[2] Living in a fatherless household, he watched as his mother work three jobs and still struggle to support him along with his brother and sister.
His song "Letter to My Son" (originally released in 2009), went semi-viral on YouTube, fueling his transition toward mainstream hip-hop.
[9] The song, which detailed Trip's struggle with being unable to see his son due to a court ruling, was lauded for its accurate depiction of a hardship not often portrayed in rap music.
In 2012, hot on the heels of "Letter to My Son," Trip was named one of XXL's 2012 freshmen, alongside artists including Future, Danny Brown, and Hopsin.
[12] Released in 2011, the mixtape was peppered with references and in-jokes relating to the Judd Apatow movie Step Brothers, and gained a cult following among the rap community.
[17] Released independently, like the two previous mixtapes, Step Brothers 3 received widespread critical acclaim from publications such as Pitchfork,[18] XXL,[19] and USA Today.