This chapter presents two possible models of electronic marketplaces put in place at the beginning of this century, which, after their introduction, the first incoming wave of connected economy-based paradigms was ended. Both the two models show a particular use of Web-based information technology in order to exploit their mission and represent meaningful cases of application of well-defined Web strategies. Even though, at the moment, the initially built Web sites supporting those related business have been closed and merged with other Web sites, they may introduce examples of a Web strategy approach having a relevant historical meaning that may be still redefined in practical implementations once revised and adequately updated. The mentioned cases described in this chapter are usteel.com and up2gold. com, two examples of Web-based business in two well-defined supply chains, that is, the “steel” chain and the “gold and silver” chain.