A system and method of generating insurance risk samples and for comparing hypothetical and real insurance premiums of different insurance companies is disclosed. In some embodiments, one or more rating factors are defined and have a plurality of possible values at least partially defining an insurance risk. Values for the one or more rating factors are selected according to a predetermined distribution. The selected values are then used to generate sample risks, calculate sample premiums for the risks, and/or compare sample premiums for different types of insurance policies.