Guest Stars Anthony Edwards as Bruce Dunlevie Theo Stockman as Jacob Andrew Burnap as Phil Troy Iwata as Damian Saito 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 Eric R. Williams as Cryo Attendant Raphael Corkhill as Founder #4 Frank Ridley as Skeptical Landlord #1 Tracy Sallows as Skeptical Landlord #2 James Clow as Doorman Kim Blanck as Taylor Rishan Dhamija as Founder #1 David F.M. Vaughn as Photographer Holly Anne Frink as Holly Lyman Chen as Skeptical Landlord #3 Darryl McDaniels as Himself Eric Elizaga as Exec #1 Dipti Mehta as Founder #2 Oge Agulué as Founder #3 Tracy Weiler as Upper East Side Mom (Nicole) Zoe Zien as Journalist Vivienne Jurado as Accountant #1 Bryan Robert Harlow Bintliff as Bryan
