In the 21st episode, Connor speaks with Survivor legend Boston Rob, aka Rob Mariano, about growing up near Fenway Park, learning poker at the age of 6, studying psychology at Boston University, applying for Survivor and winning Season 22, his recent appearance on Deal or No Deal Island and filming an upcoming season of Traitors.

Boston Rob also revealed a story about Costa Rica authorities raiding a 2006 poker game at gambling mogul Calvin Ayre's mansion that included Daniel Negreanu, Josh Arieh, David Williams, Michael Mizrachi and actress Cheryl Hines.