International trade is vital to a country’s economic survival (Al-Aali, 1995; Asiedu & Lien, 2004). Currently, exporting represents one of the most common international trade activities and entry modes to international markets. Multinational-enterprises (MNEs) have enacted a dominant role in global markets for a substantial time. However, more recently, small and medium-seized enterprises (SMEs) have come to play an increasingly important role in the global economy. In fact, SMEs have been reported to contribute between 25 to 35 percent of world exports (Chen, 2006) and manufacturing, thus, emphasising their importance in the global marketplace. This being the case, significant research attention in the area of SMEs and their exporting performance, international activities and barriers to new market entry has resulted. However, little attention has been given to the decision-making processes associated with exporting (Anderson & Floren, 2004). Moreover, little is known about SME decision-makers and, in particular, the level of perceived risk they associate with international business activities. This represents a significant gap in the literature. Given this, there is a need to understand how individual characteristics (for example demographic characteristics and management style) and cultural characteristics (for example uncertainty avoidance and long-term orientation) together with exporting motivations and barriers influence SMEs decision-makers’ risk perception associated with exporting and how these may differ within emerging and advanced markets. In doing so, important theoretical and practical implications will result.