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We provide a structural equation model to analyze the influence of both willingness to trust others and personality factors such as the Big Five characteristics and optimism on retail investors’ risky assets share and general willingness to take risks. The main findings are as follows: The personality trait agreeableness has a significant and positive impact on general willingness to trust. Willingness to trust others has a significant negative influence on the willingness to take financial risk. More neurotic and more conscientious individuals are significantly more risk averse. Furthermore, more optimistic people reveal a significant lower degree of risk aversion.