How to Start A Paid Newsletter

One of the most interesting trends I’ve seen over the past few years is the rise of paid newsletters. Every week, someone launches a new paid newsletter. And for good reason. It’s one of the most attractive models I’ve seen over my two decades of building and marketing internet products. Given the choice between blogging and starting a newsletter, I think the decision is pretty obvious.

Blogging requires driving traffic directly to your website. You have to fight with the algorithms on Facebook and Twitter to get eyes on your work, and the SEO algorithm on Google favors professional marketers rather than individual writers. Newsletters invert that equation, and create a one-on-one relationship between the writer and the reader, right through the inbox.

So what does a paid newsletter operation look like?

A typical model is beginning to emerge. Most major newsletters, such as Ben Thompsons’ Stratechery, and Bill Bishop’s Sinocism, follow a repeatable pattern. They write fairly long form editorials covering news events 4-5 days per week. Typically, one issue per week is free and publicly available as a way to acquire new readers. The rest lives behind a paywall. Here are some helpful trends.

• Monthly membership prices range from $3 per month to well over $100.
• Many paid newsletters offer discounts for paying for a year upfront.
• Some offer team-based pricing options, like Web Smith's team licenses for enterprise clients of 2PM.
• Some offer paid communities: a membership through Slack or Circle that allows readers to meet one another.
• Most paid newsletters (meaning newsletters that charge a subscription fee) do not also take ad sponsorships.

Sounds pretty straightforward, right? I’d be lying if I said there weren’t any downsides. Here are a few I’ve encountered so far:

• You have to actually write the thing. It’s a pretty large commitment to be writing 4 or 5 days a week, at a high enough quality to justify a monthly price tag.
• You have to find the time to do marketing. If you're charging a price for your writing, you are selling a product. You'll have to create a sales funnel, and find a way to drive attention to your work. Where will you find new readers? You can’t just wait for “if you build it, they will come”, because they won’t. I promise.
• You’ll need some tech chops to set up the platforms. Depending on the email platform you choose, and if you decide to build out a robust marketing strategy with a landing page, branded merchandise, and a referral program, you’ll need to worry about some back end infrastructure. Processing transactions, payment dunning, deliverability, email domain authentication, and more will become part of your toolkit.
• Your content is never really locked down to members only. Since you’re sending it in an email, it can be forwarded to anyone and everyone. Something to think about.
• You have to deal with churn. A certain amount of customers are going to kill their subscription and/or ask for a refund every month. It’s going to happen, no matter how hard you try for it not to. There’s real commitment required for fighting churn and keeping subscribers engaged and happy.

So where do you start?

The first step is to figure out what you want to write about. What drives you? What are you passionate about? More than that, what can you actually, realistically, write about day-in day-out, for years on end? Do you have a unique take on your local sports team? There’s probably a market for that. Have you been underemployed as a data analyst and have some interesting visualizations to share on particular industries? Yep, probably a market. Do you create the world's funniest hand-drawn cartoons? Definitely a market.

Once you nail down your topic, you’ll need to decide on a tech stack. There are about two dozen ways you can go here, but a common approach is the combination of WordPress (for a landing page and published blog posts) and a membership platform called Memberful (to gate certain content behind a paywall.) Memberful was acquired by Patreon and is widely in use for membership sites of all kinds. You’ll need to be able to restrict access to posts, sync your paid member status with your email delivery provider (I like Mailchimp for this), and handle payments / upgrades / refunds. For a lightweight option, Substack, Revue, and Ghost make it easy to start paid newsletters.

The best way to get started is to start subscribing to a few paid newsletters today. I think it’s a wise decision to get yourself very familiar with the model and the cadence of running a paid newsletter, and there’s no place better to start than by reading the work of other, proven writers.

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