A native of Kent, Washington, Cappelletti grew up in Alabama and attended Bob Jones High School, where he was a three-sport athlete.
Three years after ending his club career, he was called up for the first and only time by Guam, earning three caps at the 2017 EAFF E-1 Football Championship.
[1] As a child, he lived in Tennessee and Germany before his family settled in Madison, Alabama, ahead of his sophomore year of high school.
[5] Following his two years at Wallace State, he was recruited and received a scholarship to attend Valparaiso University and play under head coach Mike Avery.
[3][6] Joining Cappelletti in transferring to Valpo was his Wallace State teammate Roby Del Giudice, and the Crusaders' 2009 recruiting class also included Stefan Antonijevic.
[8] He went on to appear in 13 matches during his junior season, including starting in all three games Valpo played that year against ranked opponents.
He signed on to play with National Premier Soccer League club Rocket City United, with who he would spend two seasons.
[3] In October 2016, three years after ending his club career, Cappelletti was called up for the first time by the Guam national team for the 2017 EAFF E-1 Football Championship.
[15] He made his Guamanian debut on November 6, 2016, replacing Ian Mariano at halftime of an eventual 3–2 defeat against Hong Kong.
[30] To fill out his staff, Cappelletti hired his youth and college teammate Chace Zanaty as an assistant and brought in former American international Nate Jaqua as strikers coach.
He and his fiancée moved to Ohio, where Cappelletti took a position as a coach at Cincinnati-area youth club Cincinnati United SC.
[23][34] Cappelletti spent two years at Cincinnati United, then in 2021 was hired as an assistant coach for the Western Oregon Wolves, a brand-new NCAA Division II program.
[36][37] Ahead of the 2023 season, Cappelletti briefly joined North Alabama SC as the club's assistant director of coaching.