How to Get Your First Paid Subscribers When Everything You've Tried Has Failed

I love the smell of Stripe notifications in the morning...

You've been writing for months. You've followed every "expert" tip on growing your Substack. You've crafted thoughtful posts, engaged with other creators, and watched your free subscriber count slowly climb.

But your paid subscribers? Still stuck at 1 (Love ya, mom!)

Meanwhile, you're watching Notes from other creators celebrating "another amazing month" with hundreds of new paid subscribers, and you're thinking: "What the hell am I doing wrong?"

Here's the truth: You're not doing anything wrong. You're just missing three critical psychological elements that make the difference between creators who convert and creators who don't.

The good news? These aren't complex strategies that require months to implement. They're simple shifts you can make this week that address the real reasons people hesitate to subscribe.

Fix #1: The Invisible Value Problem

Right now, your biggest conversion killer is probably sitting right in your subscription call-to-action.

Most creators write some version of: "Subscribe to get more content like this" or "Join my community of readers." These phrases feel helpful to you, but they're conversion poison to potential subscribers.

Here's why: Your brain already understands the value of your content because you created it. But your readers are doing split-second mental math: "Is this worth my money?"

Generic value propositions don't help them with that calculation. In fact, those generic CTAs can actually hurt the value that a reader assigns to your content. Even if they don’t realize it.

Instead of "Subscribe for more content," try: "Get weekly conversion strategies I've used with Fortune 500 companies" "Join 1,200+ creators learning psychology-based engagement tactics" "Access the step-by-step guides behind these insights".

The difference is specificity. When someone reads "weekly conversion strategies," they can immediately picture what they're getting. When they read "more content," their brain has to work harder to understand the value.

This isn't about making bigger promises. It's about making clearer ones.

Test this: Look at your current subscription language. Would a stranger reading it know exactly what they'd get for their money? If not, get specific.

Fix #2: The Commitment Fear Barrier

Here's a psychological reality most creators ignore: People are terrified of signing up for "another thing to read."

Everyone's inbox is already overwhelming. When you ask someone to subscribe, you're asking them to commit to reading whatever you send, whenever you send it, for as long as they stay subscribed.

That's a scary commitment, even at $5/month.

The solution is setting clear expectations that reduce psychological resistance.

Instead of leaving people to guess:

• Tell them exactly how often you publish ("Two posts per week")

• Give them a sense of time investment ("5-minute strategic reads")

• Set realistic expectations ("Skip weeks when you're busy, the archive isn't going anywhere")

Compare these two approaches:

Scary version: "Subscribe to my newsletter for regular updates"

Clear version: "Get two 5-minute strategy posts each Tuesday and Thursday. Skip the ones that don't apply to you."

The second version feels manageable. The first feels like signing up for homework.

This also works because it demonstrates you respect their time, which builds trust. When people feel like you understand their constraints, they're more likely to believe you'll deliver value.

Fix #3: The Trust Gap

This is the conversion killer nobody talks about: Most creators ask strangers to pay them without providing any reason to trust them.

Think about it from a reader's perspective. They discover your content, maybe read one post, and suddenly you're asking for their credit card information. You might as well be asking them to loan money to someone they met five minutes ago.

Trust takes time to build, but you can accelerate it with simple social proof tactics:

Subscriber numbers: "Join 500+ creators" is more compelling than "Join my newsletter" because it shows others have already made this decision.

Results or credentials: Brief mentions of your background or results create credibility without bragging. "Strategies I've developed working with Fortune 500 companies" establishes expertise quickly.

Transparency: Share subscriber counts, talk about your writing process, acknowledge what you don't know. Vulnerability builds trust faster than perfection (One of my favorite topics, if you’re reading my Notes you know this!).

Simple testimonials: Even one sentence from a happy subscriber ("This helped me get my first 10 paid subscribers") provides social proof that your content works.

The goal isn't to prove you're perfect. It's to prove you're legitimate and that others have benefited from following you.

Why These Work (And Why You're Closer Than You Think)

These three fixes work because they address the real psychological barriers to conversion: unclear value, overwhelming commitment, and lack of trust.

Most creators assume they need better content or a bigger audience to start converting. But conversion problems are usually psychology problems, not content problems.

The encouraging news is that small changes can produce dramatic results. Clarifying your value proposition might double your conversion rate overnight. Setting clear expectations could eliminate the biggest objection preventing people from subscribing.

You don't need to become a completely different creator. You just need to remove the friction that's preventing people who already want to subscribe from actually doing it.

Start with one of these three areas this week. Pick the one that feels most relevant to your current situation and make the change. Find 2-3 of your best performing posts, and craft better CTAs using the above strategies.

Bonus Insight: Clearer CTAs not only improve your conversions, they also help you establish your authority and credibility with readers. Which, ironically, will also help your conversions! Now you’re working smarter, not harder!

That first paid subscriber notification might be closer than you think.

Which of these three barriers do you think has been holding back your conversions?

Ready to Grow Your Substack Into a Sustainable Business?

For 20 years I’ve helped everyone from startups to Fortune 500 companies design strategies to acquire, retain, and delight customers. Now, I’m sharing those same proven strategies with you here.

👉 If you’ve found this helpful, consider becoming a subscriber. Paid subscribers unlock access to my full library of 130+ articles, templates, and step-by-step guides—everything you need to grow your Substack with confidence.

Monthly subscriptions are $7.50, or $60 annually (a 33% savings).

Together, we’ll turn your Substack into a business that lasts.

Mack

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Backstage Pass teaches you how to better connect with your customers, readers, clients, or donors. The lessons shared here draw on my experience over the last 20 years building customer engagement strategies for companies like Adobe, Dell, Club Med, Ingersoll-Rand, and countless others. I give you real-world research, examples and tactics that show you how to create customer engagement efforts that drive real business growth.

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