Want to Hit 100 Paid Subscribers? See What 32 Substack Bestsellers Did Right - Part 1
Strategies that convert free readers into paid members
👋 Hey, I’m Ciler and welcome to a 🔒 subscriber-only edition 🔒 of Newsletter Circle. I research Substack Bestsellers’ behind-the-scenes to help you grow and monetize your newsletter.
If you’re not a paid member, here’s what you missed:
If you’re thinking about launching paid subscriptions, or maybe you just did, remember: you’re not alone if it feels overwhelming.
Putting a price on your work isn’t easy. It’s vulnerable.
You’re not just asking people to read your writing. You’re asking them to believe in it enough to pay for it. And that takes courage.
But once you take that leap, a new challenge appears: How do you actually grow your paid membership?
According to Substack Report analyzing 75K Substack newsletters, 36% of newsletters offer paid subscriptions.
However, we know that only a small percentage manage to grow.
Because growing a paid audience isn’t just about flipping a switch. It takes time and real effort.
That’s why I asked 32 Substack Bestsellers one powerful question:
What was the most effective action that helped you reach your first 100 paid subscribers?
Why It Matters to Earn a Substack Bestseller Badge
Along that journey, hitting 100 paid subscribers is a big deal.
It’s more than just a round number.
It’s a signal that your work resonates. It’s a credibility marker. It tells readers: “Others have found value in this, maybe you will too.”
Substack understands how important that milestone is. That’s why they created a badge system to celebrate it, and help creators build credibility as they grow.
The very first badge is the White Badge, which appears on your Substack profile once you reach 100 paid subscribers.
With this badge, you officially become a Substack Bestseller.
And let’s be honest. This kind of recognition matters.
We’re wired to respond to progress we can see. Think about sports competitions: even the most intrinsically motivated athletes still want to see the finish line, hold the trophy, wear the medal. It’s not just about the reward, it’s about making the achievement tangible.
That’s what Substack’s Bestseller badges do. They give you something to work toward and something to proudly show when you get there.
You don’t need a huge list to become a Bestseller
There is no one-size-fits-all answer to becoming a Bestseller. It widely depends on how one positions their newsletter, the topic of the newsletter, and the time one allocates to publishing and distributing content.
And each creator has a unique journey.
However, there are some repeated insights that pop up and some surprising executions. So in this article, you’ll find what makes 32 creators a Substack Bestseller, including:
3C Rule: Content, Consistency and Community
What truly makes content great
How to create FOMO with free content that sells itself
How they turn their paid members into a Community
Smart paywalling strategies that they apply to attract new paid members
What matters most in the long run
This isn’t about growth hacks or shortcuts. It’s about creating something people genuinely want to read, support, and share.
And here’s the best part:
You don’t need tens of thousands of subscribers to become a Bestseller.
Out of the 32 creators I interviewed, 29 of them had fewer than 10,000 subscribers:
0-1,000 subscribers → 1 newsletter
1,000-5,000 subscribers → 13 newsletters
5,000-10,000 subscribers → 15 newsletters
10,000+ subscribers → 3 newsletters
So if it’s not massive lists or viral growth tactics, what is their secret?
That’s exactly what we’ll explore together.
If you’re working toward your first 100 paid subscribers and you're growing with a relatively small list, this article is especially for you.
P.S. This is just Part 1 of the series. Stay tuned for upcoming posts where we’ll keep revealing how Substack Bestsellers grow their paid audience.
A huge thank you to all the Bestseller creators who contributed to creating this article by sharing their most effective strategies!
Tony Teegarden, Abhinav Upadhyay, Julie Bogart, Amanda Saint, Jacob Bartlett, Matthew Long, Adam Ming, Jill Schildhouse, TOGS by Hadley Hammer and Kellyn Wilson, Ahmed Baba, Dr. Angela Kingdon, Jesse Colombo, Sarah McColl, Tim Fitzpatrick, Ryan B. Anderson, Satya Robyn, Petya K. Grady, Mirek Stanek, Bernard Lane, Lily Canter, John Roedel, Prof. Kimberly Nicholas, Christine Sneed, Laura Calder, Irina Slav, Richard Toad, Lawrence M. Krauss, Jeff Ignacio, Andrea Bartz, Jamie Klein, Brooke Warner, ashley ray
Here are the biggest takeaways and more surprising ones:
The biggest emphasis was on putting high-quality content, delivering the highest value and sharing it consistently.
They approach their newsletters not as a list of e-mails but as a community which they can craft a conversation. This is how Substack truly works.
The secret to becoming a Bestseller with a relatively small list lies in authenticity. Each creator brings something unique, whether it’s owning a specific niche, original voice, or exceptional depth in their content.
They’re obsessed with creating the most relevant paid benefits for their community. So they relentlessly experiment and make iterations.
Some creators give everything for free. Despite having no paywalls, they became Bestsellers thanks to the support of a community that deeply valued what they offered.
They managed to turn paywalling into a magnet for paid members with some unconventional methods, such as reverse paywalling.
Their biggest superpower is staying resilient and showing up even when they don’t see any results.
How 32 Substack Bestsellers Reached Their First 100 Paid Members
1. Apply 3C Rule: Content, Consistency, Community
It’s difficult to separate high-quality content from consistent publishing, which leads to building a community of readers. This is what I call as 3C Rule:
Create high-quality content
Publish consistently
Approach your newsletter with a community mindset
At first glance, this might seem like a simple formula.
However, it requires relentless writing, a deep understanding of your audience, and constant experimentation.
Some creators naturally develop this over time, while others approach it with clear intention from the start.
Jill Schildhouse’s answer is a great demonstration of how they combined the power of content, consistency and community to gain their first 100 paid subscribers:
“I think we gained a lot of traction quickly by joining forces as two known journalists in the industry, and leaned into the inherent credibility that came from our combined 40+ years of media experience.
From there, we consistently posted well-researched content on a weekly basis, wove in plenty of personal anecdotes our audience could relate to and take action on, and hosted monthly Ask Us Anything sessions (we call them Top Tier Talks) as a value-add for paid subs.”
Andrea Bartz and Lawrence M. Krauss also emphasized the importance of providing true value through their content consistently:
“Our most effective strategy to reach our first 100 paid members is publishing consistently high-quality content that readers can't find anywhere else.
I see a bump in paid subscribers anytime someone I follow publicly recommends my Substack publication, but I don't pay or even directly ask subscribers to help spread the word; I focus on publishing valuable posts that readers enjoy and feel eager to share. Word of mouth is everything!”
“I think the most effective action was to produce content of interest with a regular frequency.”
Ahmed Baba shares political news analysis in his newsletter, and he doesn’t paywall his work at all.
Instead, he focuses on audience engagement and quality work.
“I reached bestseller status by focusing on high-quality content and direct engagement. I don’t paywall my work, reply to all subscribers, and avoid chasing headlines.
Instead, I write 2-3 in-depth pieces per week, offering contextualized political analysis. Substack Notes has made reader engagement even easier, and the recommendation feature has helped grow my subscriber base.”
It’s no surprise that every Substack Bestseller got there through a mix of high-quality content, consistent publishing, and some form of community engagement. These are the pillars of any successful newsletter business.
But each creator had their own emphasis.
Some leaned heavily on consistency, just showing up week after week. Others focused almost entirely on delivering the highest quality writing they could. Some prioritized community and personal connections.
And many said it was the combination of these elements that made the difference.
Let’s take a closer look at what they each highlighted and what the main driver was for reaching 100 paid subscribers.
2. Create High-Quality Content
Without great content, no strategy will get your newsletter read.
But, great content is a bit of an arbitrary term, so this takes us to another question:
What truly makes content great?
Great content stays at the intersection of three main criteria:
Understand your audience and address a need / solve a problem
Be authentic
Getting excited about the topic you write about
➜ Understand Your Audience and Craft the Most Relevant Offer
It is possible to create impact only by providing value, whether functional or emotional. For this, you need to define a target audience, understand them and help them to navigate a specific pain point.
Once you define a pain point/need, you can create an irresistible offer as Adam Ming did:
“I found a unique way to solve a specific problem.
I was constantly trying to understand the customer and packaging an offering that is a unique way to solve their specific problem, once mine, and the problem was that some people have a burning desire to create but are not doing it.
Because they don’t have:
Permission
Structure
Peers to do it with
Once you understand it, it’s about creating that irresistible offer.
I know I’m writing about the creative practice, most people will approach it as a diary, my method was to try and figure out what the customer needs, i.e., I’m writing as a service, one of these ways I do this is asking directly. For example, I ask readers to introduce themselves and tell me their next 3 steps, or I do 1-to-1 mentorships and I use that to see where the pain points are.
I look for patterns in their responses, and try and tailor an offering accordingly.
I mentioned the 3 patterns I noticed readers needed so I create an offering that gives them that: permission, structure, and community.
Permission to start small, structured daily 10-minute prompts, community through celebrating their work and giving them a space to share and express themselves.”
Jamie Klein is writing about what’s going on in the paddock of Super Formula, Japan’s fastest racing series. He’s a Substack Bestseller with just 830+ subscribers, one of the highest conversion rates on the platform. He also emphasized the importance of knowing your audience while serving enough content to convert free subscribers.
“It might sound obvious, but I think the key has been knowing my audience (I'm writing about an extremely niche topic but with a loyal fan following) and providing the content that I know they want to read.
And providing enough content for free to lure in new paid subscribers I guess has also helped.”
Align your content format with audience expectations
Mirek Stanek has published 60 articles without missing a single week.
Beyond just showing up regularly, he’s figured out exactly what kind of guidance his audience is looking for and he delivers it through highly actionable content:
“I either share my personal experiences (‘this is how I did that’ rather than ‘this is how you should do it’) or share practical materials (templates in Notion, Google Docs, Sheets or predefined whiteboards in FigJam).
Each of these materials were battle tested in my work. Meaning - the theory behind them is widely know and I always reference the original books where the ideas or frameworks come from. But on top of that I also show people how I implemented these things in my specific field of Engineering Leadership.
For example ‘Engineering Strategy Framework’ comes from the excellent book by Richard Rumelt - ‘Good Strategy / Bad Strategy’. But translating this wisdom into my field took me long months of work and then years of using them in practice. And my experience is what I share with my audience.”
Jeff Ignacio provides GTM leaders and operators with practical, actionable advice on building, scaling, and managing their businesses. His paid subscribers get access to customizable templates they can directly apply to their teams.
“It's the templates that drive paid subscriptions for my newsletter.”
Create a space for connection rather than a publication
Petya K. Grady is running a newsletter for book people who’ve lost their way and emphasizes the importance of clarifying her niche and being in a conversation with her readers.
“The most effective growth action for me has been clarifying my niche and thinking about my newsletter as a conversation, not a ‘publication’. A Reading Life is not a way for me to throw content at people. It's a place where we talk.
Once I knew what I wanted to talk about and who I wanted to be in conversation with, a lot of decisions started making themselves: what to write about, how often to publish, what tone to use as I address readers, how to think about losing readers, etc.”
➜ Be Authentic
In a world where readers are overwhelmed with endless content, it’s crucial to be differentiated by showing your authentic self.
Here is how you can apply authenticity to your newsletter: