Kira gets to gab with and then grill her former boss from The Tonight Show with Jay Leno, Jack Coen. A father of two, Jack talks about his early years as a comic, television writer, and then ultimately landing the coveted head writer and producer position during one of the most controversial late night debacles in television history. Jack is surprisingly candid with Kira while he compliments her work at the Tonight Show and then casually admits some regrets he has during his tenure there. How does Jack go from corner office at The Tonight Show to cornering bookers for stand up spots in the club? It's a great episode where Kira learns a lot about the business, parenting all while getting the closure she needs.