Inside a $1.3B Portfolio: What Most Investors Get Wrong w/ Jonathan Steele
Release Date: 05/14/2026
Inside a $1.3B Portfolio: What Most Investors Get Wrong w/ Jonathan Steele
Money School Elite
Diversification sounds straightforward in theory, but in practice, portfolios don’t behave the way most people expect them to. Exposure is layered, concentration often shows up in places that aren’t immediately obvious, and decisions that feel like you’re spreading risk can quietly lead to doubling down on the same themes. Once you start looking at portfolios this way, the question shifts. It’s no longer just about what to add, but whether that exposure already exists, and what role it’s actually playing. In this episode of Money School Elite, I sit down with Jonathan Steele, who...
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The Tax Strategy Making Family Offices Rethink Bitcoin w/ Eric Runge
Money School Elite
Most investors think Bitcoin is about price. At the high-net-worth level, a far more important conversation is happening around taxes. Because Bitcoin isn’t treated like a stock or a business. It’s treated as property. And that classification opens up strategies around taxation and capital movement that simply don’t exist in traditional asset classes. And once you understand that, the way you evaluate Bitcoin starts to change. Most high-net-worth investors don’t dismiss Bitcoin because they don’t understand it. They dismiss it because, from where they sit, it doesn’t meet the...
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Real Wealth Is Built Before the IPO, But You Can’t Access It w/ Mona DeFrawi
Money School Elite
Most people don’t realize that a large portion of real wealth is created before companies ever reach the public markets. In private companies, early-stage investments, and entrepreneurial ventures, growth happens the fastest. For a long time, that part of the market has been largely inaccessible to retail investors, reserved instead for institutions and high-net-worth individuals. And that has played a significant role in the growing gap in wealth. In this episode of Money School Elite, I sit down with Mona DeFrawi to unpack how this system actually works and what’s starting to change....
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The Fastest Way to Grow Your Business (It’s Not Strategy) w/ Greg McDaniel
Money School Elite
Most people think success comes from strategy…better marketing, better positioning, better timing. But what if that’s not the lever at all? What if the thing that actually drives growth isn’t what you take, but what you give, freely, consistently, and without any immediate expectation of return? Because when you really look at how businesses grow, how opportunities compound, and how networks form, the pattern isn’t subtle. The people who seem to “get ahead” aren’t always the smartest or the most tactical. They’re the ones who become connectors, who create value before...
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Real Estate Investing Isn’t Complicated, You’re Just Doing It Wrong w/ Joel Miller
Money School Elite
Most people don’t associate residential real estate investing with enjoyment. Between tenant issues, maintaining properties, and financing problems, it can really be a headache. But the problem isn’t the asset class; it’s how you approach it. Because real estate, when done right, is actually one of the most forgiving businesses you can be in. What separates the people who enjoy real estate from the ones who burn out isn’t intelligence or even experience. It’s getting around the right people and getting the right education. What kind of information should you be consuming? How...
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Smart Money Is Leaving Cash Behind, Here’s Where It’s Going Instead w/ Ben Reinburg
Money School Elite
Most investors believe that holding cash during uncertain markets is the safest move. If you stay liquid, wait for clarity, and avoid risk, you’ll be in a better position when opportunities come… or at least that’s the thinking. But what many high-income earners and investors don’t realize is that cash sitting idle isn’t neutral; it’s losing ground. Between inflation, taxes, and missed opportunities, capital that isn’t deployed is quietly working against you. And while many investors are pulling back, the most sophisticated capital, family offices, institutions, and sovereign...
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What’s Really Happening In Real Estate Lending Right Now? w/ Jonathan Yoo
Money School Elite
Many real estate investors believe success comes down to one thing: access to capital. If you can borrow money easily, scale quickly, and leverage aggressively, the thinking goes that your portfolio will grow faster. But what a lot of investors are learning right now is that capital alone doesn’t create successful deals. Structure does. In today’s lending environment, small mistakes in leverage, underwriting, or financing strategy can turn what looked like a solid deal into a long-term problem. And many investors don’t realize where those risks actually show up until after the...
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The End of Traditional Financial Advice? w/ Stefan Astheimer
Money School Elite
For a long time, truly personalized investment advice has been something only the ultra-wealthy could access. If you have tens of millions of dollars, you can hire advisors who don’t just sell you products. They build strategies around your entire financial life. But everyone else gets standardized portfolios and is told to keep contributing to their retirement accounts and stay the course. That’s starting to change. A new approach to financial advice is emerging, one built around a fee-for-service strategy instead of product sales. Instead of paying someone based on how much money they...
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What Banks Actually Look For Before Funding a Business w/ Sebastien Boyer
Money School Elite
Starting a business is often framed as a simple equation: have a good idea, take it to the bank, and secure the funding. But the reality is very different. Most business owners aren’t rejected because their idea is bad. They’re rejected because they approached the capital the wrong way. So many deals fail before they ever reach underwriting, and it’s not because of the opportunity. It’s preparation, structure, and understanding how lenders evaluate risk. Banks aren’t investors looking for the next big idea. They operate under strict guidelines, regulatory frameworks, and underwriting...
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The Financial Reality of Pro Snowboarding and How to Escape It w/ Stevie Bell
Money School Elite
Every athlete knows the music will eventually stop. Whether you walk away on your terms, are forced out by injury, or have a contract that doesn’t get renewed, your career will inevitably end. In leagues like the NFL, NBA, or MLB, that ending can still leave you financially set. You might walk away with generational money. In action sports, that’s rarely the case. A pro snowboarder can start earning real money in their teens. They can travel the world, land major sponsors, build a name, and live what looks like a dream career. But very few retire with enough money to last a lifetime. The...
info_outlineDiversification sounds straightforward in theory, but in practice, portfolios don’t behave the way most people expect them to.
Exposure is layered, concentration often shows up in places that aren’t immediately obvious, and decisions that feel like you’re spreading risk can quietly lead to doubling down on the same themes.
Once you start looking at portfolios this way, the question shifts. It’s no longer just about what to add, but whether that exposure already exists, and what role it’s actually playing.
In this episode of Money School Elite, I sit down with Jonathan Steele, who manages over $1.3 billion in assets, to unpack how modern portfolios are actually structured and why many of the assumptions investors rely on don’t always hold up.
Jonathan works closely with high-net-worth clients, helping them think about capital not as a collection of individual positions, but as a system of exposures that interact in ways that aren’t always obvious.
We get into why Bitcoin and precious metals are often grouped incorrectly, how indirect exposure through index positions can lead to unintended concentration, and why holding cash in the current environment is less about being defensive and more about maintaining flexibility while still earning a return.
About the Guest
Jonathan Steele, CFA®, is Co-founder and Chief Investment Officer at One Wealth Advisors, where he leads investment research and portfolio management for high-net-worth clients. With over 20 years of experience, Jonathan specializes in portfolio construction, tactical and strategic asset allocation, and behavioral finance. As a Chartered Financial Analyst® and member of the CFA Institute, his work focuses on how portfolios are structured and how different exposures interact within a broader system. Outside of investing, Jonathan is deeply involved in the arts, having served on the advisory boards of Bard Music West and Vanguard Music and Performing Arts. He also mentors students across finance, technology, and engineering, and supports local organizations, including Muttville Senior Dog Rescue and the SF SPCA. To learn more, go to https://onewealth.net/.
About Your Host
From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America’s #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is the founder of The Money School™ and Money Mentor for The Money Multiplier.
His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.
Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans, delivering the financial knowledge that fuels lasting freedom.
Resources
Private Money Guide: https://go.moneyschoolrei.com/book-podcast
Wealth Wednesday Webinar: https://go.moneyschoolrei.com/wednesday-webinar-podcast
Mapping out the Millionaire Mystery: https://go.moneyschoolrei.com/newbook-podcast