Robby was adopted as an infant, at just six weeks old by a loving Baptist Minister and his wife. As the son of a preacher, Robby and his family moved frequently across the south. Robby graduated from Midland Valley High School in Langley, South Carolina in 1986. He then attended Furman University where he obtained his BA degree and played for the 1988 NCAA I-AA National Championship winning team. He furthered his education by obtaining a MEd in adult education from the University of South Carolina, where he also served as an assistant football coach for the Gamecocks, under the direction of legendary head coach Lou Holtz. He moved on to become the defensive coordinator at South Carolina State University in 2002. As the Bulldog's defensive coordinator from 2002–2005, Wells' defense attained several national rankings and a Mid-Eastern Athletic Conference championship in 2004. In 2006, Robby was hired as the General Manager for the Augusta Spartans Arena Football Team where his duties included coaching, player personnel decisions, player development, team travel, fund raising and media relations. In April of 2006 during the middle of the Wars in Afghanistan and Iraq, Robby joined the Army National Guard. During the summer of 2006 while he was training at Fort Sill, OK, Mr. Wells played a vital role in saving the lives of sixty soldiers when a rogue trainee began stabbing soldiers in the night, while they were trying to sleep. Specialist Wells, along with other members of his platoon acted quickly and appropriately to care for the wounded and to subdue the rogue trainee, ensuring that everyone survived the attack. He went on to become the defensive coordinator and football marketing director for one season at Benedict College in Columbia, South Carolina in 2007. Robby was hired as the head football coach on December 22, 2007 at Savannah State University, an HBCU. In his first season as head coach, they saw as many victories as the previous four seasons combined. He is the most successful head football coach that Savannah State has had in the past two decades.
In November of 2011, Robby retired from college coaching, and began a different kind of service. Robby has run as a Presidential candidate, and in 2020, appeared on numerous state primary ballots. In addition to running for Congress, Robby also serves as an ambassador for the International Human Rights Peace Commission and has spoken in India, China, France, Italy as well as domestically. He also serves as a foreign news correspondent for several global television news networks, and is a published author. Robby also serves as a member of the U.S. Coast Guard Auxiliary. Professionally, Robby is the Vice-President of an aviation sales company, and also owns a large life insurance agency. Robby makes his home in Botetourt County.