EPISODE OVERVIEW

Duration: Approximately 25 minutes

Best For: Trapped entrepreneurs who have built something successful and now wonder if their money is actually working for them, or just sitting there while they work themselves into the ground

Key Outcome: A clearer understanding of how to make your capital work independently of your time, so you can step back from the daily grind without watching your wealth stagnate

He was 29, had over a million in his account, and walked into his boss's office to quit. They offered him more money. He said it wasn't about the money.

THE BOTTOM LINE

You built your business from nothing. You worked the long hours. You sacrificed the weekends, the holidays, the time with people who matter. And somewhere along the way, you became wealthy on paper. The thing is, your money just sits there. You're too busy running the business to think about investing properly. Too overwhelmed by the noise of crypto, AI, market chaos. Too burnt out to add another thing to your plate. Jaden Sterling knows that feeling. He made his first million by 29, built a twelve and a half million dollar real estate portfolio, then watched it all unravel in 2008 when the banks came calling. That painful education brought him full circle to what actually works: individual stocks, simple systems, and the discipline to let your money compound while you focus on getting your life back. For the last eight years, he's helped over 5,000 members find winning stocks in two clicks or less. Not because investing needs to be complicated. Because trapped entrepreneurs need simplicity that actually works.

WHY THIS EPISODE MATTERS TO YOU

Your money should be building wealth while you sleep, not sitting idle because you're too exhausted to think about it. This solves the "I know I should be investing properly, I just don't have the mental bandwidth" problem that costs you compound growth every year you delay.

Jaden's journey from corporate ladder to losing everything to rebuilding shows you what happens when you treat learning as an investment, not an expense.

The cost of inaction is another decade of trading your health and relationships for money that isn't even growing the way it could.

KEY INSIGHTS YOU CAN IMPLEMENT TODAY

The moment you realise you're making someone else richer instead of yourself, everything changes. Jaden was a regional vice president at Citigroup, being paid well, and still felt held back. That inner knowing that there's something more, that's not dissatisfaction. That's your signal. The consequence of ignoring it is another five years of the same exhaustion.

Pay for expertise or pay with pain, there is no third option. Jaden spent $10,000 on a one hour consultation with a real estate expert. She told him to do a lot line adjustment, carve out a parking lot, separate a property. That single insight made him an extra million dollars. The trapped entrepreneur who refuses to invest in coaching or consultants isn't saving money. They're paying the underground in wasted years and costly mistakes.

Simple systems beat complex strategies every time. Jaden turned $70,000 into over a million by buying one stock and adding to it monthly. Dollar cost averaging. Nothing fancy. Nothing overwhelming. Just consistency. What happens because of this approach: you stop trying to time markets, you stop the analysis paralysis, you actually build wealth.

AI is a 60% tool, not a 90% solution. The hype says AI does everything. The reality is different. It forgets context after five or six prompts. It hallucinates Saturday options contracts that don't exist. The trap is thinking AI will solve your problems. The freedom is using it as a thinking partner while you remain the strategist.

Your money should work as hard as you do. Most trapped entrepreneurs have capital sitting in accounts, earning nothing meaningful, because they're too busy working in the business to work on their wealth. Individual stocks, chosen with a clear system, can outperform packaged products without requiring you to become a day trader.

GOLDEN QUOTES WORTH REMEMBERING

"It wasn't about the money. It was about knowing that there was something more inside me that wanted to express itself. And the only way to do that was to quit my job." , Jaden Sterling

"If the coach has earned their weight in gold with asking the right questions which allowing you to open your mind to another avenue or possibility." , Jaden Sterling

"I paid consultants $10,000 for one hour. And that hour allowed me to make hundreds of thousands of dollars." , Jaden Sterling

"AI should empower us to be more human. If you can offload 70% of monotonous tasks to AI, you can empower your team to connect more, engage more, think more." , Roy Castleman

"You only learn in two places. You can get coaching or you can learn from hard times." , Roy Castleman

QUICK NAVIGATION FOR BUSY LEADERS

00:00 - Introduction: Meeting Jaden Sterling and his journey from corporate finance to entrepreneurship

02:15 - The Million Dollar Exit: Why Jaden walked away from Citigroup at 29 with over a million in his account

05:40 - Real Estate Education: How he built a 12.5 million dollar portfolio and what 2008 taught him about leverage

09:30 - The $10,000 Hour: Why paying consultants properly made him an extra million dollars

12:45 - The State of Money Today: Debt based economies, crypto, silver, gold and what actually holds value

16:20 - AI Reality Check: Why artificial intelligence is a 60% tool and how to use it properly

20:15 - Sterling Stock Picker: How to find winning stocks in two clicks or less

23:40 - Conclusion: Where to connect with Jaden and next steps for building real wealth

GUEST SPOTLIGHT

Name: Jaden Sterling

Bio: Jaden Sterling is the founder and CEO of Sterling Stock Picker, an award winning platform helping over 5,000 members find winning stocks through clear analytics and simple systems. With experience at Merrill Lynch and Citigroup, Jaden built and lost a real estate empire in 2008, then channelled that painful education into helping regular people build real wealth without the complexity of Wall Street.

Connect with Jaden:

Website: sterlingstockpicker.com

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

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

Instagram: https://www.instagram.com/sterlingstockpicker

Facebook: https://www.facebook.com/SterlingStockPicker

YOUR NEXT ACTIONS

This Week: Look at your current investments. Are they actually growing, or just sitting there because you're too busy to think about them? Write down what compound growth you've missed in the last year by not having a system.

This Month: Try the 30 day trial at sterlingstockpicker.com and see if a simple stock picking system could work alongside your business, not demand more of your time.

This Quarter: Calculate what one hour with the right consultant or coach could be worth to you. Then find that person and pay them what they're worth. The alternative is learning the hard way for another five years.

EPISODE RESOURCES

Sterling Stock Picker Platform: sterlingstockpicker.com (30 day trial available)

Notion (database software mentioned for AI memory management)

Claude AI (recommended over ChatGPT for business use)

ChatGPT/Gemini (mentioned as tools with specific purposes)

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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

1

Good morning, good afternoon, good evening, wherever you are in

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the world. I'm here today with Jaden Sterling. He's doing

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something on the edge of trading and AI and all

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these kind of things. So I thought it'd be interesting

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to have a chat with him and see how he

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sees the world as we go forward. Welcome to the

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podcast, sir. Thank you so much. Thanks for having me.

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Pleasure to be here. So tell me, just first of

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all, I normally ask entrepreneurs if you were in the

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real world of working and now you're not, and I

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love that story. What was that time in your life

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you said, I've had enough of working. I'm not employable

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anymore. I remember it vividly. I was 29 years old.

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I was working for Citigroup, and I was a regional

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vice president for them. Had worked my way up the

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ladder. The decade of the 90s. And business was great.

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I was being paid well. I was in the financial

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industry. I knew I wanted to be in that industry.

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And I just felt like something on the inside. I

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just felt being held back, it was the strangest thing.

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And with that really strong inner feeling, I had invested

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well during the 90s. I bought one stock, and it

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tripled in value, and it allowed me to actually have

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over a million dollars in my account at the age

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of 29. So I said to myself, I'm single, have

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minimal expenses. What am I doing? I'm working for someone

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else, making them richer. And really, that was it. I

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just decided. I flew to New York, saw my boss,

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and I said, hey, I'm out of here. And he

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thought it was a ploy to get more money. So

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he said to me, what if I don't accept your

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letter of resignation? Like, how much can we pay you

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to keep you? And I said, oh, it's not about

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the money. And I sincerely meant that it wasn't about

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the money. It was about knowing that there was something

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more inside me that wanted to express itself. And the

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only way to do that was to quit my job.

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And what were the first steps like? It goes into

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being a really exciting and scary and exciting

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and more scary kind of initial thing, because we don't

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know, right? We step out. I love that about entrepreneurs.

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We step out and see a problem in the world.

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We think we can solve it. We step out into

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it. We don't know what we're doing. We. But we

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figure it out. I rode all the ups and downs

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on that roller coaster. And the funny thing was, I

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was really drawn to real estate at the time. Nothing

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to do with stocks. Although my portfolio helped me buy

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stocks because I would put my IRA up as collateral

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to buy an eight unit apartment building. And then we'd

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make some capital improvements to it, increase the rents and

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I'd get my IRA back. So it was like literally

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a no money down deal kind of thing. So I

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used my stocks as a tool, a leverage tool to

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buy more assets, which was basically apartment buildings, commercial

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real estate. And I knew I had to learn about

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money, big money. So I started my business, grew to

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12 and a half million dollars in seven years. And

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this is back in the early 2000s when that was

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a decent amount of money. I really wanted to learn

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more about how money worked, how the flow of capital

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worked, how debt worked and how lever worked. And I

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got that education through real estate. Although at the end

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quite painful because it was 0809 timeframe when the markets

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unraveled and I was like, oh, just the banks were

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calling me, like, hey, you've got a $2 million loan.

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Your portfolio, this one property, went from 4 million of

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value, it's now down to 2 million. You have to

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come up with a million dollars for the loan to

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value. And I said, could I just drop the keys

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off? So it was a lot of key dropping off

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if. And I learned a lot. But it brought me

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right back to my roots of stocks and how powerful

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stocks are, because I would never have had that experience

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in real estate if I hadn't started investing in stocks.

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So my, my, my like passion mission came full

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circle at that moment in 09 when I stepped into

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teaching more about investments, how to grow assets, how to

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start really building wealth, not just staying alive. 2008,

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what a year that was. I went from a very

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full order book to an empty order book in three

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weeks. Yeah, we made it, we wrote it through, we

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got out the other side. And you're right. I think

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the thing about what we do is that you only

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learn from the hard times. Right? You can learn in

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two places. You can get coaching or you can learn

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from hard times. That's right. You have to be ready

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to get coaching as well. I wasn't ready to get

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coaching because I had an arrogance to me, which I'm

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ashamed to admit that I thought I knew how to

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do it, but what I did is I sat there

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and I looked at other people doing it and thought,

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I can do it like that. I didn't have the

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experience, I didn't have their knowledge, I hadn't learned their

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lessons, I hadn't done any of the things they had

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done to earn that knowledge. And I didn't want to

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pay a coach 100 grand to come and coach me.

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But I eventually paid the underground and Learned more in

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6 months than I learned all the time before that.

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Those two things I think that ability to be coachable

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but also to learn from your lessons. Either make the

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mistakes and learn the hard way or go and find

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someone that's done it before. You're so right. If the

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coach has earned their weight in gold with asking the

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right questions which allowing you to open your mind to

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another avenue or possibility. For me, it didn't end up

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being coaching. It ended up being consultants who I hired.

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And I would pay consultants $10,000 for one hour. And

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that hour allowed me to make hundreds of thousands of

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dollars in real estate. I brought in a consultant. Funny.

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I had a property and it was a 16 unit

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apartment building and there was a parking lot and another

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home and a garage apartment above that and then actual

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garage units in the back, 10 of them behind the

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building. Profitable, proper. I bought it as a conversion. I

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wanted to convert it into affordable housing for people. And

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I brought this consultant out and she charged me $10,000.

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But she said to me, if I were you, I

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would do a lot line adjustment and I would carve

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out the parking lot for the apartment building and remove

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the home off the parcel and keep that separate. That

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was brilliant. I had never thought about it. She said

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just do a curb cut so people can pull into

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the parking lot. It was the easiest thing I ever

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did. And that allowed me to make an extra million

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dollars on that property. When you hire the right professionals,

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pay for their time with what it's worth, it's just

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a no brainer for sure. And now we're in a

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different world. Everything has changed. We have every financial system

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crumbling around us. We have Bitcoin doing whatever Bitcoin is

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doing, the share market trading in all sorts of random

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ways. And we have AI. And AI is going to

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be the biggest single change we see in our lifetimes.

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It's the biggest single opportunity, but it's also going to

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be the biggest pain. The most interesting thing I find

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about this, we are still in a debt based economy

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and debt makes the world go round. And at some

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point the music's going to stop and there aren't going

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to be enough chairs. It's interesting to me how this

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blockchain crypto has really come about to start opening people

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up to the idea. Because as far as I can

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tell, there's going to Be a real push for a

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global new world order situation going on where there's digital

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currency and that's going to be a big pill for

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a lot of people to swallow. But with the advent

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of Bitcoin and everything that's gone on recently, the last

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12, 13 years, people are used to it, they're accustomed

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to it, they like it. It's been a fairly easy

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way to transact or move money. But the reality is

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it's the most tracked and traced because there's a ledger

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for every single transaction and everyone has access to it.

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So I'm hoping that cash doesn't go away, but ultimately

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I think silver and gold reign supreme out of all

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this. That's my belief. I'm always buying. I've got these

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silver bars on my desk that I just bought 10

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ounces each and I'm always buying coins and things like

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that because I think when you talk about sound money,

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that's not a debt based economy, that's a real money

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economy. And I think there's going to be a place

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for that. We don't know when we don't have a

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crystal ball, but it could come sooner than later. I

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think the silver one's quite interesting because gold by nature

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is used in jewelry and some electronics. Silver is

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actually a traded commodity that people need to do stuff

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with and the supply is becoming much harder to come

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by. So where you were able to go and buy

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all the time and that supply and demand thing really

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on the bitcoin side, Bitcoin's big thing is there's a

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limited demand, a limited supply and there seems to be,

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we're moving towards our silver quite rapidly and it's in

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so many applications, solar panels, data centers, hardware. It's

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used so often and there's no replacement for it. It's

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just such a great conductor. Like to your point about

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AI, it will continue to boost and use silver quite

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a bit. And so I think, I don't know, I'm

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still on the fence about this whole AI situation because

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I was so burnt in the early 2000s with technology

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because they were pushing technology that hadn't even been invented

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yet. If what we're hearing is true, there's going to

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be a data center on every single corner. It's just

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bizarre, like how Starbucks was a long time ago. It's

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going to use a huge amount of resource electric, it's

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going to probably pollute our water. It's just not going

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to be the best situation. However, if just half of

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the data centers that they're talking about are going to

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be built that is going to require a tremendous amount

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of copper, a tremendous amount of power and silver and

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we can make money on that, we can capitalize on

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that because I think AI it's interesting, Bloomberg had an

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article yesterday talking about AI and maybe it's not quite

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all that it's cracked up to be. So I thought

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it was interesting that a mainstream publication finally has come

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out and started questioning AI and how it. We've

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been told that it learns on its own all that

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it replicates itself. It gets smarter. Her take was that

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doesn't at all happen. It doesn't know how to do

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that. I use Chat GPT all the time and it's.

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I'll ask it to pick out options contracts and it'll

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show me a Saturday expiry which doesn't even exist for

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options. I think we just take it with a grain

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of salt. What do you think about all that? I

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think we've been sold very much this dream that AI

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is a 90% tool. Right? Yeah. And AI is in

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my mind is a 60% tool. What it can do

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very well to your point. Firstly, ChatGPT died in version

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5 in my mind. I got divorced from ChatGPT. I

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had this lovely relationship with Chad. They built Chad it

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and I felt like I was married again. I moved

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over to Claude. Yeah, Claude streaks different. Secondly, I've

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been in this for three and a half years. I

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run three IT companies and so I've always been more

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tech savvy and I've been really looking at the thought

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of how we can use AI effectively. And one of

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the things I do now, I don't know if you've

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come across notion as a database option. No, it's a

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bit of software basically and it's a database software. And

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the problem with every AI tool you have, to your

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Bloomberg lady's point, every time you go into a new

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chat window, you lose. It doesn't learn anymore. Everyone's got

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the learning turned off, so it doesn't learn anymore. Right.

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So Claude, for example, is Learned up until 202025 in

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March. That's as much information as we got. However you

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can tell it to go and learn more on every

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chat. But also as you walk through your day, if

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you're trying to store everything in your large language model

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chat to be lord, whatever it is, it doesn't. It's

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never going to remember it. What I do is I

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say I'm working on this little thread at the moment

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now put that information that I Just learned, which I

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haven't had before, and put into my notion, and it

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just puts into my notion. And so I keep on

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offloading all the AI as it comes, as useful information

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comes to me, I offload it into a separate brain.

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So I think outside my brain. Right. And what it's

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allowed me to do is it's allowed me to expand

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my thinking power massively. So in your example of the

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options contracts that you want to go and deal with,

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if you're offloading that all the time and you're getting

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it to check online all the time when you do

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it, it's going to give you a totally different result.

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So it's really about how do you use it in

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a way that it's designed to be used and we

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haven't been told how it's designed to be used. And

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another big thing is the AI won't tell you how

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it's designed to be used. Yeah. So Claude, I will

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say to Claude, I want you to go and build

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a Claude skill. All right? So it's like a GPT

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and Claude won't know how to build the Claude skill

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to the current recommendations because it's got no knowledge of

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it. Okay. But Claude is very good. It's like your

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brilliant autistic 17 year old nephew and you can

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tell him every single math question in the world and

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he's got it, but five minutes later he's forgotten that

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question and it's gone. Every five or six prompt that

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you put in, you lose that entire context. So yeah,

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even if you're logged in and you got the threads,

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it'll only look at the last five or six threads

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and then we'll try and compact them. Yeah. And they'll

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tell you it's got a million context window and all

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these great things and maybe it'll get better, but that's

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just not the truth. Yeah. Okay. And what I'm looking

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at is, as a business owner and a professional, what

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can you do? How can you fix this problem I've

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got now? And it's not just understanding your problem, it's

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understanding how to automate and then it's how do I

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make AI do this for me? Absolutely. Yeah. And

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I think a lot of companies are using it as

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an excuse to lay off workers that's going to bite

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them in the rear end like nothing else. I firmly

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believe that AI should empower us to be more human.

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So if you have 10 people in your team and

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you can offload 70% of their monotonous tasks, they don't

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like doing to AI and you can empower them to

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connect more, you can empower them to engage more. You

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can give them the tools so that they can think

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more and do the things that we've forgotten how to

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do over the last 50 years, which is really activate

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the thinking part of your brain and you can let

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them work six hours a day instead of 10. You

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know, you're going to have a very happier team who's

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able to do 10 times the work going to come

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in if we can do that. I like that. I

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like that vision. Let's keep that be great that that

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came through. I love it. I'm doing it all the

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time. Yeah, good. I'm doing now myself with all these

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different operations, but in one of the operations I'm doing

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the work of what would be a six or seven

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person team and I'm doing it to a way more

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efficient and effective way than they would and with the

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use of AI with Claude or. Yeah. And did you

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say Claudette? No, I said Chad it. So Chat GPT

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Chad. Okay, here's my buddy. And then they killed Chad

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and they made the birth ched. It's a latest version

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of ChatGPT. I don't really get on with it all.

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Yeah, you have two pages of outputs when you ask

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one simple question. Yeah, Claude doesn't do that at all.

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Okay, so you prefer Claude over anything else. There's tools

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for tools. What's the right purpose of that tool? Claude

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has got certain purposes. Jen Spot Gemini's got certain purposes.

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It takes a while to understand what they are, but

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definitely, yeah, Claude is built for corporates, is built with

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security in mind. That's very good at writing and you

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can do all sorts of things in the background. Yeah.

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We're just starting to onboard Claude into our systems. Yeah,

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we're happy to have a chat with you at some

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point if you want to. I look forward to it.

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So tell us what you're doing at the moment. Your

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current. Yes. So for the last eight years I've built

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a software called Sterling Stock Picker with my partners and

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it came from. I started doing some money mentoring for

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folks in 09 and many worked with thousands

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of people worldwide. And one of my students asked me

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one day from Canada, she said, I love what you're

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teaching me, but could you build software around this? And

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I thought, well, I'm not a software developer. But I

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said that's a really interesting idea. I said, let me

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see what I can do with that. And then everything

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just lined up where I met my partners, they are

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developers and I told them about my vision. If we

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could help novice investors find winning stocks in two clicks

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or less, we'd be making a positive difference in the

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world. And that's what we set out to do. This

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was well before AI really started taking off. So we

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built it from the standpoint of looking at stocks through

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their pure analytics like technicals and fundamentals, financials

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and financial health. And so we have a scoring mechanism

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that shows anywhere from one to five stars. A five

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star is our extreme buy and then we chart that

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over over the years and we are currently running at

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about 62% above the sector averages in terms of return

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for the last 30 days. So we've really developed an

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awesome platform that helps people invest their money, build a

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portfolio. Because for me personally, it goes right back to

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buying stocks. They're my 20s buying that one company that

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tripled in value and I added to it every month,

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dollar cost average and turned 70,000 into over a million.

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So I know that individual stocks work rather than mutual

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funds or other packaged products. And how if people want

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to get hold of this, do you have a demo

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for them to look at, a trial for them to

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try? We do. We have a 30 day trial. We

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have over 5,000 members on our platform. So it's a

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robust platform with a lot of engagement and it's simple.

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It's sterling, like sterling silver, which is my last name.

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Sterling stockpicker.com. cool. I will make sure I've got all

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your details in there and if people want to reach

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out to you, what's the best way to get you.

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That is the best way as well. Through the platform

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I have a whole team that processes any input that

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comes into our platform and I receive the emails and

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I personally answer them as well. Thank you. So it's

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been a pleasure speaking to you and I hope you

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have a great day. Thanks for coming on the show.

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Thank you. Thank you very much. I really enjoyed it.