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👋 Meet the creator
is a longtime writer and digital creator, best known for his content across Medium and now Substack.
After years of writing online and building a loyal following, Tom launched his Substack, , where he teaches creators how to build long-term writing careers.
With over 240 paid subscribers and more than 18,000 total readers, Tom combines writing, marketing, community-building strategies, and a smart use of AI tools to stay ahead of the curve.
If you're looking for a creator who builds scalable systems around quality content and a strong marketing mindset, this interview is a must-read.
🥁 How it all started before Substack
Tom’s writing journey began on Medium, where he became a top writer. He published hundreds of articles and built a loyal audience of over 62,000 followers.
He also ran a YouTube channel focused on vlogging.
He experimented with various digital products, like courses and coaching programs, and built multiple income streams around his content.
After years of being online on different platforms, Tom got a clear vision in 2023: he wanted more control, better community interaction, and direct access to his audience, so he transitioned to Substack.
📌 How he started on Substack
He joined Substack in May 2023 after being attracted to Substack’s community-first approach and flexible format.
He then realized Substack’s real potential: the ability to engage deeply with an audience, own his email list, and create a sustainable writing business.
“The pros of Substack are
Email subscribers, you get to talk to them whenever you want.
You also have this amazing Notes platform where you can write short form content.”
— Tom Kuegler, The Writing Long Game
🚀 His key steps to use Notes for growth
Tom is a power user of Substack Notes, and his strategy is both intentional and consistent:
Post often, in different formats: Lessons, questions, updates, promotions.
Engage generously: He comments on others’ Notes to build visibility and community.
Repurpose smartly: Turns newsletter content into bite-sized Notes to spark reactions and shares.
Notes became a powerful growth engine for him, consistently driving both free and paid subscribers.
“One of my favorite features is: you go to a Note that is done pretty decently, click into it, scroll down, and you can see related Notes.
That introduces you to so many kinds of viral-ish Notes that are doing well.”
— Tom Kuegler, The Writing Long Game
⭐ How he leverages AI tools to create content and analyze metrics
This was a standout part of the conversation. Tom integrates AI deeply into his workflow:
Notes generation: He trained an AI model to match his tone and style for writing Notes.
Business Analysis: He spent four hours compiling an executive summary of his newsletter and had Claude analyze it for insights.
One comment from this business analysis made by AI changed how he approached his writing:
“One of the things that AI told me was:
‘You keep making stuff because you want to make it and not because your audience wants it.’
And that hurt because I really trust myself when I write my content.
But, I have to listen to my audience a little bit more and make sure that it's more in line with what they want rather than what I think that they want.”
Tom Kuegler, The Writing Long Game
He emphasizes that AI doesn’t replace creativity, but rather accelerates it.
💸 His paid subscription strategies
It took Tom nearly a year to figure out what paid subscribers really wanted.
He initially offered Notes training, but things clicked when he invited subscribers to submit their Notes for feedback. That’s when he saw the most excitement.
So he built Notesmith, an AI version of himself that:
Gives feedback on Notes
Rewrites them to improve clarity and tone
“One lady wrote a 14,000-like Note with my Notesmith tool.
I won’t take full credit, but it helped her polish, edit, and tighten it up.”
— Tom Kuegler, The Writing Long Game
Retention has grown since launching Notesmith. It’s now a core value offering for paid members, and Tom continues adding more tools to keep the value fresh.
🗂 Why he stopped using paywalls, and what he does instead
Tom no longer locks most of his content behind paywalls.
“Paid subscriptions aren’t the best way to monetize.
Creating online programs and courses is better because you can earn more at once instead of grinding for $10. It’s a lot of effort for little return.
I’m going to start making more high-ticket programs and courses.”
— Tom Kuegler, The Writing Long Game
Instead of gating content, he upsells value through tools, community, and eventually, digital products.
📚 In this interview, we also talked about:
His learnings from running monthly discounts
How he shaped his paid subscription offers
Building a Slack community for his paid members
How he engages with readers
Why he doesn’t use Substack Chat
And more…
🎥 Watch the full live interview to learn exactly how Tom Kuegler built The Writing Long Game on Substack.
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Thanks for reading, and feel free to reply if you’d like to connect!
See you next week.
Ciler
Find me on Substack Notes & LinkedIn
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