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 Isabel Joy Wolk as Ahava Lily Jane as Harlow Moon Lio Mehiel as Birdie William Ragsdale as Chris Adi Hanash as Caleb Anthony R. Mottola as Mikey's Friend Ryan McCarthy as Jason / Goldman Sachs Managing Director Bill Winkler as Morgan Master of the Universe John Anderson as Podcast Host Go Eun Ryu as Gallerist Madsie Flynn as WeGrow Teacher #1 Shawn K. Jain as Lee Jessica Cummings as Claire Joshua Wills as Eliot Brown Tiffany Green as WeGrow Teacher #2 Ellen Harvey as Goldman Master of the Universe
