"Is this even worth it anymore?"
I whispered this to myself at 9PM, staying up late again to write and finish a newsletter post.
I was doom scrolling social media and came across another “milestone celebration post” - one that had just crossed 10,000 subscribers.
I had ~200.
After months of late-night writing sessions. After countless LinkedIn posts promoting my work. After obsessively checking my open rates like my life depended on it.
Two hundred subscribers.
That's when a message pinged through from a subscriber (we’ll call him Michael):
"Just wanted to say your last post helped me raise my rates and quit my toxic job. I've been following big newsletters for years, but you're the only one who actually changed something for me. Worth every penny of that subscription."
That message changed everything.
Not because it was nice to hear (though it was). But because it revealed the mathematical truth that would transform my entire approach to building this business:
One subscriber who truly values your work is worth more than a thousand who don't.
And here's the really interesting part – the part no one seems to talk about:
You don't need an army of followers to quit your day job. You don't need to be "Substack famous." You just need a minimum viable audience of true fans who genuinely value what you offer.
In fact, I'm going to show you exactly why 1,000 true fans are all you need to build the freedom you're after. And why most newsletter writers stay broke chasing the wrong metrics with the wrong strategies.
Let me share what I discovered when I stopped obsessing over subscriber count and started focusing on creating genuine value for real people with real problems...
The Math That Changed Everything
Here's the hard truth most newsletter experts won't tell you:
Most of those big 10,000+ subscriber newsletters aren't making nearly as much money as you think.
When I was struggling to break 500 subscribers, I attended a private mastermind with several "successful" newsletter writers. Newsletters with 10K, 25K, even 40K subscribers.
And when we started talking real numbers? I was shocked.
Many were making less than $2,000 per month.
Why? Because they had thousands of subscribers who never opened their emails. Thousands more who never clicked. And only a tiny fraction who actually paid for anything.
Meanwhile, in that same room, there was a woman with just 870 subscribers making over $8,000 monthly.
The difference wasn't audience size. It was audience quality.
She had identified a specific problem her audience was desperate to solve. She had positioned her newsletter as the solution to that problem. And she had created offers her audience actually wanted to buy.
That's when I realized I had been playing the wrong game entirely.
I had been chasing vanity metrics instead of actual income. Growing for the sake of growing, rather than growing with purpose.
And that's when I started asking myself a different question:
"How many true fans do I actually need to quit my day job?"
The answer changed everything for me. And it might just change everything for you, too.
Your 1,000 True Fans Are Already Looking for You
Something interesting happens as your newsletter grows.
People come and go. Some subscribe, open one email, and disappear forever. Others stay but never engage. They're ghosts in your subscriber count.
But then there are those who show up. Week after week. Email after email.
They're the ones who comment on your posts. Who reply to your emails with thoughtful responses. Who like your Notes within minutes of publishing. Who buy your products without hesitation when you launch them.
I've watched this pattern play out as my Substack has grown. The same names appear in my comments section. The same people DM me with questions. The same subscribers are first in line when I release something new.
These are your true fans. And here's the thing – you don't need to make everyone happy. You don't need to appeal to the masses. You don't need to water down your message to reach more people.
You just need to speak directly, authentically, and helpfully to those 1,000 people who resonate deeply with your message.
Because those 1,000 true fans aren't just statistics. They're real people with real problems looking for real solutions. And when you focus on serving them – really serving them – something magical happens.
They become more than subscribers. They become advocates. Supporters. Partners in your journey.
And most importantly? They become the foundation of a sustainable business that can finally free you from that cubicle life you're trying to escape.
The Simple Math of Financial Freedom
Let's get into the numbers that really matter. The ones that will free you from that cubicle once and for all.
Start with your minimum financial freedom number. For some, that's $5,000 per month. For others, it's $10,000 or more. Whatever that number is for you, write it down right now.
Got it? Good. Now, let's break this down into true fan economics…
If you need $5,000 per month ($60,000 annually), you have several possible paths:
The Subscription Route:
500 subscribers at $10/month = $5,000 monthly
1,000 subscribers at $5/month = $5,000 monthly
The Digital Product Route:
50 people buying a $100 product each month = $5,000 monthly
100 people buying a $50 product each month = $5,000 monthly
500 people buying a $100 product each year = $50,000 annually
The Hybrid Approach (My Favorite):
200 paid subscribers at $5/month = $1,000 monthly
40 digital product sales at $100 each month = $4,000 monthly
When I first did this math, it hit me. I didn't need 50,000 subscribers. I needed a fraction of that number who truly valued what I offered.
(Now of course, if you sell a $500 course or a $3000 coaching package, etc. you need less loyal fans. But let’s keep simpler number for the sake of this post…)
But there's something else here that most "gurus" won't tell you:
The digital product route is often faster and more sustainable.
Let me explain.
When I launched my first digital product – a simple $50 masterclass on newsletter growth – I sold 47 spots in the first week. That's $2,350 from an audience of less than 1,000 subscribers.
Why? Because I had identified a specific problem my audience was facing (struggling to grow their newsletters) and offered a specific solution (my step-by-step system).
I wasn't asking for ongoing commitment. I was solving an immediate pain point.
This is why I believe so strongly in the "1,000 True Fans" model. You don't need everyone to buy everything. You just need a relatively small number of people who value your perspective enough to invest in the solutions you offer.
Think about it – even with just 1,000 subscribers, if only 10% purchase a $100 product from you over the course of a year, that's $10,000. Scale that to quarterly products, and suddenly you're at $40,000 annually.
All from just 1,000 people who genuinely care about what you have to say.
The Money Talk (And Why Most Writers Stay Broke)
Let's be honest for a second.
People get defensive when you talk about money. Especially in creative fields like writing.
"Shouldn't we just enjoy the craft?"
"Isn't it selling out to focus on monetization?"
"Real writers don't care about the money."
I've heard it all. And maybe you've thought some of these things yourself.
But here's the uncomfortable truth: Most writers stay broke not because they lack talent, but because they're afraid to monetize.
They've bought into the myth that there's nobility in struggling. That asking to be paid somehow diminishes the purity of their work.
And so they stay stuck in jobs they hate, writing on the side, dreaming of the day they can "someday" make a living from their words.
The Freedom Formula (How 1,000 True Fans Actually Works)
This is where Kevin Kelly's famous "1,000 True Fans" theory gets practical for newsletter writers.
The original idea is simple: If 1,000 people are willing to spend $100 a year on what you create, you've got a $100,000 business. But how does this actually work for newsletter writers in 2025?
Here's the freedom formula I've seen work consistently:
1. The Foundation: Value-First Content
Your free newsletter is the foundation. It's where you demonstrate your expertise, build trust, and identify the specific problems your audience needs solved. This isn't about holding back your best stuff – it's about giving generously to establish yourself as the go-to resource in your niche.
When I shifted from generic "tips and tricks" to deeply solving specific problems in my free content, my engagement skyrocketed. People started forwarding my emails. My subscriber count began growing organically through word-of-mouth.
2. The Ecosystem: Multiple Solution Paths
True fans want more than just information – they want transformation. Once you've identified the core problems your audience faces, create multiple ways for them to solve those problems at different investment levels:
Paid subscription tier ($5-10/month)
Digital products ($27-97 one-time purchases)
Masterclasses and workshops ($47-197)
Premium communities ($20-50/month)
Sarah, one of my earliest subscribers, first bought my $27 template bundle. Three months later, she joined my $97 masterclass. Two months after that, she became a founding member of my premium community at $37/month.
That's $27 + $97 + ($37 × 12) = $568 in annual value from ONE true fan.
Multiply that by 1,000? You've got a $568,000 business.
3. The Mindset Shift: Selling is Serving
Here's where most writers get stuck. They create amazing content, build trust with their audience, identify problems that need solving...and then stop right at the finish line.
They never make the offer. They never create the solution. They never give their audience the opportunity to go deeper.
Why? Because they've bought the lie that selling is somehow sleazy or beneath them.
The truth is exactly the opposite: If you've identified a problem your audience desperately wants solved, and you have the solution, not offering it is the selfish choice.
Think about it – many of your free subscribers are actively looking for deeper help from you. If you don't provide it in the form of paid solutions, they'll find it from someone else. Someone who might not care as much. Someone who might not deliver as much value.
Selling isn't taking. It's giving your audience the opportunity to transform.
The True Fan Mindset (Quality Over Quantity)
The strategy I'm sharing completely inverts the traditional newsletter growth model.
Instead of "grow first, monetize later," it's "serve deeply, grow intentionally."
When I embraced this approach, something fascinating happened. My conversion rates went up dramatically. My unsubscribe rates went down. And the quality of engagement from my audience reached levels I'd never experienced before.
Why? Because I stopped trying to appeal to everyone.
The True Fan Identification System: Finding Your 1,000
Here's where theory meets practice. How do you actually find these 1,000 true fans who will sustain your newsletter business?
I've developed what I call the "True Fan Identification System" after studying dozens of successful creators who've built sustainable businesses with relatively small audiences.
True fans aren't random. They share specific characteristics you can actively look for:
1. They Have a Burning Problem
True fans aren't just casually interested in your topic. They're actively struggling with something related to it. They're staying up late searching for solutions. They're spending money trying to fix it. They're emotionally invested in finding an answer.
When I started focusing my content specifically on helping newsletter writers turn their passion into profit, my engagement didn't just increase – it deepened. Comments went from "Great post!" to detailed stories about struggles, questions, and breakthroughs.
2. They Engage Meaningfully
True fans don't just consume – they participate. They comment thoughtfully on your posts. They reply to your emails with specific questions. They share your work unprompted. They're the first to join when you open something new.
I've noticed a core group of about 200 subscribers who consistently engage with almost everything I publish. These people aren't just readers – they're partners in the journey.
3. They Value Transformation Over Information
This is crucial: True fans aren't looking for more content to consume. They're looking for change. They want to move from their current situation to a better one, and they recognize that your perspective can help them get there.
When I launched my first paid workshop, I was nervous about the price point ($97). But my true fans didn't blink. Why? Because they weren't buying "content" – they were investing in transformation.
4. They Stick Around
I've noticed something interesting in my subscriber metrics. While my total list continues to grow, there's a core group that's been with me from the early days. They've watched my evolution. They've seen me make mistakes and correct course. They've celebrated wins alongside me.
These long-term relationships aren't just emotionally rewarding – they're financially valuable. My data shows that subscribers who have been with me for 3+ months are 4x more likely to purchase a digital product than new subscribers.
Finding Your True Fans: The Practical Approach
So how do you attract these people? It starts with clarity about who you're speaking to and what problem you're helping them solve.
Instead of trying to appeal to everyone interested in "newsletters" or "online business," I narrowed my focus to a specific segment: people who want to escape traditional employment by building a sustainable newsletter business.
This specificity changed everything. My content became more targeted. My solutions became more precise. And true fans started finding me because they recognized their own struggles in my words.
The most powerful tool for finding true fans isn't some fancy marketing tactic – it's relevance. When someone feels truly seen and understood through your content, they naturally lean in. They want more. They become invested in your perspective.
And that's exactly how you build a minimum viable audience that can sustain your business.
The Two Paths to 1,000 True Fan Freedom
Now, let's explore the specific paths to turning your 1,000 true fans into a sustainable business that lets you hand in your resignation letter.
There are fundamentally two routes to monetizing your newsletter, and understanding which one aligns with your strengths can accelerate your journey to freedom:
Path 1: The Subscription Model
This is the traditional approach – convince people to pay you monthly or annually for premium content. It works beautifully for some creators, especially those who:
Produce consistent, high-frequency content
Have specialized knowledge that's continuously valuable
Enjoy the predictability of recurring revenue
The subscription model has one massive advantage: predictability. When you know exactly how much is coming in each month, planning your exit from the corporate world becomes much less scary.
But it also has a significant challenge: it's usually the slower path to meaningful revenue. Converting free subscribers to paid typically happens at a 2-5% rate for most newsletters. That means you might need 20,000-50,000 free subscribers to hit 1,000 paid ones.
Path 2: The Digital Product Model
This is my preferred approach for most newsletter writers – especially those just starting out. Instead of asking for recurring payments, you create specific solutions to specific problems:
Digital products like templates, guides, or frameworks
Cohort-based courses or recorded masterclasses
Communities built around specific transformations
Digital products have a major advantage: they can generate significant revenue with a much smaller audience. A $97 product that converts at just 3% from an audience of 1,000 generates $2,910 in a single launch.
Do that quarterly and you're looking at $11,640 annually – from just 1,000 subscribers.
My Hybrid Approach (Get the Best of Both Worlds)
After experimenting extensively, I've found the most powerful approach is combining these two models:
The Foundation: Free newsletter that provides genuine value and builds trust
The Gateway: Low-priced digital products ($27-97) that solve specific problems
The Experience: Mid-priced workshops and masterclasses ($97-297)
The Community: Premium subscription for ongoing support and implementation
This creates a natural value ladder that allows true fans to engage at their comfort level. Some will only ever buy your $27 product. Others will join everything you offer. Both are valuable.
Sarah, one of my first 500 subscribers, has spent over $800 with me in the past year. Not because I'm a master salesperson, but because I've created solutions to problems she actually has.
Multiply that by 1,000 true fans, and you can see how quickly the math works in your favor.
The Money Talk: Why Selling Actually Matters
I need to address something directly that holds back so many talented newsletter writers:
The discomfort around selling.
I get it. We're writers. We love the craft. We care about our readers. And something about asking for money feels... uncomfortable.
But here's the truth that transformed my own relationship with selling:
Monetization isn't just about you making money. It's about creating deeper transformation for the people who need it most.
When someone pays for a solution, something powerful happens:
They become more committed to implementation
They value the content more highly
They get better results
I've seen this repeatedly. The free subscribers who eventually purchase something from me implement at a dramatically higher rate than those who consume only my free content. They get better results. They experience deeper transformation.
And here's the part most writers miss:
Many of your free subscribers actively want more help from you. They're silently hoping you'll offer something deeper, more structured, more comprehensive than what you can provide for free.
If you don't create that solution, they'll find it elsewhere – from someone who might not care as much or provide as much value as you would.
This isn't about "selling out." It's about creating the deeper pathways of transformation that your most committed readers are already looking for.
Are You Ready for True Fan Freedom?
Here's the truth about where we stand right now in the online creator economy:
The window of opportunity for building a sustainable newsletter business has never been more open. Platforms like Substack are creating unprecedented opportunities for writers to connect directly with their most dedicated readers.
But most newsletter writers will miss this opportunity entirely. They'll stay stuck creating "content" without ever building a business. They'll keep chasing subscriber counts instead of creating real value. They'll remain uncomfortable with monetization until their passion project eventually becomes another abandoned dream.
It doesn't have to be this way for you.
The path to freedom isn't about reaching the masses. It's about serving a small group of people so effectively that they gladly invest in the solutions you provide.
Let's quickly recap what we've covered:
You don't need tens of thousands of subscribers to build a sustainable newsletter
Just 1,000 true fans spending $100/year with you creates a six-figure business
True fans care deeply about the problems you help them solve
You can monetize through subscriptions, digital products, or a hybrid approach
Selling isn't selfish – it's providing deeper transformation to the people who need it most
The question isn't whether this approach works. I've seen it transform too many newsletter businesses (including my own) to doubt its effectiveness.
The real question is: Are you ready to build your minimum viable audience and finally create the freedom you're after?
📌 Your Next Step: Join the Six-Figure Substack Growth Masterclass
If you're nodding along with what you've read, if something in this approach resonates with your vision for your newsletter business, I'd like to invite you to join hundreds of other newsletter writers in my Six-Figure Substack Growth Masterclass.
Inside, I'll show you:
My complete system for identifying and attracting your 1,000 true fans
The exact templates I use to create digital products that sell consistently
How to craft offers your audience naturally wants to buy
The proven frameworks for monetizing without feeling salesy
Step-by-step implementation plans to replace your day job income
This isn't about building a massive audience for vanity's sake. It's about building a focused, valuable audience that genuinely appreciates what you offer – and is happy to invest in the solutions you provide.
You can join 100’s of other writers in the masterclass below:
Your freedom isn't measured by subscriber count. It's built on the foundation of true fans who value your unique perspective and the solutions only you can provide.
Question: Are you actively growing your newsletter? Drop a link to your best Substack post below. I’ll read through and restack any that might resonate with my audience.
I love Substack - and I love writing - BUT each serious post takes me 10 hours: 1. Idea? 10 seconds 2. first draft? 2 hours 3. Research? 2 hours. 4. Editing? 2 hours. 5. Polishing and adding links? 2 hours 6. Overall polish 2 hours - OK - I lied not 10 hours but 10 hours and 10 seconds! ☮️❤️🍷
You speak to ME …Wes…. Because I have been planning my Newsletter while I finish up my book (working on the cover & formatting). I appreciate the reinforcement for what I was “bumbling” toward & couldn’t quite “see” & articulate. Thanks and More Thanks!🌟