King and Lightnin' Hopkins as well as the soul, rock and funk music his parents would play,[2] he got started after his father purchased for him a Lonnie Mack CD[10] and he began taking guitar seriously at age 11 after a cousin turned him onto Jimi Hendrix.

Sears began sitting in with local bands and soon began appearing with Hubert Sumlin, Ronnie Baker Brooks (once referring to Sears as a "young Rico Suave"),[6] Guitar Shorty, Bob Margolin, Chris Beard, Ana Popović, Michael Burks, G. Love and Special Sauce, Fruteland Jackson, Lil' Ed Williams, Charlie Musselwhite, Bobby Rush, Inner Circle, Henry Gray, John Primer, Jimmy "Bo" Horne, Pinetop Perkins, backed up The Temptations,[11] and even appeared with Rock and Roll Hall of Fame inductee Solomon Burke who dubbed Sears "the future [of Soul and Blues]" and referred to him as "godson".

[12][13] In early 2004 Sears assembled a band of veteran musicians and he began booking shows at local clubs and festivals on the weekends and developed a loyal fan base and attracted the attention of several independent labels.

[12] Sears' national debut album Transitions, a jazz-rock influenced collection of classic and obscure blues covers was released in September 2005.

Sears slowly built a strong fan base in the Southern soul market by tirelessly touring the south's Chitlin circuit of rural juke joints, ghetto bars, and blues festivals.

[18] In November of that year he released his most successful single to date "Dirty Dancer" which fared well on the Southern soul charts, hitting number one in several markets.

[20] Sears began to embrace the neo-soul and urban Adult Contemporary Rhythm and Blues (R&B) sound with the release of the low-profile single "Can't Get You Out of My System" in early 2011.