There is a clear gap in the literature, comparing entrepreneurship in urban and rural areas and analysing distinct differences between them, impacting their survival and growth. A case study approach was adopted, with six cases on urban and rural Scottish enterprises. This study aims to find the motivations and classifications of success for urban and rural entrepreneurs. These contrasting motivations and conceptions of success have been linked to the way companies strategise. Our findings contribute to the literature by adding an understanding of the motivations of entrepreneurs in rural and urban businesses, respectively. Further, the study was conducted in Scotland, which adds a further understanding of the motivations of entrepreneurs within the country specifically, which can be used in further research within the country.