no particular order) during the two productive days I had in Vegas.

(I’m going to exclude my takeaways from my two unproductive days in Vegas… like “Don’t bet on red when it’s obviously going to be black.”)

Takeaway #1: Take out as much cash as you need from your business to feel “secure” personally… so that you can take more risk inside your business.

This is something I ROYALLY fucked up building my first company—my ghostwriting agency back in 2017.

I grew that agency from $0/mo to $180,000/mo in revenue in about 18 months. The mistake I made though was never taking any money OUT of the business to make my personal life feel more secure. In fact, the entire time we scaled that business, I had $5,000 - $10,000 in my savings account and that was it. (Meanwhile, our monthly payroll of 20+ employees was north of $100,000.)

As your business grows, you will inherently need to reinvest profits back into the business to keep it growing (we’re at this stage again right now). But that’s high risk. Which means, before you take that risk, make sure you’ve had a few months (or years) taking money out of the business so that you feel more comfortable/financially secure in your personal life… SO THAT you feel good taking that risk inside your business.

Takeaway #2: Above $5M/year in revenue, you don’t bootstrap departments. You hire subject matter experts who build the department.

This might have been my biggest “golden nugget” from the event, and thinking about the ROI of this simple concept relative to the fact I paid $5,000 to “learn this” is hilarious. $5k to learn something, at the moment I needed to learn it, that will make us millions more dollars in the future. (Not a bad ROI!)

This was also one of those “what-got-you-here-won’t-get-you-there” lightbulb moments.

I am a bootstrapper. Always have been. Whenever I have an idea, the first thing I do is go tinker and figure out how to duct-tape together something myself. And before you hit $1M or $2M or even $3M in revenue, that makes sense. That’s usually what’s required.

But this past year, our business grew a lot. And so did our team. We went from 13 employees to 28.

And the mistake I have been making (for months) is thinking, “Geez… I barely have any available time to bootstrap our next department!”

And it wasn’t until we attended this workshop that I realized (aka: someone said to me) that’s not how it works from here. Above $5M/year in revenue, you don’t bootstrap departments anymore. You take your cash, you go find someone who has already built the department you want to build, and you go buy their subject matter expertise and empower them to build it.

Completely different way of thinking about & solving the problem.

Takeaway #3: Before you change anything in your business, test it.

Piggy-backing on the above…

Another “bootstrapper” habit is to move fast and break things.

And when you’re small, this is correct. Perfection is the enemy of progress, so just do something and get moving.

The problem is, as you grow, the riskiest thing you can do is change something inside your business. Even if you’re convinced it’ll improve it. Even if you think, “There’s no way this won’t be ROI-positive.” When you have something that’s working, ANY change = some percentage of risk.

So a big piece of advice they hammered home to us was: don’t make company-wide changes.

If you have an idea, or are trying to solve a problem, don’t roll out a solution to the entire business, or the entire product, or the entire sales funnel, etc.

Instead, find a way to test your theory inside a contained environment:

• Have 1 closer try a different pitch, first.

• Have 1 coach try a different method with a student, first.

• Send a different offer to 10% of your email list (instead of 100%).

• Etc.

Takeaway #4: When you change something, expect a 20% decline in the short term.

Piggy-backing on the above again… when you change something, there will always be a period (in the short term) where metrics go down.

This is usually because, especially in a more mature business, when you change one thing that one change ends up affecting 5 or 10 other things, which inherently “change” as a result of the original change you made.

…which causes short-term inefficiencies.

…or causes short-term declining profitability.

…or causes some other metric to go down.

This isn’t a problem. It’s just something to expect (so you don’t see a metric go down in the short term and freak out).

Takeaway #5: There’s a difference between “continuity” and “back-end upsell.”

This was a really interesting clarification for us, and just goes to show how there’s always more to learn. (We’ve been in the digital education space for 4+ years now, and I had never heard anyone articulate this to me, this way, before.)

• Continuity means a customer keeps paying for access to the thing you already sold them.

• Back-End Upsell means a customer pays you (one-time or on a recurring basis) for access to “more” of what they already bought from you.

So let me give you an example.

Our core business is our Premium Ghostwriting Academy. And our core offer is we help turn burned-out freelance writers into Premium Ghostwriters by putting them through a 12-week curriculum, with 1:1 coaching, as well as group calls with me. And it’s a one-time payment.

• A Continuity Offer would mean at the end of the 12 weeks, we say, “Great, you went through the program. Now, if you’d like continued access to the curriculum, that continued access costs $99/mo.” (Or whatever price point you decide.) It’s payment to keep access to the thing you already bought.

• A Back-End Upsell would mean selling more coaching, more accountability, and maybe even a new roadmap or curriculum to help them accomplish their next goal.

Hearing this delineation was extremely helpful as we think about the best ways to scale our Back-End Upsell Offer after people complete the PGA program.

Takeaway #6: "Strategy is how you choose to allocate your limited resources against unlimited options.”

This is something I’ve heard Alex Hormozi say probably 50 times at this point. But for some reason, hearing him say it in-person made it click for me in a different way.

The entire game of entrepreneurship is a game of who can make the best decisions. Because we all have the same 24 hours in the day.

And how you identify “the best decisions” is by thinking deeply about how to allocate the few resources you have (time, energy, attention, money) against the unlimited options in front of you.

And in the context of growing your business, the way to make this decision (according to Alex) is to ask:

• “How does this get me more customers?”

• “And/or how does this make our current customers worth more?”

Anything on your list that doesn’t accomplish one of the above is probably the wrong thing to focus on (right now).

Takeaway #7: More/Better/New

This is one of my favorite Hormozi frameworks.

The path to improving anything goes like this:

• More: Until volume is the constraint, do more.

• Better: Once volume is the constraint, focus on increasing the quality of your volume by doing better.

• New: Once quality volume is the constraint, and you can’t do any more, and you can’t do what you’re doing any better, consider doing something new or different.

I love the simplicity of this.

But here’s a different way of interpreting the above framework (which Alex also articulated in a nice and sticky way):

• Doing “More” is the least risky thing you can do. If something is already working, there’s almost no risk to doing more of that thing.

• Doing “Better” has some risk, but also has some incremental reward. “Better” fundamentally means “change,” and as I already noted above, change inherently injects risk. But, some risk, some reward. Which is why “Better” leads to improvement.

• Doing “New” has the most risk. You’re choosing to do something you haven’t done before with the hypothesis this thing will in some way be more powerful than whatever you were doing before. High risk, high reward.

So when trying to figure out what to do, I encourage you to not just use the More/Better/New framework, but also consider the different risk levels associated with each decision.

Takeaway #8: CEOs think more like investors and less like managers.

This was a brain-breaking moment for me.

(And it wasn’t even Alex or Leila who said it. It was their Head of Strategy during her presentation, which was badass.)

I’ve been a Founder/CEO-type for 8 years now. I started my first company in 2017, and we just started 2025. And for the past 8 years, I always felt like my responsibility was “manage” people. And while that’s true, I see now how that frame causes your thinking to get sent in the wrong direction.

The way great CEOs build companies is they don’t think of themselves as managers. And their job isn’t actually to manage people. Their job is to find subject matter experts, who can run departments, who they can trust, who can successfully manage people.

A great CEO is an orchestrator (or in this metaphor, an investor).

Something for me to work on.

Takeaway #9: How you achieve the goal is irrelevant.

Something we’ve been banging our heads against the wall trying to figure out these past few months has been paid ads to grow our business.

From September 2024 to January 2025 we probably spent north of $250,000 on paid ads for our business.

And we lit most of it on fire (didn’t do much).

Another sadface.

Then, at the workshop, we talked to Alex a bit after the end of the first day during cocktail hour, and we told him our metrics and how we have been trying to get more customers using this new method (paid ads), and he basically said, “Why? You’re already crushing it on organic. Do more of what’s working.”

Quarter-million-dollar mistake we made.

Whoopsie.

The takeaway here is… how you achieve the goal is irrelevant. We kept thinking we needed paid ads because “that’s what everyone does.” But if you can achieve the same goal (more new customers) doing whatever you’re already doing, more, and then better, just do that. How you get there doesn’t matter. All that matters is that you do.

Takeaway #10: Don’t underestimate the value of a “better” team member.

Another thing Alex said to us that really hit was:

“A $500,000 team member is VERY different than a $50,000 team member. Get comfortable spending more.”

And meeting his and Leila’s team, I could see it. I have no idea how much they pay their portfolio team/subject matter experts, but they’re all rockstars. And it completely reset the bar for me of the sort of talent you can bring into your business.

This is absolutely a faulty belief/skill deficiency I’ll need to let go of to grow to the next level.

I need to get comfortable with the idea that the next department head we hire might be 2x or 3x more than any person I’ve ever hired in the past.

Takeaway #11: “The theoretical max of a business is the sum of the knowledge on the team.”

Building on the above… I thought this was brilliant.

If you’re the founder, and you’re the “smartest” person on the team (aka: you tell other people what to do and how to do it), then the theoretical max of the business is literally your own knowledge.

• The business will grow to the extent of your own experience/pattern recognition.

• And the business will stay stuck at the level where your experience/pattern recognition runs out.

I thought that was a fascinating way of looking at a business.

The takeaway here is: if you want to expand the theoretical max of your business, buy more knowledge.

For example: when you hire someone, you aren’t just filling a role. In an idea world, what you’re really buying is that person’s entire life experience. All the problems they’ve already figured out how to solve that you don’t. All the shortcuts they’ve learned about that aren’t even on your radar.

You expand the capacity of the business by adding more people who know more than you do.

Takeaway #12: Show team members “the gap.”

This was a gem from Leila.

When a team member in one role wants to move up to a different role, and they aren’t ready or qualified, don’t just say “No.”

Instead, show them the gap.

How she does this is by taking the job responsibilities list of the different or elevated role and highlighting all the things in red this team member currently isn’t doing or doesn’t have experience doing—so they can “see” the gap.

• Here’s where you are right now.

• Here’s what you aren’t doing.

• Here’s what I would need you to do (or be able to do) in order to consider you for this role.

I really liked this exercise because it shows people, if you want more growth potential, here are the exact skills you need to build and demonstrate proficiency in.

Takeaway #13: Checklists are more valuable than SOPs.

All roads lead back to making-things-actionable.

Takeaway #14: “What do you see that I believe about the world that isn’t true?”

This is a question Alex asks other smart people, specifically his mentors.

Takeaway #15: Anything can be a $100M business.

There’s no such thing as too niche.

People just give up too early.