This article examines the activities of two early European explorers, Christopher Columbus and Henry the Navigator, in light of modern theories on entrepreneurship. These were Schumpeter‐type entrepreneurs who revolutionised the world of trade and commerce. Their eventual success was the result of a number of factors including technology, access to capital, access to information, their skill‐base, social/motivational factors and luck. All of these factors, in turn, were determined by their environment. Their reliance on knowledge and technology show these entrepreneurs as being one stage in a technological trajectory and growth of knowledge. This stage represented a major threshold in which a window of opportunity was opened. This illustrates a process of environmental selection whereby entrepreneurial success is determined by changes in the environment.