Portfolio entrepreneurs, a sub-type of habitual entrepreneurs are involved in a number of businesses simultaneously. This study explores why and how some individuals become portfolio entrepreneurs. Fifteen cases of portfolio entrepreneurs were selected and interviewed in- depth. Results show that portfolio entrepreneurs do have a distinct combination of human and social capital endowments, motivation and risk propensity. These antecedents allow them to formulate strategies that pave the way to portfolio development. While the reasons for the pursuit of the portfolio model vary across the different portfolios, it is evident that the portfolio is a result of the entrepreneur s opportunity and growth-seeking pursuits and a way to spread the risk inherent in business. The study reports strategies and heuristics that these entrepreneurs employ to manage the dynamics of a portfolio structure. At the business level, outcomes indicate that individual businesses benefit from being part ofa larger portfolio. On a personal level, successful portfolio entrepreneurs do become high net worth individuals.