Robert Wilson falls under the title of “the greatest investor you’ve never heard of.” He turned $15,000 into $230 million from 1958 to 1986.
Wilson was a long/short investor who wasn’t afraid to use leverage. He began his career as an analyst at A.G. Becker & Co. He went on to open his own hedge fund in 1968 called Robert Wilson Associates. Within a couple of years, he was strictly running his own money. He gave it up in 1986 because he promised himself that if he ever failed to beat the market for three years straight, he’d quit.
Near the end of his career, he talked with George Goodman on Adam Smith’s Money World. He discussed his investment strategy. He also highlighted how successful investments can go to your head.
In Wilson’s case, his ego got the best of him and produced his biggest loss.
It happened in 1978. Wilson bet against Resorts International. Resorts was a small casino operator with a single casino in the Bahamas, with a second casino planned in Atlantic City. The company bet its future on legalized gambling in Atlantic City. Continue Reading…

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