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In the wake of some fairly spectacular “dot.com” crashes in the recent past, it is appropriate to open debate on the success (or otherwise) of new Internet “start‐ups” versus large incumbent conventional industry players (in retailing) starting their own Internet activities as separate “bolt‐on” businesses (and new distribution/communication channels.) This paper examines exploratory interviews with senior managers from a selection of “established” organisations in contrasting retailing sectors. Its purpose is to explore the challenges and issues faced by these large retailing organisations in establishing competitive Internet businesses. Insights and reflections are provided for other managers who are also following this line of business expansion. Some of the companies that participated in the research include Dell Corporation, IBM, Tesco Direct, Lotus Notes, Interflora, Flying Flowers, Virgin, Charles Schwab, Waterstones and Thomas Cook.

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