Maino was incarcerated for 10 years on kidnapping charges, and was released in 2003. During his incarceration he was cut on the right side of his face with a razor which left him with a scar. He began to write music while in prison.
After several mixtape releases and key guest features, Maino was offered a recording contract by Universal Records. Maino split with the label in 2007, feeling that the label wasn't promoting him enough. He later signed with himself and his Hustle Hard imprint to Atlantic Records. His first single from his debut album If Tomorrow Comes is "Hi Hater." Maino released the official remix to the song, featuring T.I., Swizz Beatz, Plies, Jadakiss, and Fabolous. The next single was "All the Above," featuring T-Pain, then "Million Bucks," produced by and featuring Swizz Beatz.
On January 26, 2010, Maino released Unstoppable - EP onto iTunes which featured four new recordings. On February 9, 2010, Funkmaster Flex premiered the first single off The Day After Tomorrow titled "Bring It Back DJ" on Hot 97.
In October 2008, Maino went public with news that he smacked Yung Berg in an Atlanta nightclub. Maino claimed that Berg’s “disrespectful” ways and "body language" led him to do “God’s work.”