The central focus of this study is an examination of the entrepreneurial activities of James Reddy Clendon, an English sea captain, merchant and settler who rose to prominence in the Bay of Islands during the period 1830 to 1840. The study initially asks three basic questions: Why did Clendon come into the Pacific to trade? Why did he choose to settle in New Zealand? How did he survive in the years prior to and immediately after British annexation? This study is important as there are few comprehensive studies that examine the period of European settlement in Northland between the 1820s and 1840s in New Zealand's history. Such a study is intended to act as a lens through which a number of wider issues in New Zealand history can be examined. These include: the commercial relationship between Australia and New Zealand prior to 1840; interaction between Maori and European traders in commerce; the role of entrepreneurs in the declaration of formal British authority in New Zealand; the role of the entrepreneur in European settlement, including issues of class and status among New Zealand's earliest settlers; and the effect of British annexation on existing European settlers in northern New Zealand.