This talk is a short anabasis of someone who uses functional programming to break, rather than build, software. This talk will cover how a college dropout uses languages such as OCaml, Scala, and F# to do digital forensics, reverse engineer IoT firmware, and perform penetration tests on networks and websites alike. Additionally, we will close on ideas on how to use functional programming in modeling architecture, to allow for a more programmatic and logical approach to assessing risk for businesses and systems alike. No specific programming language is assumed, as this talk will wander, Greek-like, across the landscape of breaking and building. Our quest is to explore where functional programming can take an industry not used to formal analysis, and more likely to adopt anarchistic "hacks."