As of May, 1999, 171 million people are on-line. (U.S. Commerce Report) Worldwide e-commerce sales continue to soar and are expected to reach a volume of US $1 trillion by 2003. (www.wired.com E-Biz Heavies Going Global; September 14, 1999). The Internet’s ability to reach a vast audience, coupled with the potential for staggering windfalls, has created a frenzy amongst businesses that are anxious to participate in the e-commerce industry. Ventures include small businesses looking to expand on-line, fortune 500 companies spinning off e-commerce divisions and entities investing in, or partnering, with an e-commerce company. In the rush to get on-line, however, many companies fail to develop comprehensive e-business strategies. This article highlights some key business, technical and legal issues to consider when kicking the tires of an e-commerce business.