How to write your first 10 newsletters on Substack
Email is probably one of the most misunderstood marketing channels—ever!
And the irony is people think that newsletters are so saturated, “I shouldn’t have a newsletter.” But the vast majority of people can’t even write a coherent newsletter. So the competition is not that there’s a gazillion newsletters. It’s that there aren’t very many really specific and valuable and good newsletters.
I’ve been writing on the internet for 15 years.
Every year people tell me newsletters and email are dead. And every year some stat comes out and says that email is up and subscriber rates are up and newsletters are up.
So any faulty beliefs around email doesn’t work, email doesn’t work for my niche, email doesn’t work for my industry, email doesn’t work for my customers, my customers don’t read the emails — it’s all wrong.
None of those things are true.
How To Write Your First 10 Newsletters
This is a free taster of a live masterclass I (Cole) gave to our AI Writing Skool members.
Every Monday I sit down for 60 minutes and jam on a topic you suggest via our Typeform submission system. We cover everything from writing, to monetization, to AI.
This week when you enroll in Substack Starter Sprint, you also get a free 30-day trial to AIWS (which also includes access to AI-Cole, our custom AI model trained on our programs, curriculums, live sessions, books, and content).
The reason a lot of people don’t start newsletters is that they go, “Well, I don’t really know what I should write about.
So I want to share a framework that has been really helpful for me over the years. It does not matter what niche you’re in, what industry you’re in, what you’re writing about. I promise this works.
But before we get into it, a few quick rules:
Nothing is a marriage decision. You can’t mess it up. You will always iterate. This is not permanent.
Sequence doesn’t matter. The order in which you write about topics is irrelevant. On the internet, people do not read linearly. The reader is not buying into the sequence and the order. The reader is buying into the niche.
Don’t obsess over perfection. The moment you publish, you will notice things that can be improved. That’s how it works. The goal is not to make your first newsletter perfect. The goal is to make it good enough and then publish it so you can learn and iterate.
Think of your newsletter like an engine.
Start writing, let people subscribe, build the engine over time.
The 10 Magical Ways Framework
I have this really great framework I come back to often. It’s called the 10 Magical Ways to Expand Any Piece of Writing.
Here are the 10 ways:
Tips
Stats
Steps
Lessons
Benefits
Reasons
Mistakes
Examples
Questions
Personal Stories
Your first 10 newsletters should be all 10 of these.
Tips—newsletter number one. Stats —newsletter number two. Steps—newsletter number three. And so on and so on.
As a nice little rule for each one, you pick an arbitrary number that is somewhere in the ballpark of 3 to 7:
3 to 7 tips
3 to 7 stats
3 to 7 steps
3 to 7 lessons
3 to 7 benefits
3 to 7 reasons
3 to 7 mistakes
3 to 7 examples
3 to 7 questions
3 to 7 personal stories
Each one of these is a newsletter.
These are all things that readers care about. A reader wants to know what mistakes to avoid. A reader wants examples so they build some pattern recognition. A reader wants steps that they can follow. A reader wants to know the lessons you learned going through the thing that they’re about to go through.
For example:
Let’s do bookkeeping:
Tips: Bookkeeping tips for small businesses to save an extra $2,500 in 2026 in bookkeeping expenses
Stats: Three stats that show why bookkeeping is one of the best expenses a small business can incur
Steps: Five steps to get your books in order for your accountant come tax season
Lessons: Three lessons I learned hiring a bad bookkeeper
Benefits: Six benefits to being disciplined with bookkeeping all year long
Reasons: Seven reasons why you shouldn’t hire a big company to do your bookkeeping and what you should do instead
Mistakes: Six mistakes small business owners make come tax season that cost them $10,000 or more
Examples: Three examples of bookkeeping clients crushing it for their clients in 2026
Questions: Four questions you should ask before hiring a new bookkeeper
Personal Stories: Three times my bookkeeper let me down and how much it cost me in lost profit
One topic, 10 magical ways, very simple.
How to Make Each Newsletter Valuable
The beauty of the 10 magical ways framework is that it allows you to expand anything in a very reliable way.
A question I’m always asking myself is: what is the one thing I need to give the reader in order for them to feel like they got value?
A newsletter’s value is directly proportional to two things:
How many of the 10 magical ways can we cram in there?
How specific and/or unique are each one of the examples?
Let’s use the idea: Four questions you should ask before hiring a new bookkeeper.
We can already outline the newsletter:
Intro
Question #1
Question #2
Question #3
Question #4
80% of the value of the newsletter is not all the writing in between these.
The majority of the value is the 10 magical way thing that you picked in the subject line and how it gets mirrored in the subheads.
Why?
Because the reader wants the thing you promised. You’re promising four questions you should ask before hiring a new bookkeeper. The reader opens this—they want the four questions. It doesn’t matter what else you give them. The thing that they are opening the email for is they want the four questions.
You deliver on this promise by making your magical way the subheads.
You can immediately assess the quality of a newsletter by only looking at the subheads.
Bad Example:
Four questions you should ask before hiring a new bookkeeper:
Are you any good?
Have you been doing this for a while?
Do you love your job?
Are you in it to win it?
These are not good questions. They’re not specific at all. They’re very subjective. And they’re probably things that you’ve heard a gazillion times.
The quality of the questions dictates the value of the newsletter. Saying the value is the writing means you misunderstand the trade that’s happening. The thing that you are solving for is the specificity and the uniqueness of the thing that you’re promising.
Better Example:
Have you worked with any other companies in our same industry or niche? And are you familiar with our accounting standards?
Have you ever had a client deal with a lawsuit before? And how did you handle it?
That’s a lot more specific.
That’s a much better question than “are you in it to win it?”
This is where your time should be spent—figuring out what are the best questions, the best tips, the best examples.
Expand Your Outline By Stacking The 10 Magical Ways Inside Each Section
Once you have the subject line, the subheads, and the specificity dialed in—80% of your newsletter is done.
But how do we fill it in?
The way we fill it in is we go back to our 10 magical ways. We can actually use these inside of each section.
For example:
Question #1: Have you worked with any other companies in our same industry or niche? And are you familiar with our accounting standards?
Here’s why this is such an important question to ask:
Most industries have industry-specific laws and you want to make sure your bookkeeper speaks the language of your specific industry.
Most bookkeepers are generalists, and being a generalist is fine, but you will have much more success hiring a specialist if you can.
Lastly, you want to be aware of whether or not this bookkeeper is working with anyone you would consider a competitor, and it’s up to you if you’re okay with that or not.
Now the mistake that businesses make is they don’t ask these questions and then end up hiring someone who is:
Less familiar with their industry
More focused on just getting the job done versus truly consulting for you
And as a result, has less of an impact on the financial performance of your business
We have the main one which is the question, then we have reasons why, then we have the mistake.
We got three of the 10 magical ways into one tiny section. That is why when you read something like this, you go, “Wow, that was really valuable.”
They’re like Lego blocks.
All you’re doing is stacking them.
And the more of them you stack, the more valuable each section.
That’s it!
Chat soon,
—Dickie & Cole
Co-Founders of Ship 30 For 30
Co-Founders of Premium Ghostwriting Academy
Co-Founders of Typeshare
Co-Founders of Write With AI
PS - We put together a free 2,600 word mega-prompt to help you outline your newsletter.
