The premiere episode features Michelle Smalls (aka Queen of Harlem), an author and real estate broker, Smalls owns several businesses including a spa, a juice bar, and a real estate firm. The second episode follows criminal defense attorney Dawn Florio, known for her high-profile celebrity clients, including Tekashi 6ix9ine and Lil Tjay. In the final three episodes, Dash is joined by Steve Mack, his childhood friend from Harlem who has worked closely with him on his business and media ventures, including Beat 139 and Roc-A-Fella Records.