"More on What Might Have Been"
I promised more thoughts on this subject, and I think Tim Lee’s post on The Innovator’s Dilemma is a good starting point and also reveals that my thoughts were less original than I’d believed. But the basic problem confronting a newspaper manager in 1998 or so would have been the fact that his firm was probably way too successful for there to have been a serious option of throwing chunks of the business model out the window and doing things in a whole different way in order to position it for long-term success as a digital media brand. Even if you’d had the foresight to see that doing this would make sense, you’d never be able to sell the other stakeholders on it.
Big, successful institutions have a lot to lose and have a ton of stakeholders and fixed investments in this and that. Even if you can see around corners and recognize that everything’s going to change soon, it’s just very difficult, in practice, to change things up so things that look foolish in retrospect could easily have been all-but-inevitable at the time the decisions were made.