Entrepreneurial small businesses are reckoned as agents of innovation, wealth creation and employment generation. Yet evidence from the literature indicates that small businesses often confront multi-dimensional challenges that can shrink their projected profits, impair operating efficiency, and even cause business failure or bankruptcy. The current study examines risk taking and risk management practices in two micro-sized restaurants. The research procedure follows Yin’s (1994) case method approach. Challenges facing these two firms are exemplified. An assimilation of executive and managerial thinking that reflects risk taking and risk management experiences/initiatives is presented. It is anticipated that the study will shed light on business venturing and the impact of risk management on healthy business survival. Suggestions are addressed in line with the findings.