Growing a profitable newsletter on Substack looks complicated.
Notes. Hooks. Posts. Livestreams. Automations.
ARRGH. MARKETING VOMIT.
Maybe you’ve started. Or maybe you’re stuck doing more research.
I used to complicate everything too.
But growing a newsletter is extremely simple.
A profitable newsletter has maybe five moving parts. That’s it. The rest is noise people invented to sound smart.
And the money math is friendlier than you think. You don’t need a stadium full of readers. Nor do you need a bestseller badge. 20 people paying you $500 is ten grand a month. Twen-freakin-ty.
I’ve been running newsletters for over 10 years. Let me show you the uncomplicated version that actually fits into your packed calendar.
One small thing to do before writing a single letter
Most people I see writing here are totally confusing.
Substack is becoming noisier by the day. And the only way to escape that noise is to make your ENTIRE content you post about one thing:
Helping a specific reader overcome a problem / achieve a burning desire.
What Substack really is
Here’s where a lot of people mess up.
Substack is not a newsletter platform. It’s social media with a blog sending feature.
Read this again.
So the right way to use Substack is to treat it like a tool to drive subscribers to your REAL newsletter that leaves in a real autoresponder like Kit or MailerLite.
What to post on Substack
Substack is essentially simple:
Post short notes
Post long-form posts
Interact with people
Now, as always, the evil is in the details.
How many times should you post? What to post? What to do next?
Here’s what I recommend:
Find 3-5 people creating content for the same audience
Reverse-engineer what gets a lot of engagement
Write your own long & short-form versions of it
Aim for 1-2 long-form posts a week. A note every day. And 10 interactions (likes, comments)
Readers → subscribers
This is the thing I like the most about Substack.
It allows people to subscribe directly to your newsletter.
Every post you publish will help you get in front of readers. They can choose to subscribe.
When someone subscribes on Substack, they’re on Substack. Not on your real autoresponder. So they never get your welcome sequence. They’re not in the place where you actually sell your own stuff.
You want them in both spots.
The problem? You can’t just connect Substack to your autoresponder with the push of a button.
You need to set up a small automation that does it for you on autopilot.
Some will hurl: THIS IS NOT ETHICAL OR AGAINST TERMS OF SERVICE!!!
I’m not a lawyer.
But whether Claude Opus nor I have found something in the Publisher Agreement that blocks us from syncing your Substack subscribers to an external autoresponder. The agreement treats you as the “data controller” and Substack as the “data processor.”
So Substack is just handling your subscribers’ data on your behalf. The data is yours. The agreement even spells out that you may “collect, use, store or otherwise process” personal information from Substack users.
That’s exactly what exporting to your own autoresponder is.
I’m not a lawyer. But that’s my (and Claude’s) understanding of it.
Next step
Now you’ve got people on your list.
Most folks stop right here.
They build the list, then go quiet. Big mistake. If you don’t send regular emails, then they mark you as spam or quietly bail.
Think of your newsletter like a restaurant. You need people walking in the door. And you need to feed them once they sit down. A packed room with bad food? They never come back. A great cook with an empty room? No money.
You need both. At the same time.
So email your list. At least 2 to 3 times a week.
I know. You’re busy. You’ve got a job, kids, and doing this on the side. But these don’t have to be 1,200-word essays. A 200-word email works fine.
A story.
A rant.
One idea tied to the problem you solve.
Why so often?
Because every email is one more touch. And trust gets built one touch at a time. The more they hear from you, the more they trust you.
The more they trust you, the simpler it becomes to buy.
Sell the right thing
Only a minority of your list will buy.
So if you’re out there selling a $0.99 ebook, you’re cooked. You’d need a giant list just to cover your rent. The math never works.
Price is the whole game. Same effort, same list, wildly different paycheck.
There are three things worth selling to a small list.
Courses. Record once, sell forever. Price each one $200 to $500. One course, one problem. 50 sales of a $200 course is ten grand. Courses are 85% of my income.
Coaching. Get paid to answer questions, 1-on-1 or in a group. 20 people at $500 a month is ten grand. Twenty people.
Done-for-you. You do the actual work for the client. $3,000 to $5,000 a month. Land three clients and you’re past your goal.
See what just happened?
You don’t need 20,000 subscribers. You need a real offer at a real price, and a handful of people who say yes.
A mentor of mine used to say great marketing can’t fix bad math. He was right.
Get the math right first.
How I actually sell
Pick one offer. Give it a deadline. Run it for 5-7 days.
Then email every single day. Each email teaches one small thing, then points to the offer at the end. So even if they don’t buy, they walk away with something useful.
Only the last email is a straight “this closes tonight” pitch.
About 50% of my sales come in the final 24 hours. Every single time. People wait. The deadline is what finally makes them move.
So don’t feel weird about the deadline.
Do this at least once a month.
How it looks in practice
You post content on Substack → People join your email list → You send interesting emails that also promote your offers.
This won’t make you rich by next Tuesday.
But if you enjoy and stick to it for the next 12-24 months it could quietly change your life.



The last-day thing is real and it took me awhile to stop fighting it.
Wrote 7-day promos for a high-ticket coaching client, silence all week, then every sale landing in the final 24 hours.
When I started, scared me to death, haha.
Thought I did something wrong...
Now I just plan for it.
One thing I learned: the last day needs more than one email.
I'd send at least two variations of "this is it, closes tonight."
Never the fake "gone forever" line, just the honest deadline.
The people who were going to buy were waiting for permission to stop stalling, and the deadline is what gives it.
Hi Matt! I truly think this is one of the most important articles I ever read! You answered all my questions (and then some) about earning a living as an online content creator. Hope this comment makes your day!