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Throughout centuries, Latin America has faced a paradox. On one hand, the abundance of resources has attracted immigrants who find a suitable place to undertake profitable business ventures in the region. On the other hand, the limited entrepreneurial resources of most countries of the region have motivated the migration of talented people, among them entrepreneurs, to non-Latin American countries. This chapter explores this paradox through the analysis of entrepreneurs' motivations to immigrate to, and migrate from Latin America, the influence of their profile on their business ventures, as well as the role played by both the home and the host countries' institutional conditions. The findings of this analysis underline the diversity of migrant entrepreneurs in terms of personal resources and survival versus opportunity-driven migration decisions. They also reveal the kind of mechanisms migrant entrepreneurs use to counteract their host country's institutional challenges.