Prospects for the development of entrepreneurship in Russia as an economic phenomenon are conditioned both by objective reasons, and by socio-psychological and individual-personal readiness for entrepreneurship. Psychological analysis of the sources of productive activity is based on the highlighting of the main external function of entrepreneurship and its forms - intensive and extensive development, as well as the internal function — the management of the organization. The need for such differentiation of functions to identify the characteristics of the activities and personality of small and major entrepreneurs is discussed. Theoretical representations and empirical data on the conditions and features of the activity, psychological characteristics of small and major entrepreneurs, as well as managers of middle and higher levels of management are systematized. Innovation is acknowledged as the leading characteristic of entrepreneurs' activity, which is manifested in the emergence and implementation of new socially significant goals, new means of achieving known goals. It is noted that innovation in small and large business is characterized by different mechanisms. Large firms are characterized by entrepreneurial management, focused on organizational transformation and decision-making at all levels of complex hierarchical systems, increasing the resilience and competitive ability of the organization. Decision-making is balanced, risks are assessed and small. For small businesses, innovation is taking the form of more profound change to ensure survival and development - the risks are great and difficult to manage because of limited resources. Because of the differences, we should expect differences in individual-personality characteristics of entrepreneurs of large and small businesses, impacting the success of activities. Empirical research in an explicit form did not reveal the differences between entrepreneurs of small and large businesses, which is reflected in reality - small business today provides mainly expansion of the resources of society, the share of innovative enterprises is small, only entrepreneurs with no signs of innovation were affordable - in the fields of trade, communication and small-scale production. The results of the diagnostics of personal characteristics of entrepreneurs and managers confirmed the priority of motivation of achievement in entrepreneurs, manifested in risk-proneness; as well as revealed specifics of intelligence and communication processes, needed for the success of entrepreneurship. However, there are no reasonable grounds to abandon the idea of differentiating entrepreneurship in the form of the implementation of the function of development, as well as the search for the main determinant or systemic determinants of the internal intentions for transformative activity as the main characteristic of entrepreneurs.