Guest Stars Daniel K. Isaac as Ben Kim Dhruv Maheshwari as Tuk Lal Louis Cancelmi as Victor Mateo Will Roland as Winston Eva Victor as Rian Toney Goins as Philip Charyn Jade Eshete as Lauren Turner Matt Servitto as Bob Sweeney Wendie Malick as Leah Calder Chris Eigeman as Stuart Legere Kevin Chapman as Tony Plimpton Okieriete Onaodowan as Leon Sherald Co Starring Kira Visser as Donna Lilly Moran as Peach Susan Blackwell as Kristy Adam Grant as Himself Neil Blumenthal as Himself Mariette Booth as Sarah Gallagher David Einhorn as Himself Seth Godin as Himself Jacqueline Novogratz as Herself