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Evaluating Gambles Using Dynamics outlines his idea of time averaging in contrast to ensemble averaging in a discussion of the St Petersburg Paradox. Note the parallels with volatility drag, median outcomes, and expected values!
As a long-distance, handicapper of Euro races, I look for events in England, France, and Ireland (Grade 1 Horse-Racing Countries) with a high degree of chaos (I have entropy scores for all race-types). From this initial list, I have selected seven race-types that I focus on exclusively. Because of the high level of uncertainty in these races, the market (wisdom of crowds) is a less successful predictor. With a Bayesian-based, Elo-Class algorithm, I generate my own performance figures. Using the performance figures for all entrants in a chosen race, I run a Monte-Carlo simulation of 1000 races that automatically generates a realistic odds-line as final output. Critically, as long as there is at least one overlay (almost always) in the chosen race, I finally run a Haigh-like, Kelly-variant algorithm that selects the final contenders. (As I have stated elsewhere, this list may include both overlays and underlays).
Though not my discipline (National Hunt Racing), Cheltenham's four-day graded stakes meeting is an exception. Effectively, this is the Breeders Cup of jumps racing. Lacking the in-depth expertise required to handicap this form of thoroughbred racing, I seek to focus on novice races where historical knowledge is as informative as current form. To that end, the Supreme Novices Hurdle has many similarities to the Kentucky Derby - young horses, many attempting a graded stakes, championship race for the first-time with little form in the book. Using dosage analysis of the "in-the-money" finishers over the last ten years and ranking the current field against this metric to identify "live" outsiders, shortlisted two interesting contenders - Shaneshill (14/1) and Tell Us More (25/1). Though not necessarily the most likely winners, these two selections are the best matched to previous contenders on dosage and, therefore, worthy of punting in both the win and show markets!