A Note from James:

Man, what a fascinating career Robert Rosenkranz has had—multi-billionaire, involved in virtually every part of finance and American industry. He wrote a book called The Stoic Capitalist, and what really stands out is how he's actively applied stoic principles to achieve immense success throughout his career. Even from a young age, stoicism played a crucial role, guiding him through critical business decisions. It's a real pleasure speaking with Robert—an American icon.

Episode Description:

James welcomes Robert Rosenkranz, author of The Stoic Capitalist: Advice for the Exceptionally Ambitious, to discuss how applying stoicism's timeless principles helped him navigate pivotal career decisions and financial challenges. Robert candidly shares his experiences—from early high-stress deals to launching a private equity firm where he risked his entire net worth—and explains why stoic philosophy remains essential for rational decision-making in business and life. The conversation highlights how embracing uncertainty and questioning assumptions can lead to clarity and resilience in a constantly changing world.

What You'll Learn:

• How to differentiate between rational risks and emotional fears in critical decisions.
• Strategies for recognizing and overcoming cognitive distortions like catastrophizing.
• Practical applications of stoicism in modern investing and entrepreneurship.
• Insights into adapting to rapid technological changes, particularly AI.
• The importance of spousal support and personal relationships in career success.
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Timestamped Chapters:

• [00:00 ] Introduction to Robert Rosenkranz
• [02:00 ] The First Major Deal and Stoic Principles
• [05:00 ] Risk and Rational Decision Making
• [09:00 ] The Role of Biographies and Early Influences
• [12:00 ] The Importance of Spousal Support
• [28:00 ] Stoicism and Cognitive Behavioral Therapy
• [34:00 ] Exploring Financial Trends and Technology
• [35:00 ] The Impact of Artificial Intelligence
• [36:00 ] Addressing Fears and Job Displacement
• [37:00 ] Adapting to Technological Change
• [44:00 ] The State of the US Economy
• [48:00 ] Investment Strategies and Market Behavior
• [54:00 ] Stoicism and Its Influence on Investing
• [57:00 ] The Role of Social Media in Society
• [63:00 ] Reflections on Public Service and Education
• [67:00 ] Conclusion and Final Thoughts

Additional Resources:

• The Stoic Capitalist by Robert Rosenkranz
• How to Think Like a Roman Emperor by Donald Robertson
• The Obstacle Is the Way by Ryan Holiday
• "The Smoot-Hawley Tariff and the Great Depression" - The Economist
• Open to Debate

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