Kara Swisher’s interviews made her famous among technology obsessives decades ago. She persuaded the rivals Bill Gates of Microsoft and Steve Jobs of Apple to play nice onstage. She reduced Meta’s founder Mark Zuckerberg, then just 26, to a puddle of sweat. She shoved her camera in the face of her future boss, Jim Bankoff, Vox Media’s chief executive, among others.
But it wasn’t until she began podcasting that she reached an audience far beyond the tech world.
In 2018, she started “Pivot,” a news-chat podcast, with Scott Galloway, a serial entrepreneur and marketing professor who now has his own slate of brash business podcasts under the name “Prof G.”
They were an odd couple — she was grouchy, he was raunchy — but their banter was tender and intellectual when they weren’t torturing each other. Fans began stopping Ms. Swisher in public, recognizing the aviator sunglasses that had become a swaggering signature.
“I’d never made a product or a news thing that people thanked me for,” Ms. Swisher, 62, said in a recent interview at a cafe in the shadow of the National Cathedral in Washington, where she lives with her wife and children. “At the end of this long career, it’s like, ‘Oh wow. I make something people really like.’”
So she and Mr. Galloway decided to assess its worth, shopping their portfolio of five podcasts around to other companies before their contract with Vox Media, their publisher, neared its end.
Competitive offers came in with guaranteed payments of about $40 million on four-year contracts, Ms. Swisher said. But in the end, they agreed to re-sign with Vox Media, with an unusual twist.
The deal does not carry any guarantees or upfront cash. The payday for Ms. Swisher and Mr. Galloway is instead based entirely on how much money their podcasts generate. Vox Media will pocket about 30 percent, while the co-hosts split the rest.
At the high end of back-of-the-envelope calculations — Mr. Galloway said the podcasts could generate $100 million in revenue over the four years — the pair would stand to make about $70 million excluding some costs. (A portion of the costs for their slate of shows is split among the hosts and Vox Media.)
The novel structure of the deal cements Ms. Swisher’s reputation for betting on herself. But it is also the kind of deal that could have wider implications, as more journalists follow Ms. Swisher’s example in fashioning themselves as new media entrepreneurs.
Ms. Swisher’s path to celebrity — a power broker who name drops other power brokers — has taken her from The Washington Post; to The Wall Street Journal; to The New York Times, where she was an opinion columnist and host of a podcast called “Sway.”
Along the way, she co-founded two media businesses, AllThingsD and Recode, published three books, survived a mini-stroke, raised a family and harbored few regrets. (Here’s one: “I was too nice to Elon for too long,” Ms. Swisher said of Elon Musk, the Tesla chief executive.)
She also learned a fundamental truth about herself: She does not want to be an employee, nor does she want to employ anyone. She wore a sweater to a White House Correspondents’ Association dinner party that warned people, or perhaps boasted, “I’m not for everyone.”
“Every day I get to decide what I do,” she said, “and it’s not dependent on anybody.”
Except, in some ways, Mr. Galloway and Mr. Bankoff of Vox Media.
Mr. Bankoff and Ms. Swisher got into business together in 2015 when Vox Media bought Recode, a tech news site she had started with Walt Mossberg, a pioneering technology journalist at The Journal.
Mr. Bankoff characterized the hosts as “tough” during the negotiations over “Pivot.” “They’re not going to give us some home-team special,” he said during an interview at his home in Washington. But there was mutual trust, he added. “The trust is born out of us performing together.”
Mr. Galloway, 60, the more feral half of their screwball comedy team, negotiated the finer points of the “Pivot” agreement. Ms. Swisher confirmed the terms of the deal.
Vox Media, for example, still owes the duo $20 million for completing their first deal. Mr. Galloway concocted a plan that allows the pair to receive that money in installments over seven years with interest, rather than pay a hefty tax on a one-time check.
“What I constantly say to Kara is, ‘You need to start thinking like a billionaire,’” Mr. Galloway said. “She’s making me much more famous. I’m making her richer.”
The pair are the hosts or co-hosts of four other podcasts at Vox Media: “On,” Ms. Swisher’s solo interview show; “Raging Moderates,” a political podcast with Mr. Galloway and the Democratic strategist Jessica Tarlov; “Prof G Markets,” focused on the global economy with the business writer Ed Elson; and “The Prof G. Pod,” which features Mr. Galloway’s business insights and life advice.
Ms. Swisher’s reach in the media world goes far beyond Vox Media. She is finalizing a deal for a documentary series about cheating death, produced with EverWonder Studio, probably for CNN, where she said she already earns around $250,000 annually as a contributor. She is working on a book about mortality and future tech. There is a potential TV show based on her memoir and another possible series about tech moguls. She also serves as a consultant on a D.C. version of the series “The L Word.”
Last year, she said she learned about “sexual text messages” between a writer at New York magazine, Olivia Nuzzi, and Robert F. Kennedy Jr., now the health secretary, whom Ms. Nuzzi profiled while he campaigned for president. (New York magazine is owned by Vox Media.) She said she passed the information to the magazine, and Vox Media later disclosed the relationship.
All of this activity means Ms. Swisher is basically working nonstop, Mr. Galloway said. “She’s always in motion.”
Her intensity initially put some strain on their relationship — there was some “storming, norming and forming,” Mr. Galloway said. “The good news is, I can text her at any time,” Mr. Galloway said. During an interview, he tested this out — she responded within seconds. “You adore me,” she shot back.
“The bad news is: She does text me at all times,” he said.
There is still more that Ms. Swisher would like to do. As morale sagged to new depths at The Washington Post in recent months, she mounted a public campaign to buy the newspaper from its owner, the Amazon founder Jeff Bezos. (Mr. Bezos has given no indications he is willing to sell.) She has also talked to Mr. Bankoff about using Vox Media to create a new consortium of independent media properties.
She has worked, too, as an informal adviser to the growing number of journalists who, like her, have moved to start their own ventures.
Her level of support varies. When Casey Newton, a tech journalist, left Vox Media to start his own newsletter, she offered to let him stay rent-free in the guesthouse of a home she owns in San Francisco. (He is now also a co-host of “Hard Fork,” a New York Times podcast.) And she encouraged the CNN anchor Christiane Amanpour to start her own podcast about world events, “The Ex Files,” over dinner in London.
After another CNN anchor, Don Lemon, was fired by the network in 2023, Ms. Swisher advised Mr. Lemon not to get into business with Mr. Musk. Mr. Lemon did, and the two are now locked in a legal battle over the termination of his show on X.
Onstage with Mr. Lemon last year while promoting her memoir, Ms. Swisher expressed admiration for his leap to independent media.
“You’ve given up the town cars and fancy things for your own entrepreneurial sense,” said Ms. Swisher, who was wearing a Hawaiian-style shirt printed with her book’s cover. “You should have an interest in the outcome, which means the revenues and profits.”
Jessica Testa covers nontraditional and emerging media for The Times.
Benjamin Mullin reports for The Times on the major companies behind news and entertainment. Contact him securely on Signal at +1 530-961-3223 or at [email protected].
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