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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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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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

Rob Fraser unveils the untold story of OUTWAY—from hawking socks on street corners to building an eight-figure empire. Surviving near-catastrophic business crises, he leveraged lessons from his professional sports career to navigate the business world. Discover the counterintuitive mental models that transformed a world-class athlete into a business maverick, turning the humble sock into a ten-million-dollar revolution.

As a special offer to listeners, the TKP community can get 30% off using the code SHANE at checkout. https://outway.com/

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Through contrarian thinking and patient capital deployment, John Bragg built two multi-billion-dollar businesses from a remote village.

John Bragg is the entrepreneur behind Oxford Frozen Foods, which processes over 50% of the world's wild blueberries, and Eastlink Communications, the largest private telecommunications company in North America.

This epside isn't about startup hacks but the timeless principles behind building multi-generational businesses that operate through good and bad times.

Shane and John discuss how he transformed a commodity agriculture business into a global leader and launched an unlikely telecommunications empire. This episode offers a rare glimpse into the strategic mind of one of North America's most private (and successful) business leaders.

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When Princeton-educated attorney Erin Wade left law to open a restaurant, she didn't just create award-winning comfort food—she engineered a revolutionary workplace culture. This conversation reveals how she transformed an Oakland mac and cheese restaurant into a laboratory for modern management principles.

Wade shares her groundbreaking 'color code of conduct' system (now adopted globally) and her radical approach to open-book management. A masterclass in building culture, solving industry-wide challenges, and leading with precision rather than convention.

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(00:00) Intro

(02:30) Wade's surfing obsession

(04:42) Defeating overthinking

(05:00) Wade's background in food

(06:40) Wade's law detour

(10:20) On being fired

(12:40) Early mistakes and freedom

(20:00) Employee-centric companies

(32:30) Homeroom Hard Times

(34:40) How Wade's law background helped (and hurt)

(42:40) The Color Code of Conduct

(49:30) Why Wade sold Homeroom (and how she felt)

(55:58) Impact vs. Intent

(59:00) Why titles are important

(01:04:00) On success

Matthew Dicks reveals the sophisticated frameworks behind storytelling mastery—an essential skill for leaders who need to persuade, inspire, and drive change. Far from basic presentation tips, this conversation deconstructs the psychological elements that make stories an instrument of influence.

Learn the strategic principles of narrative architecture that separate forgettable anecdotes from stories that reshape boardrooms, pitch meetings, and executive communications. A masterclass in wielding one of leadership's most powerful but least understood tools.

(00:00:00 Intro

(00:03:28) What makes a good story

(00:06:57) Stories vs anecdotes

(00:08:29) A Story: The Spoon of Power

(00:17:42) The art of story architecture

(00:21:28) Create compelling stories

(00:36:30) Common mistakes & how to fix them

(00:55:01) Strategic Listening

(01:03:32) Can you lie in stories?

(01:05:10) 'And' stories vs. 'but / therefore' stories

(01:10:05) Finding engaging stories in everyday life

(01:20:05) Structuring a story

(01:24:00) Storytelling for an unforgettable brand

(01:31:20) Learn confidence

(01:38:40) Writing vs telling a story

(01:51:53) Teach kids to love writing

(01:55:15) Define success

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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Former IBM executive April Dunford reveals the sophisticated frameworks behind market leadership. This isn't about marketing tactics but how category leaders reshape markets to their advantage.

Drawing from decades of experience, Dunford shares the nuanced art of market definition, competitive positioning, and strategic narrative. These are essential insights for leaders who understand that winning isn't about being better—it's about being different in meaningful ways.

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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/

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.

Follow me: ⁠⁠⁠⁠⁠⁠⁠⁠https://beacons.ai/shaneparrish⁠⁠⁠⁠⁠⁠⁠⁠

Timestamps:

(00:00) Intro

(02:07) Positioning, explained

(16:47) Why is positioning important?

(20:40) B2B vs. B2C positioning

(29:03) When re-positioning a product failed

(32:31) How to identify customer's pain points

(34:35) How to position a product on a sales page

(38:06) How technology has changed positioning

(41:40) How to evaluate product positioning

(45:43) Who's in charge of positioning at a company?

(50:27) On storytelling

(56:35) Should a company have a point of view on the market?

(1:00:21) Dealing with gatekeepers in B2B marketing

(1:03:02) Mistakes people make with positioning

(1:05:21) What schools get wrong about marketing

(1:08:59) Secrets of B2B decision-making

(1:11:18) On success