Behind the scenes: A monetization funnel that actually works

"But how do you actually make money from a newsletter?"

"But how do you actually make money from a newsletter?"

I get this question almost daily. And I understand why—there's a massive gap between "start a Substack" and "make a living from it."

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Most creators are stuck in this bizarre limbo:

• Pouring hours into content that nobody pays for

• Too afraid to put anything behind a paywall

• Watching their bank account stay stubbornly unchanged

The uncomfortable truth? 91% of newsletters never make more than $100 a month.

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Here's what nobody tells you: It's rarely about the quality of your content. Some of the best writers I know make nothing, while creators with mediocre content are banking $10K+ monthly.

The difference isn't talent—it's structure.

Today, I'm pulling back the curtain on my exact monetization funnel. The same system that took me from $0 to five figures monthly in less than 6 months on Substack.

And I'm not holding anything back.

The Fatal Funnel Flaw Most Creators Make

Let's start with what doesn't work.

Most creators build what I call a "hope and pray" funnel:

1. Write amazing content

2. Hope people notice

3. Pray some decide to pay

4. Wonder why nobody's buying

This is the publishing equivalent of opening a restaurant in the middle of a forest with no signs, roads, or marketing—then wondering why you don't have customers.

I made this exact mistake when I started my first newsletter on a different platform years ago. Despite publishing religiously for 8 months, I had exactly zero dollars to show for it.

The problem? I had no intentional path to monetization.

The Backwards Blueprint That Actually Works

The monetization funnel I use now—the one that's generated over $91,000 in my first 7 months on Substack—works in reverse:

1. Start with the endpoint (what you want people to buy)

2. Build the bridge (content that naturally leads there)

3. Create the on-ramp (subscriber experience that builds trust)

4. Set up signposts (strategic CTAs that convert)

5. Amplify what works (double down on winning patterns)

Let me break it down with a real example from my own business.

Real-Life Example: My Exact Funnel Breakdown

Step 1: The Endpoint (The Monetization Goal)

I knew I wanted to create a mix of:

• Annual subscribers ($177/year)

• Premium workshops ($97-297)

• Digital products ($37-197)

• Limited coaching clients ($700/hr)

• Brand deals ($1000/deal)

Instead of just vaguely hoping for "paid subscribers," I had specific price points and offerings in mind.

Step 2: The Bridge (Content That Converts)

Here's where most people get it completely wrong.

Your free content should not just be "good." It needs to be strategically designed to lead to your paid offerings.

For example, when I launched my "Monetization Mastermind" workshop in February, I didn't just randomly promote it. I had previously published:

• A post breaking down how newsletters make money (establishing expertise)

• A post about a creator who went from $0 to $3K monthly (showing possibility)

• A post identifying the 3 biggest monetization mistakes (highlighting problems I solve)

This wasn't accident—it was architecture. Each piece of content created a bridge toward my paid offering.

Reality check: My highest-converting post wasn't my "best" post—it was the one most strategically aligned with my offer.

Step 3: The On-Ramp (Trust-Building Sequence)

New subscribers don't immediately buy. They need to trust you first.

My welcome email is intentionally designed in 5 parts:

1. Welcome + Question (builds connection)

2. Quick Win (demonstrates value)

3. Personal Story (creates relatability)

4. Common Mistake (establishes expertise)

5. Subtle Pitch (presents solution)

The sequence has a 72% open rate and has generated thousands in revenue just on autopilot.

Insider detail: Email part #3 (my personal failure story) gets the highest reply rate and creates the strongest connection. Vulnerability converts.

Step 4: The Signposts (Strategic CTAs)

Most creators either never ask for the sale or do it awkwardly.

I place strategic CTAs throughout my content using what I call "Value Bookends":

• Lead with undeniable value

• Present the natural next step

• End with additional value

For example, in a post about newsletter growth, I might write:

"These three strategies helped me add 5,000 subscribers in 30 days. If you want my complete system, including the exact templates I use, you can get access in my paid newsletter [LINK to offer or to subscription]. Even if you don't subscribe, make sure you're implementing the audience-building calendar I shared above."

Note how it's bookended by value, not pushy, and presents the paid option as the logical next step.

Step 5: Amplify What Works (Data-Driven Decisions)

This is the multiplier most creators miss.

Every week, I analyze:

• Which posts convert to subscribers

• Which emails convert to paid members

• Which offers generate the most revenue

• Which CTAs get the highest click rate

Then I double down on patterns that work.

For instance, I discovered that my case study posts convert 3x better than my how-to posts, despite getting fewer overall views. Guess what I now create more of?

Real Results From This Funnel

This isn't theoretical—it's exactly how I:

• Converted 7.8% of free subscribers to paid (industry average: 1-2%)

• Generated $12,400 from a single workshop launch

• Built to 48K+ subscribers in less than 7 months

• Created a consistent $17K+ monthly revenue from Substack alone

• Rise to Top 100 Bestsellers in Business

• Get brand deals that fit my audience and offer

But the best part? Once built, this system largely runs itself. New subscribers enter the top of the funnel daily and a percentage reliably converts to paid.

"But My Audience/Niche/Content Is Different"

I hear this objection constantly, and here's the blunt truth: The principles work regardless of your topic.

I've helped creators in niches from fiction writing to financial advice implement this same funnel structure with consistent results.

The formats change. The offers change. The price points change.

But the psychology of how people move from stranger → subscriber → customer remains remarkably consistent.

Your Next Steps: Build Your Own Funnel

If you're serious about monetizing your newsletter, you need to build your own version of this funnel.

Start by asking:

1. What specific paid offerings do I want to create?

2. What content naturally leads people toward those offerings?

3. What trust-building sequence can I create for new subscribers?

4. Where can I place strategic CTAs that feel helpful, not pushy?

5. How will I track what's working and double down?

Or...

Skip the Trial and Error Phase

Look, I spent years figuring this out through painful trial and error. Thousands of dollars in courses. Countless failed experiments. Multiple abandoned newsletters.

If you want to shortcut that process, I'm teaching my complete system in the upcoming Substack Money Map Bootcamp (April 15-17).

Over three days, I'll walk a small group through:

• Day 1: Building your Subscriber Conversion Machine

• Day 2: Creating your Perfect Paywall Strategy

• Day 3: Developing your Multiple Income Streams Blueprint

You'll leave with your complete monetization funnel built and ready to implement.

This isn't just theory—it's the exact system I used to go from launch to bestseller in under 60 days.

And because you're reading this post, you can join at the special rate of just $147 (regularly $297). But only until April 10th, end of the day. After this the early bird price offer expires.

Already a paid How We Grow subscriber? Your exclusive rate is just $97. (your special link access is at the bottom of this post)

Final Thought: The Real Differentiator

Here's what I've learned after helping hundreds of creators monetize:

The difference between those who make money and those who don't isn't talent, topic, or timing.

It's having an intentional system that guides people from first encounter to paid relationship.

Build that system once, and you'll reap the rewards for years to come.

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