Rhett Rollyson
Founder & Principal
Rhett Rollyson founded The Rollyson Group and builds the agency's carrier partnerships. He is a lifelong Plant City resident and University of Florida graduate (1994) with deep roots in the local community, insurance, and tennis. He previously worked as an insurance agent with Fearnow Insurance in the Plant City office, specializing in personal lines (home and auto) and helping clients navigate coverage options from multiple carriers.
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Rhett currently serves as Head Men's Tennis Coach at Florida Southern College, a role he has held since July 2022. In that time he has led the Moccasins to multiple seasons of 15+ wins, consecutive NCAA Tournament appearances, a Sunshine State Conference (SSC) Coach of the Year honor (2025), and strong national rankings, while emphasizing player development both on and off the court.
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He is also a Director on the Board of the Florida Strawberry Festival (elevated in 2025 after roughly a decade as an Associate Director). In that capacity he has coordinated parking, chaired the Public Relations Committee, emceed events, and represented the Festival throughout Central Florida. Beyond these roles, Rhett has extensive experience in the tennis industry (promotions and player development with Prince and Babolat, tournament directing, and junior coaching) and remains active in other Plant City civic organizations.
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He and his wife, Tara, are the parents of two sons. That mix of insurance experience, coaching leadership, and long-term community service shapes how Rhett leads The Rollyson Group and its motto: do right by the client.
