What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
Release Date: 12/04/2025
Making Millions, Losing It, and Learning How to Keep It w/ Lawrence Dunning
Money School Elite
Most people think the hard part is making money. But Lawrence Dunning’s story shows that making money, keeping money, and using money well are three very different things. By 30, Lawrence had built a multi-million-dollar net worth on the trading floor in Chicago. Then he stepped away to pursue a dream that had a much smaller window: becoming a professional MMA fighter. When he came back, the trading business model that had made him wealthy had changed, and the income stream he once relied on was gone. In this episode of Money School Elite, I sit down with Lawrence to talk about what he...
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The Business Exit Strategy Most Founders Start Too Late w/ Mike Bennett
Money School Elite
Most business owners think their exit value will come down to EBITDA and an industry multiple. But buyers are not only evaluating what the company earns; they are deciding how much risk they would inherit. That risk can show up in customer concentration, weak financial reporting, founder dependence, an incomplete leadership team, or a business that has not been prepared to operate without its owner. In this episode of Money School Elite, I sit down with Mike Bennett, founder of Crewe Capital, to examine what sophisticated buyers actually look for and why strong exits often take...
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High Income, No Tax Advantage: The Wealth Problem Pilots and High Earners Need to Solve w/ Ryan Gibson
Money School Elite
Most high-income W-2 earners eventually run into the same problem. Their income gets better, but their structure does not. Airline pilots are one of the clearest examples. They can earn exceptional money, receive strong retirement contributions, and build what looks like a very successful financial life on paper. But as the income grows, so does the constraint: almost all of it is active, highly taxable, and tied to a system that gives them very few levers to pull. And pilots are not the only ones facing this. Doctors, executives, engineers, senior tech employees, corporate leaders, and...
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How to Beat Big Capital at the Bitcoin Mining Game w/ Beau Turner
Money School Elite
Most investors assume there are only two practical ways to approach Bitcoin: buy it directly and accept the volatility, or avoid it because it does not fit the framework that built their wealth. But Bitcoin mining introduces a different conversation. For most people, mining sounds too technical, too operationally complex, or too institutional to be a serious investment strategy. Servers, power, cooling, maintenance, custody, and infrastructure all make it feel out of reach for anyone who does not want to become a full-time operator. Beau Turner has built a model that changes that. Through...
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Outgrowing Your Accountant: The Tax Problem Business Owners Miss w/ Boris Musheyev
Money School Elite
Most business owners do not realize they have outgrown their accountant until the tax bill becomes impossible to ignore. The person who helped you when the business was small may have been perfectly fine at that stage. But as revenue, profit, assets, investments, and complexity grow, tax preparation is no longer enough. At a certain point, the business does not just need someone to file the return. It needs real tax planning. In this episode of Money School Elite, I sit down with Boris Musheyev, a tax strategist who works with seven-figure and multi-seven-figure business owners, to talk about...
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Wholesaling Isn’t Just A Beginner Real Estate Strategy w/ Chris Logan
Money School Elite
Most investors think wholesaling is just the entry-level side of real estate. At the strategic level, the better conversation is about deal flow. Because in a market where seller motivation is rising, buyers are more selective, and many casual wholesalers have left the business, the opportunity is different from what it was a few years ago. The edge is not simply finding properties. It is knowing how to identify distress, control the contract, understand buyer demand, and move before the rest of the market sees the opportunity. That is where wholesaling becomes more interesting than most...
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The Difference Between Watching Stocks and Owning Businesses
Money School Elite
In today’s market, investors with real capital are facing a difficult problem. They do not want to be reckless. Equities feel expensive, private credit has shown signs of stress, rates remain elevated, and the usual recession signals have been flashing for longer than many expected. But they also do not want to hide in safety so long that they give up years of compounding. That is where the conversation around risk has to get more precise. The question is not simply whether to be in or out of the market. It is how to structure capital so you can stay rational, preserve optionality, and...
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The Tax Credit Hidden Inside Your Business Improvements w/ Derick Van Ness
Money School Elite
For many business owners, one of the biggest missed wealth opportunities may already be sitting inside the business. Technology upgrades, software implementation, equipment, and operational improvements. These are the kinds of investments owners are already making to grow, modernize, and stay competitive. But in many cases, they may not just be expenses or deductions. They may create R&D tax credits. A deduction lowers taxable income. A credit can reduce taxes dollar for dollar. For an owner with meaningful income, that is not a small accounting detail. It is capital that can stay inside...
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The Private Real Estate Reset Wealthy Investors Need to Understand w/ Michael Pouliot
Money School Elite
Most investors think real estate performance comes down to the asset. At the high-net-worth level, the more important conversation is often about control. Because a deal is not just a building, a market, or a projected return. It is an operating system. Who manages the property? Who controls leasing, maintenance, marketing, resident communication, and costs at the asset level? Who can make decisions quickly when the market tightens, and the assumptions in the original deck no longer hold? That is where real estate investing starts to look very different. A lot of investors were comfortable...
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The Private Equity Play Hidden Inside Franchising w/ Scott Jones
Money School Elite
Most people think franchising is about income replacement. At the high-net-worth level, the real conversation is about enterprise value. Because the operators who approach franchising seriously are not just trying to buy themselves a business. They are thinking about cash flow, unit economics, operational infrastructure, EBITDA growth, private equity demand, and whether the business can eventually become attractive to a larger buyer. And once you understand that, the way you evaluate franchising starts to change. Most franchise buyers don’t miss the opportunity because they fail to...
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.