Media People: Kara Swisher, Tech Journalist, Podcaster

Kara Swisher’s career could have turned out very differently.

For a long time, the journalist and podcaster, known for her casual way of holding the feet of some of the world’s richest tech lords to the fire, along with decades of scoops, had her mind set on being in the military. Military intelligence to be exact. Or a spy in the CIA.

“People are always surprised,” Swisher said. She’s in a room in her house in her relatively new permanent home city of Washington, D.C., after years spent going back and forth between there and San Francisco. A new baby and two older children in school on the East Coast made a move necessary.

The only thing that stopped Swisher from joining the military, after several members of her family, including her late father, was Don’t Ask, Don’t Tell. “I’m not a don’t teller,” she explained.

That she is not. Speaking with Swisher for an hour is like a marathon squeezed into a single mile. Her sentences go on, but do come back to a point, sometimes two or three. If something comes to her mind, she tends to say it or explain it right away. And she thinks while she’s talking, and talks fast. If you’d like to get a sense of talking to her in person, read at double time. And be prepared to like her, if you don’t already.

She’s direct but relaxed and friendly. She ate some chili with crackers during a Zoom interview. Not a stitch of makeup on, wearing a black hoodie that said “Queen Inclusive Badass.” She has a confidence in what she does that is refreshing — it tends to be rare, particularly among women. Self deprecation isn’t her thing. Swisher knows that she’s good at what she does and doesn’t waste time pretending she’s not. She knows that she makes money for the publications she works for and uses it to her advantage. She knows when she’s right and when someone, say Mark Zuckerberg or Elon Musk, is wrong, and isn’t afraid to say it.

Swisher could have easily gone to work in tech, too, instead of giving the public sharp coverage of it since the Nineties.

“I’ve been offered a job at every major Internet company,” Swisher admits. She toured spaces for Amazon’s first office with Jeff Bezos. She covered Google from its inception. She knew Elon Musk “when he didn’t have hair.”

Why she didn’t is something of a mystery, even to her. But it seems the main draw for most, that being piles of money, just didn’t interest her.

As for who she actually works for now, since she has a new podcast “Sway” with The New York Times, her “Pivot” podcast with NYU professor Scott Galloway has moved to New York Magazine and she’s still associated with Recode (the latter two now both owned by Vox), the technology news web site she founded with Walter Mossberg, even Swisher admits, “It’s confusing.”

The simplest answer is she’s not an employee of any and her decision to join The Times in 2018 was strategic. They’d been chasing her for years, but the size and breadth of its audience started to appeal when misinformation on social media became endemic, particularly on Facebook.

“I knew if I had the firepower of The Times behind me, technology would pay the f–k attention to the damage they were doing.”

But really, it’s podcasting that got Swisher “excited again,” a contrast to what she’d started to feel for her beat reporting.

She also seems to be looking forward to a memoir of Silicon Valley she’s working on as part of a new two-book deal with Simon & Schuster. The topic of the second book is undecided, but it’s completely up to Swisher. She’d avoided another book since her first two, a 1999 tome on AOL and a sequel in 2003. Simon’s new chief executive officer Jonathan Karp, who edited her AOL book, lured her to the deal.

“I kind of really do want to write a memoir,” Swisher said. “I have all the receipts. And now I don’t care. I’m gonna tell you what it was like at the fair.”

Here, WWD catches up with Swisher on her start in journalism, her experience in the industry and her reputation as an interviewer, along with her thoughts about the power of tech and podcasts — and where she’d be now, had she ended up in the military.

WWD: I see you as someone who has a lot of power in journalism, and the new podcast is about power, as you’ve described it, so I’m wondering how you’ve gotten the power you have today and how you go about using it?

Kara Swisher: One of the things I think about a lot as a journalist, not just as a journalist but as a person in the world, is I tend to try to play the long game. One of the things I tend to do very well, unlike a lot of reporters, I understand strategic versus tactical, in terms of the career. And in terms of timing and timing things really well.

The second thing I do really well is, I think really hard about leaving when I haven’t learned enough. A lot of people stay in the same jobs. I’m good about instinctively knowing when to leave. Like, I was at The Washington Post, I did very well there, but I didn’t want to run it. I looked around one day and said. “I don’t want to be anybody here above me.” So I left. A lot of people aren’t like that.

WWD: When you make a move like that, is it because you’ve prepared and saved up enough money and thought ahead in that way?

K.S.: No. I always think I can work. I know I’m talented. I know I have skills. I’m good at interviewing, I’m good at asking questions, I was always a good writer, so I feel like I can work anywhere. I don’t worry, “If I don’t get this promotion, oh no, what will I do?”

Listen, I’m a well-educated person in America with a lot of advantages. I do not worry about my future. I just don’t. I put myself in a relative stack ranking of the world, and for me to complain? I don’t want to minimize anybody’s experience — the richest man in the world can be super unhappy and should be able to articulate it. But I don’t worry about it too much. I don’t feel like I’m going to be unemployed. And by the way, I can do anything else. I’m good at waiting tables and I’m a hard worker.

WWD: I always think that, too, not with as much confidence, but that I could go back to waiting tables and retail and making coffee, whatever.

K.S.: Right. And more to the point, I’m entrepreneurial. I’m always like, I’ll figure it out. One of the reasons I sort of struck out on my own, and I’m still not an employee, is because I’m a bad employee. I’m not a good employee.

WWD: Because you’re so independently minded…

K.S.: Yes…

WWD: … or you don’t like being told what to do, or a mix of those things?

K.S.: Listen, it’s harder to do it as a woman and there’s no two ways about it. I’m comfortable doing it as a woman, but there’s a definite price to pay to speak your mind. And I don’t mean just saying whatever you feel like, because that’s not what I’m doing. I’ve said this before, I’m really good at saying, “No.” “No, I don’t want to do that.” I’m not particularly good at pleasing, but I’m very honest, I guess. Sort of like Cordelia in King Lear, “Love, and be silent” — don’t ask me to be effusive.

I’m pretty sensible. And most people who are good, when I say, “I’m not going to do this and here’s why,” it’s hard to argue. So, I say “no” a lot and that requires knowing yourself really well, and I think a lot of people don’t actually.

WWD: With this newest podcast, you’re talking some broader issues now, it’s not tech focused at all. Is that something you’ve been wanting to do, move away from tech?

K.S.: Yeah. I’ve been moving out of tech for a while. In “Recode Decode” I interviewed all kinds of people. And I always feel like technology impacts everything. It’s sort of like, what did trains have to do with back in the day? Everything.

[Walter] Mossberg and I, we always understood the reasons we were successful is it wasn’t about the tech, it was about the impact of the tech. I remember him telling me when I started, (he’s the one that got me to The Wall Street Journal), he said, “Parachute in with cleats on when you do your journalism, that’s what you have to do to get noticed.” The more I thought about it…I remember thinking two things. One was, I’m not going to tell you how the watch works. I have to know how the watch works, but I’m just going to tell you what time it is — that’s the critical element of a watch, right? But people tend to tell you how the watch works when people just want to know what time it is.

WWD: Yeah, the machinations of a watch aren’t super compelling…

K.S.: You need to understand it. You need to know which chip or whatever, but for the most part, no one knows how a car works but everyone knows what it does, right? At the same time, I don’t like to insult the tech. When I saw the iPhone I was like, “Ohhh, it’s finally here.” I’d seen earlier iterations of it that didn’t work, but everything met in that moment and I was like, “OK, everything is gonna change.”

WWD: You’re known as one of the first people to start covering the Internet and you were the first at the Journal, so was there a moment early on where it came to you these industries and companies would be so powerful?

K.S.: Yes. Well a couple of times. I’m very attuned. I studied propaganda at Columbia, at the journalism school my thesis was on that. I was in the Foreign Service school [at Georgetown]. I was very interested in communications and these windows where people see each other and I was very attuned to how things change when a technology comes in, whether it’s the telephone or the radio or the telegram. I studied all that. One of the first articles I wrote for the Journal in fact was about “cutting the cord…”

WWD: Oh, wow.

K.S.: I was like, “Wireless is gonna be everywhere, you don’t understand!” “No one is going to have a home phone and here’s why.”

But the moment I got it for, at least, the Internet was at The Washington Post. They had reporters go down to Duke and teach different courses, it was like a rolling thing. I was using their system. I downloaded a book and it caused a lot of problems with the system because it had pictures. I think it was “Calvin and Hobbes.” It took a long time and it messed up the network, but I remember thinking, “I downloaded a book.” Sort of like when Willy Wonka did the chocolate bar into the TV. I think the tech person there was like, “So what?” and I was like, “Are you kidding me!”

It was like, “Whoa, whoa, whoa.” This means you can download any song, you don’t have to carry everything, you don’t need a bookstore. And I covered retail then. The motto I eventually had was, “Anything that can be digitized will be digitized.” I started ranting about it and everyone was like, “Kara, shut up.” The same thing with mobile phones. When I saw the first one, I was, “Like, look at this! You can walk around, you don’t need to be at your desk. You can go anywhere!” And I never liked being at the office so I was like, I’ll take that.

WWD: Please and thank you.

K.S.: Yes, and I did, I carried around one of those suitcase phones. So, I kept saying, “Do you understand what this means for classifieds? Do you understand what this means for anything, anywhere?” Electricity is still the most important thing of all, FYI, nothing works without electricity, but I think I was one of the first people to see the Internet as this is the next one, people have been waiting for this.

WWD: And did people think you were crazy?

K.S.: It’s so funny, I don’t mean to drop names but I used to be friends with the woman who started “The L Word” and I was with the whole cast somewhere in San Francisco early on and I was like, “Twitter is going to be enormous!” And they were like, “What?” And I told them you’ll need to be on it and have a personality and this and this. Jennifer Beals was like, “What the hell is Twitter? Go away.” And just recently at lunch she was like, “You’re the person who yelled at me about Twitter.”

I’d also yell at them, “Don’t you understand Hollywood is going to be upended by streaming!” Same thing. I was invited to Sundance one time as the one tech person.

WWD: Nice.

K.S.: This was many years ago, in the early 2000s, I think. I brought in Reed Hastings, Jason Kilar, now the head of Warner and he was head of Hulu at the time, and Chad Hurley, who founded YouTube. I was like, “These guys are gonna change everything! Everything is gonna be streamed and downloaded and you’re not gonna go to theaters.” They put us in the basement.

WWD: No.

K.S.: It was an amazing group of people and they put us in the basement. I’ll never forget. And I must have seemed like a crazy person and they did, too.

WWD: You must have been frustrated with news leaders at the time, since you were already thinking about classifieds.

K.S.: Well, I think now they’ve gotten the message. When I was covering retail at The Washington Post, a lot of department stores in Washington were closing. Of course, the publisher hated me because every day I was coming in, “Guess what advertiser is going under now!” He was lovely, Donald Graham was always a gentleman, but he was always like, “Oh, you again.”

WWD: And this was the early Nineties?

K.S.: Yeah, must have been. So I was writing about retail and I wanted to get off the beat for a number of reasons, but one of the things that prepared me was things can die really quickly. So when I started to cover the Internet beat and started to see things like Craigslist, and there were other, earlier versions of it. So, I’m talking to Donald Graham and like, “Your business is f——ked.”

I was very much, “This is over and I need to move to higher ground.” I went to the Journal, which I thought was less troubled because I thought business people needed to have it. Even though they were still focused on print. I couldn’t care less for print.

WWD: You sound like a very pragmatic person. Strategic and pragmatic.

K.S.: Yeah, I am. When I said “blog,” that I wanted to start a blog to my then publisher at the Journal, she was like, “What’s a blog?” I was like, “It’s gonna kill you, that’s what it is.”

WWD: Literally murder you in your sleep.

K.S.: A bullet coming at the heart of journalism. You might wanna duck.

WWD: So, was starting Recode just you wanting to get out of print altogether?

K.S.: Oh, we wanted to start Recode in 2001, somewhere around there, maybe 2000. Right after the crash. A nice time to ask for money. But they wouldn’t do it because they didn’t understand it and so they let us do the conference.

Walter Mossberg was such an important part of the print publication’s ad revenue, he made them so much money with his column, they let him do whatever he wanted. And the conference was instantly lucrative and profitable. But we didn’t do the blog for five or six years. They wouldn’t let us.

WWD: How did you connect with Mossberg — was it just on a personality level right away?

K.S.: I interviewed him for my book on AOL in the mid-Nineties. He was the first person I saw eye to eye with. We were like, “Oh, do they see the iceberg?” And I knew all the new players and he knew them too, and the older ones like [Bill] Gates and [Steve] Jobs and Andy Grove, too. And he was like, “You need to work for us. You’re talking about the future.” So he kind of forced me on the Journal, on Paul Steiger. They were not resistant, they understood, but some people inside certainly were.

WWD: With your pragmatic personality and sense of forward motion, what’s been the impetus to stay in journalism this long? I mean…

K.S.: I know. You’re right. I should’ve taken that job at Google, Amazon, whatever. I’ve been offered a job at every major Internet company.

WWD: I’m sure…

K.S.: Good jobs. Really good jobs. Ted Leonsis — who owns however many friggin’ sports teams — every time I see him he’s like “Ehh, you could’ve had $100 million, Kara,” and I’m like, “I could’ve had $500 million, Ted. A billion.” I was right there. I was there with Elon when he didn’t have hair. I walked around looking for office space with Jeff Bezos for the first Amazon office.

WWD: Wow.

K.S.: I’m an idiot, I don’t know what else to say. I think it was Amazon, they asked me to come be editor, they were going to do some editorial stuff, and I was like, “Why do I wanna work there, when I work at WSJ or wherever.” I think it was Joy Covey who was like, “You might make some money.” I was like, “Ehhh, how much can you really make?” I’m an idiot.

WWD: You’re obviously smart. Maybe it’s that you’re not really after money?

K.S.: I’m really not. My family had some money. Not a ton, but were very, very…

WWD: You were fine.

K.S.: We were fine, yeah. I could’ve been a lawyer, I could’ve gone into investment banking. I just didn’t. All my friends went off to that in the Eighties after college and I didn’t. I was just like, “Oh, God, I can’t stand it.” I have this expression I often use with really rich people when they bother me, when they do something really terrible, and they try to push that they are so successful, so I should listen to them. I always go, “You’re so poor, all you have is money.”

I like money. I like earning a lot of money in my profession. But I don’t spend a lot of time thinking about how to make it. I make good money, that’s the thing. When I was doing podcasts, it was very important that we made a lot of revenue, like millions. Or the conference. I want it to be a viable business, mostly because I want to provide jobs and I want to do what I want. That’s more my motivating factor.

WWD: So it’s the freeing aspect of it for you.

K.S.: Yes, right. I don’t really care about clothes — I’m the bane of my mother’s existence. I don’t party. I don’t like cars. I like a nice vacation, but I don’t have to stay at the fanciest palace. There aren’t a lot of things that I want. I use Amazon like everyone else, but I consume experiences and restaurants. Other than that, it doesn’t really matter. I have enough money.

WWD: Do you think that kind of disregard for insane levels of wealth allows you to be a tougher interviewer?

K.S.: No, because I’m proud that I make money. But do I care that I’m not as rich as them? Nooo.

WWD: Or because you’re not intimidated by it, like a lot of people?

K.S.: I’ve never been intimidated by money. I grew up in Princeton, N.J., in a very wealthy environment. I don’t consider it the thing that sets anybody above anybody else. I don’t think it makes you better.

I am intimidated by intelligence. I was just reading a Judith Butler interview and I was like, “Ugh, I’d like to interview her but I’m not smart enough.” She’s so smart and I’d need to really study. She’d catch me.

WWD: Is there anyone you’ve interviewed that you felt nervous about or intimidated by?

K.S.: No. No. After Steve Jobs, he was such a snark test.

WWD: Have you ever been bothered after making someone mad by your reporting, like intimidated or followed or anything like that?

K.S.: No. Ohh, one time. I wrote about a guy, he was terrible. He had an assault around women and I wrote about the board firing him and he got into his brain that I convinced the board to fire him, which I didn’t. He sent me a series of really disturbing e-mails and texts. He was a paper tiger in that regard, but it was irritating. There was another time someone with some mental problems blamed me for his firing. Again, the boards did these things. Some of my reporting is so tough it could sway people toward seeing this person is incompetent.

But besides reporting about some things, I actually say, “That’s wrong.” You know what I mean? I definitely think I have an impact on people’s attitudes.

WWD: You do often come out and say this is wrong, but being at some of the biggest papers in the country, stalwarts of “unbiased journalism,” I’m wondering how you navigated that?

K.S.: That’s why I did “All Things D.” I was tired of that. I hate that, “unbiased.” There’s no such thing, FYI. But you don’t have to be unfair and you don’t have to be wrong.

WWD: Was it always your ambition to be a reporter, you mentioned being in the foreign service school…

K.S.: No.

WWD: What did you want to do?

K.S.: I wanted to be a spy in the CIA. Or military intelligence. I wanted to go into the military. My dad was in the military. He died when I was young. He’d just left the military; it put him through medical school and college. He was in the Navy. But my family, the Swisher side, has quite a few military people in it and I always had great regard for the military and I thought it would be great. Only gay people want to be in the military and get married. “Please let us marry and go into the military!” The straights are like, “Get us out!”

But then you couldn’t be in the military unless it was Don’t Ask, Don’t Tell, one of the worst things President Clinton did. And I’m not a don’t teller, so. You ask, I’ll tell. I just couldn’t do it and I was really sad. My whole life I wanted to do it and by the time they finally passed a 100 percent you can be gay whatever, I was too old. I sort of missed the timing of it and then I got off onto this.

WWD: So, how…

K.S.: I’d be a general by now, probably working for Trump.

WWD: Oh, God…

K.S.: Leaking.

WWD: OK, yeah, you could’ve done that.

K.S.: Well, I would’ve quit and then I would’ve talked, unlike these stupid men who aren’t talking. I would’ve been like [Alexander] Vindman.

WWD: That would’ve been great. But how did you get off onto this, journalism?

K.S.: I worked on my high school yearbook and my college newspaper and I did really well. I won a bunch of awards there. Then I worked for The Washington Post in college. I got into a fight with one of their editors and they hired me. I was a stringer from Georgetown. Then I was a news aide and a night aide. I worked my way up from the mailroom. I worked there for a while.

WWD: When you were coming up, it seems like it was a different time culturally. Did you find it particularly difficult as a woman, as a gay woman?

K.S.: As a gay woman it’s easier. I was out for most of the time, so people always knew. I found men felt relieved around me for some reason. I never felt discrimination about being gay in the newsroom. There is discrimination in all newsrooms on lots of different levels, largely because it’s run by the same 26 old white men, but I didn’t suffer that. I was aggressive. I was curious. I was hardworking, still incredibly hardworking. I had all the attributes of what makes a good reporter. Most of my mentors have been men. David Ignatius at the Post was great. I haven’t felt hindered, but I’ve definitely seen people hindered. A few times.

When I did suffer was after I had a baby. I was pregnant with my oldest, on the Internet beat at the Journal, and I broke all the stories and I worked almost until I had the baby. The Journal had terrible leave programs. When I got back, very soon after, one of the high-ranking editors here sat me down, he says, “Well, you’ll need more time now.” and I go, “Why, because I had a baby? You have three children, do you need more time on the test?” That was the first time I sort of saw, this is what happens to women. This concept that they can’t keep up, which they certainly can, because they do. And I actually worked harder then because I saw that was the perception.

WWD: Do you feel that was fair, or it was just what you had to do?

K.S.: I’m a hard worker. I would’ve done it anyway. But no, people shouldn’t. It’s not just for women, it’s for parents.

WWD: What is it about podcasting that got you excited again?

K.S.: I was tired of beat reporting, definitely. I’ve done so many midnight calls with moguls lying to me. There was a point where it just wasn’t much fun for me.

I’ll tell you when it really changed for me. I was in the Muni in San Francisco (I like public transportation) and these four women came up to me, young women, all African American. Not my demo, let’s just say. My demo is a young, white guy, totally nerdy or else a real slick business developer guy, always a guy. And these women are like, “Oh Kara Swisher, we love you!” and I was like, “What? Why? Who? What? What do you love?” They were all entrepreneurial women doing a makeup company online. Not tech. They just loved entrepreneurism. And I felt like I was really helping them, what I’m doing has a real impact, in a really good way. There’s something in the podcast genre that changes people’s mentality toward a reporter. Because I think they trust podcasters more, you know what I mean?

WWD: Yeah, you’re lifting the veil on the process a bit.

K.S.: Yeah, and I can’t hide when someone comes back at me. I can’t trick or manipulate words. It’s whatever I say and then I have to live by them. And then when “Pivot” happened, crazy fans. People love Scott [Galloway] and I arguing. They love it. Scott was going to the Hamptons, as he is wont to do, getting on one of the helicopters, as he is wont to do. Kara does not do this. And one of the helicopter guys goes, “Where’s Kara!” He’s like, “What?!”

I’ll walk through San Francisco and even [Washington, D.C.], “Where’s Scott?!” I say, “I don’t hang out with that a–hole.” It’s just funny.

WWD: Do you feel like this will satisfy you for a few years or…

K.S.: Probably not.

WWD: Are you still planning to run for mayor of San Francisco in 2023?

K.S.: No, no I’m not. Maybe if we move back but, no. You know what — they have a good mayor now that I like.

And the other thing is, it’s too exciting now in Washington with all that’s going on. Finally after pushing all these years, they’re doing what I’ve been suggesting. And I might find something else interesting. I signed a two-book deal and I resisted that for 20 years.

Jonathan Karp, who was my original editor on my AOL book, he’s the only person I would’ve done it for. I got a lot of offers. And so I was just like, “Oh, all right I’ll write a memoir.” Then I thought, I kind of really do want to write a memoir. I have all the receipts. And now I don’t care. I’m gonna tell you what it was like at the fair. I’m gonna really tell you. And then I’m gonna go and, “Goodbye.”

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