Tom currently sponsors two contests a year for board designs.  The rules and schedule are ever evolving, but the latest can be found here:

Schedule - https://docs.google.com/a/prestopnik.com/spreadsheet/ccc?key=0AjtIsJkyopekdEpUeW84NlRjYzhlQkptNjdTSjFnb3c#gid=0

Rules - https://docs.google.com/a/prestopnik.com/document/d/1XYstgt4nHKN9yJDNP2dw25dSz1kVbLlEsxqlIVuzYHM/edit

The theme changes for each contest.  In the past we've had: "Old West / Westerns","Dr. Seuss","LEGO" and "Escher/Tesselations".    As of June 2013, the "Educational" contest is in the voting stage and the 'Arcade & Classic Video Games' is in the design stage. 

Currently the prize structure is:

• First prize: $100
• Second prize: $50
• Third prize: $30
• Fourth, Fifth prize: $10

I help organize and facilitate the contest, but all decisions on how to run it are based on community input/voting with Tom having the final say.