Complex sentence: He signed his first deal in 1998 with Tommy Boy Records, after the label shut down, he signed a deal with Columbia where he started recording an album called "Rock City", referring to Detroit's former status as home to Motown Records.
Split into simpler sentences: He signed his first deal in 1998 with Tommy Boy Records. After the label shut down, he signed a deal with Columbia where he started recording an album called "Rock City", referring to Detroit's former status as home to Motown Records.