

Win the Day
James Whittaker
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 🚀
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 🚀
Episodes
Mentioned books

Oct 28, 2025 • 51min
260. Why Comfort Kills with Joe De Sena (NY Times bestselling author; founder, Spartan Race) 🏆
“Even if you’re on the right track, you’ll get run over if you just sit there.” — Will RogersJoe 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 Sena1:47 Interview starts3:22 The decision to start Spartan (purpose vs corporate world)5:22 Joe De Sena’s superpower7:48 Develop the ability to inspire others8:41 Why comfort kills (and the problem with laziness)11:11 Almost going bankrupt13:30 How Spartan saves lives16:28 The #1 way to get out of depression19:10 Your mental health depends on the people around you20:45 The hardest habit for people to change22:11 Why you’re failing with your health and fitness goals23:22 How Joe De Sena sets (and achieves) goals25:20 Are material possessions making you weak?27:38 How to become more resilient29:21 The toughest ultra events on the planet31:22 How to get through your most challenging moments32:46 How to know when enough is enough or if you're pushing too hard34:09 Earn your reward34:46 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 kids39:50 What sports to put your kids in40:49 Focus on hard work (not winning or losing)41:58 Joe De Sena family values43:30 How to make your kids more resilient45:23 Why parents need to model healthy behavior46:24 How to stop a bad day from coming into the home46:55 Affirmation47:40 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…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 248: Perform Under Fire with Leigh Anderson (paramedic)

Oct 22, 2025 • 10min
259. What Are You Chasing? 🏃♂️
“Poor is the pupil who does not surpass his master.” — Leonardo da VinciToo 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,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.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 💜#WinTheDayIn case you missed it: Episode 254: Win Monday with Paul Epstein

Oct 14, 2025 • 1h 10min
258. Wealthy & Well Known with Rory Vaden (NY Times bestselling author, speaker, and personal branding expert) 🧲
“Service to others is the rent you pay for your room here on Earth.” — Muhammad AliRory 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 starts2:18 Why everyone needs a personal brand3:32 How Rory and AJ Vaden launched Brand Builders Group with Lewis Howes7:32 How ALL wealthy people make their money10:05 Focus on the one problem you solve14:10 Become a master of the problem16:31 How to instantly get clear on who you should help19:08 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 life27:38 How Poppi became a $2 billion company28:48 The mindset of wealth creation35:31 How to become wealthy and well-known38:35 The #1 trait of the world’s most successful people46:15 Rory Vaden daily routine48:45 How to multiply your time50:45 How to balance marriage, parenting, and business52:18 Be okay with imperfection (80% done by someone else is better than 100% done right by you)57:57 Affirmation58:58 Rocket Round1:06:12 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…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 256: Happy Hustle with Cary Jack | Win the Day

Oct 8, 2025 • 8min
257. The Truth About Bad Days (and How to Win Them Anyway) ⚡️
"Life isn't as serious as the mind makes it out to be." — Eckhart TolleYou'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,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.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 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

Sep 30, 2025 • 53min
256. Happy Hustle with Cary Jack (author, podcaster, and founder of The Happy Hustle) 😊
“Choose a job you love, and you will never have to work a day in your life.” — ConfuciusCary 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 Jack1:29 Interview starts2:17 Focus on ONE thing at once4:50 Living a life that’s not yours7:15 Origins of The Happy Hustle 9:12 The 3 types of freedom we all need10:06 Should you stay in a corporate job or start a business13:35 4 questions to build your personal brand16:28 The “More Disease” (know when enough is enough)19:00 Why you’re burned out at work22:18 Know your MVTs (Most Valuable Tasks) every day24:31 The SOULMAPPIN Framework (an operating system for high performance)26:40 Get outdoors more often29:28 How to bring more joy to your life33:26 What it’s like living in Montana36:42 How becoming a parent changes your life — and your marriage38:50 Balance equals happiness40:45 Know what success means to you41:35 Lessons from the most successful people in the world43:40 The best wearable tech is your own mind46:02 Affirmation47:50 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…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 250: Masters of Uncertainty with Rich Diviney

Sep 24, 2025 • 19min
255. 11 Lifestyle Changes: What's In — and What's Out 🎡
"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,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Links and resources mentioned:Episode 233Episode 191Listening on Spotify?Leave a comment to share your thoughts.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 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

13 snips
Sep 16, 2025 • 1h 15min
254. Win Monday with Paul Epstein (author; sports leader; executive coach) 🏎️
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.

Sep 10, 2025 • 12min
253. What Conversation Are You Avoiding? 🤔
"Ultimately, the bond of all companionship, whether in marriage or friendship, is conversation." — Oscar WildeWhat'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,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.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 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

Sep 2, 2025 • 46min
252. Transform Your 20s — Helping Young Adults Thrive with Livi Redden (TED speaker, author) 🧠
“When you want something, all the universe conspires in helping you to achieve it.” ― Paulo Coelho (The Alchemist)Why are so many young people struggling to find their way? 🧐As someone who speaks at schools and universities, I’ve seen the mental health crisis up close—apathy, disconnection, and a lack of purpose are real.But one person is on a mission to change that for good...Livi Redden, a TED speaker (2.7M+ views), author, and passionate leader, is dedicated to empowering the next generation to live happy, resilient, and purpose-driven lives.Her mission began at 17, when she held her father’s hand as he passed after a six-year battle with ALS. That moment shaped her relentless drive to help others find peace and purpose.Through her work, Livi inspires young people to build lives they love and embrace who they truly are. It’s hard to imagine a more vital mission for today’s world.In this episode:• The biggest challenges facing young people today—and what to do about them.• How to embrace your full self, even when the world tells you to shrink.• The truth about grief, growth, and finding peace in the hardest moments.• Why your future is brighter—and more in your hands—than you realize.🍿Let’s WIN THE DAY with Livi Redden!_🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/252-win-the-day-podcast-livi-redden_Episode links:🎯 Download your FREE Win the Day action plan🎤 TEDx Talk ‘What Nobody Tells You About Your Twenties’ by Livi Redden📱 Livi Redden TikTok🤝 Livi Redden online community ‘The Sooner, The Better’📚 ‘The Sooner You Know, The Better’ by Livi Redden⚡ Livi Redden website📷 Livi Redden Instagram🎬 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 Livi Redden1:39 Interview starts2:28 When Livi Redden’s father was diagnosed with ALS3:39 Caring for someone with ALS or chronic health issues9:21 How to find the gift in pain11:35 Leveraging pain to find your mission12:38 Life in your 20s (use intention to improve the quality and trajectory of your life)14:24 What teens and young adults struggle with most today (and why your relationship with yourself is most important)16:41 How high schools can be improved20:42 Best advice for young people22:24 What teenagers want from their parents24:26 How parents can encourage their children to open up more27:03 How to become more confident28:40 How your past is holding you back31:22 Take radical responsibility33:00 How Livi Redden secured a TED Talk and made it go viral (2.7M+ views)38:14 Affirmation39:46 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 208: The Gift of Pain with Brian Bogert

Aug 27, 2025 • 9min
251. What to Do When You Feel Stuck (or Miserable) 🤔
“Happiness is not something ready-made. It comes from your own actions.” – Dalai LamaAre you feeling stuck in your life? Maybe it's a job you're disengaged from, the overwhelm of a young family, or caring for an aging parent.In this minisode, we'll go through a 3-step plan to take back control of your happiness — and your life. Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.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 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney


