Many companies today face the need to embark on a dual transformation: Reinventing and sustaining their core business while concurrently creating new, future businesses. This case about Globe Telecom, Inc., in the Philippines presents the s.tory of just such a transformation The case is bookended by the CEO’s 14-year tenure and describes successive waves of reviving and retooling the once-flagging telecom business. It is situated in a transient, highly competitive B2C landscape, continually susceptible to the forces of saturation and commodification. The thread connecting Globe’s successive reinventions is the CEO’s belief in the company’s “unfair advantage” when building new businesses in telco space adjacencies. The project of building this advantage – and the attendant pursuit of new opportunities, sectors and partnerships – has had to be constantly balanced with the ongoing task of growing market share in the core mobile business. Underlying both sets of activities is the rediscovery, at regular intervals, of Globe’s purpose as a corporation, a consumer player, an employer and an important stakeholder in the emerging and fast-growing domestic economy, as well a broader sense of being an agent of development for the nation. Managing these intricate processes requires not only foresight from the company’s top leadership but also the presence of ambidextrous talent – a workforce that is up to the task of optimizing for today while transforming for tomorrow. Historically, organizations have separated these two tasks in terms of talent, budgets and reporting lines. The case showcases flesh-and-blood individual managers and their observations on the dual challenge of running this business at the same time as building the next businesses.