The Humans in Dealmaking with Jeff Evenson

acquisitions generational wealth human connection interpersonal skills leadership Nov 01, 2023
The Humans in Dealmaking with Jeff Evenson

From the halls of West Point in 1990 to the bustling floors of stock trading, Jeff Evenson's journey through the corporate maze has been nothing short of remarkable. With an MBA from Washington University in St. Louis under his belt, Jeff navigated the world of stocks at a brokerage firm, managed diverse portfolios, oversaw pension funds, and played a key role in facilitating acquisitions for a prominent Fortune 50 company.

But it's not just his corporate pursuits that set him apart. Jeff's true passion lies in business ownership—a path he's intimately familiar with, having owned, run, and successfully exited businesses ranging from hair salons to aerospace manufacturers and even smoothie shops. Now, wearing the hat of an acquisition and acceleration coach, he is on a mission to guide others in building generational wealth through the intricacies of business acquisition and ownership.

Jeff Evenson's journey from West Point to business ownership offers invaluable lessons for entrepreneurs and business leaders. His experiences underscore the significance of anticipation, the art of negotiation, and the importance of clear communication.



While financial considerations are undoubtedly critical when making deals, the human element remains pivotal in sealing the deal. In the intricate dance of buying, selling, or starting a business, both the head.

Building a relationship is pivotal to a successful deal. Beyond financial considerations, many sellers care deeply about the legacy of their business and are unlikely to sell to someone they feel won't respect or continue that legacy. Building trust and rapport can be just as crucial as getting the numbers right.



Jeff advises against charging into meetings with sellers, focusing solely on financial specifics. Instead, he suggests fostering genuine conversations, letting sellers narrate their journey, their motivations, and their concerns about the future of the business post-sale. He emphasizes the importance of understanding a seller's emotional ties to the business, whether it's the legacy they've built or the relationships they've forged with employees over the years.



Jeff, with his extensive experience in business operations and hiring practices, is a firm believer in the power of collisions. A quote from our interview that sticks out to me is, “Collisions are the catalyst for greatness.” The idea is simple yet profound: When two people or entities with complementary skills and visions come together, the potential for greatness multiplies exponentially.



In a tight labor market, acquiring businesses can also be a strategy to onboard talent. Instead of recruiting individuals, companies can buy out entire teams or firms, ensuring they get seasoned professionals who are already synergized. While this approach has its advantages, however, integrating cultures and ensuring the acquired talent feels valued and comfortable are essential to the acquisition's success.

For those interested in leveraging Jeff's expertise, he is approachable and encourages direct contact. He's available on LinkedIn and has two businesses: His coaching business at and his personal acquisition venture at

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For my full discussion with Jeff Evenson, and more on this topic and others discussed not featured in this blog post:
Listen to the Full DealQuest Podcast Episode Here

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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.
If you want to start getting yourself deal-ready, check out the DealQuest Podcast with Corey Kupfer each week. Featuring industry leaders and newcomers as guests alike, the DealQuest podcast has something for everyone.

Corey Kupfer is an expert strategist, deal-maker, and business consultant with more than 35 years of professional negotiating experience as a successful entrepreneur and attorney.


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