It’s not the least bit surprising, I did find it a little interesting that three media-heavy newsletters — Study Hall, Today in Tabs, and Deez Links — are running a home-grown classified ad system in their newsletters. The latter two are hosted on Substack, which seems to be fine with people supplying their own ads and fits generally with Substack’s ethos of trusting writers to know what’s best for their audience. It’ll be interesting to see if Substack wants to offer these ads themselves, which would obviously put them more on the incentives path that has caused so many problems for social media, or if they’ll leave that alone.

The classifieds approach that Study Hall built strikes me as pretty ideal. It’s a fairly niche audience — geographically centered in New York but not exclusively, lots of media people who would likely classify themselves as “very online” — and doesn’t rely on surveillance to be effective. As a reader who pays to subscribe to at least one of those newsletters, I’m even fine with these showing up in my feed, as they seem like other bits of media I’d be interested in, not some D2C product I’ve been retargeted to have follow me around the web. Imagine that.