Win The Day With James Whittaker

"It always seems impossible until it's done." — Nelson MandelaThe promise of this episode is to help you achieve literally any goal you set for yourself. Sounds pretty lofty, right?

"The only thing necessary for the triumph of evil is for good men to do nothing." — Edmund BurkeDean Stott served in one of the world’s most elite special forces units, the British SBS (Special Boat Service).In a 16-year military career, Dean deployed to the planet’s most hostile environments, tackled counter-terrorism operations, and lived the unrelenting pursuit of excellence.In 2011, a parachuting accident ended his military career, but Dean didn’t slow down. He became a world-leading security consultant, protecting presidents, royal families, and governments—even evacuating the Canadian Embassy in Libya in 2014 and rescuing over 200 people from Israel in 2023.Then, with barely 20 miles of cycling experience, Dean set out to break two world records by biking the 14,000-mile Pan American Highway from Argentina to Alaska in under 100 days. He did it—raising over $1.4 million for mental health charities along the way.In 2024, Dean was awarded the MBE (Member of the Order of the British Empire).Dean

“An hour of planning can save you 10 hours of doing.” — Dale CarnegieThere’s been a trend sweeping the world and that’s cold exposure.In the busy world we’re in today, more and more people are connecting back to these ancient traditions that help us feel our best.Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! ⁠⁠⁠Join 23K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

“It's very simple; just look at your life to see where you're heading. You're always in a momentum of something.” ― Maria ErvingWe're four weeks into 2026, and I have a question for you: How are those New Year's resolutions going?If you're like most people, the initial excitement has already started to fade. The clarity you had a few weeks ago is already getting cloudy.In this minisode, I'm going to show you how winners plan their year so, even if you're off to a tough start, you can still finish strong. Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! ⁠⁠Join 23K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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“Your time is limited, so don't waste it living someone else's life.” — Steve JobsDan Martell is author of acclaimed book ‘Buy Back Your Time,' an angel investor, and thought leader to 10M+ social media followers. In his early years, Dan faced addiction and jail time, but made an extraordinary turnaround. Today, he's recognized as a guiding light for entrepreneurs worldwide, assisting them in building thriving businesses while strengthening their mindset.Dan is also a proud husband and father of two.In the last two years, Dan’s public profile has skyrocketed, and he reveals the secrets to that growth in this episode.In this episode:• The inspiring words that turned Dan’s entire life around.• How to build a life that gives you energy.• The secrets to a happy marriage and household.• The most important skills your children need to succeed.• How to upgrade your career for more time, money, and freedom.This might be the most value-packed episode of the Win the Day podcast ever released.Let’s WIN T

"Success seems to be largely a matter of hanging on after others have let go." — William FeatherIn this minisode, we'll go through a 5-step plan to finish the year strong—and set you up to make 2026 your best year yet.Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! ⁠Join 23K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

“What you do speaks so loudly that I cannot hear what you say.” — Ralph Waldo EmersonLet's recap the most powerful moments of the Win the Day podcast in 2025!Hopefully, like me, you’ve learned a lot, but most importantly you’ve taken ACTION on what you’ve learned.If you missed the recap for the first half of the year, check out Episode 244.What's your favorite tip? Leave a comment to let us know.Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! ⁠⁠Join 23K+ other YouTube subscribers⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

"We make a living by what we get, but we make a life by what we give." — Winston ChurchillWelcome to our annual holiday gift guide!These are the items that have made the biggest impact on my life throughout the year, and I know they’ll do the same for you or for someone else if you’re giving them as a gift.What made the biggest difference in your life this year? Leave a comment to let us know.Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! ⁠Join 23K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

“The most common way people give up their power is by thinking they don’t have any.” —  Alice WalkerRoma Van der Walt, MSc, is a sport scientist, former pro athlete, and one of the leading voices in the future of female physiology.As the founder and CEO of Vitelle, Roma is building the first scalable health intelligence platform designed specifically for women—translating complex physiology into actionable insights for sport, clinical care, and preventive health.With a background that spans elite competition (including seven years representing Germany in the pentathlon), humanitarian work at the UN, and digital product design, Roma brings a rare systems-thinking approach to women’s health.Her mission is to finally close the data gap in how female biology is understood and supported across every stage of life.In this episode:• The biggest myths about performance, recovery, and hormones.• How to design your daily routine for strength, energy, and longevity.• Why female health data is still shockingly underused.

“I don’t need to change the world overnight. I'm going to change the world over the next 50 years." — Jensen HuangNvidia CEO Jensen Huang built a trillion-dollar company on a simple philosophy: win today so you can play again tomorrow. In this minisode, we unpack his viral insight about why executing flawlessly on simple plans beats chasing perfection, and how this approach transforms both your business and your daily life.Onward,JamesPS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ We just passed 10M+ views on YouTube! Join 23K+ other subscribers on YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

“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.

“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

“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.

"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

“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 ul

"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

“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 wo

"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

“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?