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Apple's Tortured Relationship with the Enterprise

NEW YORK (TheStreet) -- After the desktop publishing bonanza of the late 1980s that was launched by the early Macs and laser printers, Apple (AAPL - Get Report) sought to further develop its position in the business world.

But as history tells it, a mistake by CEO John Sculley opened the door to Microsoft's (MSFT) Windows. By 1995, Microsoft was briskly improving its control of the enterprise with, after some false starts, Windows 95. At the time, the casual and damaging consensus was that Windows 95 was "just as good as a Mac," and by early 1996 Apple was foundering.

This is not the place to retell the story of Steve Jobs's return. It's been superbly told by many others, in book-length form. What I do want to do, however, is relate some of the interesting observations I encountered from my own experience because they shed light on Apple's topsy-turvey relationship with the enterprise over the years, especially since 2000.

CIO Encounters

When I worked for Apple in Federal sales, starting in 2003, I was assigned to sell into the Federally Funded R&D Centers. I met with almost every CIO of those organizations, and they were generally in the Microsoft camp. Microsoft products were designed for the enterprise from top to bottom. Microsoft understood the business needs of the enterprise and government and "checked the boxes" for the CIO's needs.

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So firmly entrenched was Microsoft that, even when confronted with a superior, more secure UNIX OS, called Mac OS X, they generally declined. That's because convincing one person in an organization, even a CIO, won't turn the ship around. Plus, an OS is just a point solution. The whole suite of business services, such as the Microsoft Exchange Server, was more critical to a business in their view. Finally, Macs being the very best were too expensive, and every business wanted the cheapest possible hardware for its cubicle dwellers.

Of course, I had champions in some of those agencies, but by and large if an organization was already Mac-friendly, and they were few, sales were brisk. Otherwise, it was an uphill battle. Organizations don't change unless there's a catastrophe. (And in some cases, there were some major security events with Windows XP that earned Apple important customers.) But those were small battles, not the larger war.

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