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We live in the era of Substack, where anyone and everyone is thinking about how to earn money from their email newsletter. And if you’re using Substack, you’ve certainly been encouraged to think about charging for your emails.

However, it’s challenging to publish an email newsletter that inspires people to pull out their wallet and start paying money to receive it. One of the hardest businesses to run, in fact, is a subscription business. There’s a lot of churn: people pay once, then drop off and never return.

The honest truth? Most writers shouldn’t charge for their email newsletter. It should be free because it’s one of the most valuable marketing tools that authors have. (More on that here.)

But if you want to monetize your email newsletter, keep reading.

Jane started her free newsletter, Electric Speed, in 2009. Today, it pulls in five figures in advertising every year. Her paid newsletter, The Bottom Line, is a six-figure newsletter with an 80% profit margin that’s been continuously published since 2015.

In this nuts-and-bolts business class, you’ll learn about the different styles of paid newsletter. One of the most important decisions you’ll make, early on, is whether to focus on a transactional model or a patronage model. Are people paying for the value you offer, or are they paying because they want to support your work? Sometimes it’s both, but you’ll want to think through the differences—because it affects your content strategy. You’ll learn about the types of newsletter content that people pay for, including how to balance free and premium content to reach readers and convert free readers into paying ones.

Marketing and promoting your newsletter is often a big question mark, especially for those who aren’t using Substack. This class will cover techniques to help readers discover your newsletter. We’ll also pay special attention to the landing page for your newsletter that compels people to sign up, as well as calls to action in the newsletter itself, to ask people to pay. Sometimes you can effectively monetize a newsletter simply by asking for a small tip rather than a subscription commitment.

This class will include many examples of successful newsletters that earn money and the strategies they employ to maintain and grow their subscriber base. These real-life examples will provide you with actionable insights and inspiration to apply to your own newsletter.

What you’ll learn in this class:

• The differences between a transactional model or patronage model, and how they blend at times
• What types of content work best for paid newsletters, with examples
• The varied types of pricing models and tiers
• Strategies for growing your email list organically (without paying)
• Various monetization methods beyond subscriptions, such as affiliate marketing, sponsorships/ads, and tip jars
• The basics of creating a sales funnel that guides free subscribers into becoming paying subscribers
• Real-life examples of successful paid newsletters and the strategies they use to maintain and grow their subscriber base

If you add in her time in corporate America, Jane has 20 years of experience in managing email newsletters, and it’s her preferred creative outlet. Take this class to learn about your potential for monetizing email, especially if you’re unsure whether it’s a fit for your work, to avoid wasted time and frustration.

Note about Substack: This class is meant for anyone wishing to earn a profit from their newsletter, whether they use Substack or not. While there will be many examples of Substack newsletters in this class, Jane herself does not use Substack for her professional, profitable newsletters. While this isn’t a class about Substack, there will be some Substack-specific tips for those on the platform.

Who should take this class

• Writers who have existing free newsletters. If you have a free newsletter and want to start earning from it, this class is perfect for you.
• Writers who offer paid newsletters with few paying subscribers. Maybe you’re asking for money, but no one is paying. There can be many reasons for that and we’ll cover them in this class.
• People new to email. If you want to build a paid newsletter from scratch, this class will help you avoid major pitfalls and get clear on your value proposition.
• Authors and bloggers. Writers looking to supplement their book sales or other income with a paid newsletter will find this class highly applicable to them.
• Freelancers and content creators. Anyone who regularly creates content and wants to explore additional revenue streams via email will learn foundational principles.

This class is not suited for

• People who don’t like or prefer email as a medium. Consistency and commitment is key to a successful newsletter. If you don’t enjoy writing regularly for your email newsletter, this might not be the right path for you. If you can’t even think of what to write in an email, this class may not help you. (This is a business class, not a writing class.)
• Anyone seeking to land a traditional publishing deal by building an email newsletter list. This class focuses on monetizing newsletters, but not through traditional publishing deals. We will not discuss how to attract or pitch agents/publishers/editors. We will look at the value of the email newsletter for its own sake, not as a path to some other goal.
• Anyone who prefers one-on-one coaching or consulting. This is a large group class (hundreds of writers) and can’t provide personalized attention, although your questions are welcome during Q&A time.

What you’ll receive

How do I attend the live class?

This class uses Zoom webinar technology (see system requirements). You will join through your Internet-connected computer or mobile device. When you register, you will receive information via email on how to join the class. If you don’t receive it within 1 hour of registering, please contact us.

• When: Wednesday, April 1, 2026
• Time: 1:00 p.m. – 2:30 p.m. EDT / 10:00 a.m. Pacific
• Fee: $25 through March 29, 2026 / $35 if you register after March 29, 2026

The webinar is broadcast via the internet with live audio delivered through your computer or mobile device speakers. The visual presentation is displayed directly from the presenter’s computer to your computer screen. The Q&A is managed through a chat-style submission system with questions read and answered by the presenter for the entire class to hear.

Closed captions are provided during the live class. We use Zoom’s automated closed caption service (powered by Otter), which is about 80%+ accurate. We also use Otter AI to generate an unedited transcript, provided with the recording.

Testimonials

Event Attendance & Anti-Harassment Policy

We strive to provide an environment where all present—whether attendee, presenter, or staff—can feel supported. In order to ensure a welcoming event, here is what we expect from all who participate.

• That the presenter and the presenter’s work be treated with respect by attendees and that all attendees treat each other with respect and a generosity of spirit.
• That attendees will refrain from harassment of any sort including (but not limited to) comments or questions of a racist, homophobic, sexist/sexual, or threatening nature. This includes actions that disrupt or interfere with anyone’s ability to participate. Offenders will be disconnected from the live event.