The Substack Relationship Ladder: How One Comment Can Turn a Stranger Into a Paid Subscriber
Let's climb the Relationship Ladder
Update! Thank you to LisaLee for joining the Backstage Pass Paid community as member #49! Please give Lisa a warm welcome and check out her profile!
The 50th member will receive a free month added to the end of their subscription, whether it is a monthly or Annual subscription. More details at the end of the post!
At the end of January, I added 5 Annual Paid subscribers in the final 3 days of the month.
All 5 were subscribers who I had been interacting with for months. My relationship with all of them started in the same way: I saw a Note they wrote, I left a comment. That one comment led to them following me and vice versa. At some point they subscribed, and then we spent months engaging and interacting with each other.
Building a relationship, building trust.
That entire relationship started with one sentence 1 typed in thirty seconds.
Most writers think comments are conversation. They aren’t. Comments are relationship entry points. And every relationship entry point is a potential paid subscriber.
The Relationship Ladder
Let’s break down each rung of the relationship ladder:
Rung 1: The Comment
Most comments on Substack are noise. “Great post!” “So true!” “Love this.” They’re invisible because they’re interchangeable. Anyone could have written them.
The comments that start real relationships are specific. They reference something particular in the post. They add a perspective the writer hadn’t considered. They ask a question that shows genuine curiosity.
The goal of the first comment isn’t to be noticed. It’s to be remembered. One specific sentence beats ten generic ones every time.
Tactical tip: Before you comment, ask yourself “could anyone else have written this?” If yes, rewrite it.
Great point by Neela 🌶️, if your comment doesn’t move the other person to respond, then the interaction ends with you. Be intentional when you comment, be thoughtful to tap into the life of what the author was trying to communicate.
Rung 2: The Reply Thread
When someone replies to your comment, most people say thank you and disappear. That’s where the relationship dies before it starts.
The reply thread is where the relationship either deepens or dissolves. If you reply again with something that extends the conversation, adds another layer, or asks a genuine follow up question, you’ve created a micro relationship. Two people who have now had a real exchange.
This is rare on Substack. Most interactions are one and done. The writers who understand that the second reply is where the relationship actually begins have a significant advantage.
Tactical tip: Always have a second reply ready. Not a filler response. Something that genuinely moves the conversation forward.
Rung 3: The Follow
Following someone after a meaningful exchange is a natural signal. It says “I found this interaction valuable enough to want more of it.”
But the follow works both ways. When you follow someone after a genuine exchange they almost always check your profile. They read your About page. They look at your recent posts. You’ve essentially earned a warm profile visit from someone who already has a positive impression of you.
This is why your profile and your recent posts need to be doing conversion work at all times. The follow is when a stranger becomes a prospect.
Tactical tip: After following someone you’ve had a real exchange with, leave a thoughtful comment on one of their recent posts within 24 hours. It signals that the follow was genuine not reflexive.
Rung 4: The Subscribe
Subscription is the moment a prospect becomes an audience member. It doesn’t happen because you asked for it. It happens because the relationship has built enough trust that they want more of you in their life consistently.
The writers who understand this stop chasing subscribers and start building relationships. The subscription becomes the natural next step rather than the goal they’re desperately pushing toward.
Here’s the counterintuitive truth: the harder you push for the subscribe the less likely it is to happen. But when you focus entirely on the quality of the relationship the subscription often takes care of itself.
Tactical tip: Never ask for a subscribe in a comment thread. Let the relationship do that work. Your job in the comment thread is purely to be genuinely valuable and present.
Rung 5: The Ongoing Engagement
This is the rung most writers skip entirely and it’s the most important one before Paid conversion.
Once someone subscribes the relationship doesn’t manage itself. You need to show up in their world the same way you’d want them to show up in yours. Read their posts. Comment on their Notes. Reply to their emails. Make them feel like a person not a subscriber number.
This is where your personal outreach system lives. The writers on your Tier 1 hot leads list are sitting on this rung right now. They’re engaged, they’re watching, they’re warm. They just haven’t felt personally invited yet.
Tactical tip: Once a week identify five recent subscribers who are also writers. Go read something they’ve published and leave a real comment. This single habit has more conversion power than any CTA you’ll ever write.
Rung 6: The Paid Conversion
By the time someone reaches this rung the conversion almost isn’t a decision anymore. It’s a confirmation of a relationship that already exists.
People don’t upgrade because your content is good. They upgrade because they feel connected to you, they believe in what you’re building, and they want to be part of it at a deeper level. All of that is built rung by rung in the ladder above.
Tactical tip: When you sense someone is close to upgrading, a simple personal DM acknowledging their engagement and letting them know what’s inside your paid tier can be the final nudge. Not a sales pitch. A genuine personal invitation.
If you want to get a better sense of the signals that a free subscriber gives before upgrading to Paid, check this post:
Rung 7: The Advocate
This is the rung nobody talks about and it’s where the real long term value lives.
Paid subscribers who feel genuinely connected to you become advocates. They restack you. They recommend you to their audiences. They become case studies in your content. They refer other paid subscribers. They are your most powerful growth engine and they got there because of one comment you left six months ago.
The Key Insight Section:
Every relationship on Substack starts with a comment. But not every comment starts a relationship. The difference is intention.
When you comment to be seen you create noise. When you comment to connect you create relationships. And relationships on Substack are the only thing that compound.
Your next paid subscriber is probably already in your comment threads right now. They’re watching how you show up. Whether you reply thoughtfully or disappear. Whether you engage with their work or only your own. Whether you’re building a community or just an audience.
The comment is the entry point. What you do after it determines everything.
Behind the Curtain: Tracy Friedlander
Behind the Curtain is where I profile Backstage Pass’ Paid subscribers. It really is a wonderful community and today I wanted to talk about my friend Tracy.
Tracy is very much like me in that she approaches Substack very strategically. She tracks what works for her, then adapts and pivots. It’s how her current positioning as The Second Act Strategist came about, which I absolutely love! And her personal branding with her Subi alter-ego is wonderful!
Currently, Tracy is really leaning into helping her subscribers up their Notes game, which is another example of how she tracks and pivots. She analyzed how she was using Notes, she tracked what worked, then doubled down. She saw great results, then started sharing her strategies with her subscribers. Brilliant!
And she’s growing like a weed in the South in the summer. I think she said she recently added 76 subscribers in a week? I haven’t added that many in a month yet! If you are wanting to up your Substack game, especially on the Notes side, definitely subscribe to Tracy!
My Bestseller Badge Experiment is Underway!
I announced this on Tuesday, but I am trying an experiment to speed up the process to help me get to 100 Paid subscribers, which would net me the first level Bestseller Badge. It’s wonderful social proof and is thought to bring a temporary boost to conversion rates as well as a slightly lower, but permanent boost. So it’s a big deal for multiple reasons.
To help speed up the process, I have temporarily lowered the price of the Annual tier from $100 to $75. The Annual tier will remain at $75 until I hit 100 Paid subscribers.
When I announced the experiment on Tuesday, I had 47 Paid subscribers.
Welcome to Lee Drozak, who became #48 on Tuesday!
Additionally, I have added in a few incentives:
When someone becomes my 50th Paid subscriber, that person will receive a free month added to the end of their subscription.
When someone becomes my 75th Paid subscriber, that person will receive 6 free months added to the end of their subscription.
When someone becomes my 100th Paid subscriber, that person will receive a FREE YEAR added to the end of their subscription.
Now I can already hear some of you thinking “Hey, couldn’t I just become a monthly to get the 50th/75th/100th Paid subscriber and get the free month/s?” Yep, you could certainly do that!
I will keep the progress updated here and via Notes as to where the count is so everyone can follow along to see how close I am to 100. And if you want to help me spread the word about this experiment, a Restack would be greatly appreciated!
BTW, if you are a current monthly subscriber and want to upgrade to Annual now to take advantage of the new price, if you do so I will add an additional 3 months to the end of your new Annual subscription.
So if you aren’t a current Paid subscriber, please consider taking advantage of the new $75 price for Annual. This is the first time I have ever lowered my prices, even temporarily.
This a really helpful breakdown of how to grow and build your subscriber base. I never use the 'follow' feature but am intrigued to do so now. Cheers Mack.
You are my go-to human for all things Substack, and I appreciate the work. I also understand that at times, my comments may be lacking of substantive quality. I appreciate the push to do better in order to create stronger, meaningful relationships.