As I have worked with different companies throughout the Midwest, I’ve noticed that different cities have different characters when it comes to expressing status and image in business. Madison, for example, tends to be a more laid-back city, where the number of Bentleys and other supercars can be counted on a single hand. Chicago is completely different, however, where I frequently see extremely nice and expensive cars. Driving a $100,000+ car seems to be one of the ultimate status symbols among Chicago businessmen, like the Aston Martin DB9 that I recently saw parked near Wabash Avenue: