Diaspora entrepreneurs contribute to regional development through business, ideas and resources. Most diasporas originate from migration from developing and emerging economies and are captured in dyadic patterns between the country of origin and their residence. Understudied are diaspora entrepreneurs migrating ‘against the tide’ by selecting atypical destination region(s). This qualitative study examines the migratory paths of Jewish diaspora entrepreneurs departing from their communities and planting seeds at new locations for their communities to follow – in other words, leaving their communities behind physically, not mentally. Findings advance a theoretical understanding of diasporic entrepreneurial types, contexts and the dynamic interplay between pioneering entrepreneur(s), their community and their location.