Adopting an intersectional lens, this book comparatively examines the multiple processes and systems of power that frame the experiences of female entrepreneurs in the Caribbean and the fluid ways in which they respond to these. Specifically, it challenges entrepreneurial scholars who are concerned with the experiences of women within that sector to critically interrogate interlocking structures of power (e.g. gender, race, class, age, industry-based hierarchies) that operate within that space, the marginalizing effects of related processes, and the extent to which these affect their thinking and practices of female entrepreneurs within the region. Through comparative lenses, the book highlights the structural and relational realities and complexities that undergird the entrepreneurial landscape within the region, the effects of these on the entrepreneurial identities, positionalities, and practices of female entrepreneurs. It underscores the many ways in which they navigate that terrain. In so doing, the book offers critical insights into the historical, socio-cultural and economic parameters within which female entrepreneurs in the region engage, the lived realities associated with these, the prospects or possibilities for re-presenting or re-framing such contextual and discursive spaces. It also provides necessary understandings of the motivations, positions, prospects, possibilities and constrains of entrepreneurial women in the region and the policy implications of these realities. This book offers insights for scholars and policymakers that are important for (i) understanding the current gaps in entrepreneurial research and policy, (ii) the tools, methods, and strategies that are needed to address these contextual and discursive realities, and ultimately, (iii) the ways in which policy makers and local governments can promote the authentic empowerment of female entrepreneurs in the region, while giving considerations to precarious realities of women.