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What most M&A pros miss about middle market deals

INSIGHT 5 min read

WRITTEN BY

Kurt Estes

People like to assume M&A is all numbers, models and late nights hunched over spreadsheets. They picture a room full of analysts fueled by caffeine and ambition, calculating valuations and sharpening deal terms. Sure, there is plenty of that. But the longer you work in this field, the more obvious it becomes that the real engine behind a successful transaction is not the spreadsheet. It’s the human being on the other side of the table.

My own path into M&A was anything but typical. I collected engineering degrees, earned an MBA and then wandered through roles in technology licensing, venture capital, strategy, consulting, corporate innovation and a few other stops along the way. Every so often, I speak with students or early career professionals who want to break into investment banking. They study my resume like it is a treasure map and ask how I maneuvered my way into the industry. It’s a fun story but not the one that matters most here.

What they really want to know is what background best prepares someone for a career in M&A. Most people expect me to say finance. And yes, if you want to build a solid foundation in valuation and capital markets, a finance degree helps. So does the rigorous training programs offered at large investment banks. But in the middle market, where founders are often the sellers and emotions run high, there is another skill that quietly shapes the entire process. It is the ability to understand people.

Human psychology might not be listed in the job description, but it deeply influences how every deal unfolds.

Middle market companies are often still owned by their original founders. These are people who didn’t just invest their time and capital. They poured their identity into their business. Many have spent twenty years or more building something from the ground up. When you dedicate that much of your life to any single endeavor, it becomes part of who you are. It’s not a stretch to say the attachment can feel familial. I have heard founders describe their companies in the same tone they use when talking about their children.

Think about a simple social situation. You meet someone at a party and one of the first questions that comes up is, “What you do for work?” Most of us define ourselves by our profession to some extent. Now imagine your profession is a business you personally built, nurtured, protected and grew for two decades. That is identity on a whole different level.

So when a founder finally decides to sell, often as the only realistic way to retire, that decision is rarely clinical. Even if the financial logic is sound, the emotional turbulence can be intense. Doubt creeps in. Anxiety shows up at inconvenient times. One day the choice feels perfect. The next day it feels like betrayal. These swings are normal, not a sign of weakness. They are simply the emotional costs of letting go.

This is where psychological awareness becomes one of the most underrated tools in an advisor’s arsenal. When you recognize how deeply personal this transition is, you can guide founders through the process with empathy, clarity and confidence. You can help them make decisions rooted in what they truly value rather than in fear or sentimentality. You can also help them see their impact with fresh perspective.

One of the most grounding reminders I share with founders is this: If your business has one hundred employees, your years of risk-taking, sacrifice and relentless effort support one hundred families. In reality, the number is far higher when you consider turnover and growth over time. A founder’s legacy is not just the revenue they generated. It is the livelihoods they protected. It’s the careers they shaped. It’s the community they supported.

That legacy matters deeply to many sellers. Some care more about finding a buyer who will honor their employees, clients and reputation than they care about squeezing out the last dollar in the purchase price. When you understand those priorities, you can structure a transaction that meets their emotional goals as well as their financial goals. That is what success looks like in the middle market.

Which brings us back to the question students keep asking: What background best prepares someone for M&A? Finance is valuable. Operational experience helps. But if you want to thrive in the middle market, learn how people think. Learn what motivates them. Learn how identity shapes decisions. Deals are built on logic but they close on trust.

If you are considering selling your business or want guidance navigating the human side of the transaction, contact us. We can help you move through the process with clarity, confidence and the support you need to achieve the outcome you want.

Author

Kurt has over 25 years of transaction experience that includes advising on sales and acquisitions as well as investing in or creating businesses around innovative technologies. He has conducted or managed dozens of transactions covering all stages of a company’s life, from helping to acquire seed investments through facilitation of liquidity events. Kurt has negotiated a wide variety of deals, including asset buyouts, recapitalizations, spin-outs, strategic partnerships, licensing agreements, and various debt structures.