4. Boyland Auto Group

In the 1980s, Dorian Boyland dominated the field as former first baseman for the Pittsburgh Pirates. In his second act, the Boyland Auto Group CEO leads the auto arena as head of the fourth largest black-owned auto dealership in the country.

Since 2000, Boyland has sprung to the top of the BE Auto Dealers list from No. 30 to its current position at No. 4. Although the Orlando, Florida-based auto dealer was hit with a 19% decline in 2008 revenues, the dealership group remains strong. Boyland operates 11 dealerships in six states including luxury car franchise Mercedes-Benz of South Orlando, Florida–one of Mercedes best performing dealerships in the Southeast.