John and Ken begin the show by providing some background on Diogenes—the greatest ancient Cynic, as John puts it. Diogenes, Ken tells us, lived around 300 B.C.E. John starts the conversation by noting that based on how he acted, you would think he’s quite the jerk. Ken speaks of Diogenes in a different light, pointing out that he was a principled man, one who thought that philosophers should focus on the physical world and basic human needs. 

Explaining John’s concern about how Diogenes treated Alexander the Great and acted—publicly urinating, defecating, and masturbating—Ken explains that he was just living out his belief in the useless of arbitrary conventions. John, now in agreement that Diogenes was a principled philosopher, points out that now we use the word a bit differently.

The two are joined by Luis Navia, Professor of Philosophy at the New York Institute of Technology, and author of Diogenes the Cynic: The War Against the World. Navia shares that he was drawn to Diogenes perhaps by the touch of cynicism he himself has, viewing many things today as fundamentally detrimental to what he believes is the natural way of being human.Ken wonders how, if at all, Diogenes is able to reconcile what seems to be an inherent tension between Diogenes’ philosophy of radical individualism and Aristotle’s characterization of humans as necessarily social creatures. This seems to be an especially dubious part of his philosophy, adds John. Navia, in response to this, clarifies that unlike Plato and Aristotle, Diogenes was not a systematic philosopher, and often exaggerated his points to set a high bar. 

Yet, he was still committed to reason, and a part of the ancient school of philosophy. Drawing from Navia’s characterization, Ken distills the thought as such: for Diogenes, philosophy was not writing down thoughts and airtight arguments, but more performing and presenting them.

Guided by audience emails and phone calls, the three move on to considering how this philosophy might apply to the 21st century. Navia reveals that he is as pessimistic as Schopenhauer, but Ken challenges him, wondering if there really is no way to make things better. In what John calls a consolation, and Ken a project of self-amelioration, they conclude with Navia’s notion that all we can do is make changes on our own individual level, and make things a bit better in that small way.

• Roving Philosophical Reporter (seek to 5:31): Caitlin Esch investigates different people’s definitions and understandings of the modern usage of the word “cynicism.” Speaking with Geoff Nunberg, Adjunct Professor at the UC Berkley School of Information, she learns that although today the term is used almost as a critique, in Diogenes’ time it reflected a certain moral code, namely the protest of self-indulgence and greed. No wonder it’s Greek root translates to “dog life.”
   
• 60-Second Philosopher (seek to 49:06): Ian Shoals quickly reflects on how much of what we know of Diogenes has been passed down in the form of small anecdotes.