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.

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 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.

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 do
Most 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.

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, choosing the wrong advisors, or stepping into negotiations with a fantasy number another broker promised them to win the listing.

And the cost of that mistake? Years lost, deals collapsing, and owners discovering too late that they should have fixed their accounting, diversified their customer base, or tightened operations years before approaching the market.

And underneath all of it is an even deeper truth: exits aren't just financial events; they're emotional ones. If you don't know what your life looks like after the wire hits, you're at risk of waking up with more money than you've ever had… and less purpose than you've ever felt.

In this episode, I'm joined by Gregory Kovsky, president of IBA, one of the oldest and largest business brokerage firms in the Pacific Northwest. We dig into why the market is hotter than ever, how valuation actually works, the unique pitfalls sellers don't see coming, and why the real exit planning starts long before you think you're ready.

Guest Bio

Gregory Kovsky is the President and CEO of IBA (International Business Associates), the Pacific Northwest's oldest and largest business brokerage firm. Gregory has successfully negotiated the purchase and sale of over 300 privately held companies and family businesses in Washington, Oregon, Alaska, California, North Carolina, and Massachusetts since joining IBA as a mergers and acquisitions intermediary in 1994. He has also built a seven-figure, self-managing business across ten locations. He has successfully facilitated transactions involving manufacturing and distribution companies, industrial, marine, and automotive businesses, technology and software companies, and service, education, and retail businesses. A commercial real estate professional for over 30 years, Gregory commonly provides his clients with comprehensive representation in selling a business and the associated real estate. To learn more, visit https://ibainc.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.

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 returns. Jeff flips that equation. He focuses on building a life. He invests based on clarity, intention, and a long-term vision of what he wants his days to look like. Once you have that vision, the decisions become simple. You stop chasing the market and checking performance and start building something inevitable.

In this episode, I sit down with dentist, entrepreneur, and long-term investor, Dr. Jeff Seibert. We unpack how he creates wealth by ignoring the noise, lowering his cost of capital, buying assets that grow while he sleeps, and designing his portfolio around the life he actually wants.

Guest Bio

Dr. Jeff Seibert is a successful dentist and serial entrepreneur known for building highly profitable, well-run practices and using them as engines to fund private investments. What sets him apart is his refreshingly unique philosophy: he doesn't chase quick returns or market noise. He builds businesses and buys assets that compound quietly for decades, giving him freedom, control and long-term wealth without stress or speculation.

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.