Stephen Cucchiaro says that on a day when he was eight, he was in Boston with his parents and his father drove past MIT, explaining it would be a great school for his son, who excelled in math and science. Awed by the Institute’s great dome, Cucchiaro says, “I always dreamed of attending MIT.”

But in high school, his guidance counselor told him the dream was impossible. “I was devastated. Fortunately, my parents were supportive and encouraged me to send in the application,” says Cucchiaro, who earned a bachelor’s degree from MIT in mathematics in 1974.

Recently, “to give back to a place that gave me so much,” Cucchiaro, along with his wife, Anne, gave MIT the largest gift ever to the Institute’s Sailing Pavilion.

“My wife and I are fortunate to consider such a gift, and it seemed like a great time to give back,” he says. “I have so many positive feelings of my experience at MIT and also of sailing. At MIT, I went from a weekend sailor to a nationally ranked one.”

At MIT, Cucchiaro was a two-time All-American in collegiate sailing. He was on the Olympic sailing team from 1976 to 1980 and was the U.S. national sailing champion in 1978. In 1979, he won the gold medal in the Pan American Olympic Games.

He says that the lessons he learned from sailing were analogous to many of those in life.

“In sailing, I learned to make decisions under uncertainty, the benefit of having discipline and not taking wild chances, and to think two steps ahead of the competition. I found all this extremely useful in my professional life,” says Cucchiaro, now an investment manager. “The analogies are tremendous. Students who learn about sailing and racing can apply those same skills across many fields.”


In 1977, Cucchiaro earned an MBA from the Wharton School at the University of Pennsylvania. When he graduated, he promised himself that long-term he would build his own mathematical model of the global capital markets, using much of what he had learned at MIT. It would be an innovative approach, entirely different from what the industry was practicing. He knew that one day he would realize his goal, but in the short term, he says, “I needed a real job.”

Cucchiaro joined Coopers and Lybrand in financial consulting and soon was recruited by Data Resources as a senior economist. In 1982, he ran the strategy consulting practice of CSP International, then he co-founded Datext in Boston, the first company to use CD-ROM technology to publish information on publicly traded companies. Next, he joined Lotus Development as general manager of communications and information software. In 1992, he became president of ICAD, a Cambridge software technology firm, helping position the company for an IPO and subsequent sale to Oracle Corporation. Keeping that long promise to himself, he decided to build a new investment company using the innovative methods he learned at MIT. In 1994, Cucchiaro singularly launched Windward Investment Management in Boston. Now, the company has 30 employees and manages more than $3 billion in assets for private and institutional clients.


“MIT was a transformational experience in my life,” Cucchiaro says. “Because of my background, I was able to develop a new approach for analyzing the markets. We now practice the same investing methodology that I began researching at MIT, and it’s been a successful endeavor.

“Having the opportunity to sail at MIT allowed me to build a lot of self-confidence that carried over into other aspects of my life, and that made a fundamental difference in our success.”

Cucchiaro has been married to his wife, Anne, for nine years. She is a landscape painter, who has a studio in Boston’s South End. Her work is displayed in the corporate offices of her husband’s company. Often, he says, clients unaware that she is his wife, comment on her talent. “So far, they have a 100 percent track record of positive comments,” he says. The couple enjoys free time on their 43-foot sailboat in Marblehead, MA.

“The best possible outcome of our gift,” Cucchiaro says, “would be that students learn to sail — not only as a release from the academic pressures, but also to learn important lessons about life, ones that can apply in any field they pursue.”