Microsoft’s biggest problem these days isn’t technology, it’s ecosystem, or corporate strategy. Instead it has something far worse — a perception problem. There’s a ton of historical evidence — monkey boy, M$ (a slur used by geeks to describe corporate greed), Apple’s Mac vs PC (it wouldn’t be effective if the perception didn’t already exist), etc. — and more keeps popping up all of the time.
For instance, while slamming offline web apps, Dare laments the anti-Microsoft sentiment in the Web 2.0 crowd. It appears he’s suggesting that ill will towards MS is so great that Google Gears was developed and praised only because of the potential harm it might do to Microsoft. I’m not attempting to slam Dare or his argument (he has some valid points), only highlight the reaction elicited as a result of the MS perception problem.
(Note: I’m not sure I buy his “desktop” apps are far richer than web apps generalization in today’s RIA age, but its an arguable point)

It also gets, if you’re lucky enough to be the CEO, eggs chucked at you during speaking engagements.
The problem Microsoft has is that even with superior fire power ($274 billion market cap) it’s losing the all important battle for hearts and minds. I’m not trying to make the argument that Microsoft is pure unadulterated evil and it’s all roses everywhere else. Google seems to want to own your personal information and advertise to you in disturbing ways (although what company doesn’t), but they still have a generally positive perception amongst the rank and file (its a fun verb we all use). Apple is certainly no stranger to vendor lock-in and wrapping your content in a layer of crud, but they package end to end experiences so well that they continue to have a high degree of consumer good will.
Microsoft on the other hand, comes across as a caricature of greedy monopolists constantly looking for ways to subjugate an entire set of industries–OS, video, mobile, search, gaming consoles, game development, servers, browsers, etc. The actions of its executives and business units reaffirm this negative perception despite the many positive interactions we may have at the individual level (what’s it called when the behavior of the group doesn’t match the beliefs / behavior of the individuals that make up that group). For many this results, justifiably or not, in a toxic swirl surrounding all emanations from Redmond and that folks is a big, big problem. I’d offer up advice, but somehow I don’t think the suits would listen.
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[...] that Microsoft is cool enough for them to give up their Apple. Article just emphasizes the perception problem MS has. It’s 6 pages, but the first page and a half and the last couple of pages contain the [...]