Connections | Magazine

Dad taught me the art of negotiating when I was just a kid

Buying, fixing up, and selling small boats with Dad helped me learn skills I still use today.

Graham Roumieu for The Boston Globe

Father-son bonding often involves a baseball and glove or a bicycle and training wheels. In my case, it involved the Boston Sunday Globe classifieds and used boats that had seen better days.

America was just barely out of the Great Depression as I started first grade, in 1942. My sister, our parents, and I lived in a one-bedroom apartment above a taxi stand and a liquor store on Salem Street in Medford. Mom and Dad slept in the living room.

With homeownership the family aspiration, Dad, a housepainter, always sought opportunities to work overtime. And I followed his lead. While other kids were playing sports, I was finding ways to earn money. My first entrepreneurial venture, at age 6, was peddling bottles of soda to construction workers from my little red wagon. By junior high, I had talked my way into the Ford motor plant in Somerville (at what’s now Assembly Square) to sell ice cream to line workers. My solo enterprises taught me a lot about how businesses work and how people think. And they prepared me for a joint venture with my dad when I was around 14.


In the 1950s, the newspaper was the main forum for advertising items for sale. The Sunday Globe often featured more than 100 pages of classified ads. That section arrived in stores on Saturday. I strolled down Salem Street to Kitsis Pharmacy around noon every Saturday to buy just the classifieds section. If Mrs. Kitsis thought I was a bit off because of my curious purchasing habits, she never said so.

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At home, my father and I carefully combed hundreds of small-type ads for used boats, circling good prospects. Then I made the initial phone calls, knowing that getting a jump on Sunday readers would work to our advantage. “Just make sure to tell them you don’t have much money,” my father said. “You buy low, and you sell high. But you have to do both.”

He wanted me to understand that the true value of any item is “whatever you can get for it.” That means value is what a willing buyer will pay a willing seller. We were willing buyers of a boat at a bargain price, and when we placed our own classified ad in a subsequent Sunday paper, we were willing sellers of that same boat.

Dad had the negotiating down to an art form, and in the beginning he handled the entire in-person transaction while I watched. When he got a price he liked, he paid cash and immediately towed our find of the day home. Our typical purchase was a 12-foot boat with a 10-horsepower inboard motor and a trailer, for $700 to $800. If the boat needed to be scrubbed or painted, we did that before offering it for resale, knowing that the effort would pay off handsomely. Occasionally, though, we bought a boat that was in such good condition that we were able to turn around and sell it for a 50 percent profit.

For me, the real profit was all the one-on-one time it gave me with my father, and the opportunity to learn from him. Dad was a terrific closer.


Negotiating experience begins in the home. Children who cajole their parents for more freedom and privileges are practicing bargaining. Parents who dread pleas of “Why do I have to go to bed so early?” might find solace in the possibility of having a future master negotiator in the family.

Over time, Dad encouraged my participation in boat negotiations. “Someday you will be glad for this practice,” he said.

Even though the transaction amounts were relatively modest, I found myself leaning on those early lessons when I was negotiating multimillion-dollar business transactions years later. As always, Dad was right.

Bill Cummings is the founder of Cummings Properties and cofounder of the Cummings Foundation. He recently published “Starting Small and Making It Big: An Entrepreneur’s Journey to Billion-Dollar Philanthropist,” from which this essay is adapted.