After releasing "The First Flight" in December 2009, Diggy Simmons created his first mixtape with zero assistance from his family members, who many consider to be hip-hop royalty, but rather solely through networking via the internet and his personal blog. The first single from the project was "Point to Prove," a song which sees the young rapper expressing his struggle to prove to the world that he is his own person, and strives to establish himself as more than just the rapping son of Rev. Run or nephew of Russell Simmons. He followed his much-talked about BET Hip Hop Awards Cipher, alongside his father and brother, JoJo Simmons, with the release of his third mixtape in 2 years, "Past, Present (s) Future." Diggy received the ultimate co-sign in April 2011, when XXL Magazine featured him in their "Freshman Class" issue, an issue dedicated solely to the stand out artists who the publication believes have made a strong impact, and have the potential to take this buzz into a concrete placement in the hip-hop world.