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