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The global shipping industry has been rocked by a wave of disruptive innovation driven by a thriving ecosystem of digital technology start-ups that have emerged in the last few years and set up offices in Greece. After the appearance of COVID-19, entrepreneurial leadership has grown in importance for guiding commercial shipping through times of exceptional circumstances. The problem is that there is a lack of understanding of the experiences of Greek digital entrepreneurs launching their tech start-ups within the maritime sector – from the initial vision to a real-world innovative business disruptor. We aim to answer the questions of who the Greek digital entrepreneur in the maritime sector is and how their entrepreneurial actions contribute to a growing knowledge base of digital entrepreneurship for future theoretical research and professional practice. This single-subject, archival case study demonstrates the social and commercial value of the “who” and “how” of digital entrepreneurship in the maritime sector through the case of Harbor Lab, an Athens-based start-up that disrupted the maritime industry through innovative use of emerging technologies to calculate disbursements (port expenses) and through the establishment of a horizontal, empathetic, open workplace culture. The outcomes of this study contributed a fresh perspective of scholarly knowledge on digital entrepreneurship for future theoretical research and professional practice.