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As a result of his support for a variety of local school projects, Mr. Benioff has largely escaped the withering criticism that other tech billionaires, such as Bill Gates and Mark Zuckerberg, have faced for their school initiatives.
“Other billionaires tend to hop around different places, leaving half-completed reforms in their wake,” said Sarah Reckhow, an associate professor of political science at Michigan State University who studies philanthropy. “It will be interesting to see if his education investments have more staying power.”
Mr. Benioff is not as dramatic in his display of wealth as Mr. Ellison, who is a collector of costly cars, homes and yachts — and a winner of the America’s Cup sailing race. But the Benioffs have multiple homes in San Francisco and a residential compound on the Big Island of Hawaii, and he has hosted private concerts by his favorite musical artists. Stevie Wonder performed at the couple’s wedding, as well as at a fund-raiser that Mr. Benioff hosted for President Barack Obama.
During the interview Sunday night, Mr. Benioff sent cartoons; links to Time stories on YouTube; chunks of what sounded like news releases but were, he insisted, original (“Time is the best fit for us, and most reflects our values and interests”); discussions of his and his interviewer’s Judaism; and quite a bit more. It is impossible to imagine Mr. Zuckerberg, for example, behaving like this with a journalist.
But if Mr. Benioff was very charming, he was not very forthcoming. His most revealing moment was when he said, “I live with a beginner’s mind,” and then texted a screenshot of a quote from the Zen master Suzuki: “In the beginner’s mind there are many possibilities, in the expert’s mind there are few.”
It was a momentary glimpse of the tremendous freedom that tech billionaires are afforded. The world is both their plaything and, Mr. Benioff stresses, their responsibility.
“My power,” he said, “was that I didn’t really want to do anything but I was open to all possibilities.”