There are two extreme cases that come to mind immediately:
Sears. The original "online" order store. The catalog had everything, and was the source of millions of Christmas wish lists. They even had dedicated pickup locations for their mail-orders. All they had to do was build a decent website, and we would have never heard of Amazon. Instead, they are just a chapter in retail history.
Kodak. Once a Dow Jones hero, it ended up a pink sheet zero. They invented the digital camera, and then spiked the product like the NY Times spikes stories about Dems. Hey, don't want to mess with our core product - film. Could have remained the leader of worldwide picture taking, instead, shrunk to the size of a Photomat booth before they disappeared like pictures on undeveloped film exposed to light.
I'm sure others can add many more, but these two stick out as catastrophic business failures.
Unfortunately, Obama bailed them out so I doubt that they have learned from their mistakes.
Anyway, we are cheering for the day when they close their doors.