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‘Appalling’: Salesforce CEO bickers with Kara Swisher on Musk, Salesforce Tower

Stephen Council

Kara Swisher had already grilled Marc Benioff about the ugliness of San Francisco's Salesforce Tower and his company’s mass layoffs. But when the veteran tech journalist brought up a 2018 incident in which Benioff referred to Laurene Powell Jobs as Steve Jobs’ widow, he appeared to snap.

“Do you have a catalog of all the things I’ve done wrong?” the Salesforce CEO asked 40 minutes into their interview. Her answer: “Yes.”

Swisher interviewed Benioff in front of a crowd at the Upfront Summit in Los Angeles on March 2. The wide-ranging conversation saw two San Francisco techies bickering over Elon Musk, Salesforce and more. “I like you better than most, but it’s a low bar,” the journalist said as the interview began and then yanked Benioff through a verbal obstacle course of his past mistakes and contradictions. 

The interview was published through New York Magazine’s “On With Kara Swisher” podcast. A tech journalist who documented the rise of internet-based companies for several national publications before turning to long-form interview podcasts, Swisher has a long-standing rapport with executives like Benioff and, up until recently, Musk.

Benioff — jovial and quick-talking — defended his 8,000-employee layoff round, even saying that Salesforce will hire “a lot” of the employees back. He dodged questions about activist investors, basked in his firm’s recent successful earnings report and called himself “the best-performing enterprise software executive of all time.”

He admitted he regrets not buying Twitter a long time ago, adding that he’s always been in love with the platform. 

The billionaire also talked about standing up to Mike Pence back in 2015 when the former Indiana governor signed an anti-LGBTQ law. The executive threatened to scale back his company’s investment in the state in a much-praised tweet that was fired off after a few glasses of wine. He “drunk-tweeted,” Swisher said, then went to bed and woke up as the face of a corporate movement.

“I turn on the television,” Benioff said, recounting the morning after. “My tweet is on the TV. I’m like, I'm watching CNN. Is this a bad dream? Is it a nightmare? What is happening? This can’t be true. But it was right on the television. And I was like, well, I hope I spelled everything correctly.”

Swisher took a moment to poke at Benioff about Salesforce Tower, which she said had ruined her view: “I have a beautiful view, and I’m always looking out, and there’s the penis.”

“I didn’t build the building,” Benioff replied, “so I apologize on behalf of Boston Properties.”

“And yet you approved it,” Swisher said, prompting him to apologize again. She went on to add, “Honestly, I hate your building.”

“I ask the whole world to forgive me, and I will forgive the world,” he replied.

In the most heated portion of the interview, Swisher took Benioff to task over his defense of Elon Musk. Benioff praised Musk shortly after the Twitter and Tesla CEO had shared a homophobic tweet about Paul Pelosi. Swisher texted Benioff, she said, and he eventually called her because she was so angry. 

“I know I got you really upset. I mean, I haven’t really seen you that upset,” Benioff said in the interview.

“But it’s easy to say ‘upset,’” Swisher said. “I’m not upset. It’s appalling.”

They argued about Musk for a while, with Swisher questioning how Benioff gets past Musk’s crude behavior. Benioff said, “I see the good in everyone. Maybe I’m too focused on that, and maybe you’re the opposite.”