This study examines fashion entrepreneurship from the designer’s perspective. The aim is to identify what kinds of challenges fashion designers face in their simultaneous roles as designers and entrepreneurs, and what the potential advantages of that position are. The article aims to supplement existing research on micro-scale fashion design businesses that has focused primarily on the encountered challenges. A total of 16 entrepreneurial fashion designers from Finland, Estonia, and Latvia were interviewed. Thematic analysis was used in order to identify patterns in the diverse experiences of the entrepreneurial designers, and to conceptualize them into concise themes and subcategories. The purpose of the study is to bring a broader understanding of the designer’s viewpoint, and thus it highlights also personal perspectives and motivations behind fashion entrepreneurship. The results show that entrepreneurial fashion designers have to have multilevel managerial skills to run their business. Another important factor for success is the creating of balance between the business and private life. This study identifies micro-size fashion companies as businesses where creativity is a successful combination of fashion creativity and entrepreneurial creativity. Furthermore, the study shows that the obstacle for business growth might be the designer’s business orientation rather than the lack of investors. Therefore, it is crucial to recognize the different drivers behind the business, acknowledge the importance of intrinsic values (e.g. aesthetic and creative aspects), and allow them to shape the business.