Here's an interesting perspective from Justin Kan, published on TechCrunch, about the general chaos and lack of planning at the inception of Justin.tv, how it emerged out of the failure of the calendar tool Kiko (which was dead the minute Google Calendar came out, and perhaps even before), and how, in fact, Justin.tv itself failed, and morphed (or pivoted, to use the word du jour) into its current form.
It's an interesting story, and worth passing to anyone who passes you a business plan with assurances that it will all go according to plan!