Jacolby is a multimedia artist, born in Columbia, South Carolina. He received his MFA from the University of Pennsylvania, and his BFA from Maryland Institute College of Art. He's participated in residencies at Skowhegan School for Painting and Sculpture, Headlands Center for the Arts, and the Center for Photography at Woodstock. His work has been included in group exhibitions and performances at Exit Art, Rush Arts Gallery, The Kitchen, MoMA PS1, The Studio Museum of Harlem and the Smithsonian Institution. Jacolby is a recipient of the Van Lier Grant, the Experimental TV Center NYSCA Grant, and the Toby Devan Lewis Award.