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 Raphael Corkhill as Founder #4 Eric R. Williams as Cryo Attendant James Clow as Doorman Kim Blanck as Taylor Darryl McDaniels as Himself Lyman Chen as Skeptical Landlord #3 Bryan Robert Harlow Bintliff as Bryan Vivienne Jurado as Accountant #1 David F.M. Vaughn as Photographer 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 Tracy Sallows as Skeptical Landlord #2 Frank Ridley as Skeptical Landlord #1
