He began touring in support of "Transitions", which led to appearances at notable venues such as Sarasota Blues Fest in Sarasota, Florida; Skippers Smokehouse in Tampa, Florida, and slowly built his way to headlining or co-headlining appearances at House of Blues in Orlando, Florida, on The Waterfront in Rockford, Illinois, and Cultural Fest in Las Vegas. His second CD, "Blues Power", was released in fall of 2006. Looking to expand his musical horizons, Sears taught himself how to play over 20 instruments and learned the technical side of music production. In late 2006, Sears moved to the Southern soul genre with the release of his third album, "Southern Soul, Florida Style," a collection of blues and Southern soul songs that gained little exposure or radio play despite the lead single "Back That Thang Up" finding its way on some radio playlists and club reports. 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. Despite his often suggestive lyrics and racy concert performances which was deemed too explicit for commercial audiences, he became an underground success across the South and audiences, especially female ones, flocked to see Sears in concert. His fourth album was released in mid-2007 with the lead single "Dip My Dipper" faring well. In 2007, he served as musical director and lead guitarist for Miami soul singer David Hudson as well as guitarist/bassist and musical director for The Soul Generals while recording his fifth CD, his would-be major label debut "Sweet Thang", which was ultimately shelved in 2009 and remains unreleased. By the end of the year Sears went on hiatus from music at age 16 after personal problems arose. After a bout of depression and an attempted suicide, he turned his life over to God and began to do shows again, editing the lyrics to many of his songs and considerably cleaning up his stage show. The next few years went by with a few singles and some sporadic tour dates on the Chittlin' circuit. In 2010, Sears won a Soul Patrol "best of" in the Slow Jam category for his digital-single "You Betrayed Me". 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. Sears was nominated for Soul Blues Music Award for "Best New Artist". 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.