This paper examines portfolio entrepreneurs: those who operate more than one business at any one time. It focuses on the conditions that influence the occurrence of multiple businesses as compared with single business. Empirical evidence on the choice between portfolio entrepreneurship and a single occupation are scarce. In particular, most previous studies discuss the incidence of portfolio entrepreneurship without providing further insights into what influences the decision to engage in multiple activities. To fill this gap in the literature, our objective is to test empirically the factors that affect choice. Drawing for the first time from the historical resource of the 1881 census data for England andWales, we use a multi-level logit model to explore how employee size, farm size in acres, population density, age, gender, marital status, household size, the entrepreneurial ratio, and regional heterogeneity affect the probability of portfolio entrepreneurship. This historical resource allows a unique whole population analysis which offers opportunities, for the first time, to compare factors influencing portfolio choices between modern and past farming practices.