How do established firms entrepreneurially leverage digital technologies for strategic renewal is an important scholarly question. This paper examines strategic entrepreneurship by two of the largest family business groups in India that have been undertaking many strategic entrepreneurial initiatives to leverage a suite of digital technologies to fundamentally reposition themselves in the emerging digital economy. It underscores strategic entrepreneurship as the primary means to exploit and shape the institutional context and achieve digital technology driven strategic renewal. It is observed that when an established firm undertakes digital strategic entrepreneurship, the strategic leadership of the firm has to simultaneously deal with two dominant logics, one rooted in legacy and the other embedded in emerging digital entity. A business group structure helps in dealing with simultaneous exploration and exploitation more effectively. The study advances a set of novel propositions on the entrepreneurial strategies of established firms that leverage digital technologies to undertake strategic entrepreneurship and contributes to the literatures of strategic entrepreneurship, business group, digital entrepreneurship, strategic leadership and strategic renewal.