Youth Business International (YBI) has helped a significant number of young entrepreneurs through its network of business programmes worldwide. It provides young people, who have little more than a bright idea and the determination to succeed, with a start-up loan and the services of a volunteer mentor. However, what is less well known is the true nature of the mentor-client relationship and the impact this has on a young person’s personal and business success. This study takes as its sample two distinct groups of mentors, young entrepreneurs and programme managers from two different countries and using a case study method explores what leads to success. The emerging themes show the nature of the relationship is affected at three critical phases: start-up, midpoint and endpoint. The results also show that mentors are required to use an approach towards entrepreneurs that reduces dependency and increases self-confidence. The findings indicate a style of mentoring which is less directive and more empowering as the client’s business starts to grow.