How to Beat the Insurance Companies at Their Own Game w/ Rob Haynie
Release Date: 08/07/2025
Wealthy People Upgrade Everything… Except This w/ Ted Ryce
Money School Podcast
As people make more money, they tend to get sharper about almost everything. They think long term, manage risk better, hire experts, invest wisely and optimize their businesses and portfolios. But when it comes to health, a lot of people are still running the same basic playbook everyone else is. Standard labs, five-minute appointments, and just waiting until something breaks. When you want to level up in every area of your life, the conversation shouldn’t be, “Am I sick right now?” It should be, “Where am I headed, and how early can I catch it?” The people who are strong,...
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“I Can’t Afford a Coach” Is Why You’re Stuck w/ Patrick Engasser
Money School 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...
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Putting Your Money in Buckets Is a Trap, Do This Instead w/ Joseph Kovacevic
Money School Podcast
Most people think financial freedom comes from earning more, saving harder, or finding the perfect investment. But the real trap isn’t income…it’s the way we’re taught to store and move money. We’re told to separate everything into neat little buckets: checking, savings, mortgage, credit cards, investments. And somehow, even when we’re “doing well,” the system still feels tight, slow, and exhausting. The traditional system is wildly inefficient by design. A 3–4% mortgage isn’t really 3–4% at all. It’s closer to 12–15% in simple interest once you account for...
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How to Stop Leaving Money Inside the Tax Code w/ Zach Newberry
Money School Podcast
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...
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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...
info_outlineHere’s the dirty secret in the term insurance industry: They win when you cancel. They win when your policy lapses. They win when you don’t understand what you really own.
Think about that for a second.
You’ve been sold on the idea that term insurance is the smart, affordable choice. But what no one tells you is this: it’s a ticking clock. If you outlive the term, you get nothing. All those years of paying in? Gone. Just like that.
Who wins? The insurance companies. Every. Single. Time. They count on you to drop it. They bank on you not knowing any better.
But what if you flipped the script? What if you could turn the tides and make term insurance work for YOU? What if you could unlock hidden value in your policy before it vanishes?
Because the truth is that you can. There are strategies the wealthy use to extract value from term policies that most people surrender without a second thought.
Rob Haynie, Managing Director at Life Insurance Settlements, Inc., joins me in this episode to expose the hidden greed within the insurance industry. We dive into how millions are misled when it comes to term life insurance. More importantly, we reveal how you can flip the script and use your policy to your advantage instead of getting taken for a ride.
Things You’ll Learn In This Episode
-Do more than just surrender
Most people with term insurance don’t realize there are alternatives to surrendering their policy. What if you could unlock hidden value from your term policy instead of just walking away from it?
-Slow economy surrender
In a slowing economy, many are surrendering their life insurance policies without realizing they may have better options. What are the other things you can do?
-Optimizing assets
Term insurance can be treated as an asset, just like your home, because you own it. If your term policy is an asset, are you making the most of its hidden value?
Guest Bio
Rob Haynie is the Managing Director and one of the founding partners of Life Insurance Settlements, Inc. (LIS), a leading life settlement brokerage based in Pompano Beach, Florida. With over 31 years of experience in the industry, Haynie has been instrumental in shaping the life settlement market, advocating for the value of life insurance as an asset class, and educating financial professionals and policyholders about settlement options. Throughout his career, Haynie has been directly involved in negotiating and settling thousands of life insurance policies, earning a reputation as one of the most influential figures in the field. He has served multiple terms on the Board of Directors of the Life Insurance Settlement Association (LISA) and has been a charter member of its Public Policy Committee, which focuses on regulatory and legislative activities within the industry. Haynie is a frequent speaker at industry events and has co-hosted the podcast Unlocking the Hidden Value of Your Life Insurance, where he discusses the benefits and intricacies of life settlements.
Call Rob on 954-599-4433
Email Rob rob@lisettlements.com
Find Rob on LinkedIn @Rob Haynie
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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