Episode 254

Win Monday with Paul Epstein | Win the Day

September 16, 2025

Paul Epstein is a 2x bestselling author, award-winning speaker, and advisor to Amazon, Disney, and NASA. His mission is to help people Win Monday.

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In this episode of Win the Day:

“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 (The Power of Playing Offense, Better Decisions Faster), 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.

In this episode:
• How to create a team of leaders—not just a leadership team.
• The power of turning Monday into momentum.
• Why "playing offense" is the key to thriving in a reactive world.
• How to find clarity at your scariest fork in the road.

Let’s WIN THE DAY with Paul Epstein!

Timestamps

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

Resources / links mentioned:

🎯 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

💕 Win the Day Facebook group

📝 Win the Day newsletter [weekly LinkedIn exclusive]

Inspiring quotes in this episode:

"I've always had the right people behind me, supporting me, challenging me." — Paul Epstein
"The standard of excellence all champions have is they are willing to do what others won't." — Paul Epstein
"Make Monday a winning day. You now have momentum to not just win the next day but to win the week. Stack weeks, you have momentum to win the month, you win quarters, and eventually you look back after having your most winning year yet — and it all started because you locked in on one decision, one strategy, one commitment to Win Monday." — Paul Epstein
"I love the plane to go fulfill my impact in the world, and I love the plane to come home. So my personal definition of happiness and fulfillment is, 'Love both planes.' When you love both planes, it's a full life. It's a whole life. It's a beautiful life. That is a winning life." — Paul Epstein
"If it was the week from hell where everything just went against you, what an amazing opportunity to just flip the page, hit the reset button and say, 'I can't do anything about last week.'" — Paul Epstein
"We will let ourselves down before we let the most important person in our life down." — Paul Epstein
"When you simplify your life to making your hero proud, you literally can't lose." — Paul Epstein
"The gap was never gifts, talents, abilities, or skills. It was this inner sense of unshakable confidence versus what I call blue skies confidence." — Paul Epstein
"Own your morning and you own your life." — Paul Epstein
"While everybody else wastes Monday, you decide, you choose, you commit to Win Monday. That's the law of separators. That is you doing what other people simply will not." — Paul Epstein
"Stop wasting Mondays and start winning them." — Paul Epstein
"When people feel good, they play good." — Paul Epstein
"You need to be intentional with your environment." — Paul Epstein
"The losses are not always our fault, but we can make them our responsibility." — Paul Epstein
"When you are warm, it makes the people around you warm." — Paul Epstein

Download Full Episode Transcript

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