This paper investigates the dynamics of rapid frontier development in the 40 years of Barbados' history before 1680, the decades of its transition to sugar island and slave-based “plantocracy” from a settler economy peopled by white servants and numerous small land-owners. It uses a linked data set of several thousand individuals who appeared over time in three key data sources: the 1665 export registration, the 1679 census holdings of property, and the record of deeds. Combining these sources into career histories of thousands of the people who lived in Barbados during its sugar revolution make it possible to answer some of the most intriguing questions about that economic transition. In particular, these new data shed light on the land-consolidating activities of individual landowners over time, the role of small planters and artisans in the process of land clearing and agricultural capital formation, and the participation of merchants and foreign investors in creating sugar enterprises.