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Jensen's Inequality as the Hidden Engine of History

Now the central point. By a simple mathematical property, one can show why, under a model of uncertainty, [anti-fragile entities] will be likely to benefit in the long run, and thrive, more than shown on the surface, and [fragile entities] are doomed to perish. Over the past decade managers of companies earned in, the aggregate, trillions while retirees lost trillions (the fact that executives get the upside not the downside gives them a convex payoff "free option"). And aggressive tinkering fares vastly better than directed research. How?

Jensen's inequality says the following: for a convex payoff, the expectation of an average will be higher than the average of expectations. For a concave one, the opposite (grandmother's health is worse if on average the temperature is 70 than in an average temperature of 70).

Squaring is a convex function. Take a die (six sides) and consider a payoff equal to the number it lands on. You expect 3½. The square of the expected payoff will be 12¼ (square 3½). Now assume we get the square of the numbers on the die, 15.1666, so, the average of a square payoff is higher than the square of the average payoff.

The implications can be striking as this second order effect explains so much of hidden things in history. In expectation, anything that loves Black Swans will be present in the future. Anything that fears it will be eventually gone — to the extent of its concavity.
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