Mistakes That Take Wealthy People Out in a Downturn w/ Arthur Hood
Release Date: 12/30/2025
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...
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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...
info_outlineWhen 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 worth doesn’t equal safety, how paper wealth quietly evaporates when cash dries up, and the specific decisions that turn manageable situations into permanent losses.
Arthur explains why some asset classes keep working under pressure while others break, and why deals that depend on a clean refinance or exit are often the first to fail.
Most importantly, we dig into the moves that allowed certain investors not just to survive the worst downturns, but to stay in control long enough to come out stronger on the other side.
About the Guest
Arthur Hood is an experienced entrepreneur with a diverse portfolio of businesses spanning commercial real estate, entertainment, and hospitality. His venture Your Space America, focuses on the booming self-storage industry, one of the most resilient and high-performing asset classes in U.S. real estate. As Executive Vice President of the company, Arthur has overseen the development, construction, and ownership of large, climate-controlled self-storage facilities. These properties have become increasingly sought after by institutional investors due to their consistent performance across economic cycles. With self-storage offering an average annual return of 17.3% from 1994 to 2023, the industry has grown exponentially, driven by high demand from individuals, small businesses, and transitional populations. Your Space America is capitalizing on this growth by creating state-of-the-art facilities that cater to modern consumer needs, offering not only safe, secure storage but also a wide range of specialized services, including climate-controlled units for sensitive inventory and documents. In addition to his work in self-storage, Arthur is the owner of HV Entertainment LLC, which operates a growing portfolio of lounges and nightclubs across Texas, Georgia, Alabama, and Chicago. Furthermore, as Managing Member of HV Properties LLC, Arthur has been instrumental in acquiring, developing, and selling both commercial and residential real estate across the U.S. The company’s real estate holdings span Florida, Texas, and Alabama, with a focus on value-added opportunities. From large-scale developments to residential projects, Arthur’s leadership has helped expand the company’s footprint and establish a strong presence in multiple high-demand markets. His expertise across these industries, combined with a strategic approach to growth, has positioned him as a significant player in both commercial real estate and the entertainment sectors. To learn more, go to https://arthurhood.com/ or send an email to info@arthurhood.com.
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.