I think the article is a nice summary of why Microsoft lost, but it doesn't fulfill the promise of its title. "Should have won" implies that there were steps Microsoft should have taken to overcome the difficulties it faced. Let's explore some: Lack of vendor trust, not wanting to get locked in with Microsoft like PC-makers did. No easy solution there. Hampered by success of cash-cows like Windows/Office. Shouldn't M…
They had just the same opportunity to do mobile web as Apple - CE devices could run a real browser. Unfortunately, that browser was IE. I think Apple's real innovation was the App Store, combined with a usable (non-resistive) touchscreen. Prior to the App Store, it was remarkably hard to get apps onto phones. You were dependent on the mobile carrier, whose levels of customer gouging made Microsoft look like newbies.…
I had the AT&T flip-phone pictured in the article and it is my favorite phone ever. The CE shell and bundled apps for non-touch devices were extremely well adapted to the constraints. The one thing I remember well is that I could open it up, punch in 666, and besides showing dialing that as a number it would bring up a list of matching contacts to select from. 666 == MOM. I've never held another smartphone which did that.
Microsoft lost because their successful platform was a fantastic phone with so-so data features and the iPhone flipped the game around.