Underwriting process is the core function of property/liability insurance companies. An appropriate underwriting policy can avoid adverse selection and make sure that insurance companies select only those insured whose actual loss will not exceed the expected loss. This study attempts to connect the culture theory of risk, risk perception with underwriting performance of underwriters in property/liability insurance companies. This study explores the effects of different types of worldviews upon the underwriting performance and evaluates various underwriters’ financial risk perception based on different worldview by use of conjoint expected risk model. Interesting and fascinated empirical evidence could be found that risk perceptions represent a considerable part on underwriting process, which has not been found yet in previous finance or insurance literature.