Weekly Round Up #129
Your once-a-week digest filled with copywriting insights, AI tips, must-read articles, pretty cool copy examples, and much more!
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
Job Opportunities
Marketing Data Analyst
RemoteEmail Copywriter (Agency)
RemoteContent Lead
RemoteSenior 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.