Tech journalist Kara Swisher has known Elon Musk since the last century, when he was a fledgling tech entrepreneur in the late ’90s. She has interviewed him extensively numerous times in the time since, but as she explains in the latest episode of On With Kara Swisher, they aren’t on speaking terms anymore. “I’m an asshole. He emailed me this recently,” Swisher tells producer Nayeema Raza, who interviews Kara in this episode.
They talk about her extended history with the increasingly controversial billionaire, his idealism, where they have agreed and disagreed, and what’s now gone wrong — with Musk, with Twitter, and a lot of other things. Below are some highlights from their ranging conversation.
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First off, about that email:
Nayeema Raza: Before we go down memory lane, I want to snapshot, so people understand as they’re listening, where your relationship with Elon is today.
Kara Swisher: He’s not speaking to me.
Nayeema Raza: So one word to describe it.
Kara Swisher: I’m an asshole. He emailed me this recently.
Swisher and Musk had been emailing back and forth, discussing him being a future guest on this very podcast, and talking and respectfully disagreeing about Twitter and the economy.
Kara Swisher: And then I tweeted something that he didn’t like. I tweeted this Washington Post article, which cited an anonymous U.S. Defense official talking about Starlink. The official said, “Elon’s going to Elon,” and I wrote on Twitter, “Elon’s going to Elon kind of says it all.”
Nayeema Raza: So this is this mid-October reporting from Washington Post where Elon was, at the time, kind of wavering on whether or not he was going to keep funding Starlink [in Ukraine].
Kara Swisher: But I didn’t agree with this Defense official. I think they should pay Elon, and I said that. So the next couple of tweets was like, “I think he should be paid.” He does have them over the barrel and can say what he wants because I think it was Defense Department’s problem.
Nayeema Raza: And then on October 17 at 9:45 p.m. Eastern, you get an email from Elon.
Kara Swisher: Yeah, late. It’s always late. I was up at night having chocolate sandwiches. I don’t know what’s happening.
Nayeema Raza: And the subject says?
Kara Swisher: Just says, “You’re an asshole.”
Nayeema Raza: And a screenshot.
Kara Swisher: Yeah, the screenshot was there, which is fine. In this case, I was supporting him, which is really kind of ironic.
Raza asks if she replied.
Kara Swisher: I did. I was like, “Are you kidding me?” I wrote him back saying, “I actually was supporting you here. You obviously are getting bad information.” I wasn’t being obsequious anyway. I’m like, “What are you talking about?” First of all, whatever, he can call me an asshole. I don’t care.
Nayeema Raza: Did you hear back?
Kara Swisher: No. No. I explained it. I said, “This is what I’ve been supportive of you. Here, here, here, and here. I don’t know what you’re talking about. You can attack me for other things you don’t agree with me.” And I thought it was super thin-skinned. I just did. It was wrong and thin-skinned at the same time.
Swisher also explained how and why she believes what Musk did with SpaceX and Tesla was so impressive, and how he and his big driven ideas really stood out among other tech leaders. And she was initially excited about him buying Twitter, too:
Kara Swisher: You know what? Honestly, when he started going after it, I thought this is the best person. Yeah. He could do it. Yeah. I think I said that, and a lot of people were like, “No way.” I was like, “You know what? He is.” There’s very few people that could bring together the kind of people needed to make this thing better.
Nayeema Raza: We’re going to get to Twitter a little bit later, but do you think he gets off on being an underdog?
Kara Swisher: Yeah. That’s okay. I don’t mind. Someone had to do it. “It should be me. I will go in and save.”
Nayeema Raza: So what drives him? Is it the … This is an opinion based on your reporting and relationship with him. What do you think motivates him more? The desire to do something big or the desire to disprove people who are naysayers?
Kara Swisher: All really good entrepreneurs are contrarians. They just are by nature. So, on good days, I think he really wants to make a dent in the universe, he does. In the worst case, massive narcissism. But they sometimes go hand in hand. One time, I caught him when he was very emotional after he had a very difficult period with Tesla, and he was almost crying because he said that the Earth is going to die. If I heard that from most people, I’m like, “Get out of here. You’re a liar.” So I think he really wants to make a dent in the universe.
Raza also asked Swisher if she thought Musk was reflective and capable of change:
Kara Swisher: Yes, of course. Of course. He’s very thoughtful. He just has this layer of just completely — and it’s gotten worse and worse over time, as he’s gotten richer.
Nayeema Raza: He’s thoughtful until he’s not.
Kara Swisher: Well, it’s just the adulation and the money. I don’t know if the money, I don’t think he spends that much. I mean, I don’t think he’s particularly than anyone else. But the adulation from the fan boys has gotten out of town, including the ones around him. That’s my only guess.
Nayeema Raza: And that you’ve seen that change over time. You think you’ve seen him become more and more encircled, more and more powerful, more and more …
Kara Swisher: They get isolated, isolated, isolated, and their circles become ever smaller. They never meet real people. Except online, and that’s not real.
At another point, Kara notes that Musk might not be capable of distinguishing the difference between doing good for the world and doing good for himself:
Kara Swisher: For Elon, doing good for the world and doing good for Elon are intertwined. I think it’s very easy to say: “This son of a bitch, he’s a narcissist, he’s malevolent,” but that’s way too easy for this guy. He does want to make a dent in the universe, he really cares. It’s much more complex than “What an asshole.”
But at the same time, she was deeply and personally offended when Musk, in the first weekend after he acquired Twitter, promoted a conspiracy theory featuring an old anti-gay trope regarding the brutal attack on Paul Pelosi:
Kara Swisher: I’m not a particularly sensitive gay person, but you cannot do that. He can do it, but boy, does he have to pay the price for doing it. I just was like, what an irresponsible, terrible thing to do in one of your first acts as CEO of this site is to … Talking about misinformation, by the way, I’m also angry at misinformation and the impact. So misinformation, anti-gay, plain mean to a guy who got attacked. Everything about it was loathsome. That’s enough. I’ve had it. Enough. Enough.
Swisher said she is still trying to empathize with the guy, but insisted he had to apologize for the Pelosi tweet:
Kara Swisher: I still like him, even though he doesn’t like me. I still like him. I still like him, but he has to apologize for the gay fake-news thing that he put up or we’re not speaking ever again. And I have never said that to him. He’s got to apologize for that.
As for the future, Raza asks Kara, “Are you hopeful or hopeless about Elon?”
Kara Swisher: Can I be both?
Nayeema Raza: Pick one, Kara.
Kara Swisher: Today? Hopeless. He’s capable of great things here. He’s behaving … He’s disappointing in how he’s handling himself. And in the midst of all this disappointment, there’s all these really good ideas. It’s just so bossy. “I’m the law.” It’s so narcissistic. And the thing the other day, the advertising thing, someone asked about the difference between Twitter and Elon Musk.
Nayeema Raza: Yeah.
Kara Swisher: They’re the same thing. He can’t pretend. These wealthy people like to pretend they’re not powerful. It drives me crazy. He’s very powerful. What he says matters. He can hurt people if he wants to, even if he doesn’t mean to. And so, he’s got to have a greater sense of care around what he’s doing and just slightly more kindness. He can still be puckish, and rude and funny, just like I said. He’s all these things like funny, rude, compelling, obnoxious, accessible, easy to deal with, hard to deal with, always on, outspoken to a fault, angry, charming, intense, and also strikingly confident. You can be all those things. That means you’re a human being. But I mean this in the nicest way, Elon, I’m not the asshole.
Nayeema Raza: You want to finish that thought?
Kara Swisher: That’s my thought. I’m not the asshole.
This interview has been edited for length and clarity.
On With Kara Swisher is produced by Nayeema Raza, Blakeney Schick, Cristian Castro Rossel, and Rafaela Siewert, with mixing by Fernando Arruda, engineering by Christopher Shurtleff, and theme music by Trackademics. New episodes will drop every Monday and Thursday. Follow the show on Apple Podcasts, Spotify, or wherever you get your podcasts.