This paper examines how founding conditions shape subsequent organizational evolution— specifically, the proliferation of management and administrative jobs. Analyzing quantitative and qualitative information on a sample of young technology start-ups in California’s Silicon Valley, we examine the enduring imprint of two aspects of firms’ founding conditions: the employment blueprints espoused by founders in creating new enterprises; and the social capital that existed among key early members of the firm—their social composition and social relations. We find that the initial gender mix in start-ups and the blueprint espoused by the founder influence the extent of managerial intensity that develops over time. In particular, firms whose founders espoused a bureaucratic model from the outset subsequently grew more administratively intense than otherwise-similar companies, particularly companies whose founders had initially championed a “commitment” model. Also, firms with a higher representation of women within the first year subsequently were slower to bureaucratize than otherwise-similar firms with a predominance of males. Our analyses thus provide compelling evidence of parth-dependence in the evolution of path-dependence in the evolution of organizational structures and underscore the importance of the “logics of organizing” that founders bring to new enterprises. Implications of these results for organizational theory and research are discussed.