#2 - Microsoft didn't try - With Apple merely treading water in 2006 it seemed that there might be room for a challenger. The obvious candidate was Microsoft's Zune.  On paper the Zune looked like it could be a serious contender. It had some novel features like wifi and song sharing. It had a nice display and cool interface.  But the Zune had a few problems at launch.  The gadget bloggers had horrible install problems with the first Zunes.  There were some rather strange images and advertisements. The device itself looked and felt like a brick compared to the iPod.  The device didn't support podcasts.  It didn't work with Vista.  You had to use confusing Zune Points to buy songs. And on and on. Now these glitches could have been forgiven - Microsoft is known for under-delivering on version 1.0 products - if the core experience was novel and interesting.  But the key distinguishing feature of the Zune - the song sharing (aka 'squirting') was hamstrung - by overbearing DRM - the shared songs would dissolve after 3 plays or 3 days.  The Zune wifi couldn't be used for syncing or listening to streaming internet radio.  Microsoft turned its back on its PlayForSure licensees by creating a new and incompatible DRM - (the only reason was to create their own iTunes-like proprietary music silo) and perhaps worst of all Microsoft bought into the fiction put forward by the music labels that anyone with a digital music player must be a thief. Microsoft agreed to pay a music tax to Universal for every Zune sold.  It was almost as if Microsoft wasn't even trying with the Zune.  Bill Gates even said admitted that Microsoft had only 'modest' aspirations with the Zune.  Despite my misgivings about Microsoft in general, I was really hoping that they would do something interesting with the Zune - at least that would stimulate some innovation in the digital music world.  But I fear Michael Robertson's prediction about the Zune will be right on the mark. 

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