William Kaiser is a sociologist, a pupil of Peter Berger, a student of the philosophy of Wittgenstein, and an autodidact in all things Freud, Nietzsche & Kaufmann. His dissertation on the topic of Wittgenstein was entitled, "A Wittgensteinian Critique of Realism in Social Science Methodology", and to this day, Kaiser maintains his skepticism towards what he characterizes as "naive realism". He expresses the common thread he sees in many philosophers, from Nietzsche, to Rorty, to Wittgenstein himself: rejection of the idea of obtaining some sort of objective knowledge and the re-centering of our philosophical orientation on the human psyche. All these figures cut through abstruse confusions to reach concrete insights about history and the human condition. Central to this project for Wittgenstein (especially Later Wittgenstein, aka "Wittgenstein II", who was Kaiser's focus in his work) is the way in which language shapes human thought. Through this conversation, we discuss the commonality between Nietzsche's ideas and Wittgensteins, on the issues of language, on memory and forgetting, self-identity, and what it means to learn and live an enriching life. We also spend some time discussing Freud and the influence Nietzsche had on the famous Viennese psychoanalyst.