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How aggressively should an incumbent move when developing an online business that threatens its core product? With Internet competitors taking direct aim at the traditional print newspaper business model, the Boston Globe fought back with its own web initiative, Boston.com. Globe and Boston.com managers face decisions regarding whether and how to cross-sell print and online classified advertising; how to roll out online auctions; whether to integrate print and online editorial staff; and the pros and cons of issuing a tracking stock for the Internet businesses of the New York Time Company (the Globe's parent company). At a broader level, the case raises the question: Are old media companies doomed as the new economy dawns? It introduces the terms "hawk" vs. "dove" to describe businesses that enter the online arena by establishing wholly separate online divisions versus closely coordinating their online and "offline" activities. The case asks: Can employees trained in the traditional business shift to new, digital ways of thinking? Are legacy systems advantages or disadvantages given the need for Internet speed? Finally, what is the value of prior relationships with customers in an environment of disruptive technologies?

Priceline empowered consumers to "name their own price" for airline tickets and hotel rooms; then it shopped these offers to marketers. Priceline's founder Jay Walker described the resulting transactions as a new ecosystem, that helped consumers realize lower prices while allowing marketers to turn excess inventory into profit and, in so doing, price discriminate without damaging their brands or their published prices. Airline tickets and hotel reservations were only the starting point for Priceline, however. By the end of 1999, Priceline had made inroads into the mortgage, new car sales, and car rental businesses. In November, Walker launched Priceline WebHouse Club to bring the "name-your-price" concept to groceries, with plans to eventually scale WebHouse to include almost every type of retailing. Several pressing issues confront the Priceline WebHouse management team in this case. First, the company had yet to close a deal with any major brand manufacturer. Thus, to satisfy customers, WebHouse subsidized member savings out of its own coffers, which, combined with early consumer success, led to significant losses and cash burn. To continue its customer acquisition, Walker projected that $200 million to $500 million in additional capital would be necessary. Meanwhile, the company confronted questions about where and how quickly it should expand.