I don't know if this really adds anything, but I have a friend that as a young tech entrepreneur was on the cover of Forbes and made a cool few mil. Then he blew it all, did porn sites, and was pretty poor for a while. Now he does consulting and makes a living (is in his mid-forties)

So he says he regrets going the "porn" route because it wasn't ultimately profitable. But that's not really what you're asking. That, I have no anecdotes for.