Angel Investors and Venture Capitalists often come across at different points in the venture capital industry. Albeit they follow analogue goals and a related approach to investing, they do not seem to get along very well. Concomitantly, in recent years a substantial change has occurred in the venture capital market leading to an increased competition between them. Indeed, strides are being made to develop a closer relationship. This study is an attempt to cross the chasm of misalignment between what Venture Capitalists and Business Angels really want and what they are actually able to provide. An analysis with interviews has proven that there is a considerable degree of interconnectedness between both groups. An often cited issue is the sophistication and professionalism of Angels, which is actually on the rise but which has to be further promoted to harness the potential for mutual economic success. Besides, various models of co-operation and complementarities exist on the association as well as the investment level. Far beyond doubt, the foundation is there to create a symbiotic relationship and to build viable innovative businesses by fuelling entrepreneurial activity together.