Either/Or Investing Is Destroying Your Wealth w/ Caleb Guilliams
Release Date: 01/15/2026
How to Beat Big Capital at the Bitcoin Mining Game w/ Beau Turner
Money School Elite
Most investors assume there are only two practical ways to approach Bitcoin: buy it directly and accept the volatility, or avoid it because it does not fit the framework that built their wealth. But Bitcoin mining introduces a different conversation. For most people, mining sounds too technical, too operationally complex, or too institutional to be a serious investment strategy. Servers, power, cooling, maintenance, custody, and infrastructure all make it feel out of reach for anyone who does not want to become a full-time operator. Beau Turner has built a model that changes that. Through...
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Outgrowing Your Accountant: The Tax Problem Business Owners Miss w/ Boris Musheyev
Money School Elite
Most business owners do not realize they have outgrown their accountant until the tax bill becomes impossible to ignore. The person who helped you when the business was small may have been perfectly fine at that stage. But as revenue, profit, assets, investments, and complexity grow, tax preparation is no longer enough. At a certain point, the business does not just need someone to file the return. It needs real tax planning. In this episode of Money School Elite, I sit down with Boris Musheyev, a tax strategist who works with seven-figure and multi-seven-figure business owners, to talk about...
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Wholesaling Isn’t Just A Beginner Real Estate Strategy w/ Chris Logan
Money School Elite
Most investors think wholesaling is just the entry-level side of real estate. At the strategic level, the better conversation is about deal flow. Because in a market where seller motivation is rising, buyers are more selective, and many casual wholesalers have left the business, the opportunity is different from what it was a few years ago. The edge is not simply finding properties. It is knowing how to identify distress, control the contract, understand buyer demand, and move before the rest of the market sees the opportunity. That is where wholesaling becomes more interesting than most...
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The Difference Between Watching Stocks and Owning Businesses
Money School Elite
In today’s market, investors with real capital are facing a difficult problem. They do not want to be reckless. Equities feel expensive, private credit has shown signs of stress, rates remain elevated, and the usual recession signals have been flashing for longer than many expected. But they also do not want to hide in safety so long that they give up years of compounding. That is where the conversation around risk has to get more precise. The question is not simply whether to be in or out of the market. It is how to structure capital so you can stay rational, preserve optionality, and...
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The Tax Credit Hidden Inside Your Business Improvements w/ Derick Van Ness
Money School Elite
For many business owners, one of the biggest missed wealth opportunities may already be sitting inside the business. Technology upgrades, software implementation, equipment, and operational improvements. These are the kinds of investments owners are already making to grow, modernize, and stay competitive. But in many cases, they may not just be expenses or deductions. They may create R&D tax credits. A deduction lowers taxable income. A credit can reduce taxes dollar for dollar. For an owner with meaningful income, that is not a small accounting detail. It is capital that can stay inside...
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The Private Real Estate Reset Wealthy Investors Need to Understand w/ Michael Pouliot
Money School Elite
Most investors think real estate performance comes down to the asset. At the high-net-worth level, the more important conversation is often about control. Because a deal is not just a building, a market, or a projected return. It is an operating system. Who manages the property? Who controls leasing, maintenance, marketing, resident communication, and costs at the asset level? Who can make decisions quickly when the market tightens, and the assumptions in the original deck no longer hold? That is where real estate investing starts to look very different. A lot of investors were comfortable...
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The Private Equity Play Hidden Inside Franchising w/ Scott Jones
Money School Elite
Most people think franchising is about income replacement. At the high-net-worth level, the real conversation is about enterprise value. Because the operators who approach franchising seriously are not just trying to buy themselves a business. They are thinking about cash flow, unit economics, operational infrastructure, EBITDA growth, private equity demand, and whether the business can eventually become attractive to a larger buyer. And once you understand that, the way you evaluate franchising starts to change. Most franchise buyers don’t miss the opportunity because they fail to...
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Wealth Lessons From the Hilton Dynasty | Why Their Money Has Lasted So Long w/ Mark Miller
Money School Elite
Most investors think wealth preservation is about performance. At the high-net-worth level, the real conversation is about structure. Because the families that keep wealth across generations are not just trying to get better returns. They are thinking about education, tax strategy, access, capital protection, charitable planning, and the systems required to make wealth last beyond one person’s lifetime. And once you understand that, the way you evaluate wealth starts to change. Most successful investors don’t lose wealth because they have never learned how to make money. They lose it...
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What Wealthy People Do After the Obvious Tax Strategies Run Out w/ Michael Malloy
Money School Elite
If you think life insurance is about protection, you’ll miss what it can do at a high net worth level. For wealthy investors, business owners, and families with meaningful assets, the question is not just where to invest. It is where long-term capital should sit, how it should be owned, how it should grow, how private it should remain, and how efficiently it can move to the next generation. That is where Private Placement Life Insurance, or PPLI, changes the conversation. Most investors dismiss life insurance because they think they already understand it. They picture ordinary...
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High Income, Financial Advisors, Still No Wealth? Here’s Why w/ Dave Wolcott
Money School Elite
Most high earners think wealth is built by earning more, saving more, and staying disciplined within the traditional financial system. At the high-net-worth level, the real conversation is structure. Because the issue is not always income. It is where the capital sits, how it is taxed, how accessible it is, how many jobs each dollar is doing, and whether there is an actual architecture around the wealth being built. Without that, even people making good money can still feel behind, overtaxed, overexposed, and dependent on a system they do not really control. Most investors follow the...
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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