Harry Dry's Advice on Copywriting: Three Rules That Make Every Sentence Work

Harry Dry runs Marketing Examples, a newsletter with over 130,000 subscribers. It started as a side project cataloging the best marketing tactics he could find. Each example was short, visual, and actionable. No fluff. No theory. Just breakdowns of what worked and why. David Perell called him "the best copywriter I know."

Dry's writing advice comes from his appearances on the How I Write podcast, an Upgrow masterclass on copywriting, a VeryGoodCopy interview, Sproutworth analysis, a Growth in Reverse profile, and a Story Rules breakdown of his methods.

Three Rules for Every Sentence

Dry tests every sentence against three questions. Can I visualize it? Can I falsify it? Can nobody else say this?

If a sentence passes all three, it works. If it fails even one, it needs rewriting. "You get three nos, you've probably written a lot of rubbish. You get three yeses, you're on to something."

Can I visualize it? The reader should see a picture in their mind. Dry demonstrates this with a game. He reads six words: seamless transition, charging pitbull, muscly Irishman, better way, leg of lamb. You remember the pitbull, the Irishman, the lamb. You forget the rest. Why? "You remembered the ones which you can visualize."

Abstract is intangible. "You can't drop a better way on your foot. It just fades away. But if you try and drop a muscly Irishman on your foot, it hurts." Concrete beats abstract every time.

Can I falsify it? A falsifiable statement can be proven wrong. That means it is saying something specific enough to be tested. Dry uses a dating analogy to explain this. Try to set up your single friend on a blind date. First round: you can only use subjective descriptions. Good-looking. Funny. Smart. Nobody believes you. Second round: you can only state things that are true or false. Six foot two. Looks like Ryan Gosling. Reads on the tube. Now you are convincing.

"Don't talk. Only point." Point at the graph. Point at the evidence. Get off the adjective trail.

Can nobody else say this? Jim Durkee put it best: "Never write an ad a competitor can sign." Dry cites this constantly. If you swap out your company name and the copy still works for a competitor, it is generic. Generic copy does not persuade. It just fills space.

The New Balance Example

Dry's favorite example is a New Balance tagline: "Worn by supermodels in London and dads in Ohio."

Run it through the three rules. Can you visualize it? Yes. You see a model on a London street and a dad at a barbecue in suburban Ohio. Can you falsify it? Yes. Either supermodels wear them or they do not. Can nobody else say this? Absolutely. Nike cannot say this. Adidas cannot say this. Only New Balance occupies that specific cultural position.

"You can't add a word to that ad and make it any better. You can't take away a word and make it any better. It just is."

The tagline also shows how to zoom from abstract to concrete. You could have written "worn by pretty people in big cities and old people in non-big cities." But supermodels and dads in Ohio? Everyone can see that. The juxtaposition makes you laugh. That is the difference between adequate and unforgettable.

The Zoom-In Test

When copy is too abstract, Dry has a specific technique. Draw a line down the left side of a sheet of paper. Write "abstract" at the top and "concrete" at the bottom. Write the abstract phrase at the top. Then rewrite it, over and over, asking "what do I actually mean here?" until you arrive at a concrete object.

"Regain fitness" is abstract. What do you mean by regain? Getting off the couch after six months. What do you mean by fitness? Running. How far? 5K. From "regain fitness" you arrive at "couch to 5K" - the name of the most popular fitness program of all time. Made by a Boston TV producer, not Nike or Adidas. It stuck because it was concrete.

A Great Sentence Is a Good Sentence Made Shorter

Dry quotes this as his core editing principle. Every draft starts too long. The job of editing is subtraction. Not adding more ideas. Removing the words that do not earn their place.

This connects to what Dry calls Kaplan's Law: "Any word that isn't working for you is working against you." There is no neutral. Every word either pulls the reader forward or slows them down. Dry loves this law so much he invented his own corollary: "Harry's Law of Words: you aren't taking Kaplan's law of words seriously enough."

The same principle applies to ideas. "The strength of an idea is inversely proportional to its scope." This is why "and" on a landing page is almost never a good thing. "We sell jeans and t-shirts and socks." Compare that to Hue Denim: "We make jeans." That is it. Do one thing well.

"You know a paragraph is ready to ship when there's nothing left to remove." Not when it sounds good. Not when it feels complete. When you cannot take away another word without losing meaning. That is the finish line.

Short Paragraphs and Simple Sentences

Since March 2021, Dry has not written a paragraph longer than two lines. Three reasons. Short paragraphs are "like monkey bars. They're easy to swing between." People read on the train. They are not focused. Help them swing.

Second, if a paragraph runs three lines, there is a good chance he is not explaining himself well enough. Cut it down. Third, he likes giving lines room to breathe. A good line deserves space around it.

His editing process: write a sentence or paragraph. Copy and paste it. Write it again differently. Copy and paste. Write it again. End up with four or five versions. Pick the best one. "The freedom to do it wrong allows me to actually be a bit different, try my own way, and do it right."

He shows these versions to his brother, who edits everything he publishes. One paragraph gets vague feedback. Three versions of the same paragraph get precise feedback. "Use that sentence but put it in that one."

Write Like Your Customer Talks

Great copy reads like the customer wrote it. Not because you are dumbing it down. But because you are using their words, their frustrations, their exact phrases. Talk to customers. Read their reviews. Join their forums. Copy their language.

Dry puts it this way: talk to them, not at them. Most marketing copy talks at the reader. It announces. It declares. It uses corporate voice. Good copy sounds like a conversation. It sounds like someone who understands the problem because they have experienced it.

Structure Through Dividing Lines

Dry is obsessive about structure. He breaks big concepts into numbered parts using what he calls "dividing lines and parallelism."

Copywriting is big and scary. So he divides it: who are you talking to, what are you saying, how are you saying it. Three buckets. An essay about getting readers becomes two parts: "things that don't scale, 100 readers" and "momentum, next 9,900." That is the structure.

"It's like a book without chapters. Imagine that. It's long. It's heavy. Chapters are the structure of the book." Structure makes content holdable.

The Dave Kitson Principle

Dry tells a story about Dave Kitson, an unremarkable English footballer with one England cap and a forgettable career. Kitson wrote a book that outsold David Beckham, Frank Lampard, Steven Gerrard, and Michael Owen combined.

How? Positioning. Beckham and Gerrard wrote about their glorious careers. Kitson could not do that. But he had been inside the Premier League. So he wrote about what it was really like. Gambling addictions. What happens when England goes abroad. How many drinks. Behind-the-scenes stories the stars would never tell. He published it as "The Secret Footballer."

"That's copywriting. It's doing more with words. Kitson's product is objectively so much worse than David Beckham's. But just by positioning it, just by a little bit of storytelling, he could outsell him." The lesson: find what you can say that nobody else can or will.

Taste, Conviction, Experience

Dry is clear about what AI cannot replace. David Ogilvy pulled the Rolls-Royce headline from a motor magazine: "At 60 miles an hour, the loudest noise coming from the new Rolls-Royce is the ticking of the electric clock." It increased sales by 50%. Why did Ogilvy choose that line? Taste. Why did he commit to it as the headline? Conviction. Where did the line come from? Someone sat in the car, drove it at 60 mph, and noticed the clock.

"What's writing? You see something, you believe something, you write about it. Any kind of robot can't see anything and it doesn't believe anything."

Bukowski worked as a postman for 20 years and wrote Post Office. Kerouac lived on the road for seven years and wrote On the Road in three weeks. Sylvia Plath worked as an intern at a New York fashion magazine. Her character Esther Greenwood? A disillusioned intern at a New York fashion magazine. Experience produces the details that make writing specific. Without it, you are "gumming together long strips of words already set in order by somebody else."

Key Takeaways

• Test every sentence: can I visualize it, can I falsify it, can nobody else say this?
• Use the zoom-in test. Rewrite abstract phrases until you hit concrete objects.
• A great sentence is a good sentence made shorter. Cut until nothing is left to remove.
• Kaplan's Law: any word not working for you is working against you. No word is neutral.
• Keep paragraphs to two lines or fewer. Short paragraphs are monkey bars.
• Write multiple versions. Show them to an editor. Better feedback follows.
• Never write an ad a competitor can sign. Find the Dave Kitson angle.
• Structure through dividing lines and parallelism. Make big ideas holdable.
• Taste, conviction, and experience cannot be automated. They come from seeing and believing.

Dry's three rules are a checklist for editing, whether you are editing yourself or editing AI output. AI diffs let you test each sentence against these rules and accept or reject changes one by one. The best writing advice always comes back to the same idea: say something specific, say it briefly, and make sure only you could have said it.

This post draws from Dry's appearances on How I Write, Upgrow, VeryGoodCopy, Sproutworth, Growth in Reverse, and Story Rules. Athens is an AI writing editor that shows every change as a diff - so you can apply Dry's three rules to every AI suggestion and keep only what passes.