For 20 years, Jacobson was a founding partner of management firm James/Levy/Jacobson. Working alongside his partners, Jacobson was involved in launching the careers of such actors as James and Dave Franco, Jennie Garth, Jaimie Alexander, Michelle Williams, Mark-Paul Gosselaar, Mena Suvari and Erika Christensen. He signed Hilary Swank when she was 15, represented her for 10 years and helped her get Boys Don’t Cry, which earned her an Oscar. He also signed Ben Foster at the age of 12 and repped him for 20 years.
Jacobson’s career started in 1975 as an actor. For 10 years he appeared in theater in New York, including playing the role of David in the 1983 Tony Award-winning play Torch Song Trilogy.