When Does It Make Sense to Turn on Paid Subscriptions on Substack?

The question everyone asks

Photo by Kit (formerly ConvertKit) on Unsplash

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I remember when I started writing on Medium in 2021.

The first month, I published 15 stories and earned $25 from the partner program.

I was mindblown.

It was the first time I got paid for typing words online.

And to be honest, my stories were awful.

Fast forward to today, Medium isn’t what it used to be.

Many writers have moved over to Substack, where the game is completely different.

Unlike Medium, Substack doesn’t pay you directly. There’s no partner program.

But if you play it right, Substack can help you build a more profitable and sustainable business.

So the big question is:

When should you start monetizing your newsletter?

Here’s the honest answer (and you might not like it)

It depends.

Let’s break it down.

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First, What Is Your Newsletter’s Business Model?

Before talking about timelines or paywalls, you need to be clear about the kind of newsletter you’re building.

There are three main paths:

1. Paid subscriptions (monthly/annual plans for premium content)

2. Selling your own offers (like coaching, courses, ebooks, or services)

3. Sponsorships (selling ad spots to brands and businesses)

Each path has a different strategy and timeline for monetization.

Let’s break them down.

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1. If You’re Focused on Paid Subscriptions...

Substack lets you add a paywall with just a click.

It’s tempting to turn it on right away, but that doesn’t mean people will pay.

If you want to charge for your newsletter, timing matters.

Here’s a good rule of thumb:

Wait until you’ve published at least 10 high-quality posts and built some momentum with free subscribers.

Why?

Because people need a reason to pay.

You need to earn their trust first.

Give them a taste of your best content for free.

Let them get hooked.

Let them see the value you bring.

Turning on the paywall too early when you have no audience will only turn people away.

It’s like charging admission to a restaurant before anyone knows if your food is any good.

A better idea is to ask your readers to pledge before turning on the paywall.

Pledges are a great way to measure interest.

If people are willing to pay before the content goes behind a paywall, it’s a good sign you’re ready to start monetizing.

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2. If You’re Focused on Selling Products or Services...

Not every newsletter needs a paywall.

Some creators use their newsletter to promote coaching, digital products, courses, templates, or other offers.

If this is your approach, you can (and should) start monetizing from day one.

As long as your content is helpful and relevant to your target audience, there’s no reason to wait.

For example, if you offer 1:1 coaching, your first few newsletters can include:

• A clear call to action

• A link to book a session

• Testimonials or case studies

• Stories that show your expertise

And if you're selling a digital product? Launch your newsletter with it.

Build your content strategy around it. Each newsletter can lead naturally to your offer.

Having a ready offer from the start also helps you stay focused.

You’ll know who you’re writing for and what kind of content to create to serve them.

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3. Finally, if your newsletter is built for sponsorships…

Monetizing via sponsorships is another viable path you can take for your newsletter.

This works best for creators who’ve built a large enough audience (think 10k+ subscribers)

If you build your newsletter intending to monetize with sponsorships, the best time to start monetizing is when you’ve got at least 1k subscribers.

Beehiiv, in my opinion, is a better platform for newsletters built with sponsorship as the main path to monetization.

The Beehiiv ad network makes it easy for newsletter creators to start earning from premium advertisers, even with a small audience.

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To Wrap Up

There’s no single "best time" to monetize a newsletter.

It depends on your goals, your audience, and how you plan to make money.

If you’re relying on paid subscriptions, earn trust first. Deliver value, build an audience, then ask for the sale.

If you’re selling products or services, prepare your offer early and start promoting from the beginning.

Finally, if you rely on paid sponsorships, your goal should be to get a few thousand subscribers first.

Whatever path you decide to take, don’t rush. Don’t wing it either.

Plan your path, serve your audience, and the money will follow.

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