The study aimed to identify the problems that are associated with starting and running small business enterprise in Nigeria, in comparison with Swedish small business enterprises and determine the ranking of these problems. In caring out the study, a qualitative research method was used. The most important method data was sourced by primary data using interviews, utilizing a questionnaire and by secondary data using literatures collected from books, journals, past research work and electronic web. The researchers also used purposive sampling technique to select some of the top ranking personnel in Premier Bakeries, Booms Nig, Café Master Hans and Marianne Bageri. The analytical strategy used was in relying on theoretical propositions. On the basis of the analysis of data collected during the interview, the study revealed that small business managers in developing countries such Nigeria face many problems when compared with developed country like Sweden. The problem facing Nigerian small business managers are ranked as follows: lack of finance in starting and developing business, poor infrastructures, inappropriate legislation, competition, lack of managerial skills; further problems are corruption and inflation. Small business managers in Sweden are face with the problems of high increase of work absente due to cases of sicknesses by personnel and the effect of the weather on business. The study concluded with some recommendations on the need of the developing countries to emulate from developed nations in creating enabling environment that will promote and sustain the growth and development of small businesses.