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Googlemail & Hotmail both search the content of your e-mails and then serve up advertisements based on that content. [Assuming you’ve given them permission]
This contextual advertising then appears, on Googlemail at least, down the right hand side of the page next to your e-mail.
I’ve noticed that because my e-mail signature contains my qualifications it regularly serves me up adverts for MBA courses etc.
I’d have to say it does what it says on the tin with regard to content matching, the problem comes with matching actions.
How often do you talk in advance about what you are going to do?
I think we all generally talk about what has happened in conversations and this applies to e-mail as well.
If this is the case the potential of an advert to modify your behaviour may be too late.
Google AdWords gives you the option to turn off your adverts from content match and that is what I’ve done to date.
The reason being that I think a budget is better being used up by results to customers actually searching for a service or product, rather than those who may or may not be interested in you business picked up purely by e-mail content.
If you have money to blow then go for it but I’d use it on Yahoo!™ or MSN first, depending on what happens with the Microsoft takeover.
