The tale of the turtles must be one of the most interesting, and materially successful, wagers in the history of investment.
Richard Dennis, an iconoclastic, wildcatting, independent Chicago trader, had by 1983 made hundreds of millions of dollars from an initial grubstake of just a few hundred.
Dennis made that fortune on his own terms, in less than 15 years, with no formal training or guidance from anyone. He took calculated risks leveraging up huge amounts of money.
In late 1983 Dennis bet his then partner Bill Eckhardt that he could teach beginners with no experience how to trade to make millions in the same way that he had. His partner responded that great traders were born, not bred. The two men decided to find out who was right. They hired and trained students, nicknamed "Turtles" after Dennis visited a turtle breeding farm, and gave them some simple rules to follow.
In essence, Dennis taught trend following: cutting your losses, and letting your winners run. This may sound easy, but it's a strategy that runs counter to basic human psychology. The turtles managed to make it work by implementing a rigid, rules-based approach for sizing, entering and exiting trades. And the results were - and are - spectacular. As examples of funds managed by successful turtles, Chesapeake Capital-Diversified Fund, with assets of over $1.5bn, had delivered at the time of writing total returns of over 1,400%. EMC Capital Management-Classic, with a longer track record, has delivered total returns of over 16,000%.
For those interested in the topic of trend-following - a more mechanistic and objective style of trading favoured by many hedge funds, as opposed to the largely discretionary management favoured by traditional long-only managers, Michael Covel's latest book is a must-read.