Returning to the Philippines in 2005, Milby decided to seriously pursue a career in show business and modeling. He landed bit roles in some ads before obtaining a lead role in Close Up's TV commercial with Barbie Almalbis. He subsequently joined Pinoy Big Brother, which featured 12 men and women from different walks of life; Milby was not one of the original 12, but joined the cast when one of the contestants left the house. After this, he became into an actor and recording artist and signed up a contract with ABS-CBN. His first major film debut was Close to You, produced by ABS-CBN subsidiary Star Cinema and co-starring John Lloyd Cruz and Bea Alonzo.