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This chapter assists in Iran’s start-ups swift internationalisation from the onset. Indeed, it sheds in-depth qualitative and quantitative insights into analysing the propelling factors towards entrepreneurial internationalisation. To accomplish this feat, a mixed method of Systematic Literature Review (SLR), Fuzzy-Delphi (FD) and Fuzzy-DEMATEL (Decision Making Trial and Evaluation Laboratory) – ISM (Interpretive Structural Modelling) – MICMAC (Matrix-based Multiplication Applied to a Classification) (FDIM), along with a multi-scenario analysis have innovatively been applied. As a result, entrepreneur characteristics and an accessible qualified workforce, even in foreign countries, are the most prominent drivers. Most probably, the institutional voids, interconnected benchmarking and the advent of new disruptive technologies form the independent factors which can sharply influence the whole system, particularly the entrepreneur characteristics as a dependent one. Moreover, social media, customer orientation and the domestic market cover autonomous drivers, which can moderately be affected or influence the abovementioned factors.