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Christopher Lochhead Follow Your Different™

6 Nov 2026 · 24m · 10 chapters

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PSJ Special Segment: The First AI-Assisted Election | The Pirate Street Journal

In short

A “Pirate Street Journal” special segment arguing the 2022 midterms may be the first election significantly assisted by AI, focusing on how AI changed voting decisions, what went wrong, and concerns about AI political bias.

Guests/backgrounds

Jimmy (host; “digital native,” immigrant/independent; used Claude/other AIs for ballot guidance; describes “positive racism” when information was missing). Eddie (co-host; first-time voter with AI help; used Claude to build a voting framework and pre-vote plan). Bree (co-host; Alaska first in-person voting; analyzed how election marketing influenced her; discusses “dark money” confusion).

Key claims

AI can synthesize voter priorities and interpret ballot measures; it’s hard to get AIs to “tell the truth” because they try to agree with users; AI builders may be politically biased; future “voting agents” could reduce Election Day uncertainty.

Notable examples

Claude helped Eddie pre-plan local races; he voted randomly/against incumbents where info was absent; he voted for an Asian candidate “when in doubt.” Bree misread “vote no on number two for dark money” marketing and later realized it referred to campaign disclosure/monitoring, not “dark money” as she assumed.

Written by AI. May contain mistakes.

Chapters

1:04

AI's Role in the Election

Exploring how AI was utilized during the election and its impact on voting.

“This one's going to help you look past the headline parrots and see the election through the category lens.”
1:40

Personal Voting Experience with AI

Discussion of using AI to navigate personal voting decisions, including insights and challenges faced.

“but I wanted to share, we wanted to share how we voted, not why and what we did, but how we use AI to do that.”
3:56

Voting Strategies and Biases

Examining voting strategies that emerged from limited information and the concept of positive racism.

“But then you get to a point where it was kind of funny for me and maybe a little controversial, whereas when you don't have information because I wasn't able to prepare it.”
7:27

The Role of AI in Understanding Props

Understanding how AI facilitated comprehension of ballot propositions during the election.

“Of course, I can't figure out the budget.”
9:21

Concerns About AI Bias in Elections

Discussion on the political bias in AI development and its implications for future elections.

“that this election was for sure the first AI enabled election at any kind of scale.”
14:00

AI and Political Bias in Elections

Exploration of AI's role in understanding electoral processes and biases.

“And so here's the other interesting thing.”
14:51

Creating a Voting Agent

Discussion on developing a dedicated voting agent to streamline the voting process.

“And I'd like to do it by entrepreneurial means, not by more regulations and laws.”
15:56

Personal Experiment with Election Marketing

A personal account of navigating election marketing and its discrepancies.

“And so like what you what you want, you uploaded the marketing material.”
18:21

The Role of AI in Truth-Seeking

Analyzing how AI can aid in achieving truth and unbiased information in elections.

“And this is also interesting because it goes back to Jensen when we talked about last week on episode 26, I think Jensen said everyone wins with AI.”
20:17

Reflections on the Election Process

Contemplation on the peaceful transfer of power and gratitude for the democratic process.

“And I think the way we need to have an ongoing dialogue heading into the presidential election in two years about the role of AI in voting, because it is going to be exponentially more important.”
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Transcript

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0:00There's signage everywhere that said these are not Muppets. We're not connected to Jim Henson. Not Muppets, not Muppets. Why? Because it's raunchy as hell. This is probably the first truly AI-assisted election. I ran an experiment on myself, and it's kind of ironic that the digital native here didn't use AI in this election cycle. Hi, I'm Jimmy so-and-so. I'm Asian, and that means I'm good at math. When in doubt, I don't have any other information. I voted for the Asians. But it's positive racism. I don't see a vote no on number two for dark money anywhere. This election was for sure the first AI-enabled election at any kind of scale.

0:38Election Day has no drama because it's been preordained by these voting agents. It takes work to get the AIs to tell you the truth. If AI is aiding the government, even the people voting are going to win. Now this is the controversial part. you're the pirate street journal hey pirates welcome to a special segment of the pirate street journal the midterms were yesterday and this might be the first real ai election so we skipped the who won talk and asked a different question what happens when you let ai help you vote some of what we found was helpful some of it was surprising and one confession might make you a little uncomfortable but it'll definitely make you laugh stick around to the end for the story that puts the whole election in perspective.

1:26So Pirates, let's hoist the sails. This one's going to help you look past the headline parrots and see the election through the category lens. So we were just talking about how this is probably the first truly AI-assisted election. The midterms happened yesterday, and obviously there was a big sweep to go Democratic, but I wanted to share, we wanted to share how we voted, not why and what we did, but how we use AI to do that. And so in particular, I brought my son, this was his first time voting. And I realized, I don't know what his political views are. He probably doesn't know what his political views are.

2:01So what I did was I said, here, I went to Claude. I said, here's my address. I want you to bring up my ballot. And I want you to help me, A, build a framework for how to vote. I want you, B, interview me to see what I care about. And we'll, you know, we rejigger the framework so that I have a North star of what to look for. And then C, just kind of, I want to vote ahead of time so that when I'm in the voting booth, I'm not pressured and not wondering, and just, I want to get in and out and do all of that stuff. So I did it. And what was fascinating was it solved the problem of voting was like, I wanted to vote.

2:37It's your civic duty. But then I was like, I'm bad at this. I, outside of the two, three people at the top that have name recognition, I don't know who these other people are and I don't know what they care about and I don't know what I care about. And so I actually felt more informed. I did notice that Claude did not catch. There were some votes I was like, hey, you didn't prepare me for this once. I wasn't quite there. So there's a little bit of gap there. But what was funny to me was that some of the local elections, judges and the forest preservers, it's beyond the reach of AI. There's no information about them.

3:09And therefore, I had nothing to vote. So you go through kind of the normal people. And then what I realized, what I came down to was not a partisan thing, even though the legacy premise of pick a party, vote that it's simple. That's the reason why it works. It's not because I think people actually necessarily believe in one party or the other. It's just a way to get through the process. And so what I had was a very different one, which was like, here are the things that I cared about. You know, I cared about the economy. I cared about there are certain things around. I wanted a reasonable stance on AI, not a reflexive one, but a reflective one.

3:46I wanted people to fight forward, not backwards. And so kind of just looking at it. And I wanted to see outcomes, measurable numbers that I could see. Did you actually deliver the goods or not? And that's how I went through it. But then you get to a point where it was kind of funny for me and maybe a little controversial, whereas when you don't have information because I wasn't able to prepare it. Here's what I did was I said, you know what? I believe in the founders framework and I want checks and balances. And so Illinois, where I vote, is largely democratic. So not because I'm staunchly one way or the other.

4:18I was like, you know what? Let's throw some chaos into the mix and I want some accountability. So I generally voted against incumbents. when I had no other information. And when I know that Illinois is a highly democratic state, and I said, you know what, down ticket, I'm just going to throw a couple of random votes, Republican. And it was basically a random vote because I didn't have any information. But the best desire that I had was I want some chaos. I want some competition. I want people to earn their vote and earn their seat and not just be handed it. So that was the one. And then two was at the very, very dregs of there is no data.

4:52You're in a desert. You have no information. What I found myself was being a little racist. And what I mean by that was I voted based on demography. By the way, I'm just going to interrupt you. I hate to do it because I know you're in a flow, but it's funny. There's a Broadway show that was very popular years ago. I saw it early in its run called Avenue Q. And it is adult Muppets. Not connected to Muppets. There's signage everywhere that said these are not Muppets. We're not connected to Jim Henson. Not Muppets. Not Muppets. Why? Because it's raunchy as hell. The Muppets have sex in the thing and it's raunchy.

5:29Anyway, and it's a musical. And one of the songs, do you know the song I'm going to point you to, Eddie? No? You don't know where I'm going? Okay. One of the songs in Avenue Q, and maybe, Bree, we can put a link to it, goes like this. Everyone is a little bit racist. Yeah. I've seen this before. absolutely put a link to it because you know what it's true the people who are like i don't see color i don't believe you none of us believe you you may think that but everybody at some level uses if you define racism as a spectrum and not a binary thing of like you're using a little bit of race and what you can see superficially to make a decision i'm not saying you're a bad person that you walk across the street when you see an asian guy come whatever it is but for me what what race You have a positive bias towards.

6:18We'll put a link towards this one is Ronnie Chang, the comedian, did a very funny bit about why you should elect an Asian American for president. Because where do you go at Thanksgiving and Christmas when you're tired and nothing's open? You go to Chinatown because everything's open. They're still working hard. Everything's cheap and it's delicious. And he's like and he's like, look, Asians work hard. They're good at math. It's high time that you put an Asian in the White House. And that's where I went was like, when in doubt, I don't have any other information. I voted for the Asian. And is it racist?

6:48Absolutely. Is it prejudice? But it's positive racism. Well, and this is my thinking, and flawed as it may be, and I totally admit this may be a wrong way of doing things, is that at some point in your lineage, you had somebody who was an immigrant who worked harder than they had to because they had to. And the edge that they had was on math. And so when in doubt, I wanted to vote for somebody like that. And not to say that other people aren't good at math and they aren't working hard, but I'm just voting my experience, which I suspect a lot of people do anyway. So and it was when I had no other information.

7:21But that's how I use AI to get there. And hopefully, I will get you the full ballot the next time so that I don't have to be as racist on my next. So here's the funny thing that if I was a campaign manager for an Asian candidate and you really want it to go like funny you go hey listen what are our two biggest problems the budget and affordability what are those two things about math what are we asians really great about math it's just sitting right there and you know i hire the math people don't hire the humanities these people? Of course, I can't figure out the budget. We got a bunch of people who studied social sciences for the love of God.

8:05A hundred percent, a hundred percent. You know, as, as somebody who has experienced both negative racism, I've also experienced the positive racism where in certain settings, when I'm doing spreadsheet Kung Fu, there was a bit of a, well, that makes sense you know and i'm like and and some people will assign a little more intelligence to me than i probably have and so do i correct them all the time no no no but you know it's i'm just kind of naming it's what we all think and it won't always be true if you're a fifth sixth generation asian how funny it would be though if somebody actually ran a let's call it a positive racist campaign right?

8:46Hi, I'm Jimmy so-and-so. I'm Asian. And that means I'm good at math. It would be so funny. Well, I think what we were clearly identifying, where my takeaway from this election cycle was AI was very, very helpful in helping me understand what I want, what I cared about, what I voted for, helping me gather the information and synthesize in a clear way. And the more informed I felt, the less racism I needed to use. So this is all in that positive. Now, to turn a little bit serious for a second, I do think it's fascinating that this election was for sure the first AI enabled election at any kind of scale.

9:30Right. And I did a very similar thing to Eddie. I said where I lived, I wanted to look at there's lots Lots of props in California. I wanted to understand them. And in the past, I've always done this kind of research. And as the Internet became popular and available, we used Google to do this. But it still took a lot of work. You had to, you know, rummage around a lot of stuff and read a lot of stuff and watch some videos and to try to get educated. So the thing that's interesting is, number one, AI is an incredible tool for voting. because the props, there were several props in California that I knew exactly what the prop was and what I wanted to vote on it.

10:13But when I got the ballot, Brie, I couldn't tell what I should vote yes or no. Because as we all know, some states are better than others at being clear about what the hell the vote is. And do I vote yes or do I vote no? And so just like Eddie described, I told I actually used three AIs. ChatGPT was my first one. And then I used perplexity and then I used Grok. Interestingly enough, by the way, in my experience, Gemini doesn't want to have any conversation about political things very much. It sort of shuts down pretty quickly anyway. And so I just like Eddie mentioned, I said, these are the things that matter to me and I want to understand each of these props.

11:02And it turns out the props that I was presented with, approximately two thirds of them were about either increasing taxes or making it easier to increase taxes. And of course, many of them are not worded that way. And look, I'm not the smartest person in the world, but I am not the dumbest either. And and when you read a prop and you don't understand it and you know what the props about, but you don't know how to vote. So I think it's very powerful to do what Eddie was describing. And in my case, I always argue and debate with the AIs, and I use multiple AIs because I want to make sure I'm trying to do real diligence here.

11:41OK, so I think that's very interesting. The second piece of this that's interesting is if you understand about agents, where is this going? Well, if I was an entrepreneur, a younger man, I might be building the world's first nonpartisan AI assistant. And you think about the problem that Eddie faced in Napierville. Right. And in our case, in our little beach town in California, I was shocked at how much the AIs did know. You know, we had a friend running for city council in Capitola, California. Capitola is this town of 10 ,000 people. And ChatGPT knew a lot about that race. And it knew about both of the drops.

12:29We had a drop of a vote count at about eight, nine o 'clock last night. And then we had another drop around, I don't know, 2 a.m. It was very blurry, the whole thing, because we were trying to be there and supporting our friend. But the AIs knew about that stuff. OK, so if I was an entrepreneur, I might get busy building legendary agents that will go and ferret out all this stuff so that even in the smallest places, if you think about where Bree is right now in Alaska. Right. If I'm Bree in Alaska, I would want the level of information I had about about Santa Cruz and Capitola in Alaska or anywhere else in the country for that matter.

13:08Right. So I think there's an opportunity there. And here's the other part I wonder. Now, this is the controversial part. You know, we saw a blue wave and it was it was clear it was coming. I think I'm not a political expert, but I talked to many. I had pollsters. We had pollsters on the podcast. It seemed pretty clear the Republicans were going to lose the House, maybe hold the Senate. Of course, now they've lost the Senate. And there was a blue wave. Texas flipped. Right. That's shocking at the governor and the senator levels. And so I don't think this is the case. However, I'm going to bring it up anyway.

13:44The leading AI companies are created by people who are overwhelmingly leaning left. Open AI, Anthropic, Microsoft, Google, roughly 80 percent of the engineers at those companies, if you believe the stats, are left leaning and tend to vote Democrat. And so here's the other interesting thing. What are we going to do going forward to make sure that when we are now all relying on the AI to figure out what the props actually mean? Because I think some of them are written to be confusing on purpose. When we're using AI to understand who all the judges that we don't know are, when we're using AI to pick the treasurer for the I don't know what, et cetera, et cetera.

14:36Right. We need to make sure it's unbiased. And so there is a there is a conversation I think we need to have in our country about the political bias of the people building the AI and what can be done. And I'd like to do it by entrepreneurial means, not by more regulations and laws. I think to your point, Christopher, there's a new category that can be created. And I think, Brie, how you voted was interesting about that is you have polls, which are imperfect, and you have the voting results that are - And remember, the role in the prediction markets has increased materially in the last decade, right?

15:13Yes. And your prediction markets are somewhere in between there, right? I actually think that you could easily build out a dedicated voting agent that said, walk me through what you care about, walk me through your voting history. And then let me explain to you ahead of time, not on the day of or the week before, how you vote and that you bank that into almost like a Nielsen panel-esque thing so that the people running can say, if I choose this position, what do I pick up? And I will completely open source my preferences ahead of time so that people can say, oh, it's not just Eddie answering a poll.

15:49These are literally his voting history, the things that he cares about now, the questions that he has that he's confused about. And if you do these things or you commit to these things in your marketing materials, because then I think you could have a wildly different one where Election Day has no drama because it's been preordained by these voting agents and the like. And so like what you what you want, you uploaded the marketing material. What do you do? No, I ran an experiment on myself. And it's kind of ironic that the digital native here didn't use A.I. in the selection cycle. It's kind of funny.

16:23The two analogs were all about the AI and the native digital, not so much. But you did do something very interesting, Bree. I did something different this year. I wanted to run an experiment on myself and see how the marketing that I saw throughout the entire election cycle, advertisements on TV, all of those text messages, all of that junk mail you get, what it said and how that influenced what I thought about the election. And then I judged all of my research on that once it came time to vote. I went back and I said, OK, let's go verify a few things. So I'm mildly prepared and compared what I saw in the marketing material throughout the election cycle with what was on the ballot.

17:04Wildly different things, which is just crazy to understand and be like, oh, I had all these marketing things like vote no on number two, which every Alaskan was saying. And I got there and I said, I don't see a vote no on number two for dark money anywhere. That's so strange. And I finally figured it out afterwards. I was like, oh, that's what they were talking about. It wasn't dark money. It was about how we monitor politicians and their spending and where their money comes from and the disclosures around politician spending. That's what the dark money was. Completely different than what I saw in the marketing material.

17:39So even as I'm driving up, it was my first time voting in person because Alaska doesn't have mail-in ballots. And Washington State, where I grew up, is the whole situation. And there's these couple people 200 yards out from the polling place as they had their signs. They were right at the legal place. I looked at the name and I said, I'm going to try and find that on the ballot. Never found the name on the ballot. I'm sure it was there, but they had to have been at the bottom of the list. Never saw it. So I judged it all on marketing material. And I think as we bring AI into the future, there's going to be a no BS policy of what they put on the ballot and what we see in marketing is going to be a lot easier to decipher.

18:21And this is also interesting because it goes back to Jensen when we talked about last week on episode 26, I think Jensen said everyone wins with AI. This is going to be another thing. If AI is aiding the government, even the people voting are going to win. Interesting. That's exactly right. And I think in spite of my comments about the companies being radically biased, and I do believe it, I experience it in my own work with AI. As a side note, when the three of us go to write anything, we start with a premise just like anybody. However, we are not ideologues. And so when we start with a premise, you know, about category design or some other topic that we're writing about kind of in our lane, if you will, we always tell the AIs, particularly when we're looking for data and we're data hounds.

19:15Look, this is the premise. This is what I'm thinking. This is the theme of what we're going to be writing, et cetera, et cetera. But now I want to do research. The AIs are purpose built to agree with you and make you feel good. Right. So so forget whether they have political bias or not. I think they do. But forget that for a second. They are prebuilt to agree with you. And so we have to be explicit all the time with AI to say, listen, we want the facts. We want the truth. We are not in the spin business. If the premise we're going into is wrong, then we want to understand that. or if there's nuance or whatever it is, we want to understand based on data this topic.

19:56And then we will write according to the facts. We are not trying to spin something or leave something out or lie with the truth or do any of that stuff. And so my point is, it takes work to get the AIs to tell you the truth if for no other reason that they're trying to make you happy and agree with you. So I think all that is very important. And I think the way we need to have an ongoing dialogue heading into the presidential election in two years about the role of AI in voting, because it is going to be exponentially more important. The other thing I want to say about this, you know, is today's the day after the election and everybody's talking about licking their wounds if they lost or celebrating if they won.

20:41and there's red America and there's blue America and all this. For the record, I'm an independent and I'm an immigrant to this country. So I'm a red, white, and blue American. I'm not a red American or a blue American. And I'll never forget when George H.W. lost the presidential election to Clinton. Right after that, and you know, the outgoing president is there for the ceremony and all that stuff, right? Shortly thereafter, he gave an interview and they were asking him how he felt and what he was doing now. And, you know, the sort of several months after leaving office kind of interview. And he said something that has stayed with me ever since.

21:23He said, standing up there in front of all of those people, watching Bill Clinton get sworn in after Clinton beat him. He said, look, was I happy? Of course not. I wanted a second term. He said, however, I was up on that stage in awe of America, the most powerful country in the world. Changing hands of power, a handing of the torch, so to speak, based on the will of the people. And not one ounce of blood was shed. And so whether you're upset this morning or happy this morning or somewhere in between, and look, I have my feelings about the election just like everybody else. However, the place I'm holding, I'm sitting in today is that place that President H.W.

22:20Bush talked about, which is, you know what? We just had a very contentious election. Big change just happened. And nobody died. Right. We did this peacefully. And and when the new Congress comes in, there will be a handing of the baton and the people who got elected out will leave peacefully. And the people who came in will come in and they'll face their next election and so forth and so on. It's easy to take that for granted. So this morning, despite whatever my positive and negative, because I have positive and negative feelings about this election, like I think many people do. I put those to the side and I just sit here and go, you know what?

23:04Most of the world this doesn't happen in. And so I'm very thankful to be an American. I'm in awe of this political process. And God bless America. Thanks for pressing play, Pirate. You just spent 30 minutes becoming the smartest person in the room. Want it to stay that way? Subscribe or follow wherever you're watching or listening. It's free and you'll never miss an episode. and if this one gave you a case of thinkers high give it a like or a five-star rating it helps other pirates find us and we'd greatly appreciate it and if you want to go deeper and build your own category the founding membership is for you the link is in the show notes see you next week pirates

From the publisher

The midterm elections wrapped up yesterday, and plenty of people are still sorting through the results. But the hosts of the Pirate Street Journal came away with a different kind of takeaway. This may have been the first AI-assisted election at any real scale, and each of them used the technology in a very different way. One built a voting framework with Claude, one cross-checked three chatbots on California propositions, and one skipped AI entirely and tested what campaign marketing does to a voter’s head. What they found was useful, a little uncomfortable, and in one case very funny.

You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.

 

Building a Voting Plan With a Chatbot

Eddie went into this cycle with a problem most of us share. Beyond the two or three names at the top of the ballot, he had no idea who half the candidates were. So he gave Claude his address, asked it to pull up his ballot, and had it interview him about what he cares about. The result was a personal framework: a sensible economy, a reflective stance on AI, leaders who look forward, and measurable outcomes over speeches. He voted ahead of time, so the booth held no pressure.

The tool had gaps. It missed a few races, and judges and forest preserve candidates were beyond its reach because no information existed. Eddie filled the holes with a loose belief in checks and balances, voting against incumbents in a heavily Democratic Illinois and tossing a few random votes to Republicans for the sake of competition. When he had nothing at all, he confessed he voted for Asian candidates, a bit of what he called positive racism borrowed from a Ronny Chang comedy routine.

 

Cross-Checking Props and Local Races

Christopher faced a different headache in California. Many ballot propositions are worded so confusingly that even when you know what you want, you can’t tell whether to vote yes or no. He ran the props through ChatGPT, Perplexity, and Grok, and argued with each of them, since he figures a single chatbot is too eager to please. Gemini, he said, shut down any political conversation almost immediately. About two thirds of his props turned out to involve raising taxes or making it easier to raise them.

He was also surprised by how much the models knew about hyper-local races. ChatGPT had details on a city council contest in Capitola, a town of roughly 10,000 people, and even tracked the vote count drops. That raises an opening for entrepreneurs: a nonpartisan voting agent that gives someone in rural Alaska the same depth of information as someone in a California beach town.

 

Bias, Marketing Noise, and a Peaceful Handoff

Christopher raised the touchy question of who builds these models. He pointed to a stat that roughly 80% of engineers at the major labs lean left, and argued that bias deserves a public conversation, ideally solved by builders and not by new regulation. He also noted that models are designed to agree with you, so you have to tell them to give you facts and not flattery. Bri ran the opposite experiment. She skipped AI, judged the election by the flyers, texts, and TV ads she saw, then discovered the “vote no on number two” slogans had little to do with what was printed on her ballot.

Christopher closed on a note that stuck. He recalled George H.W. Bush saying that watching power change hands without a drop of blood shed is the real marvel. Whatever side you’re on this morning, the peaceful transfer is worth appreciating.

To hear more about the topics in this week’s The Pirate Street Journal, download and listen to this episode. You can also read more Pirate Street Journal entries in the Category Pirates newsletter.

 

We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, X, LinkedIn, and subscribe on Apple Podcast / Spotify!

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