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Why Windows Mobile and Palm will continue to fail

Microsoft and Palm continue to trip over the basics while the iPhone and Android maintain their momentum.

My previous post about mobile data sync brought in several public comments and many more private e-mails from various companies asking for perspective on how the leading mobile platforms will compete in the sync space and whether or not start-ups like Funambol can compete.

More than anything else, the leading mobile devices--the iPhone and BlackBerry, are marketed more effectively than any other platform, especially Windows Mobile, which by all counts should be the leader.

It's not that Windows Mobile is so terrible (you can decide for yourself), but that Microsoft hasn't done enough to make users want to use it.

In a conversation today, I learned a bit about Microsoft's My Phone service, which I had previously never heard of, and also a bit about Palm's strategy in relation to making the Pixi a device of choice for the younger set. Minutes later, the two worlds collided when I hit the My Phone site and came across this image of bitter irony.

Is this ad in context?
Is this ad in context? Screenshot by Dave Rosenberg

It's an ad for a Palm product that doesn't run Windows Mobile, or work with the Microsoft service, running on the MSN ad network, prominently displayed on the My Phone page. It confused me so much that I actually clicked on the ad to see if the services were somehow related.

There definitely is some logic from the Palm side--i.e. getting users to their devices, but this is an interesting failure of contextual advertising for Microsoft, allowing a direct competitor dominate the banner ad on their service page. Really, neither side benefits from the ad placement and considering the woeful state of both businesses, one would hope they care enough to not embarrass themselves and at least keep competitor ads off of their own sites.

While neither Windows Mobile nor Palm will be totally dead any time soon, if I'm on Apple's iPhone team, or working on Android, I wouldn't be too worried.