JAFFRAY WOODRIFF

Woodriff was born in Virginia in 1969 and started trading while still a student at the University of Virginia, where he studied from 1987 to 1991. He was hooked on the idea that a computer could find patterns in market prices that no human could spot.

He ran managed accounts and refined his models for over a decade. In 2003 he co-founded Quantitative Investment Management in Charlottesville with Michael Geismar and Greyson Williams.

The firm trades global futures using systematic models, and later added an equity strategy that files 13F reports. By 2011 Forbes listed him among the highest-paid fund managers after one year of roughly $90 million in pay.

In 2012 Jack Schwager profiled him in Hedge Fund Market Wizards as one of the sharpest systematic traders alive. QIM grew to manage several billion dollars, with regulatory assets around $3.3 billion by the end of 2018.

Quantitative Investment Management (QIM), Quantitative Foundation

Woodriff is a systematic futures trader, which means a computer makes the calls and he mostly builds and supervises the machine. He does not predict where oil or the S&P is going.

He hunts for statistical patterns in old price data that keep working across many different markets. His signature move is data mining done carefully.

Most people torture their data until it confesses, then trade a pattern that was really just luck. Woodriff instead mines pure random data for fake patterns first, then demands his real strategies clearly beat that random benchmark before he trusts them.

He blends hundreds of models together rather than betting on one, because a crowd of okay models is sturdier than one brilliant model that might be a fluke.

The win is the method itself, and the proof is his personal track record. Schwager reported that Woodriff's own futures trading account compounded at an average of about 118% a year, an almost absurd number that few traders on earth have matched.

He got there not with one killer trade but by industrializing the search for patterns. As he put it, he would rather have the computer test trillions of patterns than the few hundred a human could dream up.

That approach turned a college obsession into a firm managing billions and a personal fortune large enough to write nine-figure checks to a university.

The humbling truth about systematic trading is that even the master of avoiding self-deception could not make dazzling early returns last forever once the money got big. QIM's flagship futures strategy went through a rough multi-year stretch in the early 2010s as assets swelled, the classic problem where a strategy that shines with a small pot gets crowded and dulled at scale.

Woodriff has been unusually honest that most quants blow up precisely because they trust patterns that were never real. The lesson he preaches is the one his own fund learned the hard way.

Past performance can be a mirage, and size is the enemy of a good edge.

Woodriff believes the biggest enemy in investing is not the market, it is your own ability to fool yourself. He is obsessed with overfitting, which is when a model looks brilliant on past data but only because it memorized noise that will never repeat.

He argues that using out-of-sample testing is not enough, because the moment you pick the model that tested best you have quietly turned your test data into training data. So he treats older market data as gold, since patterns that held up for decades are far more likely to be real.

His core belief is simple. Respect randomness, or randomness will take your money.

Woodriff keeps his family life private and grew up in Virginia, where he has stayed his whole career. Details about his spouse and children are not publicly disclosed in any meaningful way.

He attended the University of Virginia from 1987 to 1991, and it shaped everything that followed. He started building trading ideas as a student and never really left Charlottesville.

Decades later he closed the loop by funding UVA's School of Data Science, the field his whole career was built on.

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