The paper is devoted to the study of the contradictions in the entrepreneurship development in modern socio-economic conditions of the Russian Federation, therefore the paper does not discuss those contradictions that constitute the nature of entrepreneurship and are common to all countries. First of all, we conducted a bibliometric publications’ analysis in the Russian scientific database eLibrary on the entrepreneurship development contradictions, determined the number of publications’ dynamics and the most cited ones. After that, a statistical analysis of data on the small businesses development in Russia was carried out in the period from 2019, which is a relatively economically calm pre-pandemic period, to August 2023. The analysis showed that Russian small businesses recovered from the shock of 2020 and continued to develop, and labour productivity also increased. Next, two contradictions were explored in detail: between the proclaimed core modern value of entrepreneurship and the historically felt core traditional values; between the large amount of energy requirement in developing a small business, which is more typical for young entrepreneurs, and the successful startups of pensioners over 60.