Born and raised in Fort Myers, Florida, Sherry grew up playing a number of sports during his high school career. He ultimately chose tennis as he earned a scholarship to play at the University of Florida.

In addition to his success in pickleball, Sherry co-founded Legacy Pro Sports which provides assistance to former NFL players as they transition out of the sport, Sherry’s main focus in this industry is helping players file for disability claims. Through this venture, Sherry has had the opportunity to meet a diverse group of people, including entertainers, actors and celebrities of all kinds. With his representation of more than 5,000 former players, Sherry’s work with Legacy Pro Sports has helped earn these former players more than $200 million dollars in disability claims.