The drive for companies to digitalise and reimagine the future through new business models requires companies to create innovative cultures. There is nothing new here, it has long been recognised that companies must innovate to remain competitive in a fast changing environment. This article discusses the complexities of creating innovative cultures and provides clues as to the rare combination required in leaders who will shape these cultures – tolerance for failure, no tolerance for incompetence, willingness to experiment, highly disciplined, psychologically safe but brutally candid, collaborative but with individual accountability, flat, decisive and clear leadership.