On top of everything else working moms have to juggle, our nutrition is not something we have time to prioritize. That's why Weight Watchers is here. With over 200 zero-point foods that you don't need to measure or track, achieving balance and weight health is easier than ever. Plus, through Weight Watchers clinic, if eligible, you can now access doctor-prescribed weight loss medications and get support from a dedicated care team, board-certified doctors focused on weight care, one-on-one consultations with a registered dietitian, medication management, such as navigating medication shortages, and more all through the Weight Watchers app. Weight Watchers fits your needs, whether it's through their clinically Proven Points program or for those that medically qualify, access to doctor-prescribed weight loss medications and registered dietitians in Weight Watchers clinic. See how Weight Watchers fits you at weightwatchers. Com. We've all felt the need to settle for a slice of life when what we really wanted was the whole damn pie. That's what Amalia Martino is serving up for you. Whether it's health, fulfillment, or promotion, Amalia and her guests remind you that you don't have to settle for less than what you want. Join Amalia Martino, founder and President of the Vita Agency, every week on the Whole Damn Pie, as she speaks with guests to uncover the secrets of living a more fun and balanced life.

Listen to The Whole Damn Pie wherever you get your podcast.

Lemonada.

This is the Inspiring Women Leadership Lab, and I'm your host, Lori McGraff. For 30 years, I've been a leader at the intersection of healthcare, technology, and innovation. For all of those years, I've wanted more women leaders at the table. Because when women lead, we build better businesses and a more just and equitable society. Sure, things are changing, but they're not changing fast enough for me. Even today, did you know that less than 2% of all of the billions of dollars of investment funding that's out there goes to businesses with female CEOs? Did you know that only 10% of investment partners are women? So there are real headwinds. So what? Now what? This is our time. It is beyond time. And that's where the Inspiring Women Leadership Lab comes in. This is a master class for women CEOs, entrepreneurs, and business leaders. Every week, I'll be talking to a visionary guest to get practical advice, inspiration, and essential tips to help you launch and lead impactful, winning businesses. The best and most successful business leaders need to be a lot of things. Relentless, confident, decisive, unapologetic, and unapologetically themselves. My guest today is veteran journalist and entrepreneur, Kara Swischer.

Kara parachuted into Silicon Valley 25 years ago with her cleats on, and she took the advice of her mentor and then business partner, Walt Mossberg, to heart. They'll never know what hit them. Be fair, but cover them hard because they're going to run the world. Kara knows and has taken to task every tech titan that there is. Jobs, Bezos, Musk, all the marks, Benioff, Cuban, Zuckerberg, Vice President Kamala Harris, former Secretary of State, Hillary Clinton, and on and on and on. Anyone who is someone in business, tech, or media knows Kara Swisher or wants to know her, she is the O G of telling it like it is, hard-hitting, fair, and without apology. Today, Kara and I discuss her 2024 memoir, Burn Book, A Tech Love Story, in which she reflects on her 25 years covering Silicon Valley and on the quality she has and every CEO needs to have for maximum impact and success. All right. I'm going to just dive in here, Cara. It is amazing to be talking to you today, and I so appreciate having you on this Inspiring Women Leadership Lab. Thank you. And you started with, You're a if you're not somebody.

Com. Cara, can you tell us where the love of tech began?

When I was a reporter at the Washington Post, I was covering retail, which was really getting hit hard by the advent of technology used by Walmart, which was changing everything using... And technology was at the heart of it. A lot of things are at the heart of Walmart, but one of it was the incredibly deft use of technology to understand what was being bought and sold. But I saw regular business is getting decimated by technology. I was the young person at the Washington Post. And so they said, Oh, there's this digital thing. It was called online at the time, online services. Maybe you could do it. And so it was largely because I was the young person on a news staff that they thought I could understand computers, which I didn't have any particular knowledge of. The minute I saw it, though, it was really clear to me that this was one of these moments, that it was a worldwide network of information. And anyone studying communications understands what that means, whether, again, it's television or radio or anything else.

You also had a choice, though. You had a choice in terms of... You were always somebody when you talk about your early days of your career, you were always pursuing the next advancement, the next opportunity. And it seemed like in journalism, which is what your profession was in the early days, it was the way to get to the top was politics.

Politics at the Washington Post, at the very least.

And you had that opportunity, but you chose a different path.

Yeah, I didn't. I covered parties for the style section of the Washington Post, and parties were a way people did politics in Washington, all those parties. You could watch it up close in a social setting, which I think is important to understand. It's less so now, obviously, but then it was critically important. I thought it was very insular. I thought it was full of compromises by the reporters. It It wasn't the future, that's for sure. They were running the world in a way that I thought was not the way I would run the world. I just didn't like it. The minute I started covering online, I really understood it. It was a bigger thing that was happening. I had been a student of communications at college, and therefore, I think I understood more than most people the implications of what was coming.

I think you also were really clear that this was going to be much bigger, and even there were times of doubt along the way. It wasn't always as obvious as it actually is today.

Well, I guess it is. When I was looking at computers, it was so obvious what it was going to supplant, typewriters and all kinds of things. They had a teletype machine I wish to yell at. I'm like, Why is that here? It comes over the computer. I was one of those people who were always like, Why are we using this versus this? I wouldn't say I was a technologist. I just understood that I had a very strong awareness of replacement, that things get replaced, that the car changes towns, changes stage coaches. I was very aware of that. I was a history buff, and so it's hard to study history without understanding how civilizations are built upon each other.

If we can talk, Cara, about some of the traits that you are known for in terms of just what allowed you to absolutely break through. I mean, one of the things that I'm fascinated with is just your deep, deep understanding of who you are and always this view that you would be somebody, somebody who would be relevant and doing more and better work than many others that you worked with. Can you just talk about where that confidence comes from? Certainly for most leaders, sometimes it's deserved. The way that I understand how you think about it, and this is from a lot of listening to you over many years, it seems like it comes from just a belief in yourself and a couple of things, the traits that you've honed.

I think people are inherently the way they are, right? I think there is an element having... I have four children, and they're the way they are. They're really not born that way. You can develop skills, and obviously, trauma or joy leads to... The good parenting leads to good outcomes in that regard. So you can hone what people are like, but people are like the way they are when they come out. I think I just was this way. This was my nature, and I was confident. I think part of it had to do with being gay from an early age. As far as I can remember, four years old, I understood I was different in that regard. I had a different... I didn't look at the world in terms of men, I guess. I think a lot of women get oriented that way pretty quickly early in their lives, probably in the teen years or 10, 12 or something like that. I always felt that wasn't part of my thinking. I didn't have to do that. I didn't have to please people and particularly men. I really liked myself. I know it sounds crazy, but I really thought I was interesting.

Because women weren't supposed to compliment themselves, I complimented myself a lot. Not when I was unnecessarily. It was when I was good at things. That was one thing. I think probably my dad dying had a lot to do with it. I'm very aware of time passing, and so I didn't have time for all kinds of that. I had a tough mom, and so she was at me a lot, so I had a good pushback. I developed that a lot of ways. Sometimes that could crush people, right? But it didn't. It did the opposite.

It was much more- Well, you've talked about how with your father passing away so, so until abrupt and unexpectedly when you were five, that it was just a matter of one step in front of the other. And you have had some hard things. You talk about your stepfather who was very, very difficult as giving you the gift of understanding gamesmanship. And mind fuckery, I think, is the term that you used in terms of just how you dealt with it. And you've also said many times, But no one should feel sorry for me. You don't have a sense of feeling sorry.

Those were all- I don't have time. Yeah.

Can you talk about that? Because that time is so important.

I do understand time, or at least I appreciate it. I think someone was telling me when I was very young how many minutes I had left to live, and I was like, Oh, Okay, so I can't waste them. I think it was very clear, and I think it emphasized that with my dad dying. The other thing was it was really... Again, I don't want to negate the innateness of it, but there really is Through tragedy, you can get very strong. It's a way a lot of people whose parents died at a young age, they're something called highly functional. I'm very functional. I think that when bad things happen, I don't get like, Oh, no. All right, now what? That Now what? Right. And so that should be the name of my book, Now what?

So let's talk about inflection points, because you've had a number over the course of your career, and you also talk about any inflection point for you starts with belly aching, starts with waking up every day, wondering if you like what you're doing and if enough days have gone by that you haven't, it's time to do something different. Can you just talk about how you actually take those opportunities? Some people don't.

Many people don't. They They like to belly ache. People enjoy belly aching. I don't. I find it the worst part of my person. I don't even do it. I don't go, Oh, no. I started to become intoler to belly aching almost as I get older. I'm like, Oh, for goodness' sake.

It's that time thing again.

I have also a very big sense about how small we are in this universe. Again, come on. There's been people here before. We're going to be here 100 years at most, and then the next 100 years. I have a bigger sense of time beyond that. I find belly aching a waste of time, a very big waste of time. Often when I'm in a job or something, if I go, I don't like this, I quit. I'm not shift to shift. I'm like, sometimes kids, they change hobbies over and over again. I don't really care that kids do that. A lot of parents do, but I don't care. If they don't like it, they don't like it. If I don't like what I'm doing or I'm not enjoying it enough days in a row or I keep complaining complaining to myself or others about the same thing, I pretty much stop. I'll be like, Okay, then we'll have to either change it or we're going to have to go. I don't find going a problem. I really don't. First of all, I think I'm highly educated and I'm healthy and mentally alert. Those are things you can't control.

I have options. I think a lot of people, especially those with options, act like they don't have options. I find that I don't understand it. I feel like an alien sometimes. I'm like, well, you don't like your job? Leave it. And they're like, well, then this. And I'm like, Are you really going to not eat? I don't think... Not eating is always my criteria. Are you not going to be able to... Well, maybe you're not going to be able to live in this big house. Okay.

But that belly aching that turns into those inflection points. And you've also talked about the need for next. And I think that's such an important, just an important statement, because whether it's confidence or whether it's just annoyance, just like needing to do something next, that drive seems to have never left you. And that, to me, has been like a through line for you as you just continue to push.

Yeah, I think people get bored with their work and they just phone it in. And whenever I feel like I'm phoning in and I leave, I don't think that's interesting. I don't think that's interesting to me mentally. And they do it out of safety. I don't think the world is safe. So I just don't. I never thought it was. I don't think everything is assured. And again, that probably goes back to my dad dying. He thought he had just gotten out of the Navy. It had finally paid for his education. And then he had this great job and he just bought a house. Well, that was that. And so I don't know. I also like to enjoy myself.

But you push. You're pushing people, too, and it's impactful. You can hear it when you talk to these tight ends or everyone that you're holding accountable. It's accountability.

Right. Absolutely. I think you're just like, Are you going to do something about it or are you going to stop talking about it? One or the other. You have two choices. I think a lot of people, they wallow in that when they're really good leaders don't, actually. They don't wallow. They just are like, okay, now. I think I'd be excellent in a survivor thing. I'd be excellent in a... When they have that round the world trip, I'd be like, okay, now what? Where's the tool we could use? I used to tell friends, I'd be good in an Apocalypse. I'd be like, All right, what are we going to do here? What's going to happen? I don't know. I just don't know where it's from. It's also interesting to change, and I think people are scared of change in general.

The Inspiring Women Leadership Lab will be right back. This show is sponsored by Betterhelp. So, listeners, what are your self-care non-negotiables? Maybe you never skip leg day at the gym or a therapy day. When your schedule is packed with kids' activities, big work projects, and more, it's easy to let your priority slip. When you feel like you have no time for yourself, non-negotiables like therapy are more important than ever. We know that therapy works. Making time for therapy is one of those things that just makes a lot of sense. It's always worth it, and I highly recommend using that time each week to step back and take a breath. Betterhelp is an online platform that makes therapy accessible and convenient. You can do it from the comfort of your own home on a schedule that works for you. Just fill out a brief questionnaire to get matched with a licensed therapist, and you can switch therapists anytime time at no additional charge if you need to. Never skip Therapy Day with Betterhelp. Visit betterhelp. Com/inspiringwomen today to get 10% off your first month. That's betterhelp, h-e-l-p. Com/inspiringwomen. Today's podcast is sponsored by Midi Health. There's so much that we don't talk about as women, especially when it comes to topics like perimenopause and menopause.

Oftentimes, it comes and we don't even realize that the symptoms we're facing are actually tied to our hormonal changes. I've experienced so much I wasn't expecting to as I aged, and we really don't prepare the women in our society for any of it. If you are a woman over 40 and you're dealing with hot flashes, insomnia, brain fog, moodiness, vaginal dryness, or weight gain, you don't have to accept it as a given. That's why I want everyone to know about Midi Health. They are clinicians dedicated to providing safe, effective, FDA-approved solutions to support the natural hormonal changes of menopause. What's even better, Midi is covered by insurance. With specialized insurance-covered care, Mitty puts relief within reach for more women than ever before. Schedule a virtual visit to discuss your symptoms and health background in-depth today. You'll come out of the experience feeling heard and with a plan to start feeling better. You deserve to feel great. Book your virtual visit today at joinmidi. Com. That's joinmidi. Com. Well, you're thinking about history, and you're thinking about people who are, again, that need next, the people who are exploring and also pushing frontiers. And I think that does come back to the time is finite.

And you are very clear about that in terms of just like, what am I doing right now? A couple more points, Cara, being the O. G. That you are. You talk about some people who are incredibly impactful to you and helping you to get there. Walt Mossberg being a primary person.

Absolutely. From a career, yeah.

I'd love it if you could just talk about that relationship in terms of what Walt did for you and also what you did for Walt.

Right. I think one of them... He had covered the Defense Department and State Department, I think. State Department for sure, but He traveled with Jim Baker, and he was a big deal at the Journal. He changed everything because he liked technology, right? In doing so made his career massive, right? He had a good career going, and he liked it, but he then indulged himself in the thing he liked, which was technology. And he was the first who did it. And one of the things I liked what he did is he liked things or didn't like them. He never was a fanboy, and he never was a naysayer either. That's very hard to do. You have to get a reputation. When you said, I help people count, I also praise people when they do a good job, too. I'm not always hard.

Not always hard, but always fair. I think you are hard all the time, and you put a My opinion, you put a tremendous amount of scrutiny on everyone equally. And when it doesn't measure up to standards that you have, which we'll talk about those, you are brutal. At getting to the core of why that doesn't measure up.

Well, I don't know if it's brutal or honest. I was just with Sam Alton the other day, and I had been critical about something. He's like, Oh, I thought you liked me. I'm like, I don't really like or dislike you. I think you're better if I tell you what I think, right? Kind of me, and I do like him personally, but it doesn't mean he didn't fuck up, right? That's stuff. I'm not quite as brutal with my kids. I'm usually a little nicer version of that. But I do want them to press themselves, too, and not wallow and stuff. But again, I have no idea where it comes from. I really don't. I just think innately, I'm not a restless person because I think there are restless people in the world, and they don't quite have a rhyme or reason. I think I'm interested in change, and I'm not scared of change. I think the hardest thing to be is a person who's scared of change because change is inevitable, and to resist it is futile, essentially. We're always on our way to something else. We really are in so many ways.

If we talk, go back to Walt just a bit in terms of who he was to you and also how that impacted you. Oh, sorry. I remember, I don't know if I read it or if you talked about it. But just in those early days, it was hard for you. You faced the same obstacles that every woman faces when you're speaking to powerful people. Bossy. And Walt, I remember you talking about one time how on stage, he purposely put you in the middle of whomever you were talking to so that you would need to be recognized. Those small things were enormously impactful.

100 %. Well, again, here's someone who... One of the things that's really amazing is very talented of people are not, some are, I guess, are ungenerous. He's very generous. He knows how much power he had. And instead of keeping it for himself and collecting more, he shared it. And that's a very unusual thing, especially among white men. I'll tell you. They like to hold every single thing. I'll have all the cards, and then I'll have yours, too. One of the things he did is, especially with women, he was very generous and he understood. And putting me between people, we talked about it because people wouldn't talk to me. They They would talk to him, and they would reference him and look at him and he's like, I'm like, What do we do? I said, Well, I jokingly said, Well, put me between you so they'd have to see me. And he was like, Let's do that. It was really interesting, and it worked. They couldn't avoid me. He also would introduce me to people equally. This is my partner, Kara, stuff like that with very powerful people. Now, later, what was interesting is that he knew all the computer people, I knew all the Internet people, and then I would introduce him to people.

He hadn't really covered that much, right? Early, especially Mark Zuckerberg and people like that. He later, of course, interviewed them. But he was just generous. The generosity in abundance was... When you have abundance, if you're not generous, I don't know what to say to you, essentially. And he saw that it also, in being generous, he got stuff, right? He got more. And I think people... He's the original Stone soup guy, right? The one who said, Let's bring in a making soup out of stones. Oh, you want to add a Cara? That's him to me. It's highly unusual among someone of his... He had so much power. It was crazy during those early days.

So, Cara, let's go to, of all the powerful people that you have held accountable, of all the people that you know, what makes for the best CEOs? What are the characteristics? Because you know many good ones, you know many bad ones.

Or good ones that have done bad things and bad ones that have been good things.

No one's perfect.

First of all, I don't give them advice. I'm not their friend, and I don't work for them, and I'm not their advisor or anything like that. I just tell them what I think. That's all. That's essentially it. I don't get anything from it. I'm not paid. Again. But I think one of the qualities, I like persistence. I like change, people that are willing to change and revisit things. Someone who's really interesting, I've been thinking about a lot lately, is Mark Cuban. He was such a jerk when I met him. He was very arrogant, very typical. Then he started to learn and listen. I have to tell you, I just happen to agree with him politically, but he comes to everything he does. He comes to it in a good way. He changes. It's like he reconsiders, and he doesn't also try to please people to do it. He's not a pleaser, which I think you can't be a big leader if you're a pleaser, essentially. But he's also not obstreperous in his own thing. He listens, too. I I think there's some qualities. People who evolve, and that's what an adult does, right? People that evolve are people that I like.

They evolve over time. The people I don't like devolve, and you can see a lot of them that way. Power makes them more insular. Power makes them more certain of themselves. Power makes them feel like everything they say is a pearl of wisdom, and it isn't. They rely on past success classes to say why they're right this time. That's very common.

And you also are so good at pointing out just who people surround themselves with. So when you look to the best characteristics of leaders, who do they surround themselves with?

That's a big thing. Enabling is really... When you get to a certain level of wealth and power, people agree with you, violently. I was with one of them, I'm not going to say who, and they made a joke, and the whole room laughed at it. They said, Oh, Carrie, you're not laughing. I said, I'd laugh if it was funny. I sure would. But it wasn't. I said, They don't think it was funny, but they work for you. They're paid by you. And they're like, Oh, we thought it was funny. I'm like, No, you didn't. It wasn't funny. I'm sorry. And it was like, that was the conversation. And I was literally like, this is what you want out of your life, people that laugh at your dumb jokes, at your bad jokes. I think ultimately a lot of these people know they're not funny. They just get so used to it that it's hard for them to... I don't know. When you pay everybody, I'm very aware of people I pay and what they say or trying to get them to disagree with me. That's a really difficult thing because it's so much easier because very powerful people tend to be very talented.

Many of them do. And so they're often right. They're often they have the good instincts. And when it comes to stuff about myself, I have the good instincts, right? But about you, I don't. I don't know what you should do necessarily. I think often I am about the direction I should take, but it doesn't mean I shouldn't listen, at least, or hear it.

Let's talk about some of those characteristics of learning in terms of just what it takes to be a great leader, to be somebody who's building an important business. And you don't just know these people. You are a leader yourself. You've created strong businesses many times. So what are those characteristics that make the difference?

A lot of everything I do has a through line of For example, my whole thing that I demand is substantive discussions, right? So whatever I do, at some point someone's like, We have to make snackable content. And I was like, I will never fucking make snackable content. I'm not doing... I see what you're talking about, about being entertaining, but I have decided that people really like substantive comp. That is a through line. Accuracy is another through line. I get very upset when it's not accurate, or I'm not accurate, or the people I'm working with aren't accurate, or they take it They don't take it seriously like I do. I think people who are persistent and just a couple of major things that you stick with that don't change, that don't shift over time. I know you'll find this odd, but I think I'm very empathetic with people, even though you don't think I am. I think by telling them the truth, I'm being nicer than other people, shading the truth to them. I feel like if you get... A lot of people say to me, after they get a bad thing that I say, it's like, Thank you.

Nobody else is telling me the truth. I also don't have an agenda. I think really great leaders don't have an agenda. They aren't saying something to get something else. I could do that a lot more and be even more successful, right? I also think it's really kind to be honest with people. I just do. And over the time, I've gotten a little nicer in the honesty, maybe. The other thing that I think is what really taught me is his generosity and mentorship. I that a lot. I think there's a lot of people you'd be surprised that I've helped over time. Operating in abundance when you have a lot is critical. If you operate in scarcity, you're finished. Even if you're really successful, those people who have operated in scarcity and here, I think, will come to bad ends, even if they seem like they're coming to good. Look, Trump is a perfect example. It's Elon Musk. He operates in scarcity. They operate in scarcity. That's how they operate. Someone's going to lose here. I think those who operate in abundance better leaders.

One of the things that you have been, I think, really honing in on is just people who operate with a moral compass or not. And that has become just in the landscape of tech, in the landscape of Titans who are truly shaping this world in ways that we don't fully appreciate, but we know are there. What are the important things for the level of complexity that we really need to be thinking about when it comes to whether it's tech, leadership, running something that has impact?

Well, maybe it's not quite so complex, right? We get overwhelmed by our world right now. It's like you can take every single thing apart, right? Do you remember that scene in Apollo, I guess, the one with Tom Hanks, where they're taking everything apart? Yeah. You can take apart a problem. Let's break it. Get the sock.

Get the duct tape.

Right, exactly. I think because of the amount of information we're getting, we used to be in an information desert. Now we're in an information flood, right? So we don't know which way to look. I think one of the things Steve Jobs used to say is taking complex things and making them simple is a real gift, right? And they can be made simple. What a lot of people do is they complexify simple things, right? And add things on. It's a lot like cooking when they put too many ingredients in or too many spices or something like that. Simplicity is very hard to do correctly, but it can be. I take things, okay, here we are. I do a lot with my kids. If they I have problems, I'm like, let's break it apart. Because then you're able to really, what about this part? What about this? What about this? And at some point you might realize it's impossible, right? And that's also useful information. This is not going to change. We cannot change that. But I'm always looking for a way in. What about this? And that's why I was a good reporter. I was a good reporter because I always found a way in.

What about this? What about this way? What about this way? What about this way?

And scenario planning and thinking it through and thinking about different ways to get into that level of- Or what could be happening.

What's the possibility? Because I think it's solfocleies, and there's nothing new under the sun. There really isn't anything new under the sun. There's new versions of it, but not really. And so I spent a lot of time now reading history a lot more because it's the same problems.

We'll be right back after a quick break. Weight Watchers has continually evolved alongside our understanding of weight health and nutrition. Recognizing that everybody is unique, they have rejected the idea that there might be a one-size-fits-all solution. With decades of experience and ongoing research in science and behavior, Weight Watchers remains a trusted authority, helping millions of members worldwide. It's so important to find a program that truly fits your lifestyle. With over 200 zero-point foods that you don't need to track and measure, they simply guide us towards healthier choices and nutrition. Plus, through Weight Watchers clinic, if eligible, you can now access doctor-prescribed weight loss medications and get support from a dedicated care team. Board-certified doctors focused on weight care, one-on-one consultations with a registered dietitian, medication management, such as navigating medication shortages and more, all through the Weight Watchers app. Weight Watchers fits your needs, whether it's through their Clinically Proven Points program or for those that medically qualify, access to doctor-prescribed weight loss medications and registered dietitians in Weight Watchers clinic. See how Weight Watchers fits you at weightwatchers. Com. That's weightwatchers. Com. Hey, listeners. You probably have some pretty fun memories of going on vacation as a kid.

Maybe it was just a simple camping trip. I'm sure it was memorable. I remember every morning during the summer going to swim team at the local swimming pool. Fun outside, super fun memories. Now, As a mom, I want to share with my kids everything I loved about summertime and nature growing up, the parks, beaches, and camping trips. But with all these heatwaves, wildfires, and storms, un natural extreme weather events caused by fossil fuel pollution, the places we love are being threatened. The Science Moms are a non-partisan group of scientists who are, like many of you, moms. Whether it's understanding the real cause of extreme weather or simply talking about it with your friends and family, the Science Moms want you to know that a better future for our kids is possible. Human-made problems require human-made solutions, and no one is more equipped and motivated to lead the charge than our nation's millions of moms. Science shows us pollution is causing unnatural disasters that are making our world more dangerous. That's why I'm excited about the millions of moms who are taking action to protect all that we love. Join us at sciencemoms. Com. If we think about history and we think about Let's just talk about women in leadership and women who are leading companies of importance, of impact.

And you have done quite a bit over years to call out, whether it's the sexism, whether it is the pushing women down, not letting them be heard. You have to fight against today's just the way it is.

I mean, there is always going to be inherent sexism, period. It just doesn't go. It's like racism and anti-Semitism. It's like mold. It never frigging goes away. It's based in a physical. It's based in the men are stronger, and they are for the most part, not every man, but they are. It's based in physical, and we don't live in a physical world anymore. We really don't. We do to an extent, but We are moving away from a physical world to a digital world. In a digital world, everyone is by nature equal. Why does that persist? That's really interesting to me. What will be important in that future? What what will work. And I think we have to think a lot that why we make judgment, why we live in a past judgment society as we move to the future. That seems a little complex, but I think you get it.

I do. And while things may be trending directionally in the right place, I would just simply say not fast enough. So what do you see in terms of just the opportunity for women today? And just, Cara, you are different. I don't know where it came from, but you've got it, okay? And you've broken through and you had every obstacle and more to deal with. So maybe start with, what about Kara Swisher? Can other women leaders take, learn, hone, and be?

Well, one thing I tend to do when I advise a lot of women, I tell this story a lot where this woman who was very successful came to me and she was leaving. She always had this second, third-level job at companies, and she really wanted to be CEO. I really want to do that. I'm like, Okay, you should do that. One thing she said, she goes, Okay, I've been offered this, this, and this. These are three jobs, right? I was like, . So what do you want to do? She's like, Well, this is interesting. I said, I didn't ask you that question. I'm not asking you what's before you and what you get offered. Like, you're some woman who has three marriage proposals, and this is your only choice, right? She was being acted upon versus acting herself. I said, I asked you what you want. I think a lot of times women don't think about that. What do you want? What would you like to do? I think women just don't think like that. Sometimes, too much, a lot of women do, but many women don't. I use the analogy of a restaurant that if you're in a restaurant and they have chicken, They have beef and they have beef, and they have fish, and you want duck?

Order the fucking duck. And she's like, Well, what if it's not on the menu? I said, They have duck. It's there. I know it's there. Get duck. And if not, leave the restaurant and go to the duck restaurant restaurant. If you want buck and duck, get duck. And she's like, I don't like duck. I said, That's not the point. I said, shrimp, whatever it happens to be. If you don't want what's on the menu, go to another restaurant or tell them, I know you have it back there. Bring me whatever you want. I'm not like this in restaurants. I usually behave in a restaurant. I usually find something I like in a restaurant. But if I don't, I don't eat. I'm like, I don't want to... Like last night, my wife, they were at a taco restaurant, and I was home. I was tired and I was resting. And she's like, Do you want to hear? I'm like, I don't want anything on this menu. And luckily, I live in America now, and I can order whatever I want.

It reminds me of the conversation that you had, the recent conversation with Julia Louis-Dreyfus, where she was talking about women get up. And that just seemed like- She's great.

What a great woman she is.

Well, that was such a great... Of course, I'm a sincere fan of hers, and to hear your conversation was incredible.

Yeah, we had dinner later. We had dinner last week, which was great. And one of the things we talked about, it was the ability to say yes and no. I think it's really hard for women to say no a lot. I say no all the time.

Like, Oh, no, no, I don't want to do that. Jane Fonda's Comment, no, is a complete sentence.

Yeah, that's the name of my next book, actually. But it is. It really is. And it's really hard to get to because you want to be accommodating. Even men do it. But also the ability say yes at the right times, right? I think a lot of people don't think they're capable or they don't think they're up to it. I'll tell you one thing, programming conferences the way I do, white men always say yes. They always get on stage. Actually, the way I got Julie Rees-Dreyfuss is we were at the Webby Awards. We both got one, and she came up to me and she's like, I love Pivot. I said, Well, I love Wises & Me, and we were chitting. I said, Will you come on to do a really... I know you have this new movie that I really hear is great. Tuesday. And she's like, Oh, I'm not smart enough. I go, Stop it. It's the first thing. Oh, my gosh. I was like, Stop it. Immediately stop it. And I said, Now you have to come on because every fucking white man in America always says yes to me. Like, always. There's a very few that don't.

Women, I have a harder time getting women to say yes because I don't know why. Either they've gotten too many requests or they don't feel they're up to it. But I've heard that from a number of incredibly smart women that they don't think they're They're up for the conversation. And I'm like, wow, you're really... The amount of time they spend worrying about their qualities is so much more than men do. It just isn't good.

Cara, I want to ask you two closing questions here in terms of your legacy. What do you want to be known for in those next 100 years long after this time?

Well, it's interesting because I was looking at some of my old interviews. I've done so many, I would suspect, over time. I thought to myself, I'm done. You know what I mean? I've done so many great things, created all these businesses, done really interesting things. There's a body of work that is there that is finished. It's done. And so what it does for me is it really truly frees me now. I can do whatever I want because I feel like I've contributed. But I would say that if I had to put... If I was like, No, I die tomorrow, or whatever it happens to be, is I She lived her life while she was living it, right? Instead of later or no regrets thing. And that's one of the through lines in that interview with Julia DeJeef. She has a body of work that is impeccable now. It could end right now and it be like, What a woman, right? Now she's free to try to do things that she really maybe didn't do before as she was climbing. I thought that made her a really powerful person. I thought about it for myself when I was asking it at the same time.

My question to you is, is your best work still in front of you?

Yes, 100 %. I'm so excited about all these different things that I'm working on. I have a bunch of stuff that I'm... I have this week off for the holiday, and I was like, And then I'm going to think of this, this, and my poor wife is like, Oh, no. I was like, I have ideas. And so now I have all these really interesting ideas that I'm working on. And yeah, I'm going to work until the day I kill over 100 % because I like it. Years ago, I work a lot and I like it, but I also have a lot of I have a very big family, too. Someone was like, Oh, I think there was a quote, like you'll regret on your deathbed, you won't. You'll be like, I don't remember my work. I'm like, I fucking will remember my work. My work is great. I don't think like I don't think like... I didn't waste any time doing the work that I'm doing, and I didn't waste any time doing the stuff with my family. I don't waste time. It's that old quote, I waste time, and now doth time waste me.

I don't waste time. I'm not Richard III. You know what I mean? I think that's Richard III. I think that's Richard III. Anyway, I don't waste time. There you go. There's my legacy.

That is an excellent, excellent legacy, Cara. I just want to say, again, thank you for doing this. Thank you for inspiring others and me. And thank you so much for the work that you do.

Thank you. What a lovely interview. I appreciate it.

You know, Ken, I got to tell you, I was so looking forward to speaking to Kara Swisher. I've been listening to her since ReCode, Decode, Sway, Pivot. I am such a fan, but I worked so hard in this interview to also not come across as such a fan girl. But one of the key things that I heard that was so consistent is how every day she wakes up and she puts her attention and her work towards life is finite, and she's got a limited amount of time, and she is going to do the most that she possibly can with it. Kim, what do you think?

Well, first of all, she seemed to like duck, is what I would say.

I mean, her ability to say, Hey, if it's not on the menu, it's back there somewhere. And it really ran into what she was talking about, Things are not that complex. I mean, I could see her with all her bravado showing up to McDonald's and saying, Give me the duck nuggets. And what's so amazing about her is she really means that. I mean, duck was a metaphor there, but don't settle. If you want it, grab it, get it, get it done. And that was throughout the whole entire interview, and I really liked it. Yeah, she makes no apology for who she is. I mean, she said it. She's like, Look, I'm smart. Look, I am well-educated. Look, I can see around corners. I do my homework. I work harder than anyone else. And there's There's not bravado or boasting that comes with it. It's just factual. She is really clear about who she is. She also said a couple of times, I don't know why I am the way I am, although we can point back to some of the things like her early years losing her father when she was five, which are obviously things she talks about being a lesbian as something that is perhaps some of the reasons why she is the way she is.

But at that same point, that level of confidence, I was trying to probe her as to how can others be the same way? And she didn't even answer the question. She was just like, just do it. I mean, why are we talking about this? It's not a coachable moment. Just do these things. They're important. In listening to Cara, I see a lot of things, and I heard a lot of things that we heard from other people. It's this relentless nature. I've got to get it done. And she wakes up every morning and says, What's in my way and how am I going to conquer it? She mentioned that when women are faced with a number of choices, they overcomplicate it. And rather than weighing all the different choices, women in particular really need to focus on what they want. That's what's not complex. Focus in on what you want, and that is the obvious choice. And she does it naturally. She said she doesn't know why she does it so easily, but she feels that women often struggle with this, and they need to be far more direct, far more clear. That's an important thing for women to do.

In addition to what she is, who she is, how she goes about leading herself, we talked about some of the key qualities that she both admires, as well as who she thinks are the best leaders that are out there. She talks about Walt Mossberg, who is clearly one of the most influential people in her entire life and career. She talks about how he leads from a place of generosity versus some of the worst leaders that she sees out there leading from a place of scarcity. I thought that was a particularly important point. And I found in my career that the people who have and make time for especially aspiring, talented people are really the best leaders. So I completely agree. Those who sit in a corner and say, I'm not going to share, I'm not going to grow my staff, aren't really successful. So it's very powerful. Another leadership point, Ken, that she talked about is the moral compass and how critical it is to have a moral compass, particularly in this world of really impactful things that people are working on, particularly the Titans that she's talking to. Yeah, absolutely. She's really a visionary when she's hanging out with the people she hangs out with, whether it's Musk, whether it's Zuckerberg.

And when she said in a digital world- She likes Mark Cuban. She likes Mark Cuban. She does.

But in a digital world, why is gender going to matter?

And it really is a forward statement. It really blew my mind because really in the future, as we move forward, I think gender walls are going to start to come down even further. And there's an opportunity for women, especially in this digital world, where they're going to be able to go ahead and really be measured by what they deliver and not so much what their appearance is or what preconceptions are. I hope she's right. I mean, Ken, that's a really important point. I think you heard something there that's even bigger than perhaps we discussed in the actual interview. If this can be a time in what is now a digital world to really advance the gender equity, that would be exceptional. I would absolutely love it. I really think she's forward-looking, and I think she's seeing something that probably most of us aren't seeing, and I think it's going to happen. Well, it's better. I certainly know the next time I'm out at a restaurant, no matter what's on the menu, I'm going to be ordering duck. Yeah, and I'll make sure I won't pluck anyone else to add that. Thanks, Ken. Thanks for listening to the Inspiring Women Leadership Lab.

The Inspiring Women Leadership Lab is a production of Lemonada Partners Studio. I'm your host, Laurie McGraw. And I'm contributor, Ken Kaufman. This series is produced by Katherine Girardot and Alex McCohen. Our research assistant is Messia Delgato. Jackie Danziger is our Vice President of Narrative Content. Mixing and Sound Design by Noah Smith. Executive producers are Stephanie Wittels-Wax, Jessica Cordova-Kramer, and me, Lori McGraw. Help others find our show by leaving us a rating and writing a review. You can follow me on Instagram at inspiring-women-pod and Lemonada at Lemonada Media across all social platforms. Follow the Inspiring Women Leadership Lab wherever you get your podcast and listen ad-free on Amazon Music with your prime membership. To learn more about what we talked about today, including additional resources, tips, and guidelines to build your successful company, visit inspiringwomen. Show/leadershiplab. That's inspiringwomen. Show/leadership-leadership. Com./leadership-lab. Thanks so much for listening, and see you next week.