- Harry Dry is a copywriter and marketer who runs the newsletter Marketing Examples and teaches copywriting through his course. In this episode, he breaks down his entire approach to writing copy that works—copy that is visual, falsifiable, and unique to the brand. He walks through real ads, live examples of his writing process, and the principles behind why some lines stick and others disappear.
Harry’s Three Rules for Writing Copy
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Can I visualize it?
- If you can’t see it in your mind, you won’t remember it. Concrete images beat abstract language every time.
- Example: “Seamless transition” is forgettable. “Charging pitbull” sticks because you can picture it.
- How to apply it: Take an abstract phrase and “zoom in” until it becomes a concrete object or scene. “Regain fitness” becomes “Couch to 5K”—a real, visual, downloadable program name that became the most popular fitness app of all time.
- Another example: Instead of “worn by pretty people in big cities and old people in small towns,” New Balance says “worn by supermodels in London and dads in Ohio.” Specific, visual, and funny.
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Can I falsify it?
- A sentence that can be proven true or false makes people sit up. It puts the writer’s head on the chopping block.
- Example: Galileo saying “the earth spins around the sun” got him house arrest. Saying “the earth has a harmonious connection with a celestial object” would have gotten him a beer.
- How to apply it: Don’t talk—only point. Instead of saying someone is “intelligent,” say “reads on the tube.” Instead of “good-looking,” say “6’2”, looks like Ryan Gosling.” These are true or false, not subjective adjectives.
- When selling gold, don’t say “gold is a great investment.” Point at the 50-year chart going up. Point at Warren Buffett’s portfolio. Let the facts speak.
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Can nobody else say this?
- If a competitor could run your ad tomorrow, it’s not good enough. The best copy is bespoke to the brand.
- Example: Volkswagen’s old ad—“Your car has five numbers on the speedometer. Volvo has six. One could get the impression that the people who made your car lack a little confidence.” No other car company can say that. It’s visual, true, and unique to Volvo.
- Another example: Corvette’s “They don’t write songs about Volvos.” Only Corvette can claim that country singers romanticize their car.
Why Learn Copywriting?
- It’s the number one skill in marketing. Strip away the branding from Snickers and a failed bar like Fuse—they taste the same, but one sells billions because of copy like “You’re not you when you’re hungry.”
- Startups are the same. Samsung and Apple both have app stores and great cameras, but 17 out of 20 American teens choose Apple because, as Ogilvy said, “We don’t choose the whiskey, we choose the image.”
- Positioning can outsell a better product. Dave Kitson was a mediocre footballer with one England cap. His book outsold Beckham, Lampard, Gerrard, and Owen combined—because he wrote it as “The Secret Footballer,” exposing behind-the-scenes Premier League stories the stars wouldn’t tell. The product was worse, but the positioning was unbeatable.
The “One Mississippi, Two Mississippi” Test
- Show someone your ad. Count “one Mississippi, two Mississippi.” If they don’t get it in two seconds, it’s not working.
- Great copy communicates instantly. “1,000 songs in your pocket” works because it’s visual (pocket, not “media player”), concrete, and surprising—even though it’s technically a metaphor (metonymy).
- The Economist’s “I’ve never read the Economist. Management trainee, aged 42” works because it tells a story in two lines, uses the brand’s red, has no logo or image, and doesn’t look like an ad—so you actually read it.
Harry’s Process for Writing an Ad
- Start with a seed. Harry saw a tweet: “The difference between 1% and 2% is not 1%—it’s 100%.” He knew that was the core argument for learning copywriting.
- Find a visual structure. He remembered a Volkswagen ad that contrasted “ordinary car” vs. “Volkswagen” with two columns of checkboxes. He borrowed that layout.
- Rewrite 20+ times in Figma. He doesn’t write in Google Docs—he designs and writes simultaneously, because copy and design are inseparable. He needs to see exactly how it will look.
- Iterate through problems. He wanted parallelism in the headings (“The corporate way” vs. “Learn copywriting”), but “learn to write” was too long. He shortened it, moved it to the header, and restructured around it.
- Spitball freely. He writes bad options without judging: “Go fool Zuckerberg,” “Roll Monopoly dice,” “Spaghetti at war.” This gets the “dirty water out of the tap” until clean ideas emerge.
- Add design last. He bolded key words, added rhythm (“twice the cash, twice the staff, twice as much”), and commissioned illustrations on Fiverr—iterating with the artist until the praying guy looked like an idiot and the writer had a typewriter and light bulb.
- Final ad: “Want to grow twice as fast? You have two choices. Throw money and pray: raise twice the cash, hire twice the staff, spend twice as much on ads, cross both your fingers. Or learn copywriting: increase conversions from 1% to 2%. That’s twice as many.”
Another Ad: Reframing the Ask
- “Marketers, you’ll spend 22,000 hours of your career writing. Spend two learning how to do it well.”
- The seed: marketers write ~4 hours a day × 300 days × 30 years = ~22,000 hours.
- The trick: instead of “spend 2 hours learning copywriting” (sounds like a cost), he reframes it as “you’re already spending 22,000 hours—just spend 2 of them wisely.” The parallelism of “22,000” and “two” makes it punchy.
On Facts
- Harry loves facts. “Behind every fact, there’s a story.”
- A fact is precise and true, but not inherently interesting—you have to work with it. “350 million Americans” is boring. But “the flight from New York to London is only 6 hours—too short to sleep, too long to be easy” turns a fact into a story.
- Facts ground your writing in reality. Instead of saying “inequality,” show the graph. Instead of “Tiger Woods didn’t want it,” say “he hit 7 fairways today vs. his usual 11.”
- Start with a fact, then build from there.
How Harry Writes His Newsletter
- It’s a letter, not a blog. He starts with time, place, and what’s happening: “It’s 3:47 a.m. I’m in the big smoke alone. Laptop, green tea, looking at the whiteboard like a dozy dog.” This comes from J.K. Rowling’s Chamber of Secrets opening.
- Every example has conflict. Before/after, problem/solution, “here’s how everyone else does it vs. how this one does it.” Example: Loom was just another screen recorder until they repositioned as “async video messaging” because “remote communication sucks.” That conflict made them worth more than the entire screen recorder category.
- Every paragraph is two lines max. Short paragraphs are “like monkey butts—easy to swing between.” If a paragraph is three lines, he’s probably not explaining himself well. It also gives lines room to breathe.
- He writes multiple versions. He’ll write the same paragraph four or five ways, then show them to his brother, who can pick the best sentence from each. The freedom to be bad in early drafts lets him find what’s good.
How to Write Simply
- You can’t write simply—you can only rewrite simply.
- Kaplan’s Law of Words: Any words that aren’t working for you are working against you. Cross them out. This applies to ideas too: the strength of an idea is inversely proportional to its scope. “We make jeans” beats “we sell jeans, t-shirts, socks, and have dressing rooms.”
- A good paragraph is like a burrito: You should be able to throw it to someone and it shouldn’t come apart. If you can pull out a sentence and the paragraph still works, that sentence shouldn’t be there.
- Structure is wildly underrated. Divide things into clear buckets with parallelism. Copywriting = who are you talking to, what are you saying, how are you saying it. Getting 10,000 readers = first get 100, then get the next 9,900. Structure is chapters in a book—without it, everything is a heavy, undifferentiated mass.
On Standards
- “Your standards are your work.” Nine out of ten ideas don’t make it out. If it’s not good enough, no one sees it.
- How do you know something is good? You walk around the garden, come back, and can’t take anything away. “Worn by supermodels in London and dads in Ohio”—you can’t add or remove a word. It just is.
On Conflict in Stories
- Conflict is the “but” in a story—what went wrong, what’s the tension. You don’t need to write the word “but”; just show the friction.
- Example: “I woke up at 8:52 a.m. My mom ran up the stairs and said I couldn’t do the interview in blue shorts. I showed up and David asked why I had longer trousers on. I hadn’t brought any.” That’s conflict—small, real, human.
On AI and Copywriting
- AI is a tool, like a typewriter or laptop. It doesn’t make work better on its own—only taste does.
- AI can’t have conviction or experience. Ogilvy pulled “At 60 mph, the loudest noise in a Rolls-Royce is the electric clock” from a motor magazine because he had the taste to recognize it and the conviction to run it. AI can’t sit in the car.
- Great writers draw from lived experience: Bukowski worked as a postman for 20 years, then wrote Post Office. Kerouac lived on the road for seven years, then wrote On the Road in three weeks. Michael Lewis spent years on Wall Street before writing The Big Short.
- AI is predictive—it rearranges what’s already been said. A good writer arranges words in ways that haven’t been laid out before. AI doesn’t believe anything, so it can’t tell you something surprising.
Silence and Action
- Harry runs on “silence and action.” He does writing retreats with Cultural Tutor where no one talks until dinner. No TikTok in the morning, no earphones on walks—just silence, then focused work.
- If he wakes up and scrolls, the day is drudge. If he wakes up in silence, he gives himself a shot at writing something brilliant.