The article explores the discussion aspects of the use of LegalTech tools in business in the context of the development of conceptual ideas of “smart regulation”. The relevance of this topic is determined not only by its interdisciplinary significance, the impact of technological progress, the quantitative growth of situations in which the tools in question are used in regulatory practices, and the partly experimental nature of such practices, but also by the qualitative changes in the latter, which mediate the emergence of a number of problems (both legal and moral, economic, political, technical, etc.). We are talking about both the development of new approaches to the substantive elements of regulation, their universalization, and the difficulties of applying LegalTech in certain areas in the current format of the conceptual framework of “smart regulation”—including in entrepreneurial activity. The study draws conclusions about the possible prospects for further development of LegalTech practices in the light of the conceptual transformation of “smart regulation”.