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 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 Alexandra Foucard as Secretary Yair Ben-Dor as Javi Annie Fox as Esther Mark Quiles as Mr. Fishman Tristan Griffin as PR Flack #3 Jonathan Spivey as Nosey Pedestrian Josephine Huang as PR Flack #2 Daniel Hepner as Chris (PR Flack #1) Adam Heller as Frankel 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 Edward Watts as Keegan / Parent #1 Scottie DiGiacomo as Board Member #3 Wren Rivera as Damian's Assistant Hannah Jane McMurray as Monica Michael Hartney as Will / Parent #2 Pat Labez as Claudia Koh Mochizuki as Marcus Kelly Nash as CNBC Reporter
