The digital environment and the businesses can no longer exist separately; the way in which entrepreneurs adapt to digital environments determines the future of the companies. By aiming to understand Romanian entrepreneurs’ openness and the assets disposed for digitalisation, the authors performed a study which revealed different managerial approaches used in order to achieve digital entrepreneurial sustainability. With exploratory research, they (i) identified the strategic approaches of the businesses within the digital environment, (ii) analysed the importance of strategic objectives and the entrepreneurial vision, (iii) understood the long-term strategies and the costs of digitalisation, and (iv) analysed the future of the business in terms of cyber security. The study highlighted that no Romanian entrepreneur placed digitalisation as an independent objective for its company, showing that companies needed a proper digitalisation strategy correlated to the opportunities and threats of the business environment. Moreover, the Romanian entrepreneurs’ knowledge in cyber security was low even though they were aware that it was imperative to control critical information and develop data security strategy so as to avoid data theft/loss in the company. All the findings favoured conceptualising a new Digital Sustainable Entrepreneurship Model based on owners’ entrepreneurial visions and companies’ strategic objectives alike, a guide-framework to remain competitive in a sustainable, ever-growing market.