Kara Swishers nbspstare can make nbspCEOs squirm. Lovelys is pretty good too.
Kara Swisher’s  stare can make  CEOs squirm. Lovely’s is pretty good too.Photograph by Gillian Laub. Hair and Makeup by Victoria Stiles @ THE Artist Agency.
april 2023 Issue

“I’ll Walk Away From Anything”: Kara Swisher Calls the Shots

The ultimate media insider is juggling podcasts, writing a memoir, and texting with “half the planet.” (“She has a coffee before bed,” says Ben Smith.) Swisher opens up to Vanity Fair about her career, including leaving The New York Times, and laments journalists’ lack of business savvy. “If you don’t understand the economics of what’s happening,” she says, “you’re fucked.”

Kara Swisher, rocking aviators, AirPods, and a “Lesbians Who Tech” sweatshirt, rolls into Vox Media’s DC headquarters and gets right to work. Today’s episode of On with Kara Swisher, a twice-weekly podcast that launched in September, is about the future of the Republican Party after the House Speaker free-for-all, and she’s tapped CNN’s Manu Raju and The Bulwark’s Charlie Sykes to make sense of the mess. Once the guests come on camera, Swisher apologizes for wearing sunglasses, explaining that she forgot her prescription pair at home.

“It’s very Dark Brandon,” says Raju.

“I had it before him,” Swisher shoots back. “Let’s be clear on that situation.”

Swisher, as an interviewer, shows little tolerance for bloviating; she gets to the point. About halfway through the episode, she calls for a “lightning round” of House Republicans, asking Sykes to “tell us if the person is a true believer or a phony.”

Marjorie Taylor Greene?

“She is a conspiracy theorist, batshit-crazy bigot, and antisemite, and for some reason that has made her a rock star in the Republican Party,” says Sykes, a Never Trump–style conservative. And? “She’s a believer—it’s bullshit, but she believes in it.”

After wrapping up the podcast, her third taping that day, Swisher keeps up a rapid-fire patter with me. In the course of a few minutes, she bemoans the lack of “entrepreneurial” reporters, recalls “a big fight with Roger Goodell” after the NFL commissioner suggested her sons play football, and mentions talking the previous night with superagent Ari Emanuel about bull riding. But just like that, Swisher has to run—not to CNN, where she’s booked to appear that night—but for drinks with executives from CNBC. She recently declined to re-sign her contributor contract with the network because she felt constrained by its exclusivity rules “and the money wasn’t enough to keep me there.” Now they’ve come to talk to her again. “I always get approached by the networks,” Swisher tells me. “And they just never”—she lets out an exasperated sigh—“they never know what they want to make.”

Which is not a problem she seems to have. Beyond On, Swisher, 60, also hosts Pivot, a twice-weekly podcast with brash NYU marketing professor Scott Galloway; is writing a memoir about her beat-reporting days covering the dawn of the web; is working on a fictional TV show with another veteran Silicon Valley journalist; is advising Post News, a social platform she hopes will be a Twitter competitor; and is raising four kids, two of whom are toddlers. “She has a coffee before bed every night, after midnight,” Semafor’s Ben Smith texts. “This seems somehow emblematic to me. (In a good way.)”

Swisher, who is five foot two but “writes tall,” as she likes to say, has carved a considerable niche for herself, cutting across television, the web, podcasts, and social media—becoming “the queen of all media,” as veteran tech journalist Walt Mossberg puts it. A former Vox Media colleague is less charitable: “She’s always been searching for a way to make her platform even bigger, and she’s done that. But it begins and ends with her. There’s no legacy beyond that.”

Leaving legacy aside for the moment, Swisher has plowed a path through the media landscape alongside industry shifts, from reporting at a newspaper to blogging to cofounding successful websites and conferences to becoming a brand unto herself—part of a trend of elite journalists walking away from legacy outlets in pursuit of more freedom and, potentially, profits. Last year she gave up a podcast and column at The New York Times largely because, as she says, “I don’t need mama telling me what to do.” And she stepped back from Code, the iconic tech conference she’d organized and hosted for the past two decades. “It was like painting the same painting over and over again,” she tells me, “and I just wanted to make something else.”

On is the sixth podcast Swisher has hosted, but it’s the first where she owns the IP and has complete editorial control. She’s riffed on Elon Musk and Mark Zuckerberg while expanding her aperture well beyond Silicon Valley, interviewing the likes of Darren Star and Geena Davis, and exploring topics ranging from comedy to death. Swisher’s betting there’s an audience willing to turn to her for more than just expertise on tech moguldom. “I mentor a lot of people, and almost every single one of them is worried about losing their place if they step out of line. And I’m like, the only way you get higher is if you step out of line,” Swisher tells me. “That’s the only way. Seriously. Unless you’re untalented. And then you should stay in line.”

On a Monday afternoon in January, Swisher’s house is chaotic, but the good kind, the kind you find in a place where life is happening. Toys are strewn everywhere and a baby is laughing and sometimes crying and the sink is running in the kitchen, where the Golden Child—as Swisher’s three-year-old daughter is commonly referred to on her podcasts—is about to have a snack. There’s lots of talk of “Elsa cheese,” which is string cheese that Disney has branded with Frozen characters. The Golden Child crawls up onto the counter, where, at the opposite end, Swisher and her wife, the journalist Amanda Katz, are catching up on each other’s day.

“How was the Scaramucci thing? Who won?” Katz asks, referring to a public debate Swisher did that morning with financier Anthony Scaramucci on whether Musk—whom Swisher has known and covered since the ’90s—is killing Twitter.

“I did, obviously,” says Swisher. “I said he is, and it’s killing Elon more than he’s killing it.”

“And then Pivot was good,” Swisher says. “Scott made at least 14 prostitute jokes.”

Despite having a ministroke a decade back, Swisher famously does not like taking time off and works around the clock. In December, “she had heart surgery and she was working the day before and the day after. That’s not an exaggeration,” Galloway tells me. (When I ask Swisher how the surgery went, she replies, “Good, obviously.”) Her turbocharged work ethic could be traced, in part, to tragedy early in life. When she was five, her father died suddenly at 34 of complications from a brain aneurysm. Fresh out of the Navy and with three kids, he’d just purchased his first house and landed a gig as the head of anesthesia at the Brooklyn Jewish Hospital. “He thought he was headed for the big time. He just died—fell over one day. And that has informed everything I’ve done. I’m like, I don’t have time for this,” says Swisher, adding, “You don’t have time, either. Nobody has time.”

Swisher’s mother remarried soon after, to a “cruel” man whom Swisher “couldn’t say enough bad things about” but admits was a “canny engineer.” When Swisher was in sixth grade, they moved from Long Island to Princeton, New Jersey, for his work, and when the rest of the family moved to California a few years later, Swisher stayed behind. “I was like, I’m the yearbook editor. I have a boyfriend. Fuck you,” she recalls. “I lived with friends and finished my senior year by myself, pretty much.” (Swisher knew she was gay from age four but didn’t have a girlfriend until college.)

At Georgetown’s School of Foreign Service, she studied propaganda, an education that shaped her view of misinformation and Donald Trump’s manipulation of the media. “I think I was one of the first to say there’s real damage going on here and we have to start paying attention to it,” Swisher says. “You have to be able to look at that and see what they’re doing, even if you decry it and hate it…. I was always interested in the moving of the Overton window.” Swisher wanted to follow her father into the military. “I thought I might go into the CIA,” she says. But that would’ve required her to lie about being gay. “I didn’t even try.”

During college, she worked as a stringer for The Washington Post after complaining to then Metro editor Larry Kramer about a sloppy story they’d published on a Georgetown event. Years later—after stints at Columbia Journalism School (“a waste of money” that she wished she’d “invested in Apple stock” instead), the Washington City Paper, and the political chat-fest The McLaughlin Group (whose host, the late John McLaughlin, she later testified against in a sexual harassment case)—she returned to the Post, working her way up from Style news aide to reporter on the local retail beat. “The Post is where I significantly started to use technology,” says Swisher, recalling the suitcase cell phone she used to lug around the office.

Swisher put herself on the map nationally at the Post while covering the defining dot-com saga of the ’90s: AOL and its eventual disastrous merger with Time Warner. “Kara always had this larger-than-life personality. I remember her [as] short, feisty, the kind of person who sets the room alive,” recalls the Post’s David Ignatius, who was business editor when Swisher was writing for the section. “She was a star. We knew we couldn’t hold her.”

She left to write her first of two books on AOL, meeting Mossberg along the way. He recommended her for a job at The Wall Street Journal, where in 2003 the duo launched the AllThingsD conference, a live-journalism extravaganza featuring the biggest names in tech. It was at this conference in 2007 that Bill Gates and Steve Jobs took the stage together in a historic joint interview and, a few years later, where Zuckerberg broke into a profuse sweat amid questions about Facebook privacy.

“Kara’s never ad hominem. She might be snarky, but she doesn’t attack people; she attacks their actions and their ideas,” Mossberg tells me. “People feel that her interviews can elevate them, and sometimes it can hurt them, but that it’s worth the price of admission,” says veteran executive producer Tammy Haddad. A recent example is CNN chief executive Chris Licht, who, to put it mildly, got off to a rough start. It was strategic for Licht to give his first extensive interview to Swisher, a source close to the CNN chief acknowledges, as Swisher “had the credibility to help reshape the narrative but also would give the impression that Chris is pretty fearless, because she’s a tough interviewer.”

The success of the conference convinced Dow Jones to let Mossberg and Swisher start the AllThingsD blog. They left in 2013 to start their own venture, for which they’d raised $10 million in funding, taking the AllThingsD staff with them and trying, unsuccessfully, to take the brand too. But Journal owner Rupert Murdoch, she says, wanted $10 million for the URL. “I wrote them back. I said, ‘I can buy FuckYouRupert for $10.’ ” So AllThingsD became Recode and the D Conference became the Code Conference. About a year and a half later, Vox Media purchased Recode in an all-stock deal.

CEO Jim Bankoff, who first encountered Swisher as an AOL executive on the other end of one of her reporting calls, basically let her do whatever she wanted at Vox Media. Not long after the sale, Swisher stopped running Recode—“I hate managing,” she says—and started the Recode Decode podcast. What really sold her on podcasting was the “emotional attachment” listeners felt to her as a host. Part of what makes Swisher so compelling is her ability to “move between the personal and the work with ease,” says New York Times CEO Meredith Kopit Levien.

Swisher noticed that her “geek guy” audience began to expand after venturing into podcasting, such as when four women of color, all entrepreneurs, approached her on the Muni in San Francisco. “Kara, it’s you. I can’t believe it. I’m like, this is not my fuckin’ demo,” Swisher remembers. (More recently, a firefighter “made a one-eighty in the street in New York” to take a selfie with her, she recalls. “He’s like, I love you…. I knew these NFTs were bullshit, thank you for explaining it to me.”) She signed off as host of Recode Decode in July 2020, five years and more than 500 interviews later. By then she’d started Pivot. The dynamic is Galloway as provocateur and Swisher reeling him in. Also in 2020, Pivot became part of New York magazine, which Vox Media had acquired a year earlier.

Despite the New York association, Swisher, who has two teenage sons with her first wife, former Google executive Megan Smith, is living in DC again. For most of our conversation at her home, she wears her signature aviator sunglasses until it’s dark enough that she gets up to turn on a lamp. (She has an eye condition that causes sensitivity to light. “The aviators are a brand thing; the dark glasses are not,” she explains.) As we’re talking, we are occasionally interrupted by other pieces of Swisher’s life popping through the doorway—the cat, Katz, and the Golden Child, who comes in to ask Swisher to help her put the shoe back on her Barbie. Fiddling with the plastic shoe, Swisher tells her daughter, “Honey, I never played with Barbies.” Swisher tells me she did an interview with the CEO of Mattel and told him she hated Barbie; afterward, he sent her a box of them. “I let her keep one and I gave the rest to charity.” The Golden Child leaves the doll on the table in front of Swisher, who proceeds for the next hour to stroke Barbie’s hair while we talk.

“The word brand—it makes you feel like you’re a jar of peanut butter,” says Swisher, recalling how people used to lodge it as an insult. “I’m making something that has my name on it, and because of the new tools available to us through the internet, we can now get our voice out there in ways we couldn’t,” she says. “I think I was one of the first to say that to people. And obviously, the people who run these places do not like that message. When I left the Journal, everyone suddenly was like, You can leave? They were shocked.” She whispers, “I was like, You can leave.

“I’m trying to teach you that, right?” Swisher says to her daughter, who nods. “Yeah? You gonna do what you wanna do?” Another nod. “Yeah. Good. You’re gonna watch Frozen all the time is what you’re gonna do.” Swisher, lowering her voice, tells me, “It’s heroin. I texted Bob Iger, I’m like, stop. You put it on cheese. What the fuck!”

“Honey, I never played with Barbies,” Swisher tells her daughter. She let her keep one from a box sent over by Mattel’s CEO.Photograph by Gillian Laub. Hair and Makeup by Victoria Stiles @ THE Artist Agency.

When I ask Swisher whether the success of Pivot has given her the freedom to turn down or leave other projects, she practically snorts. “I’ll walk away from anything,” she says. “I always feel like I can make something else.”

Case in point: The New York Times, where Swisher landed an Opinion column in 2018. Then came Sway, a twice-weekly podcast about power that was meant to be a Terry Gross–type show—Hillary Clinton and Jane Goodall were early guests—but changed direction over time as it became more reactive to news. Some episodes made a splash, like one in the aftermath of the January 6 insurrection in which Swisher pressed Parler CEO John Matze on the right-wing social media platform’s role. Apple cited his comments on Sway in its decision to remove Parler from its App Store. Matze was fired a month later. But then Swisher started to get “itchy,” as she puts it, particularly with the column, which she says can become “a live coffin” for people who stay too long. “I think most people have 40 good columns in them.”

And there was tumult at Sway. Six people left the Times after about a year or less of working on the show. “It was totally known across the Opinion audio department that this was a nightmare show to work for,” says one Times staffer, who, along with three former Opinion audio staffers, points to impossible deadlines and poor management. There were “months and months of interventions and people trying to fix it,” the staffer says. When I ask Swisher how she felt she was as a manager on Sway, she says she wasn’t one; she was talent. “Nobody reported directly to me,” says Swisher. “I didn’t hire them. I didn’t fire them. I didn’t do their reviews or anything like that. I wasn’t involved in anybody’s review, unfortunately.”

As for the turnover, she says, “I think it was that they didn’t hire the right people in the first place,” because “I do news.” I point out that Sway was a product of the Opinion side of Times audio, not its news division, which she dismisses as an irrelevant distinction. “When something happens, I want to do it right away…they just didn’t wanna move that way. I totally get it, I completely respect it, but I just didn’t want to do the slower show. I wanted to do the fast-burn show. And so it was a real struggle.”

Swisher started hosting conversations on Twitter Spaces. “I was making something else. When I have four children, four podcasts a week, a column…what does that say to you? I’m not making what I wanna make.” She was also chafing against the Times’ bureaucracy. “I just wanted to make what I wanted to make, and I didn’t wanna ask 86 people. They’re all really smart. They just aren’t me.” (New York Times Opinion editor Kathleen Kingsbury applauded Swisher’s “unmistakable voice” and says the section was “grateful for her four years of reporting and commentary for us.”)

As Swisher was getting increasingly restless at the Times, she was considering opportunities elsewhere, including The Washington Post, which was talking to her about a role spanning podcasts, live events, and columns. “They wanted to bring in a star, and they just didn’t wanna pay,” says Swisher. She went furthest down the road with CNN, which wanted her to host a show on CNN+ and was offering “millions of dollars,” according to Swisher. Galloway had already signed his own deal to host a program on the forthcoming streaming service, but she was wary given the impending Warner Bros. Discovery merger. “They’re gonna have to cut something big and guess what’s big and stupid? That,” she said of CNN+, which Discovery quickly killed off.

Swisher wanted to make a different type of interview show, less formal than Sway and “more about me,” Swisher says. “I just didn’t think I could make it there. The audience was different. They weren’t in on the joke.” Over at New York, editor in chief David Haskell was on the same page. “You know, I listened to it. I was sometimes jealous of it,” he says of Sway. “And there were ways in which I also thought we might be a better home for her.” Once she’d decided to leave, Swisher first told Levien, the Times’ CEO. “I didn’t go to the editorial people. I knew they’d be hurt…they have a vision of nobody leaves the Times, but she got it right away,” says Swisher. “It was good to have her at the Times for the stretch we had her, and it makes sense to me why she moved on,” says Levien, describing Swisher as a “force in the industry.”

Over lunch at a Japanese restaurant in Cathedral Heights, I ask Swisher how much of her decision to leave the Times had to do with ownership. “A lot,” she says, between bites of salmon teriyaki. “What was happening at the time is I find out that all the stuff at the Journal, the AllThingsD stuff, disappeared from the internet,” says Swisher. “They were so careless with my stuff,” she says. “I’ve done a thousand or more interviews. I own none of them.” Meanwhile, there she was at the Times, growing something else that wasn’t hers. “I also wanted a piece of the revenue again, and the Times is not gonna do that, sorry to tell you,” she says. “I was working at a discount at The New York Times for what I make.”

As Bankoff was preparing to launch The Verge in 2011, he decided to break the news in a co-exclusive with Swisher at AllThingsD and the late David Carr at the Times. “She made it very clear to me that if I were to burn her—i.e., hold up information from her that Carr was getting—there would be repercussions,” Bankoff recalled, laughing. “I’m not exactly sure what those repercussions would be…but I knew then, and I know now, that you keep your word with Kara.”

“I used to be so aggressive about that stuff. Not anymore. I don’t care,” Swisher tells me when I ask her about this story. “Scoops don’t matter anymore because they’re so ephemeral,” she says. Still, she bristles at the idea that she’s not still reporting. “I do reporting all the time,” she tells me. “It manifests itself in my interviews,” says Swisher. “I’m doing reported analysis now. I am not doing punditry.” (Even if she’s toned down her reporting style, she’s still seen as someone not to cross: Multiple people wouldn’t speak to me for this story because, they reminded me, Swisher is a powerful person.)

“She’s willing to get into the brawl with me,” Emanuel, the Endeavor CEO, told me, likening his and Swisher’s back-and-forths to the “Friday-night dinners at my house that I used to have—you had to come with a strong argument and points of view, and willing to throw blows and take blows.” Emanuel met Swisher more than a decade ago at a Silicon Valley gathering. “She’s somebody that when I have a question about their point of view, and I trust their point of view, I’ll pick up the phone and say, what’s your take on this?”

Swisher sees her role now less as breaking news about tech companies than interpreting the words and actions of the industry titans she knows “very well.” Take Musk, for example. They’re not on speaking terms—he recently called her an asshole in an email—and yet Swisher has still managed to position herself as the go-to Elon expert. She’s even featured herself as the guest for an On episode titled “Elon Musk: Somebody That I Used to Know”; Swisher’s executive producer and on-air sidekick, Nayeema Raza, conducted the interview. Swisher similarly served as interviewee on a recent Zuckerberg episode, and as with Musk, takes on the role of tech industry conscience. “Part of the power of her podcast is there’s a sense of somebody who has been here the whole time and is kind of fed up,” says tech journalist Casey Newton, who considers Swisher a mentor (as well as a landlord—he rents her guest cottage in San Francisco).

The often blurry line between Swisher the insider and Swisher the reporter is precisely her appeal. “Kara’s sort of in constant text conversation with half the planet, and it’s a thrill to realize that that’s what’s buzzing in your pocket,” says Haskell. (I got my own glimpse of this over the course of reporting this piece, as I’d get random texts from Swisher, at all hours, weighing in on the media topic du jour and once accidentally roping me into a group chat with her agents.) Those who socialize with her in the capital describe her in a perpetual state of gathering string. “She knows everybody, and she gets invited everywhere, because she’s fun,” says legendary Washington journalist and host Sally Quinn, whose late husband, Ben Bradlee, hired Swisher to the Post. “She also has an incredible bullshit detector—which is always helpful in Washington,” Quinn adds.

Swisher is in the middle of writing her memoir about covering the early days of the internet. It’s taking her a while, because, in addition to “all these children, jobs, and heart surgeries,” she tells me, “I don’t like the people I’m writing about anymore.” (A few weeks later, at an absurdly late hour, she texted that she’d just finished her chapter on Jeff Bezos. “Tomorrow: RUPERT,” she added.) As part of a two-book deal, Swisher also hopes to write a book with her brother, the doctor Jeffrey Swisher, about the science of living forever.

At the moment, she’s also working on a documentary about AOL with Left/Right productions—“It’s a great concept” and “I’m the only one who can help them”—and a scripted show about tech with Bloomberg’s Brad Stone, who is doing the screenwriting. They have a showrunner, “so we’ll see if we sell it,” says Swisher. She’s also been advising Post News, a social network founded by former Waze CEO Noam Bardin, and has been encouraging people to join it on Twitter. “I would like a viable competitor [to Twitter] by an entrepreneur I respect,” Swisher says. “I hate that there’s one Twitter.”

Swisher says she tries to structure her deals “where I get a piece of it for my success.” For Pivot, she received Vox Media stock that can be converted to cash after four years. With On, she owns the IP, has a minimum salary, and they share the revenue after costs. “I think reporters are super uncomfortable talking about money, and I’m not at all,” she said. “I really hate that journalists don’t understand business. If you don’t understand the economics of what’s happening, you’re fucked.”

“She clearly, through her journalism, understood not only the value but the power of intellectual property while covering what others were doing in that space,” Disney CEO Bob Iger, who has bantered with Swisher both offstage and on for years, tells me. “There she was with a front-row seat to the mining of great intellectual property—using technology, really—as a means of creating value,” he says, adding that Swisher “in effect turned the results of her own reporting on herself.”

In February 2022, Galloway and Swisher held the inaugural Pivot Conference, in which they both have an ownership stake. “It was not a financial success. It was very expensive to put on,” Galloway tells me. They’ve held other live Pivot events—including in Germany and London in January—but are still figuring out what’s next. About half of Pivot’s audience is Gen Z or millennial, with more than 70 percent in the 18-to-49 age bracket, according to a Vox Media spokesperson. One idea is going to business schools, where Swisher says Pivot has “a crazy fan base,” and creating some sort of networking occasion. “Something else besides people sitting in a fucking ballroom,” she says.

Even with so many projects swirling in the present, Swisher has an eye toward posterity. “In history, they’re gonna watch that Gates and Jobs interview. A hundred years from now—that’s how we got them to do it, really,” she told me. “They’re gonna watch all these interviews…it’s like you had Thomas Edison, and I challenged him. Rather than what grows up around them, the mythology, you’ll be able to hear them being interviewed by someone who was good at interviewing.”

CORRECTION: An earlier version of this story misstated the technology Swisher used while working at The Washington Post. She used a suitcase cell phone, not a Kaypro computer.