Guest Stars Anthony Edwards as Bruce Dunlevie Theo Stockman as Jacob Cricket Brown as Chloe Morgan Andrew Burnap as Phil Troy Iwata as Damian Saito 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 Isabel Joy Wolk as Ahava Lily Jane as Harlow Moon Lio Mehiel as Birdie Asmeret Ghebremichael as Renee Katherine Laheen as Ingrid Bianca Norwood as Ryan Annie Fox as Esther Yair Ben-Dor as Javi Alexandra Foucard as Secretary Adam Heller as Frankel Jonathan Spivey as Nosey Pedestrian Kelly Nash as CNBC Reporter Daniel Hepner as Chris (PR Flack #1) Richard Dubin as Board Member #4 David Becker as Himself Sho Suzuki as Board Member #5 Nathan Min as Robb Ashton Heyl as Siobhan Cole Francum as Director Mark Quiles as Mr. Fishman Edward Watts as Keegan / Parent #1 Scottie DiGiacomo as Board Member #3 Wren Rivera as Damian's Assistant Josephine Huang as PR Flack #2 Hannah Jane McMurray as Monica Michael Hartney as Will / Parent #2 Pat Labez as Claudia Koh Mochizuki as Marcus Tristan Griffin as PR Flack #3
