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Not Seeking Wisdom DESTROYS Great Minds | Ryan Holiday & Billy Oppenheimer

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Oct 25, 2025

Guest

Billy Oppenheimer

Billy Oppenheimer, a research assistant and writer for Ryan Holiday, dives deep into the pitfalls of unchecked genius. They analyze how success can blind even the smartest minds, using Elon Musk as a cautionary tale for those seduced by solitude and echo chambers. The conversation explores the thin line between intelligence and wisdom, the importance of trusted advisors, and how overconfidence can derail clear thinking. Tune in for insights on maintaining humility and the dangers of dismissing traditional knowledge.

48:27

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ADVICE

Fix Your Information Diet

Avoid getting your information only from social media and podcasters.
Rebuild a diverse info diet to stay connected to reality.

insights

INSIGHT

Success Amplifies Disconnection

Intelligence without balance and structure quickly becomes dangerous.
Success amplifies disconnection unless you deliberately create stabilizers.

question_answer

ANECDOTE

Lineage Shapes Public Behavior

Ryan cites Jill Lepore's New Yorker piece linking Elon Musk to a problematic family lineage.
That family context helps explain recurring themes in Musk's public behavior.

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Wisdom, Apprenticeship, and Paying It Forward

02:04 • 6min

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Why Elon Musk Became a Cautionary Tale

08:10 • 3min

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What Happens When Success and Echo Chambers Take Over

10:50 • 1min

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Family Lineage and Formative Influences on Beliefs

12:02 • 5min

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Rarity of Self-Awareness and Biographical Clarity

How Power, Anger, and Firing Create a Chilling Effect

20:21 • 3min

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The Need for Continuity: Long-Term Trusted Advisors

23:20 • 40sec

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Sam Bankman-Fried and Tech Figures as Modern Cautionary Tales

24:00 • 4min

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Information Diets, Expertise, and the Death of Real Knowledge

27:40 • 3min

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Cognitive Dissonance and the Pressure to Conform

31:05 • 1min

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Difference Between Being Smart and Being Wise

32:10 • 2min

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Why Contrarian Success Can Destroy Intellectual Humility

Board of Directors, Commodus, and the Importance of Listening

40:11 • 1min

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Editing, Feedback, and the Limits of Authorial Certainty

41:30 • 2min

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Interventions, Continuity, and When to Heed Warnings

43:51 • 45sec

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How the Virtue Series Evolved and Structural Challenges

44:36 • 4min

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Advice for Writing a First Book and Overcoming Insecurity

• Mentioned in 380 episodes

The obstacle is the way

Ryan Holiday

In 'The Obstacle Is the Way', Ryan Holiday presents a framework for turning obstacles into successes. Drawing from the philosophy of Stoicism and the writings of Marcus Aurelius, Holiday outlines three disciplines: perception, action, and will. He illustrates these principles with historical anecdotes from figures such as John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, and Steve Jobs. The book emphasizes the importance of perception in shaping one's response to obstacles, the need for intentional and creative action, and the cultivation of will to persist through challenges. Holiday argues that by adopting these Stoic principles, individuals can transform their obstacles into opportunities for growth and success.

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• Mentioned in 18 episodes

Disrupt Everything

James Patterson

• Mentioned in 380 episodes

The obstacle is the way

Ryan Holiday

#80

• Mentioned in 153 episodes

Moneyball

The Art of Winning an Unfair Game

Michael Lewis

The book tells the story of the Oakland Athletics' 2002 season, where General Manager Billy Beane and his assistant Paul DePodesta used advanced statistical analysis, known as sabermetrics, to assemble a competitive team despite a limited budget. The approach, pioneered by Bill James, focused on metrics such as on-base percentage and slugging percentage rather than traditional measures like batting average and runs batted in. This data-driven strategy allowed the Athletics to compete with teams having much larger payrolls, like the New York Yankees, and achieve significant success, including a 20-game winning streak and a playoff appearance.

• Mentioned in 983 episodes

Atomic Habits

James Clear

Atomic Habits by James Clear provides a practical and scientifically-backed guide to forming good habits and breaking bad ones. The book introduces the Four Laws of Behavior Change: make it obvious, make it attractive, make it easy, and make it satisfying. It also emphasizes the importance of small, incremental changes (atomic habits) that compound over time to produce significant results. Clear discusses techniques such as habit stacking, optimizing the environment to support desired habits, and focusing on continuous improvement rather than goal fixation. The book is filled with actionable strategies, real-life examples, and stories from various fields, making it a valuable resource for anyone seeking to improve their habits and achieve personal growth.

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• Mentioned in 73 episodes

Wisdom Takes Work

Ryan Holiday

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• Mentioned in 12 episodes

The New New Thing

A Silicon Valley Story

Michael Lewis

The book tells the story of Jim Clark, the founder of several billion-dollar companies including Silicon Graphics, Netscape, and Healtheon. It explores Clark's relentless pursuit of the 'new new thing' and his impact on the tech industry. Lewis provides a detailed look at the roles of venture capitalists, entrepreneurs, and programmers in Silicon Valley, highlighting the unique culture and financial dynamics of the region during the late 1990s. The book also critiques the traditional business models and the inflated value of tech companies during that period.

What happens when brilliance goes unchecked? In today's episode, Ryan and his research assistant Billy Oppenheimer dig into the cautionary side of genius, from Elon Musk’s unraveling to why so many smart people end up making dumb decisions. They talk about how success can warp reality, why intelligence without wisdom becomes dangerous, and how even the brightest minds can lose their way when they stop listening, stop learning, and stop taking care of themselves.

Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.

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