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This paper aims at outlining the psychological underpinnings of CEOs’ financial decision-making with regard to IPO reluctance. 67 in-depth interviews were conducted within the framework of a constructivistic phenomenological analysis combined with regression and logit/probit models. The findings posit that CEOs’ stock market loathness is driven by silent herding behavior. This paper consists of the earliest empirical evidence of silent herding and therefore contributes to the enrichment of the theoretical field of behavioral finance and that of IPO decision-making. From a practical point of view, we provide policy-setters with recommendations to be implemented in investment vehicles and IPO incentives policies.