Architecture is fundamental to successful product families, providing structure for sharing, and flexibility for diversity. Architectures are developed to meet the business needs and to fit with the organizational culture. Culture, structure, and flexibility are explored in the context of successes and failings in HP’s personal inkjet product families. Matching architectural structure and flexibility to a culture with tolerance for both risk and chaos leads to market winning product families. Architectural perfection is aesthetically appealing; yet balancing architectural structure, flexibility, and culture leads to more winning products.