Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Molly Jong-Fast as Herself Lisa Rubin as Herself Symone Sanders-Townsend as Herself Vaughn Hillyard as Himself Dominic Chu as Himself Raf Sanchez as Himself Jen Psaki as Herself Barbara McQuade as Herself Andrew Weissmann as Himself George Conway as Himself Wes Moore as Himself (Gov. Wes Moore) Morgan Chesky as Himself Patrick Healy as Himself Arthur C. Brooks as Himself Ken Block as Himself Adam Grant as Himself Frank Kendall as Himself Ali Arouzi as Himself
