The Psychology Behind a Six-Figure Newsletter in 2025
(And Why Most Writers Are Getting It All Wrong)
When I was thinking about starting my newsletter, I went where every self-respected man goes to learn something: YouTube.
"You need paid subscriptions to make money on Substack," the “guru” on the video told me confidently.
To me that just didn’t seem right. When I mentioned it to my mom, she agreed. It’s like making a living running a coffee shop. You have to sell a LOT of cups of coffee to make it worth it…
I knew to run a profitable newsletter, I’d need to get a LOT of people to convert from “free” to “paid” subscriber.
My “Aha!” Moment
Last year, I was exactly where you might be right now. After three months of hustling with the traditional Substack approach, I had a whopping ~100 subscribers (mostly family and friends) and exactly two paid subscribers (thanks, Mom and Dad).
I was following all the "expert" advice:
Write killer free posts
Put your best stuff behind a paywall
Beg for subscribers everywhere
Hope people pay $8/month
And it was killing me. Every time I typed "please subscribe!" at the end of a post, I felt my credibility dying a little more.
So, I quit. Straight up put my Substack on the shelf and walked away.
But here's where it gets interesting...
The Accidental Discovery That Changed Everything
When I came back to Substack this year, I noticed something that nobody was talking about. The fastest-growing newsletters weren't begging for subscribers. In fact, they weren't even promoting their newsletters directly.
That's when I discovered what I now call the LinkedIn-Substack Flywheel, and everything changed:
3,300+ engaged subscribers (up from !100)
35-40%+ open rates
5-10 product sales daily
A path to six figures that doesn't require paid subscriptions
It’s all about attracting your ideal subscribers, instead of straight-up promotion.
The Platform Multiplier Effect: Why LinkedIn + Substack = Magic
Here's what most newsletter writers don't understand: The real money isn't in paid subscriptions. It's in understanding platform psychology.
Think about it:
LinkedIn is where professionals go to learn
Substack is where they go to dive deeper
When you combine both, something magical happens
The psychology at play here is fascinating…
1. Social Proof Amplification
Every time someone sees your content on LinkedIn AND Substack, you build a little bit more authority. It's like seeing your favorite actor in multiple hit movies - your credibility multiplies with each touchpoint.
I noticed this when readers started DMing me saying, "I see your content everywhere!" Even though I was only posting on two platforms. When you link two platforms and cross-promote, it looks like you’re everywhere, all the time (when you’re really not).
You do what you do best: create great content.
Let LinkedIn & Substack do what they do best: push your content out to your ideal subscribers.
You don’t have to be everywhere. Choose one main external platform (in my case LinkedIn) and a tool to dive deeper with your audience (Substack, an email provider, etc.)
2. The Curiosity Gap
Every LinkedIn post creates what psychologists call a "curiosity gap" - that irresistible urge to learn more about someone who just shared a valuable insight. When they visit your profile and discover your newsletter, it feels like finding a hidden treasure.
No begging required. They come to you.
This is why I don’t recommend “educating” people too much in your LinkedIn posts. It’s more about gaining attention and peaking your audience’s interest. Once they’re interested, they’ll visit your profile and head to your Substack…and hit “subscribe.”
Nobody wants to read another “5 steps to do…” or “10 ways to have…” Like nobody.
But, people are interested in watching an engaging video, being inspired, being a little entertained, etc. When you can do that with your content, you’ll peak interest.
Don’t give it all away on the first date. This approach is like building a future relationship with someone. You wouldn’t give away your entire life story on the first date, would you? So don’t give away all your secrets, knowledge, and insights in your LinkedIn posts.
3. The Netflix Effect
Just like Netflix keeps you watching with "if you liked this, you'll love this," each piece of content naturally leads to the next. One LinkedIn post leads to your profile, which leads to your newsletter, which leads to your products…
It's a natural flow that feels effortless to your audience.
Once a new subscriber enters your ecosystem, they’re hooked. You won’t even have to ask people to buy from you: they’ll be asking YOU what you can offer to help them.
The Pain Most Writers Face
I talk to newsletter writers every day who are:
Struggling to build an audience beyond friends and family
Fighting for every paid subscription
Trading time for pennies
Feeling like they're shouting into the void
I get it because I lived it. Those first three months of 2023 felt like pushing a boulder uphill.
But it doesn’t have to be that way…
The 2025 Newsletter Reality
As we head into 2025, two massive trends are colliding:
Growing newsletter fatigue (people are tired of subscriptions)
Increasing demand for specific solutions
The winners won't be the ones with the most subscribers - they'll be the ones who understand the psychology of platform synergy and know how to monetize through digital products instead of (only) subscriptions.
Don’t get me wrong; turning on the “paid subscriber button” on Substack is great. But, I wouldn’t recommend relying solely on paid subscribers for the long-term. Diversify with digital products.
The Solution: The LinkedIn-Substack Flywheel
This week, I’ve opened up the LinkedIn-Substack Flywheel Masterclass, where I’m breaking down the exact psychological triggers that drive newsletter growth and product sales.
You'll learn:
How to create content that makes people think "I need to hear more from this person"
The exact templates I use to drive 10-20+ new subscribers daily
How to turn your newsletter into a product sales machine without feeling salesy
My LinkedIn Profile Audit Checklist that turns visitors into subscribers
The psychological triggers that turn readers into buyers
But here's the catch: I'm limiting it to 50 students to ensure everyone gets detailed attention.
Why This Matters Now
Listen, I'm not sharing this to brag. Earlier this year, I was burnt out from trading time for money with 1-on-1 client work. It felt like a treadmill I couldn't get off.
Now, thanks to the LinkedIn-Substack Flywheel, I've built a business model that requires less than 10 hours per week and is on-track for six-figure revenue in 2025.
The opportunity is here, but the window won't stay open forever. As more writers catch on to the platform multiplier effect, the advantage will go to those who act first.
If you're ready to build a newsletter that generates real revenue without the subscription struggle, join me in the LinkedIn-Substack Flywheel Masterclass by clicking the button below:
Remember: People aren't tired of newsletters. They're tired of the old way of doing newsletters. Be the change.
See you inside, Wes
P.S. The masterclass is limited to 50 students and will close once we reach capacity. If you're interested, don't wait too long to decide.
When you join today, you’ll receive a link to our Private Community. The masterclass & Flywheel Playbook will be sent out on Monday Dec 23rd to watch On Demand.
P.P.S. What other psychology “hacks” do you use in your newsletter? Did any of these stand out more to you than the others?
Your Mom is pretty smart!
Excellent advice. Is LinkedIn Premium necessary though? Cheers