Purpose Amid China's “Digital China” agenda and mixed findings largely drawn from large firms and digital-native startups, we ground the study in the essence of entrepreneurial innovation (EI) as the fusion of creative innovation and entrepreneurial behavior. We therefore examine ChiNext-listed small and medium-sized enterprises, which best match this nature, to assess whether, how and under what conditions digital transformation (DT) influences EI. We further analyze how these effects vary with internal organizational behavior and management as well as external financing forces in order to clarify mechanisms and boundary conditions and to inform policy and practice. Design/methodology/approach We develop a context-centered framework to test how DT shapes EI across industry, organizational and social settings, drawing on principal–agent and cognitive theories. Using ChiNext-listed SMEs (2010–2023), we construct NLP-based DT and myopia measures from annual reports, combine them with financial and governance data and estimate firm- and year-fixed-effects panels to test main effects, mediations and venture capital (VC) moderation. Findings DT lifts EI among ChiNext-listed SMEs, but gains vary by ownership, life cycle, and region. Value arises via governance: equity-based incentives mediate positively, while managerial myopia mediates negatively. VC has a dual, path-dependent role: it amplifies DT’s effect yet can suppress EI, dampen incentives and heighten myopia. Managers should tailor DT and incentives to context, strengthen absorptive capacity and engage long-term-oriented investors so DT translates into sustained, innovation-led performance. Originality/value Rather than correcting sample bias, we target the DT–EI relationship at its natural locus by aligning the inquiry with EI’s essence and focusing on ChiNext-listed SMEs. We integrate a context-based framework with firm-level governance, identify managerial incentives myopia as internal channels and show heterogeneous moderation by VC, delivering rigorous, replicable evidence and actionable guidance for SME governance in digital markets.