Optimizing S-shaped utility and implications for risk management
John Armstrong, Damiano Brigo

TL;DR
This paper examines how traditional risk measures like VaR and ES are ineffective against tail-risk-seeking investors with S-shaped utility, and proposes alternative constraints to mitigate unbounded risk-taking.
Contribution
It demonstrates that standard risk measures do not constrain S-shaped utility maximization and introduces utility-based constraints as a more effective risk management approach.
Findings
VaR and ES do not limit tail-risk-seeking behavior in standard models.
Conventional concave utility constraints can reduce maximal S-shaped utility.
Unbounded S-shaped utilities lead to unbounded negative utility under constraints.
Abstract
We consider market players with tail-risk-seeking behaviour as exemplified by the S-shaped utility introduced by Kahneman and Tversky. We argue that risk measures such as value at risk (VaR) and expected shortfall (ES) are ineffective in constraining such players. We show that, in many standard market models, product design aimed at utility maximization is not constrained at all by VaR or ES bounds: the maximized utility corresponding to the optimal payoff is the same with or without ES constraints. By contrast we show that, in reasonable markets, risk management constraints based on a second more conventional concave utility function can reduce the maximum S-shaped utility that can be achieved by the investor, even if the constraining utility function is only rather modestly concave. It follows that product designs leading to unbounded S-shaped utilities will lead to unbounded negative…
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