What Most Entrepreneurs Get Wrong About Selling Their Business w/ Gregory Kovsky

When 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.