Chuck Inglish, born Evan Ingersoll, was raised in Mount Clemens, Michigan until he moved to Chicago, Illinois after turning 18. Ingersoll attended Notre Dame High School in Harper Woods, Michigan where he played football and basketball. He met Sir Michael Rocks in 2005 when Reed found a beat on MySpace that Ingersoll had produced. The two met to discuss terms of the beat's sale, and eventually ended up recording for two hours. They were inspired by golden age hip hop and artists like LL Cool J and Eric B. & Rakim. Ingersoll began promoting the new duo's material, and it was eventually booked by Josh Young of Flosstradamus for a DJ performance. At their performance (in a venue called Town Hall Pub), the duo met the DJ Diplo who offered to release a mixtape of their unreleased tracks titled Totally Flossed Out on his label Mad Decent, though it was eventually released on C.A.K.E. Recordings. They also received an offer from the DJ A-Trak to sign to his Fool's Gold Records label, which they did, but only for one single. During their time with Fool's Gold Records, the Cool Kids felt they weren’t getting enough attention: “When your boss is on tour with Kanye West, it’s easy to have timelines missed,” said Chuck in an interview.
