Kevin Rogers On Embracing Your Creative DNA And Practicing With Purpose

Whether you’re new to the copywriting industry or have been in the game for years, there are certain names that stand out. Kevin Rogers is one of them. Comedian, podcaster, radio host and freelancing mentor, Rogers is known as the Copy Chief.

Stoic Athenaeum caught up with Rogers on some of his latest projects, the copywriting lessons he learned from his former life as a stand-up and his writing philosophy.

Thanks for taking the time to chat about your experiences Kevin. You’ve earned a reputation for being an industry leading copywriter through Copy Chief and other ventures. For those who’re unfamiliar with your journey, how did you get involved with copywriting to begin with?

The way I got involved with copywriting was through working for a friend’s company, which was a marketing company and he hired a consultant to come in and rewrite some phone scripts.

And this guy was a direct response junkie called Chris Thomas Soulo. He’s known as Dr. Soulo, although he doesn’t have a PhD. He was always obsessed on direct response and he’s the guy who turned me on to Gary Halbert and John Carlton. He turned me on to the whole industry.

I started reading Dan Kennedy books and started reading John Carlton’s blog. And I was just like wow. You know what went from this sort of strange hobby the guy had suddenly started to have context.

Soulo thought I was a pretty good writer and so I took the only course that was available at the time, which everyone referred to as the AWIA course. After that I was kind of stuck. I knew I loved it.

In another life you were a stand-up comedian and I’d love to know how that career helped to shape you as a copywriter and the role you think humour plays in effective content marketing.

The most immediate parallels that I discovered were this instinct you develop as a writer was heavily influenced by the instinct you develop as a comic, which is to hold and keep an audience’s attention.

The glaring difference with writing is you don’t get any immediate feedback, right? And with comedy, you get immediate feedback, sometimes in the form of a boos and hisses.

I think every writer must have this instinct in some way to know when something’s dragging on or getting boring and a lot of that comes out in editing.

But there’s an instinct you have when you’re in that moment and you’re sitting there. Whether it’s you in a live audience or you and the blank page something take over that’s beyond you.

I think comedy allowed me to develop a good instinct for knowing your avatar and making copy conversational because I’d had so many one-sided conversations with live audiences.

What is your definition of ‘good content’ in today’s fast-paced and saturated world of digital marketing?

Honestly, that’s a really good question. It’s interesting to me when I scroll through my Instagram like we all do and look at what stops me. It’s amazing when you’re scrolling through Reels or Stories, especially how immediately you choose to click past something if there’s no relationship there.  Something once in a while will stop you and put you down a rabbit hole.

And I always try to reverse engineer and go, whoa, where did this start? And what about that compelled me?

I think human connection is always the thing and it has to have this feeling of the creator not having their agenda on display out of the gate.

If you find yourself chasing trends, I think you’re already too late. Innovating through authenticity. That’s the mark of good content.

In addition to Copy Chief, you also run the Copy Chief Radio podcast. What was the inspiration behind the podcast and what do you think are the best practices for setting up in that medium?

The podcast thing was very natural for me. I wanted to be in radio first and the way I got into stand-up was through wanting to be on radio.

My first comedy mentor was in radio. He was a comic who was big on the radio and he asked me ‘what do you want to do?’ And I’m like ‘I might just want to be a DJ. It seems like the best job in the world.’

And he’s like ‘nah, that’s a dime a dozen, you might as well drive a truck. If you can develop your humour then you’ll have leverage forever in this industry. So why don’t you go learn to be funny by doing stand-up and then see if you want to come into radio.’

I never did go into radio. I just stuck to stand-up. But then when I found copywriting I was doing a radio show with a friend of mine. I’ve loved talking into microphones as long as I can remember. So the podcast was very organic for me.

Copy Chief Radio is great. I have four different types of episodes exploring different ideas. The next show I’m the most excited about doing is one called The Freelancer’s Journey, where I talk to entrepreneurs who are service providers and learn from them and how they succeeded in their careers.

Compared to other types of writing, how would you say copywriting is different and how would you describe your specific type of writing style?

What I tell people is the difference between content and copywriting is that content is there to fill space in a meaningful way. Certainly it has a purpose. Copy is judged solely on its ability to convert an action.

You could be on retainer for years with a client writing blogs and as long as your writing is  good and you’re reliable, you’re going to stay employed as long as they have a need.

With copy it’s a little bit more like you’re a gunslinger coming into town to shake things up, or you’re a detective like Colombo and you come in and you investigate who murdered your conversions and  see if you can set things right.

You’ve also made a career of mentoring and coaching other freelance writers. What are some of your most successful coaching packages and how have they helped other creatives get to where they need to be?

I run a programme called The Freelancer’s Journey Accelerator. It’s seven phases of a freelancing career where participants are given the tools to grow their business.  Phase one is finding the thing you would love to do to get paid for. Phase two is proving the model that you could actually get paid for it.

Phase three is setting a standard for how people hire you. And so you’re not just taking all the work that comes your way, you’re treating it like a business. Phase four is really stabilising that business. Phase five is scaling that business with creating new revenue streams e.g. working with high level clients.

Phase six is going beyond client money where you’re becoming unavailable to clients. You’re making more money from your own products or you’re consulting on high-level stuff than you are fulfilling projects.

Phase seven is building your legacy business, where you’re building a brand that will thrive beyond your investment in it.

I’ve lived and coached all seven of these phases and do so daily. So that’s the most successful programme. Literally life-changing stories from people who didn’t know how to manoeuvre their career or who’ve been feeling stuck for years.

How would you say a content marketer should go about bringing true value to their clients?

It’s about bringing creative ways in to optimise attention. The content is there to win and keep attention and obviously educate and provide value.

I’ll flip it a little and say the best way a content marketer or any freelancer can provide value is decide how they want to work. Do they want to be order-takers or do they want to be innovators?

There’s a balance between those things at all times, depending on the client. But I would want to inspire every creative service provider to always be pushing themselves and allowing fresh ideas and innovative things to emerge.

The greatest value you can bring is to have a standard of how you operate where clients are meeting your standard. You’re just not checking boxes for them solely. You’re bringing something to the table that you can uniquely provide based on your own creative DNA that no one else could quite provide the way you can.

What would your best advice be for a freelance copywriter who is starting out?

I could go on forever about this one, but I would say just get paid and find an outlet for your work and practice it with purpose. It’s challenging to practice on your own. I find you can only hand copy sales letters or practice writing emails and things for so long before it starts to feel masturbatory.

Even if you’re practicing with purpose without pay you’ll still build a rhythm and foundation. One of my first gigs involved a guy coming to my house to sell me lawn service I couldn’t afford but I got to chatting with him on my doorstep.

He started to get excited about the idea of direct response copy and we decided to test a sales letter together. I was happy to do it without pay because I wanted to write something and actually have it delivered and be right.  It was a successful project and it was validating for me.

If you’re in a community around people who need your service and you’re unproven you could say ‘Hey, look if you don’t have a budget right now, let’s create some revenue together and we’ll do a deal on the back end of it.’

Who are some other copywriters and marketers you admire past and present?

John Carlton is my copywriting hero. My great friend and mentor.  Gary Benza Vang is probably my number two right up there with John as a writer. I really admire how they approach the craft.

I also love what Aaron Dohuk and his team are doing over at Banyan Hill Publishing. They’re in the cutthroat world of financial newsletter publishing and they’re doing some cool and innovative things over there.

Whether in business or personal affairs, everyone develops their own philosophy of life. What would you say yours is and how do you try to implement it day to day?

I don’t want to sound lofty or Pollyannish here, but I’m fortunate to be in a place in my career and in my life where I really do get to focus every day on just providing value to my community members, my audience and my family.

So I would say my philosophy is how can I get better every day at something that I have to do all the time e.g. building a community, putting it first over sales and continuing to trust in the integrity that’s been created.

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