The thesis of the paper is this chapter is that to play an active entrepreneurial role in e- commerce, professionals need to develop holistic understanding of e-business issues, ‘business imagination’ skills of ‘creative win-win design’ and negotiation skills. In the first part of the paper the author discusses the e-business situation pointing at great opportunities, and often not so great practices. The second part presents a proposed ‘portal model’ for understanding e-business as a way to overcome the compartmentalisation of management disciplines. The third part shows the importances of negotiation skills, which, for the purpose of this paper are understood primarily as an ability to design solutions that are beneficial for all parties involved and create timely strategic alliances. The practical importance of those skills is shown in several cases. Among others, how negotiation mastery (not technical genius) of its founder enabled creation of the arguably the most successful corporation of our times. Finally, implications from management training and business education are discussed. Results of unpublished research (conducted with 124 groups) that show the limitations of verbal, cognitive education are presented. Consequently a holistic approach, which would include both classical “cognitive” and “emotional” intelligence as well as further research into the matter, is recommended.