Why You Should Start a Paid Newsletter


One of the most interesting trends I’ve seen over the past few years is the rise of paid newsletters.

Not nearly a week goes by that I don’t run across a new paid newsletter that people seem to be excited about and are keen to join.

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 used to be the old standby. If you liked to write and could finagle a website, you could develop an audience and probably figure out a way to make an income. It’s not that way anymore. Blogging is heavily saturated, and the SEO environment on Google is less than friendly to new startups.

I should know, I’ve spent the past 7 years in house at a major media company helping their brands stomp others without the advantage of trust and authority (and links) established over time periods measured in decades.

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. Normally one issue is made free and public, as a way to acquire new readers and let people see what they’re buying into.

  • Monthly membership prices range from $3 per month to well over $100.
  • Many offer discounts for paying for a year upfront.
  • Some offer team-based pricing options.
  • Some offer communities and additional private sections of their websites.
  • Topics range from startups and tech, to personal blogs, to treatises on China and economic analysis. There’s also a fast growing segment of sports related newsletters, too.
  • Most paid newsletters do not offer sponsors. I think that’s the right move, and I’ll go further into that in the future.

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 quality level high enough to justify a monthly price tag. That said, Conversion Gold (my newsletter) only publishes twice a month.
  • You have to find the time to market. This is true of all products, but paid newsletters are typically smaller headcount operations. So if it’s you doing the writing, you’re also probably the one doing the marketing. 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. I intend to do deep dives on exactly how to set up your technology, but suffice to say, it’s not as easy as registering for wordpress.com and picking a template. You’ll need to worry about processing transactions, payment dunning, deliverability, email domain authentication, etc on top of running the website.
  • Your content is never really locked down to members. Since you’re sending it in an email it can be forwarded to anyone and everyone. Yeah, some sites have begun sending links to password protected sections of the site, but I think that’s in poor form. It’s fine to link to the site too, and I do that, but always send the full text in the email.
  • 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 a very real industry (and commitment you have to make) for fighting churn and keeping subscribers engaged and happy.

I’m sure there are dozens more, both pros and cons, that I haven’t enumerated here. I just want to get your brain thinking in equal balance and evaluating the idea before you jump in head first.

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 worlds funniest hand drawn cartoons? Let me know, because I’d sign up in a heart beat.

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 my KISS approach has me building on WordPress and using a plugin/platform called Memberful. Memberful was recently acquired by Patreon and is widely in use for membership sites of all kinds. That’s what this is, after all, a membership site. 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.

I’m going to kick off a series of articles dedicated to showing you the ins and outs of each platform, very shortly.

For now though, I think the best thing that you could do is go subscribe to a couple. Substack is a great platform that has a ton of paid newsletters you can subscribe to right now. The great thing is that you can preview any of them before you buy. 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 with other, proven lists.

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