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The chapter focuses on brand image and its role in business relationship initiation. The chapter takes the perspective of personal brands, CEO branding in particular, and discusses how brand image of the CEO affects the establishment of new relationships. The corporate brand image provides a first insight into, for instance, perceived quality, while the CEO brand is a strategic combination of the CEO image and CEO reputation. An empirical case study exemplifies and illustrates how the corporate brand and the CEO brand interlink. The reader learns that a strong CEO brand may outperform the corporate brand in the initial stage of establishing new business relationships. Trust and commitment are highlighted through the case, inducing that business relationship performance is dependent on personal interaction and network bonds between the actors. The personal brand of the CEO is an important element in branding strategies and a strategic tool for organizations active in the B2B domain. This relates specially to partner selection and the stage of initiating business relationships. Furthermore, both rational and emotional factors are considered when business partners evaluate each other, in search for information and cues as regards the history of the partner. Eventually, trust is created between the partners, and the relationship is initiated.