[3] He was interested in filmmaking from an early age and began to use his parents' video camera to create stories with his brother and a friend, including a makeshift version of Titanic in Brookline, Massachusetts.

[1] His interest in the craft further developed during his time at Brookline High School, where he participated in the theatre program and took a life-changing video production class during his junior year.

[1] After completing high school, he worked for City Year in Boston, producing a recruitment film, before beginning his college education at Fitchburg State University in 2007.

[1] In 2012, Freeman made his directing dabut with the documentary The Last Taboo, which explored the sexual lives of people with physical disabilities.

[4] In 2017, Freeman's documentary The Wounds We Cannot See chronicled Nancy Ross's struggles with post-traumatic stress disorder (PTSD) and addiction.