The Philosopher Who Didn’t Care What Anyone Thought

The Daily Stoic Podcast | Ryan Holiday | February 7, 2026

Overview

This episode explores the life, philosophy, and legacy of Diogenes the Cynic, often viewed as the most "badass" philosopher of the ancient world. Host Ryan Holiday delves into what set Diogenes apart, how his radical principles influenced Stoicism, and what lessons modern listeners can extract from his unapologetic approach to virtue and self-sufficiency. Featuring insights from scholars Arthur Brooks and Inger Kuen, the episode highlights the provocative and sometimes outrageous spirit of the Cynics, pondering the deeper value of radical self-determination and questioning social conventions.

Key Discussion Points & Insights

1. Who Was Diogenes?

• Ryan Holiday sets the stage by contrasting Diogenes with more 'respectable' philosophers like Marcus Aurelius and Socrates—Diogenes was poor, lived on the streets, begged for food, and "could challenge Alexander the Great to his face."
  • "It was this poor homeless man who could challenge Alexander the Great to his face... and yet, even though he didn't write basically anything down, had an enormous philosophical legacy." (02:47)
• Diogenes is portrayed as foundational to Stoicism’s development, despite his affiliation to the prior school of Cynicism.

2. Cynicism vs. ‘Cynicism’

• Clarifying the term: Cynicism as a philosophy is distinct from the modern sense of the word.
  • “Just as Stoicism is not lowercase stoic… that’s not what the school of Cynicism is as a philosophy either.” (03:35)
• Early Cynics (Diogenes, Antisthenes) consciously lived in opposition to materialism and superficial social conventions, advocating for living according to nature.
• Their actions could be radical or performatively extreme (nudity, public defiance), serving to question taboos and stimulate philosophical self-examination.

3. The “Punk Rockers” of Philosophy

• Arthur Brooks likens the Cynics to "punk rockers"—transgressive, radical, deliberately “taking things too far” to reveal unexamined truths in society.
  • “They are transgressive and radical by taking it too far, actually providing us insights about a moderate middle ground.” (05:06)
• Diogenes’ minimalism: Notable for stories like smashing his only cup after seeing a boy drink with his hands.
  • “Even here, having reduced what he thought his needs were... has one more that he can get rid of.” (05:43)

4. Diogenes’ Origin Story

• Inger Kuen provides historical context: Diogenes was exiled from Sinope (now Turkey) due to his father’s involvement in a coinage scandal, ending up in Athens.
  • “At a certain point... he gets exiled, which means he loses his citizen rights and ends up in Athens, which to him ends up being really exciting.” (06:52)
• In Athens, he meets Antisthenes—Socrates’ student—who influences Diogenes’ philosophical trajectory.

5. Diogenes’ Defiance and Radical Practice

• Diogenes delighted in exposing hypocrisy—whether challenging religious corruption or social customs.
  • “He says, oh look, the big thieves are leading away the little thieves.” (12:40)
• Practiced ascetic discipline: subjected himself to harsh weather, practiced begging from statues to develop indifference to insult or rejection.
• Disagreement with Plato:
  • “If you had come to Dionysus’ court, you wouldn't have to [wash cabbages]… Diogenes: ‘If you just washed your cabbages, you wouldn’t have had to go to Dionysus’ court.’” (14:44)

6. The Iconic Encounter with Alexander the Great

• Famous story: Alexander the Great asks what Diogenes wants, Diogenes replies, “Yeah, you can get out of my sun.”
  • “His request for the most powerful man... is to just get out of his way.” (16:17)

7. Cynicism and Stoicism: Philosophical Kin And Divergence

• Stoicism descends from Cynicism—Zeno founded Stoicism after studying under the Cynic Crates, who traced his lineage from Diogenes.
• Philosophical difference:
  • Stoics believe in an ordered, divinely-principled universe; Cynics are more anarchic, questioning societal necessity.
  • “For the Stoics, there is a divine organizing principle... for the Cynics, there is no such overarching organizing principle.” – Inger Kuen (18:19)
• Cynics celebrated the natural state—what’s not rooted in nature is open to challenge or rejection.

8. The Pursuit of Freedom

• Both philosophies prize freedom—not legal, but existential freedom from passions, desires, and dependency.
  • “Diogenes talked about people being slaves three times over… Seneca said, show me someone who isn’t a slave.” (22:18)
• The fewer one’s needs and desires, the less vulnerable one is to external control.

9. Rigorous Treatment of the Body and Mind

• Physical hardship—embracing weather, hunger, discomfort—was seen as an exercise to toughen mind and will.
• Parallels in Stoicism:
  • “Seneca said, we treat the body rigorously so that it is not disobedient to the mind.” (24:35)

10. A Life-long Learner’s Spirit

• Story: When told to slow down in old age, Diogenes responds, "If you were running a distance race, would you slow down when you were approaching the finish line? Wouldn’t I do better to speed up?" (26:07)
• Marcus Aurelius and Epicurus are cited similarly—always striving to learn.

11. Virtue and Excellence Above All

• Diogenes was uninterested in fame or power.
  • “I see many men competing in wrestling and running, but no one competing in the pursuit of human excellence.” (27:23)
• Willingness to change:
  • When questioned about inconsistency, Diogenes quipped, "I used to piss my bed, but I don’t do that anymore."
  • “The point is, a philosopher should be able to change your mind.” (27:58)

Notable Quotes & Memorable Moments

• On the Cynic way of living:
  • “They are transgressive and radical by taking it too far, actually providing us insights about a moderate middle ground.”
    —Ryan Holiday (05:06)
• On ascetic minimalism:
  • “He smashes his cup on the ground.” (05:43)
• On logic vs. society:
  • “One believes in order and systems and logic, and the other is a little bit more random and anarchic… this is just how things are. God didn’t make them this way, and they don't have to remain this way.” —Ryan Holiday (20:34)
• On learning and changing:
  • “I used to piss my bed, but I don’t do that anymore.”
    —Diogenes (27:58)
• On the legacy of questioning:
  • “By taking things to a logical extreme, or by subjecting them to extreme circumstances, Diogenes helps us understand ourselves, our own assumptions, our own ideas better.”
    —Ryan Holiday (28:46)

Key Timestamps

• 02:42 — Introduction of Diogenes as “the most powerful philosopher in the ancient world”
• 03:24-06:08 — What true Cynicism means, and its radical expressions
• 06:51-09:12 — Diogenes’ origin and exile—historical context with Inger Kuen
• 12:27-16:17 — Anecdotes of Diogenes’ public defiance, interaction with Alexander the Great
• 17:07-20:02 — Philosophical differences and link between Cynics and Stoics (Inger Kuen)
• 22:11-24:35 — Freedom as self-sufficiency; physical rigor in philosophy
• 26:07-27:58 — Lifelong learning, changing perspective, the true pursuit of human excellence

Takeaways for Listeners

• Diogenes’ legacy is one of relentless questioning and ruthless honesty—about oneself, society, and authority.
• While few could or should imitate his extremity, examining his life helps challenge our own assumptions about necessity, virtue, and social conventions.
• Stoics inherit much from the Cynics, especially the concept of inner freedom, but redirect it through order and rational organization.
• Key virtues: Courage to offend, strength in self-sufficiency, the relentless pursuit of excellence, and humility to change.
• Diogenes reminds us: The path of philosophy isn’t about acceptance, but continual examination and growth.

For further exploration: Visit DailyStoic.com or read more about Cynicism, Stoicism, and the fascinating characters who shaped Western philosophy.