This study examines the constructs of entrepreneurial orientation (EO) versus small business orientation (SBO), their impact on small business performance, and whether these effects are moderated by longevity. A sample of 267 small business owners from 11 small–medium downtowns was used in structural equation modeling (SEM) testing of the measurement, structural and moderation hypotheses. The measurement confirmatory factor analyses models of the two constructs revealed that EO and SBO are unique constructs. Then a structural model predicting performance was tested. Finally, a two-group model split on “below 11 years” versus “11+ years” demonstrated that the structural paths connecting EO and SBO to performance are not the same in these groups: for the younger group, only EO significantly predicts performance while for the older group, only SBO significantly predicts performance.