Money School Podcast

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 policies, limited investment options, and a product built mainly around a death benefit. But at the high end, that framework is incomplete. PPLI is not ordinary life insurance. For the right investor, it can function as a long-term asset structure, allowing capital to grow in a tax-advantaged environment, support estate planning, simplify reporting, preserve privacy, and create a more strategic way to hold assets over time. In this episode of Money School Elite, I sit down with Mike Malloy to unpack how PPLI actually works, why wealthy families use it, and why the structure around an asset can matter just as much as the asset itself. Mike works with high-net-worth clients, families, and advisors on advanced tax and estate planning strategies using Private Placement Life Insurance. In this conversation, he explains why PPLI is not simply about buying insurance. It is about building a structure around long-term capital, especially for investors who have already used the obvious planning tools and need a more sophisticated way to think about tax efficiency, privacy, liquidity, and wealth transfer. About the Guest Michael Malloy is a founding partner of EWP Financial. With decades of experience helping global families and advisors use PPLI and Expanded Worldwide Planning to enhance tax efficiency, asset protection, and compliance. To learn more, visit https://www.ewp-financial.com/ or call 530-692-1007. 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. Resources Private Money Guide: https://go.moneyschoolrei.com/book-podcast Wealth Wednesday Webinar: https://go.moneyschoolrei.com/wednesday-webinar-podcast Mapping out the Millionaire Mystery: https://go.moneyschoolrei.com/newbook-podcast

When your income starts to scale, the instinct is to focus on earning more and delegate everything else. You build momentum, create cash flow, and then hand your capital over to advisors, funds, and institutions that are supposed to manage it efficiently in the background. The system looks sophisticated, regulated, and optimized, so it feels like the right move. But what many high-income earners and investors don't realize is that the biggest risk to their wealth often isn't the market… It's the structure their money sits inside. Because once capital is placed into systems you don't fully understand, small decisions start compounding in almost invisible ways. Fees that seem insignificant begin to erode long-term growth. Portfolios that look diversified turn out to be overlapping and inefficient. And over time, instead of compounding wealth, you're quietly leaking it. In this episode of Money School Elite, I sit down with Robert Rolih, investor, entrepreneur, and author of The Million Dollar Decision, to break down what really happens to your money after you've made it. In this conversation, we discuss why small, seemingly harmless fees can significantly delay your financial freedom, how a lack of visibility into your own portfolio creates hidden risk, and why many investors don't actually know what they own. About the Guest Robert Rolih is an entrepreneur, bestselling author, and long-term investing expert known for exposing Wall Street's hidden traps and teaching investors how to simplify wealth building. He is the international bestselling author of The Million Dollar Decision: Get Out of the Rigged Game of Investing and Add a Million to Your Net Worth, a book that has received glowing reviews from readers around the world. His mission is to reveal what the financial industry doesn't want you to know about investing, helping people greatly improve their long-term investing gains and take control of their financial future. Today, Robert has a thriving investment portfolio that serves him, not the financial industry. As a sought-after speaker, he shares his expertise with audiences worldwide, helping people avoid costly mistakes and achieve financial freedom. His ability to break down complex financial concepts into simple, engaging lessons and make investing interesting and fun has become his trademark. Robert was featured in more than 50 newspapers, websites, and TV stations, including CNBC, Yahoo Finance, Newsmax TV, Business Insider, and has had the honor of sharing the stage with renowned figures such as Robert Kiyosaki, Gary Vaynerchuk, Brian Tracy, Jack Canfield, Daniel Priestley, and many others. His international bestseller The Million Dollar Decision has been translated into several languages, including Chinese Mandarin, and published in special editions in countries such as India, Taiwan, Bulgaria, and Thailand. To get a free chapter of Robert's bestselling book, go to https://robertrolih.com/ or buy the book here. You can also join Robert's free masterclass when you go to https://robertrolih.com/masterclass. 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. Resources Private Money Guide: https://go.moneyschoolrei.com/book-podcast Wealth Wednesday Webinar: https://go.moneyschoolrei.com/wednesday-webinar-podcast Mapping out the Millionaire Mystery: https://go.moneyschoolrei.com/newbook-podcast

Diversification sounds straightforward in theory, but in practice, portfolios don't behave the way most people expect them to. Exposure is layered, concentration often shows up in places that aren't immediately obvious, and decisions that feel like you're spreading risk can quietly lead to doubling down on the same themes. Once you start looking at portfolios this way, the question shifts. It's no longer just about what to add, but whether that exposure already exists, and what role it's actually playing. In this episode of Money School Elite, I sit down with Jonathan Steele, who manages over $1.3 billion in assets, to unpack how modern portfolios are actually structured and why many of the assumptions investors rely on don't always hold up. Jonathan works closely with high-net-worth clients, helping them think about capital not as a collection of individual positions, but as a system of exposures that interact in ways that aren't always obvious. We get into why Bitcoin and precious metals are often grouped incorrectly, how indirect exposure through index positions can lead to unintended concentration, and why holding cash in the current environment is less about being defensive and more about maintaining flexibility while still earning a return. About the Guest Jonathan Steele, CFA®, is Co-founder and Chief Investment Officer at One Wealth Advisors, where he leads investment research and portfolio management for high-net-worth clients. With over 20 years of experience, Jonathan specializes in portfolio construction, tactical and strategic asset allocation, and behavioral finance. As a Chartered Financial Analyst® and member of the CFA Institute, his work focuses on how portfolios are structured and how different exposures interact within a broader system. Outside of investing, Jonathan is deeply involved in the arts, having served on the advisory boards of Bard Music West and Vanguard Music and Performing Arts. He also mentors students across finance, technology, and engineering, and supports local organizations, including Muttville Senior Dog Rescue and the SF SPCA. To learn more, go to https://onewealth.net/. 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. Resources Private Money Guide: https://go.moneyschoolrei.com/book-podcast Wealth Wednesday Webinar: https://go.moneyschoolrei.com/wednesday-webinar-podcast Mapping out the Millionaire Mystery: https://go.moneyschoolrei.com/newbook-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 trying to get there on your own. Because the real cost isn't paying for a coach. The real cost is everything you lose while you're trying to figure it out by yourself. In fact, coaching isn't even a cost. When you have the right coach, it starts paying off quickly, and it becomes one of the best investments you'll ever make in yourself. How do you know when it's the right time to get help instead of waiting it out? How did my guest build a top-performing career as a blind sales professional in one of the toughest industries there is? What can we learn from his success story? In this episode, entrepreneur, speaker, coach, and bestselling author of If I Can Do It, You Can Do It, Patrick Engasser, joins me to talk about mindset, opportunity, and why getting the right guidance early changes everything. You'll learn why the people who grow fastest aren't the smartest, they're just the ones who stop trying to do it alone. Things You'll Learn In This Episode "I can't afford a coach" is usually backwards Is it really about money, or about how much time, stress, and lost momentum it's costing you to figure everything out the slow way? The hidden mindset shift that unlocks performance What changes when you stop seeing your weaknesses as liabilities and start using them as your most powerful differentiators? How people actually "create" luck Are some people actually luckier, or are they just better trained to notice and act on the chances everyone else ignores? Success becomes addictive once you start helping others Why does coaching, leadership, and mentorship often feel more rewarding than personal wins, and how does that change the way you build your business? Guest Bio Patrick Engasser is an entrepreneur, speaker, coach, and bestselling author of If I Can Do It, You Can Do It. He started his career in the insurance industry as a top sales representative for a Fortune 500 company. He was awarded top-account closer in his third year and promoted to district manager. Patrick went on to recruit, train, and lead a seven-figure sales team while coaching several agents to successful careers in the outside sales world. He has been the recipient of the company's Top Award for Management Excellence three times for his outstanding leadership and ability to coach others to achieve their goals. Patrick has been helping aspiring entrepreneurs build their own businesses for over 15 years. To learn more and to buy his book, visit patrickengasser.com. To book a free strategy session, go to talkwithpatrick.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. Resources Get Your FREE Copy Of 'The Private Money Guide' and 'Mapping Out The Millionaire Mystery'. Keep up with us every week on our FREE Live webinars for more conversations like this, and as a BONUS, get our newest mini-ebook instantly upon signing up! https://moneyschoolrei.com/wednesday-webinar (digital download). Dive into money, mindset, and motivation videos on my YouTube Channel, and be sure to subscribe so you can be notified of our weekly LIVE streams. Find out about our next weekend workshop, and see what others are saying: https://www.moneyschooltraining.com/registration.

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 loopholes or exotic strategies. It's small, obvious decisions that never get made: spending a few thousand dollars to unlock meaningful capital, revisiting structures that no longer fit, and using rules that already apply but are never deployed. His perspective reframes taxes as a capital allocation problem, not a paperwork exercise. Instead of focusing on what gets filed, he looks at what gets converted, dollars that would disappear versus dollars that stay in play for the next investment. In this episode, we talk about why small, inconvenient costs often unlock real leverage, where high earners miss money long before "strategy" even starts, and how rules like the Augusta Rule fit into real life when you understand how to use them. About the Guest Zachary Newberry is a CPA, tax planner, and entrepreneur who works primarily with business owners and real estate investors. His practice focuses on helping clients move beyond basic tax compliance and use the tax code intentionally — connecting entity structure, real estate, income timing, and planning decisions in a way that supports long-term wealth building. He works with real estate investors, real estate-centric businesses, small to mid-sized companies, and high-income individuals. In addition to tax preparation, Zach provides ongoing tax planning and advisory services, accounting and bookkeeping oversight, and strategic consulting for clients who want their tax decisions to function as part of their broader financial and investment strategy — not just something that gets filed once a year. Email Address - zach@newberrycpa.com Instagram - @newberrycpa Facebook Business Page - https://www.facebook.com/zachnewberrycpa Booking Link - https://go.oncehub.com/ZachNewberry 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. Resources Get Your FREE Copy Of 'The Private Money Guide' and 'Mapping Out The Millionaire Mystery'. Keep up with us every week on our FREE Live webinars for more conversations like this, and as a BONUS, get our newest mini-ebook instantly upon signing up! https://moneyschoolrei.com/wednesday-webinar (digital download). Dive into money, mindset, and motivation videos on my YouTube Channel, and be sure to subscribe so you can be notified of our weekly LIVE streams. Find out about our next weekend workshop, and see what others are saying: https://www.moneyschooltraining.com/registration.

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 becomes the lender. Short-term private money is used to acquire low-dollar properties, then paid off quickly through long-term owner financing. For the first few years, the deal feels tight. Cash flow is modest. But once the private capital is gone, the asset is owned free and clear—and the payments keep coming for decades. No leverage. No refinancing risk. No dependency on market timing. What makes this approach powerful isn't just the math, though the math is staggering. It's the positioning. Ultra-affordable housing behaves differently from traditional rentals. Demand doesn't disappear in downturns. People can always move down in price—but there's a floor they can't go below. And by structuring the deal as the bank, the investor removes themselves from the operational chaos that destroys so many otherwise "good" deals. In this episode, we sit down with Scott, a real estate investor who's been in the game since the 1990s, got crushed in the 2008 collapse, and rebuilt with a model explicitly designed to survive the next downturn. We talk about why slow flips aren't about patience for patience's sake, how amortization quietly creates generational cash flow, and why the investors who win long term are usually the ones willing to give up speed early in exchange for control later. About Our Guest Scott Jelinek is an entrepreneur, coach, full-time real estate investor, and author of The Art of the Slow Flip. He has been investing in real estate since 1994 and has completed well over six hundred deals, continuing to be a leader in the industry. He has owned and operated a wide variety of businesses, from tanning salons to hot dog shops--all while buying, selling, and renting properties. Today, Scott uses his knowledge and experience to coach other real estate investors. Over 15 years, Scott built a rental portfolio of more than 100 properties. On paper, it looked like success. In reality, it was constant tenant issues, mounting repairs, and growing leverage. By 2008, he was $1.3 million in debt and ultimately lost more than 55 properties to foreclosure. That experience forced a hard reset and led him to abandon traditional rentals in favor of what he later named the Slow Flip model: selling low-cost homes on terms and holding the paper. Since then, Scott has completed hundreds of slow flips, building long-term cash flow without tenants, repairs, or property management, and now focuses on helping other investors escape the operational grind of real estate. To learn more or buy the book, go to https://www.slowflip.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. Get Your FREE Copy Of 'The Private Money Guide' and 'Mapping Out The Millionaire Mystery'. Keep up with us every week on our FREE Live webinars for more conversations like this, and as a BONUS, get our newest mini-ebook instantly upon signing up! https://moneyschoolrei.com/wednesday-webinar (digital download). Dive into money, mindset, and motivation videos on my YouTube Channel, and be sure to subscribe so you can be notified of our weekly LIVE streams. Find out about our next weekend workshop, and see what others are saying: https://www.moneyschooltraining.com/registration.

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: in the urge to hold money tighter, in the guilt that makes generosity feel risky, and in investment choices that look diversified but are actually fragmented and scattered. For more than 30 years, financial advisor Shannon Ryan has seen this up close. She's worked with founders, professionals, and ultra-wealthy families who have everything they once wanted, yet still feel overwhelmed, afraid, or ashamed of how they handle money. Not because they lack discipline or intelligence, but because their emotional relationship with money never evolved as quickly as their wealth did. In this conversation, Shannon and I explore the hidden side of wealth: why financial milestones don't automatically create peace, and what it actually takes to feel free when the numbers say you should already be there. About the Guest Shannon Ryan is a Certified Financial Planner CFP®, behavioral finance advocate, speaker, and the author of the upcoming book Your Money Has Feelings. With over 30 years of experience guiding individuals and families, Shannon blends clear financial knowledge with a heart-centered approach to help people heal their money stories, transform their financial behavior, and build lasting confidence. She's been featured on Good Morning America, CNBC, and TEDx, and is known for making personal finance feel relatable, empowering, and deeply human. To work with Shannon, visit https://shannon-ryan.com/. Buy her book, "Money Has Feelings," on Amazon. 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.

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 spend, you start over. The numbers change, but the pattern doesn't. That's where infinite banking enters the conversation, not as a magic button, but as a system that gives truckers a way to make their money work even when they're not on the road. But here's the part most people miss: Infinite banking only works if you do. Because there's a trap almost everyone falls into. You pay off your debts, you free up all that cash flow… and then you let it drift back into a traditional bank account, where it gets spent, swallowed, or forgotten. And this same pattern shows up in another overlooked area of trucking: health. The lifestyle is notoriously hard on the body: long hours sitting, fast food at every stop, poor sleep, and constant stress. It's easy to wake up one day and realize your finances aren't the only thing stuck in a loop you never intended to be in. In this episode, I'm joined by Dexter Holiday, a longtime trucker who set out to rewrite both his financial and health trajectory. We explore what it looks like to step out of the financial and health cycles of trucking. We unpack the strategy, the mistakes, the course corrections, and the mindset shifts required to make it all work in real life. Things You'll Learn In This Episode Infinite Banking only works if you doMost people succeed in paying off debt but fail to recapture the payments and lose thousands in the process. How do you start thinking and acting like the bank? Debt freedom isn't the goal; debt management is Dexter cleared his debts, then unknowingly recreated them because the old habits were still in place. How do you stop yourself from sliding back into the same financial patterns you're trying to escape? Discipline creates wealth and health The same mindset that made Dexter financially stable helped him reverse diabetes, transform his energy, and rebuild his body. Why do money problems and health problems stem from the same root behaviors, and how do you change them? Fasting can undo what the road does to your body Trucking beats up your health, long hours sitting, constant snacking, and limited food options. How did fasting give Dexter's body the break it needed to repair itself and reverse the damage? About the Guest Dexter Holiday is a longtime trucker who has spent years navigating the financial and physical demands of life on the road. After realizing the trucking industry offers income but not freedom, he began searching for a way to break the cycle of "earn, spend, reset." His journey through infinite banking, financial mistakes, course corrections, and eventually dramatic improvements in his health has made him a powerful example of what's possible when you commit to discipline, learning, and change. To learn more about the products that helped Dexter change his health, visit https://ufeelgreat.com/c/AKL589. 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.