Stein's eventual absorption with jazz was an evolutionary process rather than the product of a defining moment or two. It wasn't until his teens that he started noticing jazz. The genre completely enveloped him at the age of 30, when he became a student at Berklee College of Music in Boston where he later became a member of the faculty. He sees the music as a constant challenge to further hone his performing and composing skills and techniques.

During the developmental process, Stein was influenced by several jazz artists, both guitarists and other instrumentalists, including Wes Montgomery, Jim Hall, Hank Mobley, and Bill Evans. The guitarist has four albums as a leader, two of which are for a leading European label, Jardis. Both of these CDs, the 2000 release Portraits and Landscapes and the 2002 album, Conversation Pieces, are dominated by Stein compositions, pieces which are characterized by their diverse melodic and harmonic structures. Stein has managed to avoid the deep, dark hole of routine and repetition. The latter album is also an occasion for a revisit by longtime Ray Charles' tenor sax player David "Fathead" Newman. Newman also appeared on Stein's 1999 CD Green Street. Stein is also featured on Ron Gill's album Ron Gill Sings the Songs of Billy Strayhorn, which was released in December 1997 by Boston's WGBH Radio. The guitarist has also appeared at festivals and concerts such as the Boston Globe Jazz Festival and New Orleans' Funky Butt jazz clam bake. When Stein isn't recording, performing, or teaching, he enjoys listening to guitar and bass duets, especially Jim Hall in a guitar/bass context, and other artists such as Art Tatum, Stan Getz, and Antonio Carlos Jobim. ~ Dave Nathan