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