Win the Day with James Whittaker and Brandon T. Adams

August 16, 2022
James Whittaker

Check out this episode on the Win the Day Podcast

Each day, if you do not make the decision to win, you’ve automatically made the decision to lose.”

James Whittaker

Hey Winners,

Today is a special day…

After three and a half years, we made it to Episode 100 of the Win the Day podcast!

Hosting this show has changed my life, hopefully your life too, and I’m so grateful that you’ve been on this ride with me.

Truth be told, I'm not very good at stopping to smell the roses…

What I'd rather do is focus on thanking YOU – from my very grateful heart – for supporting the show and making this milestone possible.

The obligation to provide value to you is something I take very seriously…

That's why at the start of each episode, I mention that the right inspiration can change someone's day, week, and life — because those moments (and the right belief or action at the right time) can make all the difference.

In fact, what we've done with Episode 100 is share all the secrets of what has made the show successful so you can replicate that in your own way and see what insights have made the biggest difference in my life.

As of today, the Win the Day podcast has been listened to in 96 countries … and that means it's time to step up.

The mission now is to help 100 million people in 2023 to Win the Day.

To do that, the show needs more visibility — and that's where your help (for only a few seconds) can make all the difference…

If you can spare a moment to help:

  1. Give the show a 5-star rating on Apple Podcasts.
  2. Give the show a 5-star rating on Spotify.
  3. Subscribe to the Win the Day YouTube channel.
  4. Share an episode with a friend.

That simple gesture can save someone's life and help bring some much needed positivity to the world.

And if there's something you'd like me to cover on the show (e.g. a question you have), send me an email to info@jameswhitt.com and we'll answer it for you.

I asked the Win the Day group how we wanted to celebrate Episode 100, and the overwhelming response was to have me in the hot seat! To lead the conversation, I’ve asked my good friend Brandon T. Adams to join me in the studio so we can have some fun.

In this episode:

  • Best tips from the most iconic people I've interviewed
  • How to connect with influential people
  • How to handle bad days when they happen
  • How to be successful with your podcast
  • What stops people from achieving the success they want; and
  • We’ll answer ALL the questions the Win the Day community has submitted.

Let’s WIN THE DAY for Episode 100!

Brandon T. Adams:
I am super excited! What I love about you James is the fact that you care so much about people and you always go above and beyond. What you've done for me over the years is extraordinary.

All the success James continues to have is because he’s so focused on adding massive value to people. When you do that, good things come back to you – and, for James, deservedly so.

So James, how does it feel to be at episode 100!?

James Whittaker:
Triple figures – it feels great! And I'm really grateful to have you here today as well.

It wouldn’t be possible without the support of people in 96 countries who have supported the journey. I’m deeply grateful for everyone who's listened and supported the show, and I’m also immensely grateful to all those who have come on as guests. 

Many great opportunities and connections have been established organically from the podcast. And if we made it to 100, I think we can get to 200 just as easy!

When you were younger, what career path did you naturally just go towards?

Being a writer was a big thing for me. Writing is also something that has always just come very naturally to me.

When I left high school, I enrolled in a Bachelor of English and Writing at university. And I'll never forget my first class. The professor, a successful local author, said, "Put your hands up if you want to make money from writing." And everyone – 200-odd hands – went up. Then he said, "Let me be clear, you will not make any money from writing." 

I thought, “Wow, that's interesting.” And not the most motivating sentiment! Definitely not what I was expecting to hear from the professor. The next day I enrolled in a dual degree, which simply added a business focus to what I was already studying. My intention was that it would help me develop skills that would allow me to earn some money so I didn’t have to struggle so much like the broke authors from the first classroom!

Writing, fortunately, is something that I take great pride in. Hopefully people can see that in how the finished episodes of the Win the Day podcast appear on my website – I’ve always wanted it to appear like articles in a digital magazine, highly professional and engaging. 

That's how I’ve been able to leverage my writing background with some of the work I do today. I’ve also got three bestselling books available in, I think, 14 languages around the world. So writing has always been very, very close to my heart – and, frankly, it’s a handy and versatile skill to have.

It just took me a long time to figure out how I could use it most effectively in a business sense.

So many authors, even very successful authors like yourself, struggle with different parts of the writing process. What's been the struggle you've had to overcome?

I don't really get things like writer's block. I’ve gotten very good at balancing discipline and inspiration, which means I rarely, if ever, struggle to get words on the page. And when you're looking at writing anything, your number one goal is ‘words on the page.’ A messy draft is better than a blank screen.

For me, one of the biggest shifts was doing my most creative work in the morning – as the priority. I had to take a step back, look at when my 2-3 hyper-creative hours in the day were, audit how I was spending that time currently, and then reprioritize how I attacked those tasks on a given day. 

Most people wake up and they want to pick the low hanging fruit. They do things like email, but that’s simply someone else’s agenda rather than your own. Today, for the most part, I only do emails when I'm tired – which is usually between 3pm-5pm – when I can do things on autopilot. In my most creative hours [10am-12:30pm] I’ll very, very rarely schedule anything else in there because that’s my most creative and sacred time to do the creative work, not the busy work.

That’s been a huge shift for me.

I like that. 

What has been the single biggest decision that's made an impact in your career to date?

Probably the decision to get good at relationships. That has come through a big focus on communication, personal development, and having some type of specialized knowledge that I can use to help other people. It means the time is spent efficiently and the success journey is more linear.

Most people have the best of intentions and try to connect with as many people as they can, but if you don't have any type of value that you can provide them, or you don't have a platform to be able to access their genius, it's going to be much harder to do that.


Check out the YouTube or podcast version where James Whittaker does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


So in the early days, I focused on building my expertise. Today, I have expertise in a bunch of different areas. And having the podcast – which we’re here for Episode 100 – means that if I connect with someone who's really influential, which is only happening more frequently as my career progresses, then I can bring those people into the Win the Day podcast.

We can have an amazing conversation for one hour. We’ll likely get along really well, and that opens up a whole bunch of connections through them. I can give them video assets, which further reinforces my value and willingness to go above and beyond – and people want to be around other people who have those two attributes.

That’s when I can ask them for any similarly-minded people who could be a great fit for the show, but in many cases they’ll voluntarily make the introduction based on how well we’ve gotten along.

You're 100 episodes in and, as a podcaster myself, I know how hard that achievement is! What was your reasoning for starting the podcast? And what's kept you going to get to 100 episodes?

I don’t know the percentage but I’m sure it's like 0.01% that actually get to 100 episodes.

I have no doubt you’re right.

The Win the Day podcast started as the Win the Day newsletter. And then I realized that people just don't naturally gravitate towards long form written content like they used to. So I thought, if these people aren't going to read the newsletter, then I am going to read it to them! 

And that's what I did. I hit record on my phone and that was it. That was me reading the newsletter to them. Then I thought, wow, if I'm already writing it and I'm already reading it, I might as well put a video camera there and record it.

So it's basically the same amount of work, except I can have it in audio, video, and written content. That was the origins of the Win the Day podcast – it started as the Win the Day newsletter. 

After one episode I realized, oh my God, you've created a podcast and you didn't even realize it! So from episode two, that's where I started recording an intro and an outro and all of these different things and made it a lot more professional. 

A big thing that I've focused on over the years is what can I do to always level up the professionalism, the guests, the questions, the experience, the audience and community interaction, all of those different things have been an ongoing focus.

So it's crazy, man, just seeing your journey and the people you've interviewed. 

Let’s get tactical. How do you prepare for your podcast and create the best experience for the guests? I mean, people ask me all the time to come on their show, but you give the best experience for the guest.

Share a few secrets on how you prepare, how you make the guests feel really good on the show, and then how you follow-up to build and maintain that relationship.

Every interaction and every touchpoint that you have with someone is an opportunity to either build trust or lose it. That's the way that I think about it. 

If someone comes on my show, I need to respect them through my preparation, through knowing their body of work and what excites them most today. I'm always looking at what I can do to add value and show that person how much I respect them – the best way to do that is preparation.

So if someone's coming on the show, I will read at least their most recent book, and I will listen to at least two podcasts that they have been on. My aim is to make sure I'm not asking the same generic questions that everyone else asks them. Things like, “what inspired you to do this?” and “what inspired you to do that?”

Every interaction and every touchpoint that you have with someone is an opportunity to either build trust or lose it.

You could have a guest who wrote an amazing book 10 years ago, but they may not care about that anymore. If you’ve done your preparation, you’ll know if that work is no longer interesting or relevant for them. Another thing I do is review the social media content they’re putting out there to learn about their messaging, their mission, and what excites them most today.

So in addition to those things, getting an introduction through a mutual friend (rather than reaching out cold) instantly solidifies it, and providing amazing video assets afterwards, because so much of your work is video.

Everyone is after more good quality video that they can use. As a guest on someone’s show, that’s what I want too!

So through that process, at the end of every episode, all the guests inevitably say to me, “Wow, this is the best – if not one of the best – interviews I've ever done,” which opens the floodgate for me to say, cool, if there's anyone else you think could be a great guest on the show, let me know. 

That's how we're able to continue increasing the quality of the guests on the show.

Have you ever been over-prepared?

Yeah, I think in the earlier episodes, I was a little bit too rigid in how I prepared.

You naturally get better at your craft the more episodes you do, so I can prepare in a fraction of the time today and still get a great conversation – because I’ve done the reps.

If you’re pressed for time, going ‘off the cuff’ can be a great tactic. Focusing on being present, and backing your skills as an interviewer, will likely lead to a better result than trying to cram study someone's background. Being too over-prepared can be a weakness.

Another thing I do, as I'm driving to do an interview, I'll listen to that person being interviewed by someone else at normal playback speed. And to me it feels like we're already having a conversation before the interview even starts. When I get to the studio, I’m simply entering the conversation rather than trying to connect from scratch.

That’s so interesting because I was watching Larry King's documentary and he talked about how the thing that made him great was being so in that moment.

As you said, it's good to prepare, but not at the expense of being in the moment. 

It can go to great sporadic directions organically rather than you being so rigid and having already mapped out the entire story. The story you’ve mapped out is just based on your research, not on reality. 

There are a lot of things that you won’t be able to find in your research, which means you’ll need to entice and tease different tidbits out of your guest – like a boxing match or a dance. That all comes through asking really great questions, for example “Is there a particularly dark day that stands out for you?” or “On your best day, what's an affirmation that you would write on a flashcard to show yourself on your worst day?” or “What was the mindset around [your field of work] growing up?”

These are questions that I've realized get very good – and usually vulnerable – answers. And that's why they’re a regular presence in my interviews, even though I try to add in a lot of unique questions too.

And sometimes the best questions come from the question you ask that leads to a journey, then you ask questions to get into it deeper, right?

Exactly.

What does success look like to you with your Win the Day podcast? Is it downloads, money, guests, or something else?

Good question.

To touch on what you just said before, connecting with a lot of billion dollar founders and really influential successful people, they really love sitting down and having a great conversation. And if you can provide that to enough people, it doesn't matter what else happens – they will want to help you as much as possible, even if no one ever hears the interview, because they've really enjoyed that genuine sincere conversation.

A win for me is the messages and emails I receive, and they’re only getting more and more frequent. So, to me, the real metric of success is how many people are reaching out to say that they now are focused on winning the day and they have adopted the Win the Day mentality. And they're sharing the Win the Day spirit with their family and their business and their community. 

That's the only real metric that I care about because to me, it's real.

Things like download numbers, and of course, business growth and audience growth, these things are important metrics, but they pale significantly… they're a distant metric behind real impact from people whose lives have been changed through them implementing the lessons and channeling the inspiration that's provided on the show from the amazing guests we've had on here.

From 100 episodes, what are one or two different things that came to you as a result of podcasting that drove you down a path – whether starting a business or even something you've done in your personal life – that's affected in a better way?

I didn't realize the power of podcasting until I was speaking at your event in LA so many years ago. At that event, I saw people talking about the power of podcasting.

I'd never been on a single podcast show before, but leaving that event, I made the commitment to be featured on 100 podcasts in a single year. Even though I hadn’t been featured on a single show before it, I was able to get featured on more than 150 podcasts – simply as a result of having the right plan, having the right intention, and following that relentlessly through a focus of delivering value and relationships.

Leaving that event, I made the commitment to be featured on 100 podcasts in a single year. 

If you can do those things, the whole world opens up. So the biggest thing that I've learned is really the power of podcasting, but more conceptually than that, it's just the power of telling your story – and the idea that if you don't tell your story, no one else will.

Storytelling is powerful. I mean, that's why I love podcasting, because people share their story, where the listeners can relate and then do something with their life.

And you have to have it through video for the most part now, because you can extract the audio, you can create a transcript, and you can put that out there in as many different forms as possible.

Filming us right now, we have three video cameras. For people who don’t have access to a podcast studio, use your phone – it’s how I started, was using my own phone. It's very easy for people to be able to record video content. We could pick up our phones and start recording great video content now.

People are so worried about what other people are going to think. Instead, you need to change your mindset to think about all the people who won’t have a transformation in their life because you’re afraid to press a button on your phone. If you’re so focused on what people who won’t even watch your videos anyway are going to think, you need to shift your perspective.


Check out the YouTube or podcast version where James Whittaker does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


Produce content for people whose lives you want to help, rather than being so worried about what people in your rearview are going to think.

So true.

What you do very well with your guests is providing them great content, a professional blog, engaging video assets. Most podcasters don't do that – and that's why the guests don't share the episode. So if you can make your guest look like a superstar, they're going to share with their audience.

What's been the biggest success from creating valuable content for your guests, where they shared it and it helped you really drive a lot of traffic?

Inviting people as a collaborator on Instagram. While TikTok is by far the greatest organic social media growth tool right now, don't sleep on Instagram. That invite collaborator feature is legit. 

If you upload a video, I did one for Chris Voss – author of Never Split the Difference – and that video has now got more than 800,000 views across different platforms. On TikTok, it did really well, but the ‘invite collaborator’ feature on Instagram enabled Chris to be able to share that.

So if you go and look at a lot of the posts I've done, you can see which ones have the collaborator tag, and then you can go and look at their profiles, like Owen Roddy (coach of UFC star Conor McGregor). So you can go and see my posts on his Instagram page.

Of course, that was all through amazing content that he had provided on the show. Same with FBI negotiator Chris Voss. Same with Gabby Reece, Navy SEAL William Branum, all of these different people are now sharing the content that we created together because I went the extra mile by giving them amazing video assets that they could use afterwards.

So you have all these people – billion-dollar founders, #1 New York Times bestselling authors, Navy SEALS. How are you connecting with these people consistently? What is your secret to being able to connect with them and get them on your show?

It's very much a long game.

The first and most important one is to have a platform to access their genius. Now you could reach out and invite someone out for a coffee, but who has time for that? You don't have time for that. I don't have time for that. 

Yeah someone emailing you to say “Can I pick your brain for an hour?”

Horrible! But if you have a sincere mission and a platform to be able to access their genius, like a podcast, your relationship will progress much faster and much deeper.

People admire hustle and they admire heart. Through your podcast, you reveal exactly how much hustle and heart you have.

To break it right down, figure out the list of people who you want to have on your show. Once you’ve got that list of names, find a mutual connection. That mutual connection means a trusted third party can introduce you so you're not going in cold.
Next, be sincere and upfront about the mission and what it is that you do, and invite them into their movement. What are you going to do to further their mission rather than being so focused on yourself? If you can do those things – and give them an amazing experience – you’re on your way.

People admire hustle and they admire heart.

The best thing about video assets is that you also maintain an ongoing presence in their life. So I might have done an interview 18 months ago, 24 months ago, but I can still repurpose and publish content in a unique way from that, which means they're going to see it. They're going to respect it. They're going to re-share it or accept it as a collaborator. And that means I'm staying front of mind.

So when I can reach out to them and say, hey, I know that you are connected with this person or this person, the chances of getting a yes are 100 times more likely.

In addition to that, I also have built up a good network of really just great people who have influential guests or people with great stories who just reach out to me and say, look, here's a person that I really think you should have on the show. And if they're a great fit, we make it happen.

I have a list here of some of the top people you’ve interviewed, and I’d love to hear your favorite lesson or insight from each one – just whatever comes to mind. I'm really excited to hear what you say. 

Let’s do it.

So the first one is Barbara Corcoran from Shark Tank. That’s a good one to start because you and I have an epic photo with her from the red carpet for the premier of Think and Grow Rich: The Legacy, the film you and I produced. 

What was a lesson you took away from Barbara?

I love Barbara, and it’s amazing what she's been able to achieve.

The big one for her is that you don't need to know everything yourself. It's a bit like the Henry Ford story that on the condition that you have an idea of where it is that you want to go, and you're always focused on adding value to as many people as you can, that you can find someone – and surround yourself with people who have the answers – so you don't need to know everything yourself.

That was my favorite. Getting the right people in the place is huge. 

Next one, John Assaraf from The Secret.

The biggest one from him would be to help the people who want the help, not the people who need the help. 

Over the years, I've tried to help so many people. And what I realized along that way was that often when I would try to lift people up, sometimes they can end up pulling you down because they're not ready for the help.

I asked John Assaraf, what do you do in that situation? And he said, “I only help people who want the help, not the people who need the help.”

It's powerful.

Now there's a lot of people out there who need help, but not everyone wants the help. So once they're committed and they show through their actions that they are ready for the help, that's when I'll give them everything I've got.

Rob Dyrdek.

Amazing guy. I mean, a skateboarder turned media mogul with all of the different TV shows and  brands that he owns at the moment.

The biggest one for him was building an entire life – your calendar, your entire week – about actions and people that give you energy rather than take it away.

You can even color code all of the things that you've got in your calendar. So color code them all – red means it takes away energy, green means it gives you energy. If you've got a whole week, that's full of things that are red, then you've got to start moving those things around or not doing those things at all.

Next one is one of my favorites. He's a fellow Iowa boy, Chris Voss, the FBI negotiator. What did you learn from him?

The big one for him would be everyone gets hurt, but not everyone lives hurt. That's such a simple but impactful shift to make.

That's good.

Once you’ve been hurt, recognizing that it’s okay, we all get hurt – albeit some a lot more severely and frequently than others – but it's your choice to live hurt. Use that adversity as fuel to go and do something great.

Wow. I’m going back to this! For anyone listening to this podcast or watching it on YouTube, this is so good. 

Next one is Gabby Reece.

The biggest one for her would be the best way to show that you are grateful for something is to take care of it.

Now, a lot of people talk gratitude. It's gratitude this, gratitude that. But if you were really grateful about something, then you would prove your gratitude by taking care of it before you have the problem.

So if you're grateful for your body, look after your body. Like they say, an ounce of prevention is worth a pound of cure.

Love it. 

Next one, Canadian billionaire, Errol Abramson.

Errol has passed away, sadly. Barely a day goes by where I don't think about Errol. I was so grateful for all the conversations we were able to have.

Two actually big things come from Errol. He would always tell me, “The squeaky wheel gets the grease.” He would constantly reference that as the importance of going after what you really want, rather than waiting for things to fall in your lap. So if you want something bad enough, then you have to follow up and do the work. 

And another thing he shared with me was to think about what type of life you want to have and then create profit centers to be able to manifest that lifestyle. If you don't want a billion-dollar lifestyle, you don't need to create profit centers to do that, but figure out what lifestyle you want and create the profit centers to get there.

Next one, our mutual friend, Rob Angel who invented Pictionary.

From Rob it would be to say no more often to things that don't serve you.

I think we've all been guilty of saying yes to things like going out and drinking too much or partying too much, whatever it is. But making sure that we are aware of what it is that really serves us and is getting us to where we need to be, the direction that we want to go in that'll take us to that destination, and making sure that we're saying yes to things that get us there rather than pushing us in the opposite direction.

5x New York Times bestselling author Sharon Lechter [30 million copies sold].

One thing I love from Sharon is the best money is royalty money – where you can earn money while you're asleep. 

That's where things like book projects and scalable digital products are really great because you can earn money while you're sleeping. 

Kerwin Rae.

The biggest one from Kerwin would be the importance of being calm in the midst of absolute chaos. 

Kerwin has worked with a lot of special forces operators. And a big goal of mine for the last two years has been to get comfortable with special forces tactical training, because when you're in a war zone – which you can simulate through gunfire and those types of things – your body is at its most stress, your life is literally on the line, that's where you need to be calm in that complete chaos.

I haven’t been able to progress much on that goal due to covid and the challenges of having a young family, but I’ve got it on my list and will get there soon. 

But I want to get very good at being comfortable handling high-powered weapons and being in that environment. My hope is that it would teach me to be calm and respond, rather than be scared and react, which would be a very useful skill in the real world when your back is against the wall but you need to be calm and focused. 

As an Australian, quite candidly, guns terrify me. And getting more comfortable in the midst of complete chaos and that pursuit of calm is something that I want to have as a big focus. Otherwise the stress will compound. We get comfortable by repeatedly exposing ourselves to discomfort and, since I haven’t had much exposure to military scenarios, that is something I would love to simulate.

The next one, The Sleep Doctor Michael Breus.

The biggest one for him would be that not everyone needs to wake up at five in the morning.

There are way too many rah-rah lifestyle entrepreneurs who espouse – and insist – that everyone needs to get out of bed at 5:00 AM. I get out of bed at about 7:00 AM most days. And that's what suits me based on my chronotype.

So the people who say that everyone should get up first thing in the morning at 5:00 AM or earlier, they just don't know about sleep science. So that was huge.

The next one, Keith Ferrazzi.

There is no excuse for you to remain mediocre. 

I know that might seem harsh for people who are in tough situations. Keith has come from some very difficult situations, as have the hundreds of people who I have interviewed. As a result of those conversations, I’m certain that there is no excuse for you to remain mediocre. You just figure out what it is that you want and you chart your path – that's straight from Keith Ferrazzi.

Keith has been a big influence on my career, well before the podcast.

Amen. 

So the next one is a legend who recently passed us, Bob Proctor.

With Bob Proctor, it wasn't so much of a lesson – and of course I've learned so much from Bob through his books, videos, and interviews that you and I have been part of – but the biggest one for him was just the energy of our interview. It was like he just reached into your brain and had a hold of it. 

So I think for him, just the energy was extraordinary.

He's really in that moment. I remember interviewing on the red carpet, he just like, he stopped. I asked the question, he stopped, he paused and then he answered so flawlessly. It's crazy how that worked.

Janine Shepherd.

Janine said resilience is not a line that you cross, it's a decision that you make every single day.

One more. It's a tough one for you! What have you learned from Brandon T. Adams!?

That's an easy one actually!

And I did a post recently talking about how you're the most persistent person I know. 

The biggest one for you is something that you actually shared on this show where you said ideas are meaningless, action is everything. And it is, it's completely true. Action is the real measure of intelligence.

I think, if I remember correctly, I said, “Ideas are shit without action!”

That's exactly what you said. And it's so true.

There are so many great lessons you’ve shared already. I'm going to go back and listen to them again! Because if the people watching this episode, or listening to this episode, can just take two or three one-liners and implement that in your life, just think of that impact.

That's why I love these shows and sharing that inspiration for people, so they can take one thing away and implement.

What specific and practical things have you implemented after your interviews?

Probably the biggest one would be after interviewing John Lee Dumas from EO Fire, who's had more than 2,000 episodes of the Entrepreneur on Fire podcast and featured me on Episode 1998. He’s a good mutual friend of you and I, and he’s generated more than USD $20 million in revenue through having the first daily podcast show for entrepreneurs.

The biggest one for him was that energy shift of doing your life's work before your busy work. So doing your most creative work when you have the most energy and then doing those things that you can do on autopilot later in the day, that's the busy work.

Have you had many behind the scenes challenges or technical difficulties that you've had to handle?

There have been some as a result of using Zoom, or having dogs barking, or a guest with crappy audio.

If you're dealing with people who haven't podcasted before and they have a crappy mic or they're using the computer mic, which is totally fine, but it doesn't lend itself to the best quality interview in terms of the sound or the content, because the sound can detract from the quality of the interview.

And it's why we're here in the studio, and it's why almost exclusively now I'm doing these interviews here in the studio because it completely alleviates those technical challenges.

For somebody who wants to get into podcasting, do you think there's still opportunity or is it too crowded?

Now is absolutely the time. 

There's a tale of two shoe salesmen who went to a new region, and they noticed that no one there was wearing shoes. One salesman came back and said, “It's not a good market for us because no one wears shoes.”

And the other salesman said, “It's the perfect market for us because no one wears shoes!”

Everyone now is aware of podcasting. This is your opportunity. Tell your story or no one else will.

That's so good. I've never actually heard the shoe story before.

What are the biggest mistakes you see podcasters make?

Being under-prepared, and being too transactional with the way they approach the relationships on the show.

The reality is you get 10x the ROI on your show before anyone even hears the episode. And you do that through getting a connection through a mutual friend, to the right guest, preparing for that, delivering them an amazing experience, and then the video assets afterwards. If you do that, the yield that you will get back on your podcast almost immediately is incredible.

The reality is you get 10x the ROI on your show before anyone even hears the episode.

And to quantify what that could look like in five years, 10 years, look at the networks that you and I have been able to establish, not just with each other, but through the guests and through all the people that we've been able to interview over the years. 

What is that worth to us now? And what would that be worth in 20 years as we continue to stay connected with these people?

Absolutely huge.

So this will be a good question for you, and I'm curious. I'm huge on video and I multipurpose it, but where can audio differentiate itself from video and how that can be so powerful?

Audio is good, and it's easy to get up for audio because you don't need to worry about how you look and you’re not distracted by looking at yourself like you would on Zoom. So there's certainly a lot more effort required for video.

But the important thing to remember is that you cannot bring video in for an audio file. You can do stock footage, but it's not really worth it. So I prefer to record video and then you extract the audio from there.

Next, you extract the transcription from the audio so you can have long-form written content. And then you extract short-form content out of that.

When you do that, you can create a near infinite amount of content from a single one-hour video interview.

I love that. 

We're going to switch it up a little bit. If you were working with a frustrated entrepreneur who was desperate to get to that next level, what steps would you walk them through?

Good question.

It would be through the things that we've gone through today. It would be telling your story, like you think out of nowhere, all of these people are going to find you!? 

In business and life, I like to stack the deck as much as possible. Force opportunity, fate, and luck to come your way rather than waiting for it.

You can create a near infinite amount of content from a single one-hour video interview.

The way that I do that is putting myself out there, so as many people as possible know about me – not just in terms of viewers, listeners for a podcast show, or readers of a book – but relationships where people know my mission. They know who I help and how I can help them, and can get me to where I need to go.

So just getting access to as many people as possible through that and telling your story, I think is an absolute no brainer and unbelievably easy for everyone to do.

You always talk about winning the day, but do you ever lose the day? And if you do, how do you handle it?

One of my favorite quotes is, “Some days you’re the pigeon, some days you’re the statue.” 

So yes, I have days where I'm low on energy and different things happen. I used to find that immensely frustrating, and it still can be very frustrating when you have things to do. Anyone who's a parent knows how challenging it can be when you wake up with very little sleep or no sleep at all. 

Rather than running harder on the treadmill, I try and just take a moment to myself. I get outside, a bit of sunshine, maybe go to the beach, just have time to myself, get outdoors or go and do some exercise, and just be at peace.

A good friend of mine, Alethea Boon, who's a five-time CrossFit Games athlete, once said to me, “You don't need to set a world record every day. You just need to give the best energy that you've got on that day.” And I really like that.

So that's what I try to do.

That's really good.

Well, we're going to go to questions from the Win the Day community. Are you ready!?

Let's do it!

Mary from Canada asked, "If you were to start all over again from nothing, what would you do and why?"

If I were to start all over again from nothing, I would launch a podcast from my phone so I could do it quickly and without spending a cent. 
I would go to a cafe in an entrepreneurial-type area and just work there, get to know people, and have organic conversations. And I would be interested in other people. That's the best way to be interesting.

So good. 

Most people don’t do that. They’d rather talk about themselves for 20 minutes. 

You and I were at an event recently and someone did that, which immediately shifted the energy in the conversation – I know you felt it too. She might have had the best of intentions, and been well qualified, but it’s the wrong way to establish a relationship. And it can be extremely off-putting, especially if you’re in a room where most people are doing that. 

Instead, ask questions of other people. That's the best way to get them interested in you. So that's the focus that I would have. I would just try and build up my network by adding as much value as possible, whilst I documented the journey and put video content out there.

Brett in Brisbane asked, "What is the best piece of advice you've been offered during a podcast by a guest?"

I'm trying to think of something we haven't shared yet today. And all the ones I mentioned earlier have been enormously impactful on my life.

Episode 58 with Greg Connolly, who's the founder of the world’s largest organic meal delivery service, Trifecta Nutrition. He said that, "The best business model to build, a real scalable business can only come through a subscription model." And I love that.

So the clients like the predictability of knowing that their meals are going to rock up every single week and the business likes the predictability of cash flow, because they can invest in all the other types of things for the business.

Having a business with a subscription model is very, very smart. It's a small thing to say, but when you dive into that interview in terms of sheer business value, I think that might have been the best interview out of all of them.

Suzanne in Canada asked, “When you have experienced a failure in your life, what steps can you take to learn from the situation? And how can you change it to a learning situation instead of being a victim of the situation?”

Good question.

I’d start by developing the habit of always asking yourself, “What’s the gift in this?”

That's great.

It's such a simple reframe, and sometimes that can take a little bit of time.

There are a bunch of other quotes that I think are helpful, like “Instead of ‘why me’, start saying ‘try me.’”
But we can also reflect on the famous Napoleon Hill quote, “Every adversity, every failure, every heartbreak, carries with it the seed of an equal or greater benefit.” I go and look at the stories, all of the people included in Think and Grow Rich: The Legacy, like Janine Shepherd, Jim Stovall – people who have overcome unbelievable hardship – they focused on the gift. They also remembered that the most important opinion is how you feel about yourself.

If you hold on to hate, the only person who gets destroyed is you.

No matter what challenge you get hit with, reflect on the experience and find a lesson. What can you action and implement from that lesson? What did it teach you? How will it help you move forward? It can be tough, really tough, but that’s what’s necessary to be successful over the long-term.

I mean, at the end of the day, you've got to let these things go. If you hold on to hate, the only person who gets destroyed is you.

Andrew from the Gold Coast, asked, “How much of a role did Entourage play in you choosing the entrepreneur dream in the USA and who is your favorite character and why?”

I saw that question come through! Shout out Andrew Mackey.

Entourage, great show. My favorite character, probably Ari Gold. I think Ari Gold is hilarious. And I will admit it's pretty cool being based in LA where I've lived now for the last eight years, where that show is based. I find it inspiring to live here. 

Rose in Tasmania asked, “I'm in the process of starting an online radio station, any marketing tips?”

Building up your audience organically is a good way to do that. 

So I would not wait until you hit record, and then all of a sudden, you think there's going to be millions of people there. What are you going to do to stack the deck of success by creating awareness before the launch?

Raise awareness organically through the content that you're putting out now, building up to a countdown to the launch day, and thinking about what partners and relationships that you can activate. Once you have your ideal audience in droves, drive them at a specific day to that launch and then make your audience and your community part of the conversation.

That’s what I would do, albeit a simplified version – the one thing not captured there is the resourcefulness and resilience you need to make it a mega success.

Lauren in Brisbane asked, "What was a time in your life where you took your biggest risk? What did this moment teach you?"

The biggest risk for me was at the age of 28. 

I made the decision to leave the industry that I'd worked in pretty much my entire life and to leave the city that I had lived in for literally my entire life and moved to the other side of the world.

I went from Brisbane to Boston where I didn't know anyone. I just moved there with my girlfriend at the time and was in an MBA that was nine months in Boston, three months in Shanghai in China. Thinking back now, that was a substantial leap and definitely my biggest risk.

And I couldn't even fathom it at the time, how impactful that would be for me. The biggest lesson was that I didn't realize how much of a bubble that I had been in until I left that bubble.

Moving to Boston got me around entrepreneurs for the first time. In fact, I was pretty much exclusively surrounded by entrepreneurs. I was 28 and I saw people who were my age and younger who were raising money. They were pitching, they were doing all of these things to get partners and clients, and all of that.

It was the first time that I'd been exposed to that. And the moment I saw those people doing it, that is when I realized that I could do it too. Small shift, but a huge step.

I'm glad you came to the US!

I should say that having interviewed 300+ people now, and delving so much into the work on resourcefulness, resilience, and success more broadly, I think – given a long enough timeframe – I would be able to find the gift in anything I experienced.

Today, I can’t think about ‘risk’ without thinking about ‘victimhood,’ and I have no intention of being a victim to circumstances ever again. When there’s something I want, I’ll develop the right plan, get around the right people, and give it a red hot crack. If it fails, I’ll have a good lesson – or at least a funny story – to carry with me.

Love that.

Nathan in Sydney asked, "What's the best advice you can give to someone wanting to be their own boss and start their own business or businesses?"

The best leader was once the best follower.

So if you want to start your own business, find the best leaders that you know, if it's in the industry that you want to be in. Look at how they treat people, their daily routine, how they grow their business, what they do for self-care. Take pride in being a great follower.

Once you do that, and if you're in a position where you can be getting a lot of value from them and ideally a little bit of money, so you're not making a huge leap and working for nothing – because that financial hardship and pressure can be very real and very debilitating – that's your opportunity to think about the movement that you want to create.

The best leader was once the best follower.

What's the business that you want to create and what are the problems that you want to solve? Who has those problems? What are the solutions that you can introduce? How do you attract the right attention, and turn that attention into engagement, and turn that engagement into sales, to grow your business and give them the transformation along the way?

So the last question from the Win the Day community is from Haley in Townsville, who asked, "What are your positive learnings from recent years in COVID, things you've learned to do differently and for the better?"

Self-care would be the biggest one.

So for me, I have my morning journal time – that sets me up massively to win the day. I also try and get a good hit of sunshine every day, go on fast-paced walks (often carrying my toddler!), and attend at least one full-body fitness class per week. 

It's about as much as I can do at the moment. If you’ve been in the Win the Day community for a while, you’ll recall the challenges I’ve shared trying to manage two kids under three with two working parents – especially with our 7-month-old who still has a very disruptive sleep.

Parenting can be very, very tough. For me, it's a successful week when I can stay consistent with my journal – and I haven't missed a beat on that, as we just passed 370 consecutive days – and getting that fitness class done once a week. If I can do those things, and have some quality family time, the week is a huge win for me. 

What are you focused on as a parent to give your kids the best chance of success?

Henry's only seven months old, so he's a bit young for anything too specific.

With Sophie, who is three and a half, I'm focused on, of course, making sure that she always feels loved and happy, but anytime that she's upset or frustrated about something, I ask her, “What's the problem?” We won’t move on to anything else. We stop, and we calmly figure out what the specific problem is.

If she can't figure it out, I'll help her figure it out. But we look at defining the problem and, once we’ve done that, I ask her, “What do you think is a good solution?” Sometimes I need to guide her to that solution, but she’s picked it up pretty quickly. We speak calmly, openly, and respectfully.

The reason I’m focused on that is so, no matter what career she pursues or what relationships she has, she’ll always be good at identifying the problem, mapping out all the possible solutions, and picking the best one based on her values and where she wants to go. I want that to become second nature to her.

My hope is that it becomes an immensely valuable gift that will help her throughout her entire life.

On your best day, what's an affirmation that you would write down on a flashcard that could show yourself on your worst day?

That's a question I ask everyone on the show and it's a hard one to answer! It's a tough one. 

Probably that you are destined for unbelievably great things that will help change the lives of millions of people. Keep going.

I love that.

What's one thing you do to Win the Day?

It would be the morning routine, which is a few different phases.

The first part is the acknowledgement phase, where I acknowledge that the day is there to be won or lost, then I make the conscious decision to win.

Second is the sacrifice phase, which is the cold shower, to prove that I've turned up for the day. Third is the gratitude phase and what's unique about the last 24 hours, which I do in my morning journal. Finally, writing down what three things would make today a win.

And then as part of that, it'd just be getting some sunshine. The rays invigorate me.

As we wrap this up, I just want to acknowledge you for what you've done with this show. You are the epitome of showing people what podcasting should be about. You're providing so much value. You're bringing on great guests. You're putting so much time into your shows.

For all of you listening or watching, the best way to thank James is to give the show a 5-star rating (rate on Apple Podcasts / rate on Spotify) and hit that ‘subscribe’ button. It will only take a few seconds to do that and I know he’d really appreciate it.

So thank you, James, for all that you do. 

Thank you to our quest host Brandon! Also a big shout out to all of you for listening, watching, and supporting the show.

As always, take purposeful action and keep moving forward. 

That's it for episode 100 of the Win the Day podcast! Remember to get out there and Win the Day.

Until next time…

Onward and upward always,

James Whittaker


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That’s all for this episode! Get out there and win the day.

Until next time…

Onward and upward always,

James Whittaker

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