Dave Winer makes a good point about what MS could have (and should have) done with the Zune:

I met with the people doing the Zune at Microsoft in the summer of 2004, when podcasting was gaining traction (in Seattle no less), but wasn't showing on their radar yet. I explained how they could make their device a perfect podcast client. I couldn't tell what they were thinking of course, but it seemed they weren't convinced podcasting was real. Too bad, they could have made a simple product, not had to do any deals with Hollywood, and do an end-run around Apple, which still hasn't made the corner turn to DRM-less media (which is one of the most profound things about podcasting, and no accident, I assure you).

That's hardly the end of the missteps though; it's as if MS considered every bone-headed move they could make for the Zune, and went ahead:

• Doesn't work with Windows Media Player; requires a new application
• Doesn't work with PlaysForSure, MS' recent DRM theory. If you bought PlaysForSure music, that sound you hear is the theme song from "Jaws"
• WiFi that doesn't serve any useful purpose
• Music Sharing via WiFi that will generate gosh knows how many bug reports that end with tech support saying "it's a feature, not a bug"
• A player that's a little bigger than it could be, and is much heavier than an iPod.
• You buy music via a point system ($5 minimum up front to buy songs at $0.99 each) - unlike, say, itms, where you just use that money thing so manv of us are familiar with

It's simply amazing that they could hit the market as a second mover and make that many initial mistakes. That last one on points is worthy of a whole "what were they thinking???" post of its own. I'd like to know what the product management/marketing team was thinking when they came up with this.

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