Win the Day

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254. Win Monday with Paul Epstein (author; sports leader; executive coach) 🏎️

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Sep 16, 2025

Guest

Paul Epstein

Paul Epstein, a two-time bestselling author and renowned speaker, shares his expertise in turning high-pressure moments into momentum. He emphasizes how to transform Mondays into powerful launchpads for the week. Paul discusses the importance of clarity in decision-making during tough times and the need to foster a proactive team culture. He advocates for personal accountability and outlines strategies for effective morning routines, encouraging listeners to embrace feedback and build strong emotional connections in leadership.

01:14:35

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ANECDOTE

Loss That Shaped His Why

Paul lost his father at 19 and felt forced into adulthood which reshaped his purpose.
Meeting his dad's former students who credited his father with giving them hope anchored Paul's mission to impact others.

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ADVICE

Use FBI For Memorable Feedback

Use the FBI formula: describe Feelings, Behavior, and Impact when giving recognition or feedback.
Make people remember how you made them feel, not just the behavior or result.

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ADVICE

Make One Monday Decision

Pick one action each Monday that makes the day a win to start momentum for the week and beyond.
Stack weekly wins to compound into winning months, quarters, and years.

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The Lasting Legacy of Family and Mentorship

01:35 • 4min

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The Power of Feedback and Emotional Connection in Leadership

05:50 • 3min

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Winning Mondays and Beyond

09:02 • 23min

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The Power of Daily Recommitment and Preparing for Success

Intentional Decision-Making for Personal Growth

Napoleon Hill's 'Think and Grow Rich' outlines a philosophy of personal achievement based on the power of positive thinking. Hill presents thirteen principles that, when followed, can lead to financial success. These principles include desire, faith, autosuggestion, specialized knowledge, imagination, organized planning, decision, persistence, power of the mastermind, the mystery of sex transmutation, the subconscious mind, the brain, and the sixth sense. The book encourages readers to define their goals, develop a strong desire to achieve them, and maintain unwavering faith in their ability to succeed. Through case studies and practical exercises, Hill aims to empower individuals to transform their thoughts into tangible wealth.

#46589

Better Decisions Faster

Paul Epstein

• Mentioned in 365 episodes

The obstacle is the way

Ryan Holiday

In 'The Obstacle Is the Way', Ryan Holiday presents a framework for turning obstacles into successes. Drawing from the philosophy of Stoicism and the writings of Marcus Aurelius, Holiday outlines three disciplines: perception, action, and will. He illustrates these principles with historical anecdotes from figures such as John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, and Steve Jobs. The book emphasizes the importance of perception in shaping one's response to obstacles, the need for intentional and creative action, and the cultivation of will to persist through challenges. Holiday argues that by adopting these Stoic principles, individuals can transform their obstacles into opportunities for growth and success.

#17

• Mentioned in 268 episodes

Essentialism

The Disciplined Pursuit of Less

Greg McKeown

In 'Essentialism: The Disciplined Pursuit of Less,' Greg McKeown argues that by applying a more selective criteria for what is essential, individuals can regain control of their time and energy. The book is divided into sections such as Explore, Eliminate, and Execute, providing practical advice on distinguishing the vital few from the trivial many and eliminating non-essential activities. McKeown emphasizes the importance of clarity of focus, the ability to say 'no,' and living 'by design, not by default. ' This approach helps readers achieve more by doing less and making the highest possible contribution in their personal and professional lives.

“Every morning you have two choices: Continue to sleep with your dreams or wake up and chase them.” — Carmelo Anthony

Paul Epstein has mastered the art of turning high-stakes pressure into unstoppable momentum.

After 15 years as a top sports executive with NFL and NBA teams, a global agency, and the NFL league office, Paul shattered Super Bowl revenue records, opened a billion-dollar stadium, and launched the San Francisco 49ers Talent Academy—earning him the nickname “The Why Coach.”

Today, Paul is a 2x bestselling author, award-winning speaker, and trusted advisor to some of the world’s most elite teams and companies, including Amazon, Disney, NASA, and the LA Lakers.

His mission? To help people and organizations Win Monday—and build cultures that lead from purpose, not pressure. Clearly an aligned mission with the Win the Day podcast!

In this episode:

• The power of turning Monday into momentum.

• How to find clarity at your scariest fork in the road.

• Why "playing offense" is the key to thriving in a reactive world.

• How to create a team of leaders—not just a leadership team.

🍿 Let’s WIN THE DAY with Paul Epstein!

🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/254-win-the-day-podcast-paul-epstein

Episode links:

🎯 Download your FREE Win the Day action plan

⚡ Paul Epstein website

📷 Paul Epstein Instagram

♾️ Paul Epstein LinkedIn

📚 ‘Better Decisions Faster’ by Paul Epstein

🎬 Subscribe to ⁠Win the Day YouTube⁠ channel

💚 Give the Win the Day podcast a ⁠5-star rating on Apple Podcasts⁠

🙏 Give the Win the Day podcast a ⁠5-star rating on Spotify⁠

Timemarkers:

00:00 Who is Paul Epstein

1:34 Interview starts

3:30 The importance of having a hero in your life

4:55 Have a reason to think tomorrow is worth it

6:42 Why you need strong relationships

8:03 The FBI Formula (Feelings, Behavior, Impact)

10:38 What “Win Monday” means

13:25 The #1 attitude the most elite performers have

15:05 How most people feel about Monday

17:18 Understanding the most important things in your life

19:17 Win the game of life (“love both planes”)

24:09 Your life is bigger than you

27:38 The secret to motivation (do it for your hero)

34:35 Does winning the day start the night before?

38:02 Win your morning, win your life

40:28 How to Win the Day (and journal template to win the day)

46:40 Winning has a compounding effect

50:20 When people feel good, they play good

51:10 Daily routine to win the day

54:17 Be intentional with your environment

56:16 How to make better decisions (Head, Heart, Hands)

58:46 How to handle bad days

1:03:55 Affirmation

1:05:55 Rocket Round

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Thank you for your support! It truly means a lot 💕

Onward and upward always…

#WinTheDay

PS — Enjoyed this episode? You'll love this one, too:⁠⁠⁠ Episode 250: Masters of Uncertainty with Rich Diviney

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