A Couple of Classic Stories

There are a bunch of classic stories that have circulated around the advertising community for years. 

One of my favorites involved Donald Trump:

When Donald Trump launched Trump Shuttle in 1989, he hired Chiat/Day, the hottest ad agency at the time, to create the ads. They delivered their signature bold, creative work, but Trump hated it.

Trump fired off an angry letter on his gold-embossed letterhead. Jay Chiat simply sent it back with a handwritten note: "Donald, I thought you should know that some lunatic has stolen your stationery."

Trump fired them the next day.

And here's one specifically for the copywriters:

A client once hired a renowned copywriter, then proceeded to rewrite all their work. When the client joked, "I guess I'm just a frustrated copywriter," the writer shot back: "No, I'm a frustrated copywriter. You're an asshole."

 

Typo?

In 2018, Visible, a cell phone service provider, advertised “unlimited massages” instead of “unlimited messages” in Denver, its hometown market.

The campaign centered on 150 outdoor ads around Denver promising “unlimited massages, minutes, and data” for $40 a month. Of course, when a company makes a “typo”, the internet attacks like a lion spotting a limping gazelle. Screenshots flew. Hashtags appeared. Snarky advice like, “This is why you proofread” was offered.

“Free massages?” they said. “Sign me up.”

Visible leaned into it. They responded with jokes on social media. “We’re all about eliminating pain points.” “Are we sending mixed massages?” That kind of thing.

Then a few days later they delivered the punchline: the typo was deliberate. And if you showed up at Denver Union Station on specific day, they’d actually give you a free chair massage. CBD oil if you wanted it. Towels, eye masks, kombucha. The whole spa-day starter pack.

The whole thing feels like a magic trick designed for social media. The typo isn’t really a typo. The mistake is the point. It’s bait, engineered to trigger the internet’s favorite reflex: “Look at this dumb thing.”

But I’ll give Visible this: at least the payoff was real.

Too many marketing stunts end with nothing but a tweet thread and a vague sense that you’ve been manipulated. These people actually gave massages. Multiple massages, apparently, if you wanted to stand back in line like a kid riding the same roller coaster.

There’s something human about that. A "typo" that becomes a joke that becomes a real-world event where strangers sit in folding chairs getting their shoulders kneaded.

Which, if you think about it, is probably the closest modern advertising gets to art: a small absurd moment where language slips, the internet notices, and suddenly a phone company is handing out CBD massages like it’s running a pop-up spa.

I’m still not convinced the world needed this … but, from my point of view, if you’re gonna manipulate my attention with a typo, at least bring a massage therapist.

The NY Times: AI vs Human

In March 2026, the New York Times ran a quiz where readers picked AI-written passages over human ones. 

My first reaction wasn’t outrage or awe. It was a long, tired “yeah… that tracks.”

Not because I think machines have suddenly developed a soul. But because I’ve spent enough years reading things online to know most writing isn’t exactly brimming with one to begin with.

We like to pretend there’s this sacred line between “human writing” and everything else, as if every article comes straight from someone’s inner life … messy, vivid, earned. But a lot of it? It’s just clean sentences doing their job. Functional. Like airport signage. Nobody cries over Gate B12.

So when people say readers couldn’t tell the difference, I don’t hear “AI has arrived.” I hear: “Most writing was already halfway there.”

And honestly, the results make perfect sense. If you strip away the author’s name, the publication, the little halo of credibility we like to place over certain bylines, what’s left?

Rhythm. Clarity. Momentum.

AI is very good at those things. It’s like a cover band that never misses a note. Tight. Polished. Slightly eerie if you stare too long.

But here’s the part that interests me more: the gap between factual and opinion writing. People preferred AI for the clean, informational stuff, but it lost ground when things got personal.

Of course it did. Because information is about getting somewhere. Opinion is about having been somewhere.

And you can feel that difference, even if you can’t always articulate it. It’s the difference between a map and a story about getting lost.

The problem is, a lot of modern writing, especially online, doesn’t really do either. It hovers in this strange middle zone. Competent. Inoffensive. About as memorable as a receipt.

That’s the writing AI is quietly replacing. Not the brilliant stuff. Not the strange, voicey, slightly unhinged essays that make you stop and reread a sentence just to see how it was built.

It’s replacing the middle.

Which, if I’m being honest, deserves to feel a little nervous.

_______________________

Who’s a Better Writer: A.I. or Humans? Take Our Quiz. March 9, 2026 Kevin Roose and Stuart A. Thompson

New Tech, Old Terms

 

Notice how much of today’s new technology is named after old technology?

Like your phone. It’s a small, hand-held computer that includes a phone app. And the actual calling part (the reason we named it a phone) might be the least important thing it does. Yet we still call it a phone.

Same with your ring tone. Nothing rings. There’s no bell, just a digital chirp chosen from a menu with choices like “Marimba” and “Cosmic Dolphin.” But we still say the phone is ringing, because once upon a time phones had little bells that actually rang.

And when we’re done with a call, we “hang up” … because in yesterday’s technology when a call was over, you’d hang up part of the phone on a little hook. A far cry from tapping a button on a handheld device.

For privacy, you can “turn” the ringer off, even though there’s nothing to turn, just a tap on a screen. Why? It goes back to the knobs and valves on gas lamps (when controlling technology required at least one minor muscle group).

Listen to podcasts on your phone? The name podcast comes from combining part of the name of the now obsolete iPod and a radio term: broadcast. And radio stole broadcast from a farming practice: to cast your seeds broadly

Technology sprints forward like it’s late for something important. Language lags behind, walking with a cane, refusing to update its software.

I’m sort of comforted that all this talk of living in the future is grounded in vocabulary from the past … like hand-me-down clothes that somehow still fit. Makes the scary part of technology innovation seem safer: stubbornly human, messy, sentimental, and slow.