In 1993, he set up his own record label, Bad Boy Entertainment, with talent from Uptown – such as then-newcomer, now-rap-royalty The Notorious B.I.G – helping the label take off. Twelve years, three Grammys, and two name changes later, “Diddy” was introduced to up-and-coming singer-songwriter Cassie, when she was 19 and he was 37. Diddy collaborated with Cassie shortly afterwards, in 2006, and the pair officially dated between 2012 and 2018.
