After forging a long-time friendship with Wayne, Lilly signed with his label Young Money Entertainment, and later Republic Records.

On May 26, 2009, Gudda released Certified a collaboration album with fellow rapper Lil Flip on Real Talk Entertainment.

His second official mixtape featured guest appearances from Waka Flocka Flame, Mack Maine, Jay Rock, Lil Wayne, Vado, Ya Boy and Jae Millz, among others.

The tracklist revealed guest appearances from Wiz Khalifa, 2 Chainz, Lil Wayne, Mystikal, Crooked I, Trae tha Truth, Ace Hood, Future, Jae Millz, Birdman, Kevin Gates, Tyga, and Mack Maine.

[12] Around the time he formed the group Loyalty Amongst Thieves, featuring Kevin Gates, Flow and T-Streets, which he said planned to release a self-titled mixtape.

The mixtape featured guest appearances from Busta Rhymes, Jae Millz, Cory Gunz, Boo, and Charlie Rock among others.

[13] Additionally he revealed he was starting his own production company Gudda Music and the Loyalty Amongst Thieves mixtape had already been completed.

[4][13] Billboard praised his verse on Lil Wayne's I Am Not a Human Being II track "Gunwalk" as "show stealing".

[17] He was also featured on two tracks on the 2013 YMCMB compilation album Rich Gang, including "Panties To The Side" with Bow Wow, French Montana and Tyga.

[18] He confirmed guest appearances on Guddaville: The Album to come from Lil Wayne, Busta Rhymes, and Drake, while also saying his dream collaborations would be with Kool G Rap or Dr.