Interested in entertainment and storytelling at a young age, Jacob Estes began writing short stories and acting in school plays while a grammar school student in Chicago. His first role was as Captain Hook in a musical version of Peter Pan. He went on to study acting at The Young Conservatory Theater at A.C.T. and improvisation at The Second City of Chicago.
While attending the University of California at Santa Cruz, Estes earned The Dean's Award for the Arts for the script and production of his one-act play Leigh's Outrunning Her Mefa and Pefa Tonight. He went on to earn a Master's Degree in Film Directing at The American Film Institute, where he wrote and directed three short films including his thesis, Summoning (2001).
Estes made his feature film screenwriting and directorial debut with Mean Creek (2004), for which he won the prestigious Nicholl Fellowship in Screenwriting. The film also won the Humanitas Prize at the 2004 Sundance Film Festival.