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Episode 270 – The Entrepreneur’s Retirement Dilemma: When Your Identity Is Your Business With Gregory Kovsky

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What happens when a business owner’s identity becomes completely tied to the company they’ve built? Selling the business isn’t just a financial transaction — it’s an emotional crossroads.

In this episode of The Agent of Wealth Podcast, John Williams is joined by Gregory Kovsky, President of IBA, a firm specializing in the confidential sale of privately held companies. Gregory shares what he’s learned from decades of guiding owners through one of the most impactful transitions of their lives: exiting the business they poured themselves into.

In this episode, you will learn:

  • How to determine the true value of a business beyond the balance sheet.
  • Why timing the sale is more about personal readiness than market forecasts.
  • The emotional challenges that often arise during exit planning — and how to prepare for them.
  • Key steps to ensure a smooth, confidential, and fair sale process.
  • And more!

Tune in for a thoughtful discussion on preserving legacy, maximizing financial outcomes, and planning for what comes after the business is sold.

Resources:

IBAINC.com | 425-454-3052 | Bautis Financial: 8 Hillside Ave, Suite LL1 Montclair, New Jersey 07042 (862) 205-5000 | Schedule an Introductory Call

​​Disclosure: The transcript below has been edited for clarity and content. It is not a direct transcription of the full episode, which can be listened to above.

Welcome back to The Agent of Wealth Podcast. This is your co-host, John Williams. Today, I’m joined by Gregory Kovsky – President and CEO of International Business Associates, the Pacific Northwest’s oldest and largest business brokerage firm, founded in 1975. 

With over 30 years of experience in mergers and acquisitions, Gregory has personally facilitated more than 300 transactions for privately held and family-owned businesses.

Beyond his transactional expertise, Gregory is also a published author, seminar speaker, and advocate for entrepreneurship – operating on a unique work-life balance philosophy that we’ll touch on later in the conversation.

Gregory, welcome to the show.

Thank you. It’s an honor to be here.

So, I’m really excited about this conversation. We have a lot of clients who are small business owners. There’s an aura in the marketplace around business ownership – and often the perception is more glamorous than the reality. But for many, the dream is to build, grow, and eventually sell the business. I’m really looking forward to diving into this. To get started, I’d love for the audience to learn a bit about you and your journey. What led you to the world of mergers and acquisitions, and ultimately to purchasing IBA in 2000?

Certainly. I’ll give you a thumbnail sketch. I grew up in the Pacific Northwest – I’m originally from Portland. Eventually I was tired of the rain and wanted to spread my wings, so I went to the University of Texas in Austin, where I studied business, focusing on investment finance and accounting. On my father’s encouragement, I pursued my childhood passion and spent four years as a college basketball coach and national recruiter.

After those four years, I decided to return to the Pacific Northwest and explore the next chapter. IBA had previously sold my father’s veterinary hospital and real estate. He had been impressed with them and introduced me to the founder of IBA, Bill Osofsky. The business intrigued me, so I joined the firm in 1994. Between 1994 and 2000, I emerged as one of the top salespeople in the company. I was selected to be Bill’s successor, and we reached an agreement for me to purchase the company.

At the time, we had an “old guard” of brokers, many approaching retirement or with kids in college. We operated somewhat similarly to a real estate firm, and Bill didn’t want their lives disrupted. Many had mentored me, and he knew I wouldn’t micromanage them. So I took over in 2000 and things went wonderfully — until the 2008–2009 Great Recession. When consumer spending stops and banks restrict lending, business acquisitions slow dramatically.

We went from 15 brokers down to six during that period, including myself. Many retired or pursued other professions. Only one broker from before the recession is still with us. But since then, we’ve steadily rebuilt. Today, we have 18 brokers facilitating transactions across 10 offices in the Pacific Northwest. We’re also commercial realtors, so we can represent both the business and the real estate — for example, selling a winery along with its vineyards and production facility. We handle everything from valuation through closing.

Excellent. Is your clientele niche today? You mentioned real estate — has your focus evolved? Are there specific industries you specialize in?

We represent businesses in roughly 20 industry sectors — manufacturing, technology, education, and more. Our approach is largely industry-agnostic, as long as it’s a solid business. We typically work with companies generating EBITDA between about $250,000 and $5 million. We apply a multiple of two to seven times earnings depending on industry, risk factors, and other valuation dynamics.

That’s a wide range. I’d like to step back to the seller experience. Many business owners tell us they don’t even know if their business is sellable. So, for a business owner who approaches you saying, “I’m thinking about retiring — I want to sell this business,” what does that first step look like?

My mother was a teacher, and I believe a good relationship begins with communication and education. So the first step is sitting down with the owner to understand why they want to sell and what they’ve built. Then we perform a valuation. Valuation serves two purposes: First, it allows the seller to sample our experience and service. Second, it provides clarity on estimated market value.

Valuation is a nuanced, subjective science. On one side, you have return on investment and historical financials. On the other, you have elements like brand reputation, staff, customer relationships, and systems. These are the qualitative factors — the “art” of valuation.

Before we went on the air, you mentioned you’re from Philadelphia. If someone wants a cheesesteak, there’s a spectrum of quality. Not all are equal. The same applies to businesses. If your child wanted to run one of those shops, which would you recommend? The one with better systems, location, staff, and reputation. That’s how we think about valuation — mitigating risk.

We also evaluate whether the business model is sound, whether the seller is trustworthy and collaborative, and whether their expectations are realistic. Ultimately, the fair market value is what a willing buyer and a willing seller agree to in the current market.

Speaking of buyers — how do you find them? Is there a network you tap into?

Yes. Creating a marketplace of qualified buyers is part of our representation. Frankly, there are more buyers than sellers today. Our clients are often doing well and enjoying running their businesses, so the urgency to sell isn’t always there. On the buyer side, we sell to public companies, private companies, private equity, family offices, and individuals.

There’s also a strong entrepreneurial ethos today — people want autonomy. But I caution aspiring entrepreneurs: do not enter undercapitalized. It’s one of the most common reasons businesses fail. As Elon Musk has said, building the prototype is easy — scaling is hard.

You mentioned the owner is often deeply involved in the business. What challenges arise during evaluation and preparation for sale when the owner is such a key part of the operation?

The first challenge is comfort with transparency. Many business owners haven’t even shared financial details with their family. Yet buyers will need to review financials, leases, equipment lists, customer concentration, and more. Another challenge is customer concentration. For instance, we’re currently selling a company that works with the U.S. Navy. If that relationship isn’t secure, that risk impacts valuation.

Emotion is another major factor. The business is often like a child. Beyond price, owners worry about employees — who may feel like extended family — and customers. No one wants to see service quality decline under new ownership.

There are also spouse dynamics and partnership dynamics. Sometimes one partner wants to reinvest in growth while another wants to retire. We often play the role of counselor along with broker, helping ensure that these issues are handled before negotiations begin.

That makes a lot of sense. Along those lines, the fit of the buyer must be important — in terms of personality, values, and culture — not just money.

Absolutely. We do business with people we know, like, and trust. We’re evaluating whether the buyer has relevant experience and whether they’re a cultural match. Employees may speak multiple languages, or there may be unique customer relationships. We want to ensure continuity.

Do you see patterns among business owners who struggle most with transitioning out of ownership?

Often it ties to identity. Some people define themselves through their business. If golf is enjoyable because you spend weekends discussing business challenges with friends, what happens when that’s gone? Business is the ultimate competitive sport — every day you put on your shoes and compete.

Just look at Sears — they were Amazon before Amazon. They had the distribution, catalog reach, and brand recognition, but they didn’t evolve with consumer behavior. Business requires constant adaptation.

I want to ask about owners who are the business — the key salesperson or operational leader. Can those businesses still be sold?

Yes — but we need to plan for transition. We identify key employees early and involve them late in the process, once financing and terms are in place. Then we control the narrative. The seller acknowledges the employee’s value, offers transition compensation, and introduces the buyer properly. Buyers will want to retain strong employees. Transparency and timing are key.

What are some common mistakes you see business owners make before selling?

The biggest one is being the hub of everything — not delegating. An owner should work on the business, not in it. That drives value. Also, avoid customer concentration. And build systems and processes — written operating procedures, sales manuals, and documented workflows.

As we wrap up, what advice do you have for aspiring entrepreneurs?

Expect failure — it’s part of the journey. Make sure you have relevant experience or strong mentors. If you’re a great salesperson, hire a strong finance leader. Ensure you have capital to grow, and grow at a sustainable pace.

And finally — what would you say to a business owner who isn’t sure whether their business is worth anything?

Seek knowledge. Talk to brokers. Not all brokerages are the same — our model is 100% performance-based, meaning clients don’t pay unless a transaction closes. And even businesses without many tangible assets — like a flooring showroom that only keeps samples — can be highly valuable if they have brand reputation, loyal customers, and steady profitability. We’ve sold many businesses like that.

That’s great to hear. Gregory, congratulations on your career and thank you for joining me today. Before we wrap, where can listeners learn more?

I’d direct people to our website: IBAINC.com. Visit our blog, which serves as a resource library for entrepreneurs. If you’d like to speak with me directly, call our corporate headquarters at 425-454-3052.

Great. We’ll link to that in the resources section of the show notes. Thanks again, Greg. And thank you to everyone who tuned into today’s episode. Don’t forget to follow The Agent of Wealth on the platform you listen from and leave us a review of the show. We are currently accepting new clients, if you’d like to schedule a 1-on-1 consultation with our advisors, please do so below.

Bautis Financial LLC is a registered investment advisor. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial advisor and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance. 


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