🎉 What Publishing 100 Newsletters Taught Me

Good morning. Today is a BIG day.

I DID IT. I’ve written and published 100 newsletters. 🥳

That was my one target when I started this newsletter. It wasn’t subscribers, open rate, or ad revenue.

The goal was to start. Then, over time, I wanted to create something helpful for entrepreneurs like myself, become a better writer, establish a sustainable workflow, and publish one hundred newsletters over two years.

Thank you for reading and your support. No one succeeds alone, and everything is better with friends. 🤝

It’s been quite the journey, and today I’m sharing what I learned along the way.

Let’s get into it.

— Gordon

Together with beehiiv 🐝

Today, beehiiv is going to share the biggest news and updates in company history, live during its first-ever Winter Release Event.

It’s a virtual livestream event, and I’d love for you to join me there.

I’ve been obsessed with beehiiv since I launched my newsletter on the platform over two years ago. beehiiv has spent the last four years reimagining how creators build online, and now they’re unveiling what comes next.

When: Thursday, November 13th, 1-2 PM EST

How: RSVP here 👈

🎉 What Publishing 100 Newsletters Taught Me

One hundred newsletters. Thirty months. Zero regrets.

Not consecutively. Not perfectly.

But consistently enough to reshape how I think, create, and build.

During that time, I've evolved from a generalist writer to someone who thinks in content systems, rather than motivation.

It didn't happen overnight. That’s for sure.

It happened one issue, one insight, one iteration at a time.

You don't need a viral post to change your business. You need a consistent practice that changes you.

When I started, I believed consistency just meant showing up every week, no matter what.

I learned that it’s more about building the systems that make showing up easier.

The first issue in May 2023 was an experiment.

I wanted to create. To Build. And, to get out of my own way.

The first issue wasn't polished or strategic, but it set a precedent that matters more than perfection ever could. I just started.

Publish, learn, repeat. That was it from there.

By fall 2024, I'd hit a wall. Motivation and inspiration were no longer enough.

I began building a system to make my process sustainable.

I built repeatable workflows, an idea sourcing system, and wrote seven custom AI prompts, working diligently to remove friction from idea to publication.

The less I relied on inspiration striking, the more I could depend on momentum.

That shift from art to architecture became the foundation of my work today.

By the beginning of 2025, the systems clicked.

I carved out a niche that felt less general and more aligned with who I was and what I did every day.

The time I spent on each newsletter decreased from 20 hours to under 4 hours.

The pressure of publishing each week disappeared, and creativity had room to return. For the first time in two years, I felt ahead instead of behind.

I’ve now published thirty-two weeks in a row.

Not because I was grinding. Because the system made it effortless.

The first 100 issues taught me how to publish.

The next 100 will focus on refinement and reach (distribution).

Content is a quality AND volume game.

You can't learn what quality is until you start publishing. You can't publish high-quality content in large volumes without building effective systems.

Five systems turned publishing from a struggle into a rhythm.

HERE’S HOW:

• Build Systems That Remove Friction

• Turn Publishing Into Proof

• Focus on Creating Momentum

• Repurpose with Intention

• Track the Right Metrics

Systems don't replace creativity. They protect it. Start here.

Build Systems That Remove Friction

Everything changed for me in spring 2025.

I stopped relying on motivation and designed systems that made publishing effortless.

Each system you build is a safeguard for your creative energy. You'll stop asking what to do next and have a clear roadmap for creating.

Start simple. Create a three-part outline template:

1. Problem (Hook/Who are you talking to and why should I care?)

2. Solution (Benefit to solving the problem/What’s In It For Me?)

3. Action Steps (How to solve the problem)

Then, reuse it for every piece of content you post.

Consistency starts when systems take over where willpower ends.

Turn Publishing Into Proof

That first issue taught me a crucial lesson.

Every published post is data, not judgment.

Instead of aiming for perfection, use publishing to test ideas and collect signals. Those signals reveal what resonates and what deserves repetition.

You build credibility by showing your work in public, week after week.

Watch for patterns. When three clients ask about the same topic, that's your next post.

The best feedback isn't comments. It's the patterns you spot across 10 posts.

Focus on Creating Momentum

When you build a content flywheel, everything compounds.

Build your flywheel. It should flow in one direction to start.

Your newsletter is your script for YouTube. Then your YouTube videos become short-form social posts (Reels).

In reverse, your short-form drives long-form content by rapidly testing ideas to learn which ones you should expand on.

Scattered energy produces scattered results, and you get nowhere. But a flywheel creates momentum.

It's the difference between posting everywhere and building somewhere.

Your content becomes a system, not a scramble.

Repurpose with Intention

Repurposing isn't about volume. It's about leverage.

Each piece of long-form content can create a dozen new touchpoints if planned correctly. Start with one idea, then remix it into different formats with a purpose.

You'll expand reach without increasing effort.

Smart creators don't create more. They multiply what already works.

Track the Right Metrics

Track your inputs, not your outputs.

Inputs are what you control.

Idea capture, publishing cadence, and time invested.

Outputs (views, likes, shares) will follow.

Track two things weekly. Posts published and time spent.

Once you're consistent, add one output metric. Which topics get the most engagement.

Vanity metrics are distractions.

Creating quality content consistently will make growth inevitable.

Focus on what you can control, and the rest takes care of itself.

Thirty months in, 32 weeks straight. Now the system scales the streak.

That first issue was an experiment. This one is proof.

The mechanics of posting consistency are learnable.

Systems make showing up easier, clarity makes every decision simpler, and momentum builds when you trust the process.

Thanks again for reading. See you next week.

ONWARD TOGETHER.

Everyday Insights 👀
This week’s recommended reads

🧠 The Hidden Beliefs That Hold Leaders Back
Even experienced leaders can sabotage progress by clinging to outdated beliefs. A reminder that mindset work isn’t seasonal—it’s systems work too.

🤖 Emplifi: State of Social Media Marketing 2026
AI and UGC are officially converging. This new report shows how marketers are reallocating budgets toward faster, personalized content pipelines—a preview of how automation is changing the creative stack.

📊 Instagram Adds Competitor Insights for Professional Accounts
Instagram just rolled out built-in competitor tracking. It’s one more sign that the platform is shifting from creator-first to operator-first—rewarding those who treat content like a business, not a hobby.

The Armory 🧰
Tools to sharpen your edge

When you’re running a business, it's easy to get distracted by shiny objects.

More often than not, you don't need much of a tech stack in the beginning.

As your business grows, you look for ways to leverage your time. Technology is a great place to start before your first hire.

Here is my personal tech stack:

• vidIQ*—The insights and coaching video creators need to grow

• Loom—The easiest screen recorder you’ll ever use

• Canva—Makes it easy to create professional designs

• beehiiv*—The Newsletter Platform Built for Growth

• Calendly—Takes the work out of scheduling so you can accomplish more

• LastPass—Safely store and autofill passwords across devices

• Hypefury*—Your personal assistant to grow your 𝕏 (Twitter) audience

• Testimonial*—Get testimonials from your customers with ease

• ChatGPT Plus—Your personal AI assistant to be more productive

• Hemingway App—The Hemingway App makes your writing bold and clear

• Google Workspace*—Manage your emails, docs, sheets, tasks, and schedule in one place

• QuickBooks Online—QuickBooks makes online accounting easy

• Adobe Creative Cloud—Design with confidence to tell your brand's story

My Favorite Things 💙
What I’m reading, watching, and enjoying

This week, I finished reading The Lean Startup and re-read The Alchemist.

Here are my takeaways from each:

📘 The Lean Startup — by Eric Ries

Execution without learning is just motion. Ries’ framework reminded me that iteration is the real driver of innovation. The faster you can test, measure, and adapt, the more your business evolves toward something that actually works. Systems make experimentation sustainable, and that’s the foundation of compounding progress.

📗 The Alchemist — by Paulo Coelho

The journey is the reward. Coelho’s story hits harder the second time because it mirrors what creating every week feels like. Long stretches of uncertainty, small moments of clarity, and an ultimate reminder that everything you’re searching for is built through persistence. The treasure is in the process.