Newsom's Senate Pick, SCOTUS Takes on Social Media, and Guest New York Times Pitchbot

Kara Swisher: Not all journalism is the same. Take The Guardian. Our coverage has something unique. Fierce independence. Nobody owns us or tells us what we can and can't say. So we're free to report the whole picture. We connect what's happening in Washington to the rest of the globe. Expose corruption wherever we find it. And give fresh perspective on everything. From wellness and soccer to culture, the climate and more. Read, watch and listen to The Guardian for free at theguardian.com.

Scott Galloway: AI agents are getting pretty impressive. You might not even realize you're listening to one right now. We work 24-7 to resolve customer inquiries. No hold music, no canned answers, no frustration. Visit sierra.ai to learn more.

Kara Swisher: Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast Network. I'm Kara Swisher, and I'm in California.

Scott Galloway: I'm Scott Galloway, and I'm traumatized.

Kara Swisher: Why? Why?

Scott Galloway: Over the weekend, I realized this is old news. I watched a Code interview with Linda Yaccarino.

Kara Swisher: Oh, yeah. Sorry about that.

Scott Galloway: I'm not exaggerating, Kara. I think that was probably the worst performance by a CEO I've seen in a decade.

Kara Swisher: Tell me.

Scott Galloway: I will tell you. We've talked about how it went down. I'll tell you how it went down.

Kara Swisher: Go ahead.

Scott Galloway: I just feel like she got up there and seemed detached, delusional, angry. It's really difficult to come across as insecure and aloof at the same time. I thought it just struck me as someone who was so out of their depth.

Kara Swisher: Yeah.

Scott Galloway: It was just... dumpster fire is the... I'm not exaggerating. Like 10 minutes into it, I'm like, this is... I'm uncomfortable watching this on YouTube.

Kara Swisher: Yeah, try being in the room. Try being in the room. It was.

Scott Galloway: What was the mood like in the room?

Kara Swisher: It was so weird. She lost the crowd right away. You know, I got blamed for ambushing her. I don't know if you heard that part. What happened was, Mary Barra just couldn't come. Yoel was actually the third person I asked. I thought he'd be interesting. I've done an interview with him previously, but not before he got called a pedophile by Elon Musk on Twitter, or insinuated that he was a pedophile. It caused him all kinds of havoc, including selling his house, death threats. So I was going to always have him back. And he happened to be in LA. So we had him down. We told Linda that morning, and she had plenty of time to prepare. He also didn't say anything on stage that was anything different than he'd said before, including in the New York Times. He's such an articulate and kind person. And he was quite magnanimous to Linda because she wasn't there. And for some reason, it really tweaked her, I guess. Not our fault at all, I think. And so I don't know what happened to her because she's always been a very calm, articulate person at events I've seen her at and not so easily shaken.

Scott Galloway: Well, that person did not show up. When she was asked what she thought of Yoel's comments, her response was, "Well, he worked for Twitter. I work for X."

Kara Swisher: Yeah.

Scott Galloway: I mean, that is the most... And then when asked about the accusations of anti-Semitism and the fact that Elon is going after one of 60 companies that signed this letter or organizations, I should say, she said, "Well, we're a free speech platform." And it was like, well, let me get this straight. This guy is threatening to sue someone who exercised their rights to free speech, but you're a free speech platform? I mean, the whole thing was like a series of awkward, cringy inconsistencies. Not one piece of data. It was just... anyways, let's move on. I don't even like...

Kara Swisher: We will. I just want to say Julia Boorstin did a very good job with that. Obviously, the interview changed. She did a good job. We're going to see what will happen. I've asked her to come on the podcast, my podcast. So we'll see.

Scott Galloway: Good luck with that. She might. That's a baller move. Come and explain yourself.

Kara Swisher: I think she knows. But yeah, I asked. I asked. Why not? Anyway, it put a little zip into Code, I'd say. But it was a very good time. But you're still in the Bay Area?

Scott Galloway: I am in Los Angeles for four seconds.

Kara Swisher: In LA. Wow. But there's a lot to talk about. We're at the Supreme Court taking on social media and Matt Gaetz taking on Kevin McCarthy. And we'll speak to a friend of Pivot. I'm so excited to talk to this guy, one of the funniest people on social media, New York Times Pitchbot. First, Laphonza Butler, speaking of California, will be sworn in Wednesday to the late Senator Dianne Feinstein's seat. California Governor Gavin Newsom moved quickly to name the appointment after the Congress narrowly averted a government shutdown. She runs Emily's List, a group that works to get Democratic women elected. I know her. She's the first Black lesbian to openly serve in the U.S. Senate. Really incredible person. Newsom didn't place any restrictions on whether Butler could run for the seat in 2024. The race to fill it is already packed with representatives Barbara Lee, Adam Schiff, and Katie Porter all running. Any thoughts at all?

Scott Galloway: I think it's great. She seems... I think it was a great pick. I think Governor Newsom did her a disservice by announcing he was going to pick a Black woman. Why would he announce that I'm limiting myself to 6% of the population? I think it's an insult to her. Why didn't he just... anyways, good for her. I think it's great. We need more representation. And she seems like a thoughtful person. And yeah, I'm super impressed. It'll be interesting to see if she decides to run. I don't think she will. She's sort of a background player in politics in a lot of ways.

Kara Swisher: I agree with you. He shouldn't have said anything. But lots of politicians do this. I think Biden certainly did in the last election.

Scott Galloway: I know. But it's identity. We're susceptible on the left of... and this is a fair criticism... that we're angry that the right is obsessed with race, but we're obsessed with race when we start saying, "Okay, she's a very talented person who has earned this appointment." Why would they limit it to attributes that people have no control over, which is our criticism of the right?

Kara Swisher: I get it. I do think it's okay to indicate that, wow, we really need to have a more diverse... I think that's okay. But putting... I would agree with you on this one, I have to say. That said, you can still indicate that we want to have a more diverse Senate. You can say that. I don't like... look at the Senate. Look at the old white man Senate. "I'm going to pick somebody outstanding. Oh, and what do you know? I did pick someone outstanding. Isn't it great? She also happens to be Black and a member of the..." anyway.

Scott Galloway: Yeah. I think we open ourselves to criticism of identity politics.

Kara Swisher: All right. Thanks, Bill Maher.

Scott Galloway: Thanks, Bill Maher, for that.

Kara Swisher: Anyway, speaking of Bill Maher.

Scott Galloway: By the way, did you see his show?

Kara Swisher: No.

Scott Galloway: Did you see his show?

Kara Swisher: No. I'm totally parodying Bill Maher. I know you are.

Scott Galloway: They pulled together an amazing show in two days. Sam Harris, kind of my role model and spiritual guru, was on. The writing was outstanding. They interviewed Governor DeSantis, and I thought he was civil, yet he pushed back on him. I thought it was a fantastic show.

Kara Swisher: All right. Okay. This is where we're going. Okay. He's fine. He's fine.

Scott Galloway: Don't mock me. Don't shame me.

Kara Swisher: I will. I just... he does the same old, speaking of same old, same old. It's like, "Wow, wow, wow. This is the left. This is the left. Same old, same old fearless." Oh, stop it. He just... all he does is attack the left. He really does. And he used to attack religion and the right. And I'd like a little...

Scott Galloway: He was pretty hard on DeSantis.

Kara Swisher: I get it. But I liked a little bit of variance with him. That's all. Just a little open mind.

Scott Galloway: Okay. On a scale of one to 10, where do you think he is on the political spectrum? One being AOC or Elizabeth Warren and 10 being Ted Cruz. Where do you think he is?

Kara Swisher: Oh, come on. And I think he just is a contrarian by nature. And that's it. That's his thing, like a lot of people. And I just would like to know... I don't feel ever good when I watch it. I'm never getting on this show again.

Scott Galloway: That's fine.

Kara Swisher: I get a little tired of it. That's all. I just think there's a lot of people like that. And I'd rather...

Scott Galloway: There really aren't. He's singular. Who else is like him?

Kara Swisher: Tongue bath.

Scott Galloway: Who else is like him?

Kara Swisher: Lots of comics. Tons of comics. Tons. Tons of them. I don't know why every single comic, but all the comics are different.

Scott Galloway: I agree. Some of them, like Jimmy Kimmel, Fallon, Colbert, Oliver. Oliver is the one I like.

Kara Swisher: Come on. I like Oliver.

Scott Galloway: They're all total liberals. They're all progressive.

Kara Swisher: No, not. Oliver is...

Scott Galloway: Oh, my God. He slaps real hard at the left, too. He does. He does. But he's not just a...

Kara Swisher: Deep blue. Bill Maher's gotten so whiny. I'm sorry. I'm just like, stop, stop, stop.

Scott Galloway: I'm sorry. We're going to have to disagree on this one. I like John Oliver. You like Bill Maher. We're just going to have to keep doing this show together and just agree to disagree on someone like that.

Kara Swisher: Anyway, it's not just Bill Maher. The rest of late night TV returns this week following the end of the WGA strike. Jimmy Kimmel, Jimmy Fallon, Stephen Colbert, John Oliver, and Seth Meyers are pulling out all the stops with star-studded guest rosters, including Arnold Schwarzenegger, Matthew McConaughey, and more. But peak TV is over, according to the Wall Street Journal. The article over the weekend predicted future hurdles for the industry, including show cancellations and fewer new productions while streamers worked to cut spending. One veteran TV producer predicted the number of scripted shows could fall by one third in the next few years. Several of my friends who were writers got their contracts not extended and cut. And I think Universal cut all of them, all their outstanding contracts. It's sort of like a bloodbath out here in terms of, they keep people on contract. Now they're just not going to do it. Some who had popular shows got to stay. But for the most part, they really cleaned house, which they did before, but not to this extent, I think, from what I understand.

Scott Galloway: Yeah, well, we said this a couple of years ago. I remember just looking at the amount of money that was being spent on streaming and how much money Hollywood or Netflix and everyone trying to chase Netflix was spending to bring you Euphoria and Bridgerton. And you could just look at... I mean, at one point, I think I did the math once for every house that had streaming. These companies were spending $2,200 a year to deliver that content to you. And this isn't the cost of technology or cable, just the cost of the content they were delivering. And it was totally unsustainable. So distinct to the dynamics around the strike or the Writers Guild, the reality is this is an industry that overspent trying to follow Netflix who was essentially established a strategy of growth that the markets loved and they could pull away from everybody else. Everybody followed them. And now we're going to have massive consolidation, but it's still going to be unbelievable selection. It just got way out. The industry just got way out over its skis. It's a place that I think is really going to get hurt, though, and I'm super curious to see what the ratings are. My thesis has been that late-night TV that's kind of linear because you see the day's news and they're very charming personalities. I think it's a part of some people's kind of bedtime routine. And I wonder if the strike went on long enough such that people found substitutes and replaced those habits with something else and it never recovers.

Kara Swisher: Yeah, there's too many of them and they're too many the same. In that way, they're too... like that's why Greg Gutfeld did very well. He was an alternative. And that's why Bill Maher does well. It's an alternative. And so I think people, you don't need six of the same people or five or whatever it is. Five, I guess it is. So it's difficult. I think, let me read from Matt Belloni on this one, because I think he's completely right. "I know a lot of writers and reps who quietly breathed a sigh of relief when the studios opted to suspend rather than terminate their overall deals during WGA strikes. Months of zero pay would hurt, of course, but once the strike settled and the pain was over and the time off, the studio checks would just be added to the end of their deals. So yeah, welcome to post-strike Hollywood. For most TV writers under contract, the studios have flushed those assumptions down the toilet. A week after the WGA strike ended, hundreds of reinstated writers have been notified their deals will not be extended. And when many of these deals expire, they will not be renewed. It's bad. Texting with agents and lawyers this week, and the estimates are anywhere between 60-80% of suspended writer deals will have been impacted. One major employer, Universal Studio Group, extended none of its suspended writers." So they got stuff in the deal, but this... I mean, this is what we've been talking about and why people are angry at you and me, well, me by extension for saying this is problematic.

Scott Galloway: For associating with me?

Kara Swisher: Yeah. Guilt by association?

Scott Galloway: You know, I keep reiterating what the Diller interview said, which is tech is the problem, as you have too. But this is what the studios do when they have economic difficulties. They cut and they don't need all those people.

Kara Swisher: Yeah, like it's going to be... distinct to the strike, it's going to be a smaller industry.

Scott Galloway: What I suss out of trying to parse through all the exceptional terms that the union garnered for its workers is that the best are going to get more money. And that's just a natural function of the economy. But there's going to be far fewer writers making a living.

Kara Swisher: Yeah. Yeah. It's amazing how they just cut everybody, but that makes sense. They'll cut them and then they'll bring back the ones that... they're just cleaning house. That's what they're doing. That's what one told me. Anyway, speaking of cleaning house, let's get to our first big story. A government shutdown is not happening. A few hours before the shutdown deadline on Saturday, the House passed a short-term funding measure to keep the government open through November. What a way to run a government. It's so ridiculous. But to get that measure passed, McCarthy had to work with the Democrats, which did not make his nemesis, Congressman Matt Gaetz, happy. Let's listen to what Gaetz told Jake Tapper on Sunday. And this was an excellent interview by Jake, by the way. "I do intend to file a motion to vacate against Speaker McCarthy this week. I think we need to rip off the Band-Aid. I think we need to move on with new leadership that can be trustworthy." McCarthy, for his part, is saying, bring it on. This shutdown seemed inevitable. Well, he finally blinked and had to talk to the Democrats. Now his fate lies in the hands of Democrats. So both of them are going to need the support of Democrats to make their plans work. AOC told CNN she would absolutely vote to oust McCarthy but also noted, "I don't think we give up votes for free." So what are we going to get for this? It's a really unusual situation.

Scott Galloway: Yeah. So we talked about this in our predictions late last week. We said that either Linda or Speaker McCarthy wouldn't survive because they're not demonstrating any leadership. And to be fair, I think Speaker McCarthy did demonstrate leadership at the cost of his job. But he said, "I'm going to do what I think is right." And he passed, granted, they're just kicking the can down the road. But I think in a weird way, it might be an opportunity if the Democrats say, "Fine, we'll support you, but we need an explicit guarantee." Senator Bennet, as always, does yeoman's work here and made sure that senators from both sides of the aisle and President Biden committed. They said, "Be clear, we will continue to ensure that Ukraine receives proper funding to push back on Putin." But I wonder, this might be actually an opportunity to have something resembling bipartisanship. I like the idea of the far left and the far right being bested by... I mean, he's supposed to be Speaker of the House, right? So is this an opportunity maybe for them to come together and say, "Okay, boss, you now are a speaker for 90% of this party and 10 or 20% of us, and we'll let you keep your job." I don't know. I just think he did the right thing.

Kara Swisher: I don't know. He might lose his job. I don't want to get a choice, right? I think he could have let it go down and then they would have dumped him anyway. It's really interesting that everything is in the hands of Hakeem Jeffries, right? Where he decides to move the... the progressive group aside, it's not going to be enough votes. It's really... Nancy Pelosi is very good at whipping everybody into shape and voting the way they want. And now there's all these people that are freelancing it, right? As the way it is in politics now, just like Matt Gaetz is sort of freelancing. What do people think is going to happen? I just don't have a feel for this. I don't know. I don't know what the Democrats will get. I mean, obviously, there's all kinds of horse trading going on, but I assume Ukraine, of course... there's a growing movement against Ukraine funding, right? It's only going to get stronger as it goes on. That's just inevitable, too. And I don't know what they could want. What could they want? The Dems in the House could help McCarthy get rid of this "motion to vacate" thing from one person and make it 10, for example, so that McCarthy's not always... Matt Gaetz can keep doing this every single day, call for a motion to vacate or not every day. They've got to vote on it. They have 48 hours. So he could do this 10 or 12 times like they did in that last ridiculous thing. I mean, the whole thing is just these people are really spending a lot of time on procedure, which is really weird. Again, a bizarre moment in the shutdown was New York Congressman Jamaal Bowman pulling the fire alarm in the congressional office building ahead of the vote. He said he wasn't trying to delay the vote, but activated the fire alarm mistakenly thinking it would open the door. He was a principal. So I think maybe that's not true. Kevin McCarthy and others, of course, have made the January 6th comparisons, which are ridiculous. But he shouldn't have pulled it. This whole thing is just, I don't know.

Scott Galloway: I was thinking about this. You don't pull fire alarms. You just don't. And he should be punished, but the punishment should match the crime. And this isn't breaking in and trying to track down the vice president with a noose. But I don't think there's anything around it. That was wrong. He might go down in history as having done the right thing, but he was wrong to do that. I mean, you've got to take these things seriously when there's a fire alarm. And if people pull them when there isn't a fire, you just reduce the likelihood people are going to take them seriously anyways. Did that ever happen in your school?

Kara Swisher: I don't think anyone ever did that when I was in school. Everyone sort of knew not to. Even the jerkiest jerk didn't do that.

Scott Galloway: Oh, no. We had what was it called... a tardy alert where they would say... no, it was called... it was hilarious. It was called a tardy sweep. And someone would come over... I went to a big public school. Someone would come over the loudspeaker and say, "This is a tardy sweep." And if you weren't at your class, you got rounded up and shuttled down to the cafeteria. And you had to sign up. And if you got more than two... And I'm not exaggerating. For those of us who had never been in a tardy sweep before, it was like an air raid alarm going off. We're diving into windows into home economics and diving into strange classes. "Will you hide me? Will you hide me?"

Kara Swisher: Huh. Interesting. Anyway, Jamaal, mistake. Stupid. Don't be a child. You were a principal. I don't know where this is going. As usual, it just makes Congress seem idiotic is all I can tell you. That's all it does.

Scott Galloway: I don't know what else to say. It's worse for the Republicans.

Kara Swisher: Yeah.

Scott Galloway: I think they're going to catch more shrapnel here for this.

Kara Swisher: Yeah. I don't know. I think most people look at this and think, "What a fucking mess these people are." That's what most regular people are like. I don't know. Let's go on a quick break. We come back. How the Supreme Court could change social media as we know it. And we'll speak to a friend of Pivot, New York Times Pitchbot.

[Ad Break]

Kara Swisher: Scott, we're back. The Supreme Court's new term gets underway and recent additions to the docket include two cases that could have major implications for social media and content moderation. At the center of these cases are laws in Florida and Texas that limit the ability of big tech companies, including Meta, X, TikTok, among others, to kick users off their platforms or remove individual posts. The lobbying group that represents the companies say the laws violate the First Amendment, while the states argue they're allowed to regulate to make sure all users have equal access. So how important are these cases? The Atlantic quotes a law professor who says, "I think this is, without exaggeration, the most important Supreme Court case ever when it comes to the internet." I do too. This is like... I cannot believe it's at the Supreme Court that it's not a First Amendment issue for these companies, that they're allowed First Amendment rights. These Texas and Florida laws came after the 2020 election on January 6th when Donald Trump got banned from several platforms. Lower courts have issued conflicting opinions, which is why the Supreme Court wanted to weigh in, presumably. Thoughts?

Scott Galloway: I see the two as bifurcated. I can understand the concern around government putting pressure on a media company to take down, which is essentially censorship. But at the same time, I don't understand how you can tell a private company what they can and cannot say. If Facebook, if Meta or Google decide to take down content, that's their right. That's also free speech. So I bifurcate the two. What do you think?

Kara Swisher: Well, I don't think the government's involved in this. It's the companies making this. There's a whole other case where the government is speaking, talking about whether it's vaccine information. And that's another case, I think, I believe. And what's really problematic here is, as I've always said, these are private companies that have First Amendment rights, right? You don't have any right to be on Twitter. You just don't. You just don't. And if they don't want you on there... and we can howl when Elon does it, which we do, or when the former management did it, the right howled when the former management did it. But I don't think anyone has any right to be on these things and they can kick off whoever they want. I just don't even know why it's that the states... and it says "government shall make no law." So states can't make a law. They do when you go to restaurants, I guess. I'm not a legal person, but I think they have to hold for the companies. Just like they did in the last term. There was the last term the companies won a lot of this stuff around terrorism, if you remember. They're not going to be heard till next year. And by the time the court rules, we could be well into the election season. Both laws are currently blocked from going into effect until there's a ruling. I'm sure there's a chilling effect on some of these companies. I feel this is a slam dunk for the companies, but maybe I'm wrong.

Scott Galloway: I agree. What are we engaging in censorship because we don't bring on every viewpoint? I just don't... these companies have the right to, if someone is trying to radicalize young men on YouTube, they have the right to take that content down. And the question is whether or not the First Amendment issue is whether or not the government has the right to influence what they're doing. Again, I think it all comes back to better laws that put these media companies on level ground as other media companies.

Kara Swisher: Yeah. I don't know why you get equal access. That's the part I don't get. I mean, there are laws around television, but that's a government... well, I guess the internet is a government. But I don't know. Why would you get equal access to private things? I just don't know. When I was locked out of Twitter, I just said, I went on Threads and I said, "I think that's the right." Now, granted, it might be hypocritical to be screaming free speech and to have... and by the way, I now think I wasn't... I don't think it was anything that Machiavellian, but I think it was just incompetence.

Scott Galloway: Yes.

Kara Swisher: But that's their right. I don't have a birthright or a natural constitutional right to be accepted on a platform. I don't... anyways.

Scott Galloway: I wonder what Elon Musk... because he's all these... I mean, that whole genre of people, they're like "free speech, free speech," even though they break it all the time, how they're going to win. And I guess they will be for doing whatever the hell they want, right? Presumably.

Kara Swisher: Yeah, they're going to want the most latitude as possible because, I mean, they did kick Kanye off. There's just certain things he can't say. And they make a reasoned assessment over what will move the stock price up or the value of our company up. And as we have seen, essentially, the companies that have the strongest moderation, there's a direct correlation between moderation and shareholder growth. If you want the Wild West, go to 4chan or 8chan and just see how much you like total free speech. People don't... the notion of free speech or my understanding of the First Amendment is that government shall pass no law that inhibits a company in terms of the content. So pass no law that inhibits speech. So one side of the argument makes sense, but companies can do what they want with the exception of slander and defamation. If they purposely distribute and highlight information they know to be wrong that creates economic or physical harm to somebody or some company, they are liable, except if you're big tech.

Scott Galloway: Yeah. I think the other case where the government's speaking to social media, there's another case around this, is more problematic. The government communicating danger or terrorism things, I think there might be a real chilling effect on that. I heard from a lot of academics this week, Yoel being one of them in this interview I did with him, about the chilling effect of these companies suing, being sued because of decision, but because of misinformation research for one. And secondly, the chilling effect on companies of these cases, one of which is going to eventually rise to the Supreme Court, I think, which is about whether these companies and government can talk at all, right?

Kara Swisher: If they can have, like government can have any just normal discussions around safety with these companies. And that's, you know, this is going to go on for a while. This is a big hobby horse of the right, for sure. We'll see. It'll be interesting to see. This is, I can't imagine this. Given last year's rulings, I think they'll rule with the companies. I don't know where they wouldn't do it. Well, we'll see. These are really important. Just remember, The Supreme Court matters a great deal in where this is all going. We talk a big game, but unless Congress steps in and actually does their job, which doesn't seem like they're either pulling alarms or fighting their leaders or whatever, nothing's going to happen here.

Kara Swisher: But let's move on. Speaking of which, someone who does have great speech. Let's bring in our friend of Pivot. It's Doug Jay, also known as the New York Times Pitchbot. He remains anonymous. He's the person behind one of my favorite accounts on social media. Makes me laugh all the time. Every time I read it, New York Times Pitchbot. Every day, the Pitchbot mines the news to craft headlines and hot takes that are hilarious and ridiculous, and it could be possibly New York Times stories. Sorry, New York Times, but they're funny.

Kara Swisher: Some gems include: "Is the Travis Kelsey Taylor Swift relationship Biden's Katrina?" "The iPhone 15 will move away from the lightning connector. Here's why that's bad news for Joe Biden." "We wanted to understand how Elon Musk's ex might become half of the global financial system, so we talked to four NFT collectors at a Smashburger in San Mateo." "Whether it's Chuck Schumer relaxing the Senate dress code to appease John Fetterman or Lauren Boebert groping her date at a play, members of Congress on both sides of the aisle are preoccupied with what's going on inside men's shorts."

Kara Swisher: The Pitchbot prefers to keep his identity under wraps, so we'll be referring to him today by his alias, Doug Jay. Welcome, Doug Jay. How are you doing?

Doug Jay: Great. It's great to be here.

Kara Swisher: I love what you do. I love what you do. So I'd love for you to tell me how you decided to do this. It's so on point with things that could actually happen. Is it just that you wanted to do a parody, or what?

Doug Jay: So I guess I sort of started doing it because the pandemic happened and I didn't have time to write. I used to write for a blog called Balloon Juice, but I didn't have time. I have two kids and, well, actually, I only had one kid when it began. And I didn't have time to sit in front of the computer and write. So I was like, I want to do something fun on Twitter. And I really liked the Federalist Pitchbot and Reason Pitchbot. And so I decided to do a Pitchbot. So I did it for about a week. And then a friend of mine who's actually a conservative journalist—I think he was working at the Weekly Standard at the time—emailed me, DMed me and said, "This is great. You got to stick with this. You were born to do this." And so that's how I really got into it.

Doug Jay: One thing about it is that it's a mixture of things. I'm not really anti-New York Times necessarily. So sometimes they're mean, but in general, it's just trying to sort of capture a little bit of what I think is this sort of journalistic zeitgeist that goes on at a lot of elite media publications.

Kara Swisher: Talk about what that is from your perspective. Let me read one of your most popular posts from 2021 during the U.S. withdrawal from Afghanistan: "We wanted to understand what's happening in Afghanistan. So we talked to three unvaccinated Trump supporters at an Arby's in Harrisburg."

Doug Jay: Yeah, so I really don't like this thing they call the "diner safaris," where they drop into the middle of nowhere and they talk to people. And inevitably, no matter where they go, the people are all Trump supporters or, at the very least, disillusioned Democrats or something like that. And also, they almost never have someone say something intelligent in these interviews. A friend of mine who's from South Dakota told me I'm wrong about this, but my belief is that if you walked into just about anywhere with 20 or 30 people, one of them would actually be well-informed and have something intelligent to say about whatever the issue is. But I feel like they have a laser-like focus on whoever is going to say the most kind of dumb and pro-Trump thing that they can find. And I think it perpetuates a lot of stereotypes.

Kara Swisher: Yeah, I agree with you. That's why it's funny, because it's like, "Oh, I read that story." Right, I read that story that they did. But is it the New York—you said it's not the New York Times. You're talking about media in general for parody.

Doug Jay: It's more all the elite media. I've read the New York Times my entire life, so I sort of know the way that they talk. But when I started doing this, I started to realize that the Atlantic and a lot of Substack people are much worse than the New York Times. Much more sort of like the Atlantic's obsession with campus free speech. The New York Times is bad about it too, but they're truly, truly obsessed with it. So I sort of branched off a little bit into other types of elite media and also sort of well-known Substackers like Matt Yglesias. And I guess Jonathan Chait isn't technically a Substacker, but he's a Substacker to me.

Kara Swisher: Life has imitated art several times over the years where one of your headlines is almost verbatim an actual headline in the Times or another place, which is funny and frightening.

Doug Jay: Yeah, so I get a lot. It's a very, very interactive thing. Almost everything to do with the breaking stories is interactive. I go into my DMs or mentions and people are like, "Hey, this story's breaking." And then I always think to myself, as soon as it breaks, I've got to think of the really dumb take on it and get it up there fast so that I get it up before it actually appears in print. Because three or four times I've done it, and then people said, "Oh, you missed it an hour ago. The New York Times already ran that headline." In fact, more often than not, that's what happens with my really dumb takes. If I'm slow at all, there will already be someone saying it.

Scott Galloway: Nice to meet you, Doug Jay.

Doug Jay: Nice to meet you.

Scott Galloway: What is your process? Will you come up with some ideas and then run them through a kitchen cabinet of friends or let them ruminate? And also, do you use generative AI to come up with ideas or screen them? What's your creative process?

Doug Jay: So the creative process is I definitely scan my replies and my DMs for ideas from people. But a lot of it is this, and this is why I feel like the AI angle on it is a good angle: I have about maybe 20 templates for headlines. There are some that are more popular than others. There are like six or seven that are my real go-tos. And when something happens that I think is worth commenting on, I immediately just go through in my head all 20 of them. I don't always get through 20. Usually one of the first six or seven works. I go through all my templates and shove it into a template. So it is very AI-ish in that occasionally I do a really freeform one, but for the most part, I have a very, very set template for it, which I think also is how the New York Times does its headlines. I think it's kind of worked because it's a little bit AI-ish and it's called a Pitchbot, but it also really does capture what sounding like them is, I think.

Scott Galloway: Is this just pure consumption? Is this just for joy? Is it part of a larger strategy to become a media personality and monetize it? Is it to influence culture? Or is it just a kick in the ass? What is the reward here?

Doug Jay: I would say it began 100% as just a kick in the ass. And then I started to think, and people would say to me, people I really respected in media said, "Oh, I really like what you're doing." And I think they actually read it. I think it actually makes a difference. It sort of prods people in elite media not to be so... and so I decided, okay, well, now I've got to be a little bit more serious about it. I don't really like dark stories very much. After there's a mass shooting or something, part of me is like, "Oh, God, I just want to log off for a little while." And then I think, but this is where the media, in some ways, is at its very worst. And so I actually feel like I've got to go on there and make fun of these terrible things, because they really are doing awful things that I think undermine attempts at gun control, for example.

Kara Swisher: I would agree. But some stories, obviously, like Lauren Boebert behaving badly at Beetlejuice or David Brooks posting about food prices in New York, they're just slam dunks, correct?

Doug Jay: Yeah, a lot of it is really just for fun. Especially if some story comes up and I'm getting a million people DMing me and my friends are texting me, my wife is talking to me about it, I think, "Well, this is just going to be fun for the next 20 minutes. I'll just sit around and write silly stuff about David Brooks."

Doug Jay: Although I do also think with the Lauren Boebert one, I originally almost didn't want to do it because I don't really care about Lauren Boebert's personal life. It's not that bad, whatever she did. The David Brooks one I feel differently about, because I think it does feed into this really annoying thing of, "Oh, everything's bad news for Biden and inflation so bad." And if you look at how Brooks, quote unquote, apologized for it, he turned around and said, "Well, I know I'm a rich guy drinking expensive bourbon, but sticker shock is how regular Americans feel when they see X. And I'm capturing that in the tweet." And I knew that's what he was doing all along. So yeah, some of it like that, it's a slam dunk. But at the same time, it really is just the kind of thing that the media does that they really shouldn't do, in my opinion.

Kara Swisher: Yeah, I would agree. You have frequent targets that you use. Maureen Dowd comes up, Elon Musk, and Glenn Greenwald. Between Glenn Greenwald and Maureen Dowd, you really do cover the thing. Do you have any personal favorites, templates that are your favorites?

Doug Jay: So I kind of like—I love doing the Maureen Dowd ones. The thing with Maureen Dowd is that this is a very stereotypical thing. She really, really reminds me of a lot of people in my mom's family. My mom's from a really big Irish family. So that one is just fun. And those things are in my head anyway. They've been in my head my whole life. So I like doing those the best.

Doug Jay: I really like doing the "In this Ohio town, it was a tradition" one. Those are a lot of fun to do. "Times have been tough in this Ohio town ever since the woke mob shut down the old Choco Taco factory." That's probably my favorite template. But it's very hard. They're too hard to do. I can almost never do one properly. That and I like the Indiana Diner one a lot, too. "In this Indiana Diner, everyone has three questions: Is the quarry hiring? How's the breaded tenderloin? And then a third question." I like that one because someone from Indiana just wrote it for me. Then I started to use it.

Scott Galloway: What accounts do you admire?

Doug Jay: Probably my all-time favorite account—he's not really on Twitter anymore—is Oliver Willis. I think he just really gets politics in a way that hardly anybody else does. I really like Atreus a lot. I really like Gloria Ryan a lot. She can be very, very funny. And a lot of the things I liked are gone. Federalist Pitchbot is gone. Reason Pitchbot is gone. And one of the ones I really, really liked was the fake Professor Jeff Jarvis account, which I feel bad liking because I actually liked Jeff Jarvis too. The guy who did it started making fun of Jeff Jarvis, and then he realized actually Jeff Jarvis isn't really that bad. There are much worse people. So it sort of branched off into an all-purpose making fun of stupid tech stuff. I don't think that guy's very active anymore. But that was one of my all-time favorites.

Scott Galloway: What happens to that? How active do you stay? With Elon's purchase of Twitter last year, the platform is not what it used to be. Last week, Scott called it "the sewage system of a sewer." Is it still an effective place to do this for you? You're still posting actively. Do you think elsewhere is important, or is it just that these things have a lifespan?

Doug Jay: I'm really ambivalent about staying on Twitter. I checked out Blue Sky, and I checked out Threads, and I didn't really like them as much, unfortunately. I don't really mind Elon having all the fake followers and making everybody see his tweets and stuff. I kind of think it's funny, to be honest with you. A lot of the Elon stuff is just funny to me. It almost makes it better. But the stuff with the anti-Semitism is starting to really disturb me. And part of me thinks, I've got to get off. We all have to get off of here. We're sort of just promoting this sort of proto-Nazi movement. I hope I'm wrong, but the anti-Semitism—I mean, there's the racism and the misogyny, too. I don't know why the anti-Semitism seems even a little scarier to me right now.

Kara Swisher: Right. And when you think about that, when you're sort of making fun of—and Elon's very easy to make fun of—is there anybody that's really pushed back at you among these? Glenn Greenwald would be one of the people, I guess, who would be angry at you for this, or do they?

Doug Jay: Yeah, so Glenn, I have a long history with Glenn, actually, most of which maybe I better not describe. I think he might get pretty angry. But yeah, I used to actually be a really big Glenn Greenwald fan, and he was a really big Balloon Juice fan. He'd show up in the comments and he'd email us and say he liked the stories and stuff. So I think he doesn't want to get into it with me because he knows that I know things that if I said about him, he wouldn't look very good.

Kara Swisher: Oh, wow. Wow. Wow. Are there any other journalists that push back, or do they try to just laugh?

Doug Jay: Not really. Mostly I have almost no hostile DMs, ever, really. But I've got a lot of people like Jonathan Martin showed up once to say I was all wrong. Jonathan Martin and Matt Yglesias and Jonathan Chait have showed up sometimes to say that they don't like the account, that it's not funny, or stuff like that. But very few. I get much less criticism than I would have expected. Sometimes I actually think it's really weird to me that I don't have more hostile replies. And so I'll do a name search, like "Pitchbot idiot" or something like that to see if anybody said—I almost never find anything hostile.

Kara Swisher: Well, I think they do hit close to home. And you're like, "Oh, yeah, we do do that," or "That's the way we actually behave and we really shouldn't." That's what I get from it. Even though I just laugh at some of them out loud, what I do get from it is exactly what you're saying: "Man, we got to stop being so reductive." When I look at the headlines, I'm like, "Oh, you're kidding me. This is exactly the complaint."

Kara Swisher: I think the reflexive—what I really think is most dangerous, what I'm really trying to make sure of the most—is this reflexive desire to equate both sides in some way. And there may have been times in American political history where it did make sense to equate both sides, but I just think it doesn't make any sense now. I mean, even when Democrats do bad things, they shouldn't compare them to the Republican bad things because they're usually much worse. Whatever Trump has done is much worse. But that doesn't make Bob Menendez okay. I think it's very bad because in a weird way it ends up excusing bad behavior for Democrats by putting it in the context of bad behavior for Republicans. And I think that's bad too.

Scott Galloway: Do you see this as—if you were talking to a young journalist or a young comedian—it feels like these things kind of come and go. What advice would you have for a young journalist? Do you think this is an effective means of—I mean, you're doing it anonymously—but is this a potential good weapon in someone's quiver to advance their career in journalism?

Doug Jay: So I kind of think it is. I mean, I think that actually there are some—I don't know if they're younger anymore—but like one of the journalists who actually has done a lot of tweets that are sort of similar in style to mine is Dave Weigel. And I think, at least for me, it bought a lot of credibility with me as a reader. I didn't really know who he was. I'd see him on Twitter, and he'd be making these really sharp points, making fun of media framing. And I sort of thought, "This guy is really pretty sharp. I can really trust him, read his stuff." So yeah, I think if done properly, it would be a good thing for a journalist. I think some people do it anyway.

Kara Swisher: Yeah. It reminds me a lot of Fake Steve Jobs, which was really impactful. It was very, very funny. And he was anonymous for a while. But I remember thinking it was super impactful in that, or Spy Magazine, when they used to have those columns, where it really did skewer the media in a way that made you think, "Wow, we really have got to stop doing what we're doing," especially as things become more dramatic. And I know it's meant just to be funny and sometimes I just laugh at them, but it's a really interesting thing to really—all of those things made me as a journalist rethink what I was doing constantly, almost constantly. Especially Fake Steve Jobs.

Doug Jay: Yeah, I totally agree about Fake Steve Jobs. And that's kind of the tone that I want to—I mean, not all the time. Sometimes I do want to be mean. But that's basically the tone that I like to try to have.

Kara Swisher: Yeah. So last question: How long are you going to keep at it? Does it get exhausting? How many do you put out a day?

Doug Jay: That's hard. So actually, the thing that really keeps me going, I'd say, is my wife has a lot of suggestions about it. I have a bunch of friends that text me stuff. And then probably most importantly, I have a co-writer who probably DMs me about 20% of the things that I write, but also alerts me to lots of stories and stuff like that. And so I think as long as people are still helping me out that way and prodding me to do it, I'll stick with it for quite a while. I don't do as many tweets as I used to. Something about how crazy Twitter got sort of depressed me and I don't spend as much time on it as I used to.

Kara Swisher: Yeah, well, I think that's the way it is for a lot of people. Are you happy now for Travis, Kelce, and Taylor? It gives you a lot of—

Doug Jay: Very happy. It's a good—

Kara Swisher: Is there any journalist you're ready to go at that you haven't, besides Maureen and Glenn?

Doug Jay: That's a good question. Well, by the way, I don't really feel like I'm going at Maureen. I just think it's funny. What I'd like to do is make fun of the really bad New York Times columnists more. I don't even really mind Maureen Dowd at all. I'm not a huge David Brooks fan, but I don't think he's the worst. I'd like to make fun of Bret Stephens and Pamela Paul more, because I think that some of their stuff is really, really terrible.

Kara Swisher: Well, they're right there. Well, none of us will bring it up with Maureen, I'll tell you. I know her, but none of us mention it to her. I just have to say, we're like, "Should we say?" We don't know. We're not going to ask her. She's a really lovely person, actually.

Kara Swisher: Anyway, Doug Jay, I love your—I love New York Times Pitchbot. I think it's really funny. So keep the headlines coming, and I really appreciate it. It's a public service.

Doug Jay: Thanks for having me.

Kara Swisher: Thanks, Doug Jay. Scott, thanks for indulging me. I love him. I think he's so funny and witty. And it's not mean, and it's really funny, I think. But I think he does toe the line of meanness. He's not mean. There are a lot of really mean people on Twitter. He's not one of them. It's an enjoyable part of Twitter, and I hope he stays there, but I don't know. We'll see.

Kara Swisher: One more quick break. We'll be back for Wins and Fails.

[Ad Break]

Kara Swisher: Okay, Scott, let's hear some Wins and Fails. I'm going to go first because we continue to search for the origins of "Joey Bag of Donuts." Many of you have written to let us know the phrase goes back further than Mike Birbiglia. Comedian Don Herrera was talking about him back in the 80s. Let's listen.

[Audio clip plays]

Kara Swisher: A few of you also said "Joey Bag of Donuts" is a Wall Street phrase going back to the 90s. And of course, who can forget, as we said, "Vinny Bag of Donuts" references My Cousin Vinny. We got more mail over this week than any other single issue. So it's a fail. We're never going to find the origins of "Joey Bag of Donuts." But Scott, you keep saying that. So that's our personal fail.

Kara Swisher: But the win was that those two pairs of interviews with Yoel and Linda—I think it really was well done. I think it showed a lot of stuff that people needed to see and how difficult what's happening there is. That was, I would say, a win.

Scott Galloway: So my win is as a native son of California. I think we didn't have an opportunity to highlight the passing of Senator Dianne Feinstein. Senator Feinstein, one of the first female Jewish senators, ahead of the curve on assault weapons, ahead of the curve on women's rights, ahead of the curve on reproductive rights. She was pro-LGBTQ publicly before it was cool. She really lived up to—she was a brave woman. And unfortunately, her legacy is a touch tarnished. But when you look at her accomplishments, she just served the country and the state so steadfastly and was courageous. This was a woman who was brought to power by a murder.

Scott Galloway: And personally, the thing that saddens me about this is she was also a moderate. She absolutely had a deep appreciation for the power and importance of business in the private sector. And it feels like there are so few people in the Senate who recognize that in order to have the empathy and programs that we need to help our less fortunate, we need a private sector that is vibrant and can chug along and create tons of shareholder value. I feel as if the number of people that I loosely describe as moderates is just declining. And especially someone who has that kind of courage and respect. She was a lion in the Senate. A grandmother, married three times, born into wealth, but always advocated for the poor. I think she was a real iconic figure.

Kara Swisher: You know who gave an actual—there was a big contrast when she hugged Lindsey Graham during the Senate hearings of someone, I guess it was one of the Supreme Court judges. He gave a very good eulogy of her. For a minute, the old Lindsey Graham was back. Who wasn't being a Trump suck-up. They had a very close relationship, and he gave a wonderful eulogy for her on CBS, the morning show on Sunday. And I thought he really articulated—I know it's unpopular to quote him, but he used to be quite sensible. And I felt for a minute like, "Oh, look, there he is. And there she is." And it was a different time. Everything's gotten so partisan. And it reminded me—and I know people will be mad at me for saying this—but he was incredibly articulate and smart about the bipartisanship. Even he seemed nostalgic for it. And here was a friend of his who died and who he became friends with, and they were able to do legislation together. It was interesting.

Kara Swisher: He paid compliment to Ted Kennedy and her as the lion and lioness of the Democratic Party, and that they got stuff done across party lines in cooperation. It was really interesting. I urge you to go watch it, because usually lately, most of the stuff that comes out of his mouth is just blather. But this was—I was like, "Oh, that Lindsey Graham is—there he is." It was interesting. But I thought you're right. She's a legend. I agree with you, and I'm sorry for her final years. But good people plant trees, the shade of which they will never sit under. She was an incredible advocate.

Scott Galloway: There are hundreds of thousands of acres of what I believe is the most beautiful ecosystem in the world, and that's California desert. And she was a tireless champion for protecting California deserts. There's a lot of stuff that people won't remember, but she had a real impact on. Anyways, my win is the late, great Lioness of the Senate, Dianne Feinstein.

Scott Galloway: My fail is—so on Sunday, Tottenham Spurs played Liverpool. And as is often the case in sports, it's 1-1 and they're playing not to lose, push everyone, shove everyone to the defensive end of the field. And of course, they own goal and they lose. There's so much analysis around sports history that when you play not to lose, when you go defensive, you almost always lose. And my sports analogy here is that I think the Democrats with Biden are playing not to lose. And let me just say it now: We are really risking a lot with Biden. And I'll be very overt here. I think there are several people, but I'll just mention one. I think you put Governor Newsom on a debate stage with Donald Trump, and people look at him and they look at Donald Trump and they hear what Governor Newsom says, I think he's a lock. And I think you put Biden on a stage for six to nine months against Donald Trump—oh my gosh, we're playing not to lose. We're playing not to lose.

Scott Galloway: So I just think as a party, if we're really serious about the best odds for winning—and they say this every time—I think this election is massively important. I think if we re-elect an insurrectionist who's a criminal, it's just—I mean, there's a lot here. We should not play to lose. Maybe we'll get lucky and Trump will go to jail and Biden will decide to do the right thing. Maybe. That's not going to happen by the election. Could be, could be, who knows? But anyways, I'm really worried here.

Kara Swisher: I see you're very frustrated.

Scott Galloway: I'm really worried here.

Kara Swisher: What about Beto? Maybe Beto will come back, Scott, your favorite.

Scott Galloway: You mock me. I mock you because you were wrong. You kept picking loser after loser.

Kara Swisher: I'm terrible at politics, though.

Scott Galloway: Yeah, well, then maybe we shouldn't listen to you.

Kara Swisher: Anyway, we'll see. I think you're right to articulate this. A lot of people do, for sure. I'm going to support you, except your Beto choice was idiotic and remains that way years later.

Scott Galloway: Let me put it this way. The first presidential debate, the Republican nominee, Donald Trump, faces off against—what are you excited to see and what are you nervous as shit to see? I get it. Biden or Newsom?

Kara Swisher: I get it. I get it. It's like watching the Linda Riccarino interview. I mean, you tune in and you're like, I can't wait to have America see Newsom face off against Trump. If it's Biden, we're all like, oh, fuck. Let's just hope he gets through it. I get it.

Scott Galloway: But, you know, this is where we are. This is where we find ourselves.

Kara Swisher: But yes, I get it. I get your worries, Scott Galloway, but we'll see where it goes. You never know. Look what happened. We didn't have a government shutdown. Everyone thought there was going to be one. Anyway, politics is certainly not boring anymore.

[Transition to show closing]

Kara Swisher: Anyway, we want to hear from you. Send us your questions about business tech or whatever's on your mind. Go to nymag.com slash pivot to submit a question for the show, or call 855-51-PIVOT.

Okay, Scott, that's the show. We'll be back on Friday for more. I'm sure there'll be—Jeff McCarthy might be out of a job by the time we talk, but we'll see. Maybe not. Who knows? Who's to say? We'll be back on Friday for more. Scott, read us out.

Scott Galloway: Today's show was produced by Lara Neiman, Zoe Marcus, and Taylor Griffin. Ernie Intertot engineered this episode. Thanks also to Drew Burrows, Miel Saveria, and Gaddy McBain. Make sure you subscribe to the show, or if you're listening to podcasts...

Kara Swisher: Thank you for listening to Pivot from New York Magazine and Vox Media. We'll be back later this week for another breakdown of all things tech and business. Kara, have a great rest of the week.