Bootstrap held its first Bootstrap Film Fest on June 26, 2008 (pictures on facebook). Five films by Bootstrap Film members were featured: Little Dove, Open House, Snake Pit, Art Erotica and Mystic Cab. Bootstrap member, BSide powered the film fest website.

The BootRap Podcast includes an introduction by Bootstrap Film Subgroup lead, Brandy Rainey Amstel and a dialogue with the filmmakers: Nils Juul-Hansen (Mystic Cab - director), Jason Howell (Art Erotica), James Mays (Mystic Cab - actor) and Bijoy Goswami (Mystic Cab - writer/actor).

The bootstrap filmmakers share their stories of bootstrapping their films, leveraging social capital with an effective value 10x more than the cash budget, how constraint creates innovation, demo/sell/build, the difference between a "bootstrapper who makes films" vs a "filmmaker who bootstraps," bootstrap vs indie filmmaking, stages of bootstrap, and distribution.