This review explores the emerging debate relating to habitual entrepreneurs. Habitual entrepreneurs (also known as experienced or, latterly, repeat entrepreneurs) are a widespread phenomenon. An entrepreneur's business ownership experience may differ according to the number of private businesses s/he has established, inherited and/or purchased. The nature of an entrepreneur's business ownership experience may not be homogeneous. Some habitual entrepreneurs may exit one private business before owning a subsequent one (i.e., serial entrepreneurs), while others may start/purchase and retain ownership of several private businesses concurrently (i.e., portfolio entrepreneurs). This review compares the profiles, behavior, and contributions of habitual entrepreneurs (i.e., serial and portfolio entrepreneurs) and novice entrepreneurs (i.e., entrepreneurs with no prior business ownership experience). The theoretical and policy cases for distinguishing between different types of entrepreneur are made. Differences between types of entrepreneur are examined in terms of their human capital profiles (e.g., education, motivations, and skills). Behavioral differences are examined with regard to the acquisition of resources, opportunity identification, pursuit and mode of exploitation, and organizational strategies. Finally, entrepreneur and firm performance differences between the different types are reviewed. Policy and practitioner implications are raised and assuming an interventionist stance, the case for targeted assistance toward habitual, serial, and portfolio and novice entrepreneurs is discussed. Avenues for additional research attention are highlighted relating to the following themes: the nature of opportunities; information search; leveraging human capital; entrepreneurial teams; measures of habitual entrepreneurship; the role of the external environment; contexts for habitual entrepreneurship; and methods and data issues.