What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
Release Date: 12/04/2025
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_outlineWhen 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.