[3] Following his family's relocation to California in 1976, Jacobs – like his older siblings Christian and Rachel and younger brother Tyler – worked as a child actor, appearing in numerous commercials and television shows in his preadolescence.

[1][4] His most notable acting work included a starring role on the sitcom The Cavanaughs, in which he appeared in every episode during the series' run from 1986 to 1989, and as the recurring character "Purdle the Turtle" on The Wonder Years.

[3] Upon his return, he moved back to California and became involved with his brother Christian's then-up-and-coming band The Aquabats, providing artwork for their logos, albums and merchandise, as well as contributing lyrics, various creative ideas and running their fan club.

[5][7][8] Most visibly, however, Jacobs played the role of "The Professor" in The Aquabats' music videos and stage shows, taking part in the band's onstage skits and occasionally supplying backing vocals.

In 2007, the series was picked up by Viacom's Nick Jr. Channel, prompting Jacobs to leave his job at Paul Frank to work full-time on the show.