"if you're basing your business model on creating a "class" of services that annoys your users quite a bit that they're forced to "upgrade" to the less annoying option, you have to be pretty damn sure that they can't just go and find the less annoying version next door. Or in the next thousand doors."
Which is exactly why some paywalls DO work - when the source provides targeted niche content or is the sole provider of content for that category. They may not provide great user experiences but if they do meet specific business goals, then they are successful. (witness: WSJ, FT).
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