In Part 2, we move from Ray Dalio’s history to his mechanics. After the 1982 "Abyss" nearly destroyed his career, Dalio realized he couldn't trust his own brain to make objective decisions. He needed an operating system that could override his ego and his emotions.

This episode is a deep dive into the Life Principles—the logical framework Dalio built to turn himself from a "dumb shit" into the architect of the world’s most successful hedge fund. We explore why most people fail because they are "stuck in their own heads" and how Dalio uses the laws of nature to engineer a life of constant evolution.

What to expect in this episode:

• The Designer vs. The Worker: The life-changing distinction between the version of you that writes the rules and the version of you that executes them.
• The Machine Model: Why you need to stop seeing your life as a series of events and start seeing it as a mechanical system you can repair.
• Hyperrealism: Why "wishing" is the enemy of winning, and how to embrace reality even when it’s brutal.
• The 5-Step Process for Success: Dalio’s clinical loop for getting anything you want—from setting audacious goals to diagnosing your own failures.
• Pain + Reflection = Progress: How to stop running from the "sting" of loss and start using it as the raw data for your next breakthrough.
• First-Order vs. Second-Order Consequences: Why the things that feel "good" in the first 5 minutes are usually the traps that keep you broke for 5 years.
• Firing Yourself: How to objectively identify your own weaknesses and find the "workarounds" that allow you to win without being perfect.
• Evolution as the Greatest Reward: Why the goal isn't just money—it’s the rapid trial-and-error process that moves you toward the "higher level."

Books & Resources Mentioned:

• Principles: Life and Work by Ray Dalio
• How To Build A Company Where The Best Ideas Win (YouTube)
• The Bridgewater Newsletter
• How The Economic Machine Works (YouTube)

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→ Website: moneymenshow.com

• (00:00) - Introduction and Recap of Part One
• (00:27) - Ray Dalio's Response to Catastrophe
• (02:04) - Embracing Reality and Dealing with It
• (06:10) - The Importance of Truth and Radical Open-Mindedness
• (10:21) - Learning from Nature and Evolution
• (15:51) - Pain Plus Reflection Equals Progress
• (17:38) - Weighing Second and Third Order Consequences
• (19:27) - Owning Your Outcomes
• (22:49) - The Five-Step Process to Get What You Want Out of Life
• (28:37) - Designing a Plan for Success
• (32:10) - The Power of Humility and Collaboration
• (33:22) - The Importance of Radical Open-Mindedness
• (34:16) - Overcoming Ego and Blind Spots
• (37:42) - The Art of Thoughtful Disagreement
• (43:32) - Understanding Human Wiring and Its Impact
• (47:12) - The Role of Meaningful Work and Relationships
• (49:16) - Navigating the Great Brain Battles
• (55:13) - Synthesizing Information for Better Decisions
• (01:04:10) - The Math of Decision Making
• (01:05:38) - Building a Systematic Approach for the Future

This episode is about Ray Dalio—the man who built Bridgewater Associates from a two-bedroom apartment into a $150 billion machine by learning to embrace his own ignorance.

Most people know him as a billionaire "philosopher," but the real story is about a man who was so dead wrong in 1982 that he lost everything and had to borrow $4,000 from his father just to pay his family's bills. This is the story of how that "Abyss" forced him to change his life’s operating system.

What to expect in this episode:

• The "Dumb Shit" Mindset: Why Dalio’s greatest edge wasn't his IQ, but his willingness to admit he knew nothing.
• The 1971 Gold Standard Devaluation: The moment a young Ray realized that the future rarely looks like the past.
• The 1982 Abyss: A clinical look at the trade that almost ended his career and the public humiliation that followed.
• The "Economic Doctor" Strategy: How he dissected the debt crises of the 80s to find the patterns everyone else missed.
• The Holy Grail of Investing: His discovery of "15 to 20 uncorrelated return streams" and why it’s the only way to survive.
• GPS for the Human Brain: Why he stopped trusting his own gut and started building algorithms to override his ego.
• Hyper-Realism: Moving from "I wish the market would do this" to "What is the market actually doing?"
• The Power of Pain: Why Dalio views his greatest failures as the most valuable data points he ever received.
• Radical Open-Mindedness: The tactical advantage of seeking out the smartest people who disagree with you.
• The Timeless Truth: You don't win by being "smart"—you win by building a machine that is smarter than you are.

Books & Resources Mentioned:

• Principles: Life and Work by Ray Dalio
• How To Build A Company Where The Best Ideas Win (YouTube)
• The Bridgewater Newsletter
• How The Economic Machine Works (YouTube)

Follow the Show:

→ Website: moneymenshow.com

If you found this episode helpful, share it with someone who might need it.

• (00:00) - 03: Ray Dalio: Principles: Part 01
• (29:45) - Final half
• (41:06) - Editing up to here

This episode is about Paul Tudor Jones — the hedge fund legend who turned defense into an art form.

He’s best known for predicting the 1987 crash and returning over 200% that year — but the real lesson from Jones isn’t how he made money, it’s how he kept it.

What to expect in this episode:

• How a boxer’s discipline became a trader’s edge
• Why he says: “Don’t focus on making money. Focus on protecting what you have.”
• The moral foundation from his Memphis upbringing that shaped his risk mindset
• Lessons from Eli Tullis — the mentor who taught him composure under fire
• The decision to quit a lucrative brokerage job because it “lacked accountability”
• His 10% monthly drawdown rule — and why it keeps him in the game
• The power of humility: “Every day, I assume every position I have is wrong.”
• How he turned the 1987 crash into his defining moment
• Why generosity and gratitude are essential to staying balanced in markets
• The timeless truth: great trading is not about being right — it’s about not dying.

Books & Resources Mentioned:

• Market Wizards by Jack D. Schwager
• Trading In The Zone by Jack Schwager

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→ Website: moneymenshow.com

If this episode helped you think more like a survivor than a speculator, share it with one friend who loves the markets and making money

This episode is about Jesse Livermore. The most legendary trader who ever lived, and the man behind Reminiscences of a Stock Operator.

He made $100 million shorting the 1929 crash (about $1.9 billion today), yet died broke just a decade later.
Livermore’s life reads like a novel: ambition, obsession, and lessons written in blood.

What to expect in this episode:

• How Livermore discovered technical analysis before it even had a name
• The boy who ran away at 14 to chase numbers on a ticker tape
• Why he said: “The market does not beat them. They beat themselves.”
• How he made his first fortune shorting the 1907 Panic — and his biggest one in 1929
• The deadly enemies of every trader: ignorance, greed, fear, and hope
• His rule for sitting tight — and why it’s harder than being right
• How obsession turned from his greatest strength into his undoing
• Why the game teaches you the game… and then breaks you

“It never was my thinking that made the big money for me. It always was my sitting.” — Jesse Livermore

Books Mentioned:

• Reminiscences of a Stock Operator by Edwin Lefèvre
• How to Trade in Stocks by Jesse Livermore

Follow the Show:
→ Website: moneymenshow.com

If you got value from this episode share it with one friend who loves markets, history, or human psychology.