In my newly-published book, They Named You Right, I talk about the roots of my fascination with the game of chess, and how it relates to the mental game of running, growing and selling businesses in the graphic arts industry.

Let’s wind the clock back 50 years to 1973. Here’s an edited excerpt from my book:

“College is the ticket to bigger and better things. But right from the start, I knew Rock LaManna was the square peg trying to fit into the round hole that was St. Mary’s College.

My dorm’s third floor was filled with mostly the best students, bound for careers in law and medicine. Our floor claimed the highest average GPA in the school. The pressure was on from day one.

I was surrounded by guys who studied like their lives depended on it. They also taught me to play chess, which I love to this day.

However, my people were down on the second floor, where the hockey players lived, where music blared throughout the weekends: Allman Brothers Band, Grateful Dead, Santana. The second-floor guys studied all week and then partied their brains out on the weekends.”

Somehow, I pulled off a 3.2 GPA in my first semester. But the good grades wouldn’t last. Both my college advisor and dad noticed that hockey, partying, and socializing were catching up with me. I would ultimately master college. But that particular environment didn’t fit the way I liked to learn. I consume information quickly and dig deep into my interests. I prefer being around people who can match the pace of my ideas and energy – and can take action. I like the world of business.

It was decided. I would go to work at Vomela Specialty Company, my dad’s family business. You’ve heard me talk about Vomela: the hard work, my leadership and ownership roles, challenges from inside and outside, growth, opportunities, and the ultimate sale of the business to someone outside the family. A real roller coaster, which I recount in my book.

Throughout that phase of my career, the high-level strategic lessons of chess applied to my work. There is nothing like learning the strategic gamesmanship of chess when you are young enough to benefit from it.

The scholarly aspect of my life would come into play later when, as a seasoned owner, I attended Harvard Business School. Through it all – work, marriage, friendships, and personal growth – chess was a constant companion, distraction and passion.

In last year’s series, we talked about buy-sell-grow lessons from the physical game of hockey. This year, we get cerebral.

Even if you don’t play chess, I’m sure you’re familiar enough with the game to see how there are valuable business lessons that can be learned. Even more specifically, chess has helped me in the deal
flow arena.

Over the course of this series, we’ll talk about strategy, power moves, going head-to-head with your competition, planning scenarios many moves ahead but always being aware of how things change with each move, learning to read your opponent’s signals and much more.

Clients tell me they are surprised by the long game of selling a business. Like chess, it requires pacing, focus and stamina. These qualities are essential for owners on a three- to five-year runway for selling or transitioning the business.

Here’s an overview of what we’ll be digging into over the course of the next year:

Strategic Thinking

Playing chess and selling a business both require strategic thinking, planning, game knowledge and the ability to anticipate your opponent’s moves. In chess, you must think several moves ahead and adjust as the game progresses.

Similarly, when selling a business, you must anticipate the buyer’s needs and be prepared to make concessions or negotiate to reach a successful sale. Both activities also require patience and self-discipline. Chess helps you develop analytical skills, the ability to evaluate different scenarios, and well-founded decision-making.

Noticing Patterns

Chess and the “game” of business require the ability to recognize patterns, unspoken cues, personal chemistry and more – and then use them to your advantage. 

Managing Risk

Both activities require risk-taking, as there is always the possibility that a move may not work out as planned.

Being Focused But Flexible

To stay on your game, you need focus and flexibility, a combination that takes practice and experience. You must remain fixed on your goal and not get distracted.

Knowledge and Confidence

Experience matters. The longer you play – and play at a higher level – the more confidence you’ll have in making decisions that lead to strong wins.

Critical Thinking and Problem Solving

Playing chess deepens critical thinking and problem-solving skills, which are essential for success in the buy-sell-grow realm.

Over the year, we’ll talk about real-world examples, places in the deal flow arena where things shifted unexpectedly, getting into your opponent’s head, and ultimately mastering the end game. My goal, as always, is to help you prepare for the changing world of business, new opportunities, and the many ways you can leverage your knowledge to operate at a master level.

With almost 50 years in the graphic arts industry, I’ve cultivated a comprehensive international database and a deep network of trusted relationships to facilitate introductions in the deal flow arena. Let me provide unmatched insight into the buy-sell-grow process.

I also welcome your feedback. If you love chess, drop me a line at [email protected]. Let me know your perspective on the similarities between chess and business – specifically entrepreneurship, mergers and acquisitions, deal flow, and sell-side tactics and strategies.


Rock LaManna is The Deal Flow Guy. He helps qualified buyers and investors find businesses that are ready for acquisition or transition. On the sell side, he helps owners improve their businesses, increase value, and position strategically in anticipation of sale, exit or succession. Sign up for his newsletter at TheDealFlowGuy.com and start the process. They Named You Right, Rock’s newly-published business memoir, is available at www.theynamedyouright.com in hard cover, soft cover and as an ebook.