A native of Berkeley, California, Jekabson played music from an early age, eventually settling on the trumpet at age ten. By his teens Jekabson's playing landed him a spot touring Japan with the Monterey Jazz Festival High School All-Star Big Band in 1991. After high school he studied jazz at the prestigious Oberlin Conservatory of Music in Ohio, where was able to tour the United States in promotion of Oberlin's jazz program. Graduating in 1994, Jekabson moved to New Orleans and found himself performing with such varied artists as trumpeter Kermit Ruffins, organist Eddy Louiss, and the jazz-funk group Galactic. A move to New York City in 1998 brought Jekabson work with an eclectic group of musicians including the Howard Fishman Quartet and the Illinois Jacquet Big Band as well as gigs with his own post-bop-oriented ensemble, Vista. In 2003, Jekabson enrolled in the San Francisco Conservatory of Music's graduate program for composition. While active in the San Francisco music scene, Jekabson could also be found touring with singer/songwriter John Mayer. In 2010, he released the album Crescent Boulevard. In 2012, Jekabson returned with the album Anti-Mass, featuring his arrangements for his small, string-based chamber jazz ensemble, the String-tet. The concert album Live at the Hillside Club, featuring Jekabson performing with his quartet and percussionist John Santos, appeared in 2014. Two years later, the trumpeter returned with the nuanced, post-bop-inflected A Brand New Take. ~ Matt Collar