As someone who used to run a media website somewhat smaller than TheRinger but still in the same general ballpark, I have also been thinking about this question. The answer is probably simple. Free written content on the Internet used to be a loss leader. Now it's just a loss. The golden age is dead, y'all. It's all subscriptions and passion projects now, I'm afraid.

Nobody Wants To Talk About Why The Ringer Is Pivoting To Substack | Defector
A media company launching a series of paywalled newsletters is not, on its own and on its face, a strange thing to do. AI’s ongoing cannibalization of online search is ravaging website traffic, and programmatic advertising doesn’t provide the kind of revenue it used to. If you were running a website like The Ringer, you…
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