Technology greatly supports people’s daily lives such as education, business, medical, and many other aspects. It can be noted that the higher education institutions’ students rely on technological support and university assistance for their studies during the COVID-19 pandemic. Technological enablement is the primary determinant for entrepreneurial initiation that received attention from scholars. The focus areas include how governmental support, entrepreneurial intention, entrepreneurial education and technological enablement (mediator factor) can influence the entrepreneurial initiation. Empirical studies showed the direct and indirect impacts of the contributing factors in a particular area. However, is it the same effect of the factors for different countries? This study conducted a self-administered questionnaire to collect topic-related information from higher education institutions in Malaysia and the Philippines. A formative-reflective model, PLS-MGA, was used to analyse the direct and indirect impacts alongside the mediating factor, technological enablement. The results showed that entrepreneurial competencies, Entrepreneurial Education System, Entrepreneurial Education Mechanism, and Entrepreneurial Intention positively and significantly impact entrepreneurial success in both regions. However, the result also demonstrated that the impact of technological enablement on entrepreneurial success is more significant in Malaysia than in the Philippines. With such findings, policymakers and institutions in both countries can understand the insight and importance of technological enablement in stimulating entrepreneurship and its perceived success. Hence, they can implement supportive strategies and necessary policies to ensure technology adoption, success in shaping students’ entrepreneurial mindset and achieving the perceived outcome.