

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 29, 2024 • 57min
210. Better Than Perfect with Dr. Greg Chasson 🗝️
“A good plan executed now is better than a perfect plan next week.” – George S. Patton
Do you ever feel the pressure to make everything perfect? 🧐
Today's guest, Dr. Greg Chasson, is here to help you break free from the perfectionism trap, reduce stress, and unlock a whole new level of productivity.
With over 20 years of experience treating obsessive-compulsive disorder (OCD), anxiety, and high-functioning autism, Dr. Chasson has helped countless people overcome the mental roadblocks of perfectionism.
He’s authored 70+ scientific publications, edited The Behavior Therapist journal, and recently released his groundbreaking book, FLAWED.
We’ll also go through:
• How to identify the values that drive your behaviors.
• How to raise high-achieving children.
• How to upgrade the productivity and happiness of all those around you.
• Why embracing your flaws could be the best thing that ever happened to you.
Let’s WIN THE DAY with Dr. Greg Chasson!
_
🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/210-win-the-day-podcast-greg-chasson
_
Episode links:
🎯 Download your FREE Win the Day action plan
📚 ‘FLAWED: Why Perfectionism is a Challenge for Management’ by Greg Chasson
⚡ Greg Chasson website
📷 Greg Chasson 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 Dr. Greg Chasson
1:49 Interview starts
2:29 You are what you study
3:30 Overcoming severe OCD
5:16 Toughest days as a psychologist
6:38 Don’t work harder than the patient
8:26 How to get clear on your values
10:54 How to see the good in everyone
12:45 How to help someone change their behavior
15:35 Managing perfectionism in the workplace
16:46 Are people born with perfectionism?
18:13 How to know if you’re a perfectionist
20:30 How to make better decisions in life (The Emphasis Framework)
22:28 When perfectionism becomes a problem
24:55 Perfectionism in special forces operators
27:33 Why action is better than perfectionism
29:38 Download your FREE Win the Day Action Plan
30:30 Change yourself before you change the world
32:28 Anxiety in the workplace
34:03 Should kids receive participation awards?
36:46 Do hard things
39:10 Imposter syndrome
40:37 How environment impacts self-esteem
41:46 How to help a kid who’s a perfectionist (plus anxiety and depression)
46:34 Working with who kids who have autism
48:03 How to balance success in the future with happiness in the present
50:26 Affirmation
50:57 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: The Gift of Pain with Brian Bogert: Ep 208

Oct 23, 2024 • 10min
209. Live Your Legacy (A Tribute to Kerwin Rae) 🕊️
“That’s the beautiful thing about being human — we all have the ability to transform.” — Kerwin Rae
Last week we lost a legend, Kerwin Rae...
Kerwin was a larger than life business leader who impacted millions around the world.
In this minisode, we'll explore the most defining moment of his life — and why legacy is something you live, not something you leave.
Check in on your loved ones 💗
Onward,
James
_
Show links:
🍿 Becoming Unstoppable with Kerwin Rae: Ep 31
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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: The Gift of Pain with Brian Bogert: Ep 208

5 snips
Oct 15, 2024 • 1h 1min
208. The Gift of Pain with Brian Bogert 🎨
Brian Bogert, resilience expert and inspiring speaker, shares his incredible journey from a traumatic childhood accident to helping others unlock their potential. He discusses how embracing pain can prevent future suffering and motivates listeners to live life to the fullest. Brian also emphasizes the importance of balancing family life with career aspirations and offers insights on emotional awareness in parenting. His personal story serves as a powerful reminder that our challenges can lead to remarkable growth and resilience.

Oct 9, 2024 • 15min
207. The Best Lessons from the Win the Day Mastermind 🔋
“There’s always room at the top for the best.” – Dr. Jeff Spencer
We just wrapped up the 2024 Win the Day Mastermind! In this minisode, I'm going to share three of the most impactful lessons to help you win.
Onward,
James
_
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.
_
Show links:
🙌 Enrol in the Win the Day Accelerator
🏆 Human mind vs champion mind card
_
Your support is greatly appreciated 🙏
#WinTheDay
In case you missed it: The Champion’s Path with Dr. Jeff Spencer : Ep 134

Oct 1, 2024 • 1h 20min
206. Your Richest Life with Garrett Gunderson 💰 (NY Times bestselling author; personal finance expert)
“The only limit to our realization of tomorrow is our doubts of today.” – Franklin D. Roosevelt
To create real wealth for yourself, you must first understand the rules of how the money game is played.
Garrett Gunderson knows them better than most…
Known for his unique approach to wealth creation and life design, Garrett is the author of 10 books, including the New York Times bestseller Killing Sacred Cows.
Garrett is an acclaimed speaker who uses entertainment to educate his audience. His comedy special The American Ream (not a typo!) breaks down all the myths about money and covers everything from the stock market and retirement to crypto-currency.
When he’s not writing or speaking, Garrett runs Cash Cabin immersions where he helps people build their Family Office, Family Constitution, and teaches them how to create their richest life.
In this episode:
• How to turn a poverty cycle into generational wealth.
• The biggest mistakes people make with their money.
• Why discovering your own value is the ultimate foundation.
• How to create your richest life.
Let’s WIN THE DAY with Garrett Gunderson!_
🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/206-win-the-day-podcast-garrett-gunderson
_
Episode links:
🎯 Download your FREE Win the Day action plan
⚡ Garrett Gunderson website
📷 Garrett Gunderson Instagram
📚 Books by Garrett Gunderson
🎬 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 Garrett Gunderson
1:40 Interview starts
4:45 How to prepare for standup comedy
9:45 Growing up with a poverty mindset
11:52 What’s wrong with young people today
14:44 How to grow a strong mindset
17:11 How to become friends with wealthy people
23:09 Why Garrett Gunderson began to focus on personal finance
25:35 How families like the Rockefellers build generational wealth
27:04 Why people make bad financial decisions
30:15 Find the win in the work
32:42 Download your FREE Win the Day Action Plan
33:31 How to connect with the frequency of wealth (and not fall victim to the trappings of wealth)
37:12 The biggest mistakes in entrepreneurship
41:08 How to design a life you love
44:20 How to balance career and family
47:31 3 steps for a happy, loving and connected family
54:15 Encourage your kids to launch a business at 14 years old
56:39 The best tip for productivity (pursue something you love)
58:33 How to turn financial freedom into generational wealth
1:02:26 Classroom vs the real world
1:03:43 How corrupt is the government?
1:06:53 Personal responsibility vs government intervention (and ‘The Ascent of Money’ by Niall Ferguson)
1:09:26 Why healthcare is so expensive — and how to fix it
1:13:25 The problem with cash handouts
1:14:26 Affirmation
1:14:53 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: How to Scale Success with Graham Weaver: Ep 200

Sep 25, 2024 • 9min
205. Visualize Your Success 🔮
“Ask for what you want and be prepared to get it.” — Maya Angelou
I moved to the US (Boston) in 2012 without knowing a single person. A year later I moved to Los Angeles and had to start all over again.
In this minisode, I'll share the exact process I used to turn visualization into manifestation — and, in the process, transformed everything I knew about success.
Onward,
James
PS - Join me and an incredible speaker lineup for a free LIVE event with Success Magazine.
_
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: How to Scale Success with Graham Weaver: Ep 200

Sep 17, 2024 • 1h 3min
204. Leaders Who Listen with Stephen Shedletzky (leadership expert) 🗝️
“Leaders who don't listen will eventually be surrounded by people who have nothing to say.” — Andy Stanley
How well do you listen? 🧐
For every problem you’re faced with — whether in your career, at home, or in your relationships — the answer is always one conversation away.
You have to be willing to speak, but even more willing to listen...
Stephen “Shed” Shedletzky is one of the world’s foremost authorities on leadership, organizational culture, and psychological safety in the workplace.
For 10+ years, Shed has contributed at Simon Sinek, Inc., where, as Chief of Staff and Head of Brand Experience, Training & Development, he headed a global team of speakers and facilitators.
He is author of new book Speak-Up Culture: When Leaders Truly Listen, People Step Up.
Shed supports humble leaders — those who know they are both a part of the problems they experience and the solutions they can create — as they put their people and purpose first.
Shed lives in Toronto with his wife and two young children.
In this episode:
• How to upgrade your career.
• What it means to be a good leader.
• The biggest mistakes companies make with their culture.
• How to find your “why” – and live it.
Let’s WIN THE DAY with Stephen Shedletzky!
_
🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/204-win-the-day-podcast-stephen-shedletzky
_
Episode links:
🎯 Download your FREE Win the Day action plan
📚 ‘Speak-Up Culture’ by Stephen Shedletzky
⚡ Stephen Shedletzky website
📝 Stephen Shedletzky LinkedIn
📷 Stephen Shedletzky 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 Stephen Shedletzky
1:40 Growing up with a grandfather who was a holocaust survivor (and being connected to sacrifice)
6:00 Teach people how to speak up
7:15 How a university professor became his #1 mentor
9:01 Being hired while people are being fired
10:21 The problem with most “leaders”
12:46 Who you should promote into leadership roles
15:38 How to teach good values to your children
18:29 The problem with charisma
19:10 Stop looking for your “dream job”
20:10 The #1 attribute of all good leaders (and parents)
24:46 Download your FREE Win the Day Action Plan
25:37 Right people vs right culture (Jim Collins)
27:40 Three things for any culture to thrive
31:33 Is Elon Musk a good leader?
34:27 How to give feedback that motivates people
38:49 What behavior are you rewarding
40:43 Use these questions to make change
42:25 The purpose of values – and how to live by them
45:10 How to develop empathy
47:21 Should you stay in a job you hate
50:15 How to find your purpose
51:55 Lessons from Rich Diviney (Navy SEAL Commander)
53:32 Leadership lessons for the home
58:22 Affirmation
59:38 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: How to Scale Success with Graham Weaver: Ep 200

Sep 11, 2024 • 23min
203. Win the Day Q&A (Crush Negativity, Stand Out In Your Career, Use AI Effectively, Move On from a Job) 🎁
“Sometimes you already know the answer. You are just not ready to accept it yet.” — Irini Zoica
Welcome to the Win the Day Q&A!
In this minisode, we're going to answer some questions that you've submitted:
How do you handle negative comments on social media?
How do you know when it’s time to move on from a job?
Should I use AI to write emails?
What's the best way to implement a new strategy for my workplace?
If you'd like to submit a question, send an email or audio message to info@jameswhitt.com
Onward,
James
_
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.
_
Show links:
🙌 Enrol in the Win the Day Accelerator: http://success.com/win-the-day
🎤 Full commencement speech at Hult graduation: https://youtu.be/5WN6-FLOVr0
_
Your support is greatly appreciated 🙏
#WinTheDay
In case you missed it: How to Scale Success with Graham Weaver: Ep 200

Sep 3, 2024 • 1h 14min
202. Lead by Example with Marlon Marrache (law enforcement expert) 🚨
“Make it your business to draw out the best in others by being an exemplar yourself.” – Epictetus
Marlon Marrache is a distinguished law enforcement professional with 25 years in the Los Angeles Police Department (LAPD).
Holding a Juris Doctorate, and regarded as a leading authority in discipline and misconduct – particularly in use-of-force investigations and officer-involved shootings – Marlon spent over 13 years with Internal Affairs.
He is an expert witness for high-profile cases, a consultant to law enforcement departments, and keynote speaker on all police-related matters.
In 2023, Marlon launched 'Internal Affairs: A Police Podcast' to give people a behind the scenes look into some of the most well-known law enforcement cases.
With recent calls to defund the police, crime skyrocketing in many communities around the world, and a bigger spotlight than ever on law enforcement, Marlon is here to help.
In this episode:
• How to perform in a high-stress career.
• How leading by example inspires those around you.
• Why we need to protect the ones who are protecting us.
• How to create positive pathways for the people who need it most.
Let’s WIN THE DAY with Marlon Marrache!
_
🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/202-win-the-day-podcast-marlon-marrache
_
Episode links:
🎯 Download your FREE Win the Day action plan
👮 Internal Affairs "A Police Podcast"
📷 Marlon Marrache Instagram
📷 Internal Affairs: A Police Podcast Instagram
⚡ Marlon Marrache (Blu Consulting Inc.) website
☕ Code 7 Coffee
🎬 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:
0:00 Who is Marlon Marrache
1:41 Interview starts
3:08 Why teenagers should play sports
4:03 Why you should lead by example
6:35 How mobile phones are changing the role of law enforcement
7:56 Holding police accountable
9:43 What cameras police use (including body-worn video cameras)
12:19 What police officers carry and what is an effective use of force
15:20 how effective is the taser for police officers
17:20 When lethal force is used
19:30 How personal stress affects police officers
20:58 The toughest day Marlon Marrache had on duty
25:55 Mental health challenges of first responders (the video James talks about: https://tiktok.com/@policecontent0/video/7187578703134739754)
28:04 Download your FREE Win the Day action plan
28:55 How accurate is gang crime in movies
30:25 How gangs recruit young people
33:35 Can police improve poor and violent communities
35:40 How police keep themselves safe
37:16 How to stay positive in a negative environment
40:04 The problem with lowering standards for new recruits
44:23 What does Internal Affairs do
49:24 What percentage of police officers are corrupt
56:05 Are police being held back from doing their jobs
58:54 How can people keep their home and community safe
1:00:18 How to deal with police burnout
1:05:11 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: Prepare to Win with Andrew Sullivan (Navy SEAL): Ep 154

Aug 28, 2024 • 21min
201. Rewrite Your Past 🔮
"These mountains that you are carrying, you were only supposed to climb." — Najwa Zebian
How are limiting beliefs from your past affecting your abilities in the present? 🤔
In 2012, I moved to the other side of the world to study an MBA...
Injury, relationship breakdown, and terrorist attacks all struck in what would be the most eventful year of my life.
Last week was my first trip back to Boston since then. I delivered the commencement speech at the 5,000-seat MGM Concert Hall for Hult's graduating students.
In this minisode, we'll go through how I wrote the speech, its biggest takeaways, and how you can rewrite the most traumatic moments from your past.
Onward,
James
PS - Click here for the full speech.
_
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.
_
Show links:
🙌 Enrol in the Win the Day Accelerator: http://success.com/win-the-day
🎤 Full commencement speech at Hult graduation: https://youtu.be/5WN6-FLOVr0
_
Your support is greatly appreciated 🙏
#WinTheDay
In case you missed it: How to Scale Success with Graham Weaver: Ep 200