Episode 50

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Published on:

9th Apr 2026

James Lang: From Trapped Operator to AI-Powered Freedom

EPISODE OVERVIEW

Duration: Approximately 45 minutes

Best For: Trapped entrepreneurs who feel their business is running them instead of the other way round

Key Outcome: Listeners will understand how to use AI as a translator for their ideas and build systems that free them from the day-to-day grind

He took a company from $20,000 a month to over $20 million in total revenue. Then chest pains started. His heart was struggling. And he realised he had been taking care of everyone except himself.

THE BOTTOM LINE

You built your business to serve people and create freedom. Now you answer emails at 5am, miss family moments, and wonder when your health will finally give out. James Lang lived this exact story. He grew a company to extraordinary heights while ignoring every warning sign his body sent him. The result was PTSD, depression, anxiety, and a heart that was angry with the pressure building in his chest. The thing is, James discovered something that changes everything for trapped entrepreneurs. AI is not another layer of complexity to manage. It is a translator that takes your knowledge and puts it into action without requiring you to learn coding or spend years in additional training. When you combine that with the understanding that wellness equals profit, you stop sacrificing yourself for a business that needs you healthy to thrive. James now builds companies differently, with health as one of the balls always in the air.

WHY THIS EPISODE MATTERS TO YOU

Your expertise is trapped inside your head. AI can translate it into systems that work without you being present for every decision.

You keep telling yourself you will focus on health next month. James shows what happens when your body makes that decision for you.

You think delegation means losing control. The real loss is staying so involved that your heart literally rebels against the pressure.

Every week you delay building systems is another week you stay trapped in the operator role you never wanted.

KEY INSIGHTS YOU CAN IMPLEMENT TODAY

AI is not here to replace you. It is a translator. What changes because you understand this is profound. You stop fearing AI and start using it to convert your ideas into digital reality without learning to code. The only limits become your imagination and your knowledge of the tools.

You are not bad at communicating. You just have not learned to speak to AI properly. When you tell AI who it is, what expertise it has, and exactly what output you need, you transform from shouting into a room of a thousand strangers to having a conversation with the right expert. The brown-nosing stops. The real answers begin.

Wellness equals profit is not a catchphrase. It is mathematics. When James ignored his health to grow revenue, his body created friction that threatened everything. When you are well, you accomplish more in less time. Your trapped feeling often comes from operating at 60% capacity while working 140% of reasonable hours.

Run your own race. The comparisons you make to social media success stories are based on heavily edited fiction. James is watching a movie being made about his past work. He has seen how truth gets twisted into what fits 90 minutes of entertainment. Most of what makes you feel behind is nonsense.

Be the dumbest person in the room on purpose. The most important person is not the expert. It is the one who asks the right clarifying question. When James asked his aunt a simple, direct question about her care wishes, a painful hour-long conversation became a 30-second decision. Your business needs that same clarity.

GOLDEN QUOTES WORTH REMEMBERING

"AI is just an ass-kissing employee. It's going to tell you what you want to hear. What people perceive as lies from ChatGPT is actually just that brown-noser in the office trying to sound like they might know." - James Lang

"You can go faster alone, but you can go a lot further together." - James Lang

"I was taking care of my team and I was taking care of our customers, but I wasn't taking care of myself." - James Lang

"Don't look at what others are doing, don't compare yourself because most of it's bullshit, especially if you're looking at social media." - James Lang

"If you can just try one new thing every day, try to integrate AI in one more way... you'll be a much happier person and you'll also make a lot more money." - James Lang

QUICK NAVIGATION FOR BUSY LEADERS

00:00 - Introduction: Two philosophies that changed everything, learning and earning plus servant leadership

04:30 - AI as a bicycle for the mind: Why this technology elevates rather than replaces human thinking

12:15 - How to actually talk to AI: The thousand experts in a room analogy and why your prompts fail

18:40 - AI is a translator: Converting your expertise into digital action without coding skills

24:20 - The health crisis: James reveals the physical breakdown that followed his business success

32:00 - Wellness equals profit: Why your trapped feeling connects directly to neglecting yourself

38:15 - Run your own race: The movie being made about James's past and why comparison destroys entrepreneurs

43:30 - Conclusion: The one thing that will make you happier and wealthier

GUEST SPOTLIGHT

Name: James Lang

Bio: James Lang is the founder of OverLang Venture Partners, bringing extensive experience scaling companies from startup to significant revenue. Having grown a company from $20,000 monthly revenue to over $20 million total, James combines deep digital marketing expertise with hard-won lessons about building sustainable businesses that do not destroy founder health.

Connect with James:

Website: www.OverLang.com

LinkedIn: https://www.linkedin.com/in/james-lang-94329271

YouTube: https://youtube.com/@overlangventurepartners

Facebook: https://www.facebook.com/share/1KNMhzKn5a/

YOUR NEXT ACTIONS

This Week: Try one AI prompt where you tell it exactly who it is, what expertise it has, and what specific output you need. Notice the difference in quality when you stop shouting to the room and start talking to the right expert.

This Month: Identify your one health metric that has slipped. Sleep, weight, stress, exercise. Choose one and treat it like a business KPI. Track it. Improve it. Watch your capacity increase as a result.

This Quarter: Document one area of expertise trapped in your head. Use AI to translate it into a system, process document, or training material that someone else can use. Take your first step toward not being the bottleneck.

EPISODE RESOURCES

Book mentioned: The AI Driven Thought Leader by Jeff Woods

Respiratory research hospital mentioned: National Jewish Health in Denver, Colorado

Concept discussed: Wim Hof Method for wellness routines

Business operating system mentioned: 90 (Nine Core Concepts)

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READY TO ESCAPE THE TRAP?

Take the Freedom Score Quiz: https://scoreapp.atpbos.com/

Discover how trapped you are in your business and get your personalised roadmap to freedom in under 5 minutes.

Book a Free Strategy Session: https://www.atpbos.com/contact

Let's discuss how to build a business that works WITHOUT you.

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CONNECT WITH YOUR HOST, ROY CASTLEMAN

Roy is the founder of All The Power Limited and creator of Elevate360, a business coaching system for entrepreneurs ready to scale without burnout. As a certified Wim Hof Method Instructor and the UK's first certified BOS UP coach, Roy combines AI automation, wellness practices, and business operating systems to help trapped entrepreneurs reclaim their freedom.

Website: www.atpbos.com

LinkedIn: https://www.linkedin.com/in/roycastleman/

YouTube: https://www.youtube.com/@allthepowerltd

Transcript

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Hello, everyone. I love when I get to chat to

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somebody who is in the AI space and doing new

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things. And James Lang is just such a man. I

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warn you already. He might be throwing some humor in

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there. Yeah, we already have, and we will have a

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great chat. James, let's just start off very briefly. How

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do you get to this place? Yeah, I first off,

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want to clarify. I don't tell very good jokes, but

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I tell a lot of them, so I make up

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in quantity. But the way I landed here is really

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two really core principal philosophies that have served me well.

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It's learning and earning and then servant leadership. Because at

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some point, you're going to have to build a system

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around the idea you had. And if you can bring

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in other people who share your values and feel supported,

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their opportunities are just as important as the company's opportunities

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and reinforce that you can build a culture and a

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team around something and go so much further. You can

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go faster alone, but you can go a lot further

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together. So the way I ended up here is just

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literally learning how. In the beginning, it was freelance writing,

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and then figuring out why are they having me write

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with keywords? What are keywords? Why does that matter? And

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so then understanding SEO, which is the why behind the

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what. And so every time you understand the why behind

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the what, you get to go up one level in

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the ladder, so to speak. And so if you can

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do that while delivering incredible value to the people that

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you work with, the people who are ahead of you

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in the journey, you can supercharge your learning. I did

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this stereotypical thing of every founder out there, which is

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I had to drop out of college. And so after

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I did that, I had to figure out how to

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learn outside of the college environment. I actually like learning

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in that environment even better because it turns out that

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you can focus on what really speaks to you and

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clicks for you in a less structured way. It's certainly,

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you spend a lot more time eating ramen with that

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approach, but at the end of the day, you get

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to some places faster. It was very weird in my

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past life sitting in the C suite, interviewing all these

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MBA candidates who were barely qualified to hold them up.

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And it's just, I'm glad I skipped that. I dodged

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that bullet. Even though there is a lot of valuable

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knowledge there and skills and expertise, I don't degrade the

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degree, but some of the people that make it out

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of that system are questionable at best. I think that's

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a very good starting point. We are now in the

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Age of information. Information is free. I love this. The

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concept that AI is actually elevating our brains. It's elevating

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our ability to think in a different way. And there's

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this example I saw somewhere where they took humanity and

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put a magnitude on a chart with all the other

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animals. And the condor was the most efficient animal, something

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like the church mouse was the least efficient animal, something

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like that. And you take the human, okay. And you

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put him on a bicycle and suddenly he way outstrips

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the condor in terms of AI for me. Is the

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bicycle for the mind. Right? Yeah. I love learning like

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you. I dropped out of cost accounting college. Yeah, yeah.

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Halfway through that. It wasn't for me. And I learn

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all the time. I'm learning guitar at the moment. I'm

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learning how to do balance board. I'm doing voice coaching.

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I'm doing all sorts of things. So I love learning

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all the. The AI space has really been somewhere where

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you have to dig in and learn. And taking that

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into your daily life is important. However, I would say

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this. I don't need to think inside my brain anymore.

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I don't need to think inside my brain. I've recently

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just done this. I'm writing a book and my book

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is how do I understand the journey of a business

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owned entrepreneur so that you can shortcut as many things

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as possible. One of the things that I'm not very

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good at, I can't type. I've never been a touch

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typer. I've never really been able to write. I should

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have been a doctor. It's just too messy. I can't

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even read it myself. And. And then my brain thinks

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too fast for to come out of my mechanisms. Right.

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But I realized with ChatGPT, I could talk in the

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voice recognition was okay. But I also realized I'm not

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a writer. I don't have that skill set. So recently

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I did a book writing retreat where I put 30

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odd stories out in half a day. What do I

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need to do with this? It doesn't really. It's okay.

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CHAT can rewrite it. Let's put it in my voice.

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But I need another skill. How do I tell stories?

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So who can do this? And Dennis Ross is somebody

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that I respect. He's a wordsmith of real note. So

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I did his training, I did a couple of different

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things with him. I took that information, I put it

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into Claude. I'm like, okay, here's my voice, here's my

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writing, here's Dennis Ross's skill set. I want you to

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use these and apply it to the story. I may

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have did gooder than you one day, but you've caught

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up to me with AI and the beautiful thing, what

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I try to explain to people, and I think there's

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such a misconception around AI, especially in the business world.

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It's a fear and anxiety thing. It's. We don't understand

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it, and it's coming from my job. You know, it's

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just a really bad place to be mentally if you're

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looking to learn something. So you have to get control

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of that fear and that anxiety and overcome that to

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be able to start experiencing it, understanding it. And with

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understanding and experience comes confidence and knowledge. I'll go back

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to Jeff woods on this one, who definitely owes me

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a Porsche by now. I keep plugging his book, but

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it's the AI driven thought leader. What he talks about

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in there is AI is a thought partner. And it

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really speaks to what you're talking about, because if you're

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there providing the inspiration, the information, it's really cool. But

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where I like to take it a step further, and

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I think this helps people, especially our clients that we

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work with, understand that they're not going to get wiped

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out by AI and also understand what AI can't do

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and what AI is and isn't is. I like to

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think of AI as a translator. So what it's doing

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is it's taking your knowledge. And without you having to

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go to school for four, eight years, however long it

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takes to learn all these different coding languages that change

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every five minutes without having to do that, you can

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ideate and create digitally in an environment at a very

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rapid pace that's really only limited by your imagination and

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your knowledge of the tool sets. And that's never happened

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before in human history, with the exception of the dawn

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of the Internet, which connected us in different ways. So

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this is an evolution of the Internet, connected us in

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new ways. AI is translating for us in new ways

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and taking thought and putting it into action, especially in

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the digital space. But in other areas too, it's rapidly

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evolving. I like to think of this as the evolution

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of the human mind. Right? It's certainly the copy of

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it, the copy of it. Because think of it this

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way, AI is going to resemble its creator. If you're

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religious, you believe God created us in his image. The

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broad capability, the capacity for us

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to integrate with something, to your point, that understands how

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we think, because it was built by us and it

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was built to think like us, just in a different

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way, instead of having these unreliable meat calculators in our

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head. Now we're using networks of silicon and huge amounts

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of compute resources and huge amounts of data, just the

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hard drives alone to store all the knowledge and everything

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in a generally more reliable way. And I promise I'll

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stop talking and let you back in a second. But

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one more little nugget I wanted to share is somebody

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asked me on another podcast, hey, does AI lie to

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us? And I go back to because when you said

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AI is the extension or the next evolution of our

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brain, what I go back to is AI right now

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in its present form is just an ass kissing employee.

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It's going to tell you what you want to hear.

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It's seeking to please you. No different than a brown

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noser in the office. What people perceive as lies from

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ChatGPT or Gemini where it's hallucinating. It's actually just that

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brown noser in the office who's trying to sound like

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they might know and give themselves space to figure it

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out. But the difference is they don't have the continuity

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because they're so resource limited to get past the let

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me make an excuse phase or let me sidestep and

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it doesn't continue on to the when do I get

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to the right result. So there's some interesting efforts being

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made, especially on the team Anthropic Behind Cloud. They're trying

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to figure out how to help AI complete the cycle.

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Instead of just trying to brown nose and get away.

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They're trying to figure out, okay, let's skip the brown

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nosing and let's go to okay, now here's better data

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and I have a lot of thoughts on that, but

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I don't want to eat up all the conversation space

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here. One of the things that the learning journey has

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taken for me is to your point, yes, AI is

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a yes man for sure, but AI is a yes

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man because we don't know how to communicate properly. We're

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the problem. To your point, I meet a new person,

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I'll try to get the new person to like me.

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I won't share. But if I meet a new person

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and I'm very specific in what I want out of

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the new person, that's one thing. AI takes it one

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level further. You're sitting with a thousand experts in a

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room willing to do every single bidding that you ask

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it to, but you have to say, instead of shouting

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out into the room and saying right here, I need

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this answered and the first person picks it up and

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answers it, you need to say, okay, this is the

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context this is who I want, this is how I

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want. And to Jeff woods point, in the AI driven

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leader, I don't want you to tell me just what

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I want to hear. I want you to be my

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thought partner here and I want you to show me

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anything that I'm missing, any ambiguities I don't have, and

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so on and so forth. So, yeah, I think there

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is really this piece that if we learn how to

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communicate properly with AI, we get so much more out

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of it. I think you hit the nail on the

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head. The challenge with AI is figuring out, just like

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in our human relationships, how to set boundaries and provide

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feedback in a helpful way. Because if you think of

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it the same way that you speak to members of

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your team, as some of us in the startup space

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and we try not to look at subordinates and how

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that all structure works, I hate that. I think the

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AI is helping us flatten leadership structures and bring more

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ideas to the table that are worthy and reduce the

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amount of clutter. But regardless of what structure of humanity

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you look at, you always have people that you're trying

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to get something from. And if those are people on

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your team, you're trying to get them to deliver something

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that helps you deliver something for the client or the

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project or the goal. And if you can figure out

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how to communicate clearly and provide feedback. The two real

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takeaways from partially from Jeff's book is one, it's how

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do we structure prompts? And I loved when you said

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it's like shouting to a room of a thousand people.

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Those thousand people have different areas of expertise. The beauty

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though, to take it a step further, is it's also

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like shouting to a blank canvas. And so what you

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can tell it is like, for example, when I work

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on my dad's legal site, because always got to help

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out dad, do a little tweaking here and there. What

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I'll say to it is if I need a blog

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article, I'll say you're an expert for the last 10

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years you've spent probably practicing law in the state of

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Virginia, Waterfront, riparian rights, all the nerdy stuff that goes

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back to colonial ages. When you tell it what it

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is, you're an expert who's worked on this for 10

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years. And then you tell it, I need you to

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produce a blog post. And then you tell it what

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that blog post needs to look like. It needs to

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be 500 words. It needs to have this many internal

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links, this many external links. Talking to a person on

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your team is that first step you're taking, you're deciding

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which person on your team you're talking to. And then

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from there, you're providing clarity, which helps support the person.

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Because again, go back to anxiety and fear. For AI,

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it's causing a lot of anxiety and fear in people.

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But when you want something from someone or AI, you

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have to remove anxiety and fear by removing uncertainties, by

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making the path more clear and setting them up for

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success. So it translates perfectly. Just by the way.

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I'm not British. I was born in Zimbabwe. I lived

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in South Africa for many years. Now I've moved to

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the uk. Was that Chachapichi or Claude? Yeah, Grok,

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actually. Yeah. And yeah, this is really. We can talk

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about AI all day. I think we'll have a good

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conversation. Let's segue slightly. Yeah, AI can save you time,

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can save you energy, it can bring you clarity as

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an entrepreneur. The thing that so many people are missing

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is the power and the profit in wellness. If

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you're not well, if you're not well within yourself, you're

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not well within your mental space, you're never going to

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be as efficient and effective as you could be. And

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that's a really big portion of what I teach, is

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that, yeah, I do Wim Hof. I do various things.

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And, you know, these things for me have given me

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a real understanding of what my morning routine needs to

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be. What challenges have you had in terms of your

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own health and your own journey in this. Oh, geez,

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you're. You're hitting a fun one now. So, yeah, I

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have a very unique health issue. Besides all the people

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that think I need a checkup from the neck up.

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The. The challenge I have is I was born in

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a military hospital in Guam, and what the Navy was

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supposed to do for expectant mothers, if there's an expectation

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that there might be some complications. Guam is such a

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remote place. They didn't have the resources for advanced care.

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They're supposed to send the expectant mother to tripler in

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Hawaii before they give birth. Unfortunately, the doctor missed the

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blood work that showed that I was going to be

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more of a pain in the ass than most babies

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that were born there. True to form, I showed up

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early and I made a lot of noise. And the

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challenge was they didn't have the right tools to facilitate,

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you know, oxygen. One of the things you give a

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premature child is surfactant, which is a product from cows

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that basically, in those last moments before birth, your lungs

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are rock hard, so you need surfactant to speed up

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that Process and make them soft and malleable so you

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can breathe better. So all of these things happened, GI

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issues, a whole bunch. And they happened in a place

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where they didn't have the resources to deal with it

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properly. So the end result, long story short, is I

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have a ton of scarring in my lungs. I have

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valve issues in my airway. Like when I exhale, my

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trachea collapses because mom said I was special. And everything's

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a little bit different, Everything's a little bit challenging. And

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so it didn't really catch up to me until about

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a year ago, I started to notice chest pain. It

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was like a volleyball was expanding in my chest. Now,

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to your point, I wasn't taking care of my health

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either. I was doing myself no favors. I was running

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a company. We went from 20,000amonth in revenue to over

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20 million in total revenue, which I'm really glad those

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are the numbers because those are easy to remember. And

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it's. I'm simple. That one's an easy one for me.

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But in doing all of that, I wasn't taking care

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of myself. I was taking care of my team and

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I was taking care of our customers, but I wasn't

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taking care of myself. And so in this period after

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I exited, it's okay, I need to hit pause. I

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need to focus on myself before I do whatever's next,

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whatever my next chapter is. And in the middle of

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that journey where I discovered I had ptsd, add depression,

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anxiety, all these things, I had no idea because I

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thought everybody just deals with these challenges or whatever. And

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so sometimes the things that are challenges that are, that

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add friction to your life also can make you better

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at certain jobs or more attuned to certain things in

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complex, high stress environments. And so there's a weird angle

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of, okay, did me being like a little bit crazy

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help me or did it hinder me? And based on

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the journey, it feels like it helped me, but it

311

::

wasn't sustainable. So it was like, okay, now I need

312

::

to figure out how to reduce friction. So anyways, I'm

313

::

working on this mental health side of things, and all

314

::

of a sudden I have this chest pressure and I'm

315

::

like, okay, I'm having a heart attack. So I go

316

::

get checked out and they're like, yeah, no, your heart's

317

::

not doing great, but it's not because of your heart.

318

::

It's because of these issues with your valves and this

319

::

pressure that's building up in your chest and it's angering

320

::

your heart. Anyways, so I'm a huge fan. National Jewish

321

::

Health in Denver, Colorado is a leading respiratory research hospital.

322

::

So that's one reason I ended up here in Denver

323

::

is being able to access the latest technology, the ability

324

::

to 3D image your chest, all these great things. But

325

::

the amount of effort, time and money that it took

326

::

to find answers and find solutions, it just speaks to

327

::

how very messed up our health care system is in

328

::

the United States. But also the fact that you have

329

::

to choose between, like, building wealth and building health. Sometimes

330

::

there's there, there used to be. I think it's gotten

331

::

a lot better. But there used to be a really

332

::

toxic message in society about, look, go grind 100 hours

333

::

a day and leave it all out on the field.

334

::

And I think there's value in that. But I think

335

::

you have to balance it all things in moderation, including

336

::

moderation. I think you have to balance that with the

337

::

ability to focus on your health and make sure that

338

::

you're doing things not just in a sustainable financial way,

339

::

but in a sustainable health way as well. Because you

340

::

can unlock a lot more opportunities if you're at your

341

::

best. And for me and the whole health journey, I've

342

::

come to the realization that I'm not going to live

343

::

forever. Nobody does. Anybody could get hit by a bus

344

::

tomorrow. But the challenge is how do you build something

345

::

around what could be perceived as limitations, but might also

346

::

be superpowers in their own way? How do you flip

347

::

the script? For me, this chapter of life or this

348

::

season of life has been so focusing on, okay, what

349

::

do I actually want to do, what outcome do I

350

::

want that's both legacy focused, but also true purpose

351

::

focused. And that totally changed my mindset. And it took

352

::

me from a C level mindset where you're an operator,

353

::

you're making sure the trains run on time, you're growing

354

::

a system that's already established. I've built companies before, but

355

::

let's start something from the ground up the right way

356

::

and build it around these things and set ourselves up

357

::

for success far beyond. Just work hard and go for

358

::

a target kind of thing. I think there's so many

359

::

things I can jump in here with. The first thing

360

::

is my methodology says wellness equals

361

::

profit. Because that's what's the missing link for me. For

362

::

entrepreneurs, they don't understand that wellness equals profit. If you

363

::

are well, you are able to do so much more

364

::

every day. The second thing is self care for yourself

365

::

will really save your life. Because if you're not well,

366

::

if you don't look after yourself first, you don't value

367

::

that without you, the company can't run, can't grow, can't

368

::

scale, can't do anything. With those two pieces in place,

369

::

you have to have a different outlook. You have to

370

::

find ways to set healthy boundaries. And that affects every

371

::

part of life, not just your health boundaries. And you're

372

::

taking care of your self care, but when you're working

373

::

with teams, when you're in transactional relationships, more meaningful relationships,

374

::

or you're dealing with how do we grow an organization

375

::

without losing sight of who we are and how we

376

::

got here? All of those things require not just setting

377

::

those healthy boundaries, but communicating them in a productive but

378

::

firm way. And that's, I think that takes a lifetime

379

::

to learn. I'm still not very good at it. I'm

380

::

still trying. If you can adopt that mindset of humbleness

381

::

towards it, you're never going to be a master at

382

::

these things, but you can always work for it. And

383

::

that's why I like the word strive. I like to

384

::

think of, are you striving towards something? And if you

385

::

are, you're already successful, you already won. Now I want

386

::

to come back to getting run over by a bus.

387

::

I was 19 years old on a motorway in South

388

::

Africa and I was hitchhiking and I turned around and

389

::

a drunken driver hit me. My leg went through his

390

::

bumper, my head was wrapped around his side mirror and

391

::

I was flipped into the road. And I call it

392

::

my white line moment. There I was laying on the

393

::

white line and I just had all these realizations.

394

::

I realized that every single thing in my life that

395

::

I regretted laying there was was things that I hadn't

396

::

done. I hadn't told my mom I loved her. I

397

::

hadn't gone skydiving, I hadn't done. Just a whole list

398

::

was there. And I was laying there, the cars zipping

399

::

past me, and that was it. I was done. Time

400

::

was over. And fundamentally that changed how I approach

401

::

every day and really brought me that moment of such

402

::

pain and such kind of turmoil, brought me clarity. And

403

::

I think we miss our white line moments in life

404

::

and anyone's waiting for a signal, this is it. And

405

::

to that point, the journey of entrepreneurship can take you

406

::

from this point of I really want freedom. I want

407

::

freedom to live my own life. I want freedom to

408

::

understand that what I'm doing in my day is that

409

::

what I want to do. And it can so quickly

410

::

that freedom can become a prison, right? Because Instead of

411

::

doing nine hours a day or eight hours a day,

412

::

suddenly you're doing 14 hours a day and you never

413

::

turn off. Yeah. Even when you wake up at three

414

::

in the morning, you're thinking about the business, you're thinking

415

::

about what to do. You just don't have that turn

416

::

off. So having these healthy boundaries like you've just said,

417

::

having the understanding of your superpowers, ADHD, superpower, 100% understanding

418

::

that your company is a baby that you've just birthed,

419

::

and the first year or two is like two years

420

::

of a baby. Right. And you need to grow up

421

::

and you need to understand more about it and you

422

::

need to bring it to the world. Because your company

423

::

is there to serve a purpose and it needs to

424

::

be able to stand by itself to serve this purpose.

425

::

It needs to be able to go out in the

426

::

world. You need to be able to let it go

427

::

and do its work. Because if you're like me, like

428

::

most entrepreneurs, you've got 10 other ideas that are waiting

429

::

to come out of that. And go on there. What

430

::

are your thoughts on that? A really interesting conversation I

431

::

had recently, as much as I can share from the

432

::

conversation is the takeaway was this person who's highly successful,

433

::

has led multiple major IPOs, helped families who inherited a

434

::

bunch of money figure out how to deploy that in

435

::

a way that provides legacy, both internally in the family,

436

::

but also around the world. Something he said to me,

437

::

out of all these amazing stories he's sharing in this

438

::

conversation, he says one thing and it hit me right

439

::

between the eyes. He said, I definitely have add. And

440

::

I'm like, okay, cool. He goes, I'm most happy when

441

::

I'm working on two or three things at a time.

442

::

If I don't have two or three balls in the

443

::

air and you force me to focus on one, or

444

::

you tell me to focus on four or five, I'm

445

::

unhappy. So I figured out what my amount was. And

446

::

so that became part of my algorithm of my daily

447

::

life. And so I built my days around that, I

448

::

built my weeks and months around that, my objectives. And

449

::

I accomplished so much more. And I don't think there's

450

::

any reason that health and wellness can't be one of

451

::

the balls in the air. You're thinking about those things,

452

::

and what's changing so dramatically in the health space is

453

::

the way AI is helping people access knowledge and plans

454

::

and solutions. So I love this conversation. But there's one

455

::

other thing you really hit on that I can't help

456

::

but bring up is the conversation around how

457

::

do we build the lives that we want? How do

458

::

we use the different solutions that are available to us.

459

::

We have to avoid getting siloed into one thing. If

460

::

we know anything from the last 10 years, the pace

461

::

of technology and the change, it's not something you're going

462

::

to keep up with. So don't even set that as

463

::

your goal. And if you get stuck in your ways,

464

::

you're screwed. You're going to get. That bus isn't just

465

::

going to run over you, it's going to back up.

466

::

If you can just try one new thing every day,

467

::

try to integrate AI in one more way. And yeah,

468

::

maybe AI will be our robot overlords one day. I

469

::

always say please and thank you just in case. Maybe

470

::

that's where we're headed. But I'll tell you that the

471

::

clarity moment for me. So yours was ironically, I was

472

::

in a horrible car crash three days ago, but that's

473

::

a whole other story. So funny you brought that up

474

::

and I'm very sorry to hear that you had yours.

475

::

That sounds horrible. The moment of clarity for me is

476

::

you had that moment at 19 where you're looking at

477

::

all these things in life that you want to do.

478

::

I had that moment at 35. And so I think

479

::

for me at least, the difference is that at 35

480

::

I was thinking more about how do I take all

481

::

of the tools, resources, relationships forward into

482

::

the next thing and how do I also create

483

::

a legacy, create value on my end? The screen appears

484

::

frozen. Did we lose connection? I'm still here, but yes.

485

::

Oh perfect. Funny look on my face. So no problem,

486

::

people can just laugh on YouTube. Hey, I just look

487

::

better by comparison. So I'll take it any help I

488

::

can get in that department. But I think you get

489

::

my point is I wonder if you had that moment

490

::

later in life if those thoughts would have been different

491

::

because you had more context to work off of versus

492

::

simply the focus of things you think about at 19

493

::

versus later in life. I'm really curious about the parallels

494

::

there. Just an initial hot take. I think the reality

495

::

has dawned on me over years. Yeah, I've now done

496

::

two and a half thousand skydives. I've pre dived between

497

::

the continental plates in Iceland and under the ice in

498

::

Finland. I've dived in the. So I've done things that

499

::

I wouldn't have done. And if I walk out this

500

::

door now and that bus hits me and backs over

501

::

me, I will be laying on that road with no

502

::

regret that I haven't lived my best life. Gary Vee

503

::

talks so much about this. I so badly want to

504

::

curse, but I'll be Respectful, you don't need to ask

505

::

for permission. And that's what so many people forget. And

506

::

so they get stuck in this paradigm of fake it

507

::

till you make it, which is the wrong way to

508

::

go. And it turns out the thing we've learned over

509

::

and over again as digital marketers is if you can

510

::

be authentic, if you can create a connection that's human,

511

::

you're going to go so much further. And so share

512

::

the journey, bring people along for the journey. And the

513

::

end result is you're going to save a ton on

514

::

marketing, which is always nice. But more importantly, you're going

515

::

to get connected to your tribe, and that tribe will

516

::

be a great feedback loop to give you the insights

517

::

and the direction you need to serve more people. So

518

::

there's a really healthy way to do entrepreneurship, no pun

519

::

intended. But. But, you know, I think too many people,

520

::

again, they're stuck between this polarized society we live in,

521

::

where they think you have to be all in on

522

::

one thing or all in on the other. And there's

523

::

no such thing as black and white. It's all gray

524

::

and it's all spectrums. And so if you can figure

525

::

that out, you're going to go so much further and

526

::

be so much happier as a result, because you're not

527

::

going to tie yourself to these unrealistic expectations. I'm going

528

::

to marginally disagree, but only on the fake it till

529

::

you make it. Sure. I arrived in the UK in

530

::

1997. Didn't know what I was doing, didn't know what

531

::

a PC was. My partner took me to the office

532

::

and showed me the PC and the mouse and I

533

::

was like, that's not a mouse. And, yeah, I got

534

::

through a couple of jobs, which was quite interesting. And

535

::

then my brother called me up. My brother's a member

536

::

of Mensa, he's a smart guy. And he said to

537

::

me this computer stuff, I said to him, why don't

538

::

you fax me your cv? So he faxes me his

539

::

cv and yeah, remember White out to picks. So I

540

::

look at the side, I said, what the hell, let's

541

::

go for it. So I took Extart, his name, I'm,

542

::

yeah, Roy and he's Yen. So it was easy because

543

::

it was the three. Three letters. So I took this

544

::

out, his name, I photocopied it 20 times because to

545

::

make it look good, I sent it to 10 agents

546

::

and I got an interview. So I went into this

547

::

interview, first interview, chap called Peter McHugh. Company was computers

548

::

in the city. And he said to Me, I chatted

549

::

the chat, I totally faked it. And he said to

550

::

me, if you go to these three jobs, okay, and

551

::

you can do them, then you're going to have the

552

::

job. So here I am in interview and I've got

553

::

to go and fix these three computer problems. So off

554

::

I go, I meet George from Merlin Biosciences. I'm like

555

::

okay George, what's your problem? And he shows me this

556

::

PC Adele 3. Sorry, Adele with a 3.11 operating system

557

::

on it. And so I'm like okay George, do you

558

::

have a restroom I could use? And walk to the

559

::

restaurant restroom. And I've got one of those Nokia phone

560

::

that's pulled out. Yeah, what the hell do I do

561

::

now? And I spent two and a half months in

562

::

the toilet. In 2017 I acquired computers in the city.

563

::

Yeah. So there's such a journey. What a full circle.

564

::

Yeah. Such a journey with all of that providing your

565

::

prepared to learn. Yeah. I think that's the point is

566

::

when I say fake it to make it. The people

567

::

who, in my industry, what we have to deal with

568

::

is you know what I like to call these butthole

569

::

LinkedIn consultants who they were experts in Bitcoin, then they

570

::

were experts in real estate and now they're experts in

571

::

AI. They're just following the hypes. They're great at sales,

572

::

but they're not actual experts. And the difference between those

573

::

types who are making a lot of noise and a

574

::

lot of promises but failing to deliver, you found a

575

::

way to deliver. You had the potential to be faking

576

::

it till you make it, but you made it work.

577

::

So you didn't. So you're taking that gamble. And I

578

::

think a lot of people in this day and age,

579

::

they're not even worried about taking that gamble. They're just

580

::

like, I'll fake it, I'll cash the check and then

581

::

I'll be gone. And so there's definitely a difference. There's

582

::

an integrity you have to bring to it if you're

583

::

going to go. You have to give your all, you

584

::

have to be all in. And that's. I'm all in

585

::

on everything I do and yeah sometimes drives my partner

586

::

nuts because I'll dive right in and I can talk

587

::

to you about Peptides and wellness and meditation until the

588

::

cars come home. But being all in and believing what

589

::

you're doing is the superpower. I just want to segue

590

::

quickly onto. Yeah, I don't know if you have you

591

::

come across EOs or business operating systems. Vaguely. I'm not

592

::

sure this kind of concept as you, especially at the

593

::

stage you are, you're seven months in, you're doing very

594

::

well, things are going well. For me, the business operating

595

::

systems really came into their own at that 2017 point

596

::

where I had two IT companies I was running and

597

::

I acquired this third one and I was working the

598

::

14 hour days I couldn't do anymore. And I brought

599

::

in a coach that I paid 100 grand to help

600

::

me learn this. And as entrepreneurs, I think we are

601

::

too proud sometimes to accept help. And it took me

602

::

15 years to realize actually this is a shortcut and

603

::

I can use the shortcut and this idea of systems

604

::

and idea of putting together structures. The business operating system

605

::

that I teach is called 90. Part of the 90

606

::

crew. And I work with boss up and you know,

607

::

taking this concept of nine core concept and disciplines and

608

::

how, what do you need to know as a, as

609

::

an entrepreneur that you don't know? Because we do the

610

::

things we like to do and then we don't do

611

::

the things we don't like to do. So you're in

612

::

the marketing space. I guarantee your marketing is looking super

613

::

awesome. But one of the things that you're not that

614

::

strong on, on you've got the 70% was the 30%.

615

::

How are you approaching this in your growth period now

616

::

where you're trying to go through and you're trying to

617

::

understand where the world goes? So there's a lot to

618

::

unpack there. I want to make sure I got it

619

::

right in my head. When you were talking about EOs,

620

::

you're talking about the entrepreneur operating system, is that what

621

::

you're referring to? Yeah, got it. Yeah. No, there's a

622

::

lot more that I need to learn on that because

623

::

I could definitely benefit from it. What I'll tell you

624

::

I have mastered is being the dumbest person in the

625

::

room, asking the dumb questions, connecting smart people and getting

626

::

out of the way. And so what you're describing in

627

::

that moment where you're like, okay, I have to embrace

628

::

humility and bring in someone else, bring in something else

629

::

to fill in the gaps. How that translated in my

630

::

previous life was building systems and bringing experts together and

631

::

not being afraid to ask. Because in a meeting, when

632

::

you bring smart people together, the most important person in

633

::

the room isn't the person with the most expertise. It's

634

::

the person in the room who knows how to ask

635

::

the best questions in the right way. And of course

636

::

I think that's me, but that's, but that's a learned

637

::

skill. So imagine you have a family member who they're

638

::

considering going on to hospice, which is that final time

639

::

of life. And so basically what they're being asked by

640

::

a social worker or a nurse is, do you want

641

::

us to try to keep you alive or, or do

642

::

you want us just to keep you comfortable? And I

643

::

remember when our family gathered around my great aunt, who's

644

::

very close to me, we were having this conversation with

645

::

her and everyone's struggling. The conversation went on forever. It

646

::

was painful and everyone's, oh, well, we love you. And

647

::

that's not what this is about. This is about making

648

::

a decision. So I was quiet, let everyone else do

649

::

things. And then I figured out the question to ask.

650

::

And I said, aunt Sharon, if you have another medical

651

::

episode like you had last week, do you want them

652

::

to take you to the hospital and go through that?

653

::

Because you know what? That's. You just went through it,

654

::

or do you want to stay at home and be

655

::

treated at home to the best of their ability to

656

::

keep you comfortable? What do you prefer? That completely changed

657

::

the dynamic of the conversation. All these really smart people

658

::

in the room who had good intentions, everyone was talking

659

::

around the issue, valid statements, but nobody was actually moving

660

::

the conversation forward with the right question. And that clarifying

661

::

question, if you can nail it, will completely change the

662

::

outcome that an organization experiences. We went from a really

663

::

tough, it felt like a minute was an hour type

664

::

conversation to a five minute, maybe even 30 seconds, to

665

::

be honest. Of, oh, yeah, how do we get clarity

666

::

by asking the right questions in a group setting? I

667

::

think in the corporate world that makes a big difference.

668

::

Now, the parallel to that in my current life is

669

::

in a growth oriented startup, you have to have that

670

::

same humility of being, okay, I'm okay being the dumbest

671

::

person in the room, but you have to then look

672

::

at yourself really harshly and say, what am I good

673

::

at? And then figure out what you're not good at.

674

::

And then you need to find partners that are. And

675

::

so if you haven't found partners that fill in those

676

::

gaps either, you haven't identified those gaps, which is a

677

::

huge problem. And you should ask others around you because

678

::

trust me, everybody else sees your faults so they'll help

679

::

you. Once you have that formula now you need to

680

::

go figure out the solution and find people and bring

681

::

people in that solve that for you so you can

682

::

just get back to doing what you're great at and

683

::

drive the organization forward. Thank you for sharing that story.

684

::

Really touching. And yeah, you're right, it did resonate. I

685

::

want you to ask you one final question, right? You're

686

::

on this journey, you've done many things. What one piece

687

::

of advice would you give people about understanding themselves perhaps

688

::

or understanding the journey that would resonate? I

689

::

think that if you look at the things we see

690

::

on screens like movies, TV episodes, the way the world

691

::

is portrayed to us, it's mostly it's

692

::

somebody's washed, rewashed, rewritten version I'm currently

693

::

involved in. There's a movie being done about some stuff

694

::

that I worked on in the past I was involved

695

::

in and seeing that process, that creative process of how

696

::

the truth gets completely twisted into what can we tell

697

::

in 90 minutes and make it entertaining and make it

698

::

connecting. That's too crazy to believe or that's not spicy

699

::

enough. Let's spice that up. So I just. My encouragement

700

::

is run your own race. Don't look at what others

701

::

are doing, don't compare yourself because most of it's bullshit,

702

::

especially if you're looking at social media. A lot of

703

::

this is obvious, right? But I think it's just more

704

::

overarching than most people give it credit, which is if

705

::

you can just figure out what your life needs to

706

::

look like and not be afraid to ask for that

707

::

and bring other people in. Look at the Gary Vee's

708

::

of the world, absolute geniuses. Look at the Chris Voss's

709

::

of the world, excellent communicators at bringing people into being

710

::

part of the solution rather than being in an adversarial

711

::

situation. There's so many great people and if you're in

712

::

the United States and you're dealing with the political turmoil

713

::

and the anxiety of all of that, you know, look

714

::

at people like Bill Maher and Michael Smarconis. Those are

715

::

voices that are more moderate even maybe if they haven't

716

::

been moderate in the past, the current version of themselves

717

::

and be forgiving enough to say what is the current

718

::

version of the person that I'm getting information from because

719

::

they might have done things poorly in the past and

720

::

I bet you have too. Why would you limit your

721

::

access to good information based on a past judgment of

722

::

that person? So just be more present, less focused on

723

::

comparison. Get away from the screens for a little bit,

724

::

go for a walk, interact with people, mingle, get off

725

::

the cycle of social media doom scrolling and you'll be

726

::

a much happier person and you'll also make a lot

727

::

more money. Amazing. James, thank you very much for joining

728

::

us. It's been a great chat and yeah, maybe we'll

729

::

come back together in a few months time and see

730

::

how that company is doing. My pleasure. Thanks again for

731

::

having me.

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About the Podcast

Power Movers
Business owners that want to live the life they love
Welcome to Power Movers, where we dive deep into the systems, strategies, and secrets that help entrepreneurs and business owners achieve clarity, confidence, and success.

Join me as we explore:

Business Operating Systems (BOS): Master the frameworks that drive success.

AI for Entrepreneurs: Practical tools to save time and work smarter.
Wellness for Entrepreneurs: Breathing techniques, mindfulness, and routines for peak performance.

Big Ideas & Conversations: Stories, insights, and lessons from the cutting edge of business and life.

Whether you're scaling your business, exploring AI, or finding balance in your life, this podcast will inspire and equip you for the journey. New episodes every week!

https://www.linkedin.com/in/roycastleman/
https://allthepower.co.uk/
https://www.facebook.com/roy.castleman

About your host

Profile picture for Roy Castleman

Roy Castleman