This study is devoted to the issue of closing the gap between the requirements of the market of remote investment entrepreneurship and the market of higher education due to the determination and use of the legal mechanisms of their regulation. To tackle the research problem, we use several concepts, theories, and approaches, including the concept of the divide between the markets of work and university education, the theory of regulation of economic processes and digital transformation, the system of view of investment processes in view of digital transformation, and the process and system approaches. We offer a theoretical substantiation of remote investment transactions and the process of their development, perform the classification of the types of investment entrepreneurship based on remote investment transactions, analyse the value of each type of investment entrepreneurship for the market participant, characterise the multi-level structure of the legal mechanisms of regulating the remote investment transactions, identify the problems of personnel support of this market, and outline the directions for solving these problems in the context of reducing the divide between the requirements of the investment market and the capabilities of the market of higher education. The value and originality of this paper consist in the complex consideration of the problem of determination and use of the legal mechanisms of regulating the market of remote investment transactions from the position of decreasing the mismatch between its requirements and the requirements of the higher education market.