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I had polar opposite targeting experiences today on Yahoo and Google.

On Google, I was using GMail to email my friend Kevin about setting up a lunch. The email chain was pretty boring stuff: are you free on this date? where do you want to meet? and so forth.

In the past, Kevin and I have also emailed about college football – I’m a big Iowa Hawkeyes fan, he’s a big UCLA fan.

For this reason, I was pretty impressed to see AdSense ads showing up alongside our banal lunch email chain with the following headlines:

  • UCLA Fightsong Ringtone
  • College UCLA
  • UCLA Bruin Tickets
  • Bruins Ringtones

Sophisticated targeting going on here. Somehow AdSense has associated my friend Kevin with UCLA (who knows, perhaps this is all he ever emails people about, but I doubt it) and therefore serves UCLA-related ads whenever I read any of our email chains.

In contrast, I regularly surf my “My Yahoo” page to check up on the various paid search blogs that I read, my stocks, my favorite sports teams, and the latest world news. Yahoo has a ton of information about me based on all these feeds and my emails. And yet, about 75% of the ads I get are the classic “free iPod” banners. Most recently, I was asked to vote on whether I liked Hillary Clinton (and ‘win a prize’ for participating), and to participate in a ‘test panel’ to receive a free dinner for two at Chili’s.

These ads are clearly “run of site” or “ROS” ads that Yahoo is selling for pennies per CPM. Not to toot my own horn here, but I’m sure that there are plenty of advertisers out there that would pay a lot of money to target ads to me. I’m a Silicon Valley marketing executive with a lot of disposable income (well, a lot more than the average American at any rate). You could target me with bid management software, CRM, conferences, travel, fine dining – there are many ads that might appeal to me that could pay Yahoo big bucks.

But instead, I get the product test panel ROS. Google’s remembering my old email conversations, and Yahoo can’t differentiate me from a 12 year old in Tulsa. And you wonder why Google’s stock is 20X Yahoo’s.