Looking back both Apple and Microsoft (Disclosure: Microsoft is a client of the author) made pivotal strategic mistakes in their operating system strategies that the other firm did well.  In each case the company seemed to walk away with the idea that the strategy was bad when it was clearly, after analysis, that the execution was the problem.  Apple tried to both license the operating system in the 1990s and sell hardware, a practice that failed badly and Steve Jobs eliminated the effort.  

Microsoft tried to get the same operating system to work on PCs and Smartphones and that failed equally badly and has mostly been shut down as well.  However, the Microsoft Surface line of products has been surprisingly successful, and Apple’s sales of the iPad Pro, which is more of laptop than a tablet in use, has been doing very well showcasing that the idea was viable but the execution was at fault.

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