Most Substack Pricing Advice Is Wrong - Here’s How & When to Go Paid

The full Reality Check.

At Write • Build • Scale, we recently crossed 1,000 paid subscribers, and in this post, I’m sharing everything I wish I had known before using paid subscriptions on Substack.

Let me be upfront: most advice about this topic is completely wrong because it misses the fact that there are multiple approaches that make sense. The right path depends entirely on your situation, not some guru’s template.

The most common advice you’ll hear is “provide value first” or “wait until you have an audience.” Sounds reasonable, right?

But here’s what nobody mentions: I’ve seen writers with 50 subscribers making $500 a month. And I’ve seen writers with 5,000 subscribers making $0.

The difference isn’t audience size.

It’s understanding the three different monetization strategies on Substack and picking the one that matches your actual life situation and expectations.

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The Three Monetization Philosophies

“When should I turn on paid subscriptions?” is one of the most common questions in my inbox. And every expert gives you a different answer because they’re answering for their situation, not yours.

There are actually three completely different models that work:

Model 1: The Immediate Monetizer — Turn on paid from your very first post. This is the “donation jar” or “buy me a coffee” approach.

Model 2: The Strategic Launcher — Build initial momentum with 100 to 500 subscribers, then launch paid with fanfare and exclusive content.

Model 3: The Audience Builder — Focus purely on growth first, aiming for 1,000+ subscribers, then monetize once you have critical mass.

Each model has winners making six figures and each model has people who crashed and burned.

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The Hidden Variables Nobody Talks About

Here’s what actually determines your timeline:

Your financial runway. Can you write for free for 6 months? Or do you need income flowing immediately?

Your content type. Is it naturally exclusive (industry insights, proprietary frameworks) or broadly valuable (general advice, entertainment)?

Your time availability. Can you realistically create two content streams—free and paid—or would that stretch you too thin?

Your growth strategy. Does your content have viral potential, or are you building steadily within a niche?

Your audience’s expectation. Did they find you through free content, or were they already primed to pay?

Let me show you how each model actually works—and who it’s best for.

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Model 1: The Immediate Monetizer

This might shock some readers, but some of the most successful Substack writers turned on paid subscriptions before they had a single subscriber.

This sounds counterintuitive, but it works if you’re building your publication with this model in mind from day one.

This approach works if:

• You’re already known elsewhere—on Twitter, LinkedIn, YouTube, or another platform where people already trust your expertise.

• You’re writing ultra-niche content with specific industry insights that people can’t easily find elsewhere.

• You need accountability to stay consistent. (Nothing motivates like knowing people are paying for your work.)

• You’re treating it as a “tip jar” rather than primary income—at least in the beginning.

The Donation Psychology

Here’s the key insight: you’re not selling “exclusive content” yet. You’re selling support.

Your messaging should sound like this: “Everything I write is free. If you want to support this work, you can become a paid subscriber. Think of it as buying me a coffee each month.”

The beauty of this model is that you never really have to “launch” or market your paid tier. It’s just always there, quietly available.

The downside, of course, is that this isn’t necessarily the most lucrative monetization path. But it removes the pressure of a big launch—and it starts building paying supporters from day one.

If you choose this model, here’s your playbook:

Turn on paid subscriptions immediately at $5 to $8 per month.

Set clear expectations: “All content is free. Paid is optional support.”

Add a “founding member” tier at a higher rate—something like $150 per year—for superfans who want something extra.

Focus 100% of your energy on free content quality.

Mention the paid option maybe once per month, softly. No hard selling.

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Model 2: The Strategic Launcher

This is my favorite model for most writers, and it’s exactly what we did at Write Build Scale.

When we joined Substack in 2024, we didn’t turn on paid subscriptions right away. We spent time understanding the platform dynamics, building momentum, and engaging our early subscribers.

Then we launched our paid tier with a big promotional event.

In our case, it was a bootcamp with several live sessions that we hosted for our subscribers. This worked perfectly because only paid members could attend live or access the recordings afterward.

This approach helped us instantly gain our first 100 paid subscribers and receive the Bestseller badge.

The key requirement: You need at least a few hundred subscribers on your list, and they need to be genuinely engaged. You need enough people who might take you up on the offer to justify creating exclusive content regularly.

This means you’ll spend a couple of weeks—more realistically, a couple of months—building momentum, social proof, and trust before you launch.

The Strategic Launch Formula

Let me break down the timeline:

Week minus 4: The Soft Prep. Mention that you’re “thinking about” paid options. Ask your readers what they’d want from a paid tier. Build anticipation without making any hard commitments.

Week minus 2: The Value Bomb. Publish the best free content you’ve ever created. Show people what you’re truly capable of. Get them hooked on your insights right before you offer more.

Week minus 1: The Announcement. Say “Next week, I’m launching paid subscriptions.” Explain exactly what paid members will get. Create urgency with founding member pricing that expires.

Launch Week: The Full Court Press.

• Monday: Launch announcement with a special offer

• Tuesday: Share a case study or success story related to your content

• Wednesday: Give a behind-the-scenes look at what you’re building

• Thursday: Social proof—testimonials, early feedback, comments from excited readers

• Friday: Last chance reminder for the founding price

The Content Split Strategy

Here’s what most people get wrong about paid content: they think they need to create completely separate content streams.

Don’t do this.

Instead, try this approach: Give away the what and why for free, but put the specifics and action steps behind the paywall.

For example, at Write • Build • Scale, we might publish an entire article describing a growth strategy—and that goes out to all our subscribers. But at the bottom of the article, our paid subscribers get access to a link that sends them to a Google Drive document with the exact template, step-by-step AI prompts, or worksheets that help them implement what they just learned.

Free readers get value. Paid readers get transformation.

We call this strategy “Content Funnels” and you can learn more about it here.

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Model 3: The Audience Builder

Sometimes, the smartest move is to wait.

But not for the reasons you think.

This approach makes sense if:

• You’re creating viral, highly shareable content that spreads naturally.

• You’re building a media brand, not just a newsletter.

• You have other income streams already supporting you.

• You’re playing for massive scale—100,000+ subscribers.

The 1,000 Subscriber Launch

When you have 1,000+ subscribers, you can do something special that smaller publications can’t pull off.

The Survey Launch. You have enough data to actually ask what price people would pay and what content they want most. The responses will surprise you—and help you price correctly.

The Beta Group. Invite 50 people to join a paid beta at 50% off. Get their feedback, refine your offering, collect testimonials.

The Social Proof Launch. Use those beta testimonials for your public launch. Nothing sells like real results from real people.

The Tiered Release. Stagger access to create urgency. Maybe founding members get a discount, or early subscribers get bonus content.

When you launch with 1,000+ subscribers, it’s much easier to gather meaningful feedback—and gain more than just a handful of paid subscribers in your first promotion.

The Platform Play

Now let’s talk about what I personally think is the most important and underrated monetization strategy.

Some writers never charge on Substack itself.

Instead, they use Substack purely for audience building with free content—then sell courses for $200 to $2,000, offer coaching at $100 to $500 per hour, or create communities at $20 to $50 per month on other platforms.

Here’s a post where I share exactly what this can look like.

Even though we’ve hit 1,000 paid subscribers, we actually treat Substack as our discovery and growth channel—not our primary monetization method.

Yes, we make money through paid subscriptions. But more importantly, we reach thousands of new readers every single month who wouldn’t have found our work otherwise.

Our paid tier serves as a natural selection process. Our paid subscribers are our most loyal readers—and they’re also the people most likely to buy our higher-priced offers during a product launch.

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The Danger Zones

Before we move on, I need to talk about the dangerous traps that kill most paid newsletters, so you can avoid making these mistakes yourself.

The Paid Content Death Spiral

What you absolutely should not do is turn on paid subscriptions too early. This forces you to create paid content when it’s not really worth the effort for just a handful of subscribers.

Here’s what typically happens:

You turn on paid too early, with under 100 subscribers.

You get 5 paid subscribers. Great—but now what?

You feel obligated to create exclusive content for them.

You end up spending 50% of your time writing for 5 people.

Your free content quality drops because you’re spread too thin.

Your growth stalls because your free content isn’t as good anymore.

Your paid subscribers cancel because there’s no real community or momentum.

You burn out and quit.

I’ve watched this happen dozens of times. It’s painful to see.

There are a few ways to prevent this spiral:

The 20-Subscriber Rule. Don’t create exclusive paid content until you have at least 20 paid subscribers. Before that, treat paid as a “support” tier with no extra content obligations.

The 80/20 Content Split. Put 80% of your effort into free content, 20% into paid extras. Never flip this ratio.

I see a lot of creators make the mistake of thinking their paid content is more important than their free content once they have a paywall.

That’s backwards.

Your free content is still selling your paid content.

If readers don’t feel compelled to upgrade, it’s probably because they’re not in love with your free content yet.

The Pricing Trap

Everyone defaults to $5 per month because it “seems affordable.”

But look at this:

100 subscribers at $5/month = $500

50 subscribers at $10/month = $500

25 subscribers at $20/month = $500

Higher prices mean fewer people to serve, which means more time for quality, which means higher retention.

The sweet spot for most writers: $8 per month or $80 per year.

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The Decision Framework

Let’s figure out your strategy based on a few simple questions.

Question 1: What’s your financial situation?

• Need income immediately → Immediate Monetizer

• Can wait 3 to 6 months → Strategic Launcher

• Can wait 12+ months → Audience Builder

Question 2: What’s your content style?

• Personal stories or general insights → Audience Builder

• Specific tutorials or frameworks → Strategic Launcher

• Industry insider information → Immediate Monetizer

Question 3: What’s your growth trajectory?

• Viral potential, highly shareable → Audience Builder

• Steady niche growth → Strategic Launcher

• Small but dedicated audience → Immediate Monetizer

Question 4: What’s your time availability?

• Full-time creator → Any model works

• Part-time (10+ hours/week) → Strategic Launcher

• Side hustle (5 hours/week) → Immediate Monetizer or Audience Builder

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The Hybrid Approach

Remember how I said most advice on this topic doesn’t make sense? That’s because it doesn’t take your circumstances into consideration.

Even though I’ve mapped out three approaches here, the truth is that you can mix and match.

Build your own hybrid that makes sense for you personally.

Maybe you start with the Immediate Monetizer model (tip jar only), then shift to a Strategic Launch once you hit 500 subscribers. Or maybe you build as an Audience Builder, then use the Platform Play to sell courses instead of ever turning on paid subscriptions.

There’s no single right answer. There’s only the answer that fits your life, your goals, and your content.

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The Real Permission You Came Here For

If you clicked on this article, I have a suspicion about what you actually came for.

It’s not the technical advice.

It’s permission to charge for your work.

Consider this your permission slip:

Your knowledge has value. Your time has value. Your insights have value.

Whether you charge from day one or day 365 doesn’t matter. What matters is that you eventually charge something.

After everything I’ve shared, you need to answer one question:

“Am I building a hobby or a business?”

Hobby means stay free forever, write when inspired, no pressure.

Business means pick a monetization model and execute.

Both are valid. But be honest about which one you’re choosing.

I’ve shown you three models. I’ve given you the numbers. I’ve shared the frameworks.

But here’s the reality: The best time to start charging was yesterday. The second-best time is today.

We’re crossed 1,000 paid subscribers because we started imperfectly. We tested. We adjusted. We kept going.

The writers making $10,000 per month on Substack aren’t smarter than you. They just started charging before they felt ready.

The question isn’t “When should I charge?”

The question is “When will I finally believe I’m worth it?”

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Your Next Steps

If you’re serious about building your Substack publication, grab our free Substack Starter Kit. It includes templates, frameworks, and checklists to help you launch and grow—whether you choose the Immediate, Strategic, or Builder path.

And if you want to learn how to actually grow your audience before you start monetizing, check out our guide on how to use Substack Notes to grow your publication.

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What’s your choice? Comment below and tell me which of these models makes the most sense for you personally! 💬