I was a few months into my Substack and feeling like a bit low.
My newsletter was growing steadily. I had maybe 500 subscribers. Every "how to monetize your newsletter" article I read said the same thing: turn on paid subscriptions, put your best content behind a paywall, and wait for people to convert.
So, I did exactly that.
I created a paid tier. I started holding back my best insights for paying subscribers only. I added that little "upgrade to paid" button to every post.
After two weeks, I had exactly three paid subscribers.
Three.
At $5 each, I was making $15 monthly. Meanwhile, my growth had completely stalled because I was no longer sharing my best ideas with everyone.
I felt stuck. Either keep my content free and make no money, or gate my content and kill my growth.
Then I discovered there was a third option that nobody talks about.
Let me explain...
The Hard Truth About Traditional Subscriptions
Want to build a thriving newsletter the traditional way? Here's what you need:
Over 1,000 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.
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.
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.
The Mindset Shift That Changes Everything
Here's the mindset shift that took me from struggling to thriving:
Stop thinking like a traditional writer. Start thinking like a problem solver.
Traditional writers keep their best content behind paywalls because scarcity creates value. But newsletters aren't magazines. Your readers aren't subscribers—they're real people with real problems.
When I started viewing my newsletter as a way to genuinely help people instead of just "building an audience," everything changed. I stopped asking "how can I get people to pay me?" and started asking "how can I solve their biggest problems?"
That shift led to better content, more engaged readers, and ironically, more revenue than I ever made trying to extract monthly payments.
The Biggest Mistake I See Substack Writers Make
Want to know the fastest way to limit your newsletter growth?
Start with paid subscriptions instead of digital products.
I see new writers with 200 subscribers trying to launch paid tiers. They think it shows they're "serious" about their newsletter.
Here's what actually happens: You immediately start gating your best content behind a paywall, which kills your growth potential.
The math is rough. Even if you convert 5% of your audience (which is optimistic), that's 10 paid subscribers. At $5/month, you're making $50.
Meanwhile, you could create one digital product that solves a real problem and generate $500+ in a weekend from the same audience size—while keeping all your content free to attract even more readers.
Here's the better approach: Monetize from Day 1 with digital products.
Keep your content free to build relationships and trust. Then offer something extra that's paid. A guide. A template. A framework. Something that takes your free insights and packages them into immediate action.
This way, you're growing your audience AND generating revenue without limiting who can access your best ideas.
What About Premium Access?
Should you never offer subscriptions? Maybe, but maybe not.
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.”
The Simple Framework That Works
Every piece of content should:
Solve one specific problem
Provide immediate value
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.
Start Growing Today
Want to start generating income from your newsletter immediately? Here's what to do:
Write 2-3 detailed "hero posts" that showcase your expertise
Add a natural next step for readers who want more (Call to Action CTA)
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.
What to Do When You Hit Your First $1,000 Month
Here's what nobody tells you about that first big month:
Don't immediately quit your day job. Don't assume it'll happen again next month. Don't get cocky.
Instead, do this:
Analyze what worked. Which product drove the most sales? What content led people to buy? What problem did you solve that people were willing to pay for?
Double down on what's working. If your Substack growth guide sold well, create an advanced version. If people loved your templates, make more templates.
Start building your next product. The best time to create your second product is right after your first one succeeds. You'll have momentum, confidence, and a clearer understanding of what your audience wants.
That first $1,000 month isn't the finish line—it's proof that this approach works. Now you can scale it.
Your First Digital Product in 48 Hours
Want something you can create this weekend? Here's the fastest path to your first sale:
Pick one question you get asked repeatedly. Check your DMs, comments, and email replies. What keeps coming up?
Write a 5-page guide answering it completely. No fluff. Just the exact steps someone needs to solve this problem.
Price it at $27. Low enough for an easy yes, high enough to filter for serious buyers.
Add a simple CTA to your next post. Something like: "I put together a quick guide on this if you want the step-by-step process."
That's it. Create once, sell repeatedly. You'll be shocked how many people will pay for a clear, actionable solution to a problem they're facing right now.
Ready to Diversify Beyond Paid Subscriptions? Join the Digital Product Masterclass
Look, I spent months figuring out how to create digital products that people actually want to buy. The trial and error. The failed launches. The products that sat there collecting digital dust.
But once I cracked the code on what works, everything changed. Now I consistently generate $5K+ monthly from digital products while keeping all my best content free.
If you're tired of depending solely on paid subscriptions, if you want to create products that actually sell, I've put everything I've learned into my Six-Figure Digital Product Masterclass.
This isn't theory from someone who's never built a product business. This is the exact system I use to create products that generate consistent revenue while growing my audience faster than ever.
Inside the masterclass, you'll discover:
✅ Never worry about subscription churn again: Build multiple revenue streams that don't depend on monthly renewals or keeping people locked behind paywalls
✅ Create products people actually buy: Follow my proven framework for identifying what your audience desperately wants and will pay for immediately
✅ Make more money per customer: Turn one-time buyers into repeat customers with a product suite that naturally leads to higher-value purchases
✅ Stop limiting your growth: Keep your best content free to attract more subscribers while monetizing through strategic product offerings
✅ Work less, earn more: Create once and sell repeatedly instead of constantly producing premium content to justify monthly fees
If you’re ready to create your first (or next) digital product, join 100’s of writers inside the class:
Question: If you could solve one problem for your readers right now and charge $47 for the solution, what would it be? Share in the comments and let’s help you brainstorm:
Great advice. My 12 subscribers will definitely appreciate my masterclass.))
This morning, I took the plunge and purchased the Masterclass, and then spent the next hour devouring the material while thinking “This is just what I needed, not just for my Substack, but for my business in general!”
The content is so neatly chopped into edible pieces that make it simple and clear, even for someone like me whose eyes normally glaze over and brain shuts off, when presented with information that includes anything remotely technical. (Sigh)
I thoroughly recommend this Masterclass and its Masterful Presenter.
Thank you so much Wes.