Confessions of a 21st-Century Aviatrix

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I’ve known Topsy Taylor for about 20 years. We met through mutual friends who were working to raise funds for City Harvest. She is a New York girl with a real New York ancestral history. She’s one of those individuals who is naturally friendly and agreeable, but also one who expresses her opinions fairly and clearly. She’d never bring it up but she has an “old New York” background. Her great-great-great grandfather, Moses Taylor, was a 19th-century New York businessman and banker who, through his father, had a close business relationship with the first John Jacob Astor.

Moses, who was born in 1806, was a very prosperous sugar importer and business leader. He vastly expanded his investments into the First National City Bank (with a controlling interest) as well as into railroads and local gas companies that eventually became (through mergers) what is known as Con Edison. When he died in 1882, he left a fortune of more than $1 billion (in today’s dollars). That fortune was distributed over the following decades to several prominent New York families of the 20th century.

None of this information is worn by Topsy as relevant to her definition of herself. She has the accent and the bearing that speak “uppah clahass” New York—one of the last mid-Atlantic accents. It is the result, no doubt, of her upbringing and schooling. It is the kind of accent and bearing that might easily lead one to believe that they are in the presence of a big snob—with a capital “B.” She is also, since her youth, a very worldly woman who has traveled frequently and widely in the thick of the jet set. She is also one of the nicest, kindest, and most directly honest women in New York. I wouldn’t know anything about her ancestral background if I hadn’t researched it. What does seem relevant is that the lady has naturally inherited her entrepreneurial instincts.

When she was seven or eight, Topsy had her first plane ride. (This was in 1948 in Newport, Rhode Island.) There was a retired army pilot man named Bob Wood who had a small plane that he flew and chartered out to people in the community. On that first plane ride, Topsy was allowed to sit in the cockpit next to the pilot. It was a first; nobody in the family had ever been in an airplane. Her sole memory of that first experience was looking down at the land below and seeing how it lay with the towns and houses—neat and tidy with the streets in squares. The child was fascinated.

As a child, she grew up mainly in South Carolina and in Rhode Island in the summertime. After that initial family flight, her father would charter a small Cessna to take them back and forth. Her parents also used Bob Wood to go to Saratoga, New York, for the racing season; to Canada for fishing; or even for visiting friends a few hundred miles away.

The way some young girls are attracted to horses, Topsy was attracted to the technology of motor vehicles. She was 11 the first time she drove a car in South Carolina. She loved it. When she was 14, she got her first driver’s license. That, of course, was in the mid-1950s; the rules have changed since then.

At 20, she soloed in a Piper Cub for the first time in Camden, South Carolina. She had had a fear of flying—despite loving it—and she decided she’d be “better off sitting up front to get through the fear of it.” On that flight, she had to take off, come around, land, and then do it again. “In those days at that airport, after you soloed successfully,” she told me, “they’d cut off a piece of the tail of your shirt and put it on the wall with your name on it. Driving home, I was speechless. I felt as if I’d climbed Mount Everest.”

Two years later, in 1963, Topsy was working for Vogue. In the summertime, she would fly back and forth from New York to Newport on weekends. “A group of six of us would charter, and I always sat up with the pilot and do the radio work and that kind of stuff,” she explained. “That way, I got to learn to speak to LaGuardia as we were arriving and departing.”

Always curious, in 1974, she got her private pilot certificate in a Beechcraft Baron 58, flying out of LaGuardia airport and all over the Northeast. In 1985, Topsy started taking lessons at Long Island MacArthur Airport to get her commercial pilot certificate for helicopters. Her flight instructor was a man named John Kjekstad.

She loved it so much that, the next year, she bought a helicopter: a Bell 206 JetRanger (which was painted red). She started flying her friends back and forth between New York and the Hamptons or Newport. When her daughter, Lisa McFadden, entered the St. Paul’s School, Topsy would fly her and Pauline Boardman’s daughter Samantha to Concord, New Hampshire—while dropping Pauline’s daughter Serena at the Brooks School in North Andover, Massachusetts.

Friends who heard about it were interested in chartering Topsy’s helicopter to get back and forth to Southampton or Newport (or another destination). Topsy—who never flew without a co-pilot—asked John to help. As more and more people became interested in the “service” (getting a ride versus driving to a destination or another airport), John became the chief pilot.

They began to do more and more business. John was able to get a certificate for air-taxi operators and he and Topsy partnered to create Helicopter Flight Services, which operates out of Manhattan. The air-taxi service also began filling requests for aerial sightseeing over Manhattan. As they got busier and busier, they acquired a second helicopter and then a third helicopter. Today, Helicopter Flight Service owns a fleet of Bell 407s plus a Bell 427, producing gross revenues in the eight figures.

John Kjekstad has more than 18,000 hours of combined helicopter and fixed-wing experience. He also earned an Airline Transport Rating, which is the most esteemed in ratings. Plus, he is a certified flight instructor and certified instrument instructor for helicopters.

Although Topsy is one of the few women in aviation doing business, she’s unimpressed. Her main focus these days is safety, integrity, and ensuring that Helicopter Flight Services is #1 in the helicopter business. She reckons: “I’ve always done things that fascinated me, whether with someone or on my own. It’s very important for a person to do something that’s just important to them.” Good for the customers too, I’d say.

For more information, contact Helicopter Flight Services at 212.355.0801 or heliny.com.