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 Asmeret Ghebremichael as Renee Katherine Laheen as Ingrid Yair Ben-Dor as Javi Kim Blanck as Taylor Tracy Sallows as Skeptical Landlord #2 Eric Elizaga as Exec #1 Raphael Corkhill as Founder #4 Oge Agulué as Founder #3 Eric R. Williams as Cryo Attendant Frank Ridley as Skeptical Landlord #1 James Clow as Doorman Rishan Dhamija as Founder #1 Lyman Chen as Skeptical Landlord #3 Darryl McDaniels as Himself Tracy Weiler as Upper East Side Mom (Nicole) Zoe Zien as Journalist Dipti Mehta as Founder #2 David F.M. Vaughn as Photographer Vivienne Jurado as Accountant #1 Holly Anne Frink as Holly Bryan Robert Harlow Bintliff as Bryan
