20 Jan 2026

2h 6m

Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

Invest Like the Best with Patrick O'Shaughnessy

The conversation explores Patrick O'Shaughnessy's personal and professional philosophies, emphasizing the importance of helping others and discovering untapped potential. O'Shaughnessy discusses his principle of identifying and championing undiscovered talent, highlighting his efforts to foster their growth and introduce them to the world. He contrasts goal-oriented approaches with principle-based living, advocating for a focus on personal principles like spotting undiscovered talent, which informs daily decisions and fosters a fulfilling life. The discussion touches on the role of media and investing as interconnected tools for championing individuals and ideas, and the significance of building deep, meaningful relationships. O'Shaughnessy shares personal anecdotes, including the influence of his cousin Tim and his wife Lauren, to illustrate how acts of kindness and strong relationships shape one's life and career.

Outlines

Part 1: Sponsor Spotlights & Tech Solutions

Part 2: Introduction & The Philosophy of Support

Part 3: Principles Over Goals

Part 4: Introspection, Fear, and Originality

Part 5: Finding "Your Thing" and Sustaining Success

Part 6: Knowledge, Mentorship, and Media Strategy

Part 7: Quality, Volume, and the Creative Loop

Part 8: Intensity, Leadership, and Legacy

Part 9: Final Reflections & Closing

Continue

Preview

How to Get Rich: Every EpisodeNaval

Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

Invest Like the Best with Patrick O'Shaughnessy

Part 1: Sponsor Spotlights & Tech Solutions

00:00RAMP's AI Automates Expense Reviews, Reallocating Finance Team Time for Strategic Planning

RAMP's AI Automates Expense Reviews, Reallocating Finance Team Time for Strategic Planning

00:50Rogo: AI Platform Purpose-Built for Wall Street, Enhancing Investment Decisions

Rogo: AI Platform Purpose-Built for Wall Street, Enhancing Investment Decisions

02:24WorkOS: Streamlining Enterprise Readiness for Fast-Growing Software Companies

WorkOS: Streamlining Enterprise Readiness for Fast-Growing Software Companies

Part 2: Introduction & The Philosophy of Support

03:33Introduction to David Senra's Interview with Patrick O'Shaughnessy on "Invest Like the Best"

Introduction to David Senra's Interview with Patrick O'Shaughnessy on "Invest Like the Best"

05:11Championing Underdog Talent: The Excitement of Early Discovery and Support

Championing Underdog Talent: The Excitement of Early Discovery and Support

07:35Positive Sum and the Value of Promoting Others: A Story of Early Support

Positive Sum and the Value of Promoting Others: A Story of Early Support

10:11The Upanishads, Kindness, and Betting on Potential: Shaping a Worldview of Helping Others

The Upanishads, Kindness, and Betting on Potential: Shaping a Worldview of Helping Others

Part 3: Principles Over Goals

13:47No Goals, Just Principles: A Different Approach to Life and Work

No Goals, Just Principles: A Different Approach to Life and Work

15:50Inventing on Principle: Finding a Life's Mission Through a Universal Idea

Inventing on Principle: Finding a Life's Mission Through a Universal Idea

18:42Embracing the Periphery: Opportunity and the Rejection of Long-Term Goals

Embracing the Periphery: Opportunity and the Rejection of Long-Term Goals

21:34The Feeling of Being Alive: Chasing a Principle for a Fulfilling Life

The Feeling of Being Alive: Chasing a Principle for a Fulfilling Life

Part 4: Introspection, Fear, and Originality

24:50Overcoming Fear: Pursuing Originality and the Point of Existence

Overcoming Fear: Pursuing Originality and the Point of Existence

27:28From Introspection to Action: Solving Problems and Defining Organizing Principles

From Introspection to Action: Solving Problems and Defining Organizing Principles

30:06Family Foundations: Contrasting Backgrounds and the Power of Founding a New Legacy

Family Foundations: Contrasting Backgrounds and the Power of Founding a New Legacy

32:52Seeking True Understanding: Human Nature and the World We're Creating

Seeking True Understanding: Human Nature and the World We're Creating

34:14Bruce Springsteen's Autobiography: Finding Personal Resonance in Shared Experiences

Bruce Springsteen's Autobiography: Finding Personal Resonance in Shared Experiences

37:06The Importance of Individual Recipes: Avoiding Pitfalls and Inspiring Originality

The Importance of Individual Recipes: Avoiding Pitfalls and Inspiring Originality

Part 5: Finding "Your Thing" and Sustaining Success

39:04The Search for "Your Thing": Hardship, Inspiration, and Unique Perspectives

The Search for "Your Thing": Hardship, Inspiration, and Unique Perspectives

41:45The Privilege of Being Who You Are: Creation, Service, and the Power of Self-Expression

The Privilege of Being Who You Are: Creation, Service, and the Power of Self-Expression

44:25Sustained Success: Avoiding the Trap of Money, Power, and Fame

Sustained Success: Avoiding the Trap of Money, Power, and Fame

47:00Health, Work, and Relationships: Prioritizing What Matters Most

Health, Work, and Relationships: Prioritizing What Matters Most

49:25The Value of Relationships: Building Connections Through Understanding

The Value of Relationships: Building Connections Through Understanding

51:23Bruce Springsteen's Realization: Life is More Important Than Work

Bruce Springsteen's Realization: Life is More Important Than Work

53:30The Lie We Tell Ourselves: Identifying and Overcoming Personal Obstacles

The Lie We Tell Ourselves: Identifying and Overcoming Personal Obstacles

55:24Developing Skills for Sustained Success: The Path Out is Others

Developing Skills for Sustained Success: The Path Out is Others

Part 6: Knowledge, Mentorship, and Media Strategy

57:33Generative Fuel: The Importance of Positive Motivation and Learning from Examples

Generative Fuel: The Importance of Positive Motivation and Learning from Examples

1:00:09The Unfair Advantage: Learning from Others and Packaging Knowledge

The Unfair Advantage: Learning from Others and Packaging Knowledge

1:02:47Relationships Run the World: Building Connections and Sharing Knowledge

Relationships Run the World: Building Connections and Sharing Knowledge

1:05:06The Impact of Mentors: Values, Simplicity, and Uncompromising Principles

The Impact of Mentors: Values, Simplicity, and Uncompromising Principles

1:08:20The Power of Profiles: Shining a Light on Compelling Individuals

The Power of Profiles: Shining a Light on Compelling Individuals

1:11:11Obsession and the Best Profiles: A Double Whammy of Talent and Passion

Obsession and the Best Profiles: A Double Whammy of Talent and Passion

1:13:55The Desire for More: Expanding the Scope of Colossus Beyond Podcasting

The Desire for More: Expanding the Scope of Colossus Beyond Podcasting

Part 7: Quality, Volume, and the Creative Loop

1:17:01The Fascination with People: Learning About Ourselves Through Others

The Fascination with People: Learning About Ourselves Through Others

1:18:40The Allure of Hardship: Singular Creations That Can't Be Easily Copied

The Allure of Hardship: Singular Creations That Can't Be Easily Copied

1:20:28The Power of a Cover: Spotlight and Attention as a Valuable Resource

The Power of a Cover: Spotlight and Attention as a Valuable Resource

1:23:40The Importance of Volume: Refining Taste and Reverse Engineering Success