• 260. Why Comfort Kills with Joe De Sena (NY Times bestselling author; founder, Spartan Race) 🏆
    Oct 28 2025

    Even if you’re on the right track, you’ll get run over if you just sit there.” — Will Rogers

    Joe De Sena is a New York Times bestselling author, fitness icon, and the founder of Spartan—a global movement that’s transformed 15M+ lives through its world-renowned endurance events and lifestyle programs.

    After a successful corporate career, Joe left it all behind to pursue a more meaningful mission: to get 100 million people off the couch. What started as a few races in Vermont has exploded into a global fitness phenomenon, with over 1M+ participants across 40+ countries every year.

    Joe has personally completed more than 50 ultra-events, even completing 14 Ironmans in a single year. He now trains others to build mental toughness, embrace discomfort, and live with purpose.

    In this episode:

    • How to strengthen your mindset through physical challenges.

    • The daily discipline behind elite performance.

    • Why modern life makes us soft — and what to do about it.

    • How to build a healthy, loving, and resilient family.

    🍿 Let’s WIN THE DAY with Joe de Sena!

    _

    🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/260-win-the-day-podcast-joe-de-sena

    _

    Episode links:

    🎯 Download your FREE Win the Day action plan

    ⚡ Joe de Sena website

    📷 Joe de Sena Instagram

    📝 Joe de Sena Facebook

    🎬 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 Joe De Sena

    1:47 Interview starts

    3:22 The decision to start Spartan (purpose vs corporate world)

    5:22 Joe De Sena’s superpower

    7:48 Develop the ability to inspire others

    8:41 Why comfort kills (and the problem with laziness)

    11:11 Almost going bankrupt

    13:30 How Spartan saves lives

    16:28 The #1 way to get out of depression

    19:10 Your mental health depends on the people around you

    20:45 The hardest habit for people to change

    22:11 Why you’re failing with your health and fitness goals

    23:22 How Joe De Sena sets (and achieves) goals

    25:20 Are material possessions making you weak?

    27:38 How to become more resilient

    29:21 The toughest ultra events on the planet

    31:22 How to get through your most challenging moments

    32:46 How to know when enough is enough or if you're pushing too hard

    34:09 Earn your reward

    34:46 Joe De Sena parenting approach (always take the hard way with your kids)

    35:42 Are you putting too much pressure on your kids?

    39:03 Celebrate hard work with your kids

    39:50 What sports to put your kids in

    40:49 Focus on hard work (not winning or losing)

    41:58 Joe De Sena family values

    43:30 How to make your kids more resilient

    45:23 Why parents need to model healthy behavior

    46:24 How to stop a bad day from coming into the home

    46:55 Affirmation

    47:40 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 248: Perform Under Fire with Leigh Anderson (paramedic)

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    51 mins
  • 259. What Are You Chasing? 🏃‍♂️
    Oct 22 2025

    Poor is the pupil who does not surpass his master.” — Leonardo da Vinci

    Too many of us are living a life we don't want, or destroying our inner piece, out of obligation to someone else.

    In this minisode, we'll look at why you should run your own race—and how inner piece is quickly becoming the real metric of success.

    Onward,

    James

    PS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join 20K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🍿

    _

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    🙏 Leave a 5-star rating on Spotify: ⁠⁠https://spoti.fi/3cKIDT6⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    Loving the episode? Share it with a friend so they can benefit, too.

    _

    Your support is greatly appreciated 💜

    #WinTheDay

    In case you missed it: ⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Episode 254: Win Monday with Paul Epstein

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    10 mins
  • 258. Wealthy & Well Known with Rory Vaden (NY Times bestselling author, speaker, and personal branding expert) 🧲
    Oct 14 2025

    Service to others is the rent you pay for your room here on Earth.” — Muhammad Ali

    Rory Vaden is a New York Times bestselling author, Hall of Fame speaker, and co-founder of Brand Builders Group.

    As the world’s leading expert on personal branding, Rory helps people clarify their message, amplify their impact, and turn influence into income.

    Rory's work has been instrumental in guiding the careers of top performers like Lewis Howes, Ed Mylett, Amy Porterfield, and Eric Thomas. His TEDx Talk has 5M+views, and his new book Wealthy and Well-Known has just been released.

    In this episode:

    • How to build an influential personal brand, regardless of profession.

    • The biggest mistakes people make in sharing their story.

    • What’s stopping you from achieving financial freedom.

    • Why the secret to happiness is in being of service to others.

    🍿 Let’s WIN THE DAY with Rory Vaden!

    _

    🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/258-win-the-day-podcast-rory-vaden

    _

    Episode links:

    📚 Download your FREE audiobook ‘Wealthy and Well Known’ by Rory & AJ Vaden

    ⚡ Rory Vaden website

    📈 Brand Builders Group

    📷 Rory Vaden Instagram

    🎤 TEDx Talk ‘How To Multiply Your Time’ by Rory Vaden

    🎯 Download your FREE ⁠Win the Day action plan

    🎬 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 Rory Vaden1:28 Interview starts

    2:18 Why everyone needs a personal brand

    3:32 How Rory and AJ Vaden launched Brand Builders Group with Lewis Howes

    7:32 How ALL wealthy people make their money

    10:05 Focus on the one problem you solve

    14:10 Become a master of the problem

    16:31 How to instantly get clear on who you should help

    19:08 How to own—and believe in—your story (and instantly build your credibility)

    22:39 The right metrics for success (and how to build trust)

    26:25 The best form of marketing is a changed life

    27:38 How Poppi became a $2 billion company

    28:48 The mindset of wealth creation

    35:31 How to become wealthy and well-known

    38:35 The #1 trait of the world’s most successful people

    46:15 Rory Vaden daily routine

    48:45 How to multiply your time

    50:45 How to balance marriage, parenting, and business

    52:18 Be okay with imperfection (80% done by someone else is better than 100% done right by you)

    57:57 Affirmation

    58:58 Rocket Round

    1:06:12 How to master your thoughts

    _

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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 256: Happy Hustle with Cary Jack | Win the Day

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    1 hr and 10 mins
  • 257. The Truth About Bad Days (and How to Win Them Anyway) ⚡️
    Oct 8 2025

    "Life isn't as serious as the mind makes it out to be." — Eckhart Tolle

    You'll never be able to escape to a tough day, but can you learn how to master it.

    Join me for a brand new minisode for the truth about tough days—and how to win them anyway.

    Onward,

    James

    PS —⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join 20K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🍿

    _

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    Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.

    💕 Leave a review on Apple Podcasts:⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://apple.co/3b29Q2U⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    🙏 Leave a 5-star rating on Spotify: ⁠https://spoti.fi/3cKIDT6⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    Loving the episode? Share it with a friend so they can benefit, too.

    _

    Your support is greatly appreciated 💜

    #WinTheDay

    In case you missed it: ⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

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    8 mins
  • 256. Happy Hustle with Cary Jack (author, podcaster, and founder of The Happy Hustle) 😊
    Sep 30 2025

    Choose a job you love, and you will never have to work a day in your life.” — Confucius

    Cary Jack is the founder of The Happy Hustle, a top-ranked podcast and movement dedicated to helping people achieve balance, freedom, and purpose.

    After burning out as a tech entrepreneur, Cary made a radical shift — trading 80-hour weeks for a 20-hour workweek that still generates millions in revenue.

    Now, through his bestselling book, wilderness masterminds, and global stage presence, Cary is showing people how to align their work with their well-being. In doing so, Cary has proven that you don’t have to sacrifice health and happiness to achieve big goals — you just have to rethink your approach.

    Cary lives in Bozeman, Montana, with his wife and son, where he can be found fly fishing for rainbows, riding his noble steed, and snowboarding fresh powder.

    In this episode:

    • The “More Disease” and how to fill yourself with gratitude.

    • The limiting beliefs holding you back from the life you want.

    • Why energy and health are your ultimate performance levers.

    • How to bring more happiness into each and every day.

    🍿 Let’s WIN THE DAY with Cary Jack!

    _

    🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/256-win-the-day-podcast-cary-jack

    _

    Episode links:

    🎯 Download your FREE Win the Day action plan

    ⚡ Cary Jack website

    📷 Cary Jack Instagram

    📚 ‘The Happy Hustle’ by Cary Jack

    🎤 The Happy Hustle Podcast by Cary Jack

    🎬 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 Cary Jack

    1:29 Interview starts

    2:17 Focus on ONE thing at once

    4:50 Living a life that’s not yours

    7:15 Origins of The Happy Hustle

    9:12 The 3 types of freedom we all need

    10:06 Should you stay in a corporate job or start a business

    13:35 4 questions to build your personal brand

    16:28 The “More Disease” (know when enough is enough)

    19:00 Why you’re burned out at work

    22:18 Know your MVTs (Most Valuable Tasks) every day

    24:31 The SOULMAPPIN Framework (an operating system for high performance)

    26:40 Get outdoors more often

    29:28 How to bring more joy to your life

    33:26 What it’s like living in Montana

    36:42 How becoming a parent changes your life — and your marriage

    38:50 Balance equals happiness

    40:45 Know what success means to you

    41:35 Lessons from the most successful people in the world

    43:40 The best wearable tech is your own mind

    46:02 Affirmation

    47:50 Rocket Round

    _

    Want to support the show?

    1. Hit 'Follow'.

    2. Leave a 5-star rating.

    3. Share this episode with a friend.

    This will help the podcast get discovered by more people so they can Win the Day, too.

    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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    53 mins
  • 255. 11 Lifestyle Changes: What's In — and What's Out 🎡
    Sep 24 2025

    "They always say time changes things, but you actually have to change them yourself." — Andy Warhol

    We all have those things that we love, but isn't variety the spice of life?

    In this minisode, I share what's in and what's out for this season of my life.

    What are some changes you've been making? Drop a comment and let us know.

    Onward,

    James

    PS —⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join 20K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🍿

    _

    Links and resources mentioned:

    Episode 233

    Episode 191

    Listening on Spotify?

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    Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.

    💕 Leave a review on Apple Podcasts:⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://apple.co/3b29Q2U⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    🙏 Leave a 5-star rating on Spotify: ⁠https://spoti.fi/3cKIDT6⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    Loving the episode? Share it with a friend so they can benefit, too.

    _

    Your support is greatly appreciated 💜

    #WinTheDay

    In case you missed it: ⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

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    19 mins
  • 254. Win Monday with Paul Epstein (author; sports leader; executive coach) 🏎️
    Sep 16 2025
    “Every morning you have two choices: Continue to sleep with your dreams or wake up and chase them.” — Carmelo AnthonyPaul 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 Epstein1:34 Interview starts3:30 The importance of having a hero in your life4:55 Have a reason to think tomorrow is worth it6:42 Why you need strong relationships8:03 The FBI Formula (Feelings, Behavior, Impact)10:38 What “Win Monday” means13:25 The #1 attitude the most elite performers have15:05 How most people feel about Monday17:18 Understanding the most important things in your life19:17 Win the game of life (“love both planes”)24:09 Your life is bigger than you27:38 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 life40:28 How to Win the Day (and journal template to win the day)46:40 Winning has a compounding effect50:20 When people feel good, they play good51:10 Daily routine to win the day54:17 Be intentional with your environment56:16 How to make better decisions (Head, Heart, Hands)58:46 How to handle bad days1:03:55 Affirmation1:05:55 Rocket Round_Want to support the show?1. Hit 'Follow'.2. Leave a 5-star rating.3. Share this episode with a friend.This will help the podcast get discovered by more people so they can Win the Day, too.Thank you for your support! It truly means a lot 💕Onward and upward always…#WinTheDayPS — Enjoyed this episode? You'll love this one, too:⁠⁠⁠ Episode 250: Masters of Uncertainty with Rich Diviney
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    1 hr and 15 mins
  • 253. What Conversation Are You Avoiding? 🤔
    Sep 10 2025

    "Ultimately, the bond of all companionship, whether in marriage or friendship, is conversation." — Oscar Wilde

    What's the fastest way to close the gap between your life today and your potential? Have the conversation you've been avoiding.

    In this minisode, we'll get clear on exactly what this is for you—and how to confront it, once and for all...

    Onward,

    James

    PS —⁠⁠⁠⁠⁠⁠⁠⁠ Join 20K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 🍿

    _

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    Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.

    💕 Leave a review on Apple Podcasts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://apple.co/3b29Q2U⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

    Loving the episode? Share it with a friend so they can benefit, too.

    _

    Your support is greatly appreciated 💜

    #WinTheDay

    In case you missed it: ⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

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    12 mins