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Literature has recognised entrepreneurship education as the main conduit through which entrepreneurial behaviours, attitudes and actions can be built, enacted and delivered. Since the founding of new ventures is largely a resourceful founder-driven enterprise, entrepreneurship education has largely centred on galvanising and shifting the mindsets and cognition of the entrepreneur. Yet, despite over 60 years of delivering entrepreneurship education programmes, hard evidence of the generation of high-growth-oriented and sustainable ventures has been scarce as student entrepreneurship intentions do not always translate into successful venture creation. This is largely because of the complexities of the practicality of entrepreneurial education particularly, the dissonance between acquired education in business schools and the knowledge and competencies needed in the entrepreneurial field. Such dissonance can be attributed to the lack of clarity on the pedagogical approach that most resonates with entrepreneurial action, the diversity in assessment methods and the scholarly illusion pertaining to how pedagogical approaches can be channelled to the generation of growth-oriented ventures. Drawing on Girox's concepts of transformative critical pedagogy (including pedagogy of repression), Socratic dialogue, Hegelian dialectic and Yrjö Engeström's transformative expansive agency, I demonstrate how a flipped transformative critical pedagogy can be harnessed in digitally enhanced learning environments to create new entrepreneurial possibilities for facilitating critical inquiry, complex problem-solving, innovation for the market and fostering tolerance for failure in ambiguous entrepreneurial contexts.