This teaching case depicts the journey of Lauren Hall – a serial technopreneur, who established five multi-million-dollar startups. The story of Lauren Hall details a series of key facets, embedded in her very own DNA, as the building blocks of a female technopreneur. It highlights how female technopreneurs could thrive amidst a range of hurdles and obstacles they confront, particularly in terms of gender-based issues, social stigmas, and a plethora of other challenges women confront in male dominated contexts. Gaining extensive insights through discussions with Lauren Hall, this teaching case portrays her resilience and tenacity that allowed her to break the ‘glass ceiling’ and steer through her journey where one could explore, (i) the traits, behaviors, and competencies necessary to become a successful tech entrepreneur, (ii) the unique challenges that female entrepreneurs face and identify capabilities and expertise needed to effectively navigate the female tech-entrepreneurial journey, (iii) the favorable role of digital technologies in providing further opportunities for disadvantaged communities, including developing countries, females and rural/regional areas and (iv) the relevant stakeholders necessary for the success of female technopreneurial ventures. The case and its teaching notes are suitable for undergraduate and postgraduate students following a contemporary information systems management course.