After working for Kaizer Chiefs Football Club as a video producer and director; Gregory decided to venture on his own and establish Worthy Media. The transition was tough, but with great resilience and sharp wit; Worthy Media developed their first production for DSTV titled, Rap Dads. A reality show developed in partnership with popular musician, JR Bogopa. With that beginning, the rest was history. ​ Over the past 20 years Gregory has produced and directed for clients such as; SABC 1, E-TV; Mzansi Magic, Vuzu Amp, Channel O, Ster-Kinekor, Nu-Metro, Supersport, Kaizer Chiefs, MTN, Amazon Prime Video, Virgin Money.