Why Investors Fail After the Flip (and How to Never Be One of Them) w/ Aaron Chapman
Release Date: 05/08/2025
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Money School Podcast
From the outside, doctors and dentists look like they’ve got it all: good money, respected careers, the kind of lifestyle most people want. But what almost no one talks about is how fragile that life really is. One accident, one injury, and the very hands that their entire career depends on can suddenly stop producing income. That was Dr. Jeff Anzalone’s reality after a skiing accident nearly ended his ability to practice dentistry. It forced him to realize: as much as medicine can be rewarding, it’s still trading time for money, and it can all disappear in an instant. The solution...
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Money School Podcast
Most people who buy life insurance never read the fine print. They’re promised “stock market–like returns without the risk,” a retirement account that doubles as a tax-free loan machine, and peace of mind for their families. On paper? It looks like the perfect product. But what happens when the math doesn’t add up, the illustrations don’t match reality, and families find out, years later, that the policy they’ve been funding is set to collapse? That’s the dark underbelly of the Indexed Universal Life (IUL) industry. And it’s exactly what my guest, Jonathan, aka the IUL...
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Money School Podcast
Most people who buy life insurance never read the fine print. They’re promised “stock market–like returns without the risk,” a retirement account that doubles as a tax-free loan machine, and peace of mind for their families. On paper? It looks like the perfect product. But what happens when the math doesn’t add up, the illustrations don’t match reality, and families find out, years later, that the policy they’ve been funding is set to collapse? That’s the dark underbelly of the Indexed Universal Life (IUL) industry. And it’s exactly what my guest, Jonathan, aka the IUL...
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Money School Podcast
Most business owners only call the bank when they’re in trouble. Cash is tight, deals are falling apart, stress is mounting. By then? It’s too late. The banks shut the doors and wave at you from behind the glass. That’s the obvious mistake. The less obvious one? Not realizing the best time to secure financing is when you don’t need it. That’s when banks give you more, on better terms, and when private lenders are willing to play ball. That’s the theme of my conversation with George Otel, founder of U.S. Business Funding. He’s closed 400+ deals, from SBA loans to $50M...
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Money School Podcast
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Money School Podcast
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Money School Podcast
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Why So Many Real Estate Investors Are Burnt Out w/ Ashley Kehr
Money School Podcast
Feeling burnt out? You’re not the only investor hitting that wall. Long hours, back-to-back deals, tenants, contractors, financing, and the never-ending pressure to grow. You got into real estate for time freedom and financial independence, but somewhere along the way, it started to feel like just another grind. Here’s the truth most investors won’t say out loud: Burnout isn’t a rite of passage, it’s a red flag. And ignoring it can cost you more than just momentum; it can eat away at your health, relationships, and your reason for investing in the first place. But what if there’s...
info_outlineYou found the deal. You found the lender. You even closed with hard money. Now what?
That’s the question too many investors forget to ask—until it’s too late.
In today’s market, with traditional financing tightening up and banks saying “no” more often, smart investors know that real money is made after the flip. When you’ve got a reliable exit strategy.
But here's the problem: too many investors get stuck in the deal because they never thought through how they were going to get out.
They scramble for financing after the fact, only to find the terms are terrible, if they can get approved at all.
That’s when the clock starts ticking, interest racks up, and the whole investment starts bleeding cash.
So what’s the play when the banks won’t play ball?
Enter Aaron Chapman, a seasoned lender who’s made it his mission to get the unbankable deals bankable.
For over 20 years, Aaron has helped investors navigate the toughest markets. Now, he's teamed up with Private Money Club to help investors set themselves up for long-term wealth, not just short-term flips.
In this episode, Aaron shares exactly what you need to do to make your investment deals irresistible, not just to private lenders, but to banks, too.
Things You’ll Learn In This Episode
-The “Exit Strategy Mistake” That’s Killing Deals
Most investors think about finding the right property, not the right financing. What should really come first?
-What Banks Aren’t Telling You (But Aaron Will)
Think the DSCR loan is your answer? It might be, but not the way most lenders do it. What do smart investors look for in today's lending climate?
-Why You Shouldn’t Pay Off That 30-Year Mortgage Early
Could stretching out your mortgage be the best move you can make?
Guest Bio
Aaron is the pre-eminent financing guy for property investors. He's a well-known educator in the industry, and has lots of tools in his financing toolbag. A veteran of the finance industry since 1997, Aaron is a battle-worn partner every real estate entrepreneur needs to walk through the tough parts of building a business. As America’s #1 Retail Mortgage Lender, his clients include people purchasing their first home, building their dream home, or investing in multiple properties for long-term cash flow. He is an expert in the complicated, leading to recognition by Scotsman Guide as one of the nation’s Top Originators. In addition to his mortgage career, Aaron is a published author with books and dozens of magazine articles. Visit https://aaronchapman.com/ to learn more and work with Aaron.
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 currently 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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