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’70s road trip ended at a career-changing destination

If you graduated college in the mid-to-late ’70s, there is a strong possibility that you did not graduate swamped with college loans. Not only was that common, but also when I graduated from Boston College most of my classmates spent their first year out of school traveling or spent the winter working at a Western ski resort for the almighty free ski season pass. Those were the days!

If you graduated college in the mid-to-late ’70s, there is a strong possibility that you did not graduate swamped with college loans. Not only was that common, but also when I graduated from Boston College most of my classmates spent their first year out of school traveling or spent the winter working at a Western ski resort for the almighty free ski season pass. Those were the days!


I took a different route. My first job was working for my family's roofing business. That first winter the cold reality set in. So what do you do when you’re not happy with your first career choice? You go back to school. With no real idea of what I wanted to do, the notion of law school seemed like a good path.

When you tell your folks that you want to quit the family business, there are very few acceptable reasons. I had two choices: I could tell them I was going back to school to become a priest or I was going to law school. No one would have had faith in me had I tried the seminary approach.

I took the LSATs. Then something happened that turned out to be somewhat life-changing. About a week after I took the exam, my best friend called and said he was going to graduate school in California. Did I want to drive there with him?

I could never refuse a road trip. We loaded up his Jeep CJ 4 (yes, the CJ 4). No doors, heat or radio, and off we went. Fast forward five weeks: We arrived in San Diego. After spending a few days on the beach, settling down from the long haul in the most uncomfortable vehicle ever designed, I knew I had to do something fast.

My friend had a relative who was doing a refit of Victoria, a sister ship to the 72-foot Herreshoff-designed Ticonderoga at the Kettenburg boatyard in San Diego. I found myself at the yard most days, and eventually I became part of the office crew trying to keep track of the “overruns.” And I was hooked.

But now what? Having spent my early years on Candlewood Lake in Connecticut, and summers with my uncle boating out of Mamaroneck Harbor in New York, I was interested in boats, but this was a whole new world. After a short stint working in the office for a New York group of marina owners, I went to what was then the premier yacht yard in Connecticut, Yacht Haven Marine Center in Stamford. Unannounced I walked into the corporate office and spoke with Dennis Snow, who was then Yacht Haven’s vice president. We talked for about an hour and he said, “Just give me some time. We want you here.”

That afternoon I did not know he would become one of my best friends and my mentor. To this day I have never seen anyone establish such a natural rapport with workers and customers. Soon I was sitting behind Dennis' desk as vice president and Dennis went on to become president of Yacht Haven before leaving to own his own yard in Mystic, Conn.

An 800-slip, full-service marina in the ’80s was a good place to work. The International Offshore Rule sailboat racing scene was in full force, and all of the big powerboats stopped in Stamford on their way to and from Florida. It was not unusual to arrive at work in the morning and find two maxi sailboats tied alongside, filled with 18 or so Aussies on board, greeting you with “Good morning, mate.”

The weeks leading up to major regattas were like international events, with all of the New Zealanders and Australian and English crews around. More than once, Ted Turner flew in to race on his Sparkman & Stephens-designed Tenacious. Of course, he was always late, and a seaplane would land somewhere near the starting line to get him to the boat. Even now I will be walking in Newport, Northeast Harbor or Fort Lauderdale and vaguely recognize a face from the crew of one of the “big boys.”

As good as the ’80s were to yachting, the early ’90s were as bad. The luxury tax and the recession changed the face of boating forever. Racing nearly died, big boats did not travel south nearly as much and the general concept of “time deprivation” affected the boating industry. The marina went from 800 slips with a waiting list to a 35 percent vacancy rate. The “working yard” slowed considerably. By the mid-’90s Yacht Haven was sold, and after 15 great years a career change was inevitable.

Now what? Candidly, it was a tough time. I wanted to make a change from the boatyard, but every offer I had was from another yard. I eventually took a job with a then-growing charter company, Trade Wind Yachts. Doing some training in the British Virgin Islands sounded inviting. The plan was to open a few offices in New England.

I did not approach this as a long-term career path, but for the first time I was exposed to a great print advertising campaign, online bookings and the new global system of interconnected computer networks — the Internet. I still remember the president of the company predicting that the new age of shopping would be done on computers. We all thought he was mad.

All during my years at Yacht Haven and at Trade Wind Yachts, I was constantly sending clients to brokers when my customers wanted to sell or buy a boat. I had come in contact with hundreds, if not thousands, of boaters. My go-to guy/firm was Prestige Yacht Sales. Michael Frank had started Prestige while I was working in the yard, and I had always admired how he handled not only his customers, but also the vendors. One day, while I was finishing up at Trade Wind Yachts and introducing Michael to a client, he said, “You send me so many customers. Why don't you think of becoming a yacht broker”?

Because I knew about boats and plenty of boaters, I thought I might give it a try. I had never thought of myself as a salesman. Even now. I still think of myself as a customer service worker who happens to sell boats.

I started at Prestige Yacht Sales 18 years ago. We have grown from one office with three brokers to three offices (Norwalk, Essex and Mystic, Conn.) and seven full-time brokers selling brokerage boats and new Beneteau sailboats, Hunt yachts and Southport boats. Michael and I became partners early in my tenure, and last year he retired to live full time in Punta Gorda, Fla.

Oh, I almost forgot to finish my story about the LSATs. While I was in California my folks moved from my childhood house. In those days test results were sent via snail mail. Sometime while I was away and they were moving, the scores arrived. To this day I have no idea what happened to them. I was in the marine business.

Tom Pilkington is the owner of Prestige Yacht Sales in Connecticut.



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