Two Simple Ideas For Frontloading Your Paid Subscription Strategy

Let your most popular posts do the heavy lifting for you.

Jul 12, 2025

SUMMERTIME repost: Since summer engagement is pretty slow, I thought I’d repurpose a valuable tip that I published last year at this same time. This one provides insight into the age-old conundrum of when to go paid.

Even though I’ve never branded myself as a Substack “strategist” in any way, shape, or form, inevitably, people ask my opinion on paid strategies.

Since they keep asking I’ll share a method that’s been working moderately well for me. I run three Substack publications and I use this front-loading strategy for my two big ones.

Frontloading strategy #1:

I always open a publication with paid subscriptions turned on. I firmly believe in a creator’s right to prosper and believe it or not, people will pay for NOTHING, as I recently learned with my little pub called Dog Snobs.

As soon as I announced it, I got TWO annual subscriptions paid up front. With ZERO content on the page. I firmly believe that some people just want to support their favorite people.

Frontloading strategy #2:

Keep all your posts free for a good while and see which ones become superstars. After about a month, go through your post stats and see which one generated the following:

A) The most FREE subscriptions.

B) The most comments and likes.

To quickly figure out these stats, you can sort your posts in descending order under Settings » Stats » Emails » and then click on the heading you wish to sort by.

Then, change the ones with the highest numbers into paywalled posts.

The idea here is that if/when anyone stumbles onto those posts they’ll see lots of engagement. New readers get hit with a dose of FOMO, which might inspire them to make irrational decisions and upgrade their subscriptions 😁

I mean, if I saw this many comments and likes, I’d want to know WTH is inside, wouldn’t you?

Screenshot from the backend of the Substack you’re reading now

Likewise, if you realize that 294 people subscribed through one particular post, try paywalling it and see how many upgrades you can get in the future. In the screenshot below, those posts were free for months, allowing them to rack up the numbers. Now, I’ve switched them over to paid. Obviously, they’ve earned it.

I like to call those big number-generating posts my “Hall of Famers.” They’ve earned their way there and can now rightfully assume their position.

Disclaimer:

I will say it one more time: I’m NOT a Substack coach or engagement strategist, so I don’t guarantee results with any of my advice. But I do look at my numbers and experiment quite a bit because, why not?