An entrepreneurial venture is an engagement process that involves “high” and “low” periods. The question of how this motivation evolves, and the underlying issue of loss of motivation (which we refer to as a “period of doubt”) an entrepreneur may experience right from start-up deserves further investigation. Mentoring, with the moral support, encouragement, advice and knowledge sharing it provides, is likely to help novice entrepreneurs recover the motivation they need after a career change and continue developing their business. This study focuses about the effect of mentoring on reducing entrepreneur doubt, and about the relevant mentoring parameters to consider in order to maximize doubt reduction among entrepreneurs.