As part of the Google Online Marketing Challenge, a team of Darden students devises an AdWords campaign for Motorcowboy, an online source of custom footwear that caters to segments as varied as motorcycle police, cross-dressers, movie buffs, equestrians, and plus-size individuals. When an initial keyword list yields low traffic, the team must adapt its approach. This three-part case illustrates the segmentation process and the relative merits of paid search over traditional mass media outlets. It also serves to underscore the importance of monitoring and adapting any advertising plan.