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Win the Day

Win the Day

By: James Whittaker
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Ready to Win the Day®? Hosted by 3x bestselling author, James Whittaker, the Win the Day podcast was created to reveal how the world’s best performers Win the Day … and how YOU can, too. Featuring exclusive interviews with: • Billion-dollar founders • #1 NY Times bestselling authors • Medical experts • World champion athletes • Special forces operators • And more... Hit 'subscribe' and let's #WinTheDay 🚀James Whittaker Personal Development Personal Success
Episodes
  • 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!

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    🎬 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

    _

    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 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 🍿

    _

    Listening on Spotify?

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    Want to support the show?

    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 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

    _

    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 256: Happy Hustle with Cary Jack | Win the Day

    Show More Show Less
    1 hr and 10 mins
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