Guest Stars Sonny Valicenti as Matt Cohler Darren Pettie as Hendricks Mousa Kraish as Fawzi Kamel Noah Weisberg as Quentin Joel Kelley Dauten as Ryan Graves Rama Vallury as Tahir Khan Damon Gupton as David Drummond Virginia Kull as Jill Hazelbaker Amanda Brooks as Rachel Whetstone Erinn Ruth as Olivia Lungociu Chelcie Ross as David Bonderman Eva Victor as Susan Fowler Mark Gessner as Gil Jeremy Howard as Anthony Levandowski Rob Morrow as Eddy Cue David Krumholtz as Sergey Brin Adam Daveline as Craig Lily Rains as Anne-Marie Co Starring Quentin Tarantino voices Tarantino's Voice Amel Khalil as Zahra Kamel Kate Amundsen as Kelsey Joy Corrigan as Woman 1 Kyle Louis as Pete Anna MacDonald as Woman 2 Jared Wernick as Tre Ray Huizar as Brazilian Uber Driver Gabriel Sousa as Brazilian Teenage Boy Kevin Markovic as Kev Olivia Baptista as Brazilian Teenage Girl Brian Sacca as Chris Sacca Andrew Grace as Shane Dean Li as Ant Marc Jablon as Event Facilitator