Weekly Round Up #109
Your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and much more!
Welcome to the 109th 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 much more!
In this week’s issue:
Copy Tip: The Fundamentals That Actually Compound
AI Tip: Using AI to Surface the Questions You’re Avoiding
What’s Next for DTC (via Retail Brew)
Customers Expect Empathy. Here’s How to Deliver It. (via HBR)
The Psychology Behind High-Converting Email Campaigns (via Foundr)
The 5-Question Filter for Every 2026 Marketing Trend (via The Copy Minimalist)
Podcast Pick: DTC Podcast Ep 573 – Where Should That Click Go?
Copy Examples for Your Swipe File: Aventon, Bellroy, Howler Brothers
Recent Job Openings: Acorns, Consensys, Stripe, Uproot Clean, and SimplePractice
Copy Tip of the Week
Most copywriters want a shortcut.
There isn’t one. But there are fundamentals that compound over time if you stick with them.
Read widely.
Not just marketing and copywriting books. Read fiction. Read history. Read things that have nothing to do with your field. The best writers steal from everywhere.
Write every day.
Set a word count minimum and don’t stop until you hit it. Don’t worry about perfection. Worry about putting in the reps.
Publish before you’re ready.
Keeping your work to yourself feels safe, but it’s also how you stay stuck. Ship it. Nothing forces you to ditch your ego faster than feedback from strangers online.
Write by hand.
A legal pad and a cheap pen force you to slow down. You’ll write with more intention when you can’t just delete and start over.
Write to one person.
Forget “audiences.” Picture a single reader sitting across from you. Your message will land a lot harder when it feels like a conversation instead of a broadcast.
None of this is glamorous. That’s the point.
The writers who actually get good are the ones doing the boring work while everyone else hunts for hacks.
AI Insight of the Week
Most people use AI to answer questions.
High-leverage people use AI to surface the questions they’re avoiding.
The real constraint in good work is rarely effort or information. It’s the unasked question sitting quietly in the room, shaping everything.
AI is very good at finding those… if you ask it to.
AI doesn’t have ego, sunk cost, or emotional attachment. It will calmly point at the uncomfortable thing you’re dancing around.
And that’s where the leverage is.
Instead of prompting for an answer, run your work through one of these prompts before you move forward.
1. The Avoidance Prompt
“What is the most important question I might be avoiding here because it’s uncomfortable, inconvenient, or challenges my current plan?”
2. The Assumption Check
“What assumptions am I treating as facts, and which of those would break this plan if they’re wrong?”
3. The Outcome Reversal
“If this fails, what’s the most likely reason, and what question should I have asked earlier to prevent that?”
AI doesn’t make you smarter by giving better answers.
It makes you smarter by forcing better questions earlier.
That’s how you avoid wasted effort, bad bets, and “why didn’t we think of this sooner” moments.
Must-Read Articles
What’s Next for DTC (via Retail Brew)
🔗 Read it here
Why I recommend it:
AI is making it dead simple to crank out ads and content, which means the stuff that actually matters now is what’s hard to fake—distinctive brand voice and genuine human connection. Worth a read if you want a clear-eyed look at where your skills stay valuable as DTC shifts under everyone’s feet.
Customers Expect Empathy. Here’s How to Deliver It. (via HBR)
🔗 Read it here
Why I recommend it:
Most companies say they care about customers, but the data here is stark—78% of people don't buy it, and nearly half have ditched a brand over it. Empathy isn't a vibe, it's a trainable skill that moves the needle on loyalty and revenue, and the brands figuring out how to blend AI efficiency with genuine human moments are the ones pulling ahead.
The Psychology Behind High-Converting Email Campaigns (via Foundr)
🔗 Read it here
Why I recommend it:
This one's a solid refresher on the four psychological levers—urgency, scarcity, social proof, personalization—that make emails actually convert. Nothing groundbreaking if you've been in the game a while, but the example email at the end ties it all together in a way that's worth stealing from.
You Might Also Like:
DTC PODCAST
Ep 573: Where Should That Click Go? Landing Pages, Home Pages, and PDPs
🎧 Watch on YouTube | Listen on Spotify
Why I recommend it:
The core insight here is simple but easy to forget: landing pages let you control the message sequence in a way your homepage never can – especially useful when you need someone to understand value before they see price. Good listen if you’re thinking about where your traffic should actually land, not just how to get the click.
🔓 Want access to my entire swipe file database?
Subscribe here to unlock the magic link.Pretty Fly Copy
AVENTON
Format: Email
Why I like it:
Honestly, design-wise it was fantastic – an attractive teaser campaign for a new product. The use of the GIF to drip copy was great too!
BELLROY
Format: Email
Why I like it:
This email took a particular product line and framed it around decision-making and philosophy – which inspired the line itself. It’s a little long, but it’s well-done.
HOWLER BROTHERS
Format: Email
Why I like it:
I loved the subject line: “Got some holiday cash to burn?” It was the perfectly-timed email post Christmas Day when, more than likely, your target customer does have holiday cash to burn!
Career Opportunities
These remote opportunities are updated every week with copywriting and marketing roles ambitious job-seekers should definitely apply for.
Sr. Copywriter at Acorns
📍Remote ℹ️ FinTech 💸 $62 - $67/hr (USD)
Senior Creative Copywriter at Consensys
📍Remote ℹ️ FinTech 💸 $128,000 - $153,000/yr (USD)
Writer, Content Marketing at Stripe
📍Hybrid (ATL) ℹ️ FinTech 💸 $143,000 - $214,000/yr (USD)
Direct Response Copywriter at Uproot Clean
📍Remote ℹ️ DTC 💸 Undisclosed
Senior Performance Copywriter & Content Strategist at SimplePractice
📍Remote ℹ️ MedTech 💸 $100,000 - $125,000/yr (USD)
That’s it for this week! If you have questions or comments — drop a note below.
✌️
Matt
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