Current study presents in-depth analyses of five distinct risk dimensions in relation to age, gender, country of origin and entrepreneur in family. A unique aspect of this study was repeated analyses for the same hypotheses, using data from three independent rounds of data collection. This design allowed to identify inconsistencies in in any data trends. Individuals who had an active enterprise had significantly higher scores for risk-taking propensity and profit-contingent risks, than aspiring and non-entrepreneur groups, across all these rounds of data collection. On the other hand, entrepreneurs did not have significantly different scores for risk aversion than the other two groups. A series of linear regression analyses indicated that younger males, from a developing country, and who had an entrepreneur in family, had significantly higher risk-taking propensities. Inconsistencies in results for risk-enjoyment and creative risk dimensions may be better understood through a qualitative, longitudinal research.