Meet The Journalist Every Tech Billionaire is Afraid Of (Ft. Kara Swisher)

0:00Kara Swisher decided to leave the Washington Post to cover the internet full time. That decision has made her one of the most respected and feared journalists on the beat, holding those in the tech world accountable. Feel like you're violating people's privacy? One of the most outspoken critics of the tech industry and the billionaire moguls who are cozying up to the White House right now. I don't know a better must-translator. As he got richer and richer, he got crazier and crazier. Very successful podcast, Recode, Decode. Author of Burn Book, Kara Swisher. I'm Kara Swisher, and welcome to The Burnouts.

0:30When you first started out your career, you were a student at Georgetown and you were correcting the paper, right? You were finding spellcheck errors. What was happening was I was writing columns as a freshman. When I got there, I didn't want to stay at Georgetown because it was very anti-gay. It was anti-women. And it was just a bad campus fit for me. I was going to transfer. So someone came in and said, why don't you write for the student newspaper? You seem very funny. And so I started to write a column and it did really well right away. And so one of the things that drove me crazy was how sloppy they were in terms of how they edited and things like that.

1:04And so I just was always like, this isn't right. This isn't right. And the job you're talking about was at the Washington Post. So that was later. I didn't like working for the student newspaper and started to do internships around Washington, which is super easy to do. And I suggest everybody does them, you know, in college. Just work, work in the workplace. Favorite internship? it? Probably the first one I did for a magazine, for a magazine editor. And just whatever you do that's kind of scut work, you know, kind of thing. And I recommend it to my kids and everything else where you just get to do everything.

1:36Friend of mine is a son is a is a page at the Senate. And I was like, what are you doing? It's like getting water for senators. I'm like, good. My dad was a page in Olympia. Yeah, he was for years. Yeah. Oh, I had no idea. He talks about it way too much. Actually, it's a great job because you get to see how things work. And so I called the Washington Post because I wrote a story in the student newspaper that one of their reporters covered. And the reporter's story was full of errors and it drove me crazy. And so I called them. It was just a shitty little story. Like they send the worst people to cover things at Georgetown.

2:09And so I got in touch with the editor there and he had me in and said, come down on the bus. And so I took the bus down from the gates of Georgetown. And I went up and told him he sucked and he hired me. He hired me as not an intern. I was paid. I was a copy aide. How much did they pay you? Oh, God, nothing. My first real job was$14 ,000 a year. So not much, you know, just an hourly wage. Probably I would bet it was somewhere under$10 an hour. But I delivered mail. I worked at night. They called it night news aid. I did everything. I did everything. And while I was there, I started to see the opportunities of writing.

2:44And I got whatever writing I could get, even the lowest level writing, so that editors would get to know me and I'd say yes. And what happens is a lot of people at work who work there get themselves lazy like this reporter did. And so I just volunteered for everything, like whatever it was, covering things on the mall during the summer for the Smithsonian Folk Festival. I'll go. I'll go. It was really hot. And so I did every job that I could and met everybody that I could and then eventually worked my way up there. I went to Columbia Journalism School in the interim, had another job. But I just did whatever it took, essentially, and didn't think anything was too good for me.

3:21I think a lot of people feel that. I love this sense of, yeah, not feeling like anything's too good for you and then just consistently raising your hand. But I want to go back to the boldness of how you first got the job, which is by criticizing them. I think that that's something that's really interesting because like with the job market being so tough right now, we also don't encourage a lot of young women to be super bold about what they want. But where is the line when you're going for a new job of telling them like, hey, here's things I can improve at your company versus being careful because you actually do want the role.

3:47The person I met luckily saw it as a compliment. Like you could do better. Like, why did you? And he was right. He was like, you're right. This was really sloppy. And I was like, yeah. And they're a newspaper. And so it was out of great regard for the Washington Post. It was not that I thought they sucked. I thought they didn't suck. And then they did. And I was angry about their suckage. And so, you know, and he said, you think you could do it better? And I said 100 times, you know, seven days a week and twice on Sunday. Like, I was like, are you kidding me? Of course I could. And then he said, well, why don't you show me?

4:18And so that was that. Other times it didn't work. I was up for a job where it was like one of these airline magazine type of jobs, right? Like writing for that. And I was very confident because I was a good writer. And the guy, it's always a guy, sometimes it's a woman, said, you're very confident. And I'm like, yes. Like, what do you want me to say? Oh, no, thank you, sir. And so I just didn't. I go, yeah, I am because I'm really good. And he was like, you shouldn't say that. And I said, it's factual. So I don't know what to tell you. And so sometimes it works. Sometimes it doesn't. Sometimes people find it amusing.

4:53Some people find it repugnant. I didn't get what I didn't get. And so like at one point when I didn't get an internship at the Post, I got it later. I got one later after I went to Columbia. So I had the Columbia degree, which of course was ridiculous because I was the same person. and he said when I didn't get it I said are you kidding me I'm better than all these people and and he was like he was he was like you know you got to wait your turn I'm like I'm not waiting my turn like why should I wait my fucking I don't even understand what that means and so and I said you know someday I'm going to be a really famous reporter and you're going to be retired in an old folks home I'll come visit you and say see you know and he would laugh you know know, I'd be funny about it.

5:37I wouldn't be strident or I hate that word about women, actually. I wouldn't be like mean about it. I'd be funny. I'm like, someday I'm going to be really famous. And you're going to, you know, be like being fed applesauce. And I'm going to maybe come visit you or maybe give you the time of day because that's the kind of gal I am. And so they think it was funny. And it was a truth to it. Right. I did it with John McLaughlin, who I worked for, who I turned in for sexual harassment. You know, I we did it. I did it with everybody. I was like, someday. Did you always think I'm going to be famous and a very successful journalist?

6:09Not journalist, but I thought I was going to be something special. I did. My dad died when I was younger, so I didn't have him around. I had my mom who wasn't particularly helpful about my career or anything else, really. So I kind of, my brothers and I are all really successful. And a lot of people think that when you have a parent who dies at a young age, you get very functional. And I think about my own many children, we remove obstacles from their way a lot of the time. and therefore they're surprised when they hit them, right? And I had a lot of obstacles. I want to talk about money. So when you went to Georgetown, who was paying for your tuition?

6:41When my dad died, there was an insurance policy. And my grandparents had left me some money. And so I managed my money since I was very young, 18 years old. And so, yeah, what was left to me was in an account. And I paid for college and handled all my finances from them. And I worked. I worked a lot. But my grandparents left me a good sum of money, enough, definitely enough for college and to buy a house. And so I managed it. I invested it. I made sure I had enough. But I always had a job. I always felt like I'd like to have my own money. I bought my own moped when I was a kid. I did babysitting.

7:19I did this, and I bought it myself. And so I like to always have control of money. I never felt comfortable with other people giving me money. And that's always been the case. Are there any financial mistakes you've made or pieces of advice you have for young people who are managing their own money for the first time? Well, I didn't take that job at Google when it was founded. I've been offered a lot of Internet jobs very early in the founding. And I was like, why do I want – like I remember saying to the Bezos people when Amazon was founded, they wanted me to work there early. And I said, why would I want to work for you?

7:47I was like, because I'd be getting married in Venice right now, I guess. I'm a pretty good investor. I've been a good real estate investor. But money doesn't motivate me compared to other things that motivate me. mostly what motivates me is I like the job I'm doing, that I enjoy it. I wish money motivated me more, but it just doesn't. It just doesn't.

8:14Do you have any advice for people of like, this is how you did it when you were younger? I had jobs. I had jobs, whether it was when I was younger and I babysat or I did photography in high school. I was a good photographer. I had a darkroom. And I took people's senior class pictures, charged quite a bit for them. And so I made a couple thousand dollars doing that and like five or six thousand dollars. And that's enough for a summer. You know what I mean? I had summer jobs. I'm trying to think. I sold chipwiches. I sold ice cream. I did a lot of freelance writing. And then I worked at the post.

8:46I worked. I always worked somewhere where I where I had my own job and I paid for all my stuff. Yeah. So, yeah. Because what I'm curious about is if you look at your business evolution, I think a lot of it now is oriented in owning your own IP and you've structured some very interesting deals. I did. So when did you start to learn to be more savvy? Pretty early. Pretty early. One of the things that, especially with women, they try to make you feel as if you shouldn't ask for more. And certainly men do it all the time. And so, you know, I'd be in different negotiations. They're like, hey, just take a little less and then we'll have a drink.

9:18we'll be friends. I'm like, I don't need any more friends. I have friends. You're not one of them. And I would always be like, give me the fucking money. Like, give me more. I would always ask for more. I would, what's really helpful is if you can link what's being the revenue to you. And so I always did that. So it was rather explicit. And so it wasn't like, oh, we'll pay you this. I'm like, no, I made this and I'll take this portion of it. And so I was always very aware of what the revenue was. And I think a lot of reporters certainly aren't. But I think I probably learned that from tech people.

9:49They got what I really liked about the tech business is, say, in media, they gave you a salary. You don't know why you got that. And you don't know what anyone else is making. And they try to keep that from you so that you don't have any. I think transparency is like, okay, I'm earning this versus my contribution here. And when you're in a tech scene, you do know your contribution, right? You're the founder or top engineer or whatever. And so I was always aware of what my contribution was and then asked for that, like whatever it was, especially when I started to be more entrepreneurial. And like at one point when we started All Things D for Dow, I was an employee of Dow Jones.

10:28We made a couple million dollars the first year in profit. And I was like, we just made that. And we didn't get anything. Like the company kept the whole thing. And that wouldn't have existed without us. It was our idea that then became the thing. And they, for some reason thought it was theirs. And I was like, this wouldn't, you know, and they're like, well, you're being paid as an employee. And I was like, well, what employee turns in millions of dollars in profit? Nobody at the time is still all media companies were struggling. So this was a significant addition to their profits. And I think at one point, we were 8 % of net income.

11:02We're like, Mr. and Mrs. 8%. Media companies don't make a lot of money. And so it was really irritating. And so the second year, and I called Walt, who was doing it with me. And I said, did you get the flowers? Because I didn't get the fucking flowers. Like we gave them millions of dollars. So the next year, we got a fee, it was still was small. And the next year, we said, we want a third, a third, a third, or we're going to do it somewhere else. We're just going to go like, I don't believe it went for three years. The second year, we should have said it's not happening. And that's what we did.

11:31And so they struck me because they didn't think we would make as much money as we did. And later, they're like, Oh, we should have given you a raise. We're like, no. But then it was fair. Like we made it. And without our I find something really satisfying for me is that like whatever, whether it was all things D or whatever I make, people then work for me. So I create jobs for people. And that's a really great feeling from an idea. Walt and I were always proud that we employed, you know, 40 people for 20 years. Like that's all those families. That's all those things. And they also worked really hard to make the product great, too.

12:07and so we really like that idea that you come up with an idea and then create economic opportunity for lots of people I spent a lot of time advising people both old and young of how to be entrepreneurial so it's a really it's a nice feeling because then you're in control of your destiny as opposed to other people just randomly and they make things up so it's like you know they do like why why is this person earning it is always once you actually pull the transparency anyway you notice white guys make more. They do. You can look at the numbers. Like it's really, and it's like, why? Precisely why?

12:41Like, are they better? Because you can entertain that. Maybe they're better. Probably not. Right? They aren't. But that's because women, whenever I manage people, which I don't, it's not my favorite thing to do, but I did always notice that men would ask for more undeservedly and women would ask for less, which they deserved. Like it was always the case. And I'd often be like, ask for more. You can ask for more. And the men were like, I think one guy I was, I was trying to fire actually. And I said, he's like, I think I deserve a raise. I said, I think I should fire you. See, interesting difference in our opinion about you.

13:20And he's like, well, I think, you know, I did this and this and this. And I said, I think you fucked up this, this and this. I said, so what I'm doing right here, and I actually, it's the first time I was very honest with something. I'm like, what I'm doing right here is preparing to fire you. And you're not getting a raise. That's definitely not happening. And it was so interesting. But his mentality was to ask for more. I also think it's about learning to ask for the right things. When I look at the negotiations of our female employees versus our male employees, our male employees are so much better at understanding they should ask for more equity because they understand that that's where the real upside is.

13:51If it is. Yeah. If it is. Yeah. Versus only negotiating for pennies and dollars. Or if they are asking for a raise, it's like 20, 30, 40 ,000, not can I have$5 ,000 more? No, it's true. I don't know what that is. And I hate to say that's the case, but it is. It really, truly is. You just have to understand what your leverage is and what your contribution is. And that's why I like to make them explicit, because then it's just right there. Like, if I'm making this much money, this is how much I want of it. And it wouldn't exist without you. And one of the things that's, I think, very hard, especially for women, is willingness to walk away.

14:24Like, I think I'll leave then because I can make money elsewhere. And I think one of the attributes I have is I'm always willing to leave. And it's not a threat. I don't do it as a, like, you know, I'm going to leave now if you don't give me what I want. I never do that. I'm just like, okay, then I'll leave. Like, because I believe in myself and my own entrepreneurial. I believe in my record. And I believe I can do it myself. You have to be willing to walk away. And that's and really mean it and believe in yourself. What I'm really curious about is how did you make the decision to leave the Wall Street Journal?

14:55And then what happened when Rupert Murdoch said that he was mad? Yeah, he wouldn't let you take that IP with you. I knew he wouldn't let me take the IP because IP is everything in media. But I offered to buy it. Right. And I thought that I made a fair offer and he wanted an enormous amount of money. Ten million. And then I jokingly said to them, I'm like, I could buy fuck Rupert dot com. and start it there. And I think I will. Like, I didn't ever buy the, but I could, at the time, I did check you could buy it. I think it was 10 or 12. It was, they were having a special on proctorrooper.com. They have a, they have a, but I was like, it was like, what's valuable to you?

15:30Now, I would have liked to have that because then I would have had the feed. I would have, it's an easier, but I'm, again, willing to start from zero. Like, I'm like, I've started from zero before. I've built it up before. It's easier to start from one number. Same thing happened in the New York Times. They kept my feed and gave it to someone else. And they're like, a successful show, I'm like built on someone else's feet. And I made a stink about it because I was like, how can you do that? Like how can you pretend you were successful when you weren't on your own? And so I kind of like starting from zero because then you know if it was you or not.

16:01And one of the things when I was at the Post, there was a particularly bad guy who would steal all my ideas. This is something that happens to everybody in their career. How old were you? When was this? In my 20s. And I was full of ideas, right? I'm always like full of ideas. and he would always steal my ideas. And it was, so I stopped telling him things, right? Like initially you're like, assume people don't do that. And he did it. And I said, you know what? You can have it. I have a million ideas and you don't have any. Like, fine. It's easy for me. And it was a good feeling because I took back control rather than be victimized by that.

16:32I was like, got it, clocked it, understand people do that. It was a good lesson. And then I was like, I can think of them all day long and you can't. And so and he's in the same fucking place. Really? Yeah, he stayed in the same fucking place. Of course he did. He didn't have any good ideas. Interesting. And what about your new deal? You decided it was a 70 percent, 30 percent profit split. Why did you decide to do that? Because I should. Honestly, it should be 100 percent. No, it shouldn't be. Anyone that you do a deal with and Vox happens to be a great partner, by the way. We love working with them.

17:05It's a great working environment. They're great people. They do their work really well. You have to sort of evaluate who you like to work with. Then the second part is what – like anybody, and this is not Vox or anybody else, is like, okay, I'm paying a lawyer what? And for what am I getting? What's the service I'm getting for whatever I'm doing? And then you try to figure out, could I get it somewhere else? Could I do it myself? Could I hire someone? So one of the things Scott and I did was a market check. Like we went around and talked to people. And what are the ins and outs? And there were things Vox wanted that we were willing to give them that was better for them.

17:39We were like, OK, if you do this, we think in the market, you have to be knowledgeable about what the market is. It's worth this in the market. Why are you getting more? But I do that with my agents. I didn't use an agent from our podcast deal because I was like, what am I paying you millions of dollars for? They're like, because we're your agents. I'm like, no. And we offered them a certain amount of money. And, of course, they like to work on a percentage basis. If you understand the underlying value and you understand the market, you know how much you should pay for something, right? And people frequently overpay.

18:11They don't as much underpay, but they definitely overpay. So I'm like, this is the value of it in the market, and this is what I'm willing to pay. And if you know what the market is paying, you can know what you should pay people. And then you're like, look, this is what everyone else is being paid. I'm not going to pay you more. And so that was why we did that. I want to change and go into, like, your relationship with tech, too, because I feel like you were the first journalist to be like, OK, let's pay attention to this. Let's start doing this conference. Yeah. And you talk a lot about man-childs basically with money and power.

18:37And I think we see that so much in the administration today. I'm curious out of all the people you've interviewed, like who has changed the most once they got access to power or money? There's a couple people. I mean, it depends. Some people start off irritating like Bill Gates and grew up and became more mature and became more interesting and had a wider perspective. That was great to see that happen. At one point I was with – we were interviewing Melinda and I was standing backstage with Bill and she was so smart. I'm like, I like you 10 percent more. And it was really funny. And it was – and then I happened to be married to someone he liked.

19:16He said, well, I like you 10 percent more because he was always trying to top people. But, you know, people that progress I appreciate and certainly he has. Mark Cuban is another person. Steve Ballmer also what a jerk but then he's kind of charming now and of course the bar is he's like you like me now I'm like the bar is low unfortunately a lot of people go the opposite direction or they don't grow at all really that's they never they never progress and you know I put Mark Zuckerberg in that category I would put Elon Musk clearly but he's got personal problems he's got alleged drug problems but it's very clear what's going on there and you know they have they they They go backwards as they get wealthier.

19:58You know, there are deleterious effects of wealth, which is that people kiss up to you. They agree with you. You're always right. And unless you have a very strong constitution, you can't resist that. And so a lot of them just they live in these ever smaller worlds of enablers, you know, and sometimes it ends badly, like with Tony Hsieh, who was at Zappos. Lovely guy. but became more and more addicted to drugs. Drinking people around him became less and less good. I mean, it's a classic story. It's not a – A bunch of yes men. Yeah, it's a bunch of yes people really. And so, you know, it ends tragically for them.

20:38In his case, he died because of his – well, lots of reasons. But he had mental problems. Nobody got him the help he needed. And he really basically killed himself if you think about it, the way he behaved. And so, you know, a lot of people end up like that. A lot – most of them do actually. They become these sort of – they live in these little bubbles and everyone tells them everything is great and that's that. And that's where they live. And so those people I don't talk to anymore. I do talk to Gates. I talk to Cuban. I talk to – you know what I mean? Like and they're willing to accept feedback which is I think, you know, I don't do it for my pleasure or my entertainment.

21:15It's like I don't agree with you on that. And same thing in media people. You know, there are those who can take criticism and there are those who just can't. And I think as you become wealthier, money is sort of the way it happens. But more powerful, you tend to get that way, which is kind of ironic that they were so obsequious to Trump. Here are the most powerful people on earth being obsequious to Trump. What? Like, really? What's the money for if not to say fuck you? Like, what's the point of having fuck you money if you can't say fuck you? And, you know, look at Elon. I'm apologetic of the things I tweeted.

21:51Like, has he ever apologized to Paul Pelosi for tweeting heinous things about gays? Has he ever apologized to all these people he called names? No, he apologizes because it's in his financial self-interest to do so with Trump. He's worried about the existential crisis to his businesses. And so that's even worse. You're like, really? You can't just stay with the fuck you. Like, just stick with it, even though, by the way, he did go over the line. He did. But probably he's not inaccurate about a lot of things he was saying. And you used to be close with Elon. When did that relationship kind of shift?