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 Mallori Johnson as Bea Alex Vinh as Mikey Kelly AuCoin as Scott Galloway Co Starring Robert Emmet Lunney as Richard / Board Member Tom Galantich as Carl / Board Member Lio Mehiel as Birdie Isabel Joy Wolk as Ahava Lily Jane as Harlow Moon William Ragsdale as Chris Anthony R. Mottola as Mikey's Friend Bill Winkler as Morgan Master of the Universe Ellen Harvey as Goldman Master of the Universe Go Eun Ryu as Gallerist Shawn K. Jain as Lee Madsie Flynn as WeGrow Teacher #1 Jessica Cummings as Claire Joshua Wills as Eliot Brown Tiffany Green as WeGrow Teacher #2 John Anderson as Podcast Host Ryan McCarthy as Jason / Goldman Sachs Managing Director Adi Hanash as Caleb
