Jake took up golf, and began pursuing a career as a professional golfer, winning his first tournament at fifteen. After graduating from Vero Beach High School, they attended Florida State University. A wakeboarding accident which resulted in reconstructive surgery left Jake unable to continue playing the sport.
While recovering from his injuries, he borrowed a neighbor's guitar and began to teach himself how to play it. After seeing a guitarist perform at a campus bar, he asked the bar's owner if he could play a gig there. Eventually, he became a regular at the bar, and soon took up writing his own material as well.