Around the world, new ventures of all sizes face the challenge of becoming as differentiated as possible while still being perceived as legitimate. Therefore, it is hardly surprising that organizational scholars and managers alike are interested in how to attain this “optimal distinctiveness.” Even after successfully obtaining funding, new ventures are known to be prone to failure during the first years of their existence, which makes attaining optimal distinctiveness particularly relevant during that period of entrepreneurial growth. To better understand this issue, this thesis investigates contextual factors that shape the relationship between optimal distinctiveness and new ventures’ performance during this organizational life cycle stage.