Two billionaires discuss homelessness, a dramatic timeline

Faceless face-off.
Faceless face-off.
Image: Reuters/Chris Wattie, Reuters/Mike Blake, Twitter
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It began innocently enough on the evening of Oct. 8, when Marc Benioff, the founder and co-CEO of Salesforce, shared this tweet:

Benioff was advocating for Proposition C, a ballot measure that would raise taxes on big businesses in San Francisco in order to fund programs aimed at fighting homelessness.

Innocent? Sure. Controversial? You bet.

This tweet started a fight with none other than fellow tech billionaire Jack Dorsey, who runs the very platform Benioff used to tweet—Twitter. Eventually it turned into a battle over which super-ultra-wealthy people appeared to be tweeting more in favor of the poor.

Four days later, Jack shocked Twitter by quoting the above tweet and saying,

Why did he wait four days? What compelled him to respond so boldly, specifically challenging Benioff’s support for Prop C? We’ll never know. All we’ll know is that he didn’t use a computer to do it.

Things only escalated from there. Benioff countered Dorsey just eight minutes later, responding, “Hi Jack. Thanks for the feedback” (burn), and “Which homeless programs in our city are you supporting? Can you tell me what Twitter and Square & you are in for & at what financial levels?” (also burn). This response got even more retweets than Jack’s (sickest burn).

These two Richie Riches continued to debate which of them cared more about homelessness. Jack again invoked the mayor of San Francisco, who does not support Prop C. Marc gave Bloomberg another burn of a quote on the dramatic, consequential dispute, saying, “If you’re going to fight a relatively small tax…then you better prepared to talk about what you are doing versus what you don’t want to do.” He also said this:

With no discussion of actual policy having taken place, Benioff looked to be winning. He positioned himself as the benevolent, shall we say Benioffelent, billionaire to Jack’s out-of-touch, hipster-bearded, “don’t tax me” fat cat.

But Jack had an ace up his sleeve. One that nobody expected. A few hours later, he put the onus back on Benioff with a brilliantly simply maneuver: A phone call.

It seemed the disagreement would never get resolved. News outlets pitted the two against each other. “Marc Benioff and Jack Dorsey spar over proposal to fight homelessness,” said CNBC. Forbes had them “squaring off.” The San Francisco Examiner called it “trading barbs,” which nobody ever says.

But then, at last, Jack executed the final move, miraculously pulling out a draw when, just hours ago, it looked like checkmate.

How many homeless people did Dorsey and Benioff walk or drive by during that eight-minute call? Were any of them spoken to? Do these guys get to talk to the mayor any time they need to save face in a Twitter spat? Was eight minutes enough to “align” their vastly different positions?

We won’t be able to answer those questions, either. But at least both of these billionaires came out looking like they care about homelessness. That’s the most important thing.