This an interesting story about the birth of Gmail and Adsense. This was before Adsense was released, but the ad matching system was used in-house at Google was an early prototype.
http://blogoscoped.com/archive/2007-09-03-n78.html
Quote:
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Well, despite Marissa’s repeated stance on this, Paul went ahead and, during one night – utilizing an open source semantic analysis library found on the web, and hooking it up with Google’s existing AdWords database search system – he coded something that would put targeted ads into Gmail. Note this was before Google had AdSense. Marissa was in for a surprise the next morning checking the prototype, and immediately wanted the ads to be taken out... but also wanted to be patient to wait for Paul to arrive at the office, as he just went home to sleep after pulling the all-nighter.
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