Why $5 Subscriptions Are Killing Your Newsletter Income

"You're doing it wrong," my friend said, staring at my Substack stats. "Nobody's going to read all your best content for free."

He had a point. The traditional newsletter playbook says you should:

• Write killer free posts

• Put your best stuff behind a paywall

• Ask people to pay monthly

• Hope they stick around

But here's what I discovered after a year of testing: that advice is completely backwards.

Let me explain...

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The Hard Truth About Traditional Subscriptions

Want to build a thriving newsletter the traditional way? Here's what you need:

• Over 1,600 people paying monthly

• About 20,000 free subscribers to get there

• Months (or years) of growth

• A lot of patience

I don't know about you, but I'm not that patient.

I decided to flip this method on its head and the results have been surprising. I started offering digital products from Day 1, instead of waiting for enough content to charge for paid subscriptions.

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The Accidental Discovery

Earlier this year, I was burnt out. I had been creating two separate content streams:

• Free posts to attract subscribers

• Premium posts to justify the subscription

It felt like running on a treadmill. Double the work, half the results.

Then something interesting happened...

I decided to record a simple one-hour masterclass sharing my best strategies. I priced it at a single payment less than a few months of subscriptions.

My expectations were low. Maybe 6-7 sales if I got lucky.

First month results shocked me:

Week by week, sales grew. I ended up selling over 50+ on my first little push.

By month's end, I'd earned more than my previous six months of subscriptions combined.

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Why This Works Better

Think about it like this: Hiding your best content behind a paywall is like opening a restaurant where people can only smell the food from outside.

Sure, some will be tempted enough to pay... but most will just walk away hungry.

Instead, I started doing something different:

1. Give Away Your Best Stuff (Yes, Really)

• Deep-dive strategy posts

• Behind-the-scenes looks

• Real numbers and results

• Actual frameworks I use

2. Create Simple Solution Products

• Recorded masterclasses

• PDF templates and guides

• Implementation workbooks

• Resource collections

(I use Stan Store to sell my digital products. There’s also Gumroad which is entirely free to use).

3. Keep Prices Simple

Why? Because people don't need to think too hard about a single reasonable payment. Think $50 and under. Higher ticket products $100+ people usually have to think about it for a minute. $500+ it’s a big enough investment that takes more thought.

It’s the trust factor. It takes time to build trust with your audience to the point where they’re willing to spend money with you.

The $50 and under products are a quick, easy busy. Over deliver on your products in value, and you’ll have a subscriber (& customer) for life.

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The Real Numbers Story

My current approach:

• 2-3 free deep-dive posts weekly on Substack

• 2-3 Substack Notes per day

• 3-4 LinkedIn short newsletters per week

• CTA on Substack posts » Simple digital products

The result? I now make more in a month than I used to make in six months of subscriptions. All while growing from to 3,400+ free subscribers because I'm not hiding anything behind a paywall.

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What About Premium Access?

Should you never offer subscriptions? Not exactly.

When you do add a paid tier, make it truly premium:

• Private community access

• Monthly live workshops

• Implementation support

• More direct access to you

But here's the key: This comes AFTER you've built trust through free content and proven your value through entry-level products. The more people trust you, the more they’ll jump at the change to be in your paid “community.”

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The Simple Framework That Works

Every piece of content should:

1. Solve one specific problem

2. Provide immediate value

3. Naturally lead to your paid solution

It's like offering samples at a bakery. Give people a taste of your best work, and the ones who want more will happily pay for the whole cake.

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Start Growing Today

Want to start generating income from your newsletter immediately? Here's what to do:

1. Write 2-3 detailed "hero posts" that showcase your expertise

2. Add a natural next step for readers who want more (Call to Action CTA)

3. Make it feel like a helpful suggestion, not a sales pitch

Then, everywhere you post start linking to your “hero posts.” These “hero posts” will be quietly selling your digital products in the background.

Remember: Most writers stay poor because they don't know how to sell their work. Don't be afraid to offer solutions to people's problems.

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The Solution: Substack Growth Bootcamp

I’m excited to announce that I’ll be putting together a Substack Growth Bootcamp in January. It’s going to be a close-knit group of Substack writers who are ready to kick-off their growth in 2025 together.

I’ve learned that people grow within community. Sometimes we need that extra little push to help keep us accountable to our growth goals. Be on the lookout to sign up on the waitlist for January’s Bootcamp. Excited!

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Need Help Now? The Six-Figure Substack Growth Masterclass

If you need help TODAY, I get it. I have a solution for you: I’ve reopened doors to my Six-Figure Substack Growth Masterclass for this week only.

In the masterclass, I break down the exact strategy and roadmap I’ve used to grow from Zero to 3,400+ subscribers in less than 6 months. I also explain the monetization strategy I mentioned in this post that’s bringing in $3K to $5K+ per month (with daily sales).

If you’d like to get access to the masterclass before it’s taken down, just click the button below, and I’ll see you on the other side:

A personal note: This isn't about quick wins or growth hacks. It's about building a sustainable business that serves your audience while supporting your goals. The Substack Growth Model works because it puts value first. Everything else – growth, sales, impact – follows naturally.