Billy is a native of Key West, where he was raised before graduating from Key West High School in 2000. After attending college at the University of Florida, Billy started his professional career as an attorney in Tampa Bay. After five years of practice, Billy and his wife, Michelle, decided to permanently move to Key West, where they now reside with their children, Brantley, William III and Leighton.

Billy is an attorney with a background in finance and real estate development, and currently serves as Chief Development Officer for Spottswood Companies, Inc., a family-owned company that operates a diverse portfolio of hospitality and real estate businesses.

Billy is an active member in his home community, serving on the Board of Directors for the Key West Chamber of Commerce, where he is Vice President.