Jacob Ashley is a Chicago native who began his formal dance training in 2002 at the Chicago Academy for the Arts under the instruction of Randy Duncan, Guillermo Leyva, Sandra Kaufmann, and the late Anna Paskevska. In 2006, he attended Columbia College Chicago's modern dance program under the direction of Margi Cole, Jeff Hancock, Carrie Hanson, and Emily Stein. He later on became an apprentice for Gus Giordano Dance and Luna Negra Dance Theater. He also attended Ballet Chicago's summer program under the intense training of Daniel Duel and Patricia Blair. Jacob has been a guest artist for such companies as, the West Indian Folk Dance Company, Momenta, Ballet Chicago, Chicago Festival Ballet, Dallas Opera, Houston Grand Opera, Les Ballet Grandiva, Madison Ballet, Lyric Opera of Chicago, Joffrey Ballet of Chicago, and San Diego Opera.