Another company he was advising, Formspring, a question-and-answer site that had raised $14 million, seemed poised to become the next big social website and was negotiating with him to be its chief operating officer. Ade Olonoh, the co-founder of Formspring, says that discussions got so advanced that Kalanick was offered the role and there were board conversations about Kalanick’s compensation. Kalanick told me it was one of several jobs he considered at the time.

