Between Opportunity and Uncertainty: A Process Analysis of Resource Orchestration and Strategic Responses in Portfolio Entrepreneurship

Portfolio entrepreneurship refers to entrepreneurial engagements in multiple ventures simultaneously. Distinctive managerial, organizational, and strategic practices characterize this form of entrepreneurship. In this research, I contend that portfolio entrepreneurship rests on two fundamental yet often misunderstood conditions. First, portfolio entrepreneurship represents a heterogeneous phenomenon that varies substantially across empirical instances. Second, it constitutes a dynamic entrepreneurial form that emerges and evolves over time. Consequently, a more nuanced understanding is needed of the factors that shape portfolio entrepreneurial activity and influence portfolio structure and formation. This study is guided by the following research question: How do contextual and temporal factors influence the way portfolio entrepreneurs organize and develop their venture portfolios? To address this question, I conducted multiple successive interviews with 21 portfolio entrepreneurs over a two-year period, supplemented by questionnaires, management reports, and publicly available data. In addition, I collected data on portfolio entrepreneurship within the domain of technology start-ups using Crunchbase, an industry database, yielding a dataset of 1,001 portfolio entrepreneur records. Chapter 2 provides a comprehensive overview of the scholarly literature on portfolio entrepreneurship. I propose conceptualizing portfolio entrepreneurship as an evolutionary form of entrepreneurial activity and identify gaps in current knowledge that inform a novel conceptual model outlining antecedents, determinants, and outcomes of portfolio entrepreneurship. The chapter concludes with recommendations for future research, particularly emphasizing the need for more process-oriented studies. Chapter 3 presents an empirical study examining portfolio entrepreneurs’ decisions regarding the exploration of new venture opportunities and the exploitation of existing business domains. The findings illustrate how expectations of future outcomes and the realized outcomes of past expectations shape portfolio entrepreneurs’ intentions and actions. This chapter highlights the dynamic interplay between exploration and exploitation decisions. Chapter 4 examines how resource allocation and orchestration decisions evolve over time by applying the conceptual lens of the causation–effectuation dichotomy (Sarasvathy, 2001; Read & Sarasvathy, 2005). The study demonstrates the dynamic interplay between these decision logics and shows how they shape the formation and development of venture portfolios. This research contributes to theoretical understandings of the endogenous and exogenous boundary conditions that influence resource decisions, culminating in a dynamic conceptual model of resource orchestration. Chapter 5 presents an investigation of portfolio entrepreneurship in the technology industry based on data from Crunchbase, an industry database. The study develops conceptual propositions that explain variation within portfolio entrepreneurship through the structure–agency distinction. Six domains of portfolio entrepreneurship adoption are identified, and an integrative conceptual model linking agency-related and structural factors is proposed. This model is grounded in six causal hypotheses that offer promising directions for future empirical exploration. Finally, Chapter 6 analyzes portfolio entrepreneurs’ immediate responses to an unexpected exogenous shock: the outbreak of COVID-19 in the Netherlands. By assessing extreme uncertainty and contextual severity, the study captures real-time reactions during the initial phase of the crisis. It provides unique insights into the distinctive characteristics of portfolio entrepreneurs’ responsiveness under conditions of profound uncertainty. The study identifies four factors that shape immediate responses to unexpected shocks, offering novel and relevant contributions to understanding how portfolio entrepreneurs formulate adaptive actions during unprecedented events. In conclusion, this dissertation identifies three themes that emerge across the individual studies. First, it advances our understanding of temporality in entrepreneurial decision-making, demonstrating that logics, intentions, and strategic considerations shift over time. Second, the studies illuminate multiple forces shaping the relationship between individual entrepreneurial agency and the constraining or enabling role of context. Third, they reveal distinct patterns in the formation and evolution of decisions during real-time events. These insights contribute to what I argue is a pragmatic understanding of the temporal evolution of decision-making in portfolio entrepreneurship.