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 Campbell Scott as Jamie Dimon Mallori Johnson as Bea Alex Vinh as Mikey Kim Eui Sung as Masayoshi Son America Ferrera as Elishia Kennedy Jordan Bridges as Jamie Hodari Christopher Livingston as Jonathan Mildenhall Co Starring Robert Emmet Lunney as Richard / Board Member Tom Galantich as Carl / Board Member Isabel Joy Wolk as Ahava Asmeret Ghebremichael as Renee David Ebert as WeWork Exec 1 / Jeff Winitsky Megan Masako Haley as PR Exec Di Zhu as Chinese Translator Brandon Contreras as Personal Banker Karoline Xu as Vanity Fair Journalist Pomme Koch as Muhammad Katherine Stinnett as PR Assistant #1 John Manno as Vanity Fair Photographer Dylan Wallach as Hodari Lookalike Alicia Mitchell-Mangual as Bank Teller Matt Wolpe as Schlubby Engineer David Niu as Chinese Contractor Edward Furs as Polish Contractor Erica Sinner as Cassandra Chris Bolan as Paparazzo #2 Richard Lyntton as French Project Manager Jason Ostrowski as Myles Tyler Jones as WeWork Tour Guide Lizzy Jutila as Paparazzo #1 Q-Tip as Himself Irene Rising as Makeup Artist Jeanette Villafane as Paparazzo #3