Crawford is CEO of 1501 Certified Entertainment, an independent record label based in Houston. In early 2018, the label signed hip-hop artist Megan Thee Stallion, who quickly rose to fame with a string of hit songs. All of her releases from 1501 Certified are now marketed by 300 Entertainment and distributed by Warner Music Group. In March 2020, several months after she signed a management deal with Roc Nation, Megan Thee Stallion sued 1501 Certified and Crawford, claiming they were blocking her from releasing music while refusing to renegotiate or terminate a contract she called "entirely unconscionable." In an interview with Billboard magazine, Crawford denied wrongdoing, insisted the contract was generous for a new musical act, and characterized the lawsuit as an attempt by Roc Nation to intimidate him into renegotiating.
