At first, the Open Source side was overmatched but mistakes by Microsoft and others allowed OSS to gain in strength and now both sides would seem to be more evenly matched. Neither side seemed capable of creating a successful strategy against the other and both sides seemed to respond to the other tactically.
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This seemed to benefit the challenger more than the entrenched vendor but, regardless of how often they competed with messages, for most of the last decade they actually seldom competed effectively for the same business opportunities. The two sides were simply too different but that fact seemed lost on both.
Even stranger is that both sides seemed to be hell-bent on damaging their own futures. And both, when attacking, seemed to be more effective at shooting themselves than at effectively moving against the other.
Microsoft Set the Stage
Initially Microsoft really didnt seem to take OSS or Linux seriously, which clearly wasnt the wisest tactic. Having lost track of their own progress down a path blazed by IBM a decade earlier, Microsoft was happily plodding along, systematically destroying the bridge of trust that existed between itself and its customers.
Seemingly forgetting the successful embrace and extend strategy that worked so successfully against Lotus and the emulation strategy that created Windows in the first place, Microsoft tried to drive Windows NT into a UNIX base that didnt want it. To showcase the power of the platform, they had a scalability day that, to this day, is unmatched in its historic failure to do anything but make the company holding the event look foolish and dishonest.
This was followed by a change in pricing which was supposed to address a complaint about Microsoft pricing complexity. And, largely because of an excessive focus on not taking even a short term revenue hit, it actually ended up being revenue positive and scaring the existing Microsoft installed base half to death by showcasing how vulnerable they were to the company. This base began to look for alternatives.
During this time one of the most common comments when a CIO was looking at increasing their Microsoft commitment was that such a move was simply not in their best interest. Yet Microsoft was convinced they could sell these same CIOs on abandoning UNIX in favor of Windows NT. This was a move that not only went against the prevailing will of these now concerned CIOs, it threatened the positions of those currently working on and managing the UNIX platforms that Microsoft wanted to displace.
This motivated the key stakeholders into looking for an alternative because all agreed that the cost savings of commodity hardware would be hard for operational managers to ignore for long.
In short, they needed something that could protect both the jobs of the managers that Microsofts products threatened, but ensure that they wouldnt be faced with the loss of control that resulted in excessive control by dominant vendors (like IBM had been) and Microsoft now was.