Kelley grew up on a farm that included tobacco, and his early Business ventures were a response to changes in the tobacco industry. Because of declining production in the 1980s, many old warehouses in Kentucky stood vacant. He started buying these warehouses, converting them to other uses, and then leasing them out. This interest evolved into Manufacturing. In 1991, he founded Commonwealth Brands, a tobacco company that manufactured low-cost cigarettes, headquartered in Bowling Green, Kentucky. The company was later sold in 2001 to Houchens Industries for US$1 billion. Kelley has never smoked, and he said in 2012, "I've never defended [smoking]. Hopefully it will be phased out of society."