What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky
Release Date: 12/04/2025
The Tax Strategy Making Family Offices Rethink Bitcoin w/ Eric Runge
Money School Elite
Most investors think Bitcoin is about price. At the high-net-worth level, a far more important conversation is happening around taxes. Because Bitcoin isn’t treated like a stock or a business. It’s treated as property. And that classification opens up strategies around taxation and capital movement that simply don’t exist in traditional asset classes. And once you understand that, the way you evaluate Bitcoin starts to change. Most high-net-worth investors don’t dismiss Bitcoin because they don’t understand it. They dismiss it because, from where they sit, it doesn’t meet the...
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Real Wealth Is Built Before the IPO, But You Can’t Access It w/ Mona DeFrawi
Money School Elite
Most people don’t realize that a large portion of real wealth is created before companies ever reach the public markets. In private companies, early-stage investments, and entrepreneurial ventures, growth happens the fastest. For a long time, that part of the market has been largely inaccessible to retail investors, reserved instead for institutions and high-net-worth individuals. And that has played a significant role in the growing gap in wealth. In this episode of Money School Elite, I sit down with Mona DeFrawi to unpack how this system actually works and what’s starting to change....
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The Fastest Way to Grow Your Business (It’s Not Strategy) w/ Greg McDaniel
Money School Elite
Most people think success comes from strategy…better marketing, better positioning, better timing. But what if that’s not the lever at all? What if the thing that actually drives growth isn’t what you take, but what you give, freely, consistently, and without any immediate expectation of return? Because when you really look at how businesses grow, how opportunities compound, and how networks form, the pattern isn’t subtle. The people who seem to “get ahead” aren’t always the smartest or the most tactical. They’re the ones who become connectors, who create value before...
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Real Estate Investing Isn’t Complicated, You’re Just Doing It Wrong w/ Joel Miller
Money School Elite
Most people don’t associate residential real estate investing with enjoyment. Between tenant issues, maintaining properties, and financing problems, it can really be a headache. But the problem isn’t the asset class; it’s how you approach it. Because real estate, when done right, is actually one of the most forgiving businesses you can be in. What separates the people who enjoy real estate from the ones who burn out isn’t intelligence or even experience. It’s getting around the right people and getting the right education. What kind of information should you be consuming? How...
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Smart Money Is Leaving Cash Behind, Here’s Where It’s Going Instead w/ Ben Reinburg
Money School Elite
Most investors believe that holding cash during uncertain markets is the safest move. If you stay liquid, wait for clarity, and avoid risk, you’ll be in a better position when opportunities come… or at least that’s the thinking. But what many high-income earners and investors don’t realize is that cash sitting idle isn’t neutral; it’s losing ground. Between inflation, taxes, and missed opportunities, capital that isn’t deployed is quietly working against you. And while many investors are pulling back, the most sophisticated capital, family offices, institutions, and sovereign...
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What’s Really Happening In Real Estate Lending Right Now? w/ Jonathan Yoo
Money School Elite
Many real estate investors believe success comes down to one thing: access to capital. If you can borrow money easily, scale quickly, and leverage aggressively, the thinking goes that your portfolio will grow faster. But what a lot of investors are learning right now is that capital alone doesn’t create successful deals. Structure does. In today’s lending environment, small mistakes in leverage, underwriting, or financing strategy can turn what looked like a solid deal into a long-term problem. And many investors don’t realize where those risks actually show up until after the...
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The End of Traditional Financial Advice? w/ Stefan Astheimer
Money School Elite
For a long time, truly personalized investment advice has been something only the ultra-wealthy could access. If you have tens of millions of dollars, you can hire advisors who don’t just sell you products. They build strategies around your entire financial life. But everyone else gets standardized portfolios and is told to keep contributing to their retirement accounts and stay the course. That’s starting to change. A new approach to financial advice is emerging, one built around a fee-for-service strategy instead of product sales. Instead of paying someone based on how much money they...
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What Banks Actually Look For Before Funding a Business w/ Sebastien Boyer
Money School Elite
Starting a business is often framed as a simple equation: have a good idea, take it to the bank, and secure the funding. But the reality is very different. Most business owners aren’t rejected because their idea is bad. They’re rejected because they approached the capital the wrong way. So many deals fail before they ever reach underwriting, and it’s not because of the opportunity. It’s preparation, structure, and understanding how lenders evaluate risk. Banks aren’t investors looking for the next big idea. They operate under strict guidelines, regulatory frameworks, and underwriting...
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The Financial Reality of Pro Snowboarding and How to Escape It w/ Stevie Bell
Money School Elite
Every athlete knows the music will eventually stop. Whether you walk away on your terms, are forced out by injury, or have a contract that doesn’t get renewed, your career will inevitably end. In leagues like the NFL, NBA, or MLB, that ending can still leave you financially set. You might walk away with generational money. In action sports, that’s rarely the case. A pro snowboarder can start earning real money in their teens. They can travel the world, land major sponsors, build a name, and live what looks like a dream career. But very few retire with enough money to last a lifetime. The...
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The Real Reason AI Valuations Are So High w/ Daniel Nikic
Money School Elite
In today’s market, AI valuations are expanding faster than fundamentals can justify. Companies with minimal free cash flow are being priced as if dominance is already secured. Capital continues to circulate between venture portfolios, strategic partners, and ecosystem incumbents, reinforcing growth narratives that assume liquidity remains abundant. But markets don’t reward narratives forever. When growth slows or capital tightens, the question shifts from projected upside to structural durability. Does the business generate real cash? Does it control proprietary data that compounds...
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.