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This chapter provides personal (auto-ethnographic) reflections on the career as a business leader in the software-development space and insights into the formation of an authentic leader. The author reviews his journey that led to running a leading video game developer at a valuation of $190 million with 1,200+ staff across 10 locations in eight countries and an array of global clients. Pohontu considers the social, economic, political and psychological elements that shaped his business methodology and discusses how he translated these into a mode of leadership. The development of foresight – a concept that emerged from the author's story – may be of interest to researchers looking to explore diverse leader contexts through theoretical lenses to achieve a greater understanding.