This article consists of a comparative study of approaches to crypto-assets in the USA and EU, as well as an exploration of the reasons behind such differences. These two jurisdictions vary dramatically in their history, economy and legal systems. Therefore, differences in legal regulation regarding the Initial Coin Offering are to be expected. Doctrinal comparisons of legal regulation rarely shed light on the way that law actually operates, but are necessary to answer the question of why countries do not enact similar approaches to the regulation of the Initial Coin Offering. This leads to the conclusion that, in both jurisdictions, there exists no legal certainty. Meanwhile, the failure of either the United States or the European Union to regulate the crypto-assets market effectively will have spill over effects for other jurisdictions. There is, therefore, an urgent need for strengthening international standards in the regulation of crypto assets. Therefore, this article intends to contribute to the search for a necessary, appropriate, and transnational way to chart the contemporary legal landscape of Initial Coin Offerings. The most favourable form of legal convergence regarding the Initial Coin Offering should provide increased legal certainty while protecting consumers and fostering substantial investment in innovation.