Between 27% and 46% of small and medium enterprises that successfully scale revert to their prior operational size within three years, a rate that is structurally amplified in vehicle-based businesses where capital is concentrated in depreciating physical assets and competitive differentiation occurs primarily on price and service reliability rather than product innovation. This article examines the conditions under which entrepreneurial management functions as a genuine strategic asset in small and medium vehicle-based businesses, rather than as a dispositional attribute of owner-managers that is orthogonal to firm performance. The analysis identifies a systematic misfit between the dominant theoretical frameworks, specifically dynamic capabilities theory and the five-dimension entrepreneurial orientation model, and the operational context of vehicle-based SMEs. Drawing on a critical synthesis of 13 empirical and theoretical sources, the article argues that dynamic capabilities yield measurable performance returns only under conditions of high environmental dynamism, a threshold that asset-intensive transport markets do not reach, and that the entrepreneurial orientation-performance relationship in this sector is mediated by competitive positioning through contractual and regulatory foresight rather than by innovativeness or risk-taking. Three sector-specific mechanisms are identified through which entrepreneurial management converts into competitive advantage: the institutionalization of operationally scripted routines that free management bandwidth for strategic positioning decisions; proactive regulatory compliance that generates first-mover advantages in fleet certification and route licensing; and the development of decision-support infrastructure that enables analytically grounded fleet renewal and platform coopetition choices. The article concludes that the standard EO measurement instrument requires sector-specific reweighting before it can reliably predict performance outcomes in vehicle-based SMEs, and that longitudinal firm-level data from commercial transport markets represent the most tractable foundation for that instrument's development.