What are the timeless truths of advertising? How can agency leaders manage their teams, their creative talent, and clients? To answer these and other questions, the mythology of the ‘Golden Age of Advertising’ is examined and analyzed herein. Specifically, using ad man Don Draper—protagonist of the fictional, but already culturally iconic, television series Mad Men—as a mythic archetype, lessons are extracted for contemporary advertising practitioners. Ten timeless rules are proposed and explicated in the areas of (1) managing intra-agency leadership processes, (2) managing creative processes, and (3) managing client relationships.