Success In Sails

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The sounds of Crosby, Stills, Nash and Young serenade excursion customers as they step aboard The Cat, Jim Trilling’s pearl white catamaran. Like entering the living room of a palatial home at sea, guests hand their shoes to Trilling’s crew. That’s so The Cat’s deck stays spotlessly clean.

It’s hard to read Trilling’s eyes behind his ever-present sunglasses. What’s not hard to read is the smile that creases this Boston native’s face as he surveys the length of his 54-foot home away from home. As long as guests are having a good time and The Cat is running seamlessly across the Caribbean Sea, life is good for the 64-year-old Trilling.

Two years removed from receiving a kidney transplant, Trilling lets his crew take charge. On this day, Trilling’s job is to make sure his paying guests feel special and relaxed. On today’s six-hour snorkeling excursion to St. John, the goal is to ensure pleasant vacation memories and vivid testimonials.

Jim’s big adventure
In 1980, Trilling departed from Boston on what he calls “a world adventure.” After spending five years building his boat by hand, Trilling’s goal was to sail around the world. Four days after embarking on his trip, Trilling and his crew encountered the “perfect storm.” Trilling’s 32-foot Westsail limped into the safe harbor of Hamilton, Bermuda, battered but not beaten.

After a two-month detour rebuilding the boat dubbed “Windsong,” sails were set for the next leg of Trilling’s adventure. Upon arriving in St. Thomas in the U.S. Virgin Islands, Trilling’s life would reach a turning point. He concocted the idea of offering six-passenger sailing and snorkeling adventures to the handful of cruise ships that docked in the island’s Charlotte Amalie Harbour. With a business belief that “the worst thing they could say is no,” the former Brookline High School grad began knocking on doors of ship operators.

Three weeks to “yes”
“I called on cruise ships for about three weeks. Eventually, the cruise director from Costa Cruise Lines agreed to offer my excursion, the “Windsong Sailing & Snorkeling Adventure,” to his passengers. Looking back, I guess this was my business break,” Trilling recalled.

“One of my first customers was a news reporter from WGN television in Chicago,” Trilling said. “I took his group on a sailing and snorkeling adventure on my original 32-foot boat. At the time, this type of excursion was unheard of. The reporter gave a great testimonial about his trip to the cruise line. He also talked about his excursion on the air when he got back to Chicago. Costa Cruise Lines began to regularly book through me from this point on.”

A win-win relationship
Three decades after his initial success in the boating adventure business, Trilling is firmly entrenched as an entrepreneur and resident of St. Thomas. Today, The Cat, and a second boat named Castaway Cat, are the centerpieces to Fun Water Tours. Trilling built and paid for these twin catamaran purchases in 2010 by continuing to knock on doors. His sales diligence has evolved into relationships that include four of the major players in St. Thomas commerce. Trilling believes these business relationships are the cornerstones for his enduring success.

The Princess, Norwegian and Costa Cruise Lines regularly work with Trilling’s company. The cruise lines see The Cat and The Castaway Cat as a way to deliver intimate island experiences for their customers. Trilling sees his relationship with the cruise lines as mutually beneficial. “They depend on us to create memories for their passengers, and we depend on them to pay our bills,” he said.

The fourth major spoke in Trilling’s business wheel is the Marriott Frenchman’s Reef Resort, located on a bluff directly above the spot where Trilling docks his boat and picks up customers each day. “This beautiful hotel is a 37-year-old landmark and one of the most famous places on the island,” Trilling said. “The cruise lines and the Marriott are the reasons I could build The Cats. I’m very grateful to have these relationships. I believe the cruise lines and the Marriott feel positive about the job we do. After an excursion, we return their customers feeling happy and satisfied. It’s a win-win.”

True blue crew
Trilling’s business philosophy regarding mutual dependence extends to the feelings and rapport he has with his employees. This devotion came in handy two years ago when Trilling’s health almost capsized from end-stage kidney disease.

In 2009, Trilling headed back to Boston to undergo dialysis and ultimately receive a new kidney donated by a friend. His crew took over the keys to his boats and his business. “My job is to secure new business, write up contracts and pay the bills,” Trilling said. “My crew runs the business. They definitely did that when I got sick.”

The loyalty of The Cat crew runs deep. “I’ve got employees who always show up and rarely call in sick,” Trilling said. “I’m a lucky guy.”

What’s interesting is the hiring isn’t performed by Trilling. He delegates this responsibility to his captain, Joe Morgan. The Denver native has worked for Trilling since he arrived on St. Thomas five years ago. Yes, on an island that is one of the rum capitals of the world, guests can tell friends they were on a boat navigated by Captain Morgan.

The other key member of The Cat’s team is Becca Lee, a 28-year-old native of Dallas. Lee, The Cat’s snorkeling director and resident chef, showed up in St. Thomas with only the promise of space on a friend’s couch. Lee revealed that networking and finding a job in St. Thomas is done the old-fashioned way: in a bar. “I met Joe Morgan at a bar here called the Rum Shack,” Lee said. “I explained that I had no experience working on a boat. Joe said this business is more about personality and a good work ethic. He said I’d get trained to learn the boat business. That was four-and-a half years ago,” she continued with a smile.

That’s entertainment
Trilling offers a different slant on what business he’s in. He believes The Cat and its crew are in the entertainment business. The truth is that life on The Cat isn’t just fun and games. The goal is to keep the Fun Water Tours business buoyant. This often means booking and running up to three excursions per day. So if an evening sunset cruise is on the calendar, the crew arrives home after dark feeling satisfied, yet spent.

The luxurious Cat is Trilling’s reward for surviving his kidney replacement procedure. “The Cat is the last item on my bucket list,” he said. “When I was on dialysis and working up to receiving my transplant, I decided money doesn’t belong to you until you spend it.” One doesn’t need to see Trilling’s eyes behind the sunglasses to see that he was beaming from this confession.

Living the dream
The story behind how a boat got its name can be revealing. The Cat’s moniker awakened Trilling in the middle of the night. “I woke up one night and the name came to me like it was out of a dream,” he said. “Here in St. Thomas, at least half the new customers will say they want to go on a cat, rather than a catamaran. I figured that for those customers who weren’t sure which boat they wanted to go on, I would have them covered.”

More than 30 years since departing on his “world adventure,” Trilling is still living the dream. It’s amazing the business you can build, the people you can meet and the life you can experience if you just knock on a few doors.

About Tim Cotroneo 20 Articles
Tim Cotroneo is a freelance writer from Lino Lakes, Minn., with a passion for travel and a future Caribbean zip code.

1 Comment

  1. This story just goes to show you that you cannot be in business unless someone gives you a break. In order to maintain a great company there needs to be good feedback, exposure, and most importantly someone who can trust you enough in you to give you their money. If it happened for Jim Trilling, who’s not to say there aren?t another thousand Jim’s out there just waiting for their chance.

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