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 Mallori Johnson as Bea Kim Eui Sung as Masayoshi Son Co Starring Robert Emmet Lunney as Richard / Board Member Tom Galantich as Carl / Board Member Lily Jane as Harlow Moon Lio Mehiel as Birdie Isabel Joy Wolk as Ahava Katherine Laheen as Ingrid Kate Villanova as CNBC Interviewer #1 Alexandra Templer as Team Member Yoshiro Kono as Vision Fund Exec #2 Essam Ferris as Mubarak Vasile Flutur as Bjarke Ingels Becky Gulsvig as Education Consultant Candy Buckley as Headmistress Tatsuo Ichikawa as Vision Fund Exec #1 Don Guillory as Lewis MK Haresign as Vision Fund Lawyer Cameron Anika Hill as First Grade Teacher Angelica Toledo as Marketing Exec #1 Darrell Morris Jr. as Marketing Exec #2