6 Step Checklist To Build A $100,000+ Paid Newsletter in 2025

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In this video, I share my proven 6-step framework for building a $100,000+ paid newsletter on Substack, the same approach I used to grow Category Pirates and Write With AI into 6-figure newsletters. This walkthrough covers key strategies like harnessing a traffic engine, making your newsletter topics tangible, and leveraging Substack's unique free-to-paid model to maximize reader engagement and conversions. And at the end, I confront the most common questions and faulty beliefs I hear about starting a paid newsletters. If you're a writer, business owner, or complete beginner aiming to generate substantial recurring revenue and build a long-term audience, this checklist will help you structure, scale, and monetize your newsletter effectively on Substack and beyond.

00:00 Step 1: Pick a topic attached to a traffic engine
01:34 Step 2: Make your newsletter tangible
06:29 Step 3: The “One Free, One Paid” Strategy
09:10 Step 4: Send paid snippets to your entire free list
11:12 Step 5: Put the paywall preview at a cliffhanger
12:27 Step 6: Leverage Substack notes
13:35 Q: How long should a newsletter be? Do you start charging immediately? Does anyone use email anymore?
15:07 Q: Subscribers, Open Rate, and CTR - how do you improve these metrics?
16:33 Q: How do you continuously provide high-value content to maintain a long-term audience?
18:12 Q: What if I’m too young/old and have no prior experience?

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