Woods started rapping as a child with friends using instrumentals for background music. After graduating high school, he attended Robert Morris University as an athlete and grew his passion for rapping. Woods became serious about rap when he met another musician who created and distributed his own mixtapes. He wanted to pursue music and began writing and rapping under the name Kev Tha Hustla.
In 2004, he met fellow Pittsburgh, Pennsylvania rapper Wiz Khalifa, through Pennsylvania producers I.D. Labs, who collaborated with Khalifa. Woods and Khalifa formed a partnership, which led to the formation of the group Taylor Gang in 2008. Woods released two mixtapes, The Corner's Correspondent in 2008 and Animal in 2009. His first two mixtapes featured collaborations with Wiz Khalifa, Boaz and members of Heavy Hustle Records. Production was primarily handled by I.D. Labs and Sledgren. In September 2010, Woods released his third official mixtape Pilot Shit.
In February 2011, Wiz Khalifa released his ninth mixtape, Cabin Fever, which featured Woods on three tracks, including "Taylor Gang", "Middle of You" and "Homicide". Woods released his fourth mixtape Red Cup Music, which featured guest appearances by Juicy J, French Montana, and production by ID Labs and Mac Miller in March 2011. Woods told MTV, the Red Cup Music was "really when I found a style for myself, some laid-back, cool music. Drink a little bit, smoke a little bit." Khalifa released the music video for the Lex Luger-produced track "Taylor Gang" in April 2011, which became an iTunes bonus track on Khalifa's debut studio album Rolling Papers. The song peaked at number 22 on the Billboard Bubbling Under Hot 100 Singles chart. In April 2013, Khalifa went on tour in support of Rolling Papers with Woods and Big Sean. This tour introduced Woods to Khalifa's mainstream audience. In August 2011, Woods released a mixtape, titled The Cookout, which featured Wiz Khalifa.

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