Point, Click, Pay?

(AP)
It’s 2007 and almost nobody has devised a sustainable way of making money on content online. Heck, I spent a semester worth of grad school ten years ago – writing a hundred pages – looking into Internet financial models and could only end up with a heavily-footnoted shrug.* That was back in the days when Slate.com was still attempting to charge $19.95 for a yearly subscription. (They were saved by Microsoft in 1999.)
The problem, of course, is that you can find (almost) anything out on the web for free. So there’s absolutely no incentive to pay. Back in November 2005, the New York Times decided that they had figured out a way around this problem – a hybrid experiment where they would offer their news content for free, but charge for the unique commentary of Tom Friedman, Frank Rich, Maureen Dowd, et al. So they began “TimesSelect” and began charging non-subscribers $49.95 to access the opinion page online.