Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
Release Date: 01/15/2026
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...
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What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
Money School Podcast
When entrepreneurs think about selling a business, they picture a clean formula: EBITDA × multiple, a “strategic buyer,” and a smooth six-month process that ends with a big wire hitting their account. What almost no one pictures is the real complexity behind an exit. The psychology, the timing, the identity shift, the risk calculus, and the reality that most founders aren’t just selling a business… they’re handing over a lifetime’s work to someone else. That’s the part nobody warns you about. Most owners obsess over valuation, but the real danger is preparing too late,...
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The Smartest Money Move You’ve Never Considered w/ Dr. Jeff Seibert
Money School Podcast
When people think about wealth-building, they picture stock charts, IRR calculators, and “smart” portfolios engineered by advisors. What they never picture is a dentist quietly building long-term wealth through trees or using a whole life policy as the cheapest, most flexible source of capital in his business. That narrow view hides one of the most powerful truths about high-net-worth families today: the real wealth is built through boring, patient, predictable decisions that compound for decades… not the high-IQ investing most people obsess over. Most high earners are told to focus on...
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How to Escape the Debt Cycle the Banks Want You Trapped In w/ Harrison George and Christy Vann
Money School Podcast
For most people, debt isn’t a mistake; it’s just life. The mortgage, the car loan, and the credit cards are what everyone does. Making the minimum payments feels normal, but that actually keeps people stuck. Millions of families are drowning in debt, and they’re barely managing. They’re working hard, keeping up with their bills, but almost every dollar they earn goes right back out in interest. They’re not moving forward; they’re treading water. The hard part is, they’re not doing anything “wrong.” They’re doing what the system taught them to do: stay cash-poor while the...
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Non-Food Franchises: A Shortcut to Entrepreneurship, Wealth & Tax Benefits w/ Jon Ostenson
Money School Podcast
When people hear “franchise”, they immediately picture a drive-through window and a fryer in the back. That narrow view hides one of the most accessible and profitable paths to business ownership today: non-food franchising. We’ve been taught that entrepreneurship means starting from scratch: writing business plans, building systems, and hoping your idea sticks. Franchising flips that equation. You’re not reinventing the wheel; you’re stepping into a proven system with training, marketing, and infrastructure already built. The best part? You can own a business that runs...
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Why Most Pro Athletes Go Broke (and How Rashad Jones-Jennings Beat the Odds)
Money School Podcast
From the outside, pro athletes look like they’ve made it; like they’ll never have to worry about money again. Multi-million-dollar contracts, highlight reels, and luxury lifestyles suggest money will never be an issue. But behind the scenes, most players are one injury, one bad decision, or one contract away from financial ruin. The truth is, the average NBA career lasts just 4 years. Taxes, agents, lavish spending, and poor planning chip away at earnings until the fortune is gone, and with no plan for life after the game, many athletes end up broke and starting over from scratch....
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Stacking Wealth: The 5 Returns You Can ONLY Get From Real Estate Investing w/ Axel Meierhoefer
Money School Podcast
Most investors don’t fail because they pick the wrong stock or buy into the wrong trend. They fail because they never define success for themselves. They chase returns without knowing what a win actually looks like. Without a clear target and purpose, investing becomes guesswork, and the chances of losing money are higher. Worse, they choose methods that look cool instead of ones they actually understand. They don’t give themselves a hard out, so they hold too long or sell too soon. And often, they pick investment vehicles that only pay them in one way. That’s where real estate...
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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