Want to Hit 100 Paid Subs? See What 17 Substack Bestsellers Did Right - Part 2
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:
Want to Hit 100 Paid Subscribers? See What 32 Substack Bestsellers Did Right - Part 1
3,000 Subscribers and Already a Substack Bestseller—It’s Possible!
Reaching your first 100 paid subscribers on Substack is one of the most defining early milestones for creators running a paid newsletter.
It’s the point where your paid newsletter business got solid validation about your progress.
Remember our popular article about how 32 Substack bestsellers reached their first 100 paid subscribers? Here are some of the golden takeaways from our first article:
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.
They’re obsessed with creating the highest quality content on a consistent base. So they relentlessly experiment and make iterations to craft the most relevant paid benefits for their community.
They managed to turn paywalling into a magnet for paid members with some unconventional methods, such as reverse paywalling.
And now, we’re back with Part Two, this time spotlighting 14 more Substack bestseller publications run by 17 newsletter operators and the most effective strategies they utilized to reach their first 100 paid subscribers.
After emphasizing content, community and consistency in Part One, this time, we’re diving deeper into the marketing strategies that helped them get there.
Each of these creators has a unique story, but clear patterns emerged in how they approached paid subscriber growth. In this article, you’ll learn how they:
Use discounts to convert free subscribers
Personally reach out to loyal readers to encourage them to upgrade
Promote their paid offerings across social media consistently
Show transparency and honesty about why they charge
Experiment with paid ads to scale what’s already working
Out of the 14 publications featured in this article, 9 of them had fewer than 5,000 total subscribers when they hit 100 paid members:
0–1,000 subscribers → 2 newsletters
1,000–5,000 subscribers → 7 newsletters
5,000–10,000 subscribers → 2 newsletters
10,000+ subscribers → 3 newsletters
This breakdown proves a powerful point again:
You don’t need a massive list to become a Substack Bestseller if you know your audience, provide real value with your content and apply effective promotion.
Let’s continue exploring what it takes to convert free readers into your first 100 paying members.
💡 Here are the biggest takeaways and more surprising ones:
Whether it was texting their network, launching a discount, or paywalling their best content, these creators took action early and often.
Self-promotion wasn’t something they avoided. They didn't rely on one big announcement but made their paid offering part of the conversation over time.
The most successful newsletters didn’t push paywalls randomly. They matched paid offerings with timely events, personal stories, or high-value projects, so readers had a reason to subscribe now.
Whether through 1:1 outreach, exclusive perks for loyal fans, or community-building in Notes, they focused on depth over scale. And it worked, even newsletters with under 800 subscribers became bestsellers.
Transparency about running a newsletter business, intentional pricing strategies, and thoughtful onboarding were recurring themes. These writers weren’t shy about monetizing; they embraced it.
They each grew in their own way, but none of them grew by accident.
There’s no one-size-fits-all playbook, but there is one common thread: each creator found what worked for them through experimentation, iteration, and trust in their unique voice.
Huge thanks to , , & , & Nick Axelrod-Welk, , & , , , , , , , and for generously sharing their behind-the-scenes strategies.
How 17 Substack Bestsellers Reached Their First 100 Paid Members
1. Offer discounts regularly
Understanding the power of discounts can give you the momentum you need to boost your paid subscriber count.
Many successful Substack writers have used discounts strategically during launches, relaunches, or after building up a loyal free audience to convert their interest into paid support.
💡 Why discounts matter
Discounts give readers a nudge. Many of your most engaged free subscribers are already on the edge of upgrading. A timely discount can give them just the push they need.
They feel like a reward. Special offers can act as a form of recognition, showing your most loyal readers that you see and appreciate their support.
They create urgency and FOMO. When readers know a discount is only available for a limited time, they're more likely to act quickly rather than delay.
They build conversion momentum. A smartly timed discount can create a wave of upgrades that pushes your newsletter toward key business milestones.
They encourage annual subscriptions. If your discount is tied to yearly plans, it encourages annual subscription. This reduces churn risk and increases long-term revenue. Readers are more likely to commit upfront when they feel they’re getting extra value.
But Not All Discounts Are Equal
According to my analysis of 75,000 Substack newsletters, the average monthly subscription price is $10.
Most creators offer a baseline discount through annual billing. For example, if their monthly price is $10/month, they charge $100/year instead of $120/year.
But it’s not the kind of discount we’re talking about here.
What really moves the needle are seasonal or limited-time special discounts that sit on top of your standard pricing structure, those offers that spark action right now.
When choosing your discount range, consider factors like:
Your audience size: A larger audience allows for broader campaigns and bigger waves of conversion.
Your niche: Some niches are more price-sensitive than others, tailor your discount accordingly.
Your growth stage or campaign goals: Are you just launching? Relaunching? Celebrating a milestone? Rewarding your superfans?
Your offer should match your current growth objective.
💡 Types of discounts you can offer
1. Seasonal Discounts
Seasonal discounts, like Black Friday, Christmas, or spring sales, can help establish a rhythm and predictability in your business. Some readers may even delay upgrading in anticipation of the next offer, which can drive spikes in revenue during key promotional periods.
2. Special Discounts
Special discounts are all about recognition and relationships; they’re not for everyone, but for your most loyal readers.
They’re personal and targeted. These offers are perfect for subscribers who regularly open your emails, reply to posts, or actively share your work. They’ve already shown they care, now show them you care back.
Apply “grandfather pricing”. Offering a discount between 50% and 80% off to this group isn’t about undercutting your value, it’s about giving back. This practice rewards early supporters with locked-in, lower rates.
Reach out directly. A personal email or message saying “Thanks for your support, here’s something just for you” can convert superfans quickly while strengthening the bond.
This kind of targeted generosity can push you past the 100 paid subscribers milestone, earning Substack’s white badge and the credibility that comes with it.
👉 Want to know how to identify and activate your superfans? Use my 5-step smart discount strategy to create your own high-converting loyalty campaign.
3. Celebration Discounts
Milestones are perfect moments to invite people in. Whether you're celebrating your newsletter anniversary, hitting 5,000 subscribers, or reaching 100 paid members, limited-time discounts tied to these wins make readers feel like they’re part of your journey.
Make your discounts actually work
Bec Evans and Chris Smith first tried to understand what value they could offer to their readers with consistent content and experimentation.
And they found that directly asking and layering in a discount resulted in a significant paid subscriber bump. Timing and communication made the discount effective.
“So, there is no one answer but a combination of consistently posting, running experiments with subscribers to see what works and offers good value.
Then what got us over the 100 was simply telling people and offering a discount. Had a rush of subs when we promoted.”
and ,
Couple your discount with an upcoming offering
Carolyn Yoo paired a discount with an upcoming value-packed event, giving readers a reason to act immediately. Bundling urgency and value can be a powerful conversion trigger.
“Combining a promotion for yearly subscriptions along with a tangible upcoming offering (in my case, a creative challenge with daily prompts) helped me reach 100 paid subscribers.”
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Russell Nohelty shares how he uses pledge drives to convert subscribers into paid members, offering them the flexibility to upgrade at an amount that feels right for them.
“The best driver is easily our “pledge drives”. Every quarter we have a pay-what-you-can-afford event where you can get discounts up to 80%. Every time I do one I get 100-200 new paid members. Then, we also do “flash sales” a couple of times, which are one-day events with steep, steep discounts down to $8/yr.
Since I have 46,000 subscribers, even if I only pick up 0.3% every time I host an event, that is significant. People try this same strategy with 500 subscribers, and it just isn’t worth the effort. Scale has its own leverage.”
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Amber Katz also offers occasional discounts and giveaways to keep her audience engaged and encourage them to upgrade to a paid subscription.
“I remind beauty industry people that a subscription is a business expense, I offer sales a few times a year and offer giveaways to free and paid subscribers, with paid subscribers getting 2 entries.”
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2. Promote yourself relentlessly
Turning your newsletter into a business? Then you need to act like one.
Self-promotion isn’t a luxury or something to be ashamed of; it’s a requirement for growth.
Why Self-Promotion Isn’t Optional
No one will promote your work unless you do first.
Expecting organic growth without making noise about your paid offering rarely works. Readers need clear, repeated invitations to support you.You can’t just drop a paywall and hope.
Announcing a paid tier without context usually leads to silence or minimal conversions. Your readers need to understand:What’s behind the paywall
Why it’s valuable
How they can support you
One tweet isn’t enough. One email isn’t enough.
Self-promotion is about showing up consistently, reinforcing your message over time. When people see your commitment, they’re more likely to invest in it.
It will feel awkward at first, but you should do it anyway. Most creators admit that promoting themselves isn’t comfortable. But those who push through see results. Visibility builds credibility.
3 Powerful Ways to Promote Your Newsletter
Here are 3 strategies to promote your newsletter content to expand your reach and convert free readers into paying members: