How to Build a Successful Subscription-Based Newsletter Startup

Should you build from scratch or go with a newsletter-business-in-a-box?

Look, there aren’t any get-rich-quick secrets in this post. I actually never meant to build a business around a subscription-based newsletter. It happened kind of accidentally.

But because that business (TeachingStartup.com) took off, I get a lot of questions about how to make a subscription-based newsletter successful. I’m not kidding myself; I know the demand for my knowledge in this arena has little to do with me and much more to do with the recent success of newsletter-business-in-a-box companies like Substack and Revue.

There’s definitely money in newsletters if you do them right.

But I’m also not kidding myself in thinking I have the secret formula for newsletter success. Like I said, I never meant to build a newsletter business. But in a weird, kind-of-backwards way, I think I can tell you exactly how to build a better newsletter — either as a standalone product or as part of a marketing campaign — by telling you why I set out not to build one.

Why Newsletters Are All the Rage

Yeah. Why now? Email marketing has been around for decades, and email marketing platforms have been around almost as long. And what’s more, it’s not like they’ve been skulking in the shadows, waiting for their moment.

For example, not one, but two entrepreneur friends of mine sold their platforms in 2012 (iContact) and 2015 (Bronto). Both of those were awesome exits, but to be fair, not quite the $12 billion that MailChimp just sold for a couple months ago.

Despite what some other opportunistic messaging startups might tell you (looking at you, Slack), email is not going away anytime soon.

The current newsletter trend has less to do with MailChimp and more to do with podcasts. Or better yet, it’s more like the Medium written-word version of YouTube, Twitch, and Patreon. There are dozens of newsletter-business-in-a-box companies now, platforms that will take care of all of the business for you — leaving you free to get creative and write words that are worth paying for.