"The simulations have shown interesting, promising results," Cucchiaro says. "We recently began a live experiment with real money, and we will run this test for a period of time before considering whether or not to introduce a new portfolio strategy based on this experiment."

As for emerging markets, Cucchiaro says the firm has recently added equity and currency indexes from India, Brazil and South Korea into its investment universe.

Charting the Seas
Employees say Windward offers an open, collegial work atmosphere. "It's a flat environment that encourages as much communication as possible," says Louis Crosier, managing principal and a member of the executive committee along with Cucchiaro and Phillips. "We encourage employees at every level to pursue professional development."

Windward works hard and plays hard. On its Web site, it profiles staff members and highlights their athletic pursuits and achievements. Every year, the company takes an annual ski retreat that mixes strategizing and schussing. This year's trip is to Big Sky in Montana.

Cucchiaro's athletic background is particularly interesting. An all-American in sailing while at MIT, he won a gold medal in yachting at the 1979 Pan American Games in Puerto Rico. He qualified for the 1980 U.S. Olympic team, but missed his Olympic moment when the U.S. led a boycott of the games in Moscow that year to protest the Soviet invasion of Afghanistan.

But sailing is still very much in his blood and in his investment philosophy. Hence the name, "Windward."

"Sailing to Windward is very analogous to investing in markets where you form judgments on which way the winds might shift, employ competitive strategies to stay ahead of the competition, and analyze how currents are affecting the race," Cucchiaro says.

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