Purpose:The aim of our research is to deeply analyze entrepreneurial dynamics across generations X, Y, and Z, enhancing understanding of generational shifts and offering insights for future tailored entrepreneurship policies and development programs. This study serves as a foundation for stakeholders to address the unique challenges and opportunities presented by each generational cohort. Design/Methodology/Approach: In our paper, we conduct a nuanced comparative analysis of entrepreneurs from Generation X, Y, and Z within a semi-peripheral European Union member state, employing Ridge, Lasso, and Elastic Net regression techniques. Utilizing a sophisticated system-level approach, we devised a quint-segment model capable of encapsulating the generational disparities in a comprehensive manner. Findings: Our findings delineate a pronounced polarization within the sector, highlighting a notable intergenerational coexistence particularly between Generations Y and Z. Despite the distinct socio-economic backgrounds and entrepreneurial approaches prevalent amongst these generational cohorts, there emerges a remarkable alignment in self-perception and economic trust between Generation Y and Z entrepreneurs. Conversely, this shared perspective markedly diverges from that held by Generation X individuals, spotlighting a significant generational schism in the appraisal of the business environment and the evolving role of education and training across these generations. Practical Implications: In light of emergent entrepreneurial paradigms, it is imperative for policymakers and educational institutions to recalibrate, cognizant of Generations Y and Z's proclivity for informal pedagogical modalities and networking. Business support mechanisms, notably incubators, are enjoined to refine their approaches, accentuating Gen Z's predilection for trust-anchored mentorship. Concurrently, investors and governmental entities must reconfigure strategies, attentive to dynamic sectoral and capital sourcing shifts. As workplace ethos undergoes transformation, enterprises should champion inclusivity, with advisory services emphasizing bespoke, trust-centric advisement. Originality/Value: The paper presents a novel systemic analysis of entrepreneurial dynamics across generations offering fresh insights particularly on the economic and self-perception dimensions of Generations Y and Z in juxtaposition with Generation X. Through a quintsegment model and five predictive models, the study not only corroborates existing literature but also unveils unique intergenerational discrepancies and convergences, thereby enriching