Here's a fun sign of the times: a Pandora listener, Kyle Taylor, aired an "ultra-targeted" ad to his girlfriend of 6 years recently. It was a marriage proposal, and his girlfriend heard the custom ad in her Hyundai Veloster (which has Pandora built-in to the dashboard).
"I started to work with the team at Pandora and they told me this has never been done before, so they would be more than happy to help," wrotes Taylor at his blog. "After working with the creative and technical teams to figure out the best medium, getting passed to their audio advertising team to get a script together and recorded by an awesome voice actress, and once it was finalized it went back to ad trafficking to test out my ad and see if it worked. Of course, it worked out perfectly."
In more ways than one: she said yes.
However, Taylor apparently had to do some demographic manipulating to get this to work. Pandora targeted the ad to "very old listeners" in a "sparsely populated zip code." Taylor then entered some fake demographic info into Pandora to hear the ad. That way, it was "very, very unlikely" any other listeners heard the very personal ad, according to CTO Tom Conrad.
Still, an interesting and creative use of the powerful targeting abilities of Internet radio. TechCrunch has more coverage here.