This week on Reclaiming, we welcome renowned tech journalist and industry expert Kara Swisher. Kara offers a thoughtful prediction on the political landscape under Trump and Musk. She drops a provocative take on AI's gender problem and why she believes men are at the heart of it and she even shares her personal reflections on pregnancy. Don't miss this no-holds-barred conversation with one of Silicon Valley's most influential voices.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to Reclaiming with Monica Lewinsky on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/reclaiming-with-monica-lewinsky now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Chapter 1: Who is Kara Swisher and what is her impact on tech journalism?
Wondery Plus subscribers can listen to Reclaiming with Monica Lewinsky early and ad free right now. Join Wondery Plus in the Wondery app or on Apple podcasts, or you can listen for free wherever you get your podcasts. Hi, hi. Monica here. For today's episode, I spoke with my badass friend, Kara Swisher.
You probably know her as a tech journalist, an author, and host of both 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. Thank you to our presenting sponsor, Audible. Visit audible.com slash reclaiming 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, welcome to Reclaim. Thank you. Thank you.
For anyone who doesn't know you, can you give them context?
Who doesn't know me?
I'm kidding.
No, I've covered tech for the past 30 years. I was one of the earliest people who covered the internet. I know about the early 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 then through our mutual friend, Brooke Hammerling, a bit more. Then you kindly were interviewed for a documentary on public shaming cancel culture. Yes, for that great documentary you did. Thank you, that I exec produced.
And we still didn't meet in person because of COVID then. And then the first time we actually met in person was when you interviewed me for Sway. My favorite interview.
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Chapter 2: How did Monica Lewinsky and Kara Swisher become friends?
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 800s 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. Yeah. 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, this was 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, just a 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 never thought that was funny.
It's not funny.
My brother sometimes laughs about it now because he's older. He's like, in his 60s, he's like, who cares? He did great.
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