Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
Release Date: 01/15/2026
What’s Really Happening In Real Estate Lending Right Now? w/ Jonathan Yoo
Money School Podcast
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 Podcast
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 Podcast
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 Podcast
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...
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The Real Reason AI Valuations Are So High w/ Daniel Nikic
Money School Podcast
In today’s market, AI valuations are expanding faster than fundamentals can justify. Companies with minimal free cash flow are being priced as if dominance is already secured. Capital continues to circulate between venture portfolios, strategic partners, and ecosystem incumbents, reinforcing growth narratives that assume liquidity remains abundant. But markets don’t reward narratives forever. When growth slows or capital tightens, the question shifts from projected upside to structural durability. Does the business generate real cash? Does it control proprietary data that compounds...
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Wealthy People Upgrade Everything… Except This w/ Ted Ryce
Money School Podcast
As people make more money, they tend to get sharper about almost everything. They think long term, manage risk better, hire experts, invest wisely and optimize their businesses and portfolios. But when it comes to health, a lot of people are still running the same basic playbook everyone else is. Standard labs, five-minute appointments, and just waiting until something breaks. When you want to level up in every area of your life, the conversation shouldn’t be, “Am I sick right now?” It should be, “Where am I headed, and how early can I catch it?” The people who are strong,...
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“I Can’t Afford a Coach” Is Why You’re Stuck w/ Patrick Engasser
Money School Podcast
When you’re struggling in business or just starting out, the last thing you think you need is a coach. You think you can’t afford it, you’re not ready, or you should wait until you have better results first. But every time someone feels like that, that’s actually when they need a coach the most. Most people see coaching as something you do later. Once things are going well, the money is there, and you’ve “made it” enough to deserve help. But that’s not really how it works. Coaching isn’t there to reward you for being successful. It’s there to stop you from wasting years...
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Putting Your Money in Buckets Is a Trap, Do This Instead w/ Joseph Kovacevic
Money School Podcast
Most people think financial freedom comes from earning more, saving harder, or finding the perfect investment. But the real trap isn’t income…it’s the way we’re taught to store and move money. We’re told to separate everything into neat little buckets: checking, savings, mortgage, credit cards, investments. And somehow, even when we’re “doing well,” the system still feels tight, slow, and exhausting. The traditional system is wildly inefficient by design. A 3–4% mortgage isn’t really 3–4% at all. It’s closer to 12–15% in simple interest once you account for...
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How to Stop Leaving Money Inside the Tax Code w/ Zach Newberry
Money School Podcast
Most high-income earners assume their tax situation is handled once they hire a CPA and start filing. The return gets done, nothing breaks, and it’s easy to believe that if something mattered, it would already be happening. But that assumption quietly costs people money. Not because they’re reckless or aggressive, but because compliance gets mistaken for strategy, and basic leverage never gets activated. Zach Newberry works with business owners and real estate investors who earn well, and still find themselves on the wrong side of the tax game. What he sees over and over isn’t missed...
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The Ultimate Investing Advantage Is…Boredom w/ Irwin Boris
Money School Podcast
Most investors never question the structure they’re investing in. They accept tight assumptions, back-end-heavy returns, and illiquidity as the price of access, assuming the payout will arrive before anything goes wrong. But when timing slips, liquidity tightens, or markets shift, those assumptions become traps. The deal didn’t fail because the idea was bad. It failed because it never paid the investor enough to wait. Irwin Boris has spent decades operating on the other side of that equation. After more than $5 billion in deal flow, he learned to treat any model that needs to be “screwed...
info_outlineOne of the biggest mistakes in personal finance is how quickly conversations turn into either/or debates. Invest or insure, trust the market, or play defense. Something is a scam, or it’s the answer.
The problem is, real financial progress rarely comes from choosing sides. It comes from using the right tools together instead of pretending one tool should do everything.
This shows up clearly in the way people talk about retirement plans. People have strong opinions about 401(k)s, especially the idea that the match is a scam. But that argument falls apart once you actually slow down and look at how it works.
That idea carries into the way people think about insurance. Insurance isn’t an investment, and treating it like one creates bad expectations on both sides. But dismissing it because it’s not an investment misses what it’s actually designed to do. The more interesting question isn’t “what’s the return,” but “what role does this play in the system?”
Being dogmatic about any tool, whether it’s a 401(k), insurance, or the market, usually leads to worse outcomes.
In this episode, the author of The And Asset and founder of BetterWealth, Caleb Guilliams, returns. We dig into the idea of giving your dollars more than one job, how money can be safe and accessible at the same time, and boring on the surface, but incredibly useful when integrated correctly.
Things You’ll Learn In This Episode
Why financial labels block better decisions
We don’t reject strategies because they fail; we reject them because of what they’re called. How does labeling something “insurance,” “investment,” or “scam” stop you from seeing its true value?
Why value matters more than rates of return
Cost only feels expensive when the value isn’t clear. What happens when you stop asking “what does this pay?” and start asking “how many jobs does my money do at once?”
Changing your mind is a sign of financial maturity
Rigid beliefs feel safe, but they often lead to bad advice. Why is the willingness to evolve a marker of credibility, not weakness?
How AI will quietly replace most financial advice models
What will happen when software can analyze, design, and optimize financial decisions faster and more accurately than most humans ever could?
About the Guest
Caleb Guilliams is the author of “The and Asset”, a podcaster, investor, speaker, and the founder and CEO of Better Wealth Solutions, a company committed to showing people how to be more efficient and control their money today while maximizing their future wealth potential. BetterWealth is a company that is fascinated with the idea of ordinary people being able to achieve extraordinary wealth. Caleb and his team have discovered proven strategies & principles that can empower anyone to create & protect real wealth. For more information, go to https://betterwealth.com/. Go to https://thewholelifesummit.com/2026 to learn more about the Summit and buy the book at https://betterwealth.com/bookstore.
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.
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