The purpose of this chapter was to analyze international and cultural aspects that academic entrepreneurs must take into consideration to support or hinder academic entrepreneurship. We elaborated on international and cultural aspects to be taken into consideration to successfully undertake an academic entrepreneurship journey, such as cultural, administrative, geographical, and economic distance. We deepened our understanding of cultural distance by summarizing the most used sociological approaches. Finally, we discussed the personal and institutional factors that can support or hinder entrepreneurship success, such as cultural sensitivity, cultural awareness, and the concept of academic learning organizations.