Guest Stars Anthony Edwards as Bruce Dunlevie Theo Stockman as Jacob Troy Iwata as Damian Saito Andrew Burnap as Phil Cricket Brown as Chloe Morgan O.T. Fagbenle as Cameron Lautner Steven Boyer as Matthew Kim Eui Sung as Masayoshi Son America Ferrera as Elishia Kennedy Antoinette Crowe-Legacy as Lesley Sasson Gabai as Doron Neumann Co Starring Robert Emmet Lunney as Richard / Board Member Onie Maceo Watlington as Harlow Moon Katherine Laheen as Ingrid Asmeret Ghebremichael as Renee Yair Ben-Dor as Javi Raphael Corkhill as Founder #4 Eric R. Williams as Cryo Attendant Kim Blanck as Taylor Darryl McDaniels as Himself David F.M. Vaughn as Photographer Bryan Robert Harlow Bintliff as Bryan Vivienne Jurado as Accountant #1 Holly Anne Frink as Holly Zoe Zien as Journalist Eric Elizaga as Exec #1 Rishan Dhamija as Founder #1 Tracy Weiler as Upper East Side Mom (Nicole) Oge Agulué as Founder #3 Dipti Mehta as Founder #2 Lyman Chen as Skeptical Landlord #3 James Clow as Doorman Tracy Sallows as Skeptical Landlord #2 Frank Ridley as Skeptical Landlord #1