In this episode, Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal missteps to famous entrepreneurial gambles, this episode is a deep dive into the art of learning from experience, knowing when to listen, and the cost of stubbornness. Plus, Holiday revisits his roots to discuss how Stoic principles can guide you in navigating feedback, balancing ambition with self-awareness, and understanding the fine line between determination and delusion.

Holiday is a New York Times bestselling author. He has written over 10 books, covering both the fundamentals of Stoicism as well as key elements of modern-day marketing and media. His most recent release is Right Thing, Right Now. Holiday has been a guest on the podcast twice before.

Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/

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(00:00) Intro

(02:20) When to Ignore Advice

(04:49) The Importance of Reflection and Journaling

(07:26) Balancing Emotions and Stoic Practices

(24:34) Misconceptions and Historical Context of Stoicism

(29:53) The Pursuit of Excellence and Its Trade-offs

(40:58) The Power of Saying No and Opportunity Costs

(49:09) The Role of Anger and Emotional Control

(52:58) Defining Self-Discipline

(53:43) The Essence of Self-Discipline

(54:29) Balancing Discipline and Life

(55:09) Consistency and Overcoming Setbacks

(56:09) The Struggle with Compulsive Tendencies

(58:33) Navigating Competition and Personal Goals

(01:01:22) Cultivating Discipline Through Physical Practice

(01:02:15) Instilling Discipline in Children

(01:04:22) Understanding Character and Virtue

(01:23:32) The Impact of Modern Technology on Writing

(01:35:04) Defining Success and Managing Expectations

Investor Adam Karr reveals his hidden playbook for spotting exceptional CEOs and building extraordinary businesses. Learn his counterintuitive techniques—from the surprising link between writing skills and executive performance to the 10-minute test that unveils a leader's true potential. Packed with battle-tested wisdom, Karr shares the deceptively simple principles that separate great business leaders from the merely good.

Adam Karr is the President and Portfolio Manager at Orbis Investments.

(00:00) Intro

(02:44) Investing Strategies and Market Games

(04:08) Adapting and Evolving Investment Styles

(05:20) The Importance of Obsession and Environment

(06:29) Aligning with Long-Term Investment Goals

(07:11) Identifying and Evaluating Obsessed CEOs

(08:13) The Role of Culture in Investment Decisions

(08:54) Building Long-Term Positions and Overcoming Short-Term Pressures

(12:21) The Blueprint for Success

(15:24) Learning from Role Models and Mentors

(21:25) The Power of Writing and Decision Analytics

(29:11) The Magic in the Last 5% of Investment Research

(35:25) Understanding Roll-Ups: Success Factors and Challenges

(36:01) Applying Knowledge for an Unfair Advantage

(37:42) Learning from Feedback and Case Studies

(40:47) The Importance of Independent Thinking

(43:06) Lessons from Industry Leaders

(49:32) The Will to Practice and Time Management

(56:44) Positioning for Success and Resilience

(01:08:59) Defining Success and Helping Others

Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/

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Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed.

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From near bankruptcy after a devastating flood to a $13.7 billion Amazon acquisition, Whole Foods founder John Mackey reveals how a small health food store became an empire that revolutionized American eating.

Discover how a single near-death experience transformed a 25-year-old college dropout into the pioneer of the organic food movement. Mackey shares raw insights from the frontlines: how he turned hostile customers into evangelists, survived multiple extinction-level threats, and built a mission-driven billion-dollar business without compromising its soul.

John Mackey is the co-founder of Whole Foods Market, where he was the CEO of the company from 1980 to 2022. He is the author of the bestselling book, Conscious Capitalism.

Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at https://fs.blog/newsletter/

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Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠https://fs.blog/membership/⁠⁠ and get your own private feed.

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Watch on YouTube: https://www.youtube.com/@tkppodcast

00:00 Introduction

02:30 From Safer Way to Whole Foods: The Early Days

03:46 The Struggles and Successes of Whole Foods

05:22 Navigating Criticism and Market Realities

08:36 The Lamar Location and the 100-Year Flood

10:46 Rebuilding and Realizing Stakeholder Value

14:57 Learning the Retail Ropes

22:35 Growth, Challenges, and Entrepreneurial Resilience

35:51 Acquisitions and Expanding the Whole Foods Empire

41:17 The Drive to Build a Chain

42:17 Founder-Led vs. Professional Management

44:38 Challenges of Bureaucracy

46:56 The Importance of Cost Control

50:44 Entrepreneurial Spirit and Creativity

52:56 Facing Leadership Challenges

01:02:57 The Amazon Merger

01:19:01 Capitalism vs. Socialism

01:26:27 The Illusion of Control in Socialism

01:27:44 The Kibbutz Experiment: Idealism vs. Reality

01:30:53 Capitalism: A Win-Win Game

01:32:04 The Power of Win-Win-Win Philosophy

01:34:28 A Personal Story: Winning Over Deborah

01:37:29 The Role of Business Planning

01:38:49 Qualities of Successful Entrepreneurs

01:49:12 The Hero's Journey: Advice for Young Entrepreneurs

01:51:05 Introducing Love Life: A Holistic Health Venture

01:57:18 The Importance of Whole Foods and Nutrition

02:08:09 Concluding Thoughts on Success and Happiness