I remember Steve Ballmer laughing his butt off when the iPhone debuted. People here are quick to point out and revel in Apple’s “failures” but this colossal and monumental failure of Microsoft to even grab a piece of the mobile/wearable market is undoubtedly the tech failure story of the 21st century so far.
I remember how incredibly clunky Windows Mobile was back then. You needed a stylus for most parts of the UI. The UI was ugly as hell and difficult to read. It was extraordinarily unpleasant to use. PalmOS was worlds better, yet so many people still used Windows Mobile because it was adopted by corporate IT departments.
Windows Phone was an improvement in usability but killed most of the power-user capabilities that made it attractive to enterprise use.
All this said, I'm sad that Windows Phone failed. Apple needs competition to stay innovative. They've kind of stagnated as of late. Hopefully something awesome will come down the pipe soon now that sales are suffering.