OK, I want you to picture something for a second.
The year is 2004. You're in Orange County, California.
Right, which, you know, has a certain reputation,
the Orange Curtain, as they call it. Exactly.
It's this bastion of conservatism. So you're
there. You pick up a free newspaper, an alt weekly
called the OC Weekly. And we should probably
explain what an alt weekly even was for anyone
who, you know, didn't. grew up with them. That's
a good point. It's not like today's media landscape.
Not at all. Basically you had the big serious
paid newspaper and then you had the free alt
weekly. It was kind of the rebellious younger
sibling. A little gritty. Funded by ads for local
bands and futon shops. Totally. And editorially
they were where you found the stories the big
papers wouldn't touch. They had an attitude.
So you're flipping through this paper and you
land on a column with a title that feels Well,
it feels like it's designed to start a fight.
Yeah. It's called Ask a Mexican. I mean, even
saying it now, it has a certain charge to it.
In 2004, in that specific place, it was just
radioactive. And you'd think, OK, this is a joke.
This won't last a month. And you'd be half right.
That's the amazing part. It was a joke. It was
literally designed as a one -time spoof. And
instead, we're here doing a deep dive on how
that one -time spoof became a syndicated cultural
phenomenon, won major awards, and then ended
in this. this dramatic principled stand. It's
an incredible story. So our mission today is
to unpack that whole journey, the rise, the paradoxical
acclaim. the fall of the industry around it,
and finally, the resignation. It's a story about
free speech, media economics, and intellectual
property that every single creator should hear.
Absolutely. Okay, so let's start at the very
beginning. You said it was a spoof. How did that
even come about? Well, Gustavo Arellano was a
staff writer at the OC Weekly, and he pitched
this idea basically as a way to satirize the
racial tensions simmering in Southern California.
Just poke the bear a little bit. Exactly. The
premise was simple. Readers send in any question
they have about Mexican -American culture, stereotypes,
you name it. And a persona, the Mexican, answers
them. It just sounds like a recipe for disaster
on paper. It could have been. But the execution
was key. He wasn't just being offensive for the
sake of it. He established a very specific format.
Right. The sources say he'd answer two questions
a week. But the tone was explicitly politically
incorrect. And that started with the opening
line. His signature. Dear Gabacho. Dear Gabacho.
Every single time. You should probably define
that for people. Gabacho isn't exactly a term
of endearment, is it? No, not traditionally.
It's Mexican slang for a white American, sort
of like gringo, but maybe with a bit more of
an edge. So right off the bat, he's setting a
tone. He's flipping the entire power dynamic.
Usually, you know, the expert voice in media
is the white voice explaining the other. Here,
he's saying no. I'm the authority. You're the
outsider. Sit down and listen. It was brilliant.
And because it was framed as a spoof, he could
get away with so much more. He had cover. Yeah.
And people, I mean, they just loved it. The column
went from a one -off joke to the paper's most
popular feature like overnight. But the questions
weren't just fluff, were they? It wasn't all
about why do Mexicans like tequila? No, and that's
the Trojan horse of the whole thing. It started
with some of that, sure, the silly stereotypes,
but it very quickly got serious. Like what kind
of serious? Like deep questions about illegal
immigration, about labor disputes, about complex
class issues within the Mexican -American community.
So people were using this satirical column. as
a genuine forum for some of the most heated political
debates in the country. They were. And Arellano
would answer with this mix of biting humor and
actual factual history. He would hide the medicine
in the candy. Which brings us to the part that
I still can't quite wrap my head around. The
award. Yeah, the critical acclaim. When I hear
about a column that intentionally uses racial
slang and pokes at stereotypes. I don't immediately
think award getting journalism. You'd think canceled,
right? But this was a slightly different era
and the recognition he got was staggering. I
mean, let's just run through the list. Please
do. OK, so in 2007, he gets the President's Award
from the Los Angeles Press Club. That's a big
deal. The National Hispanic Media Coalition gives
him an Impacto Award. OK, so he's being recognized
by both mainstream and Hispanic media groups.
Right. And then in 2008, the California Latino
Legislative Caucus, we're talking actual elected
officials, they give him the Latino Spirit Award.
Wow. So politicians are endorsing this supposedly
politically incorrect column. It just shows that
they understood he was doing something much deeper
than telling jokes. He was forcing a conversation
that needed to happen. But there is one award
here that just seems like the ultimate paradox.
The Association of Alternative News Weeklies
gave him best nonpolitical column. Twice. Twice.
How is a column tackling immigration and labor
policy nonpolitical? That makes no sense to me.
Well, that's the beautiful irony of it, isn't
it? I think it shows how the media establishment
defined politics at the time. If you weren't
writing a stuffy op -ed about tax brackets, it
wasn't considered politics. Because Ariana was
writing about culture and using humor, they filed
it under lifestyle. Even though culture is probably
the most political thing there is. Of course
it is. He was probably shaping more opinions
on immigration than half the political columnists
out there, all while being classified as a humorist.
The satire was his passport to get into these
serious topics without people's defenses going
up. Exactly. And that success naturally led to
expansion. In 2008, Scribner's publishes a book
collection also called Ask a Mexican. He goes
from newsprint to hardcover. That's a major step.
It is. And the syndication numbers really tell
the story. At its absolute peak, the column was
running in 39 different markets across the country.
39. So from one paper in the OC to nearly 40
cities. It was huge. You could be in Denver or
Houston and pick up the local Alt Weekly and
read Dear Gabacho. So 2008 feels like the high
watermark. He's got the awards, the book, massive
syndication. But the media business is, well,
it's brutal. It is. And the story of the column
from that point on perfectly mirrors the story
of print journalism itself. The Great Collapse.
The Great Collapse. If you look at those syndication
numbers, it's a terrifyingly steep graph. The
source material mentions an interview he gave
in 2017 where he talks about the death of journalism.
Yeah. By that point, the number of papers carrying
in the column had dropped from 39 down to around
12. From 39 to 12, that's more than two thirds
of his reach just. Gone. It's devastating. And
he even joked about needing to do a new census
just to figure out where he was still being published.
But it wasn't because people stopped reading
the column. Right. It was because the papers
themselves were dying. Exactly. The business
model of the Alt Weekly was built on classified
ads. And then Craigslist came along and just
wiped them out. And Facebook finished the job
on the ad revenue side. So you have this vital,
important piece of commentary. But the ships
carrying the message are sinking all around it.
It's such a bleak picture of that time. But the
story doesn't just trail off into nothing. It
ends with a bang, not a whimper. It really does.
It ends with a specific moment, a conflict that
says everything about the guy behind the column.
October 13th, 2017, Gustavo Arellano resigns.
But it's the why that matters. This wasn't about
money or a better job. No, this was a moral stand.
The owner of the OC Weekly at the time came to
Arellano, who was the editor by then, and gave
him a directive. And that directive was what?
Fire half of your staff. Wow. Just like that.
Look at your team, pick half and show them the
door. It's an impossible position for any leader
to be in. But Ariyama's response was incredibly
simple. He just said no. He refused to do it.
He refused. And when they insisted, he chose
to resign himself rather than fire the people
who worked for him. That takes a level of integrity
you just don't see very often to basically fire
yourself to protect your team. It's a profound
ethical choice. And it cemented his legacy. But
it also created a huge, messy problem. He walked
out the door. But what happened to his column?
What happened to Ask a Mexican? Right. Can you
just take it with him? Go start a Substack the
next day. He could not. And this is where we
get into the really important lesson about intellectual
property. OK, break this down because it's a
distinction a lot of people get wrong. So Ariana
wrote the words. He owns the copyright to the
individual articles he wrote. But the newspaper,
the OC Weekly. owned the trademark. And the trademark
is the brand name itself. Exactly. The trademark
is the name, the logo, the brand identity. Ask
a Mexican was considered a product of the paper.
They owned the title on the box. So when he left,
the name had to stay behind. It did. He built
this persona, this voice, this national brand
from nothing. The corporation owned the nameplate
on the door. It's kind of heartbreaking. It feels
like a story you hear with rock bands all the
time. The singer quits, but the label owns the
name of the band. It's the exact same principle.
He made it clear in interviews, you know, they
own the trademark, but they don't own me. They
don't own my voice. So could the paper have just
hired a new Mexican? Legally, they probably could
have tried. But in reality, no way. Because the
brand was him. His specific voice, his knowledge,
his humor, it was so unique. Any replacement
would have been seen as an imposter instantly.
The readers would have burned the place down.
So the trademark, the brand, becomes effectively
worthless without the creator behind it. Precisely.
The paper held the legal document, but he held
all the actual value. It's a fascinating standoff
between corporate ownership and creative identity.
It really is. So let's just recap this wild ride.
A one -time spoof from 2004. Becomes an award
-winning, nationally syndicated column that actually
shapes conversations on major issues. Its distribution
network then collapses as the newspaper industry
implodes. And it all culminates in 2017 with
an act of defiance where the creator walks away
on principle, leaving the trademark behind but
taking all the actual value with him. What an
incredible story. It really forces you to think.
It does. It leaves you with this kind of provocative
thought about identity and property. Which is
what? Well, if a company owns the trademark to
a persona, but the creator owns the voice, the
talent, and the soul, what is the brand actually
worth without the human who gave it life? A question
every creator should probably be asking themselves.
A great place to leave it. Thanks for this deep
dive. My pleasure. We'll see you next time.