Research on employee learning in small businesses has focused on participation in formal training. These studies find that employees get less access to training than employees in large businesses. Such studies appear to equate training with learning and convey the impression that small businesses are workplaces that provide restrictive learning environments. However, research that concentrates on a single mode of knowledge and skills acquisition overlooks much, if not most, learning. This is because most learning in workplaces takes place outside of formal training. The chapter explores the role of the owner-manager as an enabler of learning and how small business settings pose challenges for the owner-manager’s role enactment. It outlines opportunities for future research, implications for policy and practice, and the implications of contemporary developments.