If you’re thinking about running a newsletter you likely have a number of questions. Those questions probably range from how often should you publish, what should you write about and what tech to use to publish your newsletter (I use Substack). If you’re reading this though, you’re on the Creators Getting Paid newsletter. So even though I spend a lot of time thinking about the questions I’ve already listed, the other questions I reflect on are: How do I monetize this thing and what in the heck goes behind the paywall if I decide to do that?
Today, I thought I would share some thoughts and strategies to help YOU get started on making money with your newsletter.
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Free Mini Workshop
Click the button below to watch the “How to Grow A Substack” workshop
Listen to the Podcast
How to Decide If You Should Add a Paywall to Your Substack
I share some thoughts around how to make the decision to actually paywall content in your online brand. Points made in this podcast are different from what is shared in this newsletter.
Previous Posts and Case Studies
Are you new to Creators Getting Paid, or a long-time subscriber and hate missing posts? I’ve linked to some of my favorite posts and case studies below.
How to Become a Paid Speaker (Steven M. Hughes-Case Study)
(Substack) Paywalls in 2025
I’m going to be candid and say that if you’re needing to earn a significant amount of money quickly-paywalling your content will disappoint you. It is a long-term approach to building a financially healthy brand.
In fact, you’ll see a number of Substack creators tell people not to paywall their content because the math isn’t mathing. They are both right and wrong. I also find it strange that they’re positioning their brands in this way considering they are on a platform designed for them to monetize via a paywall.
However, they are right in saying that most creators are thinking WAY TOO NARROWLY around how they can monetize their Substack. I’ve mentioned this numerous times in Creators Getting Paid as well. I’ve also said that my free subscribers paid significantly more for products and services in 2023. The first year of Creators Getting Paid. Why was that? They were people who had gotten to know me elsewhere and followed me to the Creators Getting Paid Newsletter.
Why Would You Paywall Your Content?
There are a lot of people who are really loud and wrong about this topic. They even may be making a steady income, but they missing some important points around paywalling content.
Have you heard about TRIP WIRES?! A paywall can act as a trip wire moving people towards purchasing higher ticketed products. A trip wire is an inexpensive offer that is so enticing that people opt into it.
Create curated and unique opportunities for your community members to get to know you better. To laugh about funny jokes, to give direct feedback about their project and to share your expertise.
A paywall provides a safe space that your audience can opt into in an increasingly unsafe world online.
Some of the people who want to support you have the money but are supporting several projects, so paying annually or monthly as a quiet way to cheer you on is a way they show their support.
Some of the people who want to support you don’t have a lot of money right now, and would like to support you in the way that they can right now. Remember circumstances change. I was one of those people.
Your First 5 Initial Steps
Now that you’ve said “Yes” to paywalling your Substack here are the next 5 steps to work through in no particular order.
Work Through the Fear-Don’t be afraid to paywall your content. Do you journal or have some other practice that calms your mind? Use that to help you work through the fear.
Why Are You Paywalling Your Content-Take time to work through the arguments for and against paywalling your work-Don’t share this with other people unless they’re in a mastermind. You’re working through these arguments because they also align with your fears and may be the things that come up when people voice frustration around paywalled content.
Paywall from day #1-Why? It takes time to learn how to curate great content behind the paywall. And, you’re setting an intention and making it clear to yourself and your audience that you’ve monetized your work.
Reflect on your money tropes-It often surprises me how deep-rooted money tropes and mindsets negatively impact my business.
5 Most Commonly Asked Questions
How Much Free Content Before the Paywall?
Deciding What Price for the Paywall
What Content to Put Behind the Paywall
What is the FUNCTION of a Paywall
What Content Should Not Be Behind the Paywall
Bonus Question
How to Deliver The Content Behind the Paywall
Want the Answers to the 5 Most Commonly Asked Questions?
I’m shamelessly putting those answers behind the paywall. See what I did?!