He continued his studies with trumpeters Tommy Turrentine and Bill Hardman, as well as attending Barry Harris's jazz classes.

Eventually leading an "after hours" session for Harris, he performed with such musicians as Stephen Scott, Winard Harper, Leon Parker, Sam Newsome, Justin Robinson, Rodney Kendrick, Roy Hargrove, Clifford Jordan, Mulgrew Miller, Jeff Watts, Terence Blanchard, Benny Green, and Billy Hart.

The rest of the band rotated: Benny Green, Stephen Scott, or Dave Kikoski on piano, Christian McBride on bass, and Billy Hart or Jeff Watts on drums.

From there, he began arranging for such artists as Abbey Lincoln, Freddie Hubbard, and Rodney Kendrick, Alto Legacy with Phil Woods, Vincent Herring, and Antonio Hart.

"[2] Weiss's compositions on the Octet's second album won him grants from Chamber Music America and Doris Duke Jazz Ensembles Project: New Works Creation and Presentation.