This chapter examines the specifics of entrepreneurial mindset of owners of small- and medium-sized enterprises (SMEs), who operate their business in an unfavorable environment, under an emerging market economy based on the examples of the Republic of Moldova. Taking into account specific examples, it is demonstrated that in Moldavian economy, business strategies based on entrepreneurial mindset (i.e., those aimed at increasing competitiveness, using innovative approaches focused on development of the human capital, organizational change, and cooperation) represent an important factor in the preservation and development of SMEs. At the same time, the hypothesis is presented according to which the implementation of some original business strategies, also oriented toward the development of the enterprise and which take into account the specific features of a particular business and the general situation in the country, can contribute to the growth of enterprises only in an unfriendly environment. Accordingly, in long term in conditions of improvement of the business ecosystem and increase of the standards of living of the population, such business strategies will not motivate, but on the contrary, limit business development, especially in the long run. The presented ideas and conclusions are based predominantly on the results of interviews with Moldavian entrepreneurs carried out in recent years with the participation of authors.