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The life of an online entrepreneur is extraordinarily rewarding. In fact, so far this decade the growth of successful internet home-based businesses is an absolute phenomenon. Indeed, much discussion on forums and message boards across the internet is devoted to the topic of online businesses. Forum participants freely state their opinions about online business — the good, the bad — but rarely is the ugly discussed to any depth. Whye Noteworthy is the fact that many individuals who regularly participate in such forums are successful or relatively successful entrepreneurs. For that reason alone the majority of what they say is overwhelmingly positive. Therefore, it is safely assumed there is a “thumb on the scale” concerning the positive aspects of online entrepreneurship since those engaged in such discussions have “skin in the game”. If discussions of the day-to-day challenges online business presents became decisively negative before an audience containing potential business partners and customers, the long-term outlook for internet-based enterprises could turn quite bleak. It is, thus, necessary that all aspiring netpreneurs realize there is an inherent conflict of interest in the glowing statements online business pros make from time to time. With this thesis in mind, let’s take an “eyes wide open” review of e-commerce and consider how online business might be disadvantageous. Profitable, yet — as with most things worth doing — problematic.