Due to the principal-agent problem in the asset management industry, most money managers rationally have a propensity to use a negatively skewed payoff distribution. This kind of behavior, in aggregate, is also evidenced in the historical data, which shows significant losses for professional investors during the largest market downturns. Most investors and asset allocators, in addition to these negatively skewed positions, further view the returns of hedging strategies in a vacuum, rather than as a holistic part of their broader portfolio. Thus, they are likely to consider portfolio hedging programs to be a drag on their performance numbers and further undervalue them. We believe these factors, among others, contribute to a market segmentation that creates an undervaluation in tail-risk hedges.