It was founded in 2009 by Michael Okwudili Ajakwe Jr and was one of the first web series-based events; Filmmaker Magazine called it "the granddaddy of all webfests.

When asked about the importance of web series as a creative medium by Carolyn Handler Miller for her book Digital Storytelling: A Creator's Guide to Interactive Entertainment, founder Michael Ajakwe, Jr. said: Before, filmmaking was a rich man's game.

In 2015, after other LA-based web series festivals scheduled their events around the same time (including the HollyWeb Festival and Indie Series Awards), Ajakwe came under fire for enforcing an 'exclusivity clause' stating that all entrants "must withdraw their shows from HollyWeb Fest and their award consideration at the ISAs, or be disqualified from LA WebFest.

"[3] The clause has since been the subject of controversy and derision in the web series community, with many calling it "anticompetitive" and "unreasonable.

[2] The Daily Dot also published a story about the controversy, writing: "The battle lines are drawn in the emerging web fest world, as the venerable LA Web Fest has drawn an exclusivity line in the sand for its 2015 entrants.