Offline with Jon Favreau - Kara Swisher on the Very Online War in Ukraine

Episode Date: March 6, 2022

To open Offline’s new feed, Jon interviews Kara Swisher, Silicon Valley’s most feared and respected journalist. The two discuss the ongoing war in Ukraine — how it marks the first true conflict of the internet age, why Putin is losing the misinformation battle, and what makes Zelensky a compelling online hero. Kara also gives Jon insight into Big Tech’s most important founders and teaches him a few interview tricks to use as Offline continues.For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [e-mail] and include the name of the podcast.  

You know the psychology of these tech founders better than anyone. Do they just see themselves as misunderstood geniuses who are trying to save the world if the media would just stop attacking them? That's what it feels like to me. No, no. I just did a really great interview. I recommend listening with Brian Chesky at our Pivot Conference. I like Brian. And he understood.

He was like, look, if you get licked up and down all day, eventually you're going to think you're Jesus, right? You know what I mean? I don't like to mix those metaphors, but you know what I'm saying. He talked a lot about this issue, about being told you're right. You surround yourself with people who agree with you violently. Like, yes, that's, mm-hmm, that Kara Swisher, she's so mean. You know, that could be whatever, if you say it over and over again. And sometimes I am mean, but not all the time. I'm Jon Favreau. Welcome to Offline. Hey, everyone. Before we begin, let me just say, welcome to the new feed. I'm very excited to keep these conversations going. There's so many corners of the internet we haven't covered yet. There are so many ways it affects our lives we haven't talked about yet. We have a bunch of really cool guests lined up that I can't wait for you to hear from. But we're still trying to figure it all out. So if you have a topic or guest in mind, please let us know. We love hearing from you.

In fact, some of the guests and topics on previous episodes have come directly from your suggestions. So keep them coming. As for today's guest, who better to kick us off than Cara Swisher, Silicon Valley's most feared and respected journalist. Many of you know her as the host of Sway, her phenomenal podcast with the New York Times, or as the co-host of New York Magazine's Pivot.

But Cara has been reporting on the internet since the AOL era, interviewing nearly every tech founder you can imagine. I could have talked to her about anything, because she's been covering this beat for far longer and better than I have. But as I've been glued to the coverage of Putin's invasion of Ukraine, I've been struck by how this is the first major war of our extremely online era, which is significantly shaping how it's being waged. Kara's been talking and tweeting about this too, so I figured we'd start there. I asked what she thought about the steps that tech companies have taken to stop the spread of Russian disinformation,

the threat of cyber attacks, and how the Ukrainian people and their president are using social media to rally the world to their side. We also talked about whether humanity is meant to be connected at this scale, her psychological assessment of the various tech founders she's interviewed, and why she's such a good interviewer. It was a fun conversation, and not just because Kara is the only person I know who's more proudly addicted to her phone than I am. As always, if you have questions, comments, complaints, or topic ideas, feel free to email us at offline at crooked.com. Here's Kara Swisher.

Kara Swisher, welcome to Offline. Thank you. Thanks so much. It's good to see you. I haven't seen you in a dog's age. So long. Probably since we've been on stage together for a Pod Save America, I think. Probably. That was a million years ago. Yeah, that was the before time um i was having a hard time picking a topic to talk to you about because okay you could wax eloquently about literally every issue we've covered on the show and all the ones we haven't marvel movies there's 22 of them i've been thinking a lot about how um putin's invasion of ukraine might be if not the first, certainly the biggest war of the very online era in which we live, and how that's affecting the way it's waged. And I know you and Scott Galloway covered this this week on your excellent podcast, Pivot. So I thought maybe

we'd start there. How's that sound? Sounds great. What do you make of the steps that tech companies have taken to limit the spread of Russian state-sponsored disinformation and propaganda? I think they should have done it years ago. You know, I mean, this was happening in so many ways, usually under dark of night kind of thing, cloaking. And this is so obvious, it's pretty easy for them to deal with, you know, because it's a very real situation. There's a lot of pressure here. It's a civilian population that's getting attacked. There's a lot of things where they don't look great, you know, if they continue to allow this to happen. And so I think they've moved in pretty, you know, they've tried,

they've tried to demonetize. They've tried to do all kinds of things. This is stuff, again, they could have done before when they were doing either anti-vax or big lie information, things like that. And so I think what's really important to think about here is that they're capable of it. Now, that's a good thing and a bad thing, right? Like they're capable of it, meaning they can, you know, I'm not a conservative person, but I certainly do hear their worries about a small coterie of people being able to do enormous damage to the information systems of any country. And you can see why autocrats are worried. And they also want to use these systems at the same time. So it's kind of an interesting problem is that they're a tool and a weapon at the same time. Yeah, that was my first reaction, which is I'm glad that they're doing this now. But

where have you been on a whole bunch of other issues? Because at the time, you always told us, oh, we don't really have the power. Tweaking an algorithm won't help. We can't do this. Content moderation is too difficult. And it's like, well, I guess when there's an invasion of a democracy by Vladimir Putin, suddenly you can take action. Yeah, you can. I mean, I think it is complex. Let's not be naive in the price. The problem is the way it's architected. It's almost impossible to get your arms around a lot of this. And I think that's one of the biggest problems is that the architecture is rotten in that regard in terms of malevolent players being able to misuse these platforms. They're very easy to manipulate.

They're very easy to use propaganda. I was struck by how Facebook comms chief Nick Clegg framed their actions. He said they were restricting access to RT and Sputnik based on requests from a number of governments, shouldn't they be restricting access based on their own internal content standards rather than what's essentially lobbying from politicians? Yes, yes, they should. They have rules. It's interesting because I was just listening to an old interview I did with Mark Zuckerberg where he made that mistake about calling Holocaust deniers don't mean to lie. I think that's what he essentially said. And then two years later, he took them off, was the distance between when he decided it was okay and then when it wasn't okay.

And that's what it is. It's so capricious based on Mark or whoever's inside that room that decides these things, but it's a small group of people that decide these like they did on January 6th. You can agree that Donald Trump should have been deplatformed, but wow, it's two people that really got him, Mark and Jack Dorsey. That's, that's, I don't know, I find it worrisome. I mean, Ukraine has also asked Meta, Apple, Netflix, and Google to restrict access to their services inside Russia in order to isolate that country. How do you feel about that? Not loving it. At the same time, these are the things we apply, right? How different is that than sanctions, right? Except the government doesn't control them. And so, you know, this is what you do to control societies now is you control the information. One of the, you know, the way you take over a country

is you first grab the communications tower, the TV tower. The second thing you do is grab the money, grab the this, you know, it's not all about just like heedlessly bombing civilian targets, which is so appalling on every level. It's also grabbing the ability to use propaganda. And this is why a lot of autocrats do like the internet, if they can have control of it, because they can like in the Philippines with Duterte, etc. He's really used the internet to his own advantage. Erdogan in Turkey and things like that. But I do think, you know, they can ask, they can ask, they should ask, the government should ask. But you know, they've also asked for a group of hackers to just go in there and make a

mess of the place. It's all pretty scary, especially when it comes to grids, power grids, and other things that are all, it's not just the internet and people yelling at each other and doing false reports and false videos. It's linked to a lot of much more dangerous stuff like credit cards and electrical grids and important emergency power and light and gas and everything else is all on a computer system. I know. I know you recently had uh nicole perlroth uh new york times cyber security reporter on um or anything from that conversation that should worry uh worry us about uh the united states vulnerability to cyber attacks yes everything everything you know her book is called this is how they tell me the world ends so that will give you

an idea of what nicole is right not che. Like this? This is how it ends? Oh, I thought it was going to go in fire. But it could because of these things. And so one of the issues around the United States is, look, we have an open system. We really do compare it to other countries. And that's a good thing. But at the same time, it's this huge landscape to attack. It's a surface area of attack is so wide. And one of the things we're quite good at, and which we don't talk about, is the U.S. is very good at offense. You know, Stuxnet, which we did with Israel, was really something else to be able to shut down those nuclear, whatever they shut down. But they did. It was a big hack that we did. And so we sort of taught other people how to do that, the U.S. did. And we have a really good

offensive capability when it comes. And we also like to like go in there and scare them a little bit and like show ourselves, because then it shows we're in here. But one of the things that's a problem with a lot of the recent ones, whether it's SolarWinds or some others, is they're in here already. They're in a lot of places. We just don't know. One of the way Nicole described it is they might have come through the door, but now they've opened all a bunch of windows. We don't know which one and they just keep it there so they can get in at any time. And so we don't know where they are, but they're in there. And we have such a large surface area. And there's all kinds of vulnerabilities. Two-factor authentication was not a thing at the one, the pipeline,

the colonial pipeline. They didn't have two-factor. I have like three-factor authentication on everything. That's like your most basic thing. I know. And even that's not that hard to hack, from what I understand. But it's harder. And so a lot of this stuff is everyone's left to their own devices, so to speak, to protect them. And there should be a much bigger hand by government, who, by the way, has its issues. Like, remember Edward Snowden? It seems like they were spying on everybody.

But the government really should have a much more transparent role here with corporations and everything else. It shouldn't be up to these corporations to have to deal with it. Even Google. I remember a Google executive telling me, like, we are like a foreign country and they attack us every day and we're barely keeping up. And this is Google. Can you imagine if you're, I don't know, a car company or a hospital or whatever. Back to your point about how this is a complicated issue for a lot of these tech companies and a lot of these social media platforms. It doesn't seem like it's possible for these companies to remain neutral in the now global struggle between democracy and autocracy. I think the question is, where do you draw the line?

If you block RT and Sputnik, what do you do about Donald Trump's propaganda outlets, right? Like you could make a similar case for some, for Tucker Carlson's show or One American News. And I wonder if you're inside these companies, you know, if you're going to give them some credit on this, they're thinking, okay, well, Russia might be easy in this case because they're invading a country and they're murdering people. Yeah. But where do you draw the line? Well, do you have to draw the line? There is one side you say, look, this is an incredible situation.

Like, you're not going to do it all the time just because you do it once doesn't mean you do it other times. Just because you could, we always could. Right. We could always do this. So that's one argument sort of for it. The other is, yeah, I had a tech executive say, why don't we just go for Fox now? Like, you know what I mean? Like, they were joking, but like, they're like, how far is it?

Because they're sort of like RT, and you could look at some of their stuff. And, of course, now they're dialing that back because of the brutality of what's happening because they see the impact of it. But, you know, it's a problem, you know. I wouldn't take Tucker Carlson offline as much as I pour him. But you could see someone making that argument. Why not?

Yeah. I mean, well, the wars also made me wonder about the limits of disinformation as a weapon. Right. There are few autocrats who've used the Internet and social media to weaponize propaganda more effectively than Putin. And yet it's because of the images of his brutal invasion that have been all over social media that opinion has turned so harshly against him. And now that includes some of his own people at this point. What do you make of that? Is Putin losing his own information war? Oh, yeah, that's the problem. It's so porous. He's unfortunately dealing with what he was taking

advantage of before. It's so porous, there's lots of ways around it. And so, you know, it cuts both ways. I was just talking to someone how he'd forgotten how good the internet is. I think it was a conversation with Brene Brown, but like there's a lot of good to it. There's a lot of things that are wonderful. And when it was started, it sure had that feeling like we could connect each other, we're going to meet people, we're going to do this, we have commonality. And then the other parts of it, you know, came in, which was the division, what we don't like about each other, the ability to dunk on each other, etc. And so it cuts both ways for him. He can use it for propaganda, but there's a point where then it becomes unbelievable and people do try to seek out other information. I mean, one person who seems to have successfully

rallied public opinion during this war is Ukrainian President Volodymyr Zelensky. Why do you think his use of social media has been so effective? Because he's this guy in a shirt. He looks good in it. He wears a little thing. He looks like he's under siege. He looks tired. He looks, he's like, oh, here I am trying to defend democracy with my t-shirt. You know, it's a great shirt. His messages are very simple and to the point. He's got a great, I don't want to say he's got a great narrative because it's true, right? But he's definitely leaning into beleaguered, you know, it does remind one of movies like Marvel.

I was joking about Marvel at the beginning, but it comes to mind, right? We've all been sort of trained in this area of you're going to snap your fingers and end human race, and then the Avengers are going to take over, that kind of thing. And so we have this visual, and he's been using it beautifully. He has other people on it, like there's characters and the people, like he took that one picture with him and his defense minister after the picture of Putin and his defense ministers and the long weird table. So he posed with his defense minister

like they have their arms around each other, right next to each other. He's not scared of COVID, nor the Russians, that kind of thing. Yeah, it's very of the people. It's also, it seems geared towards combating misinformation itself, because if Zelensky had been inside somewhere, either in a palace or in a house, if he was all dressed up, you know, the Russians could probably make the case that, oh, he's not really in Kiev. He's not really in Ukraine. He's actually fled. And what he did is basically showed people, here I am outside. You can recognize, you know, Ukraine in the background. And I think he had one of his ministers like hold up the date on his phone too, to make sure that – So really just a smart play to sort of fight the disinformation coming from Russia.

He's getting out among people. He's being seen. He's going around them in some ways, and it's getting out. He's addressing people. He looks like he's there with them. He looks tired. Everything he's doing is just incredible. It's memeable.

I hate to say that. It also is admirable. This is how people get news around the world, right? This is the bits and – I hate to, again, say it. It's memeable. I hate to say that. It also is admirable. This is how people get news around the world, right? This is the bits and it's, I hate to again say it, it's snackable. It's very snackable what he's doing. And, you know, he's an entertainer before, so he does have some understanding of this, you know a performance, because like one of the things I've been worried about is that like our very online culture has distorted and even minimized how dire the situation is in Ukraine right now. And I saw you tweeting about Julia Yaffe's comments on this. She's a Russian born American journalist, writes for Puck. And she made the point that Americans love an underdog story. We love new celebrities like Zelensky, at least for a little while. But most experts, of course, believe that Russia still has the overwhelming military advantage here. Does that distorted narrative worry you? Or is it okay, because Ukraine needs all the support it can get? You know, I said this on, I said this several times last week. I'm like, I get the story.

Is it really, you know, they've managed to hold them off and that is impressive. But yeah, guess what? You know what? Like a lot of those trucks, that's a lot of trucks. And eventually this is how they've done their other wars across the world, Chechnya or anywhere. This is an old trick by the Russians. Like, let's just throw millions of people at things and, you know, deaths be damned. But I do think there is an element of having won

the persuasion war is very important. And so today the tools instead of television or radio, like the way Winston Churchill used it, are the internet, they're memes, they're visuals, there's jokes, there's information getting out, there's pointing out that the person's a liar especially around say people who had died russians who have died i thought that text exchange was really effective like it is it just it can you talk about that a little bit this is this is the

ukrainian i think i don't i forget he's the representative of the united nations i think i can't remember i don't know what his title is he got up and read a text message between a russian soldier and his mama. Like, that was my mama, like that kind of thing. Essentially, it could have been scripted, like, you know, mama, they don't want us here. We're running them over with tanks. You know, they're jumping in front of our, it's like literally a Hollywood screenwriter. Couldn't have written it any better. And so, you know, it really, it tugs at the heartstrings of a lot of parents in Russia and mothers and, and that these soldiers do not want to be here killing these people.

And he read it and it was like, oh, you don't look good in that. And so what can Russia say? Like what kind of meme could they do? There is none. Like, yes, we're the oppressors. We're like the Nazi thing's not working as they bomb Holocaust memorials. Well done, Russia. I mean, just terrible. Like, I'm like, please, what are you doing? Like, what are you going to like squash

puppies next? That kind of thing. And so they don't have a, they don't have a persuasion element. And you know, war is about brutality and killing and everything else, but it's also about persuasion and getting people, putting either fear into them or hope, right? And I think Ukraine has done the hope part really well. We're still here. We're still here. Yeah. Well, at the very least, I think it gives them a chance because, you know, it's hard to do a counterfactual, but if you didn't have Zelensky on social media all the time, if you didn't have this sort of campaign from the Ukrainians to sort of rally the world to their side, you could imagine Putin sort of rolling in

and maybe you don't have the alliance that you have with all these countries around the world. Maybe you don't have the global public support. And they could, you know, the Russians could still defeat them anyway, but they probably think to themselves, it gives them a fighting chance, you know? They've been hurt badly in the persuasion area, and especially among young

people who pay attention to stuff. It's also been very, it's not been organized either. It's sort of just been well done. The couple that married and then now they have guns, like posing adorably, I was, you know what I mean, with guns, not so adorable, but nonetheless, they need the guns. You know, there's visuals everywhere. Everyone's got a cell phone. And so they're, you know, the Russian tanks coming in and people, average citizens holding like plastic bags of like water, like, get out of here. You know, that's effective. Like the broken Russian tanks across the landscape is effective.

It's not just bombs anymore. It's like visuals all over the place. And I think there's been, you know, people, the kids downstairs in the subway, right? Yeah. You know, just every visual that comes out is pro-Ukraine and anti-Russian. And how could they have done this? And I think that's, it's the first internet enabled war. And I do think it does have advantage. And it also creates a population that is not going to roll over even if they get rolled over. This is going to be a real problem for Russia forever.

You can't quash this down. You can't. You can try. It's hard to put this back in the box. And at home. At home. That's where the real damage is. They're trying to arrest everyone.

Can you arrest everybody? You can try. It's not a great situation to be in for them. Well, and even if he captures Kiev, can he hold the country is the question. He looks an idiot he looks old he looks brutal old and problem with this madman is that he's got nuclear weapons which is that is correct which means we can't which is problematic interesting on the internet someone was like why don't we go in there and just bomb i'm like nuclear war that's another you're being a wimp cara i'm like no the online conversation

about nuclear weapons and suddenly we got like fucking you know 500 nuclear experts just talking casually about uh global annihilation yeah it's the most accurate and darkly funny thing i've seen is from there's been great experts though have you liked that i've found this has been very it's it's a little better than covid because these people are actually you know some harvard experts oh well you got some of them yeah some oh yeah some of them are experts then you get people just popping off who don't know what the fuck they're talking about let me tell you about geothermal pulses i'm like no this yale law professor scott shapiro uh tweeted this week the five minutes that the icbms are in the air will be unbearable on this platform yes

honestly like some of the conversation that's what it was making me think of and i look i people are oh my god part of the problem part of the problem here is you know i saw someone there was a an msnbc another image of like very young people in ukraine just holding weapons and they tweeted like you love to see it hashtag ukraine and i was like oh my god it's just like it gets a little much. I think the reason people do that and tweet that stuff is like they want to help. And the challenge with war in the era of social media is social media gives us this sense of proximity and immediacy and urgency. But it doesn't necessarily give us more agency to solve the problem.

So we can see the tragedy, but we can't do anything about the tragedy. So we try to do all these a little more performative things, you know, where we're tweeting hashtags and doing this and all this other silly stuff. Wasn't it hashtagavism on SNL many years ago? I'm going to write a tweet right now, that kind of thing. Although it does have influence. I think it does. It creates, you know, I always thought the idea of the internet was the world talking to each other. And that's what's happening.

The world is talking to each other in some ways, not everywhere and always, but people are talking to each other. And often it degenerates into terribleness, like over COVID, that certainly took a bad turn. This happens to be a hopeful narrative, right? And most Americans, at least, or most people in democracies are like, that's our people. Right. Ukrainians are our people and and they're adorable. And the Russians, you know, and of course, we've been conditioned by years and I'm not going Tucker Carlson on you, but we have been conditioned by years of imagery of Russians on Bond movies or anywhere. You know, they're always up to something awful. And often they are, by the way, FYI. And so,

you know, I think we, it's a very easy narrative for people to fall into this narrative. It's a historical stereotype, for sure. It is. It's longer than just, it's not a meme that's doing this. This is deep in our, the bones of the United States is a Russian competition, even if it was 50 years ago, even if it was, you know, Cuban, it's still the Cuban Missile Crisis with these people. And so we'll see. But what's interesting is that tech is targeting the Russian people, right, and separating Putin from them. And that hasn't happened quite as much as it's happening right now. Although I wonder, I wonder that's what explains some of the age gap in like a lot of the Russians who are protesting right now are

younger Russians who I'm sure are on social media all the time. And the older Russians are maybe home watching RT. Yeah, you know, it's like a Fox News problem. Yeah, no, I was going to say. That we happen to have in this country. I always joke about my mom, but you've got a population, older population who consumes endless propaganda. And eventually the repetition, you know, if anyone who studies propaganda, it's repetition, reinforcement, repetition reinforcement repetition reinforcement and the internet allows you to do that quite a bit but cable works fox news works especially on an elderly population that doesn't go

doesn't have other means of information young people are like no i have this over here the problem is a lot of them go into conspiracy theory. You know, they're all equal on these platforms. I want to talk a little bit more about your point that the internet is everyone talking to each other. I mean, in general, just beyond what's going on in Russia and Ukraine right now, you know, the running thesis of this show has been that social media is breaking our brains. To what extent do you think that's true? That's been my running thesis, as you know. Finally, people are listening to my theories from many years ago. I know, you've been on this for a while. How much do you think it is the fault of the platform

design versus human nature? Well, it's both, right? It's designed for human, bad parts of human nature. I think, you know, humans have been doing the same thing. It's not like, you know, some of us murder, some of us don't. We try to follow rules, some of us don't. Like, you know, humans have been doing the same thing. It's not like, you know, some of us murder, some of us don't. We try to follow rules, some of us don't. Like, you know, this is not new, fresh things that's happening. That's the argument these platforms have. You know, we're not unlike TV. I'm like, you're unlike a billboard. I can tell you that everyone sees a billboard. We see it in plain sight. We all react to it, right? It's not hidden. The message is right there. TV, same way. We all see broadcast it, right? It's not hidden. There's the messages right there. TV, same way. We all see broadcasts, right? This is like tiny little broadcasts going to each individual. Someone once told me it's a million lies going to a million heads all different. So that's different. The very first column I wrote for the New York Times, and I think it's probably my best

one, I should probably retire right after it, but was talking about that it weaponizes and amplifies. And I call them the arms dealers of the digital age. That's what they are. They give everyone lots of guns. And so when you put lots of guns in people's hands, people die, right? And so that was the way they've designed it.

The initial, like, let me take a person, Google, for example, Google search. You don't feel like that's a revolutionary tool at all because like it's fast. It goes for speed for sure. No it's fat, it goes for speed, for sure, no matter what, they all go for speed. It goes for accuracy, and it goes for context. And so when you search, I've used this example for the ADL, on Google, you find ADL, you don't find other things, you may if you keep looking, but you find the website for the ADL news stories about this

is the Anti-Defamation League. You find the right links, right? When you search it on YouTube, this is what happened to me. It was all anti-Semitic stuff immediately when you searched ADL. And so I remember calling the head of YouTube. I'm like, hey, I hear you're owned by this search service who's very accurate. And why am I getting this on your thing when I get the correct stuff? You know, it's switched from accuracy, context, and speed to speed, engagement, and virality. Now, when you design for those things, guess what you're going to get? All the crap. All the crap comes sliding down. You don't get the accurate things. You get the immediate things. And so Facebook is designed that way, right? And it also keeps people apart. It keeps, you know, so you don't see what's happening over here. So you don't know what's going on over here in these

other rooms kind of thing unless you get in them. And you also get dragged into rooms. I said this years ago, like my son was listening to something. And then he, I think Ben Shapiro just wanted to see what he was like. I was like, don't waste your time. But okay, fine. I let my kids do it. Give it a whirl. Whatever, give it a whirl. And then he got to other things.

And then other things, it was really, I was watching. I was like, whoa, that's, how did that happen? Of course, Ben Shapiro wrote something. Kara Swisher hates me. I'm like, well, I do. I hate your work. But I think you're allowed, whatever you are. I don't care.

I don't care. I don't even care anymore. But at the time, and he was like, she doesn't let, my son likes me. I'm like, no, he doesn't like you. He thinks you're a toad. But you know, I let him watch it. Like, I don't think,

of course he's going to write something now after this. So, because he always does. So I was interested in how it moved from thing to thing, because that's the way it went. That's the way the river flowed down to a toxic thing. And they've tried to work on those things. But it's designed for virality, engagement, and speed. And, you know, if you were talking about a car and drinking, you'd know what would happen every time, you know, kind of thing, if you think about it, if you put it in real terms.

And so that's the problem, is the design is meant to – the other thing it's meant to do is addict. You know, it's an addictive, they have addictive qualities. Everybody gets that. There's no question. So it's addictive. And now through the pandemic, it's necessary. You can't not be online, right? And it's also for entertainment. So it's addictive and necessary. And it's designed to engage you and enrage you. All the good uses of it, of which there are many and should be mostly, are out the window when you have that stuff. It's like having Twinkies in front of you and a plate of broccoli. I talked to Charlie Worzel about this, who writes for The Atlantic. And his point was, he's like's like you know i've been looking at

this for many years now and i just think that human beings shouldn't be connected on this scale and then you know i talked to alex damos who i know you've talked to many times um and alex sort of pushed back on me like he has with you at the same point where he's like people think that you can just tweak the algorithm and we're going to fix humanity's problems. And that's, it's not as easy as that. Even though if you identify some of this, this bad stuff, it's just really hard to design connection on this scale is basically the point that both of them made that is going to not cause the problems we're seeing now. What do you think about that? I think Alex is correct in that humans are the way they are, but there are things to mitigate that, right? There's always been mitigations in life, you know,

or else we'd have the purge all the time. Remember, we had the Wild West. It was wild. Most people got killed. Like, you know what I mean? Like, then we put in laws, and then we put in stop signs, and then mitigation. There's nothing wrong with mitigation

to pull back any kind of human impulse to murder, for example. Right? Like, literally. Like, when they make that argument, I'm like, well, we've got lots of laws in place, you know, and I think I compared it to having a meat factory and saying, some of this is going to kill you. Some of it's delicious. Like, but, you know, you like meat, like, you know, you humans. And so I was like, well, we have laws, and they're not perfect by any stretch of the imagination, but they create guardrails.

But I think Alex is correct that humans suck. Okay. But we tend to do something about it. We tend to try to stop them from doing that. And we tend to try to educate people and meet people, and they're doing none of that. They preside. I've used this metaphor so many times. They own a city, which the key part to me that Alex leaves out is they get all the money, right?

Right, of course. They make money from it, and not a little bit of money. They're the richest people on earth. Their companies are the most about it. The 10 top companies are tech companies, except for Saudi Aramco. I believe it changes, but it's mostly tech companies. The 10 top richest people, except for one or two people, I believe it changes, but it's mostly tech companies, the 10 top richest people, except for one or two people are all tech people, right?

Always have been for a while now, five years. So they have all the money, they get all the rent, and they don't provide stop signs, water, police, firemen. Talk about defund the police. They defunded the police a long time ago on online so they didn't fund it you know the psychology of these tech founders better than anyone do they just see themselves as misunderstood geniuses who are trying to save the world if the media would just stop attacking them that's what it feels like to me but i don't know no no i would you

know i just did a really great interview i recommend listening with brian chesky at our pivot conference i like brian and he understood he was like look if you get licked up and down all day eventually you're gonna think you're jesus right you know what i mean like i don't like to mix those metaphors but you know what i I'm saying. He talked a lot about this issue, about being, you know, told you're right. And you surround yourself with people who agree with you violently. Like, yes, that's, mm-hmm, that Kara Swisher, she's so mean. You know, that could be whatever. If you say it over and over again. And sometimes I am mean, but not all the time. And so they get around people who are like-minded people. I think that's one of the issues. Now, not all of them are not aware of this.

I would not say that. I would say, you know, I think Tim Cook will disagree with you about some things you might argue with him about, but he will talk to you about it. And he does not seem to pretend that it's not a problem. He sees the downsides and the dangers. Of course. Of course. He's an adult. You know what I mean?

He sees the problem. He was one of the first to identify. Mark Benioff is another one who runs Salesforce. He's the first person who compared it, in an interview I did with him, to cigarette companies, social media to cigarette companies, which I didn't think was quite right. But it was more like drug companies, I think, in some way, more than cigarettes. But it was interesting. And to see him turn on tech people was interesting. You know, the CEO of Stripe, a very powerful company.

Jack Dorsey is quite, I wouldn't say he's overly sensitive. I think, you know, the beard and the chanting thing is interesting, but that's so what? So what? So what? I don't care, you know? Just the way I don't care if Mark Zuckerberg hydrofoils, whatever the fuck that is.

Like people all were like, oh, look at that. I'm like, what do you care? Let him do it. It looks fun. We got enough things to criticize Mark Zuckerberg about. You know, I think Microsoft has come a long way from Bill Gates being the most obstreperous person on the planet to today. Satya Nadella is a very enlightened, I think, CEO in many ways. Sundar Pichai, though Google has some very big blind spots, certainly is reflective. Like,

they're not all like this. I think what we have is we've got Mark Zuckerberg, who feels like a robot, who happens to be a very earnest person, who literally is weighing over his head on big issues, right? And doesn't seem to want to give up the power that he has. He won't. He won't give up the power. He loves power. And so there's him. And then you have Elon Musk, who's like a walking, talking cartoon of a tech mogul, right? And whatever crazy thing he's going to pull off. Brilliant guy. Very funny. Completely deluded sometimes, and completely visionary other times. I mean, like I always say, someone's like, I can't believe I'm like, Thomas Edison was an asshole, FYI.

He just didn't have Twitter, right? If Thomas Edison had Twitter, he would have used it. Elon strikes me as someone who's like, you know what? I'm this smart. I can be an asshole. It feels like that's his sort of like, I'm a genius, so you can deal with me being an asshole. He's sometimes an asshole. I think he shouldn't do those dumb tweets. Like, okay, whatever.

Like, honestly. You could say that for like 90% of the people. He's really bad. He really is bad. And then he gets other people try to be mini-Elons and they suck at it kind of thing. But I think like he's an interesting character because a lot of our inventors were like him, right? Like the visionary, the people we consider, but we just didn't see it, right? By comparison, Steve Jobs looks like a statesman right if you and he

was he was a really interesting fellow probably got a lot more attacked for being heartless i thought he was full of heart i was my experience with him is you know he was a flawed person we expect these people to be gods that's the problem and they're people and they're flawed and they've got in steve jobs case he was adopted, had some anger towards his parents, his biological parents, had all kinds of, you know, problems, right? And we don't ever imagine that that's the case. Mark came from, you know, a nice suburb of Chappaqua, New York. He has a very nice family, by the way. And his father's a dentist, but definitely has some thing going on there, some power issues, right?

Anyone whose hero is Augustus Caesar, you have to go, hmm, interesting. You're sort of like, Augustus Caesar? Okay. All right. All right. No, that's true. It's true. The personalities of rich and powerful people can sometimes be as diverse as anyone else.

Absolutely. And Bezos is a whole other. There's good people and there's assholes. He's a whole other kitty cat. You know what I mean? Like here's a guy who also adopted interestingly. Larry Ellison also had problems with his mom and lived with his aunt, I think. I believe that's what happened.

I like to look at their backgrounds. I spent some time with Travis Kalanick's parents in their split-level home, very modest home in the suburbs of Loseles um in the deep suburbs of los angeles so they're all different i mean and and jeff is another visionary who also he's changed a lot but he's you know it's just we put so much stock in these human beings as the solver of problems that when so create problems, we wonder how that happened. It must be our fault when it's in fact theirs. Yeah. So I have admired your interview skills for a long time.

Thank you. I've been slightly terrified of them when I'm the target of the questioning. Oh, come on. It's just me and John arguing with each other. It was a day off. I always do it with love. You two sat there while we just are the gays arguing with each other. It makes me feel very safe. I always do it with love. You two sat there while we just are, the gays are with each other.

Makes you feel very safe. I am even in more awe of you now that I have an interview show of my own. Can you talk about your approach? Like, how do you get powerful people to go beyond talking points? One of the things, as I point out, that they're doing talking points out loud. You know, one of the things I do is interesting. I like broke no nonsense. I think I come across that way. I'm like, let's just stop. Like, let's go fast forward to where we want to talk about, or we can do this thing, and then I'll tell you you're an idiot, and then we'll move to

that. Like, I sort of am like, let's dispense with this. And someone, you work for Obama, right? You had a big job in Obama, right? So, you know, he was an interesting character to interview because, you know, presidents, no matter how you slice, I think a lot about where they're coming from. When you're a president, you talk and everybody listens, right? Nobody interrupts, right? You never get interrupted for like eight years. It must be fantastic. And I noticed one thing he did was he talked in big paragraphs, right? Which is what he does, yeah. Right. And it's a lot of words, like a word salad. That's how he writes.

He writes, he'll write a whole paragraph and use only semicolons. You can't find a period anyway. Exactly, and so I was like, wow, this guy talks in paragraph and he gets to say whatever he wants all the time and no one interrupts him. This is gonna be a problem.

And they cut my time for the interview that I had and I was like, kind of pissed. I'm like, oh great, talky and me are gonna have to have a problem here. I have five less minutes. And so it wasn't him in particular, but he's a particular paragraph talker. And I was trying to figure out what motivated him to actually answer a question. And I realized anger did a little bit. He doesn't like to get angry, right? He really tries to avoid it. And I thought, oh, I think I'll just irritate him into an answer. And so there

were two things I did is right before the interview, you know, you sit really close together. He's in a red chair. I said, listen, my time has been cut and you talk in paragraphs and it's exhausting to listen to. I said, so I'm going to interrupt you and it's probably not something you're used to because, you know, everyone bows down to you because you're president. But I'm going to interrupt you and I hope that doesn't bother you, but it's going to, just so you know. And so, and he looked at me, he said, I heard you were obnox. And I hope that doesn't bother you, but it's going to, just so you know. And he looked at me. He said, I heard you were obnoxious. I go, I am.

And then we began. It was like, but what it did was it got an earworm into his head, right? Like, oh, God, she thinks I'm talky, right? And he knows it's true. Because it is. I wasn't telling him a non-fact. And it's like telling someone, oh, you know, you touch your nose a lot or something or whatever, you know, whatever you happen to do. And it has to be true. And he answered much shorter,

one, which was great. And then the second thing was he was talking about at the time Apple was not giving up the phone stuff, wasn't doing the backdoor that James Comey wanted, encryption. And Obama had been on the Apple side when he was campaigning. And then he, you know, he became president. He's like, wait a minute, we need this. Then he saw all the classified info. Right, exactly. That's, I know that happens. That's what drove Dick Cheney to madness, right? Like, I've seen the unregulated, I'm like, some of that's lies, you know, Dick, just so you know. And it's what a group of people give you to make you do something. But okay.

So he then changed. And that's fine. That's fine. And so I said, well, you've changed. And he said, no, I haven't. And I'm like, no, no, you have. I said, I have an idea why you have because you've seen intelligence reports. And I bet it's scary. That world is scary. And he's like, I haven't changed my opinion at all. And I said, well, let me read you what you said on the campaign trail. And let me read you what you're saying now. And it irritated him. Like, you know what I mean? And I wasn't meaning to catch him. But it was an interesting thing where I actually had the thing. I'm like, you said it. I'm not trying to catch you. I'm just want to know, I actually was more interested in what happened, what occurred that made you change your mind, which I think was an

interesting line of questioning. He found it probably hostile. I don't know. But I think it elicited a really good answer from him. He then had a really good answer. And so sometimes with some people, you have to figure out what the motivating force is. One of the biggest lessons I learned in interviewing was not when you're a reporter, and I was a reporter reporter for a long time, I used to think people lie to me. What are they lying to me about in this statement that they're saying? And then I got a little more sophisticated and thought, what are they lying to themselves about to get through the day, right? What is their thing? So I do that. I think about that a lot. And then lastly, I point

out the obvious that everyone's talking about that reporters are too polite, either reporters are too polite, because they want to be their friends, or they want to hang out with them, or they're in awe of them or something like that. And I point out what everyone's talking about, like, and I say it out loud. And so, like, I did a really good interview with Jon Stewart yesterday. And so I'm like, so some people think this might not be relevant. And he's like, who? I go, come on, Jon, you've read all the things.

But then he talked about it, like trying to be relevant and leaving the thing. And it turned into a wonderful discussion. Same thing with the Joe Rogan thing. What happened what happened here like people are too scared to ask him like he's going to bite their head off i was like what did you actually say what did you actually mean what happened and then he took it apart and explained what happened great conversation right i think they're dying they're waiting for you to ask that question i just do it right at the top that's interesting like you know what i mean some people i don't even do this some people say like trump i i'm like i observe that you are you know don't even don't even give them the straw man of this no i don't i don't i just

come right at them i think you are a threat to humanity let's mark that prove me wrong like that kind of thing and sometimes this is the last thing i don't say anything like i often like you have to use pauses and because they're going to say something and i think one of my problems my first was a porter is jumping in when i was doing it at first the best moment i think i ever did in an interview was with zuckerberg actually i was talking about alex jones and i went in hot with that when i I'm like, this guy is a menace, and he's broken every one of your rules dozens of times. Why don't you kick him off? Why do you have the rules in the first place? I started arguing with him. I'm like, either don't have the rules, don't pretend you have the rules, but kick him off if he breaks

the rules, and don't go give me a speech about First Amendment. Why do you have the rules then? Like, don't have the rules. So we went back and forth and back and forth. And then he says, which was interesting, and I can't believe he did. I'm sure he was a media coach to do this, which was a mistake. And he says, let's move the topic to the Holocaust deniers. And I literally was like, oh, all right then. And he did it because he's Jewish. I know why he did it, because I'm sure some genius, I know who it was, actually someone I like very much, said, go to Holocaust, say I'm a Jew and I tolerate these things. That's what he was doing, right? Like, nobody likes Holocaust deniers, no matter what.

I mean, some people do, unfortunately. That's never your life raft, you know. No, exactly. But he did. And I was like, oh, God. Oh, you know, okay. All right. We'll go to Holocaust.

So I went, okay. All right. So he goes, like, for example, Holocaust deniers don't mean to lie.ust so i went okay all right so he goes like for example holocaust deniers don't mean to lie that's what he said right and i was like uh-huh and i could have gone you fucking idiot of course they do that's their job are you fucking kidding me and that was my instinct was like and i was trying to hide it behind my eyes like oh my god did he just say that and instead of saying you you fucking idiot, of course they do. I went, huh, interesting. I don't think that's true, but please go on. And I said, go on.

I said, please illuminate me of this particular, because I wanted people to hear him thinking out loud. And so he did and he stepped right into it, right? And so, of course, it became a huge problem and went all over the place, and then he had to backtrack and this and that. And what was really interesting about that is I got it, and the guy recording it got it. Both of us were like, what did he just do? There it is. And I wasn't trying to catch him, and I let him go on.

That's the thing. I wasn't doing a gotcha thing or making them say something that's revealing in one sentence i gave him so much space and so much ability and i do that with a lot of people i let them go on and i think if you let people talk that is the most illuminating thing because you get a real insight to their thinking versus anything else so not talking has worked out really well for me that would that would work on me because there is an element of like you start getting nervous at just the dead space. And then you've given your answer already. That's your messagey answer that you're supposed to give.

And then you're like, well, I got to keep talking. I got to fill the space because now I'm just getting anxious. I don't think you have that much to reveal, John, do you? No, no. Some secret crypt full of like cats or something. I don't think you have something to reveal. But some people do. And by the way, people want to tell the truth.

They do. Yeah, they do. Everyone's a Robert Durst. People want to unburden themselves at some point. You know, Mark Andreessen, who I also don't talk to anymore, once said it was Stockholm Syndrome with me. They don't know why they say things. They just have to.

That's funny. I know. Do you still want to run for mayor of San Francisco someday? No. syndrome with me that they don't know why they say things they just have to i don't know what it is i know that's right do you um you still want to run for mayor of san francisco someday no well maybe when i'm 70 i don't know i just had why did you why did you ever think about it what made you want it because i thought i complained a lot and i wasn't doing anything about it and i think you know i wasn't inspired by trump but you know i don't know there used to be citizen politicians right and professional politicians politicians drove me crazy. And I sat around like everyone else and that guy, that guy. And I thought, what am I doing?

This is ridiculous. Like, if I really care about my kids, at the time I had two, I should get in there and, like, try to solve problems. And so I think that was it. And San Francisco was, you could see where it was going with the homelessness and stuff. And I had points of view on how to solve it. I had interviewed a lot of people about it. I didn't think I could solve it. There was no, there's no solving that very terrible problem, really. But there's a way to mitigate the things and make it a livable city. And I remember thinking every single person on, on the, in the, in the stack, homeowners and renters and people who live, workers who live in the city,

the homeless themselves, the city workers, everybody is suffering, right? And we can't like decide it's homeless versus people. And what I did is I started walking around San Francisco and I thought, you start to hate people. You do. You're like, oh my God, you're ruining my beautiful city. And you start to dehumanize them very easily, right? And I remember doing that, and I thought, look at every one of these people like they're a little kid. Like, I have, you know, like, they came from somewhere. This wasn't where they wanted to end up. This is, you know, very few people are at their heart evil or bad or, you know what I mean?

Like, things happen to people. And I thought, I got to do something about it. I think that's what motivated the homelessness issue at the time. And it's worse now was really, um, it's, it was sad. It was, it was people living on the streets. It's bad for everybody, everybody, you know, and you can't, and people were setting up these homeowners versus home. I'm like, no, it's, that's not what it's. And that, that's what I was hating about. It was that it was a, it was a much bigger problem that everyone needed to give a little bit, like stone soup. And so I thought, you know, I'm going to get in here.

Because I also knew the tech people. And I could push, not push them around, but I could. Like, there was either too much niceness to them or not enough, you know, or too meanness. Like, it was either snarky. And I think I had my career where people do think I'm fair, right? Even if I'm tough, I'm fair. And I thought that I could carry that. Then I got married again and had two more children.

And so I had two children during the pandemic. And so it doesn't... I had one during the pandemic. Yeah, it's a lot. Child during the pandemic is a lot. It is. And so it was too much. I have a different life.

And I had to come move back here because of the pandemic. My older children were still in high school. One is still in high school. And so I wanted to be near them. And I want to move back to San Francisco. But we'll see. I think it's important for people to serve. I do.

Yeah, I do too. All right, so when the kids are all grown up and you're back in San Francisco, then maybe we get a run on. Yeah, I'll be like that 80-year-old mayor. Oh, isn't she? Look at the people running the country. It's're back in San Francisco, then maybe we get a run-up. Yeah, I'll be like that 80-year-old mayor. Oh, isn't she – Look at the people running the country. It's fine. I want them to say, she's a pistol. That mayor, she's 100 years old.

She's not taking any names. I don't give a – that would be my thing. I don't give a fuck. Don't give a fuck. I love that. That's a great slogan. Would you run the campaign? Do you want to run?

I'm in. No, same thing as you because i've thought about it many times in life and then once you have a family once you have a kid you're sort of like oh i'm gonna do this to them i'm gonna do this to my immediate family my extended family i like you know it's not even like a skeletons in your closet kind of thing it's like yeah things that you say that you mean to say yeah yeah right like i'm someone who's tweeted now for for five years six years right i have a podcast where i say all kinds of crazy shit i'd say i'm like i don't care that's that's why if you're 80 if you're 80 year old lesbian you can do that you're like yeah i said it so what yeah

see there you go fuck you last question that i'm sure our listeners want to know what does do to unplug and how often do you get to do it never never never unplug no unplug from the internet or yeah like like you have your phone's not with you you're just best relationship i ever had you know what i respect the hell out of that answer the world is in there all my friends everything's in there all the answers it's no why would i the answers. It's my thing. I love the – I was holding a blackberry, a small blackberry when my son was born. So let me just give you that piece of information and you should understand. Never.

I don't unplug. I don't stop. I can't. I can't. Now I have two more children. I got to make some bank. I got to make the cabbage now. So, you know.

I will say that is funny. I remember being at Cedars when Emily was giving birth and I was like holding my phone. I'm like, you know what? The service in this room is not great. And I do not know if I can refresh Twitter. I think that's a problem. Yes. Oh, my God.

I did the same. I just did it this time with Amanda. We had our second child, Solomon, a boy. We have Clara, who's a little girl. She's two. And I was about to interview Emily Radach Clara, who's a little girl. She's two. And I was about to interview Emily Radachowski, who's great,

wrote a really interesting book, a lot about digital stuff. And I was like, look at this about her. Look at her tweet. And Amanda's like, put the fucking phone down. And I was like,

in that voice? And I was like, oh my God, I suck, but I really want to pick it up. She's like, I hate Emily. And I'm like, no, you'd like her. She's like, put the phone down.

I appreciate an unapologetic addict. I love it. Thank you so much for joining Offline. Thank you so much. Offline is a Crooked Media production. It's written and hosted by me, John Favreau. It's produced by Andy Gardner Bernstein and Austin Fisher.

Andrew Chadwick is our audio editor. Kyle Seglin and Charlotte Landis sound engineered the show. Jordan Katz and Kenny Siegel take care of our music. Thanks to Tanya Somenator, Michael Martinez, Ari Schwartz, Madison Hallman, and Sandy Gerard for production support. And to our digital team, Elijah Cohn, Nar Melkonian, and Amelia Montooth, who film and share our episodes as videos every week.