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Hathaway Shirt & Canva’s Oops OOH
Lessons from David Ogilvy and a fun OOH treat.
Hi friends,
If you’re into copywriting, you sure would know who David Ogilvy was.
The man is called the father of advertising. A few months back I read the book “Ogilvy on Advertising.”
Brilliant and one of the books that I’d highly recommend if you want to become a copywriter.
One of my favorite ads from him is the Rolls Royce one.
I shared about it here.
But why stop there? Here is another study worthy of everyone reading and understanding.
Copywriting Example
The Hathaway Shirt
Most shirt ads in 1951 were boring. Generic models. Predictable poses. Copy that talked about thread count and fabric quality.
David Ogilvy said, "Screw that. Let's give people a mystery they can't solve."
C.F. Hathaway was a modest shirt company from Maine with a tiny $30,000 budget.
They were nobody. Just another shirtmaker trying to break into the national market.
But Ogilvy had a plan.
On his way to the photo shoot, he stopped at a drugstore and bought a few cheap eye patches for 50 cents each. He handed one to the model and told the photographer, "Just shoot a couple of these to humor me."
That eye patch changed everything.
The ad ran in The New Yorker for $3,176. Within a week, every Hathaway shirt in New York City was sold out.
But here's the genius part: Ogilvy never explained the eye patch.
No backstory. No dramatic reveal. No "This is why our hero lost his eye."
Instead, he let your imagination run wild.
Was this man a war veteran? A daring pilot? A sophisticated gentleman with secrets?
The eye patch created what Ogilvy called "story appeal" - it made people stop, stare, and invent their own narrative.
The campaign ran for decades. Hathaway became the second-largest shirtmaker in America. All because of a 50-cent prop that made people curious.
Takeaway? Sometimes the best story is the one you don't tell. Give people a mystery, and they'll fill in the blanks with something far more interesting than anything you could write.
Marketing Secret
Inside Jokes as Marketing Gold
Quick question: What's funnier? A joke everyone gets, or a joke only your tribe understands?
If you said the second one, you're onto something powerful.
That's exactly what Canva figured out with their "Oops OOH" campaign in London's Waterloo Station.
Most design software ads are predictable.
Happy people at computers. Clean interfaces. Professional stock photos.
Canva said, "Let's make billboards that only designers will truly get."
They created massive installations based on design clichés and inside jokes:
A billboard with Canva's logo literally bursting out of its frame (every designer has heard "make the logo bigger")
A landscape design awkwardly crammed into a portrait frame
A 3D e-bike being "dragged and dropped" onto the billboard
A whiteboard that erases itself in real-time
Pure magic for anyone who's ever opened Photoshop.
But here's the genius: these weren't just jokes. Each billboard demonstrated a real Canva feature.
The bursting logo? That's about flexible design templates.
The awkward landscape? That's the magic resize function.
The drag-and-drop bike? That's the intuitive interface.
The self-erasing whiteboard? That's the background remover tool.
The result? Thousands of photos shared online. Designers feeling seen and understood. A software brand that suddenly felt like it "got" their daily struggles.
This is product-led storytelling at its finest.
Instead of explaining features, Canva made them physical.
Instead of talking about benefits, they created experiences.
Instead of targeting everyone, they spoke directly to their tribe.
Here's how to use this:
Find the inside jokes in your industry. What do your customers complain about? What makes them roll their eyes? What phrases make them laugh or cringe?
Then turn those moments into content that says: "We get it. We're one of you."
Don't try to be clever for everyone. Be brilliant for your people.
Your homework this week: List three inside jokes or common frustrations in your industry. Then create one piece of content that acknowledges these moments. Watch your tribe light up with recognition.
Talk soon,
Alen.