Jesse demonstrated his talent early in life, when in grade school at Mabry Elementary School (Tampa, FL) he was in talent shows for three consecutive school years. Additionally, he played the main role in several school plays. Furthermore, he was part of the grade school's first radio show entitled "DM84." He would later attend high school at H.B. Plant High with such talents as Morgan Simpson, Charlie Poe, Terryn Westbrook, Aubrey Chandler, Darla Delgado, Melissa Williams, Jackson Beals and Bert Kreischer.