Kara Swisher has been called the most feared and well-liked journalist in Silicon Valley. She’s been covering tech industry leaders for decades...and is famous for making them sweat. Just ask Mark Zuckerberg, Jeff Bezos, or Elon Musk. Her secret to building those relationships with entrepreneurs? She’s not afraid to pick up the phone (or slide into a DM) when she has a question.
On Being A "Bad Employee"
Carly: You have said you’re a bad employee.
Kara: I'm a terrible employee.
Carly: What do you mean by that?
Kara: I don't like to listen to bosses. I'm not a difficult employee. That's very different. I'm not obstreperous for no good reason. I just want to do things on my own and I don't want someone to tell me what to do. And I recognized that early in my life, that I don't like being told what to do. And I don't mind making mistakes if I do it on my own.
On Meeting People Early
Kara: I spent a lot of time meeting the people who were creating the internet…. I made it my point when I saw something interesting to meet the founders most of the time.
Carly: How do you get them to trust you?
Kara: I just call them. I mean, the problem with most journalists is they're incredibly shy. I just call people or I contact them by DM. There wasn't DM'ing, of course, back then. But I call them and I go visit them. I think most people don't do that. I know it sounds dumb.
On Being "Feared"
Kara: I don't think I'm feared, particularly, unless you do something wrong. I guess I'm scary. But the reason you should be scared is because you did something wrong, not because I know about it…. I think I'm honest with people and that's very different. I think I'm honest.
On Speaking Up
Kara: I think a lot of people tend to not say what's right in front of them, right? Everyone sees an awkward situation and no one says anything. Everyone looks down, but nobody says anything. I say something. I'm like, "No, that's terrible."
I'm being outspoken with informed opinions. And that moment where they say "Kara's being outspoken" is where [a lot of] people [would] shut up. And that's where I don't shut up. When I have someone try to shut me down by insulting me or calling me bossy or outspoken, that's when I go full in. That's when I know I'm winning the situation.
And so, I think one of the things that I try to do is I try to develop a point of view…. And then I have the guts to do it. I have the guts, if it doesn't work, to be okay with that. If it doesn't work, I then examine it and why it doesn't work.
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