This chapter investigates Moscow’s traits as a cosmopolitan city. When transition to a market economy began in 1992, Moscow quickly transformed itself in a megapolis receptive to all kinds of business ideas, with booming entrepreneurship. In recent years, since 2014, Moscow’s fast-growing cosmopolitanism has been challenged by more inward orientation that the city adopted due to Western economic and political sanctions imposed on Russia. The chapter elucidates the structure of Moscow’s economy, which shows the city’s cosmopolitan nature. However, entrepreneurship is impeded by the difficulties related to borrowing for business development. The chapter also identifies certain controversies related to how various ethnic communities engage in entrepreneurship in Moscow. This is followed by highlights of recent changes in the rules of doing business implemented by the city government. In addition, the chapter analyses the details of Moscow’s Skolkovo project aimed at enhancing globalisation by bringing large-scale investment and innovation and outlines the project’s results to date. To become more cosmopolitan, the city’s governance needs to overcome its inward orientation by approaching new partners, both domestic and international.