The Italian entrepreneur Brunello Cucinelli has spent decades building a successful eponymous international clothing brand from the small Umbrian hamlet of Solomeo. What is perhaps less well known is the degree to which his business ethics are informed by the long history of Western humanistic philosophy. Given that Cucinelli recently received an honorary doctorate in Philosophy and the Ethics of Human Relations from the University of Perugia, and around that time saw annual sales exceed two hundred million dollars, there is an increasing mandate to explore whether or to what extent Cucinelli’s investment in the humanistic tradition contributes positively to his success as an entrepreneur. Is philosophy profitable? Do ethical business practices translate into better products, enhanced employee well-being, and greater fiscal returns? Not only is it worth replying to such questions with a narrow focus on Cucinelli’s business, it is of considerable interest how his methodology—including bold philanthropic initiatives based on humanistic principles—may usefully inform the wider dialogue on business ethics, and whether his results can be meaningfully replicated in other locations and types of industry