Put Your Million Dollar Newsletter on Autopilot

Put Your Million Dollar Newsletter on Autopilot
Photo by Oskar Kadaksoo / Unsplash

Look, you get it. Newsletters matter. They always have, but they’re having even more of a moment now.

But one of the biggest (perceived) problems with newsletters is their fleeting nature. Write a newsletter today, send it to your subscribers... then what? It’s often lost to the email archive.

I hate that for you. I want your great work to pay off (literally) for years to come. So in this short guide I'll outline the key steps to put your million dollar newsletter on autopilot. Make sure you watch the video below, because I want to show you how to do the thing instead of writing a list of steps to follow.

1 — Organize your newsletter by topic

For example, Million Dollar Newsletter talks about content, monetization, and growth. Every newsletter is connected to one of those topics. Not only does this make it easier to write, but it helps me build topical deep dives.

2 — Create topical deep dives

Use your best newsletters to create evergreen sequences in your ESP (I use ConvertKit). For example, my “old” productivity content is running on auto-pilot as 5 day email courses on planning, time management, and more.

3 — Automate entry points

People can self-select entry on an email signup page, or be added directly using a link trigger in ConvertKit. For example, if I have a newsletter about creating newsletter content, I can offer the reader a free 5 day series on how to plan, write, and deliver newsletter content that converts.

4 — Sell topical workshops and products

At the end of these deep dives, offer a recorded workshop or relevant product to the content. At the end of my productivity sequences I offer my Most Productive Week Ever mini-course. At the end of my creator series I pitch the $1K Course Blueprint.

5 — Refresh 1-2x per year

As you continue to write more content—and learn even more yourself—keep updating the content, the pitches, and deliver the best experience for your readers. Consider a live cohort course or reaching out to customers to offer coaching.

Using a simple flywheel like this with a tool like ConvertKit means your helpful content keeps providing value for readers and paying dividends (literally) for you. I’ve been fortunate to set up these flywheels for many creators and entrepreneurs the past 8 years. Check out the video below to see a step-by-step guide to building an automatic email machine to deliver content and print money.

Chapters (watch on Loom)

00:00 — Introduction and Overview
00:44 — Organizing Content and Creating Deep Dives
02:41 — Setting Up Automations and Tags
05:12 — Starting the Deep Dive Automation
06:27 — Connecting Sequences and Adding New Emails
08:18 — Building Evergreen Content Topics and Pitches
10:17 — Customizing Email Content and Adding Sales Pitch
14:37 — The Key Takeaways  and Next Steps