Setting aside the ethical conundrum that the reason Windows 3.1 became popular was because good ol' Bill Gates and co. straight-up stole the source code to the Mac OS and crafted Windows from that source code. The last time Apple actually had a head start was the iPod (as John Gruber points out), not the original Mac. iPod sales are still booming even though the iPod Touch and iPhone are cannibalizing iPod sales. On the other hand, Microsoft's Zune business is still bleeding massive amounts of money.
Pundits in all topics need to pull their heads out of the anus of the safety of predicting a repeating history and see that history is a static series of events past, but the present and future are not bound to what's come before and are as dynamic and fluid as free will itself.
Can't it just be that Microsoft will not forever more dominate every endeavor they get involved in? Can't it be that sometimes they do get it wrong?
Yes, they do get it right from time to time, but they do so by not being willing to challenge or transform the status quo into something entirely new, which, in my opinion, has lead to their deteriorated public image.
If Microsoft put forth real innovation from time-to-time, perhaps they wouldn't always be playing catch-up. If Microsoft weren't dickish in what browsers and OSs their devices, websites, etc, support, perhaps they would curry favor with more people. Like the Linux and Mac crowds, for example, who believe-it-or-not are of a substantial number and do have a great deal of influence when it comes to recommending what service to use, which mp3 player to buy and so on. Why do they have influence? Because they are the pundits, the media, the nerds, the power users, and they are increasingly not using Microsoft products. If you have any hope of winning any of them to your side with whatever product or web-based service you are pushing, you need to make it totally and completely agnostic to both browser and operating system.
The Zune does not work on a Mac or Linux platform or anything but a Windows computer. Many of Microsoft's websites STILL lock out users of other browsers or operating systems. Internet Explorer STILL does not support loads of modern, web development features supported by ALL of the non-Microsoft browsers.
As it happens, Microsoft's board seems to behave like a bunch of pussies, and only seem to pursue things like vendor lock-in by forcing the use of Windows. In product development, more often than not, you see them imitating rather than inventing. i.e., they are still trying to follow their 10+ year old corporate playbooks and are not doing much in the way of adapting or innovating.
Sure, they have some interesting things. The improvements to Bing Maps is impressive. They have some pretty cool stuff being developed in their research and development arm. They made the "Surface" computer, and so on. I, however, still believe they're a dinosaur, and if they don't change their ways, someday their extinction will come. People are going to figure out that they don't need Microsoft Office, and that far better and cheaper alternatives exist. People are going to leave the operating systems of old (especially Windows) and move to computers of a whole new class that are not so complex, that are far more usable and secure. The iPhone, iPad, Google Android, and Google's Chrome OS are just a glimpse of where the future of computing is going.
Perhaps they will imitate again and find success again, but I for one, see them as increasingly becoming less relevant.
This concludes my tech punditry.
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