Gregory grew up on the east side of Chicago, attending Christian grade school. It was when he became a freshman that he moved to the south suburbs and attended Homewood Flossmoor High School. During his first two years, he tried many extra curricular actives, such as the school band, the chess club, graphic design, and even fencing. It was during his junior year that he started his journey into the performing arts. Throughout his experience in theatre, he participated in numerous plays as well as joined the speech team. He specialized in Dramatic interpretation and won 1st place at the SWSC speech competition in 2010. During his senior year, he auditioned at the 2010 Theatre Fest in Springfield, IL. He received 25 proposals from different colleges to audition for their schools, and after receiving his high school degree, he auditioned and attended the University of Illinois at Chicago. Throughout his college experience, he studied not only aspects of performance on stage, but off stage as well. He participated in numerous stage productions as an actor, a lighting crewmen, and a stage manager. Throughout the summer, he also participated in numerous short films, his first being Perfect Day_. During his senior year, he developed a fondness for writing and directing, going onward to write, direct, and produce his very own original stage production in the UIC studio. Gregory went on to receive his BFA for Performing Arts in 2015.

Post graduation, Gregory participated in many stage readings, as well as being cast in the world premiere stage play of "Midnight Cowboy"(2016), which received a Jeff Recommendation.