This study investigates the UK former family firm, Whitbread, and its transformation from traditional brewer to leading leisure retailer comprising two main business lines, Costa Coffee and Premier Inn hotels. An unexpected regulatory intervention in 1989 all but ended the centuries-old vertically integrated model of the UK brewing industry, of which Whitbread was an important member. The major brewers were challenged to find alternative business models and growth trajectories. In the subsequent structural and organizational change of the 1990s and 2000s, Whitbread was the only original brewery group name to survive in the public domain as the others disappeared in industry-wide consolidation. Few observers would have anticipated Whitbread’s endurance, let alone the nature of the Whitbread that emerged from this process. As important to the narrative of a 250-year family legacy founded on socially conscious entrepreneurship and financial prudence, is a rare ability to respond and adapt to changing institutional conditions through continuous experimentation and innovation set against the backdrop of an industry constrained by the dominant logic of maker rather than seller.