Kara Swisher

Summary

Reclaiming with Monica Lewinsky: Episode Featuring Kara Swisher

Release Date: March 4, 2025
Host: Monica Lewinsky
Guest: Kara Swisher, Esteemed Tech Journalist and Author

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Introduction and Background

In this compelling episode of Reclaiming with Monica Lewinsky, host Monica Lewinsky engages in an in-depth conversation with Kara Swisher, a renowned tech journalist, author, and host of prominent podcasts such as Pivot with Scott Galloway and On with Kara Swisher. Monica introduces Kara as "smart as fuck, direct and kind," highlighting the unexpected vulnerability Kara showed during their discussion, which deepened Monica's admiration for her.

Building Friendship and Professional Connections

Monica recounts how she and Kara first connected on Twitter and through their mutual friend, Brooke Hammerling. Despite initial virtual interactions, COVID-19 delayed their first in-person meeting, which occurred during an interview for Sway. Kara describes this interview as her favorite, noting, "I always say that interview was really one of my best interviews" (02:24).

Early Career and Challenges

Kara delves into her early career aspirations, mentioning her initial desire to join the military, which was thwarted by the "Don't Ask, Don't Tell" policy of the time. She reflects, "I wanted to be in the military, actually, but I was gay at the time... It was ridiculous" (04:21). This led her to pursue journalism instead, where she became one of the first to cover major tech figures like Elon Musk, Mark Zuckerberg, and Bill Gates.

Experiences with Public Shaming and Workplace Harassment

The conversation shifts to Kara's tenure at The McLaughlin Group, where she recounts working under a controlling and sexually harassing supervisor. Kara shares a notable incident where her boss demanded she make him toast, stating, "If I ask you to make me toast and you don't do it, I'm gonna fire you" (08:56). Despite the toxic environment, Kara illustrates her resilience and ability to stand up against abuse, emphasizing her lifelong knack for asserting herself: "I have it my whole life... I walked out of fourth grade because I already learned that. And I was like, bored. I need to leave" (09:42).

Personal Loss and Resilience

A poignant part of the episode explores Monica's early childhood trauma—the sudden loss of her father at age five due to an aneurysm. Monica reflects on fragmented memories, sharing a heartfelt quote: "I can easily recall sitting on the bathroom floor under the sink as my father shaved in the mornings... but not the last night he said goodbye to me" (16:08). This loss profoundly shaped Monica's resilience, allowing her to navigate personal and professional challenges with a unique strength.

Kara connects this to her own experiences, noting how early trauma fosters a heightened sense of resilience: "You learn that you'll be fine, or not fine. But you'll survive" (22:47). Both women discuss the lasting impact of their childhoods on their adult lives, emphasizing the importance of supportive relationships in overcoming adversity.

Parenting and Personal Growth

The discussion transitions to parenting, with Kara expressing her deep love for her children and how motherhood has influenced her perspective: "I love my Kids. It's the best thing I've ever done. It's the only thing I think worthwhile" (37:02). Monica shares her desire to reclaim lost time with her own children, highlighting the emotional complexities of balancing parenting with personal identity.

Technology, AI, and Societal Impacts

Kara and Monica delve into the realm of technology and artificial intelligence (AI), discussing the ethical implications and societal changes driven by tech advancements. Kara criticizes the misogynistic culture in Silicon Valley, questioning why men dominate AI development: "Why is AI so popular with men? I believe it's because men can't create life, so they're trying to create bots as a surrogate" (47:58). Monica echoes concerns about tech leaders like Elon Musk, highlighting his domineering demeanor and unpredictable behavior: "He used to be that way, but... He didn't ask me any questions" (35:54).

Kara further explores the addictive nature of frictionless environments in technology, arguing that friction is essential for personal growth and integrity: "Frictionless environments are addictive. You need friction in life to be a good person, to be an alive person" (33:34). This philosophical take underscores the broader implications of technological advancements on human behavior and societal norms.

Reflections on Memory and Identity

The conversation touches on the fragility and reconstruction of memories, particularly in the digital age. Monica shares her struggle with memory gaps related to her father's passing: "I have never recovered from it. I think of my dad every day. I understand the giant hole left" (43:09). Kara relates this to the pervasive nature of digital memories and the challenges of maintaining authentic personal narratives amidst constant documentation.

Philosophical Musings on Life and Death

Both Monica and Kara engage in profound discussions about mortality and the human condition. Kara mentions using the app Wecroak to remind herself of life's impermanence, fostering a sense of urgency and presence: "If you think about death five times a day, you're happier... you're gonna make better choices" (31:38). Monica concurs, reflecting on how awareness of mortality shapes decision-making and personal values: "Everything's on its way to something else is a really comforting feeling" (42:02).

Conclusion and Final Thoughts

As the episode concludes, Kara and Monica share light-hearted moments, including discussions about tattoos and humorous anecdotes from their personal lives. Kara emphasizes the importance of maintaining one's integrity and avoiding toxic interactions, summarizing her approach to relationships and professional engagements: "I have this thing where I decide whether their prickishness is too big to account for their productivity" (44:48).

Monica thanks Kara for her candid insights, highlighting the richness of their conversation and the mutual respect between them. The episode wraps up with acknowledgments of the production team, leaving listeners with a nuanced understanding of both women's journeys toward reclaiming their identities and lives.

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Notable Quotes:

• Kara Swisher on Resilience: "I have it my whole life... I walked out of fourth grade because I already learned that. And I was like, bored. I need to leave" (09:42)

• Monica Lewinsky on Memory Loss: "I have never recovered from it. I think of my dad every day. I understand the giant hole left" (43:09)

• Kara Swisher on AI and Gender: "Why is AI so popular with men? I believe it's because men can't create life, so they're trying to create bots as a surrogate" (47:58)

• Monica Lewinsky on Creation and Destruction: "Everything's on its way to something else is a really comforting feeling" (42:02)

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This episode of Reclaiming with Monica Lewinsky offers a profound exploration of personal trauma, resilience, and the intricate relationship between technology and society. Through Monica and Kara's candid dialogue, listeners gain valuable insights into overcoming adversity, the ethical dimensions of AI, and the enduring quest to reclaim one's identity in a rapidly changing world.

Transcript

[Monica Lewinsky]

Wondery subscribers can listen to Reclaiming with Monica Lewinsky early and ad free right now. Join Wondery in the Wondery app or on Apple Podcasts, or you can listen for free wherever you get your podcasts.

[Kara Swisher]

Hi.

[Monica Lewinsky]

Hi, Monica Here for today's episode, I spoke with my badass friend Kara Swisher. You probably know her as a tech journalist and author and host of both the Pivot with Scott Galloway and On with Kara Swisher. So I've always known Kara to be smart as fuck, direct and kind, but I didn't expect her to reveal kind of such a soft side that she did in our conversation. And truthfully, it made me love her even more so. Anyway, I hope you find something to connect with in our chat and thanks for joining us on Reclaiming. So let's get into it foreign. Thank you to our presenting sponsor, Audible. Visit audible.comreclaiming to find your next listen. Thank you to our sponsor, Reformation. Visit reformation.com to see why they're my go to for stylish and sustainable fashion.

[Kara Swisher]

Kara Swisher, welcome to Reclaim Q.

Thank you.

For anyone who doesn't know you, can you give them context?

Who doesn't know me? No, I'm kidding. Exactly. No. I've covered tech for the past 30 years. I was one of the earliest people who covered the Internet. Not the Earl. I know about the earlier part, but I've covered the Internet, all the big people from Musk to Zuckerberg to Jobs to Gates, stuff like that.

I want to start out talking about just sort of setting the stage for how we became friends. So I think we first connected on Twitter and. And then through our mutual friend Brooke Hammerling a bit more. Then you kindly were interviewed for a documentary on public shaming and Cancel Culture that I.

Yes, for that great documentary you did.

Thank you. That I exec produced. And we still didn't meet in person. Cause of COVID then. And then the first time we actually met in person was when you interviewed me for Sway.

My favorite interview.

Aw.

I have to say, when people ask me, people are like, what's your favorite interview? They expect me to say Steve Jobs, which I also liked. Or Bill Gates or Mark Zuckerberg or Elon Musk. And I always say that interview was really one of my best interviews.

Oh, thanks, Kara. That was. It was special. It was special. I mean, it's funny because I was thinking about how we did it in that music studio with the Wii, the Broken.

Yeah, we did it in Los Angeles when I was there for my conference. And you Were very nice. Cause the studio was really janky.

It was so janky.

Yeah.

That's exactly the word that I was using.

The microphone. Smelled a Snoop Dogg podcast.

Cause we did it in the morning and I'm sure they were recording all night. But I realized, too, I was thinking about. That it actually might have been a good thing. Because you were high. Yeah. And it calmed me down. And I was so nervous. I was really nervous. I was terrified to be interviewed by you. Yeah. Even though I knew you were kind, but because you're so exacting and intuitive. And I felt like if anybody was gonna smell my imposter syndrome, it was gonna be.

Imposter is the thing.

I know.

Harder. It would be harder.

I know. But it's that I think I'm an authentic person. But trying to find myself out there as an adult in different ways has been hard.

But look at your record. I mean, it's very easy. Why would I be hard on someone who has handled themselves with such grace?

Yeah. So, well, thank you.

Well, it's true. You made one mistake, big mistake. But you've acted better than pretty much everybody in this entire time. Never dropped a dime on people. Never took advantage of it. Did helpful things after. Like, you moved to doing the bullying thing. You moved to doing things that were honorable and helpful rather than, you know, you could have gone a lot of different directions. I always think of directions people could have gone in when I do interviews. Like choices they could have made and they didn't. Which is, you know.

And you were like. The directions you were initially thinking about. Was it foreign service?

Yeah. Yeah.

But then you went into journalism. Yes. Right.

Not by choice. I mean, I wanted to be in the military, actually, but I was gay at the time. Speaking Bill Clinton. Don't ask, don't tell. Terrible. I couldn't be in the military, and so it was a disappointment to me. I wanted to do that. And so it was impossible at the time. It was very different than it is now. And it may go back to that, by the way, but there certainly was a. If you were gay, even if you were out, it was a problem, and you couldn't be out. I mean, it was ridiculous. The whole thing set up for ridiculousness.

No, I remember. I remember. And the height of aids and.

Yes. Right. Not just that. It was these. There was all kinds of ideas that gay people couldn't keep a secret. It was stupid. It was so stupid. Just the same thing. They couldn't be married. They couldn't have kids. All that stuff. Which is, again, Gone now, but you know.

Yeah, for now we'll see.

As you said, certainly can go back easily.

Terrifying.

They want it to go back. It's part of the many issues of rage these particular certain Republicans have over what's happened. And that's right up there.

Yeah. Well one of the things that I admire so much about you is that you've just. You have sort of a confidence and self possession in a way. And I think the best example of that is what I think of as the toe story. Will you tell it?

Sure. So one of the things I did when I was younger is I really, really wanted to work at the Washington Post, where I ended up working. But I went to Columbia Journalism school and again because I was gay, I didn't want to move to the south. That's where a lot of the jobs at newspapers were at the time. And I thought I'm not going to live a furtive life. I just hated that idea. Cause it's so debilitating to lie, right? Everybody knows that it's the most debilitating thing. And lie to yourself most of all. And so I was like, oh, I guess I'll start at the top at the Washington Post. But I couldn't get a job. And so the job I got at the time during the Reagan administration was John McLaughlin. Now I am very liberal, although different. I have different opinions about it because I want to be in the military, I want to be, I want to.

Serve same patriotic, very liberal.

Certain ways it's so ridiculous to put.

People libertarian and others and yeah, so.

Dumb to put people in boxes the way we have done now unfortunately to all of our detriments. And so I wanted to get into the media and so I was offered this job at the McLaughlin Group. And he was this very. He started screaming cable television. Who was the God, the H. And oh yeah, I remember and he had a show where it was like issue one and then they argued and it was so reductive and stupid. But actually compared to now it was smart, right? Cause he was a smart guy. And so they made public affairs shows like a wrestling match. That was his great insight. And it was a very popular show. And so he needed someone to write his column. He had a column that he wrote for I forget one of the magazines and I ghost wrote it for him essentially. And then he would sign off on it and add different flourishes. And so I worked also on the show on the insults like. Cause you know, on a scale of 1 to 10, 10 being nuclear Armageddon or I Was good with words, and I was good with insults. And so I wrote those. And during the time there, it turned out he was a really significant sexual harasser of the old school. Yeah, the chase around the desk type, kind of the obvious one. Not the Pete Hegseth type, who was more rapey and creeper kind of thing. This guy was a creeper, too, but much more of the old school, like, hey, honey, give me a kiss. That kind of thing. And very aggressive in that room, big guy. And he was that. And he was bothering a woman in the office, which I witnessed and testified against him later. But while I was there, he was also into controlling. Whether it was where you were in the office. He'd follow you to the bathroom to confront you, of course. Cause he was like. He was crazy. He was like. Control was. It's all about control, as you know. And so he would line people up by height and say, dust ball. And someone had to get it under the. These were all Republicans. I was not. So I never did it. I was always at the end, though, because of the height thing and not the tall end, the short end. And so he was just really abusive. And one of the things he did is he made everyone in the office, regardless of who they were, including his chief of staff, a really heinous woman. I will say make toast form. He liked white buttered toast. Now, I like white butter toast.

I was just gonna say, I like sourdough.

Who doesn't like white butter toast?

Well, toasted, extra bite.

Fine, I get it. But. And I get it. If he had a secretary, I guess, fine, I don't have people make toast. But he tried to get me to make him toast, and it was a thing. And I said, I'm not making you toast. And he goes, everyone in this office makes me toast. And I said, well, not me. I have a graduate degree in journalism. And so I'm not gonna do it. And he said, if I ask you to make me toast and you don't do it, I'm gonna fire you. And I said, great. Sounds good. And then he goes, okay. Just so you know, I go, got it. He never asked me to make him toast. It was really interesting. It was just. He wanted to know that he could. And I was like, I'm fine with that. Yeah, seems like fair.

Was that a moment for you where you sort of first saw your ability?

No, I had it before. I did it my whole life. I don't know where it comes from. I mean, I walked out of fourth grade. Wow.

Why?

Because I Had read it. I was in the principal's office. My mother came in. They're like. She's like, why did you leave? I said, because I already learned that. And I was like, bored. I need to leave. And I think I did that from the get go. My name when I was a baby was Tempesta, which is what they tell women who are firm. Right. They call you bossy or, you know, all those names for women who know what they want. It's fine. I mean, it's fine. I didn't mind. I liked being the way I was, so it was fine. Probably part of being gay. So I didn't really care what especially men thought of me. I like men compared to most women, I don't have to sleep with them. Sorry, Monica.

I know.

Yeah, that's your weakness.

Yes, exactly. Exactly. Well, you definitely. You have lots of superpowers. And I think one of the other things that's so interesting about you is that you're sort of this modern day Cassandra, you know, for what's happening in technology. Like you.

I'm so sorry to be. Right. That I.

Exactly, exactly. But I think it was like.

In.

The 90s, you predicted sort of the digitization of media.

Right.

You had a saying of something that.

Can be digitized, will be digitized by Google.

Yeah, exactly. And then you told Mark Zuckerberg that Facebook.

[Monica Lewinsky]

Right.

[Kara Swisher]

That there was like, Facebook could be used as a propaganda machine. And for that was, if I had.

Been a CIA agent, this is what I would have done. I'm a good. It's not that I have a superpower. It's that I'm a good history major, I guess, because you could watch if you studied communications even for a second.

Yeah.

You understood that every major communication system had a weapon, tool kind of dichotomy. And so it was sort of easy. You know, it's like putting together a puzzle, which is what I would have done if I was an analyst for the CIA or anything else. You just look at all the facts, and then you're like, here's what I think's gonna happen. And I've been more right than wrong. And, you know, just recently with Elon, I said, he's gonna be dangerous. He's gonna be a Trump supporter. He's gonna be this. And, you know, at the time, actually last year, when I said, he's gonna. When he was going, I'm a neutral party, blah, blah, blah, I was like, no, no, he's gonna back Trump and he's gotta pay for it because he's in big trouble if not. And he did. He invested $118 million and it's now he's worth 77 billion more. So. Excellent investment.

Wow.

Including Twitter now, which looked like a bad investment, but now looks like a good one. Because it's not about Twitter. It's about influence and power.

Yeah. He's playing a. What do they say, it's like chess on 12 levels?

Not really. I think he just understands his existential cr. Kamala Harris became the president. I think that was something he was quite aware of.

Okay.

Although I doubt she would have gone after him the way he's gonna be going after people.

Mm, interesting.

Everything these people say. Every accusation is a confession with someone like that.

Wait, say that again.

Every accusation is a confession. Uh huh. He was very tweeting out, you know, they're gonna jail me in the Harris administration. And then right after the election, we're gonna jail mayors. We're going to jail. Alexander Vindman should be jailed for treason. Their accusations are confessions of what they want to do often and always. Not just Elon, but Trump and the rest of them. Yeah, I listen to their accusations quite a bit because it means something about them.

So we're in this what the fuck moment now. Can you give me two or three predictions of what you see coming down the pike now that Trump's president?

A lot of the same, actually. One, more propaganda to try to control certain populations and convince people that bad things aren't bad and the uses of AI and other manipulative means to do it. Two, the continued coarsening of public dialogue because it works for him. You know, either hope or fear works. And he's the fear guy. Right. So I think creating. Creating false narratives constantly and using digital means to do so. And eventually I think tech companies will reign ascendant in this period. He will not pull them back. As much as he has a proclivity to want to do that, I think he's going to be influenced by musk to allow technologists to run the show.

You know what, I sort of wonder just because as you mentioned before when we were talking just briefly of. I've done a fair amount of work in the anti bullying space. And so I'm so disheartened at this moment and at the same time feel like, okay, if the kind of work we can do helps one kid, then. Right. But how do we reclaim social media?

What I'm looking at is not so much where we are now, which is social media is bad for all of us because it's partisanship it creates echo chambers, bullying everything that goes with it. There are some good parts of it. Yeah.

There's some very good parts of it.

Very good parts of it. But mostly it's negative. Right.

I mean, do you have thoughts yet about what we can do to preserve it, to bring back?

Well, it didn't come back. You're saying bring back what? It was never good.

No, I think there was a sense. I think there was always the potential for community. Right. And so. And I also think not only community, but I think that there's, you know, there's a sense of empathy in a way that can be fostered by seeing and understanding other cultures. By hearing more stories.

That's correct. That was the dream of saying aol. Like, one of my first things in the book is a bunch of quilters who had never met, and they liked quilting in their own community. But then they met and formed friendships, and then they made a quilt. That's a beautiful thing. Often it's not. It's to anger and upset people. Cause one of the things I also say in the book is enragement equals engagement. Right? Yeah. It works better than empathy. Empathy does not equal engagement, necessarily. It can, but it does, but it's rare.

Like, the ice bucket challenge, I think, was something that.

For every one of those, there's 10 really terrible examples.

One of the things I wanted to ask you about was around these early experiences you had in your family. And you wrote this really incredible article in 1989. I did for the Washington Post. And there's this quote from there, and I thought maybe you want to read it?

Sure. Oh, this is lovely. I can easily recall sitting on the bathroom floor under the sink as my father shaved in the mornings. I used to put my cheek up against the pipe because the warmth of the water rushing down it was comforting to me. The soft hairs of my father's legs trapped bits of water from the steamy air of the bathroom. And as he shifted his legs, suddenly releasing the drops as he moved, it amazes me that I can recount those times so easily. But not the last night he said goodbye to me. It's a nice piece. Like, it's funny what you remember, right? You know, in the digital world, everything is remembered, but in there, you have bits and pieces of information.

And how old were.

Five.

Five.

Just turned five when he died. Yeah.

Yeah. And it was. And what had. What was the. What happened?

He had an aneurysm.

Okay.

And he had a bunch of things that he didn't know he had and it just hit. He had a headache, went to sleep, didn't wake up. Essentially he woke up briefly when he was in the hospital, but I didn't see him. I didn't see him after that night. Wow. And then when he woke up because of the damage at the time, today would have been a very different story. He probably would have recovered. But then they had very little knowledge of what was happening or ability to do anything about it. They knew about what was happening. And so he had lost his. Much of his brain function. So he would have been a vegetable or akin to that. At one point he woke up and kept calling my mother pretty lady. Like he went back. He reverted to childhood, which was interesting. I mean, what's known about the brain is such an incredibly complex. Beautiful.

And did you. One of your brothers became a doctor?

Yes, he became. Exactly.

Because for that reason, I guess.

Yeah. He had an opportunity to work at early Microsoft. He probably should have taken that job because all his friends who did now own islands in different places. But he became an anesthesiologist. Like my dad. My dad was in the Navy. He was poor or middle class and wasn't able to pay for college. And so the army. The Navy paid for college for him. And then he got out at 34 after he'd served the time. Cause it paid for college and medical school. And so he then had to serve, I guess, 10 years. And when he got out, he had a great job. His first big job, bought his first big house. You know, it was the head of anesthesia at Brooklyn Jewish in New York. And died. Just died. Right. Right then. Right as it started. Yeah. Well, no, he didn't. He had the aneurysm at home. And then they took him away and we didn't see him again. My mom did, but he died very soon after.

Do you wish you had seen him again?

Probably not. I wouldn't have remembered. You know, that's what kills me about memories. You don't really. You have bits and pieces of them. That's something I would love to figure out. If you could access those memories. I thought about being hypnotized and stuff like that, but I think you can't. I think it's like a computer. It just kills the memories, just flush out.

I think if they probably have an emotional charge or a trauma to them, they're probably still in there somewhere, I guess. I think.

But are they accurate? What are you seeing? You know, there's a lot of really interesting science fiction. I've interviewed several authors because it fascinates me, this idea of figuring out what you can see. And there's. Welcome to the Dollhouse. Author Jennifer Egan, she had another book, and her book was about a tech person who creates a way that you can store memories and access them and see them. And the only way you get access to other people's memories is if you store yours with them so other people can see your memories.

Interesting.

And so this, in part of the book, which was really interesting. I love this concept. And would you do it? Would you want to know those memories? Right.

Yeah.

And so one of the things is this one girl has a day, her favorite day, with her dad, and she goes back and sees it and she's like, oh, what a wonderful day. And then she accesses her father's memory, and it is not a happy day for him. And she sees him, what he thought of that day, which was not good. And so that was devastating to her. Like, do you really want to know what people thought of things? I mean, so interesting. I don't know if you'd want to re. Experience lots of things.

I don't want to derail us too much, but I had a really unique experience when we were filming a documentary for the 20 year anniversary of the impeachment, and the director of the doc had foiaed some video.

Oh.

And so they had found this video from when my family and I had gone to a radio address. And so I had a very clear memory of that day. And then they asked me to watch the footage. And I realized in that gap between hearing about the footage and watching it that I thought, what am I gonna do? What the fuck? If it's not how I remembered, it's not right.

Actually, was. It was. Okay, well, you did remember that.

But it was just so interesting because that's such an unusual experience, right, to hold a memory.

And then now we have digital memories of everything. Now just think of all the pictures and the photos and the videos that people take of each other. We do have a documentary going on constantly of our lives. Right. And the question is, do you understand how you felt at the moment? Now I have a memory drop. Like, you cannot believe. Like, not for any good reason. I just. It's good for me. It's my. Everyone I go out with is like, don't you remember that fight? I'm like, I don't. And they're like, I remember it. I'm like, well, I don't. Like, I just. Out of my brain and I'm like, I don't know. Was I mad? At you. I don't remember.

Right.

And, you know, it's a running joke about people I've gone out with. Like, I don't remember. Don't you remember? This was a fight. I'm like, mm, can't recall. And it's good. It's healthy.

I mean, do you think some of that comes from what you experienced with your dad's passing?

Yeah. There's a theory of people whose parents have died at a young age or experienced trauma at a young age. So when you're a young person, very young, and one of your parents dies, half the people you know die. Right. If you think about your relationship to young kids, you don't have a lot of contemporaries at five years old. Right. And so half. Imagine half of your friends dying. So if that happened, and you. You sort of form. It's called highly functional. My brothers and I are highly functional. I would. That's how I would describe us, actually. And you. The worst thing in the world happened, and then you survived. So you're like, oh, I'm not upset by that. Like, it's very hard to upset me. I was just thinking that the other day, like, even the election, you know, my wife was quite trauma, you know, like, oh, God. And I woke up. I had actually gotten sick that night, a little bit of a flu. And so I went to sleep. So I didn't watch it, so. Which was good. And I woke up and she's like, oh. I was like, oh, well, next. Like, I was much more in the. Okay, now we're on to the next thing. And I think it has to do with that. I know we'll be fine, or we'll figure it out or something like that. Cause you've survived and you're fine. Or not fine.

And does some of that come from. Because I know that there was then that point where your mom got remarried.

Yes. A terrible person. Right. And so he's still not dead?

Oh, he's not.

Okay.

He's tried to be. Are he and your mom still married? No.

No, no, no, no.

Okay.

No. They broke up.

You said he was cruel in ways I can't even explain.

I can explain. I mean, I think you went like, you know, he got rid of my dad's dog under very mysterious circumstances. My dog had a basset hound named Prudence. And suddenly it was there, and then it wasn't, and he got rid of it. And I don't know how. I still don't know to this day. I wish she would tell me. If you're listening, you terrible person. How would you do that to children? Now that I have children, I literally. If I could like hunt him on the savannah, I would like that kind of thing. I think that, you know, you. He did all kinds of cruel things all through his life. Just if someone. He was jealous of us as a unit for a short time and therefore sought to. I'm very. I understand Trump completely. It's dividing people. I understand people who divide. And so he was one of those people and stuff like that all the time. Very insulting. I mean, one terrible thing he did to my brother was. My brother was quite.

Jeffrey.

Jeffrey was a bit arrogant about his grades. He had perfect grades. And then he got eight hundreds on his SATs. And you remember those days, right? Oh, yeah, right. No one cares now. But then it was a big deal. And getting into college was easier. But you cared more about those, weirdly enough. And so my stepfather got all. He applied to a bunch of schools and he got all the letterheads from all the colleges that Jeff applied to and sent him rejection letters. I know, right, right.

Like, are you serious?

I am serious. And Jeff got one a day. And you know, she's a 17, 18 year old kid. Like, what? It's abusive. It's crazy.

Oh my gosh.

I thought it was funny. My mother also thought it was funny. We did not think it was funny. My brother and I did not think it was funny.

Why did your mom think it was funny?

Because my mom's a bit of a sociopath, I would say. Okay, you know something, you know, just narcissist again. I know. Narcissism. Yeah. And so it was, you know. Cause she was in love with him. Like, you know, that happens a million times.

Yeah, I understand falling in love with a narcissist.

Yes, you do. Exactly. Right? What do you do? And she's a narcissist herself. And so he's a malevolent one. I don't know what's going on with her, but partially malevolent. And so, you know, I've never thought that was funny.

It's not funny.

My brother sometimes laughs about it now. Cause he's older, he's like in his 60s. Like, who cares? He did great. But to do that to a kid, it went on like that. Like, you know, we lived with a lot of wealth and he would lock everything, like. And he would tape things in the house. Everything. He just. It was tape.

Like tape it down or.

No, no, no. Tape put bugs in the house to hear us. So my brother and I used to make up drug deals all the time. Okay. I've never taken any drugs. I'd be like, I've got the stash of cocaine and the thing, like. And my brother's like, okay, I paid 50 for it. Like, what? We would make it up. Cause it was. But that made us resilient. I hate to say it. You get resilient through negative things, which is interesting.

And did you guys have gallows humor?

Yes, very much so. We also had very supportive. My grandmother was incredibly important to me. We had a lot of supportive people around us too, at the same time. So I bounced back a lot quicker than other people because of all this.

How did you know with your stepdad to trust yourself and your sense of self instead of what most young people, which is absorb the negativity that an adult is giving to them?

I do think, you know, one of the things I realized when my son was 5 is how much he knew me. So I must have known my father very well, right? I don't remember it, but we were so tight. And my daughter and I are. She's five, very tight. We know each other so well. Therefore, he imprinted on me before my stepfather could. And so I knew what was good and there was no changing that. And I do think kids get a lot in the first five years of their life. And so I remember my son turning 5. I was devastated because I finally understood my devastation through my relationship with him, and I got it right away.

[Monica Lewinsky]

Thanks so much to Audible, our presenting sponsor this year. Why not let Audible expand your life by listening? Explore over 1 million audiobooks, podcasts and exclusive Audible originals that'll inspire and motivate you. Just open the app and tap into your well being with advice and insight from leading influencers, experts and professionals. You'll find titles that enrich your life, relax you, and the ones I like best, titles that make you laugh. Whatever your focus or interest, there's a listen for it on Audible. Ultimately, it's all about starting good habits. Making a positive change is the best goal you can make for yourself. And Audible can help. There's so much opportunity and more to imagine when you listen. Let Audible help you reach the goals you set for yourself. Start listening today when you sign up for a free 30 day trial at audible.com reclaiming thanks so much to our sponsor, Reformation. I want to take a second to talk about one of my favorite clothing brands, Reformation. You've probably seen Reformation on Instagram or at a wedding. They make the best guesting dresses. But if you're like Me, you may have thought that's all they do. Well, you're in for a pleasant surprise. Last year they worked with Yours Truly and Vote.org on a campaign to empower voters to take part in the democratic process and show off their workwear. From doing the campaign and getting to know the brand even better, I love their sweaters, blouses, workwear, shoes and bags. But most important, I love how confident I feel in their stuff. Plus, it really holds up since they make everything with super high quality, sustainable materials. Reformation is also a brand that uses their growing platform to do good in the world and especially in the sustainable fashion space. As they say, being naked is the number one most sustainable option. Reformation is number two. If you're looking for clothes you want to feel great in and feel better about, head to reformation.com I think I.

[Kara Swisher]

Read a quote I'm in butcher it. But the gist of it being kind of like when you've lost a parent at such a young age, like, you can't give any fucks anymore. There are no fucks anymore because you're.

Old and you understand disaster and mortality at a very young age. A lot of kids go through this around the world in different circumstances. And one of the things, another thing that I think about a lot is mortality. I think about it all the time. Death is something that's ever present. I respond to it well. And instead of, I'm very aware of how long, short time we have on this planet, even if we live a long life. And so everything I do when I'm doing something and I sort of don't like it, I'm like, oh, I'll be dead in 50 years. I'm leaving. Like, I have a very good decisive thing. Like, I was in a job I didn't like. I sort of liked. And it was a very high profile one. And everyone's like, oh, you have to stay. I'm like, I really just don't like it. I don't like these people. And I decided to go. Like, I do that very quickly. I make decisions very, very quickly. And the person at this place was asking me why I was leaving. Because it was a high profile job. And I said, you know me, you know, just me. And I was trying to be polite as I can. I'm not very polite, I'm not impolite. I just honest, I guess. And they said, why are you leaving? And I said, all right, if you want to know. And I said, okay, tell me. And I go, I don't want to talk to you anymore. And they're like, what? And I said, I have, you know, so many minutes on this earth, and right now I'm wasting them on talking to you, and I just don't want to talk to you anymore, ever. And they're like, wow. And I'm like, yeah, that's really it. I'm tired of talking to you. And I haven't talked to them since. Wow. Feel good about it.

Okay.

Yeah.

And how do you.

I like talking to you. You're not wasting my time.

Oh, great. Well, thank you.

I won't waste my time. I, like, walk out of things. I'm like, I have to go now.

I'll try to not piss you off.

No, you don't. It's pissed off. It's like, literally, I'm aware of how many minutes. You know, I always say to my kids whenever they're super slow in getting to school, like, putting their shoes on takes 10, 15 years. And I often go, TikTok, TikTok. Minutes of my life are ticking away, and we're still putting on our shoes. Like, let's get going. And they laugh about it. And so they always go TikTok.

To me, it was interesting. I read somewhere this. Just this sentence or statement, whatever about that. We never know when our last breath is.

We don't.

And I just thought that sort of reframed.

I have an app on my phone called. Called Wecroak, which I love. It's a little frog.

Wecroak.

Wecroak. It's my favorite app on my phone. Look, there's one coming in, has a little frog on it. And Bhutan, if you think about death five times a day, you're happier. Cause, you know, you're like, oh, I'm gonna die. So I'm gonna do this. I'm gonna not do this. I'm gonna make better choices.

I mean, is it, in a way, is it jiu jitsuing, like, how people experience death?

It's a Buddhist thing. Like, you realize that everything is ephemeral, right? That ultimately stuff everything. Like, I've never been a money person. I was offered a lot of Internet big. I would have been very wealthy. And I just didn't want to be with those people. And I know it sounds dumb. I make enough money, like, you don't need 10 billion if you have enough.

I remember I was asking you if you knew anybody single at some point, and you were like, here's the deal. If you end up with someone I set you up with and they have a plane, I get to Ride on the plane whenever I want. I was like, that is a totally fair deal.

You know, I did the Succession podcast. And one of the great things about Succession, the writers on all these theater writers. There's a lot going on there if you rewatch it, actually. But one of the things they did really well was create. And I have witnessed this with all the billionaires. I know so many billionaires. I know so many billionaires is. I can't believe I just said that, but I do. But one of the things they do, the people's worlds got smaller and smaller and more and more. So it's Kashmir prison, right? So they were in tight places. And then they go. They go from their expensive apartments that are, like, airless to their cars that are airless to their planes that are airless. And, like, they move and never touch anybody else. And this is what's happened to a lot of the Internet people. They don't experience real life in any way. The thing they love to talk about in tech is, let's get rid of the friction, right? They're always like, let's remove the friction. And they want you to remove the friction. Cause it's addictive. Frictionless environments are addictive. And you need friction in life to be a good person, to be an alive person.

Why do you think that is?

Because it creates. You know, edges are important because it stops you and it makes you. One of my favorite books is the Trial by Franz Kafka. And it's supposed everyone thinks it's about communism, but it's not. It is not. It's about existential crisis, right? And where you are. And the first line was, someone must have been telling lies about Joseph Kate because he was arrested one fine morning. Something like that. The word arrest means to stop. It's about God stopping him. And the last image is of someone trying to get him to stop. And he never does, this character. And I just think you have to stop sometimes and you have to pay attention. And if you're in this wealthy environment, you just don't. Because everything is brought to you. Everything is comfortable. No one disagrees with you, and you become a warped version of yourself unless you have incredible character. Elon Musk is the opposite. He's removed anyone who disagrees with him from his environment. And therefore, he's in desperate need of attention and love.

He sent you an email, right? What was this?

You're an asshole. Because I disagreed with him. In fact, in that instance, I had agreed with him. But he was so far gone that he thought any Sense of tweeting something where I agreed with him was of someone that disagreed with him was disagreeable. It was crazy.

Yeah. I've only met him once, but I was seated next to him at the Vanity Fair Oscar dinner one year. So this was pre Pandemic.

Yep, I remember that one. Yeah.

And it was.

He was single then. He was. He asked me if I knew I had to fix him up, but then I said no because I thought he was nuts.

But here's what was really interesting to.

Me, it's just Pre being the richest man in the world. He wasn't at the time.

No, no. This must have been 2018.

I remember 18.

And so it was so interesting because he answered every question I asked him.

Yeah. He used to be that way, but.

He didn't ask me any questions. And it's like a really long dinner. So I basically took to just pretending he asked me the question. I asked him back, and then I answered, oh, wow. Because I was like, how does he.

Have a conversation this way?

So, I mean, I had asked him about, like, if he hadn't become Elon Musk and Tesla and all that would it. What would he have wanted to be? And so he said a science fiction writer.

Yeah, he loves science fiction.

Yeah. So he said he used to write it when he was younger.

He did. But it's just a knowledge base in that area and video games and things. He's quite good at video games. But, yeah, I think. You know, do you feel like you.

Sort of got like a Jedi School? Went to a Jedi School for these kinds of Elon Musk's and the others.

[Monica Lewinsky]

What?

[Kara Swisher]

Yeah.

From your stepdad?

Possibly. Possibly, yes. It's interesting. I just. I'm not. I don't know if it was from there or just the way I was. Cause I was never impressed by anyone unless they're impressive. Like, I treat. I will treat a janitor like I'll treat a billionaire. Right. Just depending on the person. And by the way, there can be a lot of jerky janitors and a lot of nice billionaires. Like, I don't assume anything about them, except that if you're very wealthy, you do have a lot of. Yes. People around you.

Yeah. One of the things I think that surprised me in reading your book is that I now knew you. So I knew you to be. But there's sort of a mushy part to you as a parent, which was a little surprising to me, I think, like, I knew you loved your kids, but there's a real.

I love my Kids. It's the best thing I've ever done. It's the only thing I think worthwhile. If I had to pick. If you had to. You don't have to stack rank things in life. But if they said if you have to pick, it would just be the kids, that would be it. I've had a great career. I like my career, by the way, and I think it's great. And so. So I think just having them. I've always wanted to have kids since I was very young. I bought, as I wrote in the book, I bought a onesie when I was in college. Cause I was like, I. And being gay and having kids at the time was not something you thought you could do. So that was another thing. You know, you'd have to get married if you wanted to have kids. And so I was very much intent on having children. And I don't know why. I just always thought I would be a good parent. And I think I am. And I wanted a lot of kids. And so when I remarried and Amanda was like, well, here's the thing. I want to have kids. I'm like, great. One of the regrets. I don't have very many regrets. I don't have almost any, except for this one, which was, I wish I'd gotten pregnant again. I liked being pregnant. I loved it, actually. It was one of the best experiences I've ever had. I know a lot of women don't, but I did.

What did you love about it?

It was so cool. It was so cool to have something moving inside you. I wish men could experience. They'd be a lot nicer these days. Just the creating of life was really astonishing. It's a miracle. You got to know your body better than you ever did. You understood it a little in a different way that I hadn't. We're so out of our body now. And in that case, you're forced into your body. I learned lots of different things, negative and positive. You know, at the time when I was getting pregnant, I bought a bunch of sperm and I went to visit one doctor. It was a man. And he was like, ah, geriatric pregnancy. That's what they call it. I'm like, excuse me. I pay attention to words. I was like, excuse me. Oh, well, you know, you worked so much that now you might not get pregnant. I was like, go fuck yourself. And I got pregnant the first time. I like. We ran this thing like it was a space launch, like, nothing's going wrong. And it was so offensive to me that I was like, Revenge pregnancy. I'm gonna get pregnant right away. And I did. And now I own a ton of sperm that I don't know what to do. Same thing with my ex wife. She got pregnant first time. Yeah, that's me too. Good. My eggs. Oh, he did too.

Yeah. And I did. And my doctor had me do. And I did around or we used some of the eggs and made embryos and that whole process of like buying jizz on the Internet.

Yeah. At the time I was weird. I did it the old fashioned way. I did it the old fashioned way. Just an iui. But it was just great. I liked it. I liked being. I was like a little hippo. I liked Louis kicking me. One thing I used to love to do is I love Law and Order. Watch it all the time. Relaxes me. And you know the ding, ding, that noise. So I used to. I was huge and I put a sandwich on my belly. Cause it's a great place to put a sandwich when I was watching. Cause it was big. And every time there'd be a ding dung, Louis would turn and I love it. I'd be like so amazed by it.

What happens now? If he hears the.

I think he knows that. I don't know.

Okay. I think that's an experiment to do. Like to watch Law and Order with him and see if he twitches or something.

No, he doesn't. He doesn't. But I was amused by the entire thing. So.

Yeah, it's. You talked a bit in the book too about how your experiences. Sorry, I keep going back to when you were younger, but it's.

It's super fascinating to me.

Even though you were 5 and I was 24 when I. But this idea of distraction in these sort of. In those traumatic events that put you on a different path.

Yeah, that was it. That was the one. You know, it changes everything. It changes everything. And it changes. I really think I'm successful because of it, Even though I think I probably would have been less successful had my dad lived. Because I would have felt safer. But feeling unsafe is not understanding. Lack of safety is a terrible way to learn things. But you learn them quick. And you also learn that you'll be. You can put one foot in front of the other. I think that's the thing. And you have limited time. All those together. And then later, when I had my own stroke, it was further emphasized that like, guess what? Anything can happen at any time. I'm very aware of randomness. I'm very aware of death. I'm very aware of chaos. And I'm comfortable with it.

Yeah. You have a tattoo, right?

With several, yeah.

Okay. I was so surprised. I did not peg you as a tattoo.

Hold on. So does my son. So I have one over here that I don't like. It's a ginkgo leaf. It thinks it's a sham. It's my first one. Yeah.

I was going to say it's a little like a shamrock.

How would I do a shamrock? How dare you think I would put a shamrock on myself? Come on.

I know. That's so boring.

Ginkgo is the oldest tree in the world. It's one of my favorite trees. And everyone thinks it's a shamrock. So I hate that tattoo. It also is somewhere I can't see it. Tattoos are for me, so it should have been on this side so I could look at it. And I enjoy looking at. They're my tattoos.

Well, maybe you should get rid of that one.

I can't. Now it's there, it's gonna go with me to death. So then I got all my kids, which are Alex, Saul, Louis, and Clara. I had Louis and Alex for a long time. Then I added these two. They're little hearts.

They're like your Wonder Woman bracelets, right?

Exactly. But then I put on these. Louis got me to do this, but I told him he could get them at 18. He's like 6 now. So this is entropy. Chaos. Chaos. Entropy and syntropy are the two contrasting forces. As everything is destroyed, it is created. So everything. This idea that everything's on its way to something else is a really comforting feeling. Like every cell of your body is gonna be an apple someday or whatever. I'm totally aware. You know, eating the worm of a fish. That King story or whatever. So everything that's destroyed gets created into something else. And so the world is constantly push pulling between creation and destruction. Indian Ganesh is like this. There's all kinds of stuff like that. And that appeals to me. The idea of it'll be okay long after we're gone, this will become this, this will become that. And it's a very comforting. If you're not religious, it's very comforting. I'm not religious.

How did that devastating loss when you were so young end up becoming something that was like a superpower for you?

I think you're not gonna like the answer. I don't think it is a superpower. I think the loss is the loss. And I have never recovered from it. I think of my dad every day. I understand the giant hole left, and I've Talked to a lot of people who have lost a parent or a parent who has lost their partner. And then the kids are young and they're like, what. What can we do? And I said, nothing. Nothing. It's. There's no. There's no good part to it whatsoever.

When I read that bit in the Washington Post, it was like, I just wanted to pick up little Kara and put you on my lap and give you some cuddles and.

And he was a wonderful person. It just was bad. There's no good. There's no good to come of it. And I guess, like, I'm resilient. I'd rather not be resilient. I'd rather not be that way. I trade it all.

Do you think he would have ended up as the same. No person.

I would have been nicer and maybe not as successful. You know, there's an element of not being nice to be successful or being. Cutting through stuff. Willing to cut through stuff.

This reminds me of. So I had this funny experience reading your book, which is, I like to go out to dinner by myself sometimes and read. And I laughed out loud. So it was so loud that I had to apologize to the people next to me.

Never apologize. Apologize for laughing.

I know, but, you know, other people are. I was at Bungalows, and so it was like, you know. And you were talking about your prick to productivity ratio.

Yeah.

Okay, you explain it. Cause you'll do it.

I have this thing where I decide whether. Is their prickishness too big to account for their productivity? If they created something that was amazing, how much of a prick can I take? And I'm leaving out pedophilia and stuff like that here. But it's behavioral, like Steve Jobs could be difficult. He parked in handicapped parking space. Now, today he looks like a gentleman, and he was in many ways. But he was heavy on privacy, created all these amazing products. So he has a product he wins on. Productivity versus prick. Right. His prickishness was not so bad. Other people's prickishness can go up and their productivity goes down. And so I just would do that, and that would be my justification for speaking to them. Now I have. I've got to make a new one. Because someone was like, would you interview blank? Right? And I'm like, no.

How about a chode chart?

Chode chart? Yes. Like, would I interview? Cause some people are just bad narrators. They're liars. I have a hard time interviewing active liars. Like tonight I was supposed to be on a CNN panel, and there's three people I have no respect. And I'm like, I can't. I just can't. And they were like, you're good. You know, you're good at slapping them down. I'm like, I'm mad that I'm good at that. I don't want to be that. I don't have to be a. It's like, you're good at shooting people. I'm like, mm, don't wanna shoot anybody. Like, we'd prefer. I know I am, actually. And so I get claps for slapping down bad people.

With all the discussion about men and the men in technology in Silicon Valley, what do you think the tech world, and in particular social media would look.

Like if we had had women, if.

It had been run by women?

Well, it's interesting because it's a very misogynistic. It's not even misogynistic. It's not anti women. It's no women. It's different. Like, some of them are misogynists, no question. But it's not quite as crystal clear as that. They think they're better. That's all. Like, it's different than just hatred. Cause it's very easy to do hatred, right? It's very. It's like, okay, you're a terrible person. It's more that lesser than. Is the. And that's different. Is that hate or is that they just believe it? They believe and they believe in themselves so much and their rightness. I always say they're frequently wrong, but never in doubt. And they're so certain of what they're like. Sometimes I think AI is really interesting to me because I'm spending a lot of time dealing with all these AI people. And they're the same people, by the way, FYI, who created our last Internet. And one of the things I think about a lot is why there's a lot more men using AI than women. It's a really interesting statistic. I have decided this is my new theory. I don't know if it's right. Men can't create life. They can't. And by the way, there's ways to be pregnant now without sperm. There's really interesting innovations happening there. Yes, there is. What? Yes, 100%. It's really. I'm doing. My next book is on all these things.

Okay.

And so men can't actually create life and they can't sustain it to birth. AI is so they can make life. They want to make bots, they want to create beings. They want to create beings. It's their way of Being pregnant. I know it sounds crazy, but I think about it.

But is it also. But then also about the control?

That's correct. So when you have a baby or you're raising a child, you don't have control, really. You do a model of control, but you don't. You don't know how they're gonna end up, what they're gonna do. They're the most random shit. Kids do the most random shit and you don't know what's gonna happen. Like, what they're gonna like. My son had to take off his coat four times yesterday morning. Cause he didn't like this. No, I wanna do this. You don't know what's happening and you don't know why. And you know. And that's good. That's the friction, like I'm saying. And so you can't guess it. You just can't guess what's gonna happen next or which way they're gonna go. And with AI, you can control it, although now they can't. Sometimes they can, but they can't. And so they are giving birth. That's why they like it. Right. So why is it so. I just find it just. I'm thinking a lot around, why is AI so popular with men? Like, and it is like, there's just study after study after study. And I believe they. I think it's them being pregnant, which is the greatest thing you can do, really, if you. Creating life is really the top level. I think space is about that. I think going to their penis rockets and everything else I do, I'm like, everything is about creating life, which they absolutely cannot do. They cannot.

What is something that you have lost that you would like to find or reclaim or recreate? And it could be a physical object, a place, or a part of your identity.

Oh, it would have to be my dad. That would be it. You know, maybe my kids being really young, I guess again, my older kids being young, I really am enjoying doing it the second time. With the age difference, I think I didn't relish it quite as much as I should have and relish them as much as. I mean, I spent a lot of time with them now and we're very close, so I don't feel like I did a bad job. I just wish I could go back to that. Go back in time and re. Experience things. I'd love a time machine.

Me too.

Wouldn't you?

Oh, yeah, me too. Kara. Thank you so much for having us, Monica.

You're a great podcaster.

[Monica Lewinsky]

Reclaiming with Monica Lewinsky is hosted and executive produced by me, Monica Lewinsky Production Services by WTF Media Studios. Our theme song is by Ben Benjamin and our music supervisor is Scott Velasquez. Our story producer is Elna Baker and our senior producer is Megan Donis for Wondery. Eliza Mills is the development producer. Our managing producer is Taylor Sniffin. Nick Ryan is our senior managing producer. Senior producers are Candace Manriquez, Wren and Emily Feldbrake and executive producers are Dave Easton, Erin O'Flaherty and Marshall Louie.