Gaines is a third generation member of the Dempsey Auction Co. Gaines has been with the Auction Company full time since 1999. He obtained his real estate license in 1997 and worked all throughout high school and college with the auction company.

Gaines is a graduate of Darlington School and the University of Georgia. Gaines became a partner in Dempsey Auction Co. in May of 2005. He and his wife Amy have two little girls Cade (August '05) & Callie (December '08).