This paper addresses the self-representation of Jewish merchants in the Mediterranean area during the eighteenth century, a time in which commercial society ostensibly became more tolerant and open. Research on Sephardic merchants has emphasized the facility with which they participated in wider European commerce. Still, Mediterranean Jewish merchants continued trading with other Jews too, and remained anxious about their intra-Jewish reputation. Issues of self-representation were urgent since many young Jewish apprentices grew up, as men and merchants, away from their households of origin and the supervision of their fathers. How was reputation built and protected once young men left home, and what values were key for a Jewish merchant’s self-representation? The bulk of my evidence comes from the 1776-1790 correspondence of Tunis-based, Italian Jewish merchant Joseph Franchetti, supplemented by comparable cases and contextualized within the tradition of merchant advice literature. Approximately 20% of Franchetti’s 360 letters were addressed to his sons and young brother-in-law in Livorno and Smyrna, thus illuminating his strategies of education and control, which prudential values he stressed, as well as specific anxieties about his own and his sons’ reputation. I will address mercantile self-definition by looking at pedagogical practices, ideals of commercial masculinity, views of intra-Jewish difference, and worries about Christian perceptions. We will also see how, even at a time in which attitudes to trade allegedly became more secular and cosmopolitan, discourse about Judaism and Jewish bonds of allegiance retained a critical role both in the self-representation and in the practices of Mediterranean merchants.