Passport sales programmes have concentrated in island microstates. This paper analyses organisational factors and strategic management leading to comparative success or failure of these economic citizenship programmes. Each passport sales business in the Pacific islands has had a brief life—the majority continuing for a few years, at most. They evolved within a precarious and disorderly environment—frequently with a fast ascent, before they crashed. Collapse has often been followed by similar short-lived schemes in the same Pacific island country. Yet other passport sales enterprises in Caribbean and European island microstates endure and even thrive. The comparative success or failure of passport sales ventures around the world depends significantly on how they are organised. This paper outlines similarities in the organisational styles of the Pacific island programs—as isolates. In examining programmes elsewhere in small island states in Europe and the Caribbean, it analyses the types of organisations that are more likely to lead to a more enduring success—foreign professional agencies and subcultures.