The Daily Stoic Podcast
Episode: Bert Kreischer Has a Stoicism Problem
Host: Ryan Holiday
Guest: Bert Kreischer
Date: January 28, 2026

Episode Overview

In this episode, Ryan Holiday sits down with comedian Bert Kreischer, known for his wild stage persona and shirtless performances, to discuss Bert’s skepticism (and secret fascination) with Stoicism. What unfolds is a lively, candid, and often hilarious conversation that examines the misconceptions, challenges, and very real struggles of trying to live by Stoic philosophy in today’s world—especially when your life is as unpredictable and public as Bert's. The conversation weaves personal stories, historical anecdotes, and deep questions about achievement, self-worth, and how to handle criticism—both internal and external.

Key Discussion Points & Insights

1. The Phone Call Origin Story of Bert’s Stoicism Skepticism

• (00:30–04:35)
  • Ryan recounts the unexpected phone call from Tom Segura, in which Bert was “shitting all over stoicism” and called it “stupid and a dumb way to live.”
  • Bert admits, “just the name stoic is not how I live my life. Like, I'm not stoic.” (04:35, Bert Kreischer)
  • Tom Segura requests Ryan to give Bert a “basic principle of stoicism,” leading into a simple breakdown of Stoicism’s core: “We don’t control what happens in the world, but we control how we respond.” (Ryan, 02:46)

2. Misconceptions and Stereotypes of Stoicism

• (04:35–08:09)
  • Bert jokes about not being able to relate to the “stoic” personality, confusing historical figures, and being a natural extrovert.
  • Will Compton jokes about Marcus Aurelius being the “old guy who dies in Gladiator,” highlighting common pop-culture confusion.
  • Ryan clarifies: “Stoicism is not some wallflower cynicism. It's perfectly wonderful to enjoy your success. The only problem is if you think it makes you special or that you could die without it.” (04:48, Ryan Holiday)

3. Vulnerability, Not Being Taken Seriously, and Career Reflections

• (08:10–13:50)
  • Bert opens up about being typecast as the “comedian who takes his shirt off,” and how that overshadows his storytelling ability: “A lot of people blow me off because I take my shirt off...they overlook the catalog.” (08:17, Bert Kreischer)
  • He relates a real-life story that inspired his show’s premise, being flown out for a high-paying corporate gig where the crowd only wanted his “greatest hits.”
  • Bert confesses, “I do want to fit in...that’s not popular online...but what am I supposed to do? That’s who I am.” (13:36, Bert Kreischer)

4. Bert’s Near-Death Waterfall Story: Stoic or Not?

• (11:09–13:55)
  • Bert narrates rappelling off a waterfall for a TV show, having a reflective, present moment before things go awry and he falls, barely surviving.
  • Ryan observes the Stoic themes in the story—taking stock, appreciating where you are—but points out the non-stoic moment: “Maybe the only non stoic thing was...if you’re screaming your head off while you’re hanging upside down.” (14:12, Ryan Holiday)

5. The Challenge of Being a Sensitive Extrovert in a Stoic World

• (13:55–16:05)
  • Bert discusses being a “raw nerve,” wanting to fit in, and wishing he could be more reserved like Stoic icons or even George Washington.
  • He grapples with the idea of holding back in conversation to be “more stoic,” but concedes that's not authentic to himself.

6. Public Criticism, Hurt Feelings, and Celebrity Anxiety

• (16:15–18:53)
  • Bert reveals the sting of a negative headline: “Bert Kreischer ruins Christmas Day,” and how disproportionately such criticism affects him.
  • He acknowledges, “If I get upset or if I get my feelings hurt, it’s uncontrollable...massive instant anxiety...this ruined half the day.” (17:16, Bert Kreischer)
  • His family gives competing advice—one daughter rationalizes the critic, the other urges him to “Google his name” for payback, highlighting the tension between Stoic detachment and emotional reactivity.

7. Stoicism as a Practice, Not a Trait

• (20:00–23:05)
  • Ryan explains Stoicism is not an innate characteristic but an ongoing practice: “If it’s not work, you don’t get any credit for it...everyone is struggling with it.” (20:25, Ryan Holiday)
  • He cites stories of George Washington’s fiery temper and the intentional self-control beneath the surface.
  • Both admit to being affected by online criticism, and Ryan describes digital boundaries (“my social media is on my wife’s phone”) as a Stoic strategy.

8. The Risks of Overworking & The Value of Restraint

• (26:12–30:58)
  • Bert confesses to having “squandered” talent and burning out, prompting him and Tom Segura to scale back their workload on their podcast “Two Bears, One Cave.”
  • “To pull back a little bit is the stoic way—to not overwork. Restraint is the stoic way,” (26:18, Ryan Holiday)
  • Both discuss how scary it is to step off the professional “merry-go-round”—the anxiety of being forgotten—but how doing less is crucial to preserving quality and joy in their work.

9. The Problem of “Enough” and Moving the Goalposts

• (30:53–31:42)
  • The conversation explores the ever-moving definition of “enough”—whether it’s money, success, or fame, and the self-defeating pursuit of more.
  • “The problem is that you always move that number,” (30:58, Ryan Holiday) leading to chasing fulfillment that is never fully attainable.

10. Jealousy, Comparison, and Authenticity in Artistic Communities

• (35:17–39:28)
  • Bert laments the prevalence of jealousy and shifting dynamics among comics as people become successful.
  • Ryan shares wisdom: “Work, family, scene—pick two,” recommending limiting involvement in industry gossip or comparison as a Stoic strategy.
  • “It’s just better to be doing your own thing and running your own race.” (38:48, Ryan Holiday)

11. Channel Markers, Unconventional Paths, and Seneca

• (38:48–40:29)
  • Bert introduces the “channel marker” analogy—looking for mentors and examples like Joe Rogan and Bill Burr to guide his own path.
  • Ryan reads a passage from Seneca: “Happiness is having a sense of the path that you're on. Not being distracted by paths that crisscross yours. Especially not following the footsteps of people who are lost.” (39:59, Ryan Holiday)
  • Bert jokes, “Seneca—I always thought he was just a different type of Toyota.” (40:24, Bert Kreischer)

12. History Deep Dive: Seneca, Nero, and the Dangers of Needing to Be Liked

• (40:29–43:47)
  • Ryan recounts the tortured relationship between Nero and his Stoic tutor Seneca—Nero as the archetype of needing to be liked and spinning out of control.
  • Bert: “You’re talking to the guy that’s on Testosterone and benching £325. Yeah, keep going.” (43:12, Bert Kreischer)
  • Ryan details the tragic stories of hubris, power, and loss of self, drawing parallels with contemporary anxieties around validation and legacy.

Notable Quotes & Memorable Moments

• On misunderstanding stoicism:
  “Just the name stoic is not how I live my life. Like, I'm not stoic.” (04:35, Bert Kreischer)

• The “Dance Monkey” dilemma:
  “For 25 grand, you'd be shocked how hard this monkey dances.” (10:19, Bert Kreischer)

• On emotional vulnerability:
  “If I get upset or if I get my feelings hurt, it's uncontrollable... massive instant anxiety... this ruined half the day.” (17:16, Bert Kreischer)

• On Stoicism as intentional work:
  “If it’s not work, you don’t get any credit for it… everyone is struggling with it.” (20:25, Ryan Holiday)

• On the perils of endless craving:
  “The problem is that you always move that number.” (30:58, Ryan Holiday)

• On detachment and focus:
  “It’s just better to be doing your own thing and running your own race.” (38:48, Ryan Holiday)

• Misunderstanding Seneca:
  “Seneca—I always thought he was just a different type of Toyota, but he's fucking great.” (40:24, Bert Kreischer)

• Parallels with Nero:
  “Nero desperately wanted to be liked, and he desperately wanted to be liked as both an athlete and an artist...” (43:03, Ryan Holiday)

Timestamps for Key Segments

• Opening & Bert’s Stoicism Beef: 00:30–04:35
• Basic Stoic Principles Explainer: 02:46–04:35
• Bert’s TV & Corporate Gig Story: 08:10–10:19
• Bert’s Waterfall Accident & Reflection: 11:09–13:55
• Bert on Sensitivity & Belonging: 13:50–16:05
• Negative Press/Online Criticism: 16:15–19:11
• Stoicism as Effortful Practice: 20:00–23:05
• Work-Life Boundaries & Podcasting: 26:12–30:58
• “Enough,” Money, & FOMO: 30:53–32:16
• Jealousy & the Comedy Scene: 35:17–39:28
• Seneca, Channel Markers, & Life Paths: 38:48–40:29
• Deep Dive: Seneca, Nero, & Needing Validation: 40:29–43:47

Episode Tone and Style

The episode has a playful yet vulnerable tone throughout. Bert’s loud, self-deprecating humor contrasts with his genuine introspection and longing for Stoic calm. Ryan guides the conversation with warmth and depth, providing historical context and practical insight without judgment. Their dynamic keeps the exchange quick, grounded, and often hilarious (Bert's wild analogies and Ryan’s measured patience are highlights). The episode is accessible and illuminating for anyone questioning what it means to adopt Stoic principles—and finding it surprisingly difficult.

For more on Stoicism and to access bonus content, visit DailyStoic.com.

(End of Part 1; Ryan notes that Part 2 will come later in the week.)