Tech journalist, opinion leader, and disruptor—Kara Swisher has hosted hundreds of newsmaking interviews tracking tech and media’s changing power dynamics, often going head-to-head with the most prominent figures in the technology industry. She joins a live studio audience to talk about her inimitable career covering the ever-evolving world of technology.
Roxane Gay:
Kara Swisher is truly a woman with her finger on the pulse of all things tech. She has written for countless publications, including The Wall Street Journal and The New York Times, but now she hosts the podcast On with Kara Swisher and she co-hosts Pivot with Scott Galloway. With inimitable style, she covers breaking news, opines on technology companies and the mercurial people who lead them, and is always, always ahead of the curve. Tonight, she joins Debbie Millman and I on this live episode of Design Matters. Kara, welcome to Design Matters Live.
Debbie Millman:
Hello, Kara.
Kara Swisher:
Hey, they totally all saw us come in on the side, so.
Debbie Millman:
I know.
Roxane Gay:
The secret’s out.
Debbie Millman:
We were like, “Well, that’s an anti-climax.” Kara, I think that you might enjoy this first question.
Kara Swisher:
Sure. I might.
Debbie Millman:
You might. Given the conversation we were having backstage about cars, is it true you have a special affinity for the Ford Fiesta?
Kara Swisher:
Yes, I do. I do. I love the… I had a Ford Fiesta Turbo, let me just say. People made fun of me and then I took a minute, which was a very different experience. It was also a manual. I drive manual when I drove gas cars, and I love manuals. My 12th grade boyfriend taught me, that was a long time ago, taught me how to drive a manual and I love it. And I love driving it at San Francisco downhills. And I’d pretend I was going backwards with my kids, and they’d be like, “Mom, stop.” But then I did it anyway. And then since, I have now a Chevy Bolt. In my ongoing series of sexy cars, I have a Chevy Bolt and a Kia Sorento. So, I am one hot lady.
Debbie Millman:
Good logo on that Kia. Nice new logo.
Kara Swisher:
I love my Kia. It’s a hybrid. It’s nice.
Debbie Millman:
Kara.
Kara Swisher:
Has three seats. Three sets of seats too.
Roxane Gay:
Oh, I always enjoy a third row for-
Kara Swisher:
You know what?
Roxane Gay:
… activities?
Kara Swisher:
Yeah, I have-
Roxane Gay:
Just saying.
Kara Swisher:
I have four kids, so I need it. So, yeah.
Debbie Millman:
When your dad was 34 years old, he died from complications of a brain aneurysm.
Kara Swisher:
Yes.
Debbie Millman:
He was fresh out of the Navy. He had three kids. He and your mom had purchased their first house. He had landed a job as the head of Anesthesia at Brooklyn Jewish Hospital. You were five years old.
Kara Swisher:
Indeed.
Debbie Millman:
And have said that his sudden death has informed everything you’ve done since.
Kara Swisher:
Yes.
Debbie Millman:
And I’m wondering in what way?
Kara Swisher:
Well, in every way. I think when your parent dies at a young age, there’s a great book, I think it’s by Irvin Yalom or something called The Loss That is Forever. I love this book. A friend of mine’s lost her daughter who has this young child, and I sent this to them, or I advised them to get it. When your parent dies at a young age, it’s as if half your friends have died because that is your touchpoint at that age. And at that time when it happens, it’s devastating, but you get through it. You do. You just do. And so, a lot of things don’t matter as much as, because you realize, one, you get a sense of mortality at a very early age. And two, is you can survive a lot of stuff.
And a lot of people have gone through worse things, but it certainly was tough. And it was accompanied by the fact that my mom married someone who wasn’t very nice. My father was incredibly kind, so I felt like I’m essentially living Cinderella or something. It was like that. And so, it makes you think every time. I think about death a lot, not in the way I’m going to die tomorrow. It’s that I’m always like, “Should I do this? Oh, I’ll be dead in 50 years. Yes.” And so, it tends to give me a positive spin on every… I don’t have as much… I just don’t have that kind of time, and neither does anybody else, but I have a very good sense of that.
The other thing is when I had my first child, who’s now 21, I have right now, also a four-year-old, someone about to turn four daughter and a son who’s about to turn two. And when my oldest, who’s now 21 turned five, I realized the devastation because we were incredibly… I’m incredibly close to my two-year-old, knows me well, walks home, “Hi, mama” and hugs me. It just informed everything. So, I think it made me bolder and highly functional, I would say. Highly functional, and my brothers are highly functional. It’s not great. It’s not a great way to learn that but…
Roxane Gay:
You’ve noted that when you survive something that awful, very little is going to bother you over the course of the rest of your life. And it seems like that has held true this many years later. And so, why do you think that holds true for so long? And do you ever foresee that changing where things might start to rock your world again?
Kara Swisher:
Well, only around my kids, I think. That’s the only time I get panicked about something happening to them and traveling. That’s the only thing. I think I had kids because I didn’t want to become one of those people that nothing bothers. I think probably a lot of my earlier relationships I was like, “Yeah, we break up. Oh, well. So, what?” You know what I mean? You get like that.
Roxane Gay:
You had a perspective.
Kara Swisher:
Yeah, it’ll be fine. Everything will be fine. I’ll be fine. And I think having kids does give you a sense of vulnerability that you can’t avoid. Not everybody has kids. I get it. There’s different ways to do that. But for me, that’s the one thing that gives me a sense of terror sometimes or scaredness. I’m not scared for myself. I’m scared for them, especially because I knew it does give me insight into what happened to me too at the same time.
So, I guess that would be… It doesn’t leave me though. Every time, you know me, I leave things when I don’t like, if I don’t get enough money, or if someone just bothers me. We were talking about someone we know jointly and when I left this particular thing, they said, “Why are you leaving?” And I said, “I don’t want to talk to you anymore.” And they were like, “What?” And I go, “I just don’t want to see you anymore also or encounter you, or I got to go.” And it was because of that feeling, of like life’s too short. It’s more than life’s too short. It’s like I have this many minutes on the planet, I don’t know what it is, but you’re taking up far too many of them and you need to move along, out of my sight.
Roxane Gay:
I have to say, yes, please clap, when I hear something like that, it feels a bit mythic because I am not… Even though on the page, yes, I’m absolutely that bitch, but in my day-to-day life, I don’t have that thing that allows me to just say, “I don’t want to ever speak to you again.”
Kara Swisher:
Yeah, it’s easy.
Roxane Gay:
How do you develop that? Or it’s just-
Kara Swisher:
It’s easy. Just start doing it and it’s like… Because I do a lot of, “Yeah, no, no, I don’t think so.” I was going to do a series of books and I still might. We just thought of a podcast to do together. We’ll talk about-
Roxane Gay:
Yeah, it’s going to be amazing.
Kara Swisher:
It’s going to be epic. It’s so unlike what you think it would be. It’s not badass ladies. It’s something much worse. But I am going to do a book and it’s called No is a Complete Sentence. And the second book in the series is called Yes, I’ll Take That because I don’t think women say… It’s a book for women and other people who need it, essentially. And the third is Maybe I’ll Call You Back. Yes. I don’t know. I never regret saying things. I don’t. People are like, “Did you regret that?” I’m like, “No. No. I like that. That was fun.”
Roxane Gay:
Wow. Well-
Kara Swisher:
Someone’s going to shoot me someday. One time, I was in… Because I’m mean to some of the tech bros and they have a lot of money. I was in New York and I was crossing the street. And a car made a 180, a big black car, like one of those big Ubers, this whatever, and stopped in front of me. And I literally thought the time has come for Peter Thiel to kill me or Elon Musk/Mark, just that they have sent in the Israeli secret people that are going to now take me. I’ll be cut up into little pieces and spread around the ocean and stuff. And I thought that I got one too many insults of these adult toddlers, and I just did it again. And it was a fan. It was a fireman from Queens. And he’s like, he wanted a selfie. And he goes, “Did I scare you?” And I’m like, “Yes. Now, you have to abduct me and cut me into tiny bits.”
Roxane Gay:
Now, this is taking a step back, but I know that your mother is very stylish and so was your Italian grandmother.
Kara Swisher:
She was.
Roxane Gay:
And at one point your mom worked at the great old department store, Bonwit Teller.
Kara Swisher:
She did because I was there a lot.
Roxane Gay:
Amazing. And later had her own store and would coordinate fashion shows. You’ve said that you are her greatest disappointment in that regard. And I can relate because my mother is also very fashionable and every time she looks at my wardrobe, she’s just like, “No.” So, has your mother truly never appreciated your style?
Kara Swisher:
No, never. She hates that. Sometimes she’s like, “That was okay.” But no, she’s a fashion person and really quite fashionable, and I have no interest. And interestingly enough, we were talking on the podcast today because of the John Fetterman controversy, like who the hell cares if he wears shorts, honestly. My favorite tweet about this, or it might have been tweet, was “Joe Manchin, thanks for wearing a suit. Well, you voted against the child tax credit.”
Roxane Gay:
I saw that and I agree.
Kara Swisher:
I agree. Nice outfit.
Roxane Gay:
All of these old men who frankly don’t know how to tailor a suit are talking about a dress code. Leave him alone. Leave him alone.
Kara Swisher:
No, I agree. I think it’s a bad thing. I think John Fetterman’s handled it really well. I get their point vaguely, but in general, no, my mom really hates my clothes. And since the pandemic, it’s gotten worse because I… I’m wearing hard pants right now, but I’m usually in soft pants. I hate hard pants, but I’m wearing them for you. But soft pants are my thing.
Roxane Gay:
Oh, thank you. I think both Debbie and I-
Kara Swisher:
I love soft pants.
Roxane Gay:
… are honored that you brought out the hard pants.
Kara Swisher:
I don’t like hard pants.
Debbie Millman:
Absolutely.
Kara Swisher:
I hate hard pants. They’re terrible.
Debbie Millman:
It’s really funny because I was thinking I was going to put on heels and the whole thing. And I was like, I think Kara prefers the more casual.
Kara Swisher:
Yeah, you look good though, but it’s fashionable. My mom would approve.
Debbie Millman:
The shoes.
Kara Swisher:
She’d like those. I think those are expensive, I believe. Correct?
Debbie Millman:
Not really.
Kara Swisher:
Okay, but they look like those.
Debbie Millman:
But I actually wore these for you.
Kara Swisher:
Oh, thank you.
Debbie Millman:
Women dress for each other. That’s what we do or don’t.
Kara Swisher:
I just want to tell you, I didn’t notice. I didn’t. I didn’t.
Roxane Gay:
I did.
Kara Swisher:
I didn’t. I wear the same things. I literally wear the… I have had… I went back and saw some friends of mine that I’ve known for 50 years really. And they’re like, “You’re still dressing the same.” I’m like, “It’s the same shoe.” It’s like I have clothes that I’ve had for 40, 50 years and I love them.
Debbie Millman:
We found out that you have-
Kara Swisher:
I guess I’ve stitched up-
Debbie Millman:
… a lot of the clothes you wore in eighth grade.
Kara Swisher:
Yeah. I have a lot of them that I wore in eighth grade.
Debbie Millman:
Do you still wear them?
Kara Swisher:
Well, now, yes, I do. Of course, I do. And then of course, now I wear my oldest son’s T-shirts from when they were in eighth grade, so I just had one. It was too long because he was taller than me at that time. So, I just had them hemmed a little bit. And there was a big stain of unknown origin, so I had it just cut. And now, I’m going to wear it. Yeah, it’s real old. My mom will hate it. My mom will hate it. It is yellow. She likes the color. It’s an ongoing war, a fashion war with her, but one time, she bought me some. She buys me clothes all the time. To this day, I’m like, “There’s got to be an end to this.”
Debbie Millman:
What kind of things does she buy you?
Kara Swisher:
Oh, expensive clothes, whatever happens to… Just very expensive fashion forward clothes. And I’m literally like, “Have you met me? Never.” But one time, she bought me something that was yellow, and I don’t like the color yellow. I don’t like wearing it. I mean, it’s fine as a color, but I don’t want to wear it. And she goes, “I bought you this.” And I go, “Mom, I hate the color yellow.” And she goes, “No, you don’t.” That’s our relationship in… That’s our entire relationship right there.
Debbie Millman:
Tell Kara and the audience that-
Kara Swisher:
She’s going to listen to this. And she’s like, “Stop talking about me.” I said, “At least I didn’t talk about your ridiculous obsession with Fox News.”
Debbie Millman:
Ooh. Well, I think you should share it with Kara and the audience, the conversation you had with your mom last night about your-
Roxane Gay:
Oh, for Christ’s sake.
Debbie Millman:
Well, Susan brought up the book, so you might as well.
Roxane Gay:
Yes. So, my mom is… I love her. We talk every day. She’s very special. She’s Haitian and she’s 74, and she just does not give a fuck about anything. She will say whatever she wants to say, and this is not an elderly thing. This is just who she is. She’s always been this person. I was telling her about some good news about a movie I wrote that’s actually going to get made. And she was like, “Oh, good, then maybe now people will learn your name again.” Because it has been five years since I published a book. And I was just like, “Thank you for having the appropriate reaction.” I was just, oh. I was so stunned. And I was like, “Do you even read The Times?”
Debbie Millman:
She was joking.
Roxane Gay:
I publish all the time.
Kara Swisher:
Oh, no. And you’re still doing it with your mother. You’re like, “I really am famous. I am.”
Roxane Gay:
I know. And then I’m defending myself. And the thing is, she comes up with us to my events all the time. And so, it’s so funny. And then my dad will be like, “You know, Roxanne, I saw Bad Feminist in the store and I would like to see something else next to it.” And I’m like, “Well, we have the same last name.” “So, perhaps you should write something.”
Kara Swisher:
Yeah, and I appreciate it. I mean, we’ve had our struggles, but she escaped from an assisted living facility. I put her in a very nice one, the nicest one in America, but she left. She just left. She somehow got my neighbor in San Francisco to help her, and then she was on the Queen Mary with her going to England. And I was like, “Where are you?” She goes, “The Queen Mary.” I’m like, “What? What happened?” So, I’m just saying she does…
Debbie Millman:
Wow.
Kara Swisher:
But she’s always been… It was nice to have her, actually, when I was doing big events because she would also insult billionaires without the drop of a hat.
Roxane Gay:
That’s a handy skill.
Kara Swisher:
Yeah. One time, we used to give out swag to people that came to the conference and Bill Gates was in line. And it was, I think, a Guitar Hero at the time or whatever, a free Guitar Hero. And my mom helped give stuff out. I used to make her work for showing up because she got to stay in the nice hotel rooms. And she looked at him and she goes, “Can’t you afford this on your own?” And then one time, the guy, Intel, with Andy Grove, he goes, “I am Andy Grove. I created Intel.” She goes, “Never heard of you.” And then she went on to eat a pig in a blanket.
Debbie Millman:
You know that podcast idea you had?
Kara Swisher:
Right.
Debbie Millman:
I actually think it would be better for your mothers to do it together.
Kara Swisher:
Yes, that’s true.
Roxane Gay:
Oh, I’m sure they would have quite the time.
Kara Swisher:
Yes, exactly.
Debbie Millman:
Well, speaking of mothers, Kara, I understand that you knew you were gay when you were four years old.
Kara Swisher:
Four years old.
Debbie Millman:
Bravo, by the way.
Kara Swisher:
Thank you.
Debbie Millman:
But didn’t come out to your mom.
Kara Swisher:
You were a little later, right?
Debbie Millman:
50.
Kara Swisher:
50, wow. Come on.
Debbie Millman:
Very different upbringings.
Kara Swisher:
Come on.
Debbie Millman:
Very different.
Kara Swisher:
I don’t believe you.
Debbie Millman:
Oh, I swear. I swear.
Kara Swisher:
Wasn’t there like a field hockey coach, you’re like, “Mm.”
Roxane Gay:
Oh, well, I think she’ll admit she came out at 50.
Debbie Millman:
I dabbled pre-50. I call it dabbling. I dabbled. But yeah, and I mean, you and I are the same age, so I think you know how it was sometimes scary to-
Kara Swisher:
No.
Debbie Millman:
No? For me, it was scary. I grew up in a somewhat homophobic environment.
Kara Swisher:
Yeah, me too.
Debbie Millman:
Yes, I know. When you told your mother, she told you… Well, you said that you told her in a spectacular way over the phone.
Kara Swisher:
Yes, I did.
Debbie Millman:
I want to know what that spectacular way was. But at that point, she told you she would never speak to you again and then wouldn’t stop speaking to you for the rest of your life.
Kara Swisher:
Yes, exactly. I knew it was an empty threat. She’s full of empty threats, so that’s why I’m like, “Yeah, whatever. Sure.”
Debbie Millman:
So, what spectacular way did you tell her?
Kara Swisher:
I always said, every now and then, and I think I’m going to forgive her, but one of the… Because people grew up. You have to at some point say, “Okay, this is how they grew up.” Although my grandmother was fantastic. She’s like, “Yeah, I knew.” And then she was like, “Yeah, whatever.” And then I was going out with someone and she’s like, “Mm, she’s too pretty for you.” My grandmother said that. And I was like, “You know, she is. Yeah, that’s fair. That’s fair.”
Debbie Millman:
But what about the boy in 12th grade?
Kara Swisher:
He was a nice guy. He’s a good guy, actually. I had a lot of boyfriends, actually. But what happened was, she’d say little things like, “If you were gay, I won’t speak to you.” That was the kind. You know that kind. I was like, “Okay, got it.” And I always promised if she said it to me, asked me directly, I would answer directly. And I was going to dinner with someone, I think I was 22 years old or something with the person I was seeing at the time. And we were just going out to dinner for my birthday. And she’s like, “What are you doing for your birthday?” I said, “I’m going out with this woman.” And she goes, “Alone?” And I go, “Yeah, that’s right.”
This is this phone call. You can hear that. And she goes, “It’s almost like you’re going out.” That’s what she said that you’re going out. And I go, “Mom, you have won the Chrysler Cordoba. You finally had the guts to ask the question you’ve always wanted to ask, and you’ve been spinning around. You win. Fantastic.” And then she said the most horrible things to me. It was terrible and said she wouldn’t speak to me and this and that. And I had had to go up to New York for a family thing that weekend, which was really uncomfortable. And what happened is, it’s an Italian family, so there’s a lot of strategy going on with this group of people.
And so, I immediately called my brothers, my grandmother, I got everyone in line on my side, and she was too late. I was too fast with the phone. And so, I went up and I had to see her. She tried everything, “You don’t like men?” I’m like, “I love my brothers. I’ve had boyfriends. I like men. Why would I…” There’s an old joke. Lesbians don’t hate men; they don’t have to sleep with them. And I said that joke. She didn’t like that. It didn’t go over well. Then I tried a bunch of things like, “Hate man, I’ve got these…” I don’t know. Just one up, “The people will never speak to you.” I was like, “Everyone’s talking to me. They’re irritated by you.”
When you’re in that relationship, you know where you have to have your ammo essentially. And over time, she got better because she was actually getting a divorce from my stepfather and she needed me. And so, very soon after, she needed my help. And so, I think that was better. But it’s been a struggle until I had kids. And even after I had kids, she was difficult, I would say. And she would buy worse presents for my girlfriends, which drove me crazy. And I would make her take them back and get a better present.
And whenever she did something nice, she goes, “See, I’ve been nice.” I’m like, “We don’t negotiate with terrorists. You have to behave.” The whole thing, I would do that. I was really tough on her. And even when I had one of my kids and obviously adopted the other, my ex had the other one, before the kid was born, she was like, “I’m not a grandmother.” That kind of thing, stuff like that. But she loves all the kids. It just didn’t stick once you start to get the familiarity.
And then the only time we really had a very bad situation, two times, was when the New York Post wrote about my pregnancy and I hadn’t told her. And I had to tell her because she’s a very big reader of the New York Post, and it was on page six in the J Lo’s marrying someone else position. And it had things about sperm donors and this and that. And then the Post called me and said, “We’ve heard the father is Jeff Bezos.” I was like, “I can’t accept anything more than $25 from anyone I cover. So, no, that’s not the case.” So, I had to tell her, and she wasn’t particularly nice. She blamed me for the item because all her friends would find out, essentially.
And then one other time, we were… Rick Santorum, remember him? He’s now just on CNN or maybe not anymore. [inaudible 00:20:52].
Debbie Millman:
Collective.
Roxane Gay:
I remember the alternative definition of Santorum very fondly.
Kara Swisher:
Okay, all right. I don’t know that, but you can tell me.
Roxane Gay:
It’s really unpleasant and it involves semen.
Kara Swisher:
Okay. Well, yeah, there you go. So, she lived in Pennsylvania. She had a Pennsylvania voting. She voted in Pennsylvania and was born there. And he was doing very anti-gay stuff there, including around adoption. I had one kid I adopted and Megan adopted the kid I had. And at the time, it was so much worse. We had so many legal papers. It was ridiculous and still not guaranteed parental rights. And so, I said, “You really can’t vote for him. You cannot.” She was a Republican voter. And I said, “He’s against our family. You don’t have to vote. You can write in my grandmother’s name. I don’t care, but you cannot vote for him. This is a very hard thing because he’s trying to pass this legislation.”
So, we were at Thanksgiving dinner in San Francisco actually, and we were talking about the election that just happened, and for some reason we were talking about voting. And she goes, “Well, I voted for Rick Santorum.” And I said, “Excuse me?” And I said, “You could not do that. You had to stick with our family and not this ridiculous tribalism that you have.” And she’s like, “Well, I can vote for whoever I want.” That’s what she said, which was incredible. And I said, “And I can give pumpkin pie to whoever I want. Get out of my house.” And so, I did. I made her leave and I wouldn’t let her see the kids for several months until she apologized to them.
But since then, she’s been great. She’s been a great grandparent. She’s got her quirks like everybody else, but she’s been really wonderful too. I’ve had two more kids since then. She’s been a wonderful grandparent to them.
Roxane Gay:
And speaking of grandparents, your grandmother was one of your favorite people?
Kara Swisher:
My favorite person.
Roxane Gay:
And you said that she was encouraging of your confidence. You’ve said it delighted her when you were yourself. How did that help you to stay confident, especially as a woman, as a gay woman growing up in a world where women are often told, as you well know, to make ourselves smaller?
Kara Swisher:
She was a housewife. She didn’t really do… She stayed in the same town, Old Forge, Pennsylvania, her whole life. She didn’t go very far. She didn’t like going very far. She was always watching the Weather Channel. She’s like, “In Vegas, it’s bad.” I’m like, “You’re never going there. What do you care about?” “Just giving you the update, Kara.” I was like, “Thank you, grandma.” And she watched football. She’s Italian and she was always loving, she always constantly loving. Not educated, I would say. We were very educated and I think she didn’t get… She may have graduated high school. I don’t think she got past ninth grade. Just a simple person and a person of their time too.
She kept calling my sister-in-Law, the Irish. Like, “Where’s David?” “With the Irish.” I was like, “All of them? All of them?” Stuff like that. But she’d like, “What are you calling me that for?” She’d sneak cigarettes, but she was always there for me in a way that was absolutely loving. And I think I just always felt that she had my back in a lot of ways throughout. And having your dad die and stuff like that, to have a very loving, no holds barred, unconditional loving person is critically important, I think. And she was funny. She was a funny… She was funny.
She was so sweet her whole life, and then when she got older, she got mean. Like something happened and she didn’t care. Not mean, but in a good way. And so, she would only eat chicken wings, black coffee, and doughnuts toward the end of her life. And I always go, “Grandma, you got to eat something healthy.” She goes, “Am I going to live 10 more years?” I’m like, “No.” And she goes, “I’m going to eat my doughnuts.” And I’m like, “Okay, fair.” And when she died, they have an open casket. Italians love to do an open casket, which I don’t love, but we put a chicken wing under her knee, wrapped. Her cousin did it, so she couldn’t reach it. So, it’s there now. If you want to go get something to eat, she’s above ground, so it probably is just a little desiccated.
Roxane Gay:
Oh, wow.
Kara Swisher:
Yeah, I know. I know, right? It was fantastic. It was so good. We have good funerals. We put the fun in funerals, our family.
Debbie Millman:
Kara, I have one more question for you about your early years.
Kara Swisher:
Yeah, this a lot. What is this, therapy?
Roxane Gay:
It is.
Debbie Millman:
In addition to running the playground, I understand you were the-
Kara Swisher:
Wow, you’ve done a lot of research here.
Debbie Millman:
… headmaster of the playground.
Kara Swisher:
Yes, I was.
Debbie Millman:
Once in elementary school, you were assigned some reading in class and then you stood up and declared, “I’ve already read this and I’m bored, so I’m leaving.”
Kara Swisher:
That’s correct.
Debbie Millman:
Which you did.
Kara Swisher:
Yes, I did.
Debbie Millman:
You’ve always been this version of Kara Swisher.
Kara Swisher:
Yes, exactly.
Debbie Millman:
This is who you are.
Kara Swisher:
But I had already read it. I was bored and I left. I think that’s fair.
Debbie Millman:
Where’d you go?
Kara Swisher:
I just went and found another book and stuff. I don’t know. Mrs. Jonathan was like, she didn’t… At this point, she’s like, “It’s Kara. She’s right. She read it. She’s bored. Get her another book.” And so, I read early. I was considered very, very smart at a young age, one of those kids. And then everyone caught up to me. I didn’t stay that way, unfortunately. But I was good at math. I was good at reading and stuff like that. And so, I just was like that.
My nickname among my family members, my Italian family members, was Tempesta, which I thought was good but insulting too. That’s what they call a girl who knew what they wanted.
Debbie Millman:
And so, have you felt like-
Kara Swisher:
It means… You get what it means, Tempesta.
Debbie Millman:
… you’ve always what you wanted?
Kara Swisher:
Yeah. Yeah. I’m sorry. I know I should be like, “No, I forget this.”
Debbie Millman:
No, no. Well, I know that you did want to work in the CIA.
Kara Swisher:
Yes, I did.
Debbie Millman:
And in fact, you declared that you would’ve been as good as Claire Danes in Homeland.
Kara Swisher:
Yes.
Debbie Millman:
But with 100% less mental illness.
Kara Swisher:
Yes.
Debbie Millman:
Now-
Kara Swisher:
As charming as that was, yeah.
Debbie Millman:
Was being gay the only thing that stopped you from applying?
Kara Swisher:
Yes. Yeah. Interesting.
Debbie Millman:
And would you be applying now for it?
Kara Swisher:
It was so interesting because I went to a wedding this weekend with people I’ve gone to school with since sixth grade, and one of the teachers was there and they said, “Oh, you used to tell me you were going to be really famous someday. You didn’t know what it was.” But I really did want to serve. My dad was in the Navy. I did want to go into the military. I have a patriotic streak. A lot of my family on that side is in the military. And I thought it was important. I don’t know why. I just did. And maybe because of my dad or something.
And I couldn’t go into that because of, Don’t Ask, Don’t Tell at the time. Thank you, Bill Clinton. Appreciate that. So, that was a problem for me. I couldn’t do ROTC. I couldn’t do early. I couldn’t go to West Point, whatever. I was going to probably go in the Navy. And then I thought the CIA, and it just was at the time, maybe you remember. Remember Clayton Lonetree? There was all these issues around the CIA and blackmail and this and that. And I had a friend who was in the Soviet Union who was gay and then got questioned and then thrown out of the country because it was blackmailable or whatever. And so, I didn’t want to have those conversations.
And so, it didn’t feel open to me without being closeted. And I have a real problem with a closet. I just think it’s such a nasty, toxic place. I hated it. I think we all were in that, right?
Debbie Millman:
Well, that’s what kept me from-
Kara Swisher:
Yeah. And so, it was just… I can’t believe we did. Today, it’s like when I was with one of my sons when he was young, and we ran into a payphone one time. It was a dead payphone, essentially. And my son was like, “What’s that?” And I said, “It’s a payphone.” And he’s like, “What’s it for?” I go, “Calling people.” And he’s like, “Well, how?” I go, “You put money in it and then you talk on it.” And he went, “That’s filthy.” And I was like, “It is.” So, it reminds me of that. I can’t believe we did all this skullduggery and all the hiding and the two… At one of my apartments, I think I had a fake room for my girlfriend, had a fake room. Like what is… The hours of your life you wasted doing that, it was so stupid, so people wouldn’t know. It was dumb.
Roxane Gay:
Yeah. It’s interesting to see how some people are able to just do that and then others stay in that place until they’re ready or until they’re shoved out. And it’s interesting.
Debbie Millman:
Hello.
Roxane Gay:
Yes.
Kara Swisher:
I respect that. I get people should come out when they’re-
Roxane Gay:
Of course.
Kara Swisher:
It was the AIDS crisis for me when I was in college and I was here in Washington. I was here after too and I remember doing the quilt on the mall. It was one of the folders, and I wasn’t a particular activist, but just at that point, I was like, “Fuck these people. They’re killing us. They’re killing our community.” And it just made me furious. And when I saw Angels in America, a lot of art, a lot of the plays that are going at the time, I was like, “What the hell? These people are dying for no good reason. And this is the United States of America. What is wrong? What is going on?” And so, I think that got me. I was like, “That’s enough. That’s enough with that.”
Roxane Gay:
So, you are out. You have seen the AIDS crisis during college, and I think for many of us, that was formative.
Kara Swisher:
Very formative.
Roxane Gay:
I went to school on the East Coast and we would go to New York on the weekends. ACT UP was very active at the time, and it was amazing to see that there was this way of fighting back, and that there were people who were willing to tell those stories. After college, you ended up going to Columbia School of Journalism to get your master’s degree. And you’ve said it was a waste of money. And I think most of us who have graduate degrees could probably say yes, 100%. Why did you think you needed a master’s degree to get into journalism?
Kara Swisher:
I don’t know. Because I got job offers from cities I didn’t want to live in as a gay person. You know what I mean? I didn’t want to go to Alabama. I didn’t want to go to most states. I felt unsafe, and I thought it would help me. I don’t know why. It was stupid. If I go back in a time machine, I’d take that money and invest in Apple stock and I’d own an island right now just like… Seriously.
Roxane Gay:
I wonder how much it would’ve been worth.
Kara Swisher:
I know.
Roxane Gay:
Oh, you do tell us.
Kara Swisher:
It’s like $60 million. It’s some crazy amount of money. Then again, I’ve turned down jobs at every internet company. So, I’ve lost billions of dollars that are owed to me, Kara Swisher. But it was a waste of money. I just was stupid. I could have gone worked. Working is the best way to do well.
Roxane Gay:
Did you learn anything useful in grad school?
Kara Swisher:
No.
Roxane Gay:
Okay.
Debbie Millman:
When you first started as a journalist, you immediately started covering the internet.
Kara Swisher:
No, I did not. No, I was an intern. I actually delivered mail. That was in college at the Washington Post. I worked my way up at the Washington Post from a news aide in the style section. I worked at the McLaughlin Group. You can read about it in my upcoming memoir. I worked at the City Paper here in Washington, it was great, when I was 22, 23. Worked in McLaughlin Group. Testified against him in a sexual harassment trial that he never paid for, but he’s dead. So, it’s all good.
Debbie Millman:
Actually, you did say you were glad he died.
Kara Swisher:
I was thrilled, thrilled. I think at one point I said to him, “You can’t die soon enough.” He liked it. He thought, “Hahaha.” “I really hope you trip.” I shouldn’t say… Yeah, I should say that. What the hell? Yeah, I worked my way up. I filled in for people who were on maternity leave. And I started covering a family that some people may recall, the Haft family. They owned Crown Books, Trak Auto. He had a big pompadour, a gray Pompadour. His son had a brown pompadour. They were billionaires. And I started writing about their fights. It was like King Lear here in Washington. Anyone who’s of a certain age-
Debbie Millman:
Well, you wrote it like it was King Lear.
Kara Swisher:
Yes, I did. I wrote it like Shakespeare, and it got me very well-known at the Post. So, that was retail. I was covering retail, and I got so sick of them because they were really loathsome. That story was loathsome, and especially Herbert Haft himself. He’s dead too, good. Works for me. But he was terrible to his family. He was terrible to his wife. And it was one of those stories of people with so much means that all they could do is… And it was really borne by him in many ways. It was a great business story and everything else, and a great personal story. And I wanted to get off of this beat more than anything.
And so, of all people, David Ignatius, who’s now a columnist, was my boss in the business section. And I said, “You have to get me off this beat.” And he said, “Well, there’s this company out in Virginia called AOL, and you’re a young person.” I was the young person. “You should do this internet thing.” It wasn’t even internet. It was digital services, online services. And so, that’s where I started covering it in the ’90s, in the early ’90s.
Debbie Millman:
But when you started doing that, you really felt that-
Kara Swisher:
Oh, immediately.
Debbie Millman:
Yeah. So, what gave you the sense? I mean, there were a lot of journalists at the time that thought the internet was a Ponzi scheme.
Kara Swisher:
They did.
Debbie Millman:
You understood the transition between the telegraph and radio and television. What gave you that certainty that it was going to end up being what it ended up being?
Kara Swisher:
I had studied propaganda at Columbia, and also, it was my piece. I wrote a paper on it. And also, at Georgetown, I was at Foreign Service School and I was really interested in communications means. The minute I saw it, I was like, “Oh, I see what this is. This is everything.” And it was very easy to see that it was like the telephone, television, but it was super-sized. And when you saw the Mosaic browser for the first time, and you could click on it and get any piece of information, and I say this in my memoir coming up, the thing that occurred to me at that moment was, everything that can be digitized will be digitized. That was it. That was it.
I was like, “Oh,” and I downloaded a book and there’s a famous story of me downloading a book and messing up the thing. But I was like, “Oh, wow, wow, wow.” And then I could see, because I wanted to be in military intelligence or CIA, I was going to do scenarios, and I was like, “Oh, this goes to this, and this goes to here, and this business will be over.” And so, I was at the Washington Post and someone I have great regard for, Don Graham, was the owner at the time, Catherine Graham also, but she was older and he was running it. And I was like, “You are so fucked.” I just saw it.
I was like, “There’s going to be… It’s not subscription because news will be free. This will be a problem. It’ll collapse that business, your classified business, which is shitty for customers and expensive is over because this guy named Craig” who I just had dinner with the other night actually, he goes, “I’m the guy with the list.” I’m like, “Stop it. Stop that. Stop that joke.” But he does that all the… He still does it to this day.
Roxane Gay:
I can’t believe he’s doing that joke this many years later.
Kara Swisher:
It’s okay. It’s his thing. He’s Craig with the list. But I did say, “Stop it.” He’s a lovely guy. He’s actually given away a lot of money to journalism and all kinds of good causes. And so, I saw that. And then I thought subscriptions, digital news, classifieds. And then at the time, the brand advertising was dying, display advertising at newspapers. I just saw it. I was like, “Oh, this is going to change everything.” And so, I moved to the Wall Street Journal pretty quickly because I thought it was on a higher floodplain, but it was still on a floodplain. And so, I just kept seeing it and saying it to people.
Debbie Millman:
Now, you-
Kara Swisher:
And I carried around a suitcase phone that the Washington Post had, and I was like, “You’re not going to have a phone at your desk.” I was like John the Baptist of technology. I was like, “Why are you sitting there when you can go anywhere?” And they were like, “Get away, lady with the suitcase phone.” And then I had the big Gordon Gekko on. I’m like, “No, it’s littler.” And they’re like, “That is a big fucking thing.” I’m like, “It’s going to be even littler. It’s going to be like Star Trek.” And I stood in line to see the StarTAC like an idiot. That was the flip phone, the first really impressive phone. And I just was in love with it immediately. And you could just see it. You could just-
Debbie Millman:
Do you still have the same phone number you had back in the ’90s?
Kara Swisher:
I have my phone number for a long time. No. When I moved to San Francisco, I have the same one, 97′. I’ve had the same phone number since ’97.
Roxane Gay:
Wow.
Debbie Millman:
’93.
Kara Swisher:
’97, yeah.
Debbie Millman:
Of course, you know me.
Roxane Gay:
Yeah, that’s true. That’s true. You enjoy holding on to these important things. Now, you’ve been doing this for almost, not almost, more than 30 years, and you’ve written for any number of publications. You’ve been talking to for and about these tech leaders. And many people in many publications refer to you as the most feared and the most liked journalist in tech.
Kara Swisher:
I’m not sure about the liked part, but okay.
Roxane Gay:
How do you walk that line?
Kara Swisher:
I don’t think I’m feared. I think I’m very-
Debbie Millman:
Oh, you are.
Kara Swisher:
Okay.
Roxane Gay:
Yeah, you are.
Kara Swisher:
Whatever.
Debbie Millman:
You are.
Kara Swisher:
I’m not scary. It’s like give me a break, boy.
Debbie Millman:
Well, you’re being wonderful and you are wonderful.
Kara Swisher:
I think what I do is-
Debbie Millman:
But I do think-
Kara Swisher:
I think I approach it like, “Yeah, no, I don’t get that.” You know what I mean? I think a lot of people, you either, in tech, either have people who are fan boys and there’s tons of them, and they’re all boys, let me just say. It’s all boys, who just love it. Like, “Oh, my God, Bill Gates, your giant brain is so astonishing.” And he’s smart. Okay, but come on, there’s a lot of advantages he had. And so, I approached it like, “Yeah, I don’t get that. Explain it to me like I’m an idiot kind of thing.” And I also questioned them when they act like magicians and everyone reveres them. So, you have that group, which is they can do no wrong, which I think went on for far too long.
And then there’s the people that are too snarky towards it because I really think it’s amazing. Technology has been astonishing over the past couple of decades and just amazing. It’s just amazing. And I use an example in my upcoming book where I said you don’t want to be the person at Kitty Hawk. They take off. They fly whatever amount of feet they fly. It’s correct in the book, but they fly a certain amount and they land and you go, “Well, they were supposed to do 15 feet and they did 13.” That’s not the person… They flew.
Debbie Millman:
Roxanne’s mother would’ve done that.
Roxane Gay:
They said accurate.
Kara Swisher:
They said 20 and they did 13. It’s a failure. They flew. I do have that great regard for tech in that, the things it could do. And so, I have a great hopefulness about tech as a tool and in good ways. And I am very aware of it as a weapon too. And so, I think I did that and I kept pointing out the weapon part. And especially when it got more weapony, I was like, “Just a second, misinformation and things like that.” And I would say it to them because I did have a lot of access, but I didn’t do access journalism. Sometimes I did, but I tried not to. I tried to always say what the problem was very clearly.
I think the confident people like Steve Jobs, actually, he talked to me 8, 10, 12 times on stage. Never did that with anyone else, along with Walt Mossberg. I think the smart people were able to, or adults I say, were able to handle criticism. Not always. He could be super thin-skinned. And the children, the toddlers, were not. They threw fits when you didn’t lick them up and down all day.
Roxane Gay:
Do you think-
Kara Swisher:
They like that.
Roxane Gay:
I’m sure they do.
Kara Swisher:
Not that there’s anything wrong with that. I’m from San Francisco. It’s fine.
Roxane Gay:
Do you think that the kinds of people who are succeeding in tech are changing from that man-child or woman-child to a lesser extent-
Kara Swisher:
Almost zero extent.
Roxane Gay:
… into smarter people, people who are perhaps genuinely more socially aware and understanding of the dangers of the weapon?
Kara Swisher:
No, I think we’re in a very bad period. I mean, look who’s the hero right now, and Bill and Elon Musk. So, someone I’ve interviewed more than anyone on the planet, actually. Someone I liked quite a bit actually, and thought, “God, at least he’s doing interesting…” Most people are doing digital laundry services. They’re like, “I’m doing a digital laundry.” I’m like, “Oh, my God, really?” I couldn’t think of anything less creative. And he was doing some really… The electric vehicle stuff, the space stuff is really interesting and really important, I do think. Even some of his wackier schemes, the Hyperloop and The Boring and the Neuralink, interesting, really interesting. And then there’s this part of him that has now taken over his brain almost completely.
Debbie Millman:
Well, what happened? Why do you think it turned in this way?
Kara Swisher:
I’m not a psychiatrist. I think he’s just turned. I don’t know, turned bad, rancid. He had that part of his personality, juvenile memes and silliness. I think he had a tough life growing up. That said, lots of people did. It’s not an excuse.
Roxane Gay:
I was going to say.
Kara Swisher:
I think I just had a wrangle with Walter Isaacson about that. He likes to use Shakespearean, “Well, he’s a complex person.” I’m like, “Maybe he’s just an asshole.” Like now, he’s an… And well, he had a difficult childhood. I’m like, “Really? This is what we’re going to… Oh, he has demons.
Roxane Gay:
So, did Oprah.
Kara Swisher:
Yeah, exactly, Oprah. Hello, Oprah’s lovely, as far as I can tell. I think they’ve gotten worse because the money is so vast. And the people, their enablers, are so obsequious and nobody tells them they’re wrong. I was talking to Elon about Twitter. I thought maybe he could help it because it had all kinds of business issues. It had all kinds of management issues. And I had hopes that, okay, here’s an interesting person who could maybe do something. And then the first thing he… And he actually and I texted about it. And then he tweets the Paul Pelosi thing and a bunch of things. What had been a small part of his personality, I would say, which was a little dark, really got all of it. It just invaded his entire brain, it seems like. Maybe he’s being performative. I don’t know. It seems like the act is going on for far too long.
But my issue with people like that is the power they have. I’m not going to get tweaked because he decides Russell Brand needs defense, but okay, sure, whatever. Of course, he did. Of course, he went to Russell Brand’s defense. It’s because of the power. And you saw that in the Starlink thing. That he didn’t… Walter got it run. In fact, the story, I actually called Walter I said, “A Ukrainian defense official just came up to me at an embassy party and asked me to help geofence Crimea.” And I was like, “I felt like I was inappropriate for the person to be asking to do this.” And at the same time, I wasn’t talking to Elon at that time because we had a falling out over a number of things he was tweeting, but the falling out we had was over the Starlink thing because I thought it was dangerous.
Roxane Gay:
It is dangerous.
Kara Swisher:
He’s unaccounted and he can decide what to do. I do blame our government and the Ukrainian government for not having options. But he was there with what they needed at the moment, which was very generous actually. But now, he just gets to decide. And then he started parroting what I felt were Putin talking points, which was… I mean, you can have your opinions about too much war, absolutely. But this is not a person you want to put in charge of anything like that.
Roxane Gay:
I agree. Now, is there a way to keep these kinds of billionaires in check?
Kara Swisher:
No.
Roxane Gay:
I mean, you mentioned the government is at fault, which for many things, but it seems like the more wealth these men mostly accumulate, the less-
Debbie Millman:
Yeah. Are there any women in that group?
Kara Swisher:
MacKenzie Bezos has some money because-
Roxane Gay:
Yes, but she seems to be willing to do a little bit of, a lot differently with it.
Kara Swisher:
She’s done a lot of philanthropy. She has indeed.
Roxane Gay:
And so, what are the consequences of unchecked? It’s not the innovation that I’m worried about, but the unchecked access, the unchecked power, making these rash decisions.
Kara Swisher:
What’s the people are unaccountable, it’s the robber barons all over again. You know what I mean? I think it’s these people who have unchecked power, unchecked wealth that’s beyond belief. It’s crazy amounts of money, influence over government, influence over governments. You saw Benjamin Netanyahu just paid fealty to Elon to try to help him out of the anti-Semitism issue. Maybe don’t say anti-Semitic things, that might work. The prime minister of Israel is helping him out of a jam. Are you kidding me? Are you kidding me? So, he will go over there and invest, put a Tesla plant there or whatever they want.
And so, I think that’s what scares me is even… And I thought they should have taken Trump off long before. I had written columns saying that I was at a party and I put this to the people there, and I said, “What if after, if he loses the election and he says the election was fraudulent. He keeps doing it for weeks on end, and then he urges his followers to attack the Capitol?” I said that in a column in 2019. It was just a scenario that I built. What would you do? And I felt like he’d broken rule after rule on these platforms and should be taken off temporarily or whatever. Just everyone else gets kicked off. Shouldn’t he be?
I didn’t love that one or two people made that decision. You know what I mean? That made me super uncomfortable that… It was at the time, Jack Dorsey, although he tries to pretend it wasn’t his decision. Or Mark Zuckerberg, that also makes me deeply uncomfortable, although I don’t think these are public platforms. They’re just private squares. They’re not public squares, but they certainly aren’t important.
Debbie Millman:
Where do you see the future of social media going?
Kara Swisher:
I think it’s starting to crack. I don’t think people are as quite as engaged and interested. I don’t think it’ll have the same power. AI is really where the action is right now, where a lot of the… And that will have implications not just on social media, but healthcare, on finance, on publishing for sure, on entertainment. So, it will have widespread. It’s the internet on steroids. I don’t know how else to explain it. It’s really-
Debbie Millman:
Is that a good thing or a bad thing?
Kara Swisher:
It could be a good thing. It could be healthcare you could have drug discovery. You could have drug interactions, drug discovery, gene, genome stuff, all kinds of things. Education, you could really bring education all over the place. Healthcare, in particular, is a particularly promising area. Figuring out climate change stuff, patterns. There’s all kinds of things it could do. It’s also a copyright thief as usual, which these people are. It’s controlled by the same companies. It’s Microsoft, Meta, Apple, Amazon, Elon Musk. It’s the same people. It’s the same, same powerful people getting ahold of tools that our government… You can say all you want about the government, but it’s called elected officials. They may be incompetent, but they’re elected.
Roxane Gay:
Yes. So, incompetent people put them in office.
Kara Swisher:
No, but they’re elected. At least there’s some governor on it. And in this case, there isn’t. It’s just that these companies are making decisions that will have grave implications on the rest of… I’m not someone that’s like, “Oh, it’s Terminator time.” I don’t think that’s really what the issue is, as some of them are saying. But I do think it’s enormous power in the hands of a very small group of people. I’m not scared of AI and generative AI. I’m scared of people using generative AI, which it’s always the humans that fuck things up.
Roxane Gay:
I’m curious about that because oddly enough today, and I haven’t even told you this yet, but today, I got an email from a man who said that he had made an AI chatbot by teaching it all my books and interviews and essays and et cetera.
Kara Swisher:
Scott’s doing that now.
Roxane Gay:
And he was like, “I think you should use it and it will amuse your followers.” And I was like, “No, you need to delete those right now because I exist and I don’t need a bot to do me.”
Kara Swisher:
But you do, actually. It could be interesting for you.
Roxane Gay:
I recognize that this is the way of the future. How do we learn more?
Debbie Millman:
I want to know what Kara thinks about that.
Roxane Gay:
What do you-
Kara Swisher:
I think you should actually.
Roxane Gay:
Really?
Kara Swisher:
You should do it yourself. Well, interesting, I just did an interview with Martha Stewart, who’s always up on things. She really is quite an astonishing lady. She’s a real entrepreneur. People don’t give her credit in that regard, but she’s doing Martha AI. Get it? I thought that was funny.
Debbie Millman:
Well, you could do the same thing, Kara AI.
Kara Swisher:
Yeah, right, right. She almost bought Kmart. It was to be MarthArt or something like that, as a matter of fact. I think she’s not going to remember all the things she’s done, and she owns a lot of her IP. So do you.
Roxane Gay:
Yes, I do.
Kara Swisher:
I do now. And so, she’s taking all this IP. She doesn’t remember every time she figured out how to get a stain out of a cloth. She doesn’t remember every one of them. And she’s put out so much content about where to put the plate and this and that. This is in her area of gardening and home. And if you brought it all in one place, it could answer for her. She’s not going to be able to do it. Yours is the same way, but it’s based on your thing. So, it could be very interesting for a lot of people who have a lot of content, absolutely, I think.
Roxane Gay:
That’s interesting because after I sent off the email, that was my gut reaction. Then he was like, “Can we talk a little bit more about this?
Kara Swisher:
You need to talk. Yeah, but it should be yours.
Roxane Gay:
And I didn’t respond.
Kara Swisher:
Be careful. Why did he put your things in without your permission?
Roxane Gay:
Exactly,
Kara Swisher:
Yean, that’s a problem.
Roxane Gay:
Didn’t even consult me. And then thought he was doing me a favor.
Kara Swisher:
That’s a problem.
Roxane Gay:
You’re a white man. I would never choose you to lead me into the Promised Land.
Kara Swisher:
One time years ago, I was walking with Larry Page around Google and we ran past a room that was full of televisions and they were going. And I was like, “What is this crazy fucker doing?” And I said, “What are you doing, crazy fucker?” And he said, “We’re taping all of television.” And I was like, “What do you mean?” He was using closed captioning to search it, to search video. And it was brilliant, but I was like, “Do you own the copyright?” And he’s like, “Why do I need that?” And I was like, “Because it’s copyright.” And same thing they did with books.
Roxane Gay:
Yes, they learned the hard way.
Kara Swisher:
They were just copying them without any kind of rights to them. And they were met with a real problem when they went to visit. I happened to be with them when they were visiting the book publishers and they’re like, “We’re going and asking them for all to be able to search it, to put everything in our thing. I’m like, “They’re going to say no.” And they’re like, “Why wouldn’t they? It’s so great.” I was like, “Because when you do it, you control it and they are fucked.” They just were like, “We’re trying to help people get all the information.” I said, “But it’s their information.”
You would have discussions like that constantly. And they were like, “Well, yes, but all information needs to be free.” I said, “Oh, that’s a really nice shirt you have. I think I’ll just take it. I like your money, your billion dollars in the bank. I think I’ll just take it because money needs to be free to Kara Swisher.” They literally don’t think like that. Everything is fair game for them. All the information is, for sure. But you should do it anyway.
Roxane Gay:
You have given me food for thought.
Kara Swisher:
I’ll put you in touch with a few.
Roxane Gay:
Okay, that would be great because I know nothing about it and I just need to learn.
Kara Swisher:
Everyone’s going to have one of these. It’s going to be a plug and play for everybody in that regard, but you have to have providence in who owns it and this and that. There’s going to be a lot of lawsuits. Barry Diller and I just did an interesting interview where he’s going to sue everyone. He owns a lot. I love Barry Diller. He’s like, “Fuck you everybody.”
Debbie Millman:
It’s only going to be possible for people to sue if they have the money to be able to sue. For the people that don’t have money-
Kara Swisher:
Yeah, that’s the help for… No, our copyright laws are really quite good in this country. They need to be updated, but that’s what happened to YouTube. And then they had to pay everybody after they stole everything, so that it can be done. Copyright is very, very good law in this country, but still, they’ll try to take it because that’s what they do.
Debbie Millman:
This is a question that Roxane was going to ask you, but it was a little bit further down in the interview. I think it’s appropriate time to ask it. So, if you don’t mind, Roxanne, I’m going to just go for it. In many interviews, you speak openly about money, which is rare, particularly for women. And you’ve said you know your worth.
Kara Swisher:
I do.
Debbie Millman:
How do you determine what you’re worth?
Kara Swisher:
By knowing what you’re worth is like knowing where your leverage is. I think about leverage a lot. One of the things that I always noticed was, especially women as a boss, I noticed this and as a person of myself trying to get money, women almost continually undervalue themselves and men way overvalue themselves. There was one point where I was firing two different people and one of them… We were going to give a severance and it was a number. It’s the same severance kind of thing, and it was generous. And the guy asked for double the severance and I was like, “I don’t even want to give you this. No.” And the woman just took it and could have asked for more. You know what I mean? I was thinking, “Huh, that’s interesting. This son of a bitch is…” Anyway-
Debbie Millman:
Now, do you think it’s because historically we’ve just made less than men? Or is it because we just value ourselves less?
Kara Swisher:
I don’t know. Again, I don’t know. I’ve always thought, “Give me that. I did that. I made that. Give me the money kind of thing.” And I was in a discussion with someone I was working for and they were like… I was making a certain amount of money at the, I’ll say this, Jim Bankoff, who’s great, who I love, by the way, He’s really great and entrepreneurial, really great, but at the time, he wanted me to take less money and then… I made a lot of money at The Journal because I had a piece of the profits. I always took a piece of the… If I made it, I wanted a piece of the winnings, essentially. And we got it. We get that. And if you ask for it, you often can get it.
And so, he wanted me to take less. And at one point, and he’s never done this again, he goes, “Just take more stock and less cash and less guaranteed cash and then we’ll go out, we’ll be pals.” I said, “I don’t need any fucking pals. I like you, but at this time, you’re not my friend. So, no, I would like the money and then I will pay for drinks.” And it was preying on a thing for women who want to get along. Just be nice, be a nice girl, and then everything will be good. And I’m like, “I’m not that nice girl, so I think I’ll just take the money and then you’ll like me better. I know it.”
And so, it’s not money for money’s sake. I’m like, if I make something, if I make a conference that makes, say, $4 million in profit, I thought it up out of my head. They’re not helping me that much. Why should they get all of it? Why shouldn’t I get half of it if they are my partner? It doesn’t occur to me not to take the money. And I always take the money and ask for it, and I think people should. I don’t know why… I think women don’t, that’s for sure.
Debbie Millman:
Quite a long time ago, I interviewed a designer and we were talking about money and he said no matter what he’s offered, he always asks for more. And he always goes back and says no matter what, even if it’s a great offer, is there any more he can get? And he always gets more. Always gets more, and I’ve told that to designers ever since. This is something he does.
Kara Swisher:
I’m doing that right now. I just got more.
Debbie Millman:
Just can you get me a little more?
Kara Swisher:
Sometimes though I don’t. If I feel like it’s fair, I don’t like to be, “Now, give me triple.” I don’t think you have to be a jerk about it.
Debbie Millman:
Well, he always says just a little. Yeah.
Kara Swisher:
Yeah. I just know what I can make. If I make this much money, I will take this much and I think most… Then you have an incentive. Then everyone’s incentives are aligned. I like when incentives are aligned. I don’t like… I had someone at one point. I was making tons of money for this particular entity and you could see it there. It was coming in. I can see it. And at one point, they’re like, “Well, you’re the most highly paid person here.” I’m like, “I don’t give a fuck. I make the most money here. Give me the money.”
And I sometimes been in meetings where they’re trying to make me take less and I just keep going, “Give me the money. Give me the money. I’m not leaving till you give me the money. Or else, I’ll leave and then I’ll get more money somewhere else.” I have the ability to do that now because I’m lucky, because I have a good career. But I just, I don’t know. People do. I don’t know. I just want the money. Money’s power. That’s why. Because money is power. That is-
Roxane Gay:
Before you got lucky though, I mean because everyone starts somewhere. Were you still able to do this, to just say, “I want what I want”?
Kara Swisher:
Yes, I did that. I did that back then, yeah, when I was offered less, although I did make, I just remembered $14,000 at City Paper. That was a shitty salary, but it was okay for the time.
Debbie Millman:
What year was it? I made $16,000.
Kara Swisher:
19…
Debbie Millman:
… at Cableview in 1983.
Kara Swisher:
Probably in that. No, a little later. Maybe ’86, something like that. Yeah. Yeah, yeah. It wasn’t unfair for the moment. But what I do think is important is if you’re an entrepreneur just like… And this is what I’ve learned from the tech people is, if I make something, I want a piece of it. And I think too many people work for salaries. I think that’s what it is. All people should be participating in the upside. That’s what’s happening in the UAW strike right now. They want to participate in the upside. Same thing in Hollywood.
And if you make things, you should benefit from what you make, and you shouldn’t just sit there. Especially if you’re creative and entrepreneurial, you deserve that extra. If you create something out of nothing, you should benefit. And that’s one thing I do love about the tech people, they make things. They take the windfall of it and they take the risk. If things don’t work, I’m perfectly willing not to take any, to not win.
One time, I was with a very famous Hollywood producer who made hit shows and Instagram had just sold for an enormous amount of money. And Kevin Systrom, another lovely guy, got $300 million in Facebook stock. It’s a lot more now or something like that, some enormous amount of money. And he’d just started the company three days before. And so, it was great. Good job, Kevin. And so, this guy was like, “Why did he get so much? Why did he get so much?” And I go, “Well, he owned it. He owned it. That’s why. And then he sold it and that’s how he got so much. It’s not that hard, sir.”
And he’s like, “Well, I make a lot of money.” And I was like, “No, I don’t know how much you make.” He was making shows for one of the networks. And I said, “But I bet you don’t make as much as they do off the things they make of yours. You get the $100 million and they make 3 billion at the time.” Not anymore, these networks don’t. I said, “So, you are really just a cheap date.” I said this to him and he’s like, “I make a lot of money.” I said, “I bet they sent the plane for you for the Emmy’s. Was that nice? Why don’t you own your own plane?” That’s the kind of things they did.
Or you got the Oscar, congratulations on the Oscar flowers, or they did all this petting stuff for these people, and then took most of the value out of it. And I was like, “The reason this network is in the place it is because of you, because of your creativity. Even though your shows are shitty, but they’re still popular. So, I don’t know what to say.” And so, that’s what I was… I was always urging people to, if they’re the entrepreneur, they should take things. I think that’s fair.
Roxane Gay:
Speaking of creative output, Debbie, I think we should ask about the memoir.
Kara Swisher:
The memoir.
Debbie Millman:
I do, but I just want to ask one more question about money.
Kara Swisher:
Sure. Money, I like money.
Debbie Millman:
Have you ever made a bad money decision or money decisions that you’ve regretted?
Kara Swisher:
Probably not taking every job that I’ve been offered from internet. I would be very extraordinarily wealthy right now and then I’d use-
Debbie Millman:
You actually said disturbingly wealthy.
Kara Swisher:
I’d be disturbingly wealthy, but I did… My ex-wife is Megan Smith. She became the CTO of America, but I convinced… When I was covering, not covering Google, I knew the Google guys and they were very much interested in her working there. I said, “You should go there. You’re going to make a lot of money. You’re going to make… Go there. Go there.” And she did, and she did make an enormous amount of money. Not as much if she had gone when I told her to, but nonetheless, she made a lot of money. And then when we got divorced, I didn’t take anything like an idiot. I’m such a bad gold digger. Yes, I don’t regret that. No, she made it. It’s her money, but I got a nice house out of it. I did. It’s my house.
Debbie Millman:
Well, didn’t you get the house from the money that you got from your grandfather?
Kara Swisher:
Yes, I did.
Debbie Millman:
So, then how did you-
Kara Swisher:
Well, I know, but we paid for it together, whatever. You don’t want to go into the details of my divorce. Thank you. But she has a lovely house here in Washington, I’ll say that. I think about what would I have, if I had said yes to AOL those many years ago, if I had said yes to… I was offered a job at Amazon. I was offered a job at early Facebook, early all of them. And I just was like, I just didn’t want to work with them. I know it sounds dumb, but I was like, “Oh, do I have to look at you all day again?”
Debbie Millman:
Same thing.
Kara Swisher:
Same thing.
Debbie Millman:
Now, I could be wrong about this, but it means-
Kara Swisher:
Sometimes I wish I had all that money, so I could do political things.
Debbie Millman:
But that’s why I think you didn’t take those jobs because I do think… I mean, I don’t want to-
Kara Swisher:
I liked what I was doing. That’s all.
Debbie Millman:
Yeah, I mean, it just seems like there’s a lot more integrity-
Kara Swisher:
It wasn’t an anti thing.
Debbie Millman:
… in what you were doing.
Kara Swisher:
I liked what I was doing. I liked… And that’s the one thing I’d say is that whenever you do anything, you should like what you do. And when I don’t like something, I quit. I think a lot of people stay in the same place because they think they have to. And most of us, especially in this room, are very lucky. They have a lot of choices. I’m fully aware that I have choices all the time. There’s people around the world that have no choices whatsoever, all around the world. And it seems wrong if you have choices not to take them, especially when you’re educated, you live in America, all kinds of things that you have advantages of.
So, I just can’t. I just can’t. I just can’t do it. Just the same reason I had kids in my late 50s, was like, “Oh, I want some more kids. That’s what I want. That’s what I want.” And plus, they’ll be taking care of me when I’m super old. That’s a good thing. Totally a reason. I’m sorry, I’ll admit it. But I wanted to have kids. I love kids. Everyone was like, “Really?” And some mornings like this morning when they get up at four o’clock, I’m like, “What in the hell did I do that?” But otherwise, it’s really something I want to do, so I’ll do it.
Debbie Millman:
Am I right in thinking that during your interview with the astrologist Chani Nicholas you said you wanted seven children?
Kara Swisher:
I did. I did. I did. I did. I wouldn’t have-
Debbie Millman:
So, you have three more to go?
Kara Swisher:
Yeah, I’m like Elon Musk in that regard, right? I’m trying to populate the planet. No, I’m trying to populate the planet with the kind of kids… My sons are astonishing. I mean, I always joke about this, but lesbians should raise all the men. They’re confident and feminist. And at the same time, they’re tough and cool. You know what I mean? They’re just great kids. You can listen to my son, Louie, on my podcast this summer. I had him on. He’s a fantastic kid. All of them are.
Yeah, I did. I wanted kids since I was 17, 18 years old. I bought a onesie when the Akia opened here out at wherever the hell it is out in, you just drive in Virginia for a while and you run into it. Where is it? It’s in…
Roxane Gay:
It is-
Kara Swisher:
Potomac Mills. Potomac Mills.
Roxane Gay:
Ah, oh, my god. [inaudible 01:04:56] at Potomac Mills?
Kara Swisher:
I should know that because I cover the openings. Went Potomac Mills. I guess I covered that mall when I was with the Post. But yeah, I bought a little onesie that all my kids have worn when I was 18 years old, which is incredible.
Roxane Gay:
Wow.
Kara Swisher:
Yeah, I love kids. I think it’s great. I think they’re great. I know you’re not supposed to have more than… I’m making up for everybody else because nobody else is having kids. And I do think, I joke, I have a stupid gay joke, but I’m like, “I’m building the Militia Etheridge.”
I had an argument. It’s that idiot, J.D. Vance, who I’m so glad Mitt Romney also agrees with me about. He started strafing me on Twitter, which I was like, “Don’t you have a Senate campaign to run, you dumb ass?” And I knew him before he was this version of this, when he was just a tech person with Steve Case, and his book was interesting. His book was interesting. And he insulted me about how liberals don’t like the future. And so, I tweeted back, I go, “I have double the kids you have. And so, first, what’s the problem with your life and your wife? Two, I believe in the future twice as much as you do. So, get on it, J.D. Let’s start to have some kids, if you really believe in the future.” It’s so ridiculous.
Debbie Millman:
Let’s get busy, Roxanne.
Kara Swisher:
Are you having kids?
Roxane Gay:
I’ve been trying. And somehow, I haven’t impregnated you yet. Lord knows I put in the effort.
Kara Swisher:
You don’t need that anymore.
Roxane Gay:
No, we don’t. I mean, I think we both-
Kara Swisher:
I actually still have sperm left. I got pregnant on the first pregnancy and my ex-wife got pregnant, so I have a lot of sperm left.
Roxane Gay:
Wow.
Kara Swisher:
It’s excellent sperm, apparently.
Debbie Millman:
This is going in places I never expected.
Roxane Gay:
Neither would have I. I mean-
Debbie Millman:
The first time ever we’ve discussed this-
Kara Swisher:
I bought it for cheap.
Debbie Millman:
… on a podcast that I have done.
Kara Swisher:
I bought it for cheap. And now, I could sell it for… It was very inexpensive way back when because no lesbians were having children.
Roxane Gay:
And now, all of them are.
Kara Swisher:
I could sell it at a great profit, for example.
Roxane Gay:
Yeah.
Kara Swisher:
I get it cheap.
Roxane Gay:
Especially because you have examples.
Kara Swisher:
I would give it to you.
Roxane Gay:
Like look what it makes.
Kara Swisher:
Yeah, look what it makes. They’re handsome and they’re fantastic. Lesbians. I sat in the sperm clinics. You can’t figure. I had a no donor. And I shouldn’t have done this, but I sat in the lobby there just looking at the men coming in, and they were all California Tens, every one of them. And I thought, “Of course, they’re vain and they think they should go on.” That’s what I thought, “Oh, yeah, this is what’s happening here.” And I thought, “Fine, I’ll take that.”
Roxane Gay:
Yeah, I mean, a California Ten is really high, so that’s-
Kara Swisher:
I have a son that is 6’4″, almost 6’5″. So, here I am at 5’2″. So, it’s fine.
Roxane Gay:
It works out.
Kara Swisher:
Works out.
Debbie Millman:
All right, let’s talk about your memoir before we-
Kara Swisher:
Again, you can have the sperm if you want it.
Roxane Gay:
Okay. I mean, we will have a little discussion. [inaudible 01:07:43].
Debbie Millman:
You all heard it here first.
Kara Swisher:
I have a lot.
Debbie Millman:
Anything can and will happen in live radio.
Kara Swisher:
I have a lot. It’s in a cryo whatever the fuck in California. I pay $300 a year and I can’t stop paying $300 a year for it.
Roxane Gay:
That’s interesting that you’re holding on to it.
Kara Swisher:
I don’t know. I shouldn’t.
Debbie Millman:
She wants seven children, Roxanne.
Roxane Gay:
That’s true. And so, TikTok.
Debbie Millman:
Did you just say TikTok?
Roxane Gay:
I did. I did. We have one last question.
Kara Swisher:
All right.
Roxane Gay:
With your memoir coming out, it’s called Burn Book: A Tech Love Story. So, I’m curious because you’ve also said that you hate the people that you write about.
Kara Swisher:
I don’t hate all of them.
Roxane Gay:
So, how do you balance hating them and then wanting to write a memoir?
Kara Swisher:
Hate’s a strong word. I’m tired of writing about a lot of them and I’m very disappointed. It’s a book about a love gone wrong, I guess. That’s what I would say, when you see someone that you loved turn in a way. I do have a whole chapter. There are people I like. And then I write a whole chapter about people I like a lot. And most of them act like adults and are really trying hard. I happen to like Sam Altman, who’s doing a lot of his AI. I think he’s a really thoughtful person. I’ve known him for a long, long time, and I think a lot of them. I like Reid Hoffman, another person very involved in AI. I very much like Tim Cook. I like Satya Nadella. There’s all kinds of people I like. I mean they’re not my friends, but you know what I mean.
Roxane Gay:
Yeah, definitely.
Kara Swisher:
I don’t have a problem with their personal lives. And we disagree, but it’s fine. They’re adults. But it’s a lot of what happened to these people. They started off with these great hopes and dreams of connecting the world with each other and instead… I can’t say what the first line of the book is. When you read it, you’ll understand. It’s a story of heartbreak, is what it is. But it’s funny. It’s really funny.
Roxane Gay:
Good. Well, I think we’ll all look forward to it in March 24.
Kara Swisher:
March, yeah.
Debbie Millman:
Well, once the book is out, I’d love to talk to you more about it and have another conversation.
Kara Swisher:
Yeah, it’s good. You’ll like it. It’s really…
Debbie Millman:
I can’t wait.
Kara Swisher:
It’s a little bit different than Walter Isaacson’s book.
Debbie Millman:
Oh, good.
Kara Swisher:
Walter.
Debbie Millman:
Kara Swisher, thank you so much for making so much work that matters. And thank you for joining us tonight on Design Matters. And remember, we can talk about making a difference, we could make a difference, or we can do both. I’m Debbie Millman and I look forward to talking with you again soon.