The empirical study proposes a model for investigating the effect of entrepreneurial leadership on job insecurity and employee psychological wellbeing during COVID-19 based on the combined theoretical grounds of The Conservation of Resources Theory and Social Learning. To explore the job insecurity relationship with psychological wellbeing, and measure the impact of Fear of COVID-19, an empirical study was conducted on a sample of 408 employees in Croatia. The data of the cross-sectional study was collected in November and December 2020. A strong influence of job insecurity on the psychological wellbeing of employees has been identified. Furthermore, fear of COVID-19 was found to have adverse psychological effects on wellbeing. The theorized positive impact of entrepreneurial leadership on job insecurity was not supported by the evidence. The strong point of our contribution lies in the finding that the entrepreneurial leadership style alone does not buffer against job insecurity, thus pointing that the more comprehensive inquiry into other organizational factors, such as coping, learning abilities, developmental opportunities, personal disposition, and pressure bearing. The research is the first step toward enhancing our understanding of the entrepreneurial dimension of transactional psychology. The observations we recorded have implications for research into the study of the mental processes and their impact on organizational proactive behavior.