Ray Dalio was born in Jackson Heights, in the borough of Queens, New York City. An only child, his mother was a homemaker, his father a jazz musician who played clarinet and saxophone in night clubs such as Manhattan’s Copacabana. When Ray was eight, the family moved farther out on Long Island to the suburban community of Manhasset. The young Ray Dalio enjoyed sports and playing with his friends, but disliked the routine of school, particularly rote memorization. He was far from lazy, however. For spending money, he held down a paper route, mowed his neighbors’ lawns and shoveled snow from their driveways. From age 12, he worked as a caddy at the Links Golf Club, an exclusive course where his customers included the Duke of Windsor (formerly King Edward VIII of England) and the former vice president (soon-to-be president) Richard Nixon, as well as many Wall Street investors.

In the boom years of the 1960s, talk on the golf links centered on the surging stock market and Ray Dalio was intrigued. With $300 he had saved from his caddy earnings, he bought shares of Northeast Airlines. At five dollars a share, it was the only major company whose stock he could afford. As it happened, Northeast became the object of a merger effort, and the 12-year-old caddy quickly tripled his investment. Ray Dalio was hooked. He read the annual reports of major companies, and engaged older investors in conversation. By trial and error, he learned principles he has continued to apply in his investing career. He found that even careful research can result in mistakes, and that mistakes can be expensive. He also learned that the only way to beat the market is to be right when others are wrong. When he formed an opinion of the prospects of a given stock, he asked the smartest investors he knew to critique his reasoning. By the time he graduated from high school, he had assembled a stock portfolio worth several thousand dollars, a significant amount for a teenager in the late ’60s.

Given his unexceptional academic performance in high school, Ray Dalio had some difficulty finding a college. He eventually enrolled at C. W. Post College, a campus of Long Island University in nearby Brookeville. Although he continued to buy and sell stocks in college, Dalio also became interested in commodity futures. The low margin requirements attracted him to this sector, where he saw an opportunity to earn a considerable profit on a minimal investment.

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