I Reverse-Engineered the Headlines of His Six-Figure Substack
Here Are 5 Frameworks You Can Use In Your Next Post
I’ve been following Matt Giaro for years.
Bought his courses. Watched him build exactly the kind of business I want. He’s crushing it here on Substack.
I’m just a student at the feet of a master, still trying to get traction.
So instead of guessing what works, I decided to reverse-engineer his headlines to sunderstand ee why they work so well.
But first, if you’re not already subscribed to Matt’s newsletter, go do that now. Seriously. I’ll wait…..
Okay good. Let’s continue.
This Isn’t About Copying
Matt’s exact formulas might not work for my audience. They might not work for yours either.
But understanding the patterns behind what works gives you a foundation to test from.
This isn’t about copying. It’s about learning the underlying structure so you can adapt it to your own voice and audience.
The Process Was Simple
Here’s what I did:
Step 1: I collected about 25 of Matt’s long-form Substack post titles.
Step 2: I fed them to Claude with one simple prompt: “Analyze and categorize these headlines. What patterns do you see? Why are they working?”
Step 3: Claude came back with a full breakdown. Five categories. Patterns. Power words. Psychology.
I’m always blown away by how easy it is to do this. But you have to be careful to use it ethically.
This is about learning principles, not plagiarizing someone else’s work. The goal is to understand WHY something works so you can create your own version. Not to copy-paste someone else’s success.
What Claude Found: The 5 Headline Frameworks
Here’s what came out of the analysis:
Framework 1: Contrarian/Anti-Advice
Pattern: “Everyone says X. I say Y.”
Example from Matt: “My Substack Anti-Growth Plan (That Actually Worked)”
Why it works: Creates curiosity through contradiction. Positions you as an insider with hidden knowledge. Makes readers question what they thought they knew.
More (made-up) examples:
Stop Building Your Personal Brand. Build This Instead”
“My Anti-Productivity System (That Actually Worked)”
“Why I Quit Morning Routines (And Why You Should Too)”
“If You’re Still Cold Calling, Stop. Do This First”
“Your Marketing Strategy Is Backwards. Here’s Why”
Framework 2: Case Study/Experiment
Pattern: “I tried X for [timeframe]. Here’s what happened.”
Example from Matt: “I Stopped Posting Long-Form Posts on Substack for 3 Weeks. Here’s What Happened”
Why it works: Specific numbers create believability. Readers get vicarious learning without having to take the risk themselves. Timeframes add concrete evidence.
More (made-up) examples:
“I Stopped Networking for 6 Months. Here’s What Happened to My Revenue”
“17 Lessons After Running Workshops for 17 Months”
“Why I Fired My Three Biggest Clients (And Tripled My Income)”
“I Posted on LinkedIn Daily for 90 Days. Here’s What I Learned”
“How I Replaced My $200K Salary in 18 Months”
Framework 3: Problem Diagnosis
Pattern: “Here’s the REAL reason you’re stuck.”
Example from Matt: “Your Small Audience Isn’t the Problem. This Is”
Why it works: Speaks directly to the reader’s pain. Promises clarity. Reveals an unexpected insight that reframes the problem.
More (made-up) examples:
“Your Pricing Isn’t Too Low. Your Positioning Is Too Vague”
“Why You Can’t Find Clients (And It’s Not Your Marketing)”
“The Ugly Truth About Why Your Webinars Don’t Convert”
“Your LinkedIn Strategy Isn’t the Problem. This Is”
“Why Smart Consultants Stay Stuck at $5K Months”
Framework 4: How-To/Template
Pattern: “Here’s the exact system/method.”
Example from Matt: “3 Simple Substack Newsletter Templates (That Pull In Readers & Buyers)”
Why it works: Numbers create specificity. Words like “simple” remove intimidation. The promise is actionable, not just theoretical.
More (made-up) examples:
“5 Email Templates I Use to Close 60% of My Proposals”
“The Simple Client Onboarding System That Saves Me 10 Hours a Week”
“How to Write a Consulting Proposal in 30 Minutes (Template Included)”
“3 Discovery Call Questions That Qualify (or Disqualify) Clients Instantly”
“My 15-Minute Daily Planning System for 6-Figure Coaches”
Framework 5: Mindset/Inner Game
Pattern: “Fix your thinking first.”
Example from Matt: “How To Build An Unstoppable Writing Habit (That Doesn’t Rely on Lumpy Emotions)”
Why it works: Addresses emotional blocks, not just tactics. Readers feel seen. Promise of mental breakthrough
More (made-up) examples:
“How to Raise Your Rates When You’re Terrified of Losing Clients”
“The Imposter Syndrome Trap (And How I Finally Escaped It)”
“How to Stop Underpricing Without Feeling Like a Fraud”
“Building a Practice While Battling Burnout: What Actually Helped”
“How to Fire Bad Clients (Even When You Need the Money)”
The Two-Part Structure
Most of the winning headlines have two components:
PART 1: The Hook Creates tension through:
Contrarian statement
Personal confession
Problem identification
Bold claim
Unexpected experiment
PART 2: The Payoff Promises resolution through:
“Here’s what happened”
“Here’s what you should do instead”
“This is the real problem”
“Here’s how I did it”
“And why you should too”
Examples of the Two-Part Structure:
Hook: “I Stopped Taking Discovery Calls” Payoff: “Here’s What Happened to My Close Rate”
Hook: “Your Funnel Isn’t the Problem” Payoff: “Your Offer Is”
Hook: “Why I Fired My Best Client” Payoff: “And Why It Was the Smartest Business Decision I Ever Made”
Hook: “The Simple Workshop System” Payoff: “That Books Out My Calendar 3 Months in Advance”
Use the frameworks and create two-part headlines like this, and you’ll start seeing what pulls people in.
You won’t nail it every time, but you’ll have a structure to test against.
Full Transparency: I Haven’t Tested These Yet
I haven’t tested these frameworks on my own headlines yet.
And that’s okay.
Matt’s frameworks may not work for me. They may not work for you and your audience. But at least when you understand (and internalize) these frameworks you can test them, and see what works.
The point isn’t to copy his exact approach (and it’s definitely not to copy his headlines).
It’s to understand what makes his headlines work, then adapt that to your own content and style.
How You Can Do This With Any Creator
The process that I used you could use to learn from any creator who you think is doing a good job.
Here’s the step-by-step:
1. Pick a creator in your space who’s crushing it. Someone whose business model you admire, whose audience looks like yours.
2. Collect 20-30 of their best-performing headlines or posts. You want enough to see patterns, but not so many you get overwhelmed.
3. Feed them to Claude with this prompt: “Analyze and categorize these headlines. What patterns do you see? Why are they working?”
4. Ask Claude to create a framework you can reference. Something structured and reusable.
5. Test and adapt to your own voice and audience. Don’t just copy. Learn the structure, then make it yours.
The Real Lesson: Learn the Structure, Then Make It Yours
Here’s your action plan:
Pick ONE headline framework from this analysis. Or do the analysis on your own favorite creator and pick one of those frameworks.
Adapt it to your voice and content.
Write and share a post using it.
Measure the results and try another framework for the post after that. Keep going until you find a few that work for you and your audience, then repeat.
I Built Something You Can Use
After doing this analysis, I combined these frameworks with a previous study I’d done of successful headlines across Substack and Medium.
Then I turned it all into a “Headline Wizard” that generates headline ideas.
You give it your topic or a draft post. It gives you options using these and other proven frameworks.
It’s free. If you’re subscribed, reply and I’ll send you the link.
Not subscribed yet? Sign up and you’ll get it in your welcome email.
Hit reply or leave a comment and tell me: Which framework will you try next?