In reality, Mr. Kalanick had little intention of staying away from his company. Almost immediately after announcing the leave of absence, he worked the phones to push out Mr. Bonderman for making the sexist comment onstage at an Uber employee meeting. With the two increasingly at odds, Mr. Kalanick sent out a flurry of texts, phone calls and emails to his allies to pressure Mr. Bonderman to step down from Uber's board. Hours later, Mr. Bonderman did.
By then, Mr. Gurley, who had been one of Mr. Kalanick's earliest supporters, saw that Uber's promises of change were not enough if the chief executive stayed on.
Over the past week, Mr. Gurley and his partners spoke with other Uber investors at venture capital firms, including First Round Capital, Lowercase Capital and Menlo Ventures. Together, they came up with a letter to Mr. Kalanick that listed four demands, the foremost being his resignation.
The venture firms declined to comment.
Mr. Gurley and the group sent Mr. Cohler and Mr. Fenton, who by then had better relationships with Mr. Kalanick, to deliver the news in Chicago. They anticipated a fight, with Mr. Kalanick often eager to instigate one.
For a spell, a battle appeared to be coming. Mr. Kalanick sent his own surrogates at Uber's headquarters in San Francisco to begin a whisper campaign among investors and try to work out some sort of compromise in private.
But after hours of negotiations and consultations with confidants, Mr. Kalanick decided he had had enough. At around 11:30 p.m. on Tuesday in Chicago, he drafted a statement about his resignation. Then he agreed to make it public.