Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
Release Date: 01/15/2026
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...
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How to Stop Carrying Real Estate Risk and Still Make Money w/ Scott Jelinek
Money School Podcast
Most investors never question the hierarchy they’re operating in. They borrow money, take on operational risk, manage tenants, absorb volatility, and send a large portion of every payment upstream to the lender. If something breaks, if a tenant stops paying, if the market turns—the obligation to the bank doesn’t change. This is the Mr. Burns model: the banks sit at the top of the building collecting checks, while everyone else does the work below. The slow flip model flips that hierarchy entirely. Instead of rehabbing properties or betting on appreciation, the investor...
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Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
Money School Podcast
One 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...
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Money Has Feelings: Why Wealthy People Still Feel Miserable w/ Shannon Ryan
Money School Podcast
Many people who work hard to build and protect their wealth assume that once they “make it,” everything will finally feel good, secure, calm, and settled. But most people don’t discover the truth until they’re already successful: money doesn’t quiet the fear. It often makes it louder. The pressure gets higher, and the decisions get heavier. The same stress, anxiety, and old beliefs they carried before wealth simply move with them into a larger life. That’s the part no one prepares high earners for: the emotional weight that grows alongside the net worth. And it shows up everywhere:...
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Mistakes That Take Wealthy People Out in a Downturn w/ Arthur Hood
Money School Podcast
When people think about economic downturns, they usually assume the damage happens at the bottom. What rarely gets talked about is how many wealthy people lose everything — not because they didn’t have assets, but because they trusted strategies that only worked when conditions stayed favorable. In this episode, I’m joined by Arthur Hood, an investor and entrepreneur who has built significant wealth across multiple market cycles and watched firsthand how high-net-worth individuals get taken out when liquidity tightens, exits disappear, and assumptions stop holding. We talk about why net...
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The Trucker Financial Trap and How to Escape It w/ Dexter Holiday
Money School Podcast
For a lot of truckers, you can make great money hauling loads across the country, but it comes with a catch: the wheels have to keep turning for the money to keep coming in. There’s no automatic runway to financial freedom, no built-in exit strategy, just the quiet expectation that you’ll drive until your body says you can’t. And the obvious alternatives like owning trucks, hiring drivers, scaling through fleet operations aren’t as simple or as stable as they sound. Most truckers end up in a loop that looks a lot like the rest of America’s financial reality: you earn, you...
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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