Guest Stars Anthony Edwards as Bruce Dunlevie Theo Stockman as Jacob Troy Iwata as Damian Saito Cricket Brown as Chloe Morgan Andrew Burnap as Phil O.T. Fagbenle as Cameron Lautner Steven Boyer as Matthew Campbell Scott as Jamie Dimon Kim Eui Sung as Masayoshi Son Alex Vinh as Mikey Kate Jennings Grant as Emily Raubvogel Co Starring Robert Emmet Lunney as Richard / Board Member Tom Galantich as Carl / Board Member Lio Mehiel as Birdie Lily Jane as Harlow Moon Isabel Joy Wolk as Ahava Asmeret Ghebremichael as Renee Katherine Laheen as Ingrid Bianca Norwood as Ryan Annie Fox as Esther Alexandra Foucard as Secretary Yair Ben-Dor as Javi Adam Heller as Frankel Jonathan Spivey as Nosey Pedestrian David Becker as Himself Daniel Hepner as Chris (PR Flack #1) Edward Watts as Keegan / Parent #1 Hannah Jane McMurray as Monica Mark Quiles as Mr. Fishman Cole Francum as Director Ashton Heyl as Siobhan Nathan Min as Robb Sho Suzuki as Board Member #5 Richard Dubin as Board Member #4 Scottie DiGiacomo as Board Member #3 Wren Rivera as Damian's Assistant Kelly Nash as CNBC Reporter Koh Mochizuki as Marcus Tristan Griffin as PR Flack #3 Pat Labez as Claudia Josephine Huang as PR Flack #2 Michael Hartney as Will / Parent #2
