Masekela was born in Los Angeles, the son of a Haitian mother and South African jazz musician Hugh Masekela. Masekela is also the older half-brother of Survivor: Cook Islands contestant Nathan Gonzalez. He was raised in Staten Island, New York in the same class with rapper Method Man and Carlsbad, California, where he attended Carlsbad High School. Masekela is the co-founder of Berkela Motion Pictures with Jason Bergh. When he was a teenager, Masekela's upbringing brought him to Southern California, where he was first exposed to surfing, snowboarding and skateboarding. From April 2016, Masekela appeared as the host and executive producer of VICELAND’s docu-series, VICE World of Sports. The series took viewers all over the world to explore each location's people, politics and culture through sports. The series premiere at the Tribeca Film Festival on April 22. Masekela is also involved in the production company UX Entertainment. Based in Los Angeles, UXE specializes in film, commercials, music videos and animation work.