Microsoft’s thinking about targeting ads to Sync users in their car.

“We know where you are and we know where you’re headed. We could target that advertising directly to your car.”

When I worked at AT&T Wireless, I used to have an argument about this pretty frequently. They all went like this:
“We’ll be able to deliver ads to your phone based on where you are! So you’ll be next to a Starbucks and we’ll send you a coupon for $1 a latte!” (it was always Starbucks)
“Do you realize how many Starbucks locations there are in Seattle?”
“What?”
“There are dozens of Starbucks. Are you going to send me dozens of Starbucks coupons as I drive up I-5? I’d turn off my phone to avoid that. It’d be a horrible experience.”
“Um…”

You could, of course, solve this by only sending a few messages and upping the cost and the incentives for the user (“free latte at the Columbia Center Starbucks? I’m there!”) but the implementation ideas always ended up delivering horrible user experiences.

I’m not surprised that the idea hasn’t died: it’s so easy to think that there’s an impressionable customer base just out of current reach, and if only you could reach out and touch them, you could drive them to take a particular action. They just don’t ever think it through to the user’s perspective.