Hey Goliath, I think you’re going down!

David and Goliath. A pretty famous tale. Little guy takes on the big guy. Logic tells us the big guy should win. But, instead, he goes down.

It’s hard to imagine a bigger Goliath than Microsoft. They usually win the fight. But this time, I think they’re going to go down.

This week, Microsoft releases Zune, their answer to the iPod. Their beige answer to the iPod. Over at the True Talk Blog, Tom Guarriello great job of comparing the two products.

Here’s the problem. Microsoft’s size begot a dash of arrogance and they made a classic marketing mistake. They forgot to ask the customer. In fact, they forgot all about the customer.

People buy the iPod because its cool. Cool colors. Cool online store. Cool features.

People buy the iPod because its convenient. Convenient to use. Convenient to find accessories. Convenient access to music, movies, TV shows and music videos.

People have invested a significant amount of money in iTunes downloads and iPod accessories. They are not likely to switch. They are likely to add to their iPod collection with either an updated version (so they can move all their files) or more iPod stuff.

Keep in mind the #1 target for mp3 players like Zune and the iPod are the tweens and the teens. They are all about cool and fitting in. That trumps functionality and screen resolution any day. And they are mortified if they appear to be "posers" or people are trying to be cool, but didn’t quite make it. I suspect Zune owners will be viewed as iPod owner wannabes.

The smart strategy for Microsoft would have been to either out cool and out convenience the iPod. But they aren’t doing either. They are counting on the holiday advertising push and the wifi feature (you can share music…but it evaporates after a few plays/days) to topple the iPod.

I don’t think that’s going to happen. Tomorrow, more on why not.