This qualitative study explores the challenges and opportunities faced by digital entrepreneurs in the context of e-commerce in Portugal. Drawing on semi-structured interviews with four entrepreneurs from different sectors, the study identifies key competencies such as creativity, resilience and personalization as essential for success. Special attention is given to gender-specific barriers, with female entrepreneurs reporting greater difficulties in accessing financing and dealing with legal and technical issues during the start-up phase. The findings also reveal strategies used to overcome these challenges, including hiring specialized professionals in marketing and technology, and leveraging digital influencers to enhance visibility. Benefits associated with e-commerce include lower operational costs and wider market reach, while risks such as payment security and product quality remain relevant concerns. The study concludes with practical recommendations for entrepreneurs and policymakers, highlighting the potential of emerging technologies such as artificial intelligence and augmented reality in shaping the future of digital entrepreneurship.