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