Kelly Leonard has been working with the famous Chicago Improv theater Second City for nearly three decades. He is considered a major force behind the “renaissance and expansion” of Second City and it’s alumni’s current dominance of late night television. Famous alums include Tina Fey, Seth Meyers, Stephen Colbert and more. Today, Leonard is running Kelly Leonard Productions, an entity housed within the Second City umbrella. He also recently wrote a book exploring how the Second City methodology can be applied to business. He joins Jeffrey to discuss improv & business, what he learned from Tina Fey and more on this episode.