Bobby was born in Dunwoody, Georgia and began playing tennis at the age of 7. He attended Dunwoody High School where he was a member of the state runner-up tennis team in 2006. He played all four years on the varsity team and won Most Valuable Freshman. He played tournaments during high school and earned himself a scholarship to play at Ohio Dominican University in Columbus, Ohio. He was part of many successful teams while at Ohio Dominican and competed in the NAIA National Championship Tournament. Bobby dual majored in Business and Finance and received his M.B.A.