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Five Signals That a Free Subscriber is Ready to Upgrade to Paid

The behavior changes that tell you a reader is ready to go Paid

Mack Collier's avatar
Mack Collier
Nov 13, 2025
∙ Paid

selective color photography of person holding orange gas smoke standing on snow
Photo by Hugo Jehanne on Unsplash

Over the last couple of months, I’ve become borderline obsessed with improving my conversion rate. The end goal is to hit 10%. I’m on my way, but there’s still a long way to go. I’m going to share what I am learning with everyone.

At first, I did some things on my end that improved my results. The first was nailing down my content to focus on solving 4 problems for Substack writers. That helped drive a few Paid subscribers.

But over time, I began to realize that a lot of the improvement would come down to simple relationship-building. As I started being more intentional in how I connected with individual readers, I started paying closer attention to their behavior.

I began to pick up on some clues that were signals that a free subscriber is interested in converting to Paid.

What I love about this, you aren’t selling to a potential buyer. You are listening to them. This is about recognizing the signals that an interested reader is giving you, then connecting with them and encouraging them to commit.

The last thing in the world I want to do is start DM pitching someone after they subscribe and beg them to upgrade. No one wants to do that, and we block people on sight in most cases if they do it to us.

But if I can recognize when someone is clearly communicating to me that they are interested in learning more, I want to meet them where they are.

Here’s the five signals that free subscribers will send you when they are interested in going Paid (The last one will make every James Bond fan proud!):

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