Want your copy to hit harder? These three rules from Harry Dry show you how to ditch clichés and write things only you could write.
I’m writing this while standing at my new desk. Not because I want to impress you (okay, maybe a little), but because apparently, standing helps me think. Sitting is for copywriting, standing is for thinking. Does anyone else swap positions when they’re stuck, or is it just me doing an awkward shuffle mid-draft?
Anyway, I just watched a video that’s basically a cheat code for anyone who writes copy, emails, landing pages, LinkedIn posts, you name it. David Perell interviews Harry Dry, who writes the Marketing Examples newsletter.
If you haven’t heard of Harry, fix that. The guy turns boring marketing into something you’d actually read for fun.
Most interviews are two people talking and a video camera pretending you want to watch the whole hour. Not this one. Think live ad copywriting, on-screen visuals, even games. If you’re like me and your attention span is somewhere between “goldfish” and “scrolling TikTok,” you’ll appreciate this format.
Harry’s three rules for every sentence go like this:
If you can’t say yes to all three, you’ve probably written fluff.
Most people nod along here. “Yeah, yeah, no fluff, be unique, got it.” But here’s the real test. Let’s walk through a quick example.
Fluff
“We deliver innovative solutions tailored for your needs.”
Can you visualize it? Not really. Prove it? Good luck. Could anyone else write that? Absolutely.
Open LinkedIn, you’ll see it fifty times before lunch.
Not Fluff
“Our team builds 3-step onboarding flows that get your clients from ‘signup’ to ‘first payment’ in under 24 hours – ask Sarah at Acme, she shaved a week off her onboarding last quarter.”
Visualize it? Yes, you see the steps. Prove it? Call Sarah. Is it unique? Unless someone else is onboarding Acme’s clients, you’re good.
That’s the difference. Once you see it, you can’t unsee it. Your copywriting will start sounding less like a robot-CEO and more like a human who actually does things.
Quick detour. David Ogilvy nailed it when he said, “It isn’t the whiskey they choose, it’s the image.” You’re not selling a better product, you’re selling a feeling, and words are how you do that.
Your company, your service – it’s not that different from the next one in your industry. But if you can make people feel something, you win. That’s where copy comes in. It’s the difference between “Here’s our flat monthly fee” and “Here’s the last time you were blindsided by an agency invoice – never again.”
Watching Harry write an ad live is like watching someone solve a Rubik’s Cube while explaining their moves. You see the edits, the rewrites, the dead-ends, and the little spark when the right sentence finally shows up.
This video isn’t your typical interview – live ad writing, visuals, and even games make it engaging.
There’s a moment where Harry is given a random product and has to write an ad for it on the spot. He pulls up the publishing tool he’d actually use (not a blank Google doc, but the real thing). Here’s the secret: write in the medium you’ll publish on. If it’s a newsletter, write in the newsletter software. (Note to self, Jason!)
This sounds small, but it matters. You get the spacing, formatting, and even the little quirks of each platform right from the start. No more copy-paste disasters at the last minute.
Harry’s trick for killer subject lines? Write twenty or more versions. Not to torture himself, but because the first dozen will be predictable, boring, or just plain bad. Only after you get those out does the gold show up.
Bleed the tap: write 20+ subject lines to get rid of the bad ones so the last few are gold.
Try this next time you’re stuck on a subject line or headline. Set a timer for ten minutes. Write as many as you can, no editing. The weird ones, the bad puns, the “no way I’d ever use this.” Then look at the last five. One of them will make you smile (or at least cringe less).
When you stare at your own copy too long, it blurs. You stop seeing typos, clichés, or places where you sound like everyone else.
When stuck, get feedback from friends (even on Whatsapp!) to spark new ideas.
Seriously, send it to a friend, a client, your mom (if she’s honest). Doesn’t matter. Someone who’ll say, “This doesn’t sound like you,” or, “I don’t get it.” Fresh eyes will save you hours.
This video’s gold-nugget-to-length ratio is off the charts. Bookmark it and take notes.
If you want to put this into practice, pick a topic: your next offer, a new service, even your next LinkedIn post. Write 20 subject lines or headlines. Bleed the tap dry. Then run your favorites through Harry’s three rules:
If not, back to the tap.
That’s it for today. If you want more copywriting shortcuts and behind-the-scenes breakdowns, schedule a 15-minute call with me. Let’s make your copy sound like you, and actually get results.
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