Guest Stars Ben Feldman as Ron LaFlamme Henry Phillips as John Stafford Emily Chang as Herself Kara Swisher as Herself Joel Swetow as Rod Morgenstern Dick Costolo as Himself Conan O'Brien as Himself Samantha Cutaran as Woman in Pied Piper Ad #2 Jason Sims-Prewitt as Jim Gittman Leanne Suter as KTUY3 Female News Anchor Alec Berg as Documentarian Yonas Kibreab as Boy in the Jungle Bill Gates as Himself Cinda Adams as Woman in Pied Piper Ad #3 Richard Wharton as Man in Pied Piper Ad #2 Rick Chambers as KCYD News Anchor Lavelle Roby as Old Woman in Pied Piper Ad Alfred Rubin Thompson as Man in Pied Piper Ad #1 Jim Cramer as Himself Julianne Buescher as Debbie Judith Drake as Judy Jaidyn-Bleau as Girl in Pied Piper Ad Robert M. Lee as Man in Pied Piper Ad #3 Julia Finkelstein as Young Woman Drake Hansen as Boy in Pied Piper Ad Jay Jackson as KTUY3 Male News Anchor