Guest Stars Anthony Edwards as Bruce Dunlevie Theo Stockman as Jacob Andrew Burnap as Phil Troy Iwata as Damian Saito Cricket Brown as Chloe Morgan 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 Lily Jane as Harlow Moon Isabel Joy Wolk as Ahava Bill Winkler as Morgan Master of the Universe Joshua Wills as Eliot Brown Adi Hanash as Caleb Anthony R. Mottola as Mikey's Friend Ryan McCarthy as Jason / Goldman Sachs Managing Director Jessica Cummings as Claire William Ragsdale as Chris Go Eun Ryu as Gallerist Madsie Flynn as WeGrow Teacher #1 Shawn K. Jain as Lee Tiffany Green as WeGrow Teacher #2 John Anderson as Podcast Host Ellen Harvey as Goldman Master of the Universe
