Polly Draper Sally Director, Actor, Screenwriter, Producer Nat Wolff Jack Actor Alex Wolff Oliver Actor Paulina Singer Violet Actor Nick Sandow Ron Actor Julia Macchio Caitlin Actor Julia Abueva Cassandra Actor Leo Heller Shark Boy Actor Ken H. Keller Producer Caron Rudner Producer Bill Draper Executive Producer Tim Draper Executive Producer Fred Roos Executive Producer David Kimelman Cinematographer Frank Reynolds Film Editing