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On Monday October 19, 1987, the Dow Jones Industrial Average fell by more than 500 points. As the stock markets in Europe, Asia, and the United States began to crash, some traders, like Paul Tudor Jones, were able to profit from the fall out; others, like Richard Dennis, lost everything.

Dennis, who was a world-renowned trader throughout the 80’s and 90’s, blew through $10 million in less than 24 hours; by the end of 1988, he had lost a total of $50 million on the stock market. With a business to run and very little money to spend, Dennis could have easily given up on his career as a commodities trader.

But the mastermind behind Turtle Trading was ready to recover from his losses. In the book Market Wizards: Interviews with Top Traders, Dennis shared his approach to dealing with a series of bad trades.

“There is another point that I think is as important: you should expect the unexpected in this business; expect the extreme,” Dennis explained. “Don’t think in terms of boundaries that l...

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