Newsletters Get Tricky

I tried my hand at writing a newsletter for about twelve months a few years ago. One thing I found disappointing was the level of engagement was so low. Of course, I knew that through analyzing my open rate and click rate. Although I felt like the newsletter was fairly high quality, and I liked the formula I used, I had a small list of subscribers, and the open rate rate wasn’t encouraging. I actually had two people who were subscribers to my newsletter if I had any recommendations for good music IRL. I pointed out that I sent them a newsletter that contained exactly what they were looking for every few weeks.

Though I lacked an engaged audience, one of my biggest frustrations in generating a newsletter was the extremely buggy TinyLetter service. When I started checking out Revue’s competing newsletter service, I found the product to be well designed, but I couldn’t imagine paying monthly to send a newsletter to a couple of handfuls of people (who didn’t seem to really be paying attention). Martin from Revue reached out a few times and asked me what I was looking for in the product and what it would take to convert me to a paying subscriber. I was honest with him about the lack of detectable interest in what I was sending and that it wouldn’t make sense for me to pay to for the service. He understood, and shortly later, I dropped the newsletter.

With Apple’s new privacy controls (only applied to the Apple mail products, of course), newsletter creators will be missing the kind of data that caused me to call it quits on writing mine. Owen Williams opens up about his concerns for writers in a piece for OneZero.

As a user, I like the idea of features like this that allow me to choose my privacy settings. As a creator, however, it’s increasingly difficult to ignore Apple moving toward a world where the only acceptable business model is the company’s: building apps that monetize through platforms owned by Apple.

Williams worries that asking users to pay for their media consumption via subscriptions is not one that can ultimately scale in the same way as advertising supported models. When he brings up the services that relied on advertising, he gets pushback.

Every time I write about these changes, people tell me that perhaps those things didn’t deserve to exist — because tracking is evil — but not everyone can afford to pay a mountain of monthly subscriptions for things.

I was surprised, when I made the same point about the scalability of the subscription model, that I received some level of pushback as well. I don’t think it’s a point worthy of contention, though. Not everyone can afford a bunch of fragmented subscriptions. Adam Tinworth also expresses his reservations about the new Apple Mail change and what it means for a key newsletter metric. I’m sure there are quite a few other writers who have put out similar pieces with identical sentiments. It’s easy to back Apple on the implementation of tougher privacy measures, until you step back and think about all of the implications.

Postscript: Robin Sloan’s way around the tracking pixels being blocked by Apple is to just use her email newsletter to link to content on the web.



Christianity as counterculture, minimalism, software, noise and paper airplane mechanics.

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Robert Rackley

Robert Rackley


Christianity as counterculture, minimalism, software, noise and paper airplane mechanics.