With Absolute Specificity #8 – James Whittaker

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WAS 8 | Think And Grow Rich


Our minds and thoughts play a crucial role in shaping our reality and achieving success. James Whittaker, the co-author of Think and Grow Rich: The Legacy, emphasizes the power of the mind and the importance of thoughts and beliefs in shaping one’s reality. He discusses various other principles and concepts to make your dreams possible. Think and Grow Rich: The Legacy explores the role of habits, imagination, and intuition in achieving success, and it emphasizes the significance of surrounding oneself with a supportive network of like-minded individuals. James inspires and guides everyone in applying the timeless principles of success to their lives, providing a contemporary perspective on the enduring wisdom of Napoleon Hill’s original work. Tune in to this episode and achieve the results you want.

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With Absolute Specificity #8 – James Whittaker

Thanks for joining us. Welcome to another episode. We’ve got a special guest. It’s James Whittaker, host of the very popular podcast Win the Day. For those of you that don’t know, James is a three-time bestselling author. He doesn’t need a ton of introduction to my audience, especially because we’re all business geeks in our space but James has been everywhere. He has been on Today Show with millions of followers. He touches millions of lives. His book is a great book centered around Napoleon Hill’s Think and Grow Rich called Think and Grow Rich: The Legacy. I encourage everybody to check it out. It’s a great read. James, thanks for joining us. How are you doing?

I’m great, Jason. Thanks so much for having me.

It’s my pleasure. I’d like to delve right into that because I’m so intrigued as we talked about Napoleon Hill’s Think and Grow Rich and its modern-day application. Take my readers through the thought process behind the book and what you hope to achieve with it.

The book was released in 1937, the bestselling self-help book of all time. It’s an amazing legacy that it continues to have. People like Rob Dyrdek, Barbara Corcoran and Bob Proctor, all these people have had their lives transformed by reading this one simple book. Yet there’s been a whole bunch of people, many more people who have read the book that have done nothing with it. I have a giant canvas print behind me that says “Action, the difference between having and wanting.” It’s so true.

Everyone wants the results but they don’t take the action that’s going to lead to them having the results. The people who get inspired by Think and Grow Rich take action on it to achieve the results they are after. They’re the ones who changed the world and they’re the people that I’m so grateful to have been able to interview for Think and Grow Rich: The Legacy.


WAS 8 | Think And Grow Rich


It’s interesting to me. The fundamental premise behind what you said is desire without action is just desire. I’m reminded of the expression that opportunity often comes dressed like hard work. A lot of people want to get these shortcuts as these younger generations especially because technology facilitates the expedition of some of these processes. You can go be a YouTuber. What do you say to that audience and try to help them leverage their skillset that is looking for all those instant fame and viral stuff about the importance of these fundamental principles?

You have to recognize that instant gratification is the big dream killer. Something that’s going to make you happy in the short-term is not what we’re after here. We don’t want those feelings of short-term gratification. If anything, we want to do the complete opposite. We want to delay these things and put in the hard work but it’s also smart work.

If you can focus on increasingly making yourself more valuable, that means that you have more value that you can add to people who are higher up the food chain. If you rang Elon Musk or happened to meet Elon Musk at an event and you came to him with a solution to a problem that you know he was having, there isn’t a person in the world who wouldn’t listen to you if you had a solution to a problem that they have.

The only way to do that is to become more valuable over time. Focus on giving without the expectation of receiving anything in return and then focus on what you can do to leverage the relationships that you have. Much of all of this comes back to what are you going to do to check in with them regularly and provide value but you need to have a foundation of value yourself.

Focus on giving without expecting anything in return, and then focus on what you can do to leverage those relationships.

In particular for young people, focus on developing your skills. You touched on it there when you said skillset. A lot of people are busy. They’re frustrated that they don’t have the result but they don’t have the skillset. Develop a skillset that enables you to provide value and that value creates a great relationship and you continue to flourish from there.

You see a lot of it going on with that exact thought in mind where companies are starting to see that and capitalize efforts internally in skillset development. It’s an antiquated paradigm to think, “If I make my people too skilled at what they do, they’re going to leave and start their business.” That’s what we want, isn’t it?

That’s the goal. Make yourself redundant. “I’m all about that. Please do all the work. I don’t want to do it. Have someone else do it.” That’s the dream and the whole idea.

If you can elevate people and then leverage their skillset on their upward mobility and upward track, have something to do with that. I tell my team all the time that the best-case scenario for me is that we’re working on your business in a couple of years because we’re a marketing firm and we’d love to do that. We let our people do that. That skill development thing is lost on a lot of the younger generation. They think that technology skill supersedes the other more core, principled and important skills in the business setting.


WAS 8 | Think And Grow Rich


There are opportunities to be able to align the mission and purpose that someone else has with your mission to bring those things in. There are so many different ways that you can do that. People can look at different bonuses things like equity. All of those different things are available. If someone is so set on leaving to go and start their business, it’s much better to have a partner someone else in the trenches with you whom you can talk about and refer business to rather than burning that bridge.

People like the best entrepreneurs of all time. People like you, Jeff Bezos, Elon Musk and Steve Jobs see the world as an adventure to be lived. Whereas most people see the world as a danger to be avoided. If you’re looking at all your employees as a danger in the future, then you’re not going to be able to embrace all the opportunities that come from the adventure that you can live with them now.



Switching gears, I saw on your website you’re doing a mastermind class down the Mastermind. That whole concept to me is phenomenal. We talk to a lot of people like Brandon Adams and Kevin Harrington. You and I both know that they’re involved in that as well. Give us your perspective on the Mastermind and why it’s so powerful.

Mastermind to me has changed my life because quite frankly, the easiest way to be successful at something is to find someone who has the success you have and do exactly what they tell you. People try to overcomplicate it. If you want to be a marathon runner in the Olympics, go and find someone who’s been a marathon runner in the Olympics. If you want a billion-dollar business, find a mentor or someone that you can pay to get into that network. I’m all for that. If that’s your way of getting access to those people, it’s a representation of your commitment to that relationship.

That’s where a foundation of a friendship can start. Someone who has launched billion-dollar businesses can become close friends and mentors for life through very minimal investment if you manage relationships the right way. It’s so interesting we talk about podcasting. I’ve helped so many business owners talk about relationships, podcasting and everything else. They’re all thinking, “How can I monetize my podcast in the short-term?” What I’m doing is focusing on what I can do to leverage the relationships I have to $10 million, $50 million opportunities 5 and 10 years down the track. There’s a very big difference.



Play the long game, focus on value and do whatever you can do to get in the right room because the right conversation in the right room with the right people at the right time can change everything. That’s why I’m so passionate about it. In September 2023, I’m running a mastermind. I’m flying in from Hawaii with a Navy SEAL, which is going to be great.

We got Michael Bruce, The Sleep Doctor, who built up an email list of more than two million people by doing some pretty simple things that he’s going to share. We’ve got people like Brandon Adams. I’m super excited to have those people to help facilitate at the same time as we’ve got some incredible people from all around the world to participate and share their brilliance too.

I would love to get your perspective on a unique dynamic. What do you say to people that the mastermind is all about finding like-minded people and emulating successful behaviors, ferreting out and developing new successful behavior? What do you say to a guy like myself for example or this company, my team that’s trying to disrupt an industry where what you’re doing is counterintuitive to the revenue model or what’s worked the status quo? You’re trying to be a disruptor in an industry. What do you say to people that find themselves on that path where it’s going to be a little harder to find people of a similar mindset in a particular niche or space?


WAS 8 | Think And Grow Rich


I’d focus on getting as clear as you can about the problem. If you can articulate the problem better than someone who has that problem does, they’ll automatically assume you have the best solution. You can go down the route of trying to ask as many questions as you can to get as smart as you can about that audience of people you want to serve, which is very important. Sometimes they won’t be able to tell you exactly what they need. That’s why Steve Jobs was so great. He was the one that told them what they needed.

You can play it either way. As long as you’ve got your own, not necessarily a board of advisors but your own committee around you to help you with that mission as you’re ready to help those other people, you get some perspectives from outside of the industry to do it. More broadly and conceptually, if anyone thinks they’re going to disrupt an industry that is an incumbent that’s been doing things and had successful people for a long time, I see that a lot with like content creators on social media. If you think you’re going to beat Gary Vaynerchuk by doing exactly what he is doing except doing it at 5% of the volume and get toast, you’re going to get run over by all these people you have a level of disruption to be able to break through.

Our Gary Vee is just not a winning strategy man.

We’re in a content world. I’m trying. That’s where being authentic to your unique voice is very important. You don’t want to be a crappy Gary Vee. It’s much better to be the best Jason or John you can be. You can take inspiration from some of the people who have blazed the trail before you.

In that process, because you’re going through the mastermind thought process and you’re talking to people and listening, all of us that are in this level of business, we’ve all done it. Nobody gets here up by themselves. If you do, it’s a whole much harder road. Some people, I’m sure do. It’s a unique angle on the thing. My team is going to ask me and they asked me to ask this.

How do you know when it’s time to cut bait with somebody that you felt like at one point was on the same mission or of the same mindset and then suddenly there’s a diversion that takes place or you see them doing things that you don’t think are maybe ethical or whatever the case may be? How do you know when it’s time to walk away from those relationships you’re trying to develop?

The rule for me is never to let a significant thought go unsaid. Just because you are feeling something about your business partner or someone else doesn’t mean that it’s the truth. You’re missing context there because it’s just your thoughts. You need to figure out what’s in their head. By not letting that significant thought similar in your head, you can say to them, “This might not be the truth but this is how I’m feeling out of respect for our relationship. I wanted to bring it up.” It seems like you’re slacking off or moving in a bit of a different direction.

“What I’m trying to do is over here. Let’s get on the same page. How do you feel about me?” I’d be approaching it. You could word it a little bit better than that but never let a significant thought be left unsaid. Make sure anytime that you’re willing to have that conversation, you are prepared and ready to embrace what is going to come back because it’s always a two-way street. The truth is always somewhere in the middle and everyone has their truth.



James, what’s on your radar? What do you get coming down the pipe?

Big things. I’m filming a course for Success Magazine. We’ve got that launching very soon, the Win the Day Accelerator that’s going global so that’s going to be the very first time to put together this foundation. This has been my life putting this whole thing together. I’m excited to launch that. Win the Day Podcast is doing well. We’ve got about 23 million views at the moment so that’s getting better. How long have you been doing your show, Jason?

We launched it earlier in 2023.

What I tell people is don’t launch a podcast unless you’re ready to commit to at least a 12 to 24-month window. You get these exponential gains over time. You get better at your craft. I love using a podcast to build an entire content machine on autopilot. It is by far the best way to upgrade your network. Build your audience and monetize anything that you want to do if you do it the right way. Most people don’t do it the right way. A podcast is a great way of being able to do that. It’s so easy.

It’s great to use a podcast to build an entire content machine on autopilot. It is by far the best way to upgrade your network.

I know you’re a busy man. I’m not going to take a ton of your time. We appreciate you joining us. For all of my audience out there, you got to check out the new book, Think and Grow Rich: The Legacy. It’s fantastic. Check out the podcast, Win the Day. Real quick before I go, tell me about the Facebook group that you have for our audience.

Being in isolation is one of the toughest things. If you want to go into an environment, I’m very big on having the right conversations. It’s something that I naturally do. I don’t talk so much about the weather, traffic or anything like that. I seem to always be involved in these important and more meaningful, deeper conversations. I love to do that. If you’re struggling with something, you’ve got a question for me or you want to be around some like-minded people, jump into Win the Day group on Facebook. I’m happy to help as much as I can.

James, thanks again for joining us. We’ll talk to you soon. We appreciate it.

I appreciate it, Jason. Thanks so much.


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About James Whittaker

WAS 8 | Think And Grow RichJames Whittaker was born in Australia and currently resides in Los Angeles, California. After a successful 10-year career in financial planning where he led an adviser team with $2 billion under management, James began his own entrepreneurial journey. Today, through his podcast, social content, and media appearances, he helps two million people each month to Win the Day®. With a truly eclectic background, James’ superpower is helping ambitious but frustrated people gain immediate clarity on what they want and give them a bulletproof plan to achieve it.

James has been featured extensively in television, print, and digital media around the world, including The Today Show, Entrepreneur, Money Magazine, and The Sydney Morning Herald. He has also appeared on 600+ podcast and radio shows, and spoken to audiences of 2,000+ people. In 2019, James launched his own show, Win the Day with James Whittaker, available on Spotify, YouTube, Apple Podcasts and more.

He is author of bestselling personal finance and motivation book The Beginner’s Guide to Wealth, named book of the month by Money Magazine. His second book Think and Grow Rich: The Legacy was released in 2018 and has been translated into 15+ languages. It also serves as the official companion to the multimillion-dollar film based on Napoleon Hill’s timeless classic. (James is a proud co-executive producer of the film.)

In 2020 James’ latest book Andrew Carnegie’s Mental Dynamite was released in conjunction with the Napoleon Hill Foundation. Obsessed with what separates ordinary people from extraordinary achievers, James has interviewed 500+ of the world’s top performers to unlock their secrets to success, including Barbara Corcoran, Dr. Daniel Amen, JJ Virgin, Rob Dyrdek, Tim Storey, Gabby Reece, Dr. Michael Breus, Bob Proctor, Dan Negreanu, Chris Voss, and John Assaraf.

In 2022, he was named in the ’40 Under Forty in Podcasting’ global list by Podcast Magazine. With a diverse entrepreneurial background, James has launched successful companies and products across dozens of industries including health, film, activewear, marketing, and publishing.

James’ tertiary qualifications include a Bachelor of Arts (majoring in English & Writing), a Bachelor of Business Management (majoring in Marketing & Real Estate), and an Advanced Diploma of Financial Services. He also completed an MBA at Hult International Business School in Boston, Massachusetts, and during this time he was the principal organizer, MC and mentor for numerous high-profile entrepreneurship events.

Aside from business interests, James enjoys writing, reading, traveling, surfing, and beach time with his wife and two young kids. He is most passionate about helping entrepreneurs and professionals Win the Day®.


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