Fort Myers Company Turns Sailing Into Multimillion Enterprise

Sailing is a wonderful, exhilarating sport for those who have the training and experience to enjoy the ever-changing interplay of wind and water on a boat driven by its sails. Those who leave port on a rental or on their newly purchased boat without a solid understanding of sailing fundamentals will likely spend a terror-filled afternoon wondering why their beautiful investment won’t turn in the proper direction or return easily to the dock they regret ever having left.

But, for the multitudes who have learned to sail at a branch of the Fort Myers-based Offshore Sailing School, sailing becomes a lifelong pleasure on weekend getaways, two-week charters, endless cruising in the Caribbean or daring passages around the world.

Owners Steve and Doris Colgate operate nine training locations from Chicago to Tortola. Their most recent outlet is their third in Florida—at the Hawks’ Cay Resort on Duck Key. Instructors teach everything from the basics to advanced offshore cruising techniques. Offshore Sailing School boasts more than 100,000 graduates, and, according to Practical Sailor magazine, has trained more new sailors than any other sailing school in the United States. The cost for the course ranges from $1,100 for a five-day session in the off-season to $4,000, depending on the location.

Offshore Sailing School began modestly in New York City in the sixties as a natural outgrowth of Steve’s love for the sport. A sailor since the age of 9, he participated in his first Transatlantic Race at 19. He has also raced in two America’s Cup trials, more than 16 Bermuda Races, eight Fastnets and the 1968 Olympics in Mexico. As skipper of the 54’ Frers sloop SLEUTH, he won first in class in the 1979 Fastnet race in which treacherous storm conditions resulted in 15 deaths.

In 1965, Steve was working in a yacht supply store and sailing whenever he could. A friend with a 34-footer offered to let Steve use it for sailing instruction whenever it was available. Back then, Steve notes that few people knew anything about sailing, much less about teaching the sport. As the word spread about his sailing classes, the business grew slowly.

By 1967, he was able to purchase two Solings—open, full keel boats that were designed for racing but were stable enough to teach neophyte sailors. With a single New York location, winter meant trying to survive on classroom training alone. The same year, Steve and Doris met at a cocktail party. Thus began a 34-year personal and business relationship. Doris began to help out part-time in 1968; they married in 1969. By 1970, she made a leap of faith, quit her job and signed on for a full-time, no salary position with Steve. They were living hand to mouth. As Doris remembers, “We ate a lot of meals at my parent’s house.”

After a decade of relatively slow growth, the business began to take off by the late 1970s. Doris credits their accelerated growth to two key elements: Steve’s ongoing reputation as a talented racer, a highly-respected instructor and a noted seamanship author; and her increasing business sophistication gained through her involvement in the American Women’s Entrepreneurial Organization and through the mentoring she received as a member of the Young President’s Organization. Doris is recognized worldwide for her efforts in bringing women to the sport of sailing. She is founder of the National Women’s Sailing Association and the Women’s Sailing Foundation—organizations that promote sailing to women through educational programs including seminars, hands-on training, publications and workshops. She has recently authored, “Sailing: A Women’s Guide,” which is available from Ragged Mountain Press, a McGraw-Hill company. Her focus on women and boating is reflected in Offshore Sailing School’s women-only courses, where “no yelling” is the rule.

Today, Offshore Sailing School is a multimillion-dollar enterprise with more than 40 full-time employees, 14 of whom work in Fort Myers, which became the headquarters in 1988. The rest of the staff works out of the New York City, Jersey City, Stamford, Chicago, Newport, Captiva, St. Petersburg, Florida Keys and Tortola locations.

Growing into the Corporate Training Market

In addition to their traditional sailing instruction, the Colgates have recently added a corporate training and teambuilding program that customizes short, focused sailing courses based on a company’s specific needs. These training programs utilize sailing as the means to promote teamwork, communication and strategic implementation in the workplace. In conjunction with professional management consultants, programs are developed to meet the needs of individual corporations. The value of the program is easy to understand, as analogies between sailing and business are numerous. Maximizing a sailboat’s performance is similar to maximizing a company’s performance, and nothing beats the close quarters of a sailboat for building teamwork and communication.

Organizations as diverse as U.S. Gypsum and the Boston Red Sox have used Offshore Sailing’s corporate training program. “We chose Offshore’s sailing program for the camaraderie, teamwork, and spirit that sailing fosters,” says John Quigley, vice president of administration for Dr. Pepper/Seven-Up.

Getting Into the Boat Building Business

After using the venerable Soling sailboats for more than two decades, Steve set about designing a boat that would offer a more pleasurable training experience-and be more affordable.

Working with noted designer Jim Taylor and Precision Boat Works, Steve created the Colgate 26—a boat to fit the needs of the recreational sailor—in 1996. So far, he has built 140 of the boats, which boast a spacious cockpit and roomy storage below deck for both daysailing and weekending. Best of all, the Colgate 26—which costs $27,000—is basically unsinkable, even if holed. The Colgate 26 is in use at all Offshore Sailing locations. It has also been chosen by the U.S. Naval Academy for its midshipman training program.

“Now that I’m getting a bit older, I can get all the thrill of a Soling by sailing my Colgate 26 and be far more comfortable and dry doing it,” says Jim Nellen, an owner from Green Bay, Wisc. “The C26 is a very forgiving boat and sails well in all conditions. I’ve been able to sail with a double reefed mainsail alone in heavy winds and easily do all the maneuvers.”