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Apple Fools: Times the House of Jobs went horribly awry
Plenty of bumps in the 40-year road for Mac makers
Getting passed by Microsoft and Windows
The early versions of Windows were not exactly threats to the MacOS when it came to cosmetics and function. As with many of its hits, Redmond didn't get a home run the first time around, but persisted until they got it right. In the case of Windows, this started with Windows 3.1 in the early 1990s and continued with Windows 95.

All it took was 10 years and billions of dollars
While Microsoft was refining its GUI-based OS into a decent environment, Apple was letting itself crack under mismanagement and a pair of crucial missteps in their development roadmap.
The first of these was "Pink", the late-1980s effort to revitalize the MacOS with a number of important features that would have kept the Macintosh Operating System up to snuff with a microkernel-based OS that was to be the basis of the new PowerPC hardware platform.
The development never came about, and a few years later another Apple misstep would lead to the disastrous Copland project. Another attempt to refashion MacOS into a more modern platform capable of getting out way ahead of Windows again, Copland failed and Amelio was forced to look elsewhere, luckily to Steve Jobs, who thanked the management team by ousting most of them.
Around that same time, we had...
The ill-fated PowerPC
It's hard to say that a brand that endured for more than a decade was foolish, but in Apple's case the PowerPC just wasn't a great deal. Developed in a joint venture with IBM and Motorola, the PowerPC was the trio's answer to the Wintel menace that arose in the 1990s.

The 'IBM' logo was the first sign it would go poorly
The PowerPC itself compared well to Intel for much of its life, but as the only desktop platform really using the CPUs in desktops and notebooks, Apple was at a disadvantage. When the company rebranded in the early 2000s, Apple decided it had been stubborn long enough, and did the sensible thing by moving over to Intel processors.
Don't feel too bad for the PowerPC, however. It has enjoyed a fine life post-Apple as its descendants would be used for both the Playstation 3 and Xbox 360 consoles, as well as IBM's Power server line.
Before the switch to Intel, though, Apple would make a less successful foray into the PC world when it inexplicably shoved...