3 Drivers That Create Paid Momentum For Your Substack

Why some publications turn readers into paying subscribers—and others never make the leap.

This article is a collaboration between Jessica Drapluk of Unstuck to Published and David Roy from ENG Sales, bringing together two perspectives on growth, momentum, and paid subscriber conversion.

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Most creators think the gap between free and paid subscribers is solved by growth.

• More subscribers.

• More traffic.

• More visibility.

However, I’ve seen creators get their first paid subscriber with fewer than 100 readers.

And I’ve seen creators with hundreds or even thousands of subscribers struggle to convert anyone.

The difference is rarely audience size.

It’s clarity.

When readers understand exactly what your publication is, who it’s for, and what changes when they upgrade, paid momentum becomes much easier to create.

Most people focus on getting more people into the room.

Very few stop to ask whether the room makes sense once people arrive.

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David’s thoughts:

That’s not a growth problem. That’s a momentum problem.

Growth and momentum aren’t the same thing.

→ Growth is a metric.

→ Momentum is what happens when your readers start showing up for you (replying, sharing, upgrading) because they feel like you’re writing directly to them.

This article is about the gap between the two and the three drivers that close it.

David Roy writes ENG Sales, a newsletter that helps technical founders build revenue systems from the ground up.

He’ll show you what getting the momentum foundation right looks like.

Then, I’ll connect it to the engagement system that turns readers into paid subscribers.

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Getting Your Publication Live & Paid

One of the biggest mistakes I see new Substack creators make is waiting too long to think about monetization.

They tell themselves:

“I’ll figure out paid later.”

• First they’ll grow.

• Then they’ll publish consistently.

• Then they’ll build an audience.

• And eventually, they’ll turn on paid subscriptions.

The problem is that approach often creates a publication with readers, but no clear path forward.

I’ve started thinking about this differently.

Instead of asking:

“How do I get my first 1,000 subscribers?”

I think creators should ask:

“What would make subscriber #1 pay?”

That question changes everything.

Why? Because now you’re forced to think about:

• The outcome your publication delivers. ←

• The offer behind it. ←

• The difference between free and paid. ←

• Why someone would upgrade in the first place. ←

A paid subscriber isn’t just revenue.

It’s proof.

• Proof that someone understands what you’re building. ←

• Proof that your offer makes sense. ←

• Proof that your publication points somewhere. ←

The creators who build paid momentum fastest are often the ones who establish that foundation early.

Not because they’re trying to maximize revenue immediately, but because clarity compounds.

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The Broadcast Trap

Most Substack creators are publishing. Very few are connecting.

The default mode looks like this: write the post, hit publish, share it to Notes, check the open rate, repeat.

It feels productive. It isn’t compounding.

David did this for nearly a year with ENG Sales.

• Broadcasting to his list like he was sending a company memo.

• Writing for the feed, not for a person.

• The posts were solid (at least some were 😂).

• The replies were almost zero.

• Readers were opening, but nobody was talking back.

Then he made one change.

David stopped writing for everyone and started writing for one person.

For him, that’s the technical founder who defaulted into the head of sales.

Someone who’s growing a product they believe in, but hates the idea of “selling.”

David started writing like he was sitting across from that person at a coffee shop. He just wanted them to understand that selling is really just, “Problem solving with another human.”

The shift was gradual.

• Readers who used to open and scroll started replying.

• Then they started reaching out between issues, asking me for help.

That only happens when someone feels like you wrote it specifically for them.

Broadcasting optimizes for impressions. Connection creates momentum.

Broadcasting is one-way.

There’s no conversation started and without conversation, you have an audience—but not momentum.

That’s when I realized there were 3 drivers that helped me start more conversations.

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The 3 Drivers That Create Paid Momentum

Momentum isn’t accidental.

It’s the result of three things happening consistently in your content.

Each one adds force to the relationship between you and your reader.

Skip one and the system leaks.

Driver 1 — Problem Insight

Every article should open with your reader’s problem.

The difference is subtle, but it changes everything.

→ Leading with content says “here’s what I made.”

→ Leading with problem insight says “here’s what you’re dealing with and I’ve been there too.”

That second framing is what makes a reader feel found.

Readers who feel found build trust and trust is why they buy.

Before you write your next issue, ask yourself one question:

“What is my reader struggling with right now, this week, in their specific situation?”

Start there and build the content around the answer.

For example:

“How to Start a Substack in 2026.”

→ That’s content-first.

Compare that to:

“You’ve spent three weeks thinking about starting a Substack, changed your niche twice, opened 17 tabs about monetization, and still haven’t published a single post.”

→ That’s the problem insight.

The second version immediately helps the reader feel seen.

They recognize themselves in the problem before you ever give them the solution.

And when readers feel understood, they’re far more likely to keep reading, subscribe, reply, and eventually buy.

Driver 2 — Personal Story

Data convinces. Story connects.

Your readers can find frameworks and tactics anywhere.

What they can’t find anywhere else is your specific experience: the moment something clicked, the mistake that cost you, or the thing you tried that nobody told you would work.

One specific moment does more work than three polished insights.

It helps the lesson land.

→ It gives the reader permission to share their own moment in reply.

→ And it reminds them why they subscribed to you and not the hundred other newsletters covering the same topic.

The story doesn’t need to be dramatic. It needs to be real.

The more specific the detail, the more universal the resonance.

Driver 3 — The Direct Ask

This is the driver most creators skip. It’s also the one that closes the loop.

Every issue ends with one question.

Not “let me know what you think.”

A specific, low-friction question that invites the reader to locate themselves in the problem.

→ “What’s the one thing you’re still stuck on right now?”

One invitation. No pressure. Just welcoming conversation.

What comes back is more valuable than any open rate metric.

When a reader tells you what they’re stuck on, they’re handing you your next piece of content, your next offer, and the exact language your paid tier should use to convert them.

The direct ask is how broadcasting becomes conversation.

And conversation is where paid momentum starts.

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This is the same work David does with technical founders on the sales side.

• Driver 1 is defining the problem you solve, clearly enough that a buyer recognizes themselves in it immediately.

• Driver 2 is proving you’ve lived it, not just studied it.

  • Said another way, “what outcomes will you deliver and what outcomes have you delivered for others.”

• Driver 3 is creating the conversation that moves them from interested to committed.

The mechanics are identical whether you’re converting a B2B buyer or a Substack reader.

You’re solving a problem for a human. The platform changes. The pattern doesn’t.

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Jess’ Thoughts:

One thing I’ve learned building on Substack is that paid momentum doesn’t start when someone upgrades.

It starts long before that.

It starts when a reader feels understood.

• When the publication feels clear.

• When the offer feels relevant.

• When the creator consistently shows up.

By the time someone clicks “upgrade,” they’re usually not making a spontaneous decision.

They’re responding to weeks or months of trust being built.

That’s why momentum matters so much.

Growth gets people in the door.

Momentum gives them a reason to stay.

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Action Step

Don’t wait for your next publish date.

This week, open your Substack subscriber list and find your five most engaged readers—the ones who’ve replied before, clicked consistently, or stuck around the longest.

Send each one a direct message with one question:

“What’s the thing you’re still stuck on with your Substack right now?”

Five messages. ←

Five conversations started. ←

That’s how momentum begins—not with a campaign. With a question.

Thank you so much for being here. I truly appreciate you.

— Jessica

Move first. Refine second. Publish with structure.

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About Jess, The Creator

Jess helps creators stop overthinking and start publishing on Substack with clarity, structure, and a clear path to monetization.

Through Unstuck to Published, she teaches creators how to build a publication people understand, subscribe to, and pay for.

If you’re stuck between having an idea and launching a publication, that’s exactly what she helps people solve.

Explore Unstuck to Published →

About David at ENG Sales

David helps technical founders build revenue systems that create predictable growth without feeling like traditional sales.

Through ENG Sales, he breaks down customer conversations, sales systems, and revenue generation for founders who’d rather build products than sell them.

When you subscribe, you’ll receive his Revenue Flywheel Scorecard to help identify the biggest gaps in your current revenue process.

Explore ENG Sales →

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