The first digital camera was invented at Kodak. Kodak invested big money into commercial digital cameras early on, and they even bought some on-line photo sharing businesses. So why if they had invested significantly into technology, why did they still fail to jump the gap when it came? This article goes into a lot of detail but clearly a lot of big companies failed to see that the internet could reach directly to end users and how much could be advertising driven.
As an aside, when I was Director of Engineering at Operon working on optimizing the DNA synthesis machines we were building, some of my research led me to science being done at Kodak. It’s still amazing to me how many great scientists and engineers they had and the breadth of work being done there.