Hello Reader!

Watching The Music Man with the kid the other night, and I had a copywriting epiphany.

This classic is a masterclass in buyer psychology + copywriting. It's all about selling people on a problem they didn’t know they had.

The Setup: River City is fine. Everything is just... fine.

The Hook: Along comes Professor Harold Hill (a grifter, but a great salesman (ahem... and copywriter, let's be real). He wants to make some cash and needs to sell the town on the idea of a marching band (and the high cost of instruments and uniforms).

How does he do it?

He talks about how good a band would be.

Just kidding... have you even seen the film/musical?

No! He pitches the Problem—the lurking, silent menace that will devour their youth:

“Oh, there is trouble, right here in River City! Trouble with a capital 'T' that rhymes with 'P' and that stands for Pool!”

Kids are going to play pool. And then they’re going to smoke cigars. And then they’re going to... gasp... SWEAR!

It's the fear of moral decay, wrapped up in a slightly sarcastic, over-the-top panic. He’s calling out the obvious (small-town boredom) and problematizing it.

The Copy Lesson: Don't Pitch the Band, Pitch the MORAL DECAY from the Pool Table

Your reader isn't waking up excited to buy your "cutting-edge cloud-based solution." They’re waking up to the tiny, annoying pain points that are giving them hives.

• You think they have no problem? Oh, yes, they do! They just haven't articulated it with capital letters and a dramatic chord progression yet.
• Your job: Name the pool table. Call out the "Trouble." Make the invisible itch painfully visible.
• The solution? A marching band! (Or, you know, your actual product.)

Once he’s got the whole town freaking out about the moral ruin of the youth, the solution (instruments, uniforms, big brass band) looks less like a $20,000 expense and more like the only path to salvation.

Outstanding!

TL;DR: Stop selling your features. Start selling the glorious, immediate relief from their silent, embarrassing pool-playing problem.

Thanks for reading,

​Ashley R. Cummings​

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Expert Interview | Keisha Singleton

1. Tell me more about yourself and your journey into content.

I’ve always loved writing. When I was eight, I wrote a little story during lunchtime that ended up becoming my school’s Christmas play, and I’ve been chasing that high ever since. I studied Theatre and English at university, spent my spare time interning for online publications, and worked as a waitress to support myself through it all. After uni, I kept juggling full-time work and unpaid internships, never quite getting the chance to focus solely on writing.

When I moved to Australia, I couldn’t find work at first, so I turned to Fiverr and started taking on writing gigs for $5 per 500 words, of which I kept only $3. It was an extremely humble start, but it taught me the discipline of writing for any brief, any audience, any topic.

That led to bigger gigs, contract positions, full time work and eventually where I am now: Senior Editor of a tech company’s blog.

My philosophy is that everything is interesting to someone, you just have to know how to make it engaging. I’ve written about everything from sustainable dog poo bags or SaaS solutions, and know that every topic has a story worth telling.

2. You're an editor of a standout publication (especially in the age of AI). What do you do to ensure the content you publish is aligned with your audience, interesting, and still gets visibility?

AI can give you everything but the human. That’s the core of our editorial approach. We focus on content informed by real experience by highlighting expert voices, using unique quotes, and incorporating visual storytelling that proves authenticity. EEAT (Experience, Expertise, Authoritativeness, and Trustworthiness) is the backbone of how we build credibility and connection.

We balance creativity with performance by giving our writers room to explore. While SEO, AIO, and GEO strategies guide our direction, writers are encouraged to pitch topics they’re genuinely passionate about or find fresh angles within our niches.

The world is becoming increasingly saturated with generic AI-generated content, but originality comes from experience. Anyone can share information, but not everyone can tell a story rooted in real insight.

3. You've interviewed a lot of independent entrepreneurs, and this newsletter is full of freelancers and solopreneurs. What is one piece of advice you'd give to encourage this group?

Invest in yourself. Find your voice, grow it, and trust it. Don’t try to be anyone else. The most successful founders and freelancers I’ve met have one thing in common: they lean into what makes them different.

So instead of trying to please everyone, focus on becoming absolutely loved by a few.

Must-Read Industry Content

Think smarter, faster: Each week, I share the articles that are shaping where content marketing is going, so you don’t have to dig.

1/ Good content framework (HDFO)​

2/ Why Your 2026 Marketing Strategy Should Lead (Not Follow) Your Technology Choices​

3/ Research day tips​

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