WEBVTT

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OK, I want you to picture something for a second.

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The year is 2004. You're in Orange County, California.

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Right, which, you know, has a certain reputation,

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the Orange Curtain, as they call it. Exactly.

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It's this bastion of conservatism. So you're

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there. You pick up a free newspaper, an alt weekly

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called the OC Weekly. And we should probably

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explain what an alt weekly even was for anyone

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who, you know, didn't. grew up with them. That's

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a good point. It's not like today's media landscape.

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Not at all. Basically you had the big serious

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paid newspaper and then you had the free alt

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weekly. It was kind of the rebellious younger

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sibling. A little gritty. Funded by ads for local

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bands and futon shops. Totally. And editorially

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they were where you found the stories the big

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papers wouldn't touch. They had an attitude.

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So you're flipping through this paper and you

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land on a column with a title that feels Well,

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it feels like it's designed to start a fight.

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Yeah. It's called Ask a Mexican. I mean, even

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saying it now, it has a certain charge to it.

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In 2004, in that specific place, it was just

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radioactive. And you'd think, OK, this is a joke.

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This won't last a month. And you'd be half right.

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That's the amazing part. It was a joke. It was

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literally designed as a one -time spoof. And

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instead, we're here doing a deep dive on how

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that one -time spoof became a syndicated cultural

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phenomenon, won major awards, and then ended

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in this. this dramatic principled stand. It's

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an incredible story. So our mission today is

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to unpack that whole journey, the rise, the paradoxical

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acclaim. the fall of the industry around it,

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and finally, the resignation. It's a story about

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free speech, media economics, and intellectual

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property that every single creator should hear.

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Absolutely. Okay, so let's start at the very

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beginning. You said it was a spoof. How did that

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even come about? Well, Gustavo Arellano was a

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staff writer at the OC Weekly, and he pitched

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this idea basically as a way to satirize the

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racial tensions simmering in Southern California.

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Just poke the bear a little bit. Exactly. The

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premise was simple. Readers send in any question

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they have about Mexican -American culture, stereotypes,

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you name it. And a persona, the Mexican, answers

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them. It just sounds like a recipe for disaster

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on paper. It could have been. But the execution

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was key. He wasn't just being offensive for the

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sake of it. He established a very specific format.

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Right. The sources say he'd answer two questions

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a week. But the tone was explicitly politically

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incorrect. And that started with the opening

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line. His signature. Dear Gabacho. Dear Gabacho.

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Every single time. You should probably define

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that for people. Gabacho isn't exactly a term

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of endearment, is it? No, not traditionally.

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It's Mexican slang for a white American, sort

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of like gringo, but maybe with a bit more of

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an edge. So right off the bat, he's setting a

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tone. He's flipping the entire power dynamic.

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Usually, you know, the expert voice in media

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is the white voice explaining the other. Here,

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he's saying no. I'm the authority. You're the

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outsider. Sit down and listen. It was brilliant.

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And because it was framed as a spoof, he could

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get away with so much more. He had cover. Yeah.

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And people, I mean, they just loved it. The column

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went from a one -off joke to the paper's most

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popular feature like overnight. But the questions

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weren't just fluff, were they? It wasn't all

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about why do Mexicans like tequila? No, and that's

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the Trojan horse of the whole thing. It started

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with some of that, sure, the silly stereotypes,

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but it very quickly got serious. Like what kind

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of serious? Like deep questions about illegal

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immigration, about labor disputes, about complex

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class issues within the Mexican -American community.

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So people were using this satirical column. as

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a genuine forum for some of the most heated political

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debates in the country. They were. And Arellano

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would answer with this mix of biting humor and

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actual factual history. He would hide the medicine

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in the candy. Which brings us to the part that

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I still can't quite wrap my head around. The

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award. Yeah, the critical acclaim. When I hear

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about a column that intentionally uses racial

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slang and pokes at stereotypes. I don't immediately

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think award getting journalism. You'd think canceled,

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right? But this was a slightly different era

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and the recognition he got was staggering. I

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mean, let's just run through the list. Please

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do. OK, so in 2007, he gets the President's Award

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from the Los Angeles Press Club. That's a big

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deal. The National Hispanic Media Coalition gives

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him an Impacto Award. OK, so he's being recognized

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by both mainstream and Hispanic media groups.

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Right. And then in 2008, the California Latino

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Legislative Caucus, we're talking actual elected

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officials, they give him the Latino Spirit Award.

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Wow. So politicians are endorsing this supposedly

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politically incorrect column. It just shows that

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they understood he was doing something much deeper

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than telling jokes. He was forcing a conversation

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that needed to happen. But there is one award

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here that just seems like the ultimate paradox.

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The Association of Alternative News Weeklies

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gave him best nonpolitical column. Twice. Twice.

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How is a column tackling immigration and labor

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policy nonpolitical? That makes no sense to me.

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Well, that's the beautiful irony of it, isn't

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it? I think it shows how the media establishment

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defined politics at the time. If you weren't

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writing a stuffy op -ed about tax brackets, it

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wasn't considered politics. Because Ariana was

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writing about culture and using humor, they filed

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it under lifestyle. Even though culture is probably

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the most political thing there is. Of course

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it is. He was probably shaping more opinions

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on immigration than half the political columnists

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out there, all while being classified as a humorist.

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The satire was his passport to get into these

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serious topics without people's defenses going

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up. Exactly. And that success naturally led to

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expansion. In 2008, Scribner's publishes a book

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collection also called Ask a Mexican. He goes

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from newsprint to hardcover. That's a major step.

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It is. And the syndication numbers really tell

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the story. At its absolute peak, the column was

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running in 39 different markets across the country.

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39. So from one paper in the OC to nearly 40

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cities. It was huge. You could be in Denver or

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Houston and pick up the local Alt Weekly and

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read Dear Gabacho. So 2008 feels like the high

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watermark. He's got the awards, the book, massive

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syndication. But the media business is, well,

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it's brutal. It is. And the story of the column

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from that point on perfectly mirrors the story

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of print journalism itself. The Great Collapse.

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The Great Collapse. If you look at those syndication

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numbers, it's a terrifyingly steep graph. The

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source material mentions an interview he gave

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in 2017 where he talks about the death of journalism.

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Yeah. By that point, the number of papers carrying

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in the column had dropped from 39 down to around

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12. From 39 to 12, that's more than two thirds

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of his reach just. Gone. It's devastating. And

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he even joked about needing to do a new census

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just to figure out where he was still being published.

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But it wasn't because people stopped reading

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the column. Right. It was because the papers

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themselves were dying. Exactly. The business

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model of the Alt Weekly was built on classified

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ads. And then Craigslist came along and just

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wiped them out. And Facebook finished the job

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on the ad revenue side. So you have this vital,

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important piece of commentary. But the ships

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carrying the message are sinking all around it.

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It's such a bleak picture of that time. But the

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story doesn't just trail off into nothing. It

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ends with a bang, not a whimper. It really does.

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It ends with a specific moment, a conflict that

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says everything about the guy behind the column.

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October 13th, 2017, Gustavo Arellano resigns.

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But it's the why that matters. This wasn't about

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money or a better job. No, this was a moral stand.

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The owner of the OC Weekly at the time came to

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Arellano, who was the editor by then, and gave

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him a directive. And that directive was what?

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Fire half of your staff. Wow. Just like that.

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Look at your team, pick half and show them the

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door. It's an impossible position for any leader

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to be in. But Ariyama's response was incredibly

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simple. He just said no. He refused to do it.

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He refused. And when they insisted, he chose

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to resign himself rather than fire the people

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who worked for him. That takes a level of integrity

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you just don't see very often to basically fire

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yourself to protect your team. It's a profound

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ethical choice. And it cemented his legacy. But

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it also created a huge, messy problem. He walked

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out the door. But what happened to his column?

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What happened to Ask a Mexican? Right. Can you

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just take it with him? Go start a Substack the

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next day. He could not. And this is where we

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get into the really important lesson about intellectual

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property. OK, break this down because it's a

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distinction a lot of people get wrong. So Ariana

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wrote the words. He owns the copyright to the

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individual articles he wrote. But the newspaper,

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the OC Weekly. owned the trademark. And the trademark

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is the brand name itself. Exactly. The trademark

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is the name, the logo, the brand identity. Ask

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a Mexican was considered a product of the paper.

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They owned the title on the box. So when he left,

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the name had to stay behind. It did. He built

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this persona, this voice, this national brand

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from nothing. The corporation owned the nameplate

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on the door. It's kind of heartbreaking. It feels

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like a story you hear with rock bands all the

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time. The singer quits, but the label owns the

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name of the band. It's the exact same principle.

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He made it clear in interviews, you know, they

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own the trademark, but they don't own me. They

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don't own my voice. So could the paper have just

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hired a new Mexican? Legally, they probably could

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have tried. But in reality, no way. Because the

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brand was him. His specific voice, his knowledge,

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his humor, it was so unique. Any replacement

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would have been seen as an imposter instantly.

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The readers would have burned the place down.

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So the trademark, the brand, becomes effectively

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worthless without the creator behind it. Precisely.

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The paper held the legal document, but he held

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all the actual value. It's a fascinating standoff

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between corporate ownership and creative identity.

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It really is. So let's just recap this wild ride.

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A one -time spoof from 2004. Becomes an award

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-winning, nationally syndicated column that actually

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shapes conversations on major issues. Its distribution

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network then collapses as the newspaper industry

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implodes. And it all culminates in 2017 with

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an act of defiance where the creator walks away

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on principle, leaving the trademark behind but

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taking all the actual value with him. What an

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incredible story. It really forces you to think.

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It does. It leaves you with this kind of provocative

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thought about identity and property. Which is

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what? Well, if a company owns the trademark to

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a persona, but the creator owns the voice, the

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talent, and the soul, what is the brand actually

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worth without the human who gave it life? A question

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every creator should probably be asking themselves.

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A great place to leave it. Thanks for this deep

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dive. My pleasure. We'll see you next time.
