He released his first single "Speed Star" in 2006 and promoted the title track, "Motivation", on the SBS variety show The Truth Game.

Outsider has worked with underground and overground rappers such as MC Sniper, L.E.O, Illnit, DJ R2, Bae Chi Gi, Dok2, and more.

He was also featured on a charity single entitled "Faddy Robot Foundation" with Vasco, Verbal Jint, Sangchu, Yong Junhyung, Joosuc, Hyuna, and Zico.

On October 21, 2010, he released his 3rd album titled "Hero" along with two singles; "주인공 (Hero)" featuring fellow label-mate, LMNOP, and "Attitude Needed When Breaking Up" (이별할 때 필요한 자세) featuring fellow hip-hop artist, Kuan of All That.

On December 21, 2010, Outsider enlisted for mandatory military service for five weeks of basic training followed by 21 months of active duty in Wonju.

[12] In a press release, Outsider claimed he never received proper pay or credit for his various activities and copyrights.

Sniper Sound in turn filed an opposing lawsuit against Outsider calling him to halt his recent activities.

His wife, Lee Yongbin (이영빈) is director of a dance troupe as well as the CEO of a cultural contents enterprise.