A native of Statesville, North Carolina, Robert grew up working in his parents' grocery store, Gilleland's Grocery. He attended UNC-Chapel Hill as a Morehead Scholar, graduating with a Journalism degree in 1972, after being inducted into Phi Beta Kappa and twice serving as President of Chi Phi fraternity. He married his high school sweetheart, Cathy Ross, moved to Sanford, commuted to law school at UNC-Chapel Hill and began law practice in Sanford in 1975.

His practice areas are commercial and residential real estate, business organizations, wills, trusts and estate administration. Robert is a past President of the Jonesboro Rotary Club and Sanford Area Chamber of Commerce. He attends First Baptist Church, serves on the Board of Directors for Salvation Army, acts as attorney for Habitat for Humanity, and provides backup vocals for a solid gold band, RN5P. Robert has been voted Lee County's "Best Attorney" four consecutive years by a poll of readers of The Sanford Herald.