I think it has already been written: https://en.wikipedia.org/wiki/The_Innovator's_Dilemma https://en.wikipedia.org/wiki/The_Innovator's_Dilemma ;-) You are

I think it has already been written: https://en.wikipedia.org/wiki/The_Innovator's_Dilemma https://en.wikipedia.org/wiki/The_Innovator's_Dilemma ;-) You are correct, a specific dive into what went wrong at Sears and why they aren't Amazon today would be incredibly valuable. But re-reading "The Innovator's Dilemma" sheds some light as to why they not only didn't, but really couldn't catch the Internet wave. Incumbents need to recognize when a disruptive, extinction event is looming, and everything in their culture works against that. Typically, when one of these things comes along, sales are robust, the incumbents have cemented the value of their brands, and their margins are industry-leading. It's very difficult for incumbents to even see the disruption as a threat, much less to pivot, embrace the disruption, and disrupt themselves. When you're running a successful business, it is nearly impossible to decide to go all-in on a new business that will cannibalize your existing business at lower margins. If you're a public company, your stock will head right down into the sewer to be gnawed upon by short-selling Norwegian Rats.