Welcome to the 139th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Benefits vs. Payoffs

• AI Tip: Claude’s memory can save you from re-briefing

• How to Hire a Freelance Copywriter Who’s Already Booked (via Copywriter Collective)

• FTC Puts Personalized Pricing Practices on Notice (via MarTech)

• Copywriters have a fundamentals issue (via Dustin Dooling)

• Podcast Pick: DTC vs B2B Marketing

• Swipe File Additions

• Job opportunities

Copy Tip of the Week

A benefit is a fact. A payoff is a scene.

“Saves you time” is a benefit. True, useful, and completely forgettable, because nobody’s life gets better in the abstract. Nobody lies awake wanting “more time” — they want what the time gets spent on.

“So you can actually eat dinner with your kids before they’re too old to want to” is the payoff. Same fact. Now it’s a moment your reader can see themselves in.

Read your benefit line, then ask “so what happens because of that?”

If you can answer in one more sentence, you haven’t hit the payoff yet — you’ve hit a fact that has a payoff hiding behind it.

Keep asking “so what” until the answer is a specific person doing a specific thing at a specific moment. That’s the floor. You can’t go “so what” past a scene.

Most copy stops one layer too early, because the benefit already feels like an accomplishment. It named the value! It’s true! But “true” isn’t the bar. The bar is: did the reader picture something?

Run this on your last promo. Whatever benefit you led with, push it one more “so what” and see what shows up.

AI Insight of the Week

Claude can carry stuff across chats — your preferences, what you’re working on, how you like things explained.

Tell it once (”when I say ‘meh,’ cut it down and make it more conversational”), and you stop re-explaining your voice every session.

Here’s the part that trips people up, though: it’s not logging your words in real time. It’s running a background process, periodically, that boils your chat history down into a handful of patterns. Not a transcript. A summary.

So if something you said doesn’t show up later, that’s not necessarily a bug:

• It takes a beat — a correction won’t always register in your very next message.

• It’s hunting for patterns, not jotting down one-offs. Phrase the thing as a standing rule (”from now on, always...”) instead of a passing comment, and it has a much better shot at sticking.

• If it actually matters, don’t rely on memory alone. Put it in the prompt too.

Say it once. Just say it clearly enough that once is enough.

Must-Read Articles

Podcast/Video Pick of the Week

DTC vs. B2B Marketing: Why the Buying Psychology is so Different (via Brain Driven Brands)

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Rob Hill’s framing of the two buying psychologies reorganizes how you think about a brief: consumers buy with a “no regret” strategy (don’t want to feel stupid), while B2B buyers operate on “don’t get fired” (it’s not their money, so risk aversion — not desire — drives the decision). He also breaks consideration into problem-aware, solution-aware, and product-aware phases, and argues you can’t shorten someone’s buying cycle.

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CHEWY

Format: Email
Why I like it: This is what I’d label an “evergreen email.” It can work any time of the year. But from the subject line to the category copy, it was packed with pet-driven personality. Loved it!

FLAMINGO ESTATE

Format: Email
Why I like it: “Take back your senses” and “No more optimization” and the “Smell a tomato” CTA all had me nodding my head. (P.S. there were several moving elements in this email, so be sure to view it here).

VIOME

Format: Facebook Ad
Why I like it: The way they leveraged whitespace to draw attention to their ‘breakthrough’ supplement. The primary text for the ad is great positioning too.

Job Opportunities

• DTC Email Copywriter (Stimulate)

• Copywriter (Patrick Ta Beauty)

• Product Page Copywriter (SULLIVAN)

• Copywriter, Credit Card (Snap Finance)

• Direct-Response Ad Copywriter for Silvery (Ventura Brands Oy)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 138th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Define Your Voice Pillars

• AI Tip: Stop describing your voice. Show it.

• The Email Problem You’re Not Seeing (via Sarah Fasuyi)

• What Agencies Want from a Copywriting Agency (via Copywriter Collective)

• Inside the creator economy’s AI reckoning (via HubSpot)

• Video Pick: The 3-Step CTAs Formula for Conversion ****

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

“Confident” is not a rule you can follow.

So, here’s what turns it into one…

Almost any copywriter can confirm that every “brand voice guide” has a word like this.

Confident.
Bold.
Playful.
Warm.
Whatever.

The problem? A word isn’t instructions.

Tell a writer “be confident” and they’ll apply their own interpretation to it.

The fix? Turn that “word” into a defined voice pillar.

A real Voice Pillar has three parts:

1. the word;

2. a definition

3. and a do/don’t

That’s what lets a writer actually WRITE from it, instead of guessing around it.

Let’s continue with our “confident” example.

On its own, the word is useless. But turn it into a pillar, and it looks like this:

Confident: States what’s true without hedging. Never apologizes for having a strong point of view.

Do: “This works. Here’s why.”
Don’t: “We think this could maybe help, depending on your situation.”

Now a writer isn’t guessing because they’ve got a test.

Does this line hedge? Cut the hedge.

A mood board tells a writer how the brand feels. A pillar tells them what to do about it.

That gap is the whole system.

Six lines like that – one per pillar – do more for a brand’s voice than a 3-page brand book full of adjectives ever will.

AI Insight of the Week

Stop describing your voice. Show it.

When you ask an AI to write “in your voice,” you’re handing it a vague brief.

“Conversational.”
“Punchy.”
“Less corporate.”

Those words don’t mean the same thing to the model that they mean to you — so it fills the gap with its own defaults, which is exactly why AI copy all sounds the same.

Instead of describing your voice, hand it a real edit.

Before: “We’re excited to announce our new feature that will help streamline your workflow and save you valuable time.”

After (your actual edit): “New feature. It saves you time. That’s it.”

Paste both into the chat and say “match this and do that going forward.” Now the model has something concrete to copy: where you cut words, how short your sentences run, what you swap in for corporate filler.

It’s still pattern-matching, you’re just choosing whether it matches your fuzzy adjectives or your actual sentences.

Must-Read Articles

Podcast/Video Pick of the Week

The 3-Step CTAs Formula for Conversion (via NN/Group)

Why I recommend it: Most weak CTAs aren’t a design problem — they’re just missing a step. Taylor Dykes breaks the formula into three parts: an actionable verb, a clear signal of what happens next, and a stated payoff for clicking, which is why “Learn More” underperforms and “Get your custom price in 30 seconds” doesn’t.

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AUTODESK

Format: Billboard
Spotted By: Cole Schafer
Why I like it: Real world meets imaginary world 🤝

HEART & SOIL

Format: Email
Why I like it: Great education-based email campaign for problem-aware customers. It explains the why and then offers a solution. Super basic, but quite effective.

RIDGE

Format: Email
Why I like it: Loved the subject line. Very curious.

Job Opportunities

• Credit Repair Conversion Writer (Compose.ly)

• Conversion and Growth Copywriter (CRO Metrics)

• Marketing Content Strategist (Alignerr)

• Senior Copywriter – on call (Tailored Brands)

• Content & Brand Editorial Lead (Pindrop)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 137th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: On writing guarantees

• AI Tip: Using Claude for VOC research

• 2026 State of Loyalty & Retention: 600 Shoppers Reveal What Brings Them Back (via Attentive)

• Stop Treating Every Customer Touchpoint the Same (via MarTech)

• Don’t Recommend Your Most Expensive Option (via Science Says)

• Podcast Pick: Why Routine Beats Discounts This Q4 (with Jen Gray) via Limited Supply

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Your guarantee is a risk transfer, not a nice gesture.

Most guarantees just refund the money. But that’s the weak version.

Alex Hormozi’s framing is sharper: a guarantee should reverse the risk of the outcome, not just the transaction.

“Money back if you’re not satisfied” protects against buyer’s remorse.

“We work with you until you hit X, or you get your money back” protects against the thing they were actually afraid of (that it won’t work).

Same refund.
Completely different bet.

One says “I’m confident you’ll like this,” while the other says “I’m confident this works, and I’ll prove it by staying on the hook until it does.”

When you write a guarantee, ask what your customer is actually scared of.

It’s rarely “I’ll be unhappy.” It’s usually “this won’t fix my problem, and I’ll be out the money and still stuck.”

Write the guarantee to that fear, not to the transaction.

AI Insight of the Week

Stop guessing what your customers actually say. Let Claude find it for you.

Every conversion copywriter knows the drill: mine reviews for language, find the phrases real customers use, work them into your copy.

The problem isn’t the tactic — it’s that reading 200 reviews yourself means your brain anchors on whatever you read first and skims the rest.

An LLM doesn’t have that bias. It holds the whole set in view at once and surfaces what actually repeats, not what stood out to you on review #4.

Here’s how to use it:

• Dump 100-200 reviews into Claude (a CSV works, or just paste them)

• Ask it to pull out the exact phrases customers repeat — not paraphrased, not cleaned up, verbatim.

• Ask separately for the words they use to describe the problem before they bought

• Ask it for the words they use to describe the result after.

(Those are two different vocabularies, and most copy only mines one of them.)

The words with the most conversion power aren’t the clever ones you’d write — they’re the unremarkable ones your customer already uses to describe their own life.

Voice of customer research works because it replaces your language with theirs.

An LLM is just a faster, less biased way to find it.

Must-Read Articles

Podcast/Video Pick of the Week

Why Routine Beats Discounts This Q4 (with Jen Gray) via Limited Supply

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Jen Gray’s BFCM talk reinforced how I think about subscriptions: consumers aren’t buying products, they’re buying routines, and there’s a hard line between what gets “bought” (used once, shoved under the sink) and what gets “kept” (reached for daily). Brands doing just 10% of revenue through subscriptions are seeing 7x higher LTV from those subscribers, which changes how I’d write a Black Friday subscription CTA if I were you...

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DOMINO’S

Format: Ad
Spotted By: Jamie Vaughan
Why I like it: I love a good little self-commentary in the form of parentheses.

EMIRATES

Format: Billboard
Spotted By: Callum Tyler
Why I like it: IYKYK. Not an Arsenal fan, but love the association here.

SURREAL

Format: Billboard
Why I like it: Does your product/service’s benefit break a normal naming convention? Use that to your advantage.

Job Opportunities

• Senior Growth Copywriter (Seed Health)

• 21GRAMS Copy Supervisor (Real Chemistry)

• Copy Lead of Website Content (Red Antler)

• Senior eCommerce Copywriter (Hybrid; Orca Brands)

• Direct Response Copywriter (Oktober Agency)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 136th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Guessing vs. Listening

• AI Tip: Give your claims proof

• Your Brand Now Has a Second Audience: The AI Machines (via Matchstic)

• Why Your Best Content Strategy Is Subtraction
  (via Content Marketing Institute)

• The problem with potential (via Around the Bonfire)

• Podcast Pick: 5 Pop-Up Tactics That Can Increase Your Lead Opt-in Rate
  (via Brain Driven Brands)

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Copy doesn’t fail because of bad writing.

It fails because someone GUESSED instead of LISTENED.

You don’t have to imagine what your audience thinks – they’re already telling you, in their own words, somewhere you’re probably not looking.

Start with the four-star reviews, not the five-star ones. Five stars are often too polished, sometimes fake. Four stars are where people actually explain themselves.

Then read your support tickets. That’s frustration typed in real time, before anyone’s had the chance to sound smart about it.

Pull sales call transcripts if you have them. The exact phrase someone uses right before they say yes (or don’t) tells you more than anything you could invent.

And check Reddit. People complain to strangers there the same way they’d complain to a friend.

Pull from at least three of these before you write a single line. One source is a hunch. Three? Three is a pattern.

Once you’ve drafted something, read it back and ask: does this sound like a marketer, or like someone who’s actually lived the problem?

If it’s the former, go back to the source material.

Customer language, arranged well, beats clever every time.

AI Insight of the Week

Go through your last post and circle every claim. Not just the big one in the headline. All of them, tucked into sentences you didn’t think twice about.

Now look at what’s sitting next to each one.

Most claims don’t have proof nearby. They have more claims. “This works” backed by “and it works well” is just the same sentence in a different shirt.

You don’t catch this while you’re writing because you already believe every claim you’re making. The gap between an assertion and a proven claim only shows up to someone who wasn’t convinced walking in.

Claude wasn’t.

Paste your draft in and ask it to list every claim you’re making, then ask which ones don’t have a proof element sitting nearby: a number, an example, a name, a credential, a result.

You’ll get back a short list. That list is exactly where your reader’s trust breaks.

The fix is simple. Sit a stat next to the claim it supports. Swap a general result for a specific one, and swap “clients” for a name. Proof has to sit close enough that a skimmer catches both in the same glance.

Put proof next to the claim it’s supposed to support, and the copy stops asking for trust it hasn’t earned yet.

Must-Read Articles

Podcast/Video Pick of the Week

5 Pop-Up Tactics That Can Increase Your Lead Opt-in Rate
(via Brain Driven Brands)

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Showing a pop-up twice doesn’t kill conversion rate — it nearly doubles opt-ins. The founder of Alia (recently acquired) breaks down “smart triggering”: showing a pop-up at second 5, again at product page scroll, again before exit — so the discount stays anchored in the visitor’s mind through the decision. The even better find: “mystery discount” outperforms 20% off on opt-in rate while only giving 10%, which means you’re buying the same psychology for half the margin cost.

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ALWAYS

Format: Billboard
Spotted By: Richard King
Why I like it: Copywriters just want to have fun… always.

BRUICHLADDICH

Format: Email
Why I like it: A beautifully designed email, but also a great collection launch. What’s great about it isn’t just the email, but the PDPs (17.1 example here). They do a fantastic job complementing the email campaigns, particularly in describing what makes the whisky truly unique. (Also, I really want this.)

MONDAY NIGHT BREWING

Format: Email
Why I like it: I love it when brands seize a moment. In this case, MNB (a local brewery here in Atlanta) took advantage of the questions surrounding… lettuce.. and wrote an email akin to the food safety problems and how it was of no concern to their beer, Space Lettuce. MORE OF THIS, FAM.

Job Opportunities

• Retention Strategist (Homestead Studio)

• Copywriter & Content Strategist (Homestead Studio)

• Email Marketing Account Manager (Evernue Media)

• AI-Native Conversion Copywriter – MarTech Video SaaS (Vidalytics)

• Senior Copywriter, Animal Health (FWD People)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 135th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: 4 Types of Readers

• AI Tip: Editing in Layers

• Why the Brand Experience Still Feels Fragmented (via Design week)

• The 5 “Ts” of effective email content marketing (and how to apply them) (via data axle)

• 5 AI Blindspots that Cost You Conversions (via MarTech)

• Video Pick: How To Remember Everything You Read (My Notecard System)

• Swipe File Additions

• Remote Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

“Make it punchier” is such common common feedback in copywriting.

But it’s also some of the worst.

Bryan and Jeffrey Eisenberg identified four types of readers, and most writers only know how to write for one of them.

1. Competitive readers want facts and bullets, fast

2. Spontaneous readers want a strong hook and a clear next step

3. Methodical readers want the complete picture before they move

4. Humanistic readers want a story, a person, a reason to feel something

But here’s the problem… when someone tells you to make copy “punchier,” they’re usually asking you to write for the spontaneous reader.

If your actual audience is methodical, you just alienated the person you needed most.

This is why you HAVE to decide who you’re writing to before writing a single word!

One reader. One person. One moment. One mindset.

Every choice – your hook, your pacing, your proof – it has to serve that ONE reader.

Try to serve all four modalities in every line and you’ll end up serving none of them.

So, before you open a blank doc, define your one reader and what they need from you in that moment your message is going to cross their path.

AI Insight of the Week

Editing in layers isn’t just a writing habit. It’s the difference between a good AI prompt and a lazy one.

Every editing tool works the same way: you give feedback, it makes changes, you check the result against what you meant. Claude’s no different, except most people skip that first step completely.

“Make this better” isn’t feedback.

What are you actually asking for? Clearer? More proof? More emotional pull? Better structure? You didn’t say, so Claude has to guess. Guess across six directions at once and the output lands nowhere in particular, because it was aimed at everywhere.

Compare that to giving it one job.

“Check every claim in this for proof nearby.”
“Find every sentence that could be cut in half.”
“Flag anywhere the reader has to stop and re-read.”

One lens. One pass.

You already edit this way when nobody’s watching. Clarity first. Tone next. Proof after that. Layered editing works because trying to catch everything at once means catching nothing well.

Give Claude a layer instead of a vibe.

Next time you catch yourself typing “make this better,” stop. Pick the one thing you actually want fixed. Ask for that and nothing else.

Your edits will actually sound like you. Just sharper.

Must-Read Articles

Podcast/Video Pick of the Week

RYAN HOLIDAY
How To Remember Everything You Read (My Notecard System)
📼 Watch on YouTube

Why I recommend it: Ryan Holiday’s case for physical note cards as a research and creative system — the same one behind Reagan’s speeches and Robert Greene’s 48 Laws of Power — rests on a counterintuitive premise: the friction of writing by hand, waiting before re-reading, and physically reorganizing cards is the learning. By the time an idea lands in your commonplace book, you’ve engaged with it four or five times. That is a top-tier memory system.

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SURREAL

Format: Billboard
Why I like it: Well, copywriters, It’s perfectly acceptable to make words up.

GORUCK

Format: Email
Why I like it: One of my favorite things about GORUCK over the years (beside the quality of their products), was Monster – the president of GORUCK Nation. He passed away recently and this heartfelt email to subscribers was sand on the nose. RIP, Monster.

ACTION ROCKET

Format: Email
Why I like it: In particular, I loved the CTA (”Keep your brain on”), which was directly relevant to the topic/theme of the article it referenced.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Senior Creative Strategist (ForChics)

• Senior Copywriter/Editor (Snap Finance)

• Content Manager (Terra)

• Copywriter (Sundayy)

• Conversion and Creative Strategist - US (Triquerta)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 134th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Reframing loss aversion

• AI Tip: Using Claude to reframe loss aversion

• Your Brand Narrative Is What Strangers Can Repeat (via Copywriter Collective)

• Marketers Can’t Optimize Their Way Out of a Trust Problem (via AdWeek)

• On Being an Inefficient Writer (via Psychology Meets Writing)

• Podcast Pick: The Quitting Expert (feat. Seth Godin)

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Read your own CTA out loud.

Notice everything you’re asking your reader to lose.

“Pay only $49.”
“Sign up to get started.”
“90-minute webinar.”

Small words, but each one tells the reader what they’re giving up (i.e. money, time, effort).

You don’t feel it, because you already know the trade is worth it. But your reader hasn’t made that trade yet, so the cost is still the very first thing they notice.

This is loss aversion working against you, and it can be difficult to catch in your own copy. Why? Well, you’re too close to the offer to feel what a stranger feels reading it cold.

Read your words slowly and identify every instance you’re asking your reader to give something up. Then, rewrite it.

“Pay only $49” becomes “invest $49 in clarity and confidence.”

“Sign up to get started” becomes “start your next win today.”

Same offer and price, but a completely different feeling walking in.

Your offer’s not usually the problem, but the words guarding the door to it can be.

AI Insight of the Week

Need help putting that above copy tip into action?

This is actually where AI can be useful.

Paste your copy into Claude and give it one job: find every line that frames the offer as something the reader gives up, and ask it to rewrite it as something they gain.

The trick: don’t feed it your draft. Feed it your copy you think you’re ready to publish.

Must-Read Articles

Podcast/Video Pick of the Week

DIARY OF A CEO
The Quitting Expert: Quit NOW Before AI Makes The Choice For You, This Is a Superpower! | Seth Godin

🎧 Listen on iTunes | Listen on Spotify | Watch on YouTube

Why I recommend it: You’re not stuck because you want something. You’re stuck because you want two things that can’t coexist — and you’re hiding the conflict behind the word “but.” Seth Godin’s framework: name the “but,” forgive the voice you’re not going to serve, and start throwing instead of obsessing over the catch. Because juggling isn’t about catching. If you get good at throwing, the catches take care of themselves.

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SOUTHWEST

Format: Ad
Why I like it: One of the things I love about Southwest’s branding is that they make everything feel lighthearted and human. In this case, they gave something as mundane as a catering truck and gave it a personality with nothing but five words.

ZIPPO

Format: Billboard
Spotted by: Kalpesh Bandkar
Why I like it: In the words of Kalpesh, “ You can print the lighter. You can print the logo. But why print the flame when the street already gives you one?”

HISCOX

Format: Direct Mail
Spotted by: Andrew Tindall
Why I like it: One of the most powerful things you can do as a copywriter is to remind your reader of what’s at stake – but you don’t always have to use words to do that. This direct mailer is a case in point.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Head of Brand (Surreal)

• Senior Copywriter (Phantom)

• Senior Content Marketer (Mercury)

• Copywriter – In-App & Email – DTC (TBD)

• Copywriter & Content Strategist (Homestead)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Subscribe now

Welcome to the 133rd edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: The Sequence Chain

• AI Tip: Stop Repeating Yourself

• If It Feels Interesting, It’s Material (via Psychology Meets Writing)

• AI Is Not the Skill Email Marketers Need the Most (via Holistic Marketing)

• Positioning in the Age of AI (via April Dunford)

• Podcast Pick: The Headline Formula that Works on Every Type of Customer (via Brain Driven Brands)

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Is your copy feeling… meh?

Here’s a good place to start.

Read your word creation out loud one sentence at a time. After each sentence, ask: does this give me a reason to read the next one?

The second you hit a no, stop… because that’s likely where your reader will stop too.

It doesn’t matter how sexy your next sentence is – they’re just never going to get there.

Honestly, the words were probably fine. But your order is the problem.

Here’s where chains usually break:

• A sentence answers a question before curiosity builds

• A paragraph explains something the reader already knew

• A transition does nothing but stall (”But that’s not all...”)

• A detail is true but has nothing to do with where the reader’s headed

As a marketer, I know you know this, but attention isn’t something a reader hands you all at once.

They commit one sentence at a time and you have to re-earn it every single line.

Try this on your last post or email.

Read it sentence by sentence. Mark every spot where you’d click away if you were the reader (not the writer).

That’s your sequence problem in plain sight.

Now, fix it.

AI Insight of the Week

Your best post from six months ago? It isn’t done working for you yet.

Most people think they’re running out of ideas. They’re not. They’re running out of new sentences to write, which technically isn’t the same problem.

When a post performs well, it’s rarely the phrasing that did the work. It’s the sequence. The order it moved the reader through, from the hook to the tension to the payoff.

Copy that word for word and your audience feels it, even if they can’t say why. Reuse the sequence and nobody notices, because structure is invisible.

This is where Claude earns its keep.

Paste in 3-4 of your best performing pieces. Ask it for one thing only: the structural sequence, not the sentences. What move does each paragraph make: Hook, tension, example, insight, close, whatever the shape actually is.

Then take that sequence and write a brand new post into it. New topic, new sentences, same bones.

You’re not repeating yourself.
You’re just not throwing away what already worked.

Must-Read Articles

Podcast/Video Pick of the Week

BRAIN DRIVEN BRANDS
The Headline Formula that Works on Every Type of Customer

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: A short and simple episode in which Nate Lagos shares a simple headline formula that works for nearly any brand selling almost any product to virtually every type of customer. It’s drop the formula here, but the episode’s only 12 minutes long. You have time to listen to it, bud.

Pretty Fly Copy

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

RYKER CLOTHING

Format: Ad
Why I like it: The static headline is soooo audience-specific. “If you don’t touch receipts… our shorts are for you.” IYKYK. I guess I’m one of those people, too.

SIMPLY GOOD COFFEE

Format: Ad
Why I like it: Great social proof angle – shows demand that production just can’t keep up with. The copy’s a little long, but the angle is gold.

HOLLOW

Format: Email
Why I like it: What’s your customer’s biggest pain point? With compression socks, it’s getting them on and off. This email was made for that person. Stupid simple and let’s the customer do the talking. More evidence that you don’t need to overcomplicate everything.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Content Writer (Good Content)

• Lead Copywriter (Kindred)

• Copywriter (Sundayy)

• Senior Creative Strategist (Lilo Social)

• Lead Copywriter (HOKA)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 132nd edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: The Believability Test

• AI Tip: The Awareness Audit

• [Fundamentals] How to share your point of view (even if you’re afraid of being wrong) (via Wes Kao)

• The psychology of the inbox: designing emails for tired brains (via Action Rocket)

• How Much Creative Debt are You Carrying? (via Around the Bonfire)

• Video Pick: If You Only Watch One Business Video, Make It This (via Will Barron)

• Swipe File Additions

• Job opportunities

This issue of the Weekly Round Up is once again brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That’s not an accident — it’s what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that.

Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Most copy fails the same test – the “believability test.”

What is it?

Well, read any line of the copy you just wrote and ask if your competitors could say the exact same thing about their product.

If they can, bad news. You’re not writing copy at that point, you’re just writing “category filler.”

Instead of the basics like “save time” or “grow your business” or “feel better,” try to be more specific:

• Save 17 minutes every morning

• Add $4,200/mo. in recurring revenue

• Wake up without the 3pm crash

That specificity communicates the same idea, but with a completely different effect.

Why does this work?

Well, our brains treat specificity as PROOF. Vague claims sound like marketing and your guard’s immediately going up. Specificity, however, sounds like fact.

And your proof doesn’t actually have to be dramatic (although it should at least be true). But that precision is what sells.

So, take something you’ve written (it could already be up on your website or in an email), and ask yourself: Could a competitor steal this word for word?

If the answer’s yes, then sit down and fix it with a number, a name, or a detail only YOU could claim.

(Or don’t. Your call.)

AI Insight of the Week

You know your product too well to write to someone who doesn’t.

You’ve spent months inside your product.
You know the mechanism and you know why it works, but your reader doesn’t.

They’re still stuck on the problem and you’re three steps past it.

You write to the person you’ve become instead of the person reading you.
The sentences are fine, but it’s the gap that’s the issue.

This is one of the rare places AI can beat you at your own job. You’re too close to your product to see where you skipped ahead. Thankfully(?), Claude isn’t.

Try this:

Paste your draft into Claude.
Tell it exactly where your reader is right now. Problem-aware. Solution-aware. Somewhere in between.

Then give it one instruction: “Flag every line that assumes more awareness than this reader has.”

Not “make this better.”
Not “give me feedback.”

One lens, one pass.

You’ll get back the exact lines where you talked past your reader instead of meeting them.

Fix those and the post you already wrote starts landing the way you meant it to.

Must-Read Articles

Podcast/Video Pick of the Week

WILL BARRON
If You Only Watch One Business Video, Make It This

🎧 Watch on YouTube

Why I recommend it: Most service business owners lose deals not because their service isn’t good enough, but because they pitch before they diagnose. Will Barron’s five-step framework covers the whole process — from mapping the “reality gap” (current pain to desired outcome) on discovery calls, to the two-sentence micro close that forces a yes or no without sounding like a sleazy salesperson. Useful for anyone who sells anything, even if your “product” is your own creative work.

Pretty Fly Copy

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Bedford Whaling Museum

Format: Ad
Spotted By: Jason Feifer
Why I like it: I’ve seen this type of campaign angle take off before (using 1-star reviews), but not at this level. Mad props to the team at BWM for owning who they are!

LIDL

Format: Ad?
Spotted By: Amy Hawthorne
Why I like it: While this wasn’t a true Lidl ad, it was an amazing spec piece from Amy Hawthorne. I hope Lidl picked it up (love that grocery chain, btw).

Jo Atkins-Potts

Format: Poem
Spotted By: Chance Marshall
Why I like it: Sometimes inspirational copy isn’t an ad or a landing page or a video or an email – sometimes it goes back to the basics: poetry. Loved this reflection that Chance Marshall shared from Jo Atkins-Potts.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Senior Copywriter (Southend Pharmacy)

• Senior Copywriter (Mindbody)

• Senior Copywriter (Hook)

• Senior Copywriter (Seed Health)

• Creative Copy Strategist (Shift Paradigm)

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Let’s talk about evergreen content.

Ask five people what “evergreen content” means and you’ll get five versions of the same fuzzy answer. Something timeless. Something that doesn’t go stale. A how-to instead of a hot take.

That’s true enough. It’s just too thin to act on.

Evergreen isn’t a content type. It’s not a writing style either, no matter how many style guides talk about it like one. It’s a decision about durability, made once when something gets published and made again every time you choose whether to keep it standing.

A piece is evergreen because somebody keeps maintaining it, not because it was written in timeless sounding language.

Write the most timeless sentence in the world about a product that gets discontinued next spring, and you’ve written something that will be wrong in eight months, no matter how good the sentence was.

What you’re actually agreeing to, when someone says “let’s build something evergreen,” is a maintenance commitment. Most teams quietly drop that commitment the moment the piece goes live.

This issue of The Edit is brought to you by Shlomo Genchin:
CopyTemplates

My friend Shlomo just launched CopyTemplates ($97) – a library of 63 proven copywriting techniques, each comes with handpicked examples (500+ in total), plus 70+ copy-paste AI prompts and Claude skills.

It’s the best resource I’ve seen for writing headlines, with or without AI.

Get it for $97 for a limited time

Building is the obvious move. Maintaining is the one people skip.

There are two different jobs hiding inside “let’s use this slow stretch for evergreen content,” and they deserve to be named separately, because most people only do one of them.

The first is building new. This is the deep guide you’ve been meaning to write since February. The resource page that would save your team the same explanation for the fortieth time. The framework piece that’s been a half finished doc for three months because nobody could carve out the four hours it actually needs. The slow season hands you those four hours. Use them.

The second is maintaining what’s already there, and this is the one that gets skipped almost every time.

Go pull up something you published a year or two ago. Look closely. The example you used is probably out of date. The screenshot shows a version of a product that’s been redesigned twice since. The tone might not even sound like you anymore, because you’ve changed and the page hasn’t.

That piece is still live and maybe it’s still ranking. It’s still the first thing a new reader finds when they search your name next to the topic. And yet it’s passively representing a version of your thinking you’d correct yourself on if anyone asked you directly.

Most content strategies treat evergreen as something you make once and check off. But the actual job is something you keep doing, and a slow season, summer for a lot of people, is exactly when you have the room to do it without it competing with everything else on your plate.

If you lead a team, this is worth saying out loud to them, because nobody puts “go fix a two year old blog post” on a list of impressive downtime projects. It feels small, but it isn’t. It’s the unglamorous half of the same investment as building something new.

Deadlines optimize for today. Downtime optimizes for the next two years.

This is the actual mechanism behind all of this, and it’s simpler than it sounds.

When you’re working under pressure, you optimize for whatever’s due. A launch needs copy by Thursday, so you write copy that’s good enough to ship by Thursday. That’s not a knock on the work. It’s just what pressure does. It narrows your view down to the thing in front of you, and the thing in front of you is rarely “will this still hold up in two years.”

When the pressure lifts, the aperture opens back up. You’re no longer asking “is this good enough for Thursday.” You’re free to ask “is this good enough to still be true next spring,” which is a completely different question with a completely different answer.

Same person.
Same skill.

Different question, because the only thing that changed is whether something was bearing down on you while you answered it.

This works exactly the same way whether you’re allocating a team’s hours or your own.

If you run a department, the version of this is choosing, on purpose, to point a few people at long horizon work instead of letting the calendar default to whatever’s loudest.

If you’re a freelancer or a solo operator, it’s the same decision made with your own time, which arguably takes more discipline, since there’s no one else’s calendar making the call for you.

Either way, the slow season isn’t a break from the real work. It’s the only window where the durable kind of work actually gets a fair shot.

Most of what you could build doesn’t deserve the investment.

None of this is permission to spend the summer building everything you’ve ever thought of. Not everything earns evergreen treatment, and pretending otherwise just produces a different kind of clutter.

Here’s the filtering question: would this still be true and useful in two years if nobody touched it again?

If the honest answer is yes, then great! You’ve found something worth either building from scratch or adding to the maintenance list. It’s durable enough to be worth the upkeep.

If the answer is no, well, that’s fine too. It just means the idea was never evergreen. It was a good piece for right now, and right now is a perfectly respectable thing for content to be. Honestly, not everything needs to last. Plenty of useful work has a shelf life of a season, does its job in that time, and that’s enough.

The mistake isn’t writing things that expire. The mistake is mislabeling them, calling something evergreen out of habit and then being surprised two years later when it’s wrong.

AI can spot what’s gone stale. It can’t decide if anyone still needs it.

This is one of the places AI is genuinely useful.

Point it at your existing library and ask it to flag what’s likely outdated: references to discontinued products, links that no longer resolve, examples leaning on numbers from two years ago.

Ask it to draft a first pass at an outdated section, or spin a long guide into a shorter version for a different platform, or tighten the SEO on something that’s been underperforming for reasons nobody’s diagnosed.

All of that is real time saved, and during a slow season it means the maintenance half of this work stops competing for hours with the building half.

What AI can’t do is tell you whether the piece still matters. It doesn’t know if your audience moved on, if your positioning shifted, or if the topic itself just isn’t the one you want to be known for anymore. AI can tell you what’s stale, but only you can tell whether it’s still worth keeping fresh. Treat it as the thing that hands you a shorter list to think about, not the thing that thinks about it for you.

The pressure is coming back. The question is what it’ll find.

The slow seasons won’t last. They never do. Your busy season will show up the way it always does, with a calendar that fills back in faster than anyone expects, and the version of you that exists then is going to be very busy optimizing for whatever’s due that week.

That version of you is going to need something to stand on. Whatever you build or fix now is what they’ll be standing on later.

When the pressure comes back, what will you wish you’d built while it was slow?

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Welcome to the 131st edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: The 3 C’s of Story

• AI Tip: Save the horsepower for where it actually moves the needle.

• The Revision Where Good Work Goes to Die (via Copywriter Collective)

• Why the Rule of 3 Makes You a Better Communicator (via INC)

• Marketing needs AI outcomes, not more AI pilots (via MarTech)

• Principles Over Pressure: Sticking To Your Values During Mid-Year Sales Pushes (via The Copy Minimalist)

• Podcast Pick: Choose the Right Channel: How Stanford Finds Its Voice

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is brought to you by Shlomo Genchin:
CopyTemplate

s

My friend Shlomo just launched CopyTemplates ($97) – a library of 63 proven copywriting techniques, each comes with handpicked examples (500+ in total), plus 70+ copy-paste AI prompts and Claude skills.

It’s the best resource I’ve seen for writing headlines, with or without AI.

Get it for $97 for a limited time

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Every story that sells has the same skeleton:

1. Character

2. Conflict

3. Change

Strip away the branding, the product, the channel — every story that actually moves someone has all three. Remove any one, and the whole thing collapses.

Character: someone the reader recognizes. Could be a customer, a founder, a version of themselves.

Conflict: the thing standing in their way. Without tension, there’s no reason to keep reading.

Change: what’s different now. No change, no point.

Most “brand stories” only have one or two of these. They introduce a character, skip the real conflict, and jump straight to “and now we’re great.”

But that’s not a story. There’s no depth.

If you want your story to actually sell, give the reader all three – especially the conflict! It’s the part everyone’s most tempted to cut, but it’s almost always the part doing the most work.

AI Insight of the Week

Use your most powerful model for the first draft. Switch to a simpler one for iteration.

Most people pick a model and stay on it for the whole task, but that’s backwards.

The first draft is where the real thinking happens — structure, angle, the core argument. That’s the part you want your strongest model on. Get the hardest cognitive work done up front, when the stakes for quality are highest.

But once the draft exists, the work changes. You’re tightening lines, adjusting tone, trying variations. That’s lighter lifting, and a faster, cheaper model handles it just as well (and often faster, which matters when you’re iterating quickly).

So my advice? Front-load the intelligence. Save the horsepower for where it actually moves the needle.

Must-Read Articles

You Should Read This Too:

THINK FAST TALK SMART
Ep. 299: Choose the Right Channel: How Stanford Finds Its Voice

🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Stanford’s VP of communications runs every story through one question before a single word gets written: short video, longform, or media pitch — and sometimes the answer is “let a journalist tell it, not us.” Farnaz Khadem breaks communication down to three things: know your goal, know your audience, know your data, plus a crisis-comms rule worth stealing. Anybody who communicates should listen to this!

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

HOWLER BROTHERS

Format: Email
Why I like it: If there’s a killer/fun story behind your product – share it! I actually own this shirt and I didn’t know the legend behind it. Honestly, pretty damned cool.

SEED

Format: Email
Why I like it: The subject line leaves me wanting, but the guts of the email (pun intended?) are fantastic for someone who’s product aware and looking for a reason to switch. It pulls all the social proof levers.

BITE

Format: Email
Why I like it: A great example of the PAS copy framework at play. And honestly, more CPG/wellness/supplement brands should do this.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Director, Copy and Content (Agency)
  Remote

• Creative Lead, Marketing (Agency)
  Remote

• Senior Copywriter (Agency)
  Remote

• Marketing Content Writer (B2C)
  Remote

• Senior Copywriter (Tilt)
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

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Welcome to the 130th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: An email is not a landing page. ****

• AI Tip: Revisit your Project system prompt quarterly.

• The human-centered approach to AI adoption (via ActionRocket)

• Marketing measurement is breaking under its own complexity (via MarTech)

• The Psychology Behind Headlines That Make Customers Click: Understanding the Science of Attention (via The Copy Minimalist)

• Podcast Pick: The Anatomy of a High-Converting Listicle

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is once again brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

An email is not a landing page.

They’re not the same job, they don’t follow the same rules, and when you write them like they are, both suffer.

A landing page has one job: close. It gets a focused, distraction-free environment and has room to handle objections, build proof, and walk someone all the way to a decision.

An email has a different job: earn the click.

That’s it.

Get them curious enough, interested enough, or compelled enough to want more — then get out of the way.

When you try to do the landing page’s job inside the email, you end up with something too long to read and not focused enough to convert. You’ve explained everything, so now there’s no reason to click. And you’ve buried the CTA somewhere after three scrolls.

Write the email to earn the click. Let the landing page do the closing.

Two jobs. Two pieces of copy.

Don’t make one do both.

AI Insight of the Week

Revisit your Project system prompt quarterly. Your standards evolve, so your Project should too.

Most people set up a Project system prompt once and never touch it again.

But your taste has sharpened, your audience understanding has deepened, and you’ve learned what Claude does well in this context and where it keeps missing.

None of that is reflected in a system prompt you wrote on day one.

A quarterly revisit doesn’t have to be a rebuild. Usually it’s smaller than that — tightening a constraint that’s been producing mediocre outputs, adding an example of a recent piece you’re proud of, or removing a rule that made sense then but doesn’t now.

Think of it like a performance review. Not for Claude, but for the brief you gave it.

Must-Read Articles

The human-centred approach to AI adoption (via Action Rocket)

Why I recommend it: ActionRocket didn’t start their AI rollout by asking “where can we use AI?” — they started by asking “what slows people down?” The result: automations nobody misses, copywriters who own more of the work that matters, and the irony that adding technology made the agency more human, not less.

Marketing measurement is breaking under its own complexity (via MarTech)

Why I recommend it: The average marketing team uses six different tools to measure performance — and only 18% say they can clearly see what’s working. More data didn’t solve the problem, it deepened it: every channel tells a different story, and the tools built to connect them are the least commonly used ones in the stack.

The Psychology Behind Headlines That Make Customers Click: Understanding the Science of Attention (via The Copy Minimalist)

Why I recommend it: Your brain makes engagement decisions in 50 milliseconds — long before rational thought kicks in. This deep dive covers the five psychological triggers behind every headline worth clicking: novelty, loss aversion, curiosity gaps, pattern disruption, and emotional priming. Plus a practical framework for knowing which trigger to pull based on where your customer is in their journey.

You Should Read This Too:

LIMITED SUPPLY
The Anatomy of a High-Converting Listicle
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: A “10 reasons why” listicle converts at 6-7% versus 1-1.5% on a standard product page, because it qualifies traffic without directly selling. Nick Sharma walks through real listicle teardowns — the two-layer-deep angle trick (”for people who drink regularly,” not just “for everyone”), why mobile-first wireframing beats designing for desktop, and where AI actually helps versus where it just produces slop.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

MATT FROEHLICH

Format: LinkedIn
Why I like it: My former coworker is a BIG sports guy (and a wildly talented growth strategist for DTC brands). Thought this was a creative way to announce his impending availability in the job market. (And if you’re hiring, he’s a catch).

HUCKBERRY

Format: Email
Why I like it: If you’re looking for a way to increase AOV (average order volume), featuring products that go well together in an email are a great way to do that. Huckberry’s also done “capsule” emails in the past, which is fantastic for apparel brands.

PAYA

Format: Email
Why I like it: Great example of a problem/agitation/solution at play for a skincare brand.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Content Lead (Bobbie)
  Remote

• Creative Content Lead (CPG Brand)
  Remote

• Email Copywriter (Agency)
  Remote

• Copywriter (Astrally)
  Remote

• Senior Content Writer (Compound Content Studio)
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

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There’s a particular kind of pressure that shows up around the middle of June, and if you’ve worked in this field long enough, you can feel it coming before anyone puts it into words.

The first half of the year is closing out. Someone has done the math on where the numbers actually landed versus where they were supposed to, and the gap is bigger than anyone wants it to be.

So the meetings get rescheduled a little earlier, the messages get a little shorter, and eventually it arrives in one form or another: we need to push harder this month.

If you work in-house, it usually sounds reasonable. Leadership wants the messaging punched up, the calls-to-action sharpened, the offers pushed a bit more aggressively.

If you freelance, it tends to come from a client who’s suddenly asking for the countdown timer, or the “only a few spots left” line, or the urgency you both know isn’t quite real.

And here’s what makes this moment genuinely hard to navigate, rather than just unpleasant. Nobody’s asking you to lie. That would be easy. A clear request to deceive someone is something most of us would recognize and refuse. What you actually get is something much softer and much harder to push back on.

You get asked to be more aggressive, more urgent, more compelling. And every individual request, looked at on its own, sounds completely fair.

You’re never handed one big decision you can plant your feet against. You’re handed a dozen small ones, each of them reasonable, and somewhere in the middle of saying yes to all of them you’ve ended up somewhere you wouldn’t have chosen on purpose.

Let me give you a version of this I’ve seen play out more than once, because it makes the whole thing concrete.

Picture a brand with a single evergreen offer, the same deal running quietly in the background all year long. Mid-June rolls around, the numbers are soft, and someone has what feels like a perfectly good idea: take that evergreen offer and dress it up as a Father’s Day sale.

So the emails go out. Final hours. Last chance to get twenty percent off for Dad. The countdown timer ticks down toward zero, and everyone watches the orders come in.

Then the next morning arrives, the “sale” ends, and the evergreen offer simply resets. Same price. Same terms. There was never anything to miss in the first place.

I want to be fair about this, because nobody in that room thought of themselves as dishonest. They had a real offer and a real date on the calendar, and stitching the two together felt less like deception and more like resourcefulness.

But that’s exactly why this is worth talking about. The problem here isn’t villains. There usually aren’t any. The problem is what happens to good people and good brands when the pressure shows up and starts quietly bending things, one reasonable inch at a time.

Pressure doesn’t test your marketing. It tests whether your principles were ever real.

My hot take: values are free in January.

Every brand has them. They’re in a deck somewhere, a Notion doc, a tidy little list on the About page. “We believe in honesty.” “We’re a premium brand.” “We serve this customer better than anyone.” Easy to write. Costs nothing to say.

But June is when those values get a price tag.

There’s a difference between a value you state and a value you hold, and the only way to ever know which one you’ve got is to wait until it costs you something.

Revenue.
A client.
An easy win you have to walk away from.

Until the bill comes, you genuinely don’t know. You’re just guessing about your own character. And most people guess generously.

Now, when we talk about “principles” in marketing, everybody jumps straight to honesty. Don’t deceive people. Fair enough. The fake Father’s Day sale is the obvious version.

But honesty isn’t the only thing pressure comes for. There are two others that get abandoned just as often, and a lot more quietly.

The first is positioning.

Say you’ve decided to be the premium option in your market. Good. That’s a real decision with real teeth. Then Q1 comes in soft, and there’s a discount sitting right there on the table, the easiest yes you’ll find all month.

But a discount doesn’t just move units. It tells your market something. It says you were never really the premium thing. You were the regular thing, waiting for a reason to go on sale. And once you’ve taught people to wait for that reason, they will. Forever. You don’t get to charge a premium and run a sale rack at the same time. One of them wins, and if you won’t choose, the pressure chooses for you.

The second is conviction.

Maybe back in January you decided to go hard on one kind of customer. One segment, one category, one group you were going to serve better than anyone else in the space. Smart. Focused. The kind of bet that pays off over years.

Then June hits and it’s harder than you thought. You’re hitting walls. The numbers are slower than the easy stuff would’ve been. And the tempting move is to quietly widen the net. Stop being the brand for them and start being the brand for whoever’s buying that week.

The principled move is to assume the hard part is the work. Not a sign you bet wrong.

So here’s the thread tying all three together.

A principle isn’t just “don’t lie.”
A principle is any decision you made in a calm moment that the market will later pay you to unmake.

Pressure is the invoice.

Which means the pressure isn’t the enemy here. It’s the test. It’s the only honest test you get all year of whether those January values were ever load-bearing or just decoration.

This is the whole premise of principle-based marketing: the values only matter at the moment they cost you something.

How the drift actually happens

But here’s the thing: nobody decides to become a manipulative brand. What they decide is much smaller.

They decide one deadline can be “basically real.” They round one number up because it’s close enough. They let one testimonial stand because it’s “essentially what the customer meant.” Each move is defensible if you hold it up by itself. Anyone would sign off on it.

But it’s the sum that’s the problem! And unfortunately, nobody ever looks at the sum.

Go back to that Father’s Day sale for a second.

No one in that room set out to trick anybody. They had a genuine offer. They had a real holiday on the calendar. Wrapping one in the other felt like resourcefulness, not deception. Yet that’s exactly how the line gets crossed! Not by somebody deciding to cross it. By nobody noticing it was there.

Pay attention to the language, too, because the compromises always show up wearing respectable clothes.

You don’t tell yourself you’re faking urgency. You’re “creating urgency.” You’re not caving on price. You’re “testing a stronger offer.” You’re not abandoning your customer. You’re “expanding the audience.” The words are doing a job, and the job is to let you feel fine about it.

Here’s the part I really want you to pay attention to…

Your customers notice.

Maybe not consciously. If you stopped one and asked, they probably couldn’t point to the exact email that did it.

But the sale that wasn’t really a sale registers somewhere. It gets quietly debited from an account you can’t see on any dashboard, the one labeled do I actually believe these people.

And you never get an alert when that balance drops. You just find that your next campaign works a little less well than it should, and your one after that, and you sit there blaming the subject line. You tune the copy. You swap the image. You never once suspect the real problem, which is that you spent down your credibility for a 20% bump in June and the interest is coming due all year.

People aren’t dumb.
They clock the move.

The only question is whether you’ve decided to make them pay for noticing. (This is the same buyer instinct I wrote about in “the one thing AI can’t learn”: conversion runs on a felt sense of trust, and customers register when it’s missing long before they could explain why.)

Decide before the pressure does

So what do you actually do about it?

Not a framework. I’m not going to hand you a five-step system, because a system is just one more thing to abandon when things get hot.

Here’s the real move, and it’s almost annoyingly simple.

You decide before the pressure arrives.

Principles only survive a crunch when you’ve already turned them into decisions. Calls you made when you were calm, that you then flat-out refuse to reopen when you’re not. The whole trick is taking the decision out of the hot moment, because the hot moment is exactly when you make your worst calls.

A few of mine look like this:

• Deadlines are real or they don’t exist. No resetting timers.

• We only claim what we can actually show.

• We don’t discount our way out of a slow quarter.

• The customer we committed to in January is still the customer in June. Especially when it’s hard.

Notice those aren’t clever. They’re not supposed to be. They’re supposed to be boring and settled, so that when somebody floats the fake countdown idea at 4pm on a Friday, the answer’s already sitting there.

You don’t have to relitigate your ethics on the spot. You just point at the thing you decided months ago, back when you could think straight.

If you lead a team, this matters even more, and it’s mostly on you. These decisions have to be said out loud, to your people, before the push. Because if you haven’t, you’ve left some junior writer alone in a doc at the end of a long week trying to figure out whether “hit the number” quietly cancels out “hold the line.”

That’s not a fair thing to make them guess. Decide it for them, ahead of time, so they never have to negotiate it solo.

And if you’re a team of one, write them down anyway and stick them somewhere you’ll see them. Because the conversation with a pushy client goes completely different when you walk in having already decided where you stand. You’re not deciding under fire. You’re just reporting a decision you already made.

Under pressure, you don’t rise to your values. You fall to your defaults.

So the only thing that actually matters is what you built your defaults to be, and you build those on a quiet Tuesday in March, not in the middle of a June scramble.

Holding the line isn’t refusing to sell

Now, I know how some of this can read. Like I’m telling you to go soft, and sit on your hands and run gentle little campaigns and leave money on the table to keep your conscience clean.

No, I’m not. That’s not it at all.

Urgency is great when the deadline is real.
Scarcity works when the stock is actually low.

Strong offers, direct asks, hard closes, the occasional genuinely-ends-Friday sale, all of it is fair game when it’s true. A premium brand can have an absolute monster of a quarter. It just does it by selling the premium harder, not by becoming the clearance brand for 30 days and hoping nobody remembers in July.

The pressure to sell was never the problem. The shortcut is.

And here’s the thing about the shortcuts – they feel like effort, but they’re the opposite. The fake deadline, the panic discount, the suddenly-much-bigger audience, those are all things you reach for instead of solving the actual problem. They’re the easy door.

The principled move and the genuinely creative move turn out to be the same move almost every time, which is to push through the hard thing rather than sneak around it.

The bonus, and it’s a real one, is that the honest version usually just works better.

True urgency beats fake urgency, because when you say “Friday” and mean it, people learn that your next “Friday” is worth acting on.

Held positioning beats a discount habit, because you keep both your margin and your meaning. And conviction beats chasing, because you end up genuinely great at one thing instead of forgettable at five.

Doing it right isn’t the noble, costly option. Most of the time it’s just the option that’s still working a year from now.

What mid-year pressure actually reveals

The push isn’t going anywhere. It shouldn’t. Mid-year pressure is a normal part of doing this work, and honestly, some of it is good for you. It sharpens things.

It’s just that it also tells you the truth.

Every June, the pressure walks in and quietly itemizes everything you said you believed back in January, and puts a price next to each one.

The fake sale you didn’t run.
The discount you didn’t reach for.
The customer you didn’t abandon when it got hard.

That bill is the most honest feedback you’ll get all year.

So I’ll leave you with the question I keep coming back to.

Which of your principles has actually cost you something this year?

Because if the answer is none of them, that’s worth sitting with. It doesn’t mean you’re disciplined. It might just mean nobody’s pushed you yet.

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Welcome to the 129th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Your word choices don’t just say things. They reveal things.

• AI Tip: Projects vs. Skills (when to use both)

• Disagreeing with Rick Rubin (via Around the Bonfire)

• Why Great Creatives Keep Delivering Average Work (via Copywriter Collective)

• Employee Ownership is Not a Culture Strategy (via Branding Strategy Insider)

• Podcast Pick: 17 Things Brands Get Dead Wrong About Millennials

• Swipe File Additions

• Job Opportunities

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get the first principle for FREE here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Your word choices don’t just say things. They reveal things.

Every word you pick signals how you see the person reading it.

Write “simple” instead of “easy” and you’re implying they need things dumbed down. Write “just click here” and you’re signaling that their hesitation is an inconvenience. Write “as you probably already know” and you’re either being condescending or covering your own bases.

Readers feel this. They may not be able to name it — but they respond to it.

The best copy treats the reader like a smart person who has a real problem and deserves a straight answer. Every word either reinforces that or undermines it.

So next time you’re editing, don’t just ask is this clear?

Ask: what does this word say about how I see the person reading it?

AI Insight of the Week

A Project sets the world. A skill teaches the job. You need both.

Most people build one or the other and wonder why their outputs are inconsistent.

A Project system prompt answers the contextual questions (e.g., who Claude is, who the audience is, what good output looks like, etc.). It’s the operating environment.

A skill file answers the procedural questions (e.g., the framework, the process, the steps for executing a specific task well, etc.). It’s the methodology.

They’re not redundant.
They’re layered.

The Project without the skill gives you the right voice but no repeatable process. The skill without the Project gives you a solid process but no context.

Build both.

That’s when Claude stops feeling like a tool and starts feeling like a specialist.

Must-Read Articles

Disagreeing with Rick Rubin (via Around the Bonfire)

Why I recommend it: Rick Rubin says the audience comes last. Marketers say the audience comes first. Kevan Lee and Shannon Deep say both are right — because “audience” isn’t one thing. There’s the imagined audience (the committee in your head), the real audience (people with actual problems), and the future audience (the people who’ll recognize the work once it exists). Most watered-down creative work comes from obeying the first one.

Why Great Creatives Keep Delivering Average Work (via Jake Stafford, Copywriter Collective)

Why I recommend it: After decades placing creative talent, the pattern is clear: when brilliant writers deliver average work, the brief is almost always the culprit. A vague brief, a review-by-committee, and a culture of playing it safe will produce exactly what you’d expect — because great creatives don’t bring their best to rooms where bold ideas keep getting sanded down in approval.

Employee Ownership is Not a Culture Strategy (via Branding Strategy Insider)

Why I recommend it: “We are employee-owned” is a structure, not a culture strategy — giving everyone a key to the building doesn’t tell them what kind of business to build inside it. A useful reframe for anyone leading a team: ownership creates pride, but pride without direction doesn’t create customer trust. Culture does.

You Should Read This Too:

BRAIN DRIVEN BRANDS
17 Things Brands Get Dead Wrong About Millennials
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: Millennials aren’t 25, aren’t in their prime spending years, and own 3% of the wealth boomers had at the same age — so stop marketing to them like they are. Sarah and Nate break down 17 things marketers get wrong, from the BS detector built by a lifetime of ads to why “this salad is the sigh of relief you needed today” is the fastest way to lose us forever.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

PADDY POWER

Format: Billboard
Spotted By: Paul Smith
Why I like it: A marketing “gamble” for a gambling platform. Nice.

HOLLOW

Format: Email
Why I like it: Great Fathers Day themed email (and I love a good theme). I am a grill master. Definitely need to get myself a pair.

PATH PROJECTS

Format: Email
Why I like it: These guys don’t just make running shorts, they’e essentially solved a problem for the most serious distance runners – a solve that sets them apart. And the headline sums it up perfectly.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Associate Creative Director, Copy (YouTube/Social)
  Remote

• Marketing Data Analyst
  Remote

• Email Copywriter (Agency)
  Remote

• Content Lead
  Remote

• Senior Copywriter
  Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

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Welcome to the 128th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: When editing REALLY starts.

• AI Tip: End every strategic session by asking Claude to summarize the decisions made.

• The Psychology Behind Inbox Placement (via InboxAlly)

• I’ve Written 47 CTAs. Only One Worked (via Copywriter Collective)

• “Better Copy” Kills Positioning (via Kate Guerrero)

• What the Best Copywriters Will Have in Common 10 Years From Now (via The Copy Minimalist)

• Podcast Pick: The Hook Secrets That Make You Keep Watching

• Swipe File Additions

This issue of the Weekly Round Up is brought to you by:
The Conversion Copy Operating System

The rules of copywriting contradict each other. That's not an accident — it's what happens when you learn tactics without the principles that govern them. The Conversion Copy Operating System fixes that. Get early access here→

👋 Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Most copywriters edit the same way they were taught to write.

Start at the top.
Work down.
Clean up what you find.

But that’s not editing, that’s proofreading.

Real editing starts BEFORE you touch a single word.

Before I read a draft, I orient myself.

I know the audience.
I know where they are in terms of awareness.
I know how sophisticated this market is.

I go in with a frame, like Schwartz said, and I have an idea of what I’m about to read. It’s that frame that allows me to see structural problems that have nothing to do with word choice.

A line can be grammatically clean and still be wrong.

Wrong for where this reader is.
Wrong for what they believe right now.
Wrong for the sequence of the argument.

That’s what I’m looking for on pass one: whether the argument is landing in the right order for the right person.

If it isn’t, nothing else really matters.

You can’t edit your way out of a broken structure. You can tighten every sentence and still end up with copy that doesn’t convert, because the problem was never the words in the first place. It was the sequence.

Remember this: structure first.
Always.

If you’re spending your first pass fixing commas, you’re editing the wrong thing.

AI Insight of the Week

End every strategic session by asking Claude to summarize the decisions made.

Not a recap of the conversation – the decisions.

There’s a difference. A conversation summary tells you what was discussed. A decisions summary tells you what you actually committed to, and that’s where the surprises live.

Most strategic sessions with Claude produce more conclusions than you realize. You agreed on an angle. You ruled out an approach. You made an assumption about the audience and kept moving. None of it felt like a decision in the moment, but it was.

Ask Claude: “What decisions did we make in this conversation?” and read it carefully. You’ll almost always find at least one assumption you didn’t know you’d made.

Must-Read Articles

The Psychology Behind Inbox Placement (via InboxAlly)

Why I recommend it: Inbox placement isn’t just a technical outcome, it’s a behavioral one. Mailbox providers aren’t checking your DNS records, they’re watching what your subscribers do in the first fraction of a second. Kath Pay applies Kahneman’s System 1/System 2 framework to deliverability and makes the case that you’re not just optimizing emails, you’re conditioning expectations.

I’ve Written 47 CTAs. Only One Worked (via Copywriter Collective)

Why I recommend it: After 47 versions of a two-word button, the winner was “See the prices.” Not punchy. Not branded. Not elevated. Just a doorway that told the reader exactly what was on the other side, and doubled the click-through rate against “Discover the Collection.” The whole piece is a reminder that a CTA isn’t a headline. It’s a promise.

“Better Copy” Kills Positioning (via Kate Guerrero)

Why I recommend it: Positioning sessions feel great until the copy ships — and suddenly the founder wants to say something completely different. Kate Guerrero nails why: strategy is theoretical, copy is public. A great copywriter’s job isn’t just to write well. It’s to hold the line when fear shows up dressed as a feedback note.

You Should Read This Too:

JOANNA WIEBE
The Hook Secrets that Make You Keep Watching

🎧 Watch on YouTube

Why I recommend it: Eight strategies for hooks built on a century of direct response thinking and updated for the 30-second scroll. The most useful framework: every piece of content needs a super hook (the big open question held until the end), nested hooks underneath it, and mini hooks every 12–15 seconds. If the tension closes too early, the brain moves on…

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

PITVIPER

Format: Email
Spotted By: Jessica L.
Why I like it: 100% the last thing I’d expect to see from a brand in my inbox. Absolutely love the quirkiness and personality this type of campaign demonstrates.

CHEWY

Format: Email
Why I like it: I thought this was great for a solution aware/most aware audience (me!). It includes all the right persuasion levers for me (outside of a discount), and a hilarious product pic to boot.

PAKT

Format: Email
Why I like it: There’s a trend I’ve been noticing lately with a lot of DTC brands: intentional storytelling via email. It’s a welcomed shift, imo. But I like how this begins by placing a demand on your imagination as a way to prime you for positioning their product as a value-add to said imagined situation. So good!

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Creative Lead, Performance Copy
  Kin Insurance | Remote

• Sr. Lead Product Copywriter
  Hims | Remote

• Copywriter and Creative Strategist
  Super Speciosa | Remote

• Snr. Content Copywriter
  myTomorrows | Remote

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

Everyone has an opinion on what copywriters need to learn right now (heck, even I do).

More hooks. Better prompts. Shorter sentences. Longer emails. Be on LinkedIn. Don’t be on LinkedIn. Be on Substack. Don’t be on Substack.

The advice isn’t exactly wrong, but it’s mostly aimed at the surface, and the gap opening up in this field isn’t a surface problem.

The writers pulling ahead aren’t the ones who found a better hook formula. They’re the ones who got sharper about how they think about the work before they write a single word.

And most conversations about “leveling up” are completely missing it.

Why Craft Alone No Longer Separates Strong Copywriters From Average Ones

For a long time, the path forward was clear.

Study the greats.
Learn the fundamentals.
Write more.
Get better feedback.
Repeat.

That path still works. Craft is not dead. Writers who can’t construct a sentence that moves someone aren’t going to be saved by strategic thinking alone.

But here’s what I’ve noticed after so many years in this field: craft rarely explains the gap between writers who consistently produce work that performs and writers who don’t.

The difference almost always lives upstream of the draft. It’s how they approach the problem before they even open a blank document.

The writers who plateau are usually technically capable. They can write a clean sentence, follow a brief, and hit deadlines. But ask them why a piece isn’t working, and they’ll look at the words. Rarely the thinking behind the words.

That’s the ceiling most writers bump into.
And more writing reps won’t raise it.

What Strategic Thinking in Copywriting Actually Means

Strategic thinking about copy means being able to answer four questions before you write anything.

What is this supposed to do?
For whom?
At what point in their decision-making?
What does this person already believe, and what do you need them to believe differently by the end?

Most writers can execute a brief, but fewer can interrogate one.

There’s a real difference between a writer who gets an assignment and starts writing, and a writer who gets an assignment and starts asking questions. Not to be difficult, but to be useful. Because a brief that doesn’t answer those questions is a brief that will produce mediocre work no matter how good the execution is.

This isn’t a complicated idea, but it does require a shift in how you see your job.

Your job isn’t to fill space with words that sound like marketing. Your job is to move a specific person from one mental state to another. The writing is how you do it. The thinking is why it works.

And when you begin to internalize that, everything changes. You stop asking “how should I write this?” and you start asking “what does this person need to feel, see, or believe for this to work?”

Interested in sponsoring an issue of The Edit? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

How to Develop an Editorial Eye: Diagnosing Copy Problems Clearly

The second skill most writers have never been taught: how to critique copy clearly.

Editorial skill in copywriting is the ability to name why a piece isn’t working, not just sense that it isn’t. A lot of it’s because they’ve been taught to write, not to evaluate.

There’s a difference between sensing that something doesn’t work and being able to name why. “This feels off” is not a usable note. “The reader doesn’t feel recognized in the first two paragraphs, so they have no reason to keep going” is.

This matters for your own work. Writers who can diagnose their drafts clearly edit faster and better. Those writers stop putting band-aids over symptoms and start fixing causes.

It matters even more when you’re reviewing someone else’s work, or when you’re working alongside AI-generated drafts (because that’s increasingly part of the job).

As teams generate more first drafts by more means, the human contribution shifts toward judgment – toward knowing what’s missing, what’s off, what needs to be rethought. If you can’t articulate what’s wrong and why, that judgment call isn’t available to you.

Editorial skill is learnable. It starts with reading copy the way a diagnostician reads a patient chart, not looking for what’s there, but looking for what the work is trying to do and whether it’s doing it.

Three questions to ask when diagnosing any piece of copy:

1. Does the reader feel recognized within the first two paragraphs?

2. Is there a clear belief the copy is trying to shift, and does it actually shift it?

3. Does the call to action follow logically from the argument built above it?

What Performance Literacy Means for Copywriters (And What It Doesn’t)

Writers don’t need to become analysts, but they do need to care about whether their work is doing its job.

Performance literacy for copywriters means maintaining a working relationship with data (e.g., open rates, click behavior, conversion trends, etc.). Not to become a numbers person, but to close the feedback loop between what you write and what happens when a real person reads it.

The writer who never looks at results is guessing every single time. Their intuitions might be good, but they’re not getting sharper because they’re not being tested against anything real.

The writer who only looks at results loses something else: their instincts, their voice, their willingness to try something that doesn’t have a precedent in the data.

What you’re after is informed judgment. You read the signals. You develop a point of view about what they mean. Then you make a call. That’s different from chasing whatever the numbers say, and it’s different from ignoring them entirely.

Closing the feedback loop doesn’t require a data background. It requires curiosity and a habit of asking: did that work? Why or why not?

How AI Tools Fit Into a Copywriter’s Workflow (And Where They Don’t)

Here’s where most conversations about the future of copywriting spend most of their time.

(Honestly, I’d rather spend less.)

Not because AI isn’t relevant. It is! And writers who are pretending otherwise are making a choice with real costs.

But the thing worth understanding isn’t how to use AI. It’s why some writers get so much more out of it than others.

The writers getting the most from AI tools aren’t the ones using them the most. They’re the ones using them most deliberately. They bring a clear question. They evaluate the output against their own judgment. They know what they’re looking for and they know when they haven’t found it yet.

The risk on the other side is real and worth naming: if you outsource your thinking to an AI tool, you don’t develop the judgment that makes you irreplaceable. You get faster at producing something. That’s not the same thing.

Where AI tools genuinely help copywriters:

• Pressure-testing a direction before committing to it

• Generating alternatives when stuck on an angle

• Surfacing patterns in performance data faster than manual review

• Drafting structural scaffolding to react to and edit

Where AI tools fall short:

• Determining what the work should accomplish

• Judging whether it’s accomplishing it

• Supplying the emotional authenticity that comes from lived experience, which, at the conversion layer, is what closes the gap between copy that reads fine and copy that actually works

I wrote about this in more depth earlier this year — specifically about the one thing AI can’t learn no matter how good your prompts get. The TL;DR version: at the conversion layer, emotional authenticity comes from lived experience. No input closes that gap.

The writers who will matter in the next ten years aren’t the ones who learned to prompt well. They’re the ones who kept sharpening the judgment that prompting is supposed to support.

The 4 Traits the Best Copywriters Will Share in 2035

The next generation of strong copywriters won’t be defined by how much they can produce, and they’ll likely share these four traits:

1. They think before they write. Strategic clarity about audience, moment, and belief-shift happens upstream of the draft.

2. They diagnose, not just produce. They can name why a piece isn’t working and fix the cause, not the symptom.

3. They close the feedback loop. They treat performance data as a sharpening tool, not a report card to ignore or a script to follow.

4. They use AI deliberately. They bring judgment to AI outputs rather than delegating judgment to them.

None of these are new skills. But in a landscape where production volume is increasingly cheap, they are the skills that compound fastest, carry the furthest, and matter most when the tools change again.

And they will change again.

So the real question worth sitting with: how much time do you spend thinking about the problem before you start solving it?

Your answer could very well separate you from the pack.

Subscribe now

Welcome to the 127th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Clarity = respect

• AI Tip: Opus is your strategist. Sonnet is your workhorse.

• Writing for Email: A Copywriter’s Accessibility Guide (via Action Rocket)

• Paid Isn’t Dead. But Your Playbooks Need an Upgrade (via MKT1)

• AI Adoption Fails at the Human Level (via MarTech)

• Podcast Pick: How to Enter “Flow State” on Command w/ Steven Kotler

• Swipe File Additions

• Job Opportunities

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Unclear copy isn’t just a writing problem. It’s a respect problem.

When your brief is vague, your writer has to guess what you meant.
When your feedback is ambiguous, your editor has to guess what you want.
When your messaging is muddled, your customer has to guess what you’re selling.

And guessing is expensive! It costs time, creative energy, and trust.

Clarity removes decisions people shouldn’t have to make, and that’s true whether you’re writing for a customer or writing a brief for your team.

The principle: clarity is a form of kindness.

Write clearly, and you respect everyone downstream.

AI Insight of the Week

Opus is your strategist. Sonnet is your workhorse. Know which one the task actually requires.

Most people pick a model once and stick with it, but that’s leaving performance on the table.

Opus thinks harder. It’s better at nuanced reasoning, complex strategy, and tasks where the quality of the thinking is the output. If you’re stress-testing a positioning angle, mapping a content strategy, or working through a genuinely difficult brief — that’s something to use Opus for.

Sonnet, however, executes faster. It’s better at high-volume drafting, iteration, formatting, and tasks where speed and consistency matter more than depth. So if you’re generating subject line variants or reformatting a document, Sonnet gets you there quicker (and cheaper).

Match the model to what the task actually demands. Thinking or doing. That’s the whole framework.

Must-Read Articles

Writing for Email: A Copywriter’s Accessibility Guide (via Action Rocket)

Why I recommend it: A quick accessibility checklist for email copywriters. From writing CTAs that say what they actually do (not “click here”) to why caps and italics reduce readability for the people who need clarity most, these simple shifts make your emails work for everyone, not just the easiest audience to write for.

Paid Isn’t Dead. But Your Playbooks Need an Upgrade (via MKT1)

Why I recommend it: Paid isn’t dead, but the playbook of picking a channel and hoping for the best is. Emily Kramer makes the case for audience-first paid: enrich your accounts, load them into every platform, build suppression lists, and let paid learnings feed organic (and vice versa) instead of running them in silos.

AI Adoption Fails at the Human Level (via MarTech)

Why I recommend it: The biggest blocker to AI adoption isn’t the technology, it’s the scar tissue from every failed software rollout that came before it. This breaks down 5 psychological fears that keep leaders from saying yes (loss of control, identity threat, transition cost, shame, and past failure) and a practical framework for earning trust before you pitch the tool.

You Should Read This Too:

BIG THINK
How to Enter “Flow State” on Command w/ Steven Kotler

👉 Watch on YouTube

Why I recommend it: Flow isn’t a personality trait – it’s a neurological state you can engineer. Steven Kotler breaks down the triggers that drop you into it (complete concentration, novelty, risk, the challenge-skills sweet spot) and why the best creative work tends to happen when you stop trying to focus and start building the conditions where focus is inevitable.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

BIC

Format: Ad
Spotted By: The Ads Professor
Why I like it: Another example of how words and images can work together. Without the image, the words make no sense. Without the words, the image has no context.

STILL HERE

Format: Email
Why I like it: This didn’t feel like an email campaign – it felt more like a snippet out of a magazine. I also loved the social proof piece and how it was story-led. Wonderful!

COLUMBIA

Format: Email
Why I like it: Subject line = 🔥 But also goes to show that a headline and sub-headline are all that you need for a good apparel email.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Marketing Manager

• Senior Copywriter

• Group Copy Supervisor

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 126th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: There’s a line between persuasion and manipulation.

• AI Tip: Your Project knowledge base is only as good as what you leave out.

• How to Rot Your Brain with AI (via Ruben Hassid)

• No, a headline tweak won’t fix your differentiation problem (via Diane Wiredu)

• You’re Wasting Your Highest-Intent Shoppers (via Eli Weiss)

• Podcast Pick: How to Influence & Sell to Anyone Using Imagination (via Joanna Wiebe)

• Swipe File Additions

• Job Opportunities (it’s back!)

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

There’s a line between persuasion and manipulation.

Too many copywriters and marketers don’t know where it is.

Persuasion helps someone see a real problem (and the path forward) more clearly. Manipulation exaggerates, distorts, or invents one.

Persuasion says: here’s what’s actually at stake, and here’s how this helps.
Manipulation says: things are worse than they are, and you’re running out of time.

The reason this matters isn’t just ethical, it’s practical. Manipulation might convert once. But it attracts the wrong customers, potentially spikes refunds, and quietly destroys trust in your brand.

Good copy doesn’t manufacture urgency. It reveals it.

If the problem is real and your product actually solves it, you don’t need to exaggerate anything. Just make it clear.

AI Insight of the Week

Your Project knowledge base is only as good as what you leave out.

Your instinct is probably to upload everything. Brand guidelines, tone docs, past campaigns, product specs, competitor research, etc.. You think, more context feels like better context.

But… it isn’t.

Claude pulls from everything in that knowledge base when it responds. EVERYTHING. Bloat it with tangentially relevant material and you dilute the signal. The important stuff has to compete with everything else you threw in.

Think of it like onboarding a new hire. You don’t hand them every document the company has ever produced. You give them what they need to do the job well, and nothing more.

For most Projects, that’s three things: who the brand is, who the customer is, and what good output looks like.

Everything else is noise until proven otherwise.

Must-Read Articles

How to Rot Your Brain With AI (via Ruben Hassid)

Why I recommend it: You can outsource your thinking to AI, but you can’t outsource your understanding. Ruben Hassid walks through his full 5-step workflow — from loading real context to treating Claude’s first draft like a junior intern’s work — and makes the case that if you finished an AI task in two turns, you stopped too early.

No, a headline tweak won’t fix your differentiation problem (via Diane Wiredu)

Why I recommend it: Most “copy problems” are messaging problems, and most messaging problems are positioning problems. Diane Wiredu makes the case that differentiation doesn’t live in a tagline, it lives in the gap between what you think makes you special and what your customers actually value.

You’re Wasting Your Highest-Intent Shoppers (via Eli Weiss)

Why I recommend it: Three flows and a welcome series is not a retention program. Eli Weiss breaks down why most brands’ email revenue is propped up by one flow while the rest of the lifecycle sits empty, and why lazy discounting trains your best customers to wait you out instead of buy.

You Should Read This Too:

JOANNA WIEBE
How to Influence & Sell to Anyone Using Imagination
Watch on YouTube

Why I recommend it: Five frameworks for living in your customer’s imagination — from flipping the status (Nespresso didn’t make better coffee, they made you feel better for choosing it) to giving them a superpower (Stripe didn’t sell payments, they sold “you can build now”). Each one works by changing how the customer sees themselves, not how they see your product.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

PLUTOTV

Format: Email
Why I like it: Two things I enjoyed about this email: 1) The hero’s image + headline pair; and 2) the CTA button for the X-Files module.

ROBBINS

Format: Sign
Spotted By: Jade Trott and Lee Trott
Why I like it: A great glimmer of a brand’s personality in action. It doesn’t take much to surprise and delight your reader – just intention (and bravery).

HISCOX

Format: Ad
Spotted By: Vikki Ross
Why I like it: Yeah, it’s hard to read, but it sure does stand out compared to everything else next to it. Next time you’re writing a subject line for an email or an ad for Meta, think about what everyone else’s creative is going to look like – then do the opposite.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

Job Opportunities

• Email Marketing Specialist

• Digital Marketing Specialist

• Senior Copywriter

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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Welcome to the 125th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Your copy isn’t just your words.

• AI Tip: Voice-to-text + Claude

• What does writing with AI actually feel like? (via Psychology Meets Writing)

• Suggest Practical Items to Reduce Cart Abandonment (via Science Says)

• Your Users Give You 30 Seconds: Here’s How to Make Them Count (via OneSignal)

• Podcast Pick: How to Generate Your Best Ideas (via Simon Sinek)

• Swipe File Additions

Interested in sponsoring an issue of the Weekly Round Up? Beginning this summer, I’m accepting select sponsorship opportunities. Click here for details.

Copy Tip of the Week

Your copy isn’t just your words…

It’s how fast you respond to a support ticket.
It’s the font you chose.
It’s the placeholder text in your form fields.
It’s whether your 404 page sounds like a human or a legal department.

Every element of your brand communicates something. None of it is neutral.

That’s what “Everything Speaks” means. And most brands only think about copy when someone’s actually writing words, which means they’re ignoring 80% of what’s actually being communicated.

Your customers don’t separate “the design” from “the message.” They experience all of it as one thing. And they form an opinion about who you are based on all of it.

So the question isn’t just what does our copy say?

It’s what does everything say?

AI Insight of the Week

Voice-to-text + Claude is the fastest ideation loop most people haven’t tried.

Typing slows thinking. You edit as you go, second-guess word choices, and lose the thread. By the time the idea hits the page, it’s already been filtered.

That’s not *always* bad, but it is slower.

Voice doesn’t do that. You talk the way you think — messy, fast, associative. The idea stays intact.

Dictate into your phone, drop the transcript into Claude, and tell it to pull out the core idea, clean up the structure, or turn it into a draft.

You’ll go from raw thought to usable output in minutes without the friction of a blank page.

It’s not really a writing hack. It’s a *thinking* hack that happens to create a workable first draft.

Must-Read Articles

What does writing with AI actually feel like? (via Psychology Meets Writing)

Why I recommend it: A grieving writer couldn’t find the words for nine stories until she started writing alongside GPT-3. By the ninth draft, only two lines belonged to the AI. The follow-up to the MIT study piece, this one explores “rhetorical load sharing” and why your writing with AI will only ever be as good as you.

Suggest Practical Items to Reduce Cart Abandonment (via Science Says)

Why I recommend it: A cart full of fun purchases triggers guilt, and guilt triggers abandonment. Recommending one or two practical items alongside indulgent ones reduced cart abandonment by up to 21%. Based on 14 million ecommerce sessions, not guesswork.

Your Users Give You 30 Seconds. Here’s How to Make Them Count. (via OneSignal)

Why I recommend it: Your users open the app for 30 seconds between meetings… not for a 12-step onboarding tour. This is a practical walkthrough of “micro-journeys”: short, cross-channel sequences where every single touchpoint stands on its own and delivers value even if it’s the only one they see.

You Should Read This Too:

SIMON SINEK
How to Generate Your Best Ideas
📼 Watch on YouTube

Why I recommend it: Ask for 15 ideas in 48 hours — because the first three or four are obvious and the eleventh, twelfth, and thirteenth are where the real gold lives. Simon Sinek walks through his “dog pile” brainstorm method: no judgment, no senior leaders in the room, and a green/yellow/red sort that gets the best ideas into execution fast.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

AIR TRANSAT

Format: Ad
Spotted By: Joel Holtby
Why I like it: The power of comparison on full display.

BELLROY

Format: Email
Why I like it: I know I’ve been featuring Bellroy quite a bit lately, but this is a powerful campaign where they leverage the power of affirmations in such a way that it positions their products as a central role in each one. I wish I had thought of this…

GORUCK

Format: Email
Why I like it: Another that I’m sorry for including so frequently here, but whoever’s taken over GORUCK’s email program is killing it with story-based campaigns. This one shows how a 3-star review led to an entire pivot within a product line.

Classifieds

• Your ad here

• Your ad here

• Your ad here

• Your ad here

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

Are you new here? Thinking about subscribing? Here’s what else you can expect.

Subscribe now

Here’s how most burnout conversations go.

Someone on the team starts missing deadlines. Or they’re delivering work that feels hollow. Or they’re just quieter than usual, grinding through their days without much of the spark that made them good at this in the first place.

And the response, more often than not, is to treat it as a personal problem.

Rest more.
Set better boundaries.
Practice self-care.

As if the right morning routine could fix a fundamentally broken workflow. But that’s the wrong diagnosis, and a wrong diagnosis leads to the wrong cure.

Burnout isn’t usually a discipline problem. It’s a design problem.

And the reason that distinction matters so much is this: if burnout lives in the design, then fixing it requires looking honestly at the design — who built it, who maintains it, and who has the authority to change it.

That answer is more distributed than most people want to admit.

The System Nobody Designed for Sustainability

Most creative workflows weren’t built with creative capacity in mind… they were built for throughput.

Speed. Volume. Get it out the door. More drafts, faster reviews, tighter turnarounds. Not to mention, the metrics that get tracked are almost always about production, rarely about the conditions that make good production possible.

So creatives end up working inside systems optimized for output, not for the kind of deep, focused thinking that actually produces strong work.

They’re constantly context-switching between projects. They get feedback late, which means they rework things they already finished. Priorities shift mid-sprint. The brief arrives incomplete, and yet the deadline doesn’t move.

None of that is a personal failure. It’s a structural one.

The person who burns out inside that system isn’t weak, they’re just human! And humans aren’t designed to do their best creative work under sustained, low-grade chaos. Nobody is.

So before you reach for a personal solution to what might be a systemic problem, it’s worth asking: what exactly is the design doing here?

What the Senior Copywriter Actually Owns

Senior copywriters have more agency over their situation than they typically claim (that’s not a criticism — it’s just true). But with that agency comes real accountability.

You own your time architecture. When you do deep work, when you batch feedback reviews, when you protect the two hours in the morning where you actually think clearly — that’s yours to design. Nobody is going to do it for you, and waiting for permission is a strategy for staying stuck.

You own your creative standards. That means saying no (or at least saying “not yet”) to work that doesn’t have what it needs to be done well. No clear brief? No defined audience? No realistic timeline? Accepting that work anyway and then quietly struggling through it isn’t professionalism. It’s a slow leak.

And if you manage juniors, you own your influence on them more than you probably realize. The habits you model, the norms you tolerate, the standards you hold — those become the water juniors swim in. They’re learning from you whether you’re teaching intentionally or not.

But if you’re consistently overextended and you haven’t said anything to anyone, you’re just participating in the conditions that are wearing you down. That’s not blame. Again, it’s the truth. But there is a real difference between blame and ownership. Ownership just means you have more leverage than you’re using.

AI is genuinely useful here, by the way. Research, first-pass variations, reformatting, summarizing briefs — these are tasks that eat real time without requiring your best thinking. Building AI into your personal workflow intentionally creates breathing room for the work that actually needs you. But you have to build it in. It won’t happen by accident.

What the Leader Actually Owns

Leaders don’t just assign work, they also design the environment work happens in. And that’s a much bigger responsibility than most of them are walking around with.

Workload visibility is on you. Not what’s been assigned, but what’s actually on your team’s plate. Those are often very different numbers (and if you don’t know the difference, you’re managing a spreadsheet, not a team).

Priority discipline is on you. Every last-minute request that lands on your team’s desk without a corresponding removal from their list is a choice you’re making, even if it doesn’t feel like one. Scope creep doesn’t just happen. It’s allowed to happen.

Feedback quality is on you. Vague feedback creates rework. Late feedback creates invisible overtime. If your team is regularly reworking things they thought were done, that’s not a creative problem — it’s a process problem, and it lives upstream of the creative.

Recovery time is on you. Not just between big projects, but within them. The assumption that creatives will naturally recharge between sprints is almost always wrong, especially inside organizations that treat every quiet moment as an opportunity to add more to the pile.

The most common leadership failure in creative environments isn’t malice. It’s assumption. Assuming people are fine. Assuming strong work means strong capacity. Assuming that because no one has complained, everything must be working.

A leader who doesn’t actively protect creative capacity is passively eroding it. That’s not a harsh statement. It’s just how systems work.

AI can help here too — workflow data and simple tracking tools can surface overload signals well before they become burnout signals. But the data only matters if someone with actual authority looks at it and does something.

Where These Two Things Meet

You can build a genuinely thoughtful personal system and still burn out inside a broken organizational one.

A leader can design a genuinely supportive environment and still watch someone burn out because they never learned to protect their own time or ask for what they need.

Both are real. Both happen regularly. And this is exactly why individual solutions and systemic solutions have to coexist. Neither one is sufficient on its own.

For senior copywriters who manage juniors, you’ve felt what a broken system does to a person. You know what it costs. You also have a hand (maybe a larger one than you think) in shaping what your juniors experience day to day.

That’s not a small thing. It’s actually kind of a significant one.

The goal isn’t to make everyone maximally productive, it’s to build conditions where people can do genuinely good work without quietly paying for it in ways nobody tracks.

The Reframe

Burnout isn’t a sign that someone isn’t tough enough.

It’s a signal that the design failed somewhere. The question worth asking isn’t “why can’t this person handle it?” It’s “what in the system made this inevitable, and who had the authority to change it?”

Usually, the honest answer points in more than one direction.

So here’s where to start.

If you’re a senior copywriter: what’s one part of your workflow you’ve been tolerating that you actually have the authority to change?

If you lead creatives: when did you last ask your team what they need to do their best work — and actually change something because of the answer?

Pick one. Start there.

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Welcome to the 124th edition of the Weekly Round-Up — your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and more!

In this week’s issue:

• Copy Tip: Structure vs. Style

• AI Tip: Prompts = Assets

• Show Your Marketing Boss Who’s Boss with Email Opt-Outs (via CMSwire)

• Signposting: How to Reduce the Cognitive Load of Your Reader (via Wes Kao)

• 4 language psychology secrets from your competitors (via the Growth Tribe)

• Podcast Pick: The New Avatar Framework (How to Build Avatars That Scale in 2026)

• Swipe File Additions

Copy Tip of the Week

A lot of copywriters and copy editors think that “editing” is just making things better.

But too many younger editors only focus what’s on the surface and ignore what’s underneath.

Because what’s underneath is usually harder to fix.

I’m talking about *structure*, and no matter how hard you try, you can’t polish your way out of a structural problem.

If a piece of copy isn’t landing, most writers do what feels productive – they tighten sentences, swap words, add a stronger verb here, and cut a weak adjective there.

And yet, the copy still doesn’t work.

It’s not because the editing is bad. It’s because the problem isn’t in the sentences. It’s in the skeleton underneath them.

Here’s what I mean by skeleton: the logical sequence of your argument. The order in which you introduce the problem, the stakes, the solution, and the proof. Basically, the reason a reader should keep going.

If that sequence is broken, no amount of sentence-level polish fixes it. You’re just decorating a janky frame.

So before you edit a single word, ask: does this move in the right order? Does each section earn the next one? Is the reader being led somewhere, or just standing in place?

If the answer’s no, stop editing and restructure things first.

The words come last.

They always do.

AI Insight of the Week

A great prompt is an asset. Start treating it like one.

Most people write a prompt, get a good output, and move on. The problem is that it disappears into chat history and they rebuild it from scratch next time — slightly different (and slightly worse).

When a prompt consistently works, save it! It encodes your standards, your constraints, your audience context. Everything you’d otherwise re-explain every single time.

Then, keep a running doc of your highest-frequency prompts (e.g., subject line generation, offer angle brainstorming, first-draft briefs, etc.). Write the prompt once — *carefully* — and save it.

Worth capturing alongside it: what it’s for, what model it performs best on, any negative constraints that make it sing. Basically, treat it like a SOP.

A prompt you refine once and use weekly pays back every week.

Must-Read Articles

Show Your Marketing Boss Who’s Boss with Email Opt-Outs (via CMSwire)

Why I recommend it: Less than 1% of your list will opt out of Mother’s Day emails — but some of them are your highest-LTV customers. Chad White walks you through the exact conversation to have with your boss about why giving subscribers the choice protects revenue, not costs it.

Signposting: How to Reduce the Cognitive Load of Your Reader (via Wes Kao)

Why I recommend it: Your reader shouldn’t have to finish a sentence to know why it matters. Wes Kao breaks down “signposting” — starting sentences with phrases like “the surprising thing is…” or “the most important part to keep in mind is…” — so your reader’s brain can organize information as it arrives, not after.

4 language psychology secrets from your competitors (via the Growth Tribe)

Why I recommend it: Four language psychology principles that should govern every word across every channel — from the Pratfall Effect (why admitting a flaw builds trust) to Negation Blindness (why “no hidden fees” makes people think about hidden fees). Research-backed, example-heavy, and directly applicable to your next email or landing page.

You Might Also Like:

BRAIN DRIVEN BRANDS
The New Avatar Framework (How to Build Avatars That Scale in 2026)
🎧 Listen on iTunes | Listen on Spotify

Why I recommend it: The customer avatar was invented by a software developer who asked “what would Kathy do?” — not “who is Kathy?” Sarah Levinger and Nate make the case for reordering the avatar framework: start with when someone needs you, then why, then who — because a Taco Bell drive-through at midnight has a Bentley and a beat-up Nissan in the same line.

🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.

Pretty Fly Copy

GREATER ANGLIA

Format: Ad
Spotted By: Sam Plant (LinkedIn)
Why he likes it: The best PSA copy doesn’t dress the message up. It finds the smartest, most memorable way to deliver it, without being so smart that it flies over people’s heads.

OLUKAI

Format: Email
Why I like it: Dead simple and I thought it was a joke until I realized it wasn’t.

WHOOP

Format: Ad
Spotted By: The Ads Professor
Why I like it: A wonderful play on lyrics words.

That’s it for this week! If you have questions or comments — drop a note below.

✌️
Matt

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