The Wired Vaporware Awards '06 was announced this week and item #8 is The IPod Killer. Specifically the article states

8. The "IPod Killer"

Every time we hear about a new portable audio device, it's touted as the magic bullet that will end the iPod's reign once and for all.

Oh, you mean that thing? The one with the ugly design and clunky user interface? Does it at least work with iTunes?

Microsoft's Zune was supposed to do the trick, but it's sitting on the shelves (even the SanDisk Sansa is selling better than Zune) while the kids are all enjoying their freshly unwrapped, shiny new iPods.

Note to everyone: It's a White Wire World. Get over it.

I've bought a lot of iPods in my day and I've been making a list of things I'd like to see out of Microsoft's Zune effort that would tip the scales and make us go from a multiple iPod household to a Zune household. Below is a list of the 5 things that I think it would take to convert myself, my girlfriend and her oldest daughter from iPod users to Zune users based on conversations we've had about switching.

1. Improve the Pocketability Factor: If you check out pictures of an iPod and a Zune side by side you'll notice that the iPod is thinner and shorter. Since I carry an MP3 player around a few hours a day either around my arm when working out or when walking around at work, the less bulky it is the better. My girlfriend definitely doesn't want to walk around with the outline of a rectangular brick in her pants especially now that skinny jeans are in

2. Do Something Cool with the Wifi: At Christmas dinner, I was talking to a family friend who just graduated from college and she asked me about the Zune. She perked up when she heard about the Wifi capabilities and music sharing until she found out the limitations in the music sharing capabilities (3 days or 3 plays) which she described as lame. I doubt that there is much that can be done to make the music sharing feature interesting to college kids since [as she told me] they just want free music. However there are a lot of cool things I can imagine doing with a portable music player that has Wifi. For example, what if I was listening to a song on the radio on my Zune then could purchase that song in a few clicks right from the device? What if I could receive internet radio with no ads on my device?  

3. iPod Dock Connector Compatibility: A lot of people mistakenly think that the large investment that prevents people from switching from an iPod is the library of songs they've purchased from iTMS which won't be compatible with another DRM system. However in my experience I've noticed that the huge range of iPod dock connector accessories is becoming more of a factor. After all, auto manufacturers from Chrysler to Ford, GM and Mazda are all shipping iPod-ready cars. We spent a few hundred dollars converting my girlfriend's SUV to an iPod-ready one. Then there's all the travel speakers, including my Christmas present a FUNKit DJ iPod Speakers. Re-buying hundreds of dollars worth of accessories doesn't fill me with glee. However if we could go to an electronics store like RadioShack and get a an iPod<->Zune connector that would ease the transition a great deal.

4. Smaller, Cheaper Versions: The iPod Nano has totally swept the young girl demographic. Whenever we end up at the mall and I'm dragged to Claire's I tend to see a lot of iPod Nano accessories but very few for the video iPod. We need a Zune that targets that demographic.

5. Celebrity Product Placement: I almost feel embarrassed to admit this but the tipping point for getting my first iPod wasn't when all the gadget wunderkinds at work got one or when I almost fell of the treadmill because I was switching CDs on my portable CD player. No, the tipping point was when I saw 50 Cent using one in the P.I.M.P. video. If you want to impress me with the cool kids that are using the player, don't show me annoying looking hipsters I probably couldn't stand if I met in real life. Another good example of this kind of product placement is Mariah Carey using a RAZR in the Shake It Off video.