Whittle was born in Etowah, Tennessee. After graduating from the University of Tennessee with a major in American Studies, Whittle started the magazine "Knoxville in a Nutshell" with Phillip Moffitt and others. He started the 13-30 Corporation in Knoxville. In 1979 13-30 bought "Esquire" magazine, where Whittle served as chairman and publisher for a number of years. In 1986, 13-30 became Whittle Communications, which was one of America's top 100 media companies in the late 1980s - known for creating and publishing single-advertiser magazines that were placed in medical office waiting rooms. In 1989, Whittle Communications launched Channel One News, a national in-school television news program (first anchored by Kenny Rogers Jr., Brian Tochi, Michele Ruiz, Hicks Neal, Kathy Kronenberger and Mark Carter). Channel One News' programming reached eight million students daily in 12,000 schools and won the Peabody Award. Whittle sold the company in 1994.