The Origin Stories Behind Great Dealmakers

In this special best of episode of the DealQuest Podcast, I'm excited to share something that reveals the human side of dealmaking. Over the years, I've asked every guest the same second question: "What was the first deal of any type that you were involved in?" The answers always fascinate me because they show how dealmaking instincts develop early, often in unexpected ways.

Some guests share true deal stories involving negotiations, partnerships, or business transactions. Others recall their first sales experience or entrepreneurial venture. The beauty of this question isn't just hearing about deals - it's understanding the early experiences that shaped these successful business leaders. Whether it's a childhood lemonade stand that taught negotiation or a career-defining transaction that opened doors, these origin stories provide context for the expertise they've developed over decades.

The Personal Deal That Changed Everything

Thomas Samuelson from episode 219 shared how his first deal wasn't with a client or business partner - it was with his employer. "I got out of school and I went into the Maryland training program in finance, and I was stationed down in Philadelphia area. And I didn't like Philadelphia. I cut a deal and manufactured a deal to get myself in New York."

What makes this story powerful is the negotiation mindset. Thomas didn't just ask for a transfer; he "manufactured a deal" to make it happen. This was particularly challenging because, as he noted, "they didn't do things like that back then." The ability to create win-win solutions where none existed before became a defining characteristic of his later success in dealmaking.

The lesson here applies to any professional situation: sometimes the most important deals are the ones you make for yourself, especially early in your career.

Learning Deal Fundamentals Through Adversity

Anthony Nitkos from episode 253 learned about dealmaking under the most challenging circumstances. When his father passed away, Anthony was suddenly thrown into handling a buy-sell agreement at just 26 years old. "My father had put me in charge of his estate when he passed, and I had to all of a sudden come up to speed with, hey, what's a buy sell arrangement? What's an insurance payout? How do you go about valuing a company?

This baptism by fire taught him essential deal concepts that many business owners avoid thinking about until it's too late. Anthony's experience highlights how critical it is to understand these structures before you need them. Having clear buy-sell agreements, proper valuations, and succession plans isn't just good business practice - it protects families during their most vulnerable moments.

Early Entrepreneurial Instincts

The childhood stories reveal natural business instincts that later became sophisticated deal skills. Kurt Davis from episode 241 kept it simple: walking across the street and asking his neighbor if they wanted their lawn cut. When they offered him $10 instead of his suggested $5, he learned his first lesson about not undervaluing your services.

Sunny Vanderbeck from episode 293 took this approach much further in second or third grade. He negotiated a lawn care contract with a family, then subcontracted the actual work to other neighborhood kids, keeping $3 profit. "I paid one kid five bucks to mow the lawn and another kid two bucks to weed eat the lawn. And I had three dollars left over. And I was like, hey, this is kind of cool."

What struck me about Sunny's story isn't just the entrepreneurial thinking. The natural understanding of leveraging resources and creating systems that drive successful business growth throughout a career really came through.

When Parents Become Regulators

Brett Martin from episode 268 learned about both business operations and ethics through his seashell cleaning business. He and his sister would buy dirty seashells from fishermen for $2 per bushel, clean them with bleach, and sell them individually for $2 each. Quite an impressive ROI.

The business ran smoothly until his parents discovered the pay disparity: Brett was paying his sister 50 cents an hour while keeping most of the profits. His parents quickly "regulated" the business, requiring that "profits shall be spread equally." As Brett put it, "I think that was a good ethical lesson to learn earlier."

This story touches on something every growing business faces: how to structure compensation fairly while maintaining profitability and growth incentives.

From Sales Training to Deal Development

Elliot Kaplan from episode 274 received formal sales training from his father in third or fourth grade. His dad, who was in the ink and pen business, gave him 100 green markers to sell at school for a nickel each. When Elliot successfully sold them all (despite getting "beaten up a little bit for some money"), his father saw the potential.

"He said if you could do this and sell this, which is a nickel, imagine what you could do to something really big. So that means you have the gift of gab," Elliot recalled. His father recognized that persuasion and negotiation skills could scale to much larger opportunities.

The confidence to approach prospects, handle objections, and close transactions forms the backbone of successful deal execution later in business.

Building Systems from Simple Concepts

Scott Bushkey from episode 285 discovered his dealmaking aptitude through door-to-door Cutco cutlery sales in college. What started as a way to pay speeding tickets turned into a statewide competition win in just two and a half days. The recognition that "people do this for a living" opened his eyes to the potential of systematic business development.

Kevin Bopp from episode 309 learned deal fundamentals through car flipping between ages 15 and 19. By connecting with a mechanic who had a dealer's license, Kevin could access wholesale auto auctions, buy cars at wholesale prices, and sell them to retail buyers. "I probably had 14 or 15 different cars. I never kept track of it. I would literally trade out multiple year and I would just keep stacking, you know, flipping car."

These experiences taught the fundamental principle that drives successful deals: buying at wholesale and selling at retail, with proper systems to identify opportunities and manage transactions.

Professional Deal Foundations

The professional stories show how formal business experience builds on these early instincts. Scott Weavel from episode 313 cut his teeth on public company M&A transactions as a practicing attorney. Dennis Stearns from episode 320 led the sale of a chemical company to a German buyer, learning how different cultures approach negotiations.

Dennis emphasized the importance of building the right team: "The thing that I love about the team concept is you get all the right people on the team and you will minimize the amount of fumbles that you have in the process." This collaborative approach to complex deals fits perfectly with the relationship-focused negotiation style that characterizes successful dealmaking.

The Common Thread

What connects all these stories is the recognition that dealmaking goes far beyond transactions. Understanding people, creating value, and building systems that work - whether it's a childhood lemonade stand or a multi-million dollar acquisition, the fundamental skills remain the same: identifying opportunities, understanding what others value, and structuring agreements that benefit everyone involved.

These origin stories remind us that great dealmakers aren't born with some mysterious talent. They develop their skills through experience, learning from both successes and failures, and maintaining curiosity about what makes people and businesses tick.

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FOR MORE ON COREY KUPFER
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Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.


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