I am the owner of a small but growing business that targets the parents and coaches of youth sports (and other youth activities like dancing) participants, particularly travel team members: www.mykidscalendar.com As part of our service, our system generates automated emails when, for example, a coach changes a practice time (or reminders are sent by the coaches/administrators). The emails are created by our system and sent to the parents of the players on that coach's team. In September, our system sent over 18,000 automated emails, growing from over 13,000 in August. The October figure was 21,000. The emails are not spam: parents rely on them to understand what changes have been made to their children's team schedules, so they generally are interested in their content. We are currently offering ad space on those emails via a banner ad, and have the ability to track clicks. We're currently running a charity ad (for free, of course), and in September, saw a 1.08% click rate for that organization. Typical website banner ad companies are locked into a traditional website banner ad paradigm, and I've found it difficult to gain traction there. Any ideas as how I might best find interested purchases for this unique advertising space?