249: Kara Swisher - "The Reporter"

Kara Swisher

Are you conscious of your choices?

"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT

Episode 249: Kara Swisher

Here’s a question. Are you conscious of your choices?

I’m Charles Day. I work with creative and innovative companies. I’m asked to help their leaders discover what they’re capable of and then to maximize their impact.

Welcome to the intersection of strategy and humanity.

This week’s guest is Kara Swisher. She’s the most effective and successful tech journalist of our lifetimes. She’s the host of the podcast ‘On with Kara Swisher’ and the cohost of the Pivot podcast with Scott Galloway. Over the last thirty years, she has interviewed everyone who matters in tech, multiple times. And she’s just written her third book, titled Burn Book: A Tech Love Story.

In a world of white men with giant bank accounts and even bigger egos, how did this 5 feet 2 inch, self-described, liberal lesbian mother of four, end up as the most influential and insightful reporter of the technology age?

As you’ll hear, Kara puts it down to curiosity, confidence, and understanding the choices available to her.

“I do think that I was always willing to, if I didn't like the way something was, to leave. And I think that's another quality that not enough people have, especially people that have choices. I think people don't realize how many choices, we're always defined by choices we don't have. And I'm always defined by choices I do have, and I'm fully aware of my choices.”

Leadership is the art of unlocking the potential of others. But our success at doing that, first depends on our ability to unlock the potential in ourselves.

If you’re listening to this podcast, you have choices. Given its reach around the world, some of you have more than others. But all of us, all of us, have more choices than we think.

Too many times we doubt ourselves, see only the obstacles, respond only to the fear, the one that makes us believe that we don’t have the ability, the experience, the confidence, or the right to choose a different path.

We let others decide our future. We wait for approval, or acceptance, or acknowledgement that we have passed some undefined, moving line test.

But when we choose to take a different path - one that recognizes that life is a journey; that what we do with it depends on the decisions we make, not those that we let others make for us. When we make that choice to take a different path, then we show up differently.

We start to discover that our future is waiting for us to create it. That the choices we make will determine the impact that we make and the one we leave behind.

To be a leader is a choice. To make a difference is a choice. To define our own journey is a choice.

So choose your future. And then create it. In Kara’s words, “be defined by that the choices you have.”

It is the human equivalent of lighting the blue touch paper. And the results will light up the sky.

Here’s Kara Swisher.

Charles (03:15):

Welcome to Fearless. Thank you so much for coming on the show.

Kara Swisher (03:18):

Thank you for having me.

Charles (03:20):

I have to be honest, I hadn't actually thought about reading this book. I'm so glad I read it. It's a great read. It's beautifully written.

Kara Swisher (03:28):

Thank you.

Charles (03:29):

I think it's a really compelling page turner. But the thing that really stood out to me, I think, was how open you were about yourself and your own journey. And I don't think that's easy. I think it's brave to do that, but it adds immensely to the impact of the book.

Kara Swisher (03:43):

Thank you.

Charles (03:44):

I say in the introduction to the podcast, “Welcome to the intersection of strategy and humanity.” And I think the book is a really compelling example of exactly that. Tech companies, by definition are built on creativity and innovation.

Kara Swisher (03:56):

Mmhmm (affirmative).

Charles (03:56):

You emphasize the power of creativity several times in the book. Let me ask you the first question I typically ask most guests. When did creativity first show up in your life? When are you conscious of creativity being a thing in your life?

Kara Swisher (04:08):

A thing in my life, gosh. I think since the beginning, I suspect. You know, I've always been someone who wrote, but even from a young age, and we're thinking about creativity, but I often thought about doing things differently. And I suppose if that's creative, that’s being different. You know, I've been attracted to creative writers or people that are doing unusual entrepreneurship things. Most of the things I've covered and that I've been attracted to have been people like that. And I think that's probably why I was attracted to the tech sector because, you know, at its heart, despite all the damage that I talk about, I do think that there's an element of creativity in all entrepreneurs. And I don't just limit them to tech people. And so it's always been something, you know, I've had businesses myself. I've done all kinds of different things. I wasn't creative in the way we think about it, like theatrical or acting, that kind of thing. But certainly there's lots of ways to be creative. And I think I have been.

Charles (05:06):

Yeah, people get very narrow, don't they in their definition. They think if they're not artistic in some fashion, they're not creative.

Kara Swisher (05:10):

Artistic, right. Which is different. Which is different. I think that entrepreneur, you know, creating a business is creative, right? Creating jobs is creative. Like, you see something that never was before and you say, oh, I think I'll do that. It takes a lot to do that. Because most people go along to get along. You know, it's a cliche, but they really do. And I think not as many people look at something and say, I could do that differently. Or, there's a new way of doing this, or, what about…. They see things differently. And it could be, you know, I was an a… I wanted to be an architect, but I wasn't talented enough. I knew that. I was aware, but I knew what was good, if that makes sense.

Charles (05:46):

Yeah.

Kara Swisher (05:47):

And so, you know, I've always been attracted to that. I've just found it through writing and journalism versus an architect or an artistic person.

Charles (05:55):

I mean, I think to your point, entrepreneurialism is one of the most powerful pieces of self-expression, right? I mean, it's a profound personal journey. I mean, you discover so much about yourself. Why did you think you weren't good enough as an architect? What was your reference point?

Kara Swisher (06:09):

Oh, everything I designed was… you know, I took it in high school, and luckily my high school had a drawing…. And I liked, you know, I really like the anal retentive elements of it. The T square. I had a T square, and I liked the drawing and the preciseness. I probably would've been a good baker if I was a cook, versus a, you know, a more creative chef. I follow recipes, that kind of thing. But I was, I just, everything I designed was ugly. I don't know what else to say. It just wasn't interesting. But I could recognize interesting, right? I could say, oh, I like that, or something like that. But I could never make it like that's, and so when you just, everything you design is ugly, that's really not a good job for you. And it was obvi— it was clearly ugly. And many people told me it was ugly. And I was aware of that. I was not— I was like, really? I was like, hmm, yeah, you're absolutely correct. So ugliness was my problem.

Charles (07:00):

That's a bad trait.

Kara Swisher (07:02):

And I wasn't even form follows function either. It was like, it's just… and there's plenty of those ugly buildings, but they’re, you know, masterpieces. There's nothing masterpiece about it. But then, when it came to journalism, I was very good. Like, compared to other people, I would try different things. And it manifested it really well when I… even when I was in college, I was writing more voice-y columns, which weren't being done at the time. I was, news columns I was doing, when I started All Things D, nobody had done that. And now everybody does it. But podcasting, I did 10 years ago, before other people did. That to me was my version of creativity.

Charles (07:38):

Where do you think that sense of disruption came from? That sort of innate desire to disrupt?

Kara Swisher (07:43):

I don't know if I wanted to disrupt as much as when I see something, I'm like, why are we doing it that way precisely?

Charles (07:49):

Mmhmm (affirmative).

Kara Swisher (07:50):

Just like when I was doing a silly thing, like, I would have to do earnings at the Wall Street Journal. That was one of your jobs every week. Someone had to be in charge of earnings, and you just write them up. And I was always like, why are we writing them up when a computer can? Like, I don't get it. I don't understand why I'm wasting my minutes on the planet on something that could be easily automated, essentially. Same thing with the way we were delivering information to people. I was like, why do we do it this way? Like, why can't we do it this way? I think people would like this more.

You know, I don't think I was trying to disrupt, I just thought there are better ways, or different ways of doing things and that people were interested in. And, you know, pretty much, I was right about a lot of things and stuff. The way we do substacks or a lot of websites today, has a direct line to the stuff we were doing at All Things D a long time ago. And we were willing to try things. Like, one time we did shadow puppets to tell the Rupert Murdoch story once. We just thought that was, it didn't, it wasn't going to be forever, but we just decided to challenge ourselves in new ways of storytelling. And some of them worked and we kept with, and others were just a flash in the pan. It was okay. And we really did try to push our employees to be that way. That was something we really did.

Charles (09:02):

As I read the book, I would define you as fearless. Do you see yourself that way?

Kara Swisher (09:06):

I guess? I don't know. I'm not sure I like that term. I don't, what does that mean? I'm scared of scary things. I don't know if it's fearless, because then it's like, it's based in fear, right? I just think I'm… I like doing different things. I like to think of things in different ways. And, you know, you can look at a square, say, you have a cube. I look at it from a different side. That's all. And I think most people look at them dead on. I don't think that's fearless. I just think I'm just curious, would be a better way to do it. I'm curious. And I think when you say fearless, it means everybody else is fearful? I don't know if that's the case. I just think they sort of take things at face value, and aren't as curious as I am. I would definitely say I'm curious.

Charles (09:44):

Curious with the ability to act. I mean, that's a rarer combination, right?

Kara Swisher (09:47):

Yes, it is. Yeah, I don't know quite why that is. You know, I don't know what we get drummed into us at a young age that we're supposed to get in line. I mean, I'm not a very good get in line person. That's true. That's true. And I like lines, some lines I like, right? It's not like, you know, when you're waiting for a train and someone cuts, I'm always irritated by those people, because of the sense of superiority. It's always the same man. But I don't like staying in lines for the sake of staying in lines. Like, because that's, you know, it's not your turn yet or whatever. Even if, even though I believe in that people need to be mentored and come along, you know, and you can't jump a line if you're not prepared. I mean, a work line, it's a metaphorical work line. But I do think that I was always willing to, if I didn't like the way something was, to leave. And I think that's another quality that not enough people have, especially people that have choices. And I think people don't realize how many choices, we're always defined by choices we don't have. And I'm always defined by choices I do have, and I'm fully aware of my choices.

Charles (10:49):

I know that the death of your father was a cataclysmic event for you. To what extent do you think that that independent streak, that willingness to act out of curiosity was formed by that?

Kara Swisher (10:59):

A lot. A lot. I think from a young age, I was five and he died of a cerebral hemorrhage. He was just starting his life. He had just gotten out of the Navy and had gotten a good paying job. He was a doctor, and he just bought his first house, the whole thing. And then he died. Like, I think that, what kind of message would that send? Oh no, you don't have any certainty of life, right? He thought he was starting off on his greatest adventure after, you know, getting there, getting ready to get there. And I think that was very formative. I was like, I don't have that kind of time. Look at what happened to my dad. I think it just, that doesn't happen— You know, some people living in places do get that every day. That life is very precious.

And so I had a sense of time slipping away, you know? And all those quotes always stuck with me. Like, I waste time. ‘I waste time. And now death time, waste me.’ Right? I really, you know, that was from, I think Richard III. I was very sensitive to time, like, aware of the time I had on the planet. And I don't think other people are, especially young people. And I was from, like, I don't have time for this, and more and more, I really don't. I was working for someone and I quit. And they're like, why? And I said, I don't want to talk to you anymore (laughs). I just was like, I just don't have time. Like, you're taking up minutes and I don't wanna give you any more. And I know it's, I said, I don't mean to be rude, but I just look, I got limited and you've taken up far too many of my minutes, kind of thing.

Charles (12:20):

Yeah. Too many people I think are not conscious actually of the passage of time and how much is slipping away.

Kara Swisher (12:25):

Yeah, I'm very conscious of time passing. And I think a lot of people waste time. They do, on all kinds of silliness. Especially, you know, some things are neurotic, some things are, just, they waste time. They think they have all the time in the world, and they absolutely don't. They absolutely don't.

Charles (12:43):

I want to come back to time in a bit, but I want to just circle back to creativity for a second. You talk a lot about the internet company failures, some of them anyway coming about because they weren't creative enough. I think you said, ‘I've always maintained the people who ultimately succeed, are the creative ones. Creativity is what kept Apple in the game against Microsoft early on.’

Kara Swisher (12:59):

Mmhmm (affirmative).

Charles (13:00):

As you've observed it, what do you think those companies do to unlock the power of creativity and creative thinking that their competitors don't?

Kara Swisher (13:06):

Well, it's hard when you get bigger, right? Because every move is so scrutinized and so expensive. I think it's a lot easier when you're smaller to do that. But when you're smaller, there's a risk that you'll run out of money, right? So that's—on that, that's the pressure on that side. I think what I've noticed is they're willing to take risks with whatever they're doing, and they have a point of view. And sometimes they're wrong. Sometimes their point of view is wrong. Like, if you remember, Apple had its Ping service and it was the only, it was a social media thing they did. It was built around music. And it really didn't work because that wasn't their area of expertise, right? They weren't particularly good at it. And they were chasing it because of Facebook, and then Google had gone into Google Plus, another chasing Facebook, chasing MySpace.

And that was the one time they didn't, they didn't, like, they followed someone, which they never did. And I think really creative people, they'll look out on the landscape and they'll say, oh, that's interesting. That's interesting. That's int— But then they'll find their own inspirations places. Or we want to go in this direction. We're interested in this. And they'll stick to it. That's another thing is sticking to a vision, with flexibility, because you have to change when you have a vision. But I just think they find the, especially, it's very hard for these big companies to do it. And you could see some of them stumbling because they're not able to be as creative. But it always seems to me, those that follow and copy tend not to do as well. Not always, Facebook's very good at following and copying. And Microsoft certainly was. But I think most really impactful companies just decide, this is the direction we're going, and that's what we're doing. Like, to make the iPhone was quite leap, for example — most important product, I think, in tech history at this moment at least.

Charles (14:50):

Am I remembering the story right in the book that you said, Steve Jobs asked you what you thought of Ping and you said, it's terrible, it's not gonna work, and it sucks?

Kara Swisher (14:56):

And he knew it. He knew it. Because he never could, how could they innovate in that area, right? That wasn't— their area was hardware and they had moved into software, but social media? That wasn't their, it wasn't even close to anything they'd ever done. Now I believe in trying new things, right? Try new things. But they were following so clearly and just didn't get it. It was sort of like someone from another planet trying to speak English. They just couldn't do it. And they shouldn't have, it wasn't their… if they had a fresh new take on it, perhaps. But they didn't, they didn't have a fresh new take. And so he even knew, they got rid of it so fast. I mean, I'm sure he was embarrassed by it. Because no matter what they did, they weren't the people to do it.

You know, it's great if you're a chef and you're cooking French and then you try Chinese, but maybe not. Like, you could maybe move over into that area, but it takes a long time and a lot of expertise. But they were French chefs and that's what they made. And so, they could do variations on that and could try different things, but it often doesn't work, I think, for a lot of tech companies. And they particularly weren't very big followers of anybody. They followed their own tune as a company, for the most part. Not always, but for the most part.

Charles (16:08):

And you're right, those of us that were heavy users of Apple products, when that came out, it didn't feel right, it didn't feel connected and joined up.

Kara Swisher (16:14):

It just didn't make any sense. And it wasn't integrated and it was too early, and, you know, Facebook was better, or Twitter was better. It just, other things were better. And usually what they tended to do, and they do do this strongly, is they often come in second.

Charles (16:27):

Mmhmm (affirmative).

Kara Swisher (16:27):

You know, for example, the AirPods, you know, they were around, versions of those were around from other companies before Apple moved in, or the Watch. They came in kind of third or fourth, but they did it right, right? They did it their way in the way they wanted to do it. And so I always think you have to be true to yourself. Like, really understand your strength and weaknesses. And many people don't. They don't assess, not just their weaknesses. Because everyone always assesses their weaknesses. Always. This is what I do wrong. This is why I'm ugly. This is why my face not, they never assess their strengths. You never assess their strengths. And I tend to assess my strengths quite a bit.

Charles (17:03):

That's a fascinating insight. because I see that in my work all the time. I talk about that a lot as a leadership advisor and coach. You see people emphasizing their weaknesses and worrying about shoring their weak points. I think when you're naturally talented at something, we think everybody can do that. And so we under, we undervalue it.

Kara Swisher (17:17):

You have to know, you're aware. I always say, you know, there's an expression I think among sort of like lady go groups, sort of, like, know your value. And I'm like, yeah, not such a bad idea. You know, you do have to know your value, of what you are and who you are. And I think people don't, and you have to honestly assess it. You have to honestly assess your value. And that's really hard. And I think people have a hard time doing that, especially because they don't want to compliment themselves either.

Charles (12:45):

Yes.

Kara Swisher (12:46):

And that was, that's something I'm really good at. I'm like, I'm good at this, I'm bad at this, I'm good at this, I'm bad at this. And sometimes it's interesting because I get a lot of, I hate to say this, but it is men that do it. They're like, oh, you shouldn't be so confident. I'm like, why? I'm not saying something that's untrue. It's just interesting to watch, actually.

Charles (18:04):

Well, and it speaks to their insecurity, doesn't it?

Kara Swisher (18:06):

Well, it's just like, you know, people are not comfortable with women being highly confident. They seem either bossy or, you know, something’s like, why are you, again, men? I have sons. I have three sons and one daughter, and my sons are very confident when they shouldn't be. Sometimes (laughs), I'm always riveted to it. One time my son wrote a piece and he goes, it's great, right? And I'm like, actually, no, no, no. And he was like, you're kidding, I'm fantastic. I'm like, yeah, and again, I'm going to give you a no on that. And what was so funny is the confidence continued despite the fact that it was like inaccurate about goodness. And I said, here's how you could make it better. And he certainly did. He did improve it. But I was just riveted, riveted, riveted to, to it. They just make me laugh. My sons make me laugh all the time. But they're frequently wrong, but never in doubt. And that's, I think that's an asset to them.

Charles (19:02):

As you look at the leaders that you've reported on, I'm curious whether Steve Jobs had that quality, where he had that kind of level of certainty, but was wrong a lot. How did Steve show up to you?

Kara Swisher (19:12):

Oh, actually, no, he was not, he was not, I mean he made decisions. The way he did it was, I'm going to do this, you can like it or not, he never said, you have to do it. Like, when he took, he took one of the dongles off the side, and I forget which, you know, when you stuck a little whatever it was to save stuff and he didn't like it, and he took it off and everyone lost their minds. And he said, I don't really care. It's what I want. Like, I get it, but I'm going to do it. So is that being confident or what? He just didn't want to do it. And he understood the price of it, for sure. It's just that he didn't care. He didn't care. He didn't care. He really didn't.

Charles (19:53):

What do you think the world would be like if he had lived?

Kara Swisher (19:56):

Oh, I don't know. I don't know. I just, I think, you know, dying was kind of part of the legacy, right? You know what I mean? Like, one of these great geniuses dying. I don't know. I, that would, I think it would be better. I think things would be better. Although I think Tim Cook's done a very good job continuing that legacy and actually also making it more valuable, for sure.

Charles (20:19):

Mmhmm (affirmative).

Kara Swisher (20:20):

That company is 10 times more valuable, right? So I do think, he was right in his choice of Tim Cook, even though everybody sort of trashed it. They have two businesses that are huge. AirPods and the Watch are pretty good. They're an enormous software business now. That doesn't, you know, it may not seem creative and wow, but boy, are they wow businesses and the music business, the software business, the services business. This guy's pretty good at creating new products that people like.

Charles (20:48):

You described the worst of the leaders that you highlighted in the book as, “unaccountable people making decisions for the rest of us and not paying the price of damage.” Do you think, are we suffering from a failure of imagination of how bad that damage could be?

Kara Swisher (21:02):

No, I think we're aware of it. I mean, people are aware of it. It's just that we rely on these products so much for our daily life. It's hard to get rid of them, you know, if it was a cigarette, which it is in some cases—

Charles (21:14):

Mmhmm (affirmative).

Kara Swisher (21:14):

We would put labels on it, and we would sue them. Or we would do something so that they would not shove it full of crap. But in this case, we need it every day. And that's a problem. Like, you can't, you can't leave them and you can't keep them, if that makes, you know what I mean? Like, you can't, it's really damaging to you. And so I think that's hard. I think that's super hard. You know, I think we are aware of the damage. I just don't think we are, because we’re so… it's so necessary and so also addictive, it's really hard to break away. You just can't quit them, right? You can't quit them.

Charles (21:52):

You've made the point in a couple of things I've heard you talking about in the last couple of weeks that government has just done nothing.

Kara Swisher (21:57):

Nothing. Nothing.

Charles (21:58):

Do you see any—

Kara Swisher (21:59):

Actually, today, Margrethe Vestager fined Apple $2 billion. So that's something. So, that's something.

Charles (22:07):

Do you see that fundamentally changing? Do you see us being protected by government going forward in any way?

Kara Swisher (22:12):

I don't know. I've been waiting forever, right?

Charles (22:15):

Yeah.

Kara Swisher (22:15):

I've been waiting forever. And so I would assume so, but so far, no good, right? They haven't done anything. And so, you kind of have to wonder what's going on. Like, here we have the most, as I've said dozens of times and dozens of times, these are the most powerful businesses on the planet from every, every perspective. And we're still trying to figure out to regulate them? And they've gotten so much protection.

Charles (22:44):

Yeah, it's incredible, isn't it, how much freedom they have. Do you think that they're an existential threat to democracy?

Kara Swisher (22:50):

Yes. I mean, among the things, there's so many. I mean, I put Donald Trump at the top of that list, but he's used these tools. You know, yes. I think, I don't know what we can do about that part, but we certainly can do things around misinformation, propaganda, privacy, the ability to incite people. You know, there's all kinds of things. I just don't think we want to admit to us something that we need every day is so dangerous for so many of us.

You can also, like I said, you know, I think the key quote in the book is the Paul Virilio quote, which is, “When you invent the ship, you invent the shipwreck.”

Charles (23:26):

Mmhmm (affirmative).

Kara Swisher (23:28):

And I think what drives me crazy is like, I still like the ship. I just want to have some, you know, lighthouses would be nice. Or when you invent the plane, you invent the plane crash. Well, great. But maybe some radar, right? You know what I mean? It's sort of like, you don't have to totally ignore the things you can do to make it better.

Charles (23:51):

Yeah, when you invent electricity, you invent electrocution. That's why we put, that's why we put the lines 40 feet up in the air, right?

Kara Swisher (23:57):

That's correct. That's correct. I mean, honestly. That's what it's like to me. It's like, we all love electricity, we love a light, you know, but do we really want to have the lines down in the ground so our children can grab them? It just makes no sense whatsoever to me. And the fact that people get all like, well, it's hindering innovation. I'm like, it didn't hinder innovation of anything. It just doesn't hinder innovation. It's just, it's just, it doesn't, it doesn't.

Charles (24:26):

You reserved special praise for Dave Goldberg, Sheryl Sandberg's husband, CEO of Survey Monkey. He died tragically young.

Kara Swisher (24:32):

He did.

Charles (24:33):

And you said, “His death diminishes us all.” And then a little later you added, “Dave was exactly the kind of leader we need more of here.” What are the leadership characteristics that he exhibited?

Kara Swisher (24:42):

Again, he wasn't perfect. And everyone, you know, when they die, they get a little more, like, perfect, right? No matter how you do it. But I think he had a real, he… look, he stood out because he wasn't like, “Everything's great, Kara.” He was a booster of tech, no question. He was a booster of his wife, you know what I mean, with Sheryl Sandberg. And, but he was like, oh, yeah, that's a problem. You did not hear that. And that's why he was special. He also had a lot of empathy for people. And I think, my hopes would be that he would have been, you know, a very strong impact on both Mark and Sheryl in terms of, we really need to address this, right? That, you know, one of the, you needed those people in the room with the kind of strength those people had, which you didn't nearly have enough of. People listened to them. And I think too many of the people around the stronger people have become enablers or else they're getting money from it. And so, that was a problem.

Charles (25:38):

I want to talk about the humanity part of the strategy meets humanity tension point that I talk about in this podcast. Steve Jobs’ final words were, “Oh wow. Oh wow. Oh wow.” You described his passing and then you described those words as wondrous. Maybe this is a strange question, but I'm curious of your answer. What do you imagine that he understood in that moment?

Kara Swisher (26:00):

I don't know. I wasn't there. I don't, no, I just thought that was a beautiful piece of writing. I just reread it. It's by his sister, who he met later in his life. Mona Simpson, who they met after they realized that he was the one that their parents put up for adoption. I just think it was, I don't know what he saw, something cool, I guess, or maybe a light, I don't know. I don't know. I'm not dead. I don't know.

Charles (26:22):

Do you ever think of, do you ever think about that?

Kara Swisher (26:24):

Yeah. I thought that was such a beautiful piece of writing about his last moments and about him. I thought that really, obviously it’s from a sister who loved him, and it's a eulogy, so they're not going to say, “What an asshole.” But I did think it just was kind of cool. It was like, well, wonder what he saw? You know, he was always sort of set like, “What? You're not going to believe this,” you know, which I liked about him. He was enthusiastic about his product. People used to make fun of it. They called it the reality distortion field. Maybe he was doing that. It's like, “You're not going to believe it when you die. Wait ‘til you get here.” I don't know. I don't know what he saw. What do you think?

Charles (26:57):

Well, it was in—

Kara Swisher (26:57):

Apparently you see a light. That’s what I understand. All your loved ones. Who knows what he saw? I don't know.

Charles (27:04):

Well, I think, at least my experience is that there's a lot of truth to that. I was with my mother in the days before she died last year, and it was pretty obvious that she was spending time with her mother and other figures from her past, based on the way she was describing it.

Kara Swisher (27:14):

—memory, or maybe it's your memory. Maybe they are there. Maybe it's your own memory, recreating memories. I don't, I don't know. You know, one time years ago, this is completely off-kilter here, but, I went to, there's a place called Lily Dale up in upstate New York.

Charles (27:28):

Oh, yes.

Kara Swisher (27:29):

It's the mediums, they're a town of mediums. Which, by the way, mediums don't like psychics. The one medium said psychics are a bunch of liars, or psychics and astrologers. And I was like, you're talking to the dead, but okay, sure. Whatever. Like, they have wars amongst each other, the mediums, the psychics, and the astrologers. And, I was in one of these glens and they, you know, someone's in the front saying, you know, is anyone here has someone died of a heart condition? Which of course is everybody, right?

Like, everyone’s hands up. And they, you know, they ask you a question and they find someone that I think a little bit, it's a little bit of a scam, but it's fine. I think it's totally harmless. And, they were like, so-and-so says, you know, your keys are in this, wherever the hell the keys are. And I put my hand up. I'm like, why are the dead concerned with keys? Like, what's over there? Tell us what's going on over there. Forget the keys in this life, or forget the money you left in the drawer. Come on, you're over there. I want some information about over there. I don't, they're always concerned with this life.

Charles (28:28):

Have you ever met anybody in that area that you thought they bring something to the table that's interesting?

Kara Swisher (28:34):

Oh, mediums? Yeah, I did. Someone said something…. I'm a skeptic, as you might imagine, of most of those things. And I went, I did one. I'm like, why not? Like, what the heck? And someone did say something to me, came up with the name of my grandmother, who you would not, it's a very, I'm not even going tosay what it is, but it was a very unusual name. And also a pet, a name of a pet, and said, oh, there's a dog down here. And they were both unusual names, and either they could read my mind or I don't know what, it was a very f*cking good guess. And I felt like, I don't know what it was. I don't know what it was. It was weird. It was just the one time. And I thought, okay, you're either really good or you're really good.

Like, one or the other, either as a faker or a real thing. But I don't know. I think people give off energy. I don't, I don't disbelieve that. I think, you know, you can go to places. I mean, I sound like a California person, but you can go to places and feel things, right? Whenever I go up to Mount Shasta in California, there's something happening in the ground. It's magnetic or something. You can feel it, you can feel certain geographies, you feel it. I think it's mag— people tell me it's magnetic fields and things like that, which makes sense to me. But there is an energy in the universe that I think we ignore because everything's so noisy.

Charles (29:54):

Yeah. Somebody introduced me to ley lines. Have you heard of ley lines?

Kara Swisher (29:57):

No. What's that?

Charles (29:58):

They are basically lines of energy and they go back to pre-civilization. Some people say that they were trade routes. Other people say they were energy roots. And they converge in places that you might, you might expect them to converge. So, I'll send, I'll send you a link.

Kara Swisher (30:12):

Thank you. Ley lines. You know, I'm from San Francisco, so some of it, I'm like, mmhmm (affirmative), mhmm mhmm (negative) mhmm mhmm (negative). And some of it, I'm like, sure. I mean, I don't, I'm, you know, someone, the other day, because a lot of people are doing more, there's a lot of prayer books on the bestseller list and things like that. And I respect people are religious. Most of them. Not the terrible ones. They can go f*ck themselves. The ones who want to take away gay rights and things like that. But one of the things that I am interested in is, someone asked me if I was religious, and I said, not traditionally, and they're like, oh, so you're an atheist? And I said, no, I don't know. I don't know. I think as a reporter you kind of have to be like that. Not certain.

And I'm like, I'm agnostic, which means, I don't know. I don't know. I haven't, I don't feel it myself, but I certainly see it in people. So, I try to remain as a reporter, like, not, you know, there's an expression I use in the book, “frequently wrong, but never in doubt.” I use it with a lot of people, like I just said about my sons. And I think it's true. You have to constantly be like, well, interest— that goes back to creativity. You've got to be open to things that you don't know about or open to things that might be different. Because a lot of these companies, I was talking to Scott Galloway today, you know, at the time, you just didn't know what was going to work. You didn't know it was going to catch on. And to say we did, you can't, you just, like, people thought Amazon was Amazon dot bomb. Well, they were wrong. They just didn't, you know, think it through correctly. Or maybe they just were just flat out wrong. So I'd like to keep an open mind about most things.

Charles (31:43):

You have dogs, you have dogs, right?

Kara Swisher (31:45):

I did. My dogs have retired up to the country. But yes, I have dogs.

Charles (31:49):

I think it's interesting being around dogs when they die, because the effort, the effortlessness of that suggests to me that they have a different view of death.

Kara Swisher (31:59):

I remember when one of my dogs died. I remember watching, he waited until he could get home to die.

Charles (32:05):

Yeah.

Kara Swisher (32:06):

It was really interesting. And then, I could see the light go out in his eye. I've never seen someone die like that.

Charles (32:14):

Same, same.

Kara Swisher (32:16):

And the light was like a TV. Remember the old TVs when they, people who aren't old enough, don't remember, when you turned off TVs, the little thing would go to a different dot, to a tiny dot, and then go off. And that's what happened to his eye. And then once he was dead, he was, that was not the dog. It was weird. I didn't feel anything for the body. It was really interesting.

Charles (32:37):

It is interesting. I've had four of them die on my lap, you know, when the time came and the vet comes to the house and they passed, and it's the most effortless sigh. And then you feel them get lighter. And then to your point, they just don't look like the dog anymore.

Kara Swisher (32:49):

No, they were not. I have not been, I have removed myself from people that die. I have not gotten into that room. I don't, I feel very uncomfortable. I never go to wakes, for example. I don't know if you've ever been… Italians like to have wakes. And I do not like to go to wakes because I don't want to see dead people. I don't see dead people.

Charles (33:09):

You mentioned your grandmother, and you say she was the most important person in your life and that she used to say to you all the time, sort of going back to your point from earlier, the graveyards are full of busy people. In response to that, you wrote, “Yes, the graveyards are full of people who did amazing things. And in the end, that's where we all end up. It meant that I did not have any time to waste.” And you talked earlier today about being in a hurry. Are you afraid that there's something you won't get done?

Kara Swisher (33:35):

No, but I save a lot of, you know, there's a, there's an app called, here, I'll just read it. It's an app I look at all the time called, We Croak, which is all quotes, about death, essentially. And it says, this one, it just popped up, said, “In Bhutan they say contemplating death five times a day brings happiness,” which I think it does. I do think about it. I'm like, I really have to think about the time you have. And so I think contemplating death makes you live better, you know. There's so many smart people. It makes you live better. It doesn't make you obsess on death, that's for sure. Not for me at least.

Charles (34:13):

Yeah, you said you don't want to die before you've lived. Have you lived?

Kara Swisher (34:16):

Yes. I feel like, you know, honestly, God, watch, I’ll probably die tomorrow. You know, I was, I was, someone, in doing this book, you really do reflect on your life, right? You do in a lot of ways. And there's a, what's interesting to me about this book, speaking of creativity, is the stuff I've forgotten, like, that didn't make it into the book, and they were, took enormous amounts of my time, like, covering Yahoo or covering a bunch of companies that I don't, didn't put in the book. I just wasn't that interested anymore, right? It didn't leap into my memory in, in the same dramatic way. So what I remembered was what was important. And so, but one thing that was clear as I, as people bring things up and I forgot, I've done thousands of interviews, right?

I just don't remember them all. Now people come up to me like, I love that interview you did with blah. I love the interview you did with blah. And after a while I was like, you know, I did the Gates Jobs interview, all the Mark Zuckerberg ones, all the Elon ones, all the Steve Jobs ones. I did one of Monica Lewinsky, I think was the best interview she's done, for sure. And she says so. I think I have contributed to the body of knowledge very nicely. I think I've done enough. Like, if I didn't do another one, I would be good with it. I'd feel good about my contribution. So yeah, I could die anytime now. I'm good.

Charles (35:34):

That's quite a legacy.

Kara Swisher (35:35):

Except, I have four kids. I have four kids. I don't want to die. And that's what's, that's what's important to me. You know, even though everyone's sort of like thinking I'm a super ambitious person, which I am. I don't hide from it. I also am someone who's really very much, much more oriented towards my family than people realize. One of the strengths I've had, and it happened early in my career, where, you know, someone's like, someone's not going to like you for that. I'm like, I don't care. My kids like me. That's all I care about. If you like me or not really matters to me very little. And I think that has carried me because I think a lot about my family. I think it, speaking of creative, I think it's the most creative thing I've done, is have kids.

Charles (36:18):

Is there one thing you'd want people to take away from this book?

Kara Swisher (36:22):

Well, there's a couple of things. Different people have different takeaways. If you just want a history of the internet, this is a good one. Here you go. This will give you a very good sense of what happened. And you know, a lot of people are like, oh, I, this sort of, I remember, right, this is what happened. And I think if I wrote it, did not write it for techies. I wrote it for regular people. And I don't think techies aren't regular people, but you know what I mean?

Charles (36:43):

Mmhmm (affirmative).

Kara Swisher (36:43):

I didn't write it for them. They already lived it. So I think if you were coming away for a history, you do that. If you're, if you're a woman, you might think, wow, this kick ass lady did what she wanted to do. Maybe I should think about it.

So for a lot of women, it might be inspiring in some ways, I think. For people who are interested in changing their careers, you know, or being more comfortable changing their careers, I think a lot of people will like that, because I'm, like, always leaving jobs. I'm always trying new things. So I think it’s… it’s not inspirational in that way, but it's a good little map to do that. And then if you're interested in the dangers that technology has, especially as we're entering into this new era of generative AI, I think I have a map for what happened. So maybe we should think about it as we move forward. And I think that's a really good thing, too. And so these are all very different things to look at, really. And I think all of them are different. Or you can come away with all of them, or you could just laugh. Because there's a lot of funny parts of this book, I’ll be honest with you.

Charles (37:44):

There are a lot of funny parts.

Kara Swisher (37:44):

Aren't they? They're funny. It's funny.

Charles (37:46):

It is funny.

Kara Swisher (37:47):

People are surprised. I'm like, why? I am funny.

Charles (37:51):

You are, for sure. It's a really good study of leadership, I think, as well. But I think most of all, it feels to me like it's a very, very powerful reflection on living a life with intention. I think that that is the through line that keeps coming back to me as I read the book.

Kara Swisher (38:06):

Yeah. I think different people are going to take away different things from this book. I know what I meant to say, but I certainly don't want to tell people what to think about it. I think they should take away what they want. I had an 8-year-old come up to me who's a big fan of me, which was kind of fascinating. One of my youngest fans. She had her dad read her parts and I was like, okay, little advanced for you, but all right, we'll go for it. And she was, she was like, well, you know what I really liked, I want to do what I want to do, and you do what you want to do. And I said, yep. And I said, you should keep doing that. And she goes, I'm going to keep doing that. And I'm like, mission accomplished. I got one girl to be confident in and of herself, you know? And I think that was good. I felt good on that one. That was a win.

Charles (38:49):

I suspect quite a few more than one.

Kara Swisher (38:50):

(Laughs) Yes, but men do, too. Let me just say, men should read it, too. It’s an ongoing, I wrote this for my sons as much as my daughter in a lot of ways, because I want them to be good citizens of the planet.

Charles (39:04):

I would absolutely endorse that. I think this is a lesson for anybody, regardless of gender. And I also want to say, not gratuitously, I hope— I'm not sure if you hadn't spent your time on the career that you've had, who else would've done this? And so I don't think we'd be very wise at all about what these companies were doing. I really want to thank you for joining me today. And I hope the book is a huge success. It really is a great read.

Kara Swisher (39:28):

Thank you so much. I appreciate it.

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