(Spoiler: If your emails don’t sprinkle at least a few of these in, they’re fighting for attention unarmed.)
The midnight rabbit-hole that started it all
This February I had some free time on my hands. I took time off doing client work to enjoy my last few months in Thailand.
During that time off I did what any rational person (whose totally not unhealthily obsessed with copywriting btw) would do:
I binge-read an entire YEAR of emails from the biggest names in email copy, and people I consider to be masters of the craft. Ben Settle, Chris Orzechowski, Ramit Sethi, Andre Chaperon, Daniel Throssel, Joanna Wiebe and a few more.
The goal of this exercise?
I wanted to find the common techniques they all use to make their email copy more fun, engaging and persuasive.
My goal was do find a set of instructions I can give AI to make turn any boring ol’ email and turn it into “inbox Netflix”. Something that gets subscribers to come back for more.
There are a lot of little techniques and stylistic flourishes that I noticed in my inbox journey.
But 9 principles stood out as repeating over and over again. With every copywriter. Like clockwork.
I want to share them with you.
Today you’ll get the whole dossier:
- What the 9 principles are
- Why each one hijacks readers’ brains
- Exactly how to drop them into your next send
- Real-world snippets you can steal
Ready? Refill the coffee. This is a long one—but so is the line of subscribers hitting delete if you don’t learn this stuff.
Part 1 • The Musical Hooks (Principles 1-3)
“If the copy looks good in black-and-white but sounds like flat soda, you’ve already lost.” – One of the gurus, probably
1. Alliteration, Rhythm & Sound-Play
WHAT it is:
Alliteration is when you use a string of words that start with the same sound – think “Peter Piper picked a peck…” Rhythm is about the musicality of your sentences, the way they bounce and flow.
Sound-play is the umbrella term for all the little tricks that make your writing feel like a catchy song lyric instead of a tax return. It’s the difference between “good copy” and “copy that gets stuck in your head like a jingle you can’t shake.”
Why it works:
Brains love patterns. Repeating consonants or crafting a da-DA da-DA rhythm lights up Broca’s area like a Christmas tree, making your line sticky and shareable. It’s why you remember “Don’t dream it, drive it” but can’t recall the last five emails you got from your bank.
How to implement:
- Write your sentence.
- Read it out loud.
- Swap boring words for synonyms that start with the same sound.
- Tap your desk while reading—does it have a beat? Good.
Steal-this example:
“Sassy sales scripts that sell (without sounding slimy).”
“Busy bees buzzing about business.”
“Connect, create, and coax your audience to action.”
2. Relatable Analogies & Metaphors
WHAT it is:
Analogies and metaphors are the copywriter’s cheat code for making the abstract concrete. An analogy compares your idea to something familiar (“It’s like…”), while a metaphor just says it is that thing.
Both are shortcuts to instant understanding. They turn “confusing” into “crystal clear” and “meh” into “memorable.”
Why it works:
Abstract ideas strain working memory. A vivid comparison compresses complexity into a single mental snapshot—like zipping a giant file. Suddenly, your reader isn’t just reading—they’re seeing and feeling what you mean.
How to implement:
- Write the painful situation your reader’s in.
- Ask, “What does this feel like in normal life?”
- Swap the dry statement for your analogy.
Steal-this example:
“Trying to sell without a plan is like baking a cake without a recipe – messy and disappointing.”
“Your inbox is a jungle, and I’m here with a machete.”
“Closing a deal should feel like a high-five, not a root canal.”
3. Opening & Closing Loops
WHAT it is:
A loop is a story, secret, or benefit you tease at the start (“open the loop”) and then resolve later (“close the loop”). It’s the copywriting equivalent of a Netflix cliffhanger. You dangle a carrot, and your reader can’t help but chase it to the end.
Why it works:
Humans hate unfinished business (Zeigarnik effect). A teased secret kicks dopamine into curiosity overdrive until the brain gets closure. It’s why you binge-watch “just one more episode” at 2am.
How to implement:
- Tease early: “In a second, I’ll show you the mistake that tanked my open rates…”
- Close later – after a story or lesson.
- Never forget to actually close the loop, or trust evaporates.
Steal-this example:
“I’ll tell you the weirdest sales tip I ever learned… but first, a quick story.”
“More on that in a minute…”
“Remember that embarrassing mistake I mentioned? Here’s what happened…”
Part 2 • The Flavor Boosters (Principles 4-6)
4. Hyper-Specific Details
WHAT it is:
Hyper-specific details are those oddly precise, sometimes quirky facts that make your writing feel real. Instead of “I had a bad day,” it’s “I spilled coffee on my 2007 MacBook while wearing pizza-print pajamas.” The more specific, the more believable – and the more your reader feels like they’re right there with you.
Why it works:
Specificity = credibility. The oddly precise detail proves “I was there,” pulling readers into the scene and painting cinema in their head. It’s the difference between a blurry photo and 4K Ultra HD.
How to implement:
- Replace “I bought an old laptop” with “I eBayed a dented 2009 white-polycarbonate MacBook for $83.”
- Use sensory nouns: smells of cinnamon, the hiss of an espresso wand, etc.
Steal-this example:
“I spilled coffee on my 2007 MacBook while wearing pizza-print pajamas.”
“I once cold-called 37 people in a row and got rejected by every single one – except the guy eating a tuna sandwich.”
“My dog, Pickles, barked every time I said ‘sales funnel’ on Zoom.”
5. Humor & Playfulness
WHAT it is:
Humor and playfulness are the secret sauce that makes your emails feel like a chat with a clever friend, not a lecture from a bored professor. It’s not about being a stand-up comic – it’s about adding a wink, a nudge, or a little exaggeration that makes your reader smile (or at least not groan).
Why it works:
Laughter drops cortisol and spikes attention. Plus, if you can make someone smile, you slide into their “friends” folder instead of “vendors.” People buy from people they like – and nothing builds likability faster than a shared laugh.
How to implement:
- Punchline placement: build tiny tension, break it.
- Self-deprecate – it’s safer than roasting readers.
- Exaggerate a mundane scenario 10×.
Steal-this example:
“I’d rather wrestle a raccoon for the last slice of pizza than make a cold call.”
“If you’re allergic to fun, stop reading now.”
“My first sales call was so bad, the prospect tried to sell me something instead.”
6. Conversational Tone
WHAT it is:
A conversational tone is writing that sounds like you’re talking to a friend over coffee, not dictating a memo to the board. It’s casual, direct, and full of “you,” “we,” and “I.” It’s the opposite of stuffy, jargon-filled, or robotic.
Why it works:
Corporate-speak triggers fight-or-flight. Real talk feels like a WhatsApp chat with a pal—which lowers resistance and ups reply rates. When your writing feels like a conversation, your reader leans in instead of tuning out.
How to implement:
- Short sentences.
- Contract → do not ➔ don’t.
- Ask questions: “Ever hit send and instantly regret life choices?”
- Sprinkle ellipses…sparingly.
Steal-this example:
“You ever have one of those days where nothing goes right? Yeah, me too.”
“Let’s be real: nobody likes awkward silences.”
“Here’s the deal—I’m not here to waste your time.”
Part 3 • The Cultural & Connection Catalysts (Principles 7-9)
7. Pop-Culture & Timely References
WHAT it is:
Pop-culture and timely references are shout-outs to TV, movies, memes, or current events that your audience instantly recognizes. They’re the “in-jokes” that make your reader feel like you’re both in on the same secret.
Why it works:
Shared fandom = shortcut rapport. A Marvel nod tells readers, “We’re in the same tribe,” before you ever pitch. It’s a fast-track to trust and relatability.
How to implement:
- Skim morning headlines or trending memes.
- Ask, “Would at least 30% of my list ‘get’ this?”
- Tie the reference back to your lesson – don’t just name-drop.
Steal-this example:
“If you’ve ever felt like Michael Scott on a sales call, you’re not alone.”
“This strategy is more effective than a Taylor Swift breakup song.”
“Trying to sell with outdated tactics? Might as well fax your prospects a mixtape.”
8. Lists With a Twist
WHAT it is:
Lists with a twist are your standard bullet points, but with a punchline, surprise, or little joke at the end. They’re the difference between “Here’s what you get: 1, 2, 3” and “Here’s what you get: 1, 2, 3, and a free llama (okay, not really).” It’s about rewarding the reader for actually reading the whole list.
Why it works:
Lists promise scannability, but the twist rewards those who actually read, sparking a tiny dopamine hit. It’s a micro-moment of delight that makes your copy memorable.
How to implement:
- Deliver two legit bullets, then a curveball.
- Or end with hyperbole to jolt a grin.
- Works great in guarantees, bonuses, feature stacks.
Steal-this example:
“Here’s what you get: 1) More sales. 2) Less stress. 3) A smug sense of superiority over your competition.”
“Sign up today and you’ll receive: 1) Lifetime access. 2) Personalized feedback. 3) A free llama delivered to your door (okay, maybe not the llama).”
“Your membership includes: 1) Step-by-step training. 2) Supportive community. 3) The confidence to finally stop Googling ‘how to not sound awkward on sales calls.’”
9. Direct Reader Engagement
WHAT it is:
Direct reader engagement is when you break the fourth wall and talk straight to your reader. You call out their situation, ask rhetorical questions, or use asides that feel like a private conversation. It’s the digital equivalent of making eye contact and giving a knowing nod.
Why it works:
Second-person focus (“you”) shifts spotlight onto the reader’s internal movie – where persuasion actually happens. It makes your email feel like a one-on-one chat, not a broadcast.
How to implement:
- Start sentences with “You” or “Your.”
- Sneak in questions they answer in their head.
- Use cheeky asides – “(Yes, I see that eye-roll.)”
Steal-this example:
“If you’re reading this in your pajamas at 2am, this is for you.”
“You know that feeling when you hit ‘send’ and immediately regret it? Yeah, we’ve all been there.”
“Quick question: what’s the weirdest thing you’ve ever said on a sales call?”
Common Objection, Met & Melted
“Amir, this is cute, but does ‘fun’ sell? I sell enterprise compliance software, not TikTok merch.”
Fair. Here’s the data-wrapped truth:
- Entertainment lifts open rates (Curiosity + likability = more clicks).
- Higher opens multiply deliverability (your sender score parties).
- Stories + humor drive memory, and remembered brands get shortlist status when budgets unlock.
Even the button-down B2B folks are human after 5 p.m.—write for the human, not the badge.
Your 9-Point Secondary-Reward Checklist
Copy this into your doc before you hit “send”:
Musical touch? (Alliteration/Rhythm)
Analogy that clicks instantly?
Loop opened…later closed?
One oddly-specific detail?
At least one grin trigger?
Reads like coffee chat?
Timely or cultural nod?
List with a surprise?
Did I speak straight to you?
Hit 5/9 and you’re above average. Nail 7+ and your subscribers may actually forward the thing (rare but glorious).
Next Step—Steal the Prompt That Automates All This
Entertaining copy’s a skill—or a prompt away. I’ve wrapped the TALE structure plus today’s nine fun-factor checkpoints into a single copy-and-paste ChatGPT prompt. Grab it free, try it tonight, and watch your next email sparkle harder than a Taylor Swift surprise album drop.
[Get the prompt here]
Keep it fun, keep it human, and I’ll see you in their “favorites” tab.
—Amir