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The great personal newsletter migration

CJ Chilvers
CJ Chilvers
2 min read

For the third week in a row, about a dozen of my favorite indie newsletters have landed in the spam folder — newsletters I’ve opened and click-through hundreds of times.

What gives?

I love how Apple, DuckDuckGo, Neeva, and others are making our online lives a little more private and secure. It was about time companies started seizing on that clear gap in the market. The downside for indie publishers was lower deliverability and engagement for email newsletters.

Traditional email service providers (ESP), who are responsible for delivering your favorite personal newsletters, have had the better part of a year to adapt to these privacy measures and offer solutions. But all I’ve heard is nonsense about how it’s not a big deal for overall delivery and “predictive AI” will justify keeping their current business model largely unchanged.

In my opinion, they’re failing, flailing, and (sometimes) straight-up lying to keep customers from fleeing.

That’s not what worries me. What worries me is how predictable it was. What worries me is how lame the response has been.

Check your calendars. WWDC is pretty damn close. Do you really think Apple is done releasing privacy features? Given Apple’s marketing successes around privacy, do you really think no one else is going to join them?

I’m being (indirectly) hurt by Apple here, and still cheering them on, because they’re doing the right thing. ESPs: this is the best you can do in response? Really?

Why on earth would a creator agree to a pay-per-reader email service when the service can’t reliably tell you if the readers are even real or alive anymore? Every week, those nonexistent readers pile up and drive down your real engagement in the eyes of Gmail (or insert your favorite email services/client). To the spam folder you go!

Here’s a hard truth for personal newsletters like mine: deliverability and engagement will keep declining. There’s no incentive (at the moment) to stop it. Every week, you’ll see more personal newsletters in your spam or promotions folders.

The pay-per-reader model is dead for traditional, personal newsletters.

The biggest business will always be OK. They’ll pay more and more to middlemen to ensure their sales promotions cut through to the inbox.

But the lowly, free, personal newsletter?

We’re faced with the decision to:

  • Pay increasing more for decreasing engagement.
  • Pay increasing more for decreasing engagement among free readers, while going freemium and charging enough to cover additional costs.
  • Use a free service like Substack or Revue and hope for the best.

So, now you know the reason all your favorite personal newsletters are going to Substack or Revue. No one I know is getting rich there, and it doesn’t mean they won’t end up in a spam folder. In fact, many still do. But, at least they’re not paying to be in a spam folder now.

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