Both biological and cultural evolution are delineated by dual, ongoing processes of differentiation and integration. Companies labeled as Firms of Endearment whose social consciousness blurs the distinction between for-profit and not-for-profit sectors, represent the positive deviants of evolution among organizations. The ongoing process of evolution creates non-zero-sum relationships that enable sustained organizational success while cultivating the flourishing of all stakeholders. By exploring the positive psychology and positive organizational scholarship research that can illuminate the mechanisms behind the success of these positive deviants, organizations can learn to evolve themselves through a process of differentiation and integration, while overcoming the trust and communication barriers to such progress.