Roger Weller got into advertising by building his copywriting portfolio through freelance writing at small design shops. He moved to Chicago from the west coast and got a job at an agency called Bozell. From there, he moved to Cramer Krasselt, where he became a creative director.
Listen to Roger Weller's beliefs on branding, core marketing skills and the difference between advertising and public relations. The interview runs just under a half an hour, but I think it's one of the most insightful interviews on the marketing and branding world that I've heard.
Recommended Book
The Deviant's Advantage: How to Use Fringe Ideas to Create Mass Markets
Photo Source: Pink Ponk under Creative Commons