This chapter introduces the concept of SWOT analysis as one of the most critical tools for strategic decisions. Instead of relying on the manager’s intuition, strategic decisions should come from systematic analysis that takes into account the internal and external conditions of an organization. The core content in this chapter pertains to each dimension of SWOT analysis: strength, weakness, opportunity, or threat. In particular, the explanation of the SWOT model is embedded in the context of a technology entrepreneur’s early decision stage—whether they should embark on a new venture. Some observations regarding common SWOT of technology ventures are offered. Lastly, bias interpretations of SWOT analysis are raised as lessons.