Although research indicates that the export channel a firm uses can significantly impact export performance, it is unclear how firms should select this channel. Models of export channel choice tend to concentrate on transaction cost efficiencies, ignoring value adding orientations that entrepreneurial firms may possess. In this paper we develop and test the theoretical notion that in addition to transaction costs, differences in entrepreneurial orientation (EO) influence export channel choice and as a consequence export performance. Using data from a sample of Dutch and Italian SMEs we find that adding EO (moderated by institutional distance) significantly improves our model of export channel choice. Further we find that firms selecting export channels that align not only with transaction cost factors but also firm level EO, moderated by institutional distance, have higher export market performance. Thus, our study adds to and extends the export channel choice literature and provides interesting new insights into how EO helps firms create more successful export operations.