Here’s what he’s doing: “licenses for updates and support will be sold for each major version, and they don’t expire.”
I know first-hand the uphill battle it was to build a healthy revenue model as a WordPress product company. For the first 7-8 years we didn’t have automatic subscriptions, and then after we did it felt much more sustainable.
Jon mentions “subscription fatigue,” which is a growing issue I’m sensing as a customer now. It goes against the grain of the overall WordPress product space for sure, but we’re eager to see how Jon’s experiment goes.