In Chapter 13 of 14 in his 2009 Capture Your Flag interview, comedian Matt Ruby reflects on lessons learned over first four years performing stand-up and its impact on his style. From early characters, including Mortimer the Steel Baron, improv work, and clever one-liner jokes, Ruby traces transition to longer form, more genuine topics that carry a big payoff to win an audience. Ruby highlights collective audience wisdom and what he has learned about more effectively presenting ideas honestly and openly to engage a room and earn respect while honing his craft.