Interview with Joe Cunningham: Freelance Copywriter

Are you sometimes sat struggling to generate emotion with your readers? I know I did, that’s why I reached out to Freelance Copywriter Joe Cunningham to give my marketing content a much-needed pulse.

Hey Joe,

We recently connected after I consumed a number of articles and videos you produced on copywriting.

Not only did I enjoy your content but it resonated with me. So, we jumped on a call and shortly after began working together.

I am excited to discover your journey as a copywriting professional, how you get inspiration, and ultimately your secret sauce for bringing copy alive.

So, Joe, let’s jump straight into this with my first question.

It would be great to get a little background information from where you were born to where you live today. What’s your backstory?

Adam, thanks for having me on Life Hacker Guy!

I was born in Pennsylvania, U.S. and lived near Philadelphia until I was 14. Then my family started moving to a new state every 1–2 years for my dad’s career. I’ve lived in 7 different states and had more than a dozen addresses.

Moving a lot means you’re always the “new guy,” which felt lonely and isolating during my teenage years. But it taught me how to connect with people from completely different lifestyles, regions, and experiences than mine. It also helped me appreciate the variety and beauty of human beings—things I draw on every day to write copy.

I also got to do things like rope cattle in Texas and ski the White Mountains in New Hampshire.

But moving is exhausting, and I’m grateful to be home again in Pennsylvania and living in the same town for 9 years. I don’t see myself moving again.

You only became a full-time copywriter in 2021, how did you get into it and how was your first year?

Copywriting was my first job out of college. I finished my last exam, had lunch with the founder of a web development company, and boom, I was writing copy.

But though I’ve worked in marketing jobs for more than 10 years, I didn’t take copywriting seriously until I was treading water as the marketing-army-of-one at a nonprofit.

That’s when I encountered Ogilvy on Advertising by David Ogilvy, one of the godfathers of advertising. His book changed my life.

Everything Ogilvy described corresponded to something in me: the purposeful, strategic nature of copywriting, the basis in research and human psychology, the combination of art and science, the drive to help humans live enriched lives, and the value of helping clients succeed in their businesses.

I knew I had to become a copywriter…and it was time to make a career shift.

So after studying copywriting for 2–3 years, taking courses, reading books, and practicing it in-house (and getting good results with it), I quit the nonprofit life and started freelancing full-time.

I went in with six months of savings and no expectations. I didn’t know if I would make money, or if I would flop.

Turns out I did make money my first year…up 75% of my full-time salary, which is wayyy more than I expected.

And my second year is already off to an incredible start, in terms of the amazing clients I’m working with and the income I’ve already got lined up.

Hard to see myself turning back. 🙂

I have seen a few of your videos that outline your approach to writing copy for clients, could you outline your method here?

Yeah, so my method isn’t anything crazy or ground-breaking. Here’s what I do.

First (and you’ll remember this part, Adam), I get to know the client’s business and business challenges.

I like to ask lots of questions about their goals, obstacles, the market they’re in, who they’re trying to serve and sell to, who their competitors are, which brands do they draw inspiration from, why did they choose their price point, what’s their vision for the business or their marketing, what have they tried that didn’t work, and so on.

I go pretty deep with this because context is EVERYTHING in marketing.

Next thing I do is research their audience. Surveys, interviews, testimonials, Reddit threads, Facebook groups, TrustPilot reviews, and so on. I copy and paste the common pain points and problems and successes and save them for reference.

Then I wireframe the copy in a Google doc using tables to create elements and buttons. That helps me (and the client) visualize the copy and understand the hierarchy of elements and the structure of the copy.

I write the first draft. I don’t edit, I just write. I pound out dozens of headlines, I pound out bullet points, I spit out a bunch of body copy.

Then I walk away. If I can give it two days, awesome. But usually, 24 hours of separation is best.

I come back and edit. Then edit, edit, edit some more. I try out new ideas and trash bad ones.

And when I feel I’ve done enough editing, I deliver it to the client.

Do you get writer’s block and what helps you overcome it?

If I get writer’s block, I know it’s because I haven’t done enough research.

We copywriters can’t make stuff up…it has to be grounded in the goals of our clients, the aspirations and problems of our audience, and the context of the copy.

So if I’m feeling blocked, it usually means I need to re-read the research, revisit customer testimonials, and so on.

Or it’s time to work out and get the blood flowing.

What are the top mistakes that business owners make with the copy you see? How do you fix these?

Hmmm…great question Adam.

First thing? Talking about the business instead of the customer. That’s the biggest one.

I see a lot of businesses say things like “we’ve been in business 37 years” or “integrity, customer service, and excellence and innovation” or something like that.

Trust me, nobody cares.

A simple fix is replacing “we” words with “you” and turning those claims or promises into tangible benefits to the customer. Make it about them. Show them how your business improves their day-to-day life. Goes for B2B and D2C!

Another thing I see a lot is companies trying to be clever or outrageous instead of helpful.

Don't get me wrong, I'm all for big ideas. They’re essential to great campaigns and effective copy. But while people are smarter than you think, they’re also busier than you think. They have enough stimuli, and another advertisement or offer that feels self-serving is getting ignored.

The biggest ideas are simple. Really, really simple. And I think marketing and advertising would go a long way if they focused on getting simple and clear than on being clever and bold.

The last thing I'll add is this: a lot of businesses think jargon is impressive. So they sound like academic abstracts instead of warm, breathing humans.

The best thing you can do is be human. People relate to real, natural voices, not jargon.

You have worked with a lot of great companies, including a powdered greens supplement (LOL), who else has or are your clients?

Haha, supergreen tonik is one of my favorite clients to date, and I’m not saying that to flatter you.

A few other clients I’ve had the privilege of working with include Huel, a complete food company (if you want your food to be 100% nutritious, and don’t mind powder-based meals, check them out), Stacked Marketer (one of the best marketing newsletters around), and Caliber, which provides personalized and remote fitness coaching.

Also got to help Iris Creative, a nonprofit marketing agency, sell their live courses, and helped a couple who offers financial coaching with their homepage copy.

There are others, but I can’t name names. 🙂

What is the best type of client and are there types of clients you would avoid?

The best clients so far have been the ones who are trying to solve real problems and make a positive difference in their customers’ lives.

Whether it's fitness, or nutrition, or self-improvement…those are the clients I enjoy working with best.

I also find that I work best with in-house marketing teams or business owners. In those scenarios, we’re all partners trying to do the best work we can. I love that.

I tried the agency model a few times…it doesn’t work for me. You’re too removed from the client’s customers, there’s little interest in quality, and the turnaround times are ungodly short.

So, yeah, I don’t do agency work anymore.

Where do you get inspiration from?

All kinds of places. Martial arts training (I'm a black belt in taekwondo/hapkido), reading great advertisements, literature, history, art, the ocean, cocktails…even washing dishes.

I'm drawn to simplicity and purpose, so I love Hemingway’s writing, the artwork of Rene Magritte, mid-century modern design…things that have clean lines, clear contrast, and lots of space.

Are there any blogs/resources you recommend checking out?

Highly recommend reading and following Eddie Shleyner. He’s a master of copywriting, marketing, and content.

I’d also recommend reading Sarah Colley’s blog. She’s a true pro when it comes to content marketing.

Louis Grenier’s Everyone Hates Marketers emails are amazing, too.

Also, Katelyn Bourgoin. If you care about your customers, read her emails. You'll learn so much about psychology, buying triggers, and more.

Finally, a shameless plug: I send weekly emails that get into copywriting, marketing, and creativity. My readers seem to think they’re valuable…that’s all that matters to me.