The increased amounts of Internet users, emergence of new technologies that allow content digitization, create an entrepreneurial opportunity for news media to go online. However, the process of digitization has been happening at a different pace in different regions of the world. To understand the keys to success and to learn on mistakes, it is important to understand what are the factors that affect entrepreneurship and digitization of news media. The purpose of this study is to investigate the news media sector in Russia in terms of digitization of the newspaper content and entrepreneurial activities associated with this. After conducting a case study on online newspaper Novaya gazeta in Russia, authors conclude that transition economy factors have an impact on digitization of newspapers in Russia. Specifically these factors are state’s involvement in the business sector, political and economical conditions in the market and risk- averse entrepreneurs who run newspapers in transition economies.