Small business success is key to economic growth in South Africa. Unfortunately more than 70% of start-up companies fail within the first five to seven years of inception. There needs to be a greater focus on the small business owner and their psychological decision making behaviour. The purpose of this study was to firstly, examine the relationship between life-goal orientation (extrinsic motivation, intrinsic motivation and impersonal) and financial risk propensity of small business owners. Secondly, to examine if stakeholder empathy is a mediator in the relationship between life-goal orientation and financial risk propensity and lastly, to examine the relationship between stakeholder empathy and life-goal orientation. Data was collected from 123 respondents through a survey. Correlation and regression analysis were performed in order to examine the hypotheses. The study did not find a relationship between life-goal orientation and financial risk propensity for this sample and therefore, no mediating role for stakeholder empathy could be examined. The results indicated a correlation between stakeholder empathy and intrinsic motivation, as well as stakeholder empathy and impersonal life-goal orientation. However, no correlation was found between stakeholder empathy and extrinsic motivation. The findings of this study emphasise the importance of context, demographics and environment of respondents when testing financial risk propensity, life-goal orientation and stakeholder empathy. The findings also suggests small business owners are generally more intrinsically motivated and empathetic towards stakeholders, which can have positive and negative effects on the performance of their company.