I Talked to 21 Substack Bestsellers. Here's the 7 Things They Do Differently.

The strategies nobody talks about that helped them build Substack Bestsellers (even if they started from zero)

I stared at my Substack dashboard, that familiar knot in my stomach.

Another month of publishing consistently. Another month of "doing everything right." Yet that coveted red checkmark – the sign of a Substack Bestseller – felt further away than ever.

Maybe you can relate?

You're showing up every week. Writing valuable content. Growing your subscriber count. But when you look at those red-checkmark newsletters, something feels... different about what they're doing.

The pressure builds because everywhere you look, the advice seems to be the same:

• "Just write great content, subscribers will come…"

• "Post consistently and show up everyday…"

• "Engage with your audience, reply to every comment…"

Yet something's missing. Because let's be honest – if it were that simple, wouldn't every consistent writer have a red checkmark by now?

Here's what makes this really frustrating...

While you're trying to figure it out alone, Bestsellers seem to be operating on a completely different level:

• They're charging premium prices (and people happily pay)

• Their posts consistently go viral

• Their free-to-paid conversion rates are impressive

• Their communities are thriving

Meanwhile, you're left wondering: What do they know that I don't?

I had to find out.

So, I decided to do something about it. I reached out to 21 Substack Bestsellers – writers who've built growing newsletters and earned that red checkmark (meaning 100+ paid subscribers) – and asked if they’d share their strategy.

What I discovered was really valuable.

These writers aren’t just "posting consistently" or "writing great content." They’re operating with a completely different playbook – one that most writers don't even know exists.

Some of what they shared contradicted everything I thought I knew about growing a newsletter. Other insights were so counterintuitive, I had to verify them with multiple writers to believe it.

But here's what really surprised me:

The gap between regular writers and “bestsellers” isn't talent. It's not luck. And it's definitely not some secret hack.

It's seven specific strategies that, when implemented correctly, dramatically accelerate newsletter growth.

In this post, I'm sharing everything I learned. Some of these insights might challenge what you believe about growing a newsletter. Others might completely change how you approach your writing business.

But before we dive in, a quick disclaimer:

This isn't theory. These aren't "tips and tricks." These are battle-tested strategies from writers who've built six-figure newsletters and earned that red checkmark you see next to their name.

Let's dive into what Bestsellers do differently...

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1. They Don't Focus on Paid Subscriptions First

This one surprised me the most.

When I asked these Bestsellers about their early monetization strategy, I expected to hear about optimal pricing tiers and conversion tactics.

Instead, I heard something completely different.

"I waited 8 months before turning on paid subscriptions," one writer told me. "By then, I had 5,000 free subscribers who trusted me completely. Converting them to paid was almost effortless."

Another shared: "Everyone rushes to monetize. I spent 6 months just proving my value. When I finally opened paid subscriptions, I had 100 people sign up in the first month. That made me a Bestseller"

Here's what Bestsellers understand that most writers miss:

Trust comes before transactions.

While most writers are trying to convert subscribers to paid from day one, Bestsellers focus on something much more valuable: building an audience that trusts them completely.

How do they do this?

Instead of holding their best content behind a paywall, they:

• Give away their most valuable insights for free

• Share vulnerable behind-the-scenes stories

• Respond thoughtfully to every comment

• Create valuable free resources and build a community first

"The bigger your free audience, the easier monetization becomes," explained a Bestseller with over 500 paid subscribers. "Each new paid feature or product launches to a bigger pool of warm leads."

The numbers back this up:

• Bestsellers average 6-8 months of free content before launching paid subscriptions

• Their free-to-paid conversion rates are typically around 5-6% (compared to the 1-2% most writers see)

• 80% of their paid subscribers come from their free list, not direct paid conversions

But here's what makes this really powerful...

While most writers struggle to convince cold audiences to pay, Bestsellers build armies of subscribers who actively want to give them money.

One writer put it perfectly: "By the time I launched paid subscriptions, my readers were asking me how they could pay me. The sale was already made."

This shift in thinking changes everything about how you approach your newsletter growth.

Instead of asking "How can I get people to pay?" start asking "How can I become indispensable to my readers?"

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2. They Write "Hero Posts" Monthly

Every Bestseller I talked to mentioned the same strategy: creating what they call "hero posts."

These aren't your regular newsletter updates. They're comprehensive, value-packed posts designed specifically to go viral and attract new subscribers.

"One good pillar post can bring in more subscribers than 20 regular posts," a Bestseller with 500+ paid subscribers told me. "But most writers never create them because they take more work."

What exactly is a pillar post?

Think of it like this: While regular posts inform your readers, pillar posts transform them. They're the posts people bookmark, share, and reference months later.

Here's what makes them different:

Unique Research

Best Sellers don't just share opinions. They:

• Interview industry experts

• Analyze real data

• Share specific case studies

• Document proven frameworks

One writer gained over 500+ new subscribers from a single pillar post where he analyzed 100 newsletter homepages and shared the patterns he found.

Actionable Value

Every pillar post follows this formula:

• Big promise in the headline

• Immediate hook that builds credibility

• Specific examples and proof

• Step-by-step implementation guide

• Clear results readers can expect

"The key is making it so valuable that not sharing it feels selfish," explained a Bestseller who grew to 10,000+ subscribers primarily through pillar posts.

Strategic Timing

Most writers post randomly. Bestsellers plan their pillar posts weeks in advance, timing them for:

• Major industry events

• Seasonal opportunities

• Market shifts

• Common pain points

They also promote these posts differently. Instead of just hitting publish and hoping for the best, they:

• Pre-promote to their audience

• Coordinate with other writers

• Plan social sharing campaigns

• Follow up with related content

The results? Their pillar posts consistently:

• Get 5-10x more views than regular posts

• Drive 3x more subscriber signups

• Generate months of steady traffic

• Become go-to resources in their niche

"Regular posts maintain your audience," one Bestseller explained. "Pillar posts grow it."

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3. They Use Notes Strategically (Not Randomly)

"Notes isn't social media – it's a growth engine."

This quote came from a Bestseller who gains 30-50 new subscribers daily just from Notes. Not by posting randomly, but by following a specific strategy most writers completely miss.

Here's what I discovered when I analyzed their Notes patterns:

They Post with Purpose

While most writers treat Notes like Twitter, Best Sellers use a strategic mix of three post types:

Educational Notes

"Share one insight that makes people stop scrolling," one Bestseller told me. "Make it so valuable they have to save it."

These posts consistently get the most Restacks because readers want to bookmark them for later.

Community Builders

"Every Friday, I start a thread asking writers to share their newsletters," another Bestseller explained. "It's not about promoting myself – it's about creating opportunities for others."

These threads often generate 100+ comments and expose their newsletter to entirely new audiences.

Behind-the-Scenes Stories

"Vulnerability attracts vulnerability," shared a Bestseller who grew from zero to Bestseller status in 4 months. "When you share real struggles and wins, people connect with your journey."

The Engagement Framework

They don't just post and ghost. Best Sellers:

• Respond to every comment in the first hour

• Join Notes Boost sessions strategically

• Support other writers consistently

• Build genuine relationships

One writer shared his exact numbers:

• 2 strategic Notes per day

• 30 minutes of engagement

• 15-20 new subscribers daily

• 300-400+ subscribers monthly just from Notes

"Notes isn't about quantity," he explained. "It's about showing up strategically and consistently."

But perhaps most importantly...

Bestsellers use Notes as a testing ground. They float ideas, gauge interest, and refine their message before investing time in full posts.

"If a Note resonates, it becomes a newsletter post," one writer shared. "If it really resonates, it becomes a pillar post."

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4. They Build "Content Ecosystems"

This insight hit me hard because it exposed a massive mistake most newsletter writers make.

While everyone else treats their newsletter as their only product, Bestsellers think bigger. They're not building newsletters – they're building content ecosystems.

"My newsletter isn't my business," one Bestseller told me. "It's the engine that powers my business."

Here's what that means...

Instead of just writing weekly posts, Bestsellers create content that:

• Feeds into multiple revenue streams

• Serves different learning styles

• Reaches readers where they are

• Compounds in value over time

Let me show you exactly how they do it:

Newsletter Content Gets Transformed

They take their best-performing posts and turn them into:

• Downloadable guides

• Templates & frameworks

• Video tutorials

• Live workshops

• Digital products

"Every piece of content should have multiple lives," explained a Bestseller who generates $10K monthly. "I can turn one great post into five different products."

They Use Chat Strategically

While most writers ignore Chat or use it randomly, Best Sellers use it to:

• Host weekly office hours

• Run paid workshops

• Create exclusive spaces for subscribers

• Test new content ideas

One writer shared how she uses Chat to validate new products: "If a topic generates huge discussion in Chat, I know it's worth creating a paid product around it."

The Community Connection

But here's what really sets them apart – they build communities around their content:

• Private groups for paid subscribers

• Mastermind programs

• Cohort-based courses

• Live events and workshops

"The newsletter brings people in," one Bestseller explained. "The ecosystem keeps them engaged and buying."

The Revenue Impact

The numbers are staggering:

• 70% of Best Sellers have 3+ revenue streams

• Their average subscriber value is 5x higher

• Product launches convert at 3x the normal rate

• Their business grows even when they take breaks

"The newsletter itself isn't even my biggest revenue source," he shared. "But it makes everything else possible."

This ecosystem approach changes everything about how your newsletter business grows. Instead of relying solely on subscription revenue, you're building multiple paths to profitability.

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5. They Market Through Teaching

"Stop trying to promote your newsletter. Start teaching everything you know."

…and start building in public. Many of these Bestsellers share what they’re learning in real time; the wins & losses, the good & the bad.

This insight came from a Bestseller who grew to 500+ paid subscribers without spending a dollar on marketing. His secret? He turned every piece of content into a micro-teaching moment.

While most writers just share information, Bestsellers structure their content like teachers:

They Break Down Complex Topics

"I document everything I learn…Every mistake, every success, every insight becomes a lesson for my readers."

Look at their most successful posts and you'll notice a pattern:

• Clear step-by-step breakdowns

• Real examples from their experience

• Common pitfalls to avoid

• Specific action steps to take

One writer grew his subscriber base from 500 to 3,000 in three months just by documenting his own newsletter growth journey.

They Share Their Frameworks

Instead of vague advice, Bestsellers create:

• Named frameworks that readers can follow

• Specific processes they've tested

• Systems they've developed

• Templates they actually use

"When you name your frameworks, people remember them," explained a Best Seller who consistently converts 5-6% of free subscribers to paid. "They share them. They become part of people's vocabulary."

They Show Their Work

But here's what really sets them apart – they don't just share results, they share the entire journey:

• Screenshots of their early failures

• Raw numbers from their experiments

• Behind-the-scenes decisions

• Honest reflections on what worked (and didn't)

One writer told me: "Every mistake I make becomes content that helps others avoid the same pitfall."

The Teaching Mindset

This approach changes everything about how they create content:

• Regular posts become case studies

• Updates become learning opportunities

• Wins and losses become lessons

• Comments become classroom discussions

"When you teach instead of tell, people don't just read – they implement," shared a Bestseller who maintains an 85% retention rate on paid subscriptions. "And when they implement and succeed, they become subscribers for life."

The results speak for themselves:

• Higher engagement rates

• More shares and recommendations

• Stronger community building

• Easier sales conversations

As one Bestseller put it: "Teaching isn't just how we deliver value – it's how we market. Every lesson builds trust. Every framework proves expertise. Every breakdown shows mastery."

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6. They Format Posts for Maximum Impact

"The biggest mistake newsletter writers make? They focus on what they write, not how they write it."

While most writers just dump their thoughts onto the page, Bestsellers think deeply about how readers will consume their content.

When I studied their most successful posts, I noticed a fascinating pattern in how they structure their writing. Every post follows a specific visual journey designed to keep readers engaged.

The Hook Pattern

Every high-performing post starts with one of these proven openers:

• A personal story that builds connection

• A specific problem readers face

• A surprising insight or statistic

• A promise of transformation

"Your first three lines determine if someone reads the rest," explained a Bestseller with over 800+ paid subscribers. "I spend 30% of my writing time on just the opening."

The visual flow is where things get interesting. Instead of dense paragraphs that tire the eyes, they create a visual journey through their ideas. They use short, punchy paragraphs mixed with strategic white space. Key insights get highlighted in bold, making important points impossible to miss.

One writer shared his exact process: "I write the post, then spend an hour making it visually appealing. Design isn't just about looks – it's about making ideas stick."

But here's what really sets them apart – they weave proof throughout their posts:

• Screenshots of real results

• Specific numbers and data

• Direct quotes from experts

• Before/after examples

Content Patterns That Convert

They use specific content structures that consistently drive engagement. Each type serves a different purpose:

• Case studies show transformation

• Framework breakdowns simplify complex ideas

• Step-by-step guides ensure implementation

• Myth-busting posts challenge assumptions

A Bestseller who averages a 40% open rate explained: "These aren't just formats – they're psychological triggers that keep readers engaged."

The numbers tell the story. Well-formatted posts consistently outperform traditionally written ones: 3x more shares, 2x more comments, 4x higher save rates, 5x better conversion to paid.

"Most writers think formatting is about making posts pretty," shared a Bestseller with 1,500 paid subscribers. "It's actually about making ideas impossible to ignore."

This attention to structure doesn't just make posts more readable – it makes them more shareable, more memorable, and more likely to convert readers into loyal subscribers.

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7. They Build Reader Relationships Differently

"Everyone talks about growing their list. Nobody talks about growing relationships with the readers already on it."

While most writers focus on getting more subscribers, Bestsellers focus on deepening connections with existing ones.

The difference is subtle but profound.

Most writers treat their readers like numbers on a dashboard. Bestsellers treat them like partners in a journey. This shift changes everything about how they approach their newsletter.

"The moment I stopped trying to grow my list and started trying to change my readers' lives, everything transformed," explained a Bestseller.

Here's how they build these deeper connections:

They Create Moments of Recognition

Every post includes examples and scenarios that make readers think, "That's exactly what I'm going through." They share vulnerable stories about their own struggles and victories, making their journey relatable and real.

The Comment Section Strategy

While most writers see comments as vanity metrics, Bestsellers use them to create meaningful discussions:

• They ask specific questions that encourage detailed responses

• They reply with thoughtful, personalized insights

• They highlight reader experiences and wisdom

• They create conversations between readers

"The magic happens in the comments," one Bestseller told me. "That's where community really builds."

Personal Touchpoints Matter

These writers find ways to make readers feel seen:

• They reference reader questions in their posts

• They celebrate subscriber wins publicly

• They create content based on reader challenges

• They remember details about their subscribers' journeys

One Bestseller shared his strategy: "I keep notes about my most engaged readers - their goals, challenges, and wins. When I can reference these in my writing, it shows I'm paying attention."

But here's what really sets them apart...

They turn readers into protagonists of their newsletter's story. They feature subscriber case studies, share reader insights, and create opportunities for their community to shine.

"My most popular posts are often the ones where I step back and let my readers' experiences take center stage," explained a Bestseller who grew to 400+ paid subscribers in eight months.

The results speak volumes:

• Higher engagement rates

• Stronger community bonds

• More word-of-mouth growth

• Better retention rates

As one Bestseller put it: "Growing a newsletter isn't about writing better posts. It's about making your readers feel like they're part of something bigger than themselves."

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Putting It All Together: Your Path to Bestseller Status

By now, you can see that becoming a Substack Bestseller isn't about luck or talent. It's about implementing specific strategies that most writers never discover.

Let's recap what sets Bestsellers apart:

• They focus on trust before transactions

• They create strategic pillar posts monthly

• They use Notes as a growth engine

• They market through teaching

• They format posts for maximum impact

• They build deeper reader relationships

But here's the thing...

Knowing these strategies is one thing. Implementing them correctly is another entirely.

Here’s the one thing I learned after speaking with these very open and welcoming Bestsellers:

You can do it. Becoming a Bestseller doesn’t need to be some far off dream. The opportunity with Substack is wide-open. It’s simply up to you to decide you will grow your newsletter to Bestseller status and don’t give up.

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Your Next Steps: Join the Substack Growth Class

If you're feeling overwhelmed by all these options, I get it. I've been there. That's exactly why I created my Six-Figure Substack Growth Masterclass where I walk you through:

• Exactly how I grew from Zero to 4,600 subscribers in 6 months

• How to find audience problems and create solutions to solve them

• My proven templates for offering services and products

• Step-by-step implementation plans

Join hundreds of other newsletter writers who are already using these strategies to build profitable newsletters. If you’re ready to finally start growing (and monetizing) your audience this year, click the button below and join us inside the masterclass:

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Remember: Every Bestseller started exactly where you are right now. The only difference is they discovered these strategies sooner and didn’t give up.

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Question - Which of these 7 strategies surprised you most? Which one will you start implementing first? Let’s talk about it in the comments. 💡

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📌 PS - If you found this post helpful, would you please consider restacking it and sharing it with your audience?

This spreads the word and keeps me writing content that will help you grow your Substack and “escape the cubicle” life. 🙏