Kevin Rogers Steps Up to the Microphone

Next on my hit list of “DR copywriters to interview” is Kevin Rogers, direct response wordsmith, consummate funny man, and “head honcho” of John Carlton’s stable of copywriters.

In this interview, Kevin opens up about the challenges he faced getting started as a freelancer, how stand-up comedy helped him become a better copywriter, and the three commonalities among copywriters who experience fast success as freelancers.

Exclusive Interview
with Copywriter Kevin Rogers

Ryan Healy: When did you first become interested in freelance copywriting and how did you make the transition to being a self-employed freelancer?

Kevin Rogers: I was first introduced to direct response by a guy named Chris Tomasulo. He’s a brilliant marketer. The company I was VP of at the time hired him to consult. We struck up a fast friendship.

He knew I liked to write and turned me onto Carlton, Halbert, Fortin, etc. He was also a Dan Kennedy Gold Circle (or whatever it’s called) member, so we would listen in on the monthly calls together. It was a quick education in direct response. Plus we were running offline campaigns for the company, so I was getting to see the results of DR first hand — which is priceless.

I quickly developed the dream of becoming a freelancer. I read Carlton’s blog religiously. His stuff really hit me in the gut.

So I bought the AWAI course, even did the rote lessons and sent in the restaurant letter (hilarious to read now), but I was sort of clueless as to how to make the transition to working freelancer.

Then, by a fluke, I found out an old comedy friend, Vin Montello, was also studying the Masterson course. I couldn’t believe it. So we re-connected. He was already getting clients and mentoring under guys like Mike Morgan and David Garfinkel. He was very generous in sharing what he’d learned. Helped me get good fast. And turned me on to my first clients. The rest is hysteria.

RH: I’ve always heard it’s good to have face-to-face sales experience before transitioning to direct response copywriting, but I’ve never heard that it’s good to have experience as a stand-up comedian. How has your background in stand-up comedy helped you in your copywriting career?

KR: Ha. Good question. I wouldn’t recommend it for everyone, but there are several important crossover skills.

In a way, stand-up comedy is the ultimate face-to-face sales job because you have to close them on every joke.

Live comedy taught me how to capture and keep the attention of people who don’t want you to have it. There’s very little difference between drunks in a nightclub and distracted Internet surfers as far as attention spans go.

You have to grab them by the collar and shake them out of their “zombie state” as Carlton calls it.

I wrote a couple of guest blog posts for John about the similarities between stand-up and copywriting. (“Two Copywriters Walk into a Bar” and “The Art of Bombing”)

RH: When we last talked, you mentioned you now head up John Carlton’s “Stable of Copywriters”. How did you meet John? And how did you become his “head honcho”?

KR: Well, I’d kind of gotten lucky by knowing Tomasulo and Montello, so in the case of Carlton I was determined to create my own “luck.”

I mentioned that he was the guy I studied early on. Then as I began writing fulltime I developed a problem…

I fell into this trap where I was in constant “catch up” mode with my skills. I was starting to land some good clients and like any good freelancer I was eager to over deliver.

So, every time I would read a really insightful copywriting article on say, Clayton Makepeace’s blog (usually something by Daniel Levis) I felt like I HAD to add this new tactic into my current letter or I’d be cheating my client.

In a way it’s a good problem to have because it means you’re writing every day and honing your craft… but it can also drive you insane.

So, I made a decision to study only ONE copywriter and cut everything else out. Just focus all my energy on one top guy, and learn his methods so well that if I got stuck on something, it would be as if I could tap into his brain and find the solution.

That guy for me was Carlton, of course.

Call it “law of attraction” or whatever, but I studied John so intensely that, once we met (which became inevitable) it was like we were old friends. From there, the working relationship flourished and now we actually are good friends. It probably helped that we have a lot of common interests in music, comedy, etc.

The experience taught me how to create a calculated approach to getting inside someone’s head. Then if you are compelled to approach them, be sure to do it with the intent of offering them something useful. They already know they can help you, the question is: how can you help them?

RH: Out of curiosity, how does somebody go about becoming a “stud” in Carlton’s “Stable of Copywriters”?

KR: We’ve just begun actively recruiting new writers into the fold. Basically, unless you’re already in John’s world, the only way in is through the Simple Writing System. (John’s personal formula for writing sales copy proven to work best over his storied 30-year career.)

It’s a great system and if our team doesn’t already know a writer well, having them complete the course is the best way we can be sure they know enough to write a good letter — and that they’ll be on the same page with us.

That doesn’t mean everyone who goes through the course is qualified, but it lays a foundation for us to work from with new writers.

We’re hoping to create opportunities for writers at all levels to hook up with clients of all needs and budgets. Our goal is to take talented writers who can hit their deadlines and perform like pros and work them up through the ranks and connect them with high-level clients.

We’re looking for the win-win-win. John’s not interested in creating a factory of cub writers. But he is interested in helping good writers connect with good clients. That’s the simple premise of the Stable.

RH: So tell me what an average day looks like in the life of copywriter Kevin Rogers? Do you work a standard 9-5… or are you one of those night owls who doesn’t get fired up until about 10 p.m. at night?

KR: No. I’m in total dad mode. Up at 6 or 7 AM with the kids. I try to write first thing in the morning before the biz stuff takes over my brain. Ideally, I break up my day in to 3-4 hour shifts. I go to the gym 3 days a week so I don’t become decrepit from sitting at my desk all day… otherwise I take a walk, go to a bookstore, or have lunch with my wife to break up the day.

We’re an old-fashioned, dinner-at-the-table family. So after dinner I goof around with the kids (6 and 3). We read books before bed. Then my wife and I get to chill out for a while. Unless there’s a deadline wreaking havoc with my mind, in which case I’m back out here till all hours.

(Wow, that was boring! I should’ve made up something juicy about volunteering with the SWAT team or wrestling alligators in my spare time.)

RH: Since you live in Florida, you’re one of a few copywriters who could actually write copy on the beach if you wanted. Do you ever write copy seaside? What do you most enjoy about living in Florida?

KR: My favorite Florida activity is wrestling alligators, Ryan… a lot of people don’t know that about me. It’s just a hobby, but I find it very empowering — and great exercise.

RH: You recently mentioned that copywriters who succeed tend to succeed very quickly. When did you first notice this pattern, and why do you think it works this way?

KR: This just hit me recently while talking with Chris Haddad. He and I started around the same time and he’s also come a long way in a short time. Same with Vin Montello, David Raybould and others I know.

That’s not to say you can’t make it work after a slow start, but there’s a certain combination of skills that the guys I mentioned bring to freelancing that make the difference.

The 3 biggest ones are:

  1. Sales experience.
  2. A passion for writing.
  3. Balls.

That 3rd one applies equally to several women as well, like Tina Lorenz and Lorrie Morgan-Ferrero. You have to know what you’re worth and demand your fee. If you can’t do that you’re in the wrong biz.

See… I learned this lesson the hard way with my comedy career. Back then I didn’t get the biz side of it. I was just thrilled to get paid enough to make the next gig. Getting paid anything to drink beer and tell jokes seemed like the crime of the century.

But my good friend, Billy Gardell (a very successful actor and comic) held out for headlining gigs way back in the day. He would go paint houses to make rent if he had to, but once he decided he was a headliner, there was no way he was taking anything less. And it paid off, quickly.

I didn’t have that level of confidence back then. Billy and I had parallel stand-up careers up until that point. Then he went on to a great acting career and I languished as a club act until I quit.

I don’t regret how it turned out, but it taught me a great lesson. You’ve got to learn to say “no.”

RH: Since you’re the team lead for a group of up-and-coming copywriters, I have to imagine a lot of copy crosses your desk. How do you spot a rookie vs. an experienced copywriter? What mistakes do you see over and over again?

KR: Another good question. I can usually spot a rookie in the headline. Actually, I shouldn’t say “rookie” because new writers can be very good out of the gate…

… I’ll say I can spot “a copywriter who isn’t doing their homework” by the headline…

… simply by this fact: a lazy writer’s headline tells me what they think I want to hear, while a diligent writer’s headline tells me what I need to know in order to keep reading.

Sometimes “lazy” writers just haven’t learned the difference yet. That’s why for the Stable we vet them through the SWS.

There are 17 steps in the Simple Writing System… “Headlines” is step 10. There’s a fair amount of “sales detective” work to be done before you can write your headline.

RH: What’s been your biggest challenge as a freelancer, and what have you done to overcome it?

KR: I guess I covered this in the earlier question about how I met Carlton. Feeling like I needed to incorporate every new tactic I came across was my biggest writing challenge.

Gary Bencivenga gave me a great goal. He said read one control ad a day and dissect what makes it work so well… then challenge yourself to add one thing that would make it even better.

I won’t pretend I do this every day. But when I read great copy, I take it apart and look for some way I could improve it. Looking for “even better” is a good mental habit to have in place when I write my own copy.

The other challenge was a couple of dry spells early on when I wasn’t sure where the next client was coming from. The money swings can be like a high-stakes poker game in that first year. But it evens out pretty quickly if you stick with it.

RH: If you were to add your two cents on “The State of Internet Marketing in Late 2009,” what would you say?

KR: That’s a broad topic. I think the “new media” will continue to find its way. Guys like Andrew Lock and Travis Miller & Jimmy Vee are doing really creative things with web video. It’s fresh and very effective for their businesses and their client’s businesses.

What people need to remember is the basics of salesmanship apply to any scenario. New mediums don’t reinvent the sales process, they just create new ways to deliver them.

I recommend freelancers study what top marketers are doing with video and learn to write scripts using the proven dynamics of direct response copywriting. There’s a growing demand for good sales video scripts.

RH: What is the best book you’ve read during the last 3 months? Why did you like it?

KR: I just finished I’m Dying Up Here: Heartbreak and High Times in Stand-up Comedy’s Golden Era. By William Knoedelseder. It’s all about the L.A. stand-up comedy scene in the mid-seventies, when an appearance on “The Tonight Show with Johnny Carson” could literally make you a star overnight.

You get to see guys like Letterman, Leno and Richard Pryor as club comics, plus all the drama that took place around the Comedy Store where so many legends got their start.

Really fun read if you like comedy. It was a refreshing change of pace from all the biz stuff I usually read.

My favorite book on writing in the last year was Writing Tools by Roy Peter Clark. Every writer should own that book.

RH: What one daily habit has contributed to your success more than any other?

KR: Learning when to STOP working. No kidding. And once again I have to credit Carlton for this. I used to pride myself on working 10-12 hours a day. John warned me that if I kept that pace I would eventually burn out. And there is no guarantee you’ll ever return from a true burnout.

I hadn’t considered that before. Ironically, when I forced myself to work less hours I got more done. It’s a theory you hear but can’t believe until you force yourself to do it.

RH: Where can people learn more about you?

KR: I think they just learned more than they ever wanted to know about me, but I do have a blog that I’m pretty proud of at The Copywriter’s Edge. I’d love if your readers joined my notification list. I’ve only promoted one thing in 2 years, so they won’t get pestered… but I’m not very structured in my postings, so that’s the best way to see new posts.

They can also look for more guest posts from me on John Carlton’s blog.

Also, I’ll be appearing every Tuesday night in December at the Biff Burger out on Highway 12. I share the bill with all you can eat Buffalo wings and speed metal karaoke. Hope to see you there!


If you enjoyed this interview with Kevin Rogers, you may also enjoy the interview he did with me. It’s less about copywriting and business… and includes a few personal details I haven’t shared before about my life and beliefs.

Check it out here: 12 Questions with Top Copywriter Ryan Healy

-Ryan M. Healy

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Ryan Healy

Ryan Healy is a freelance copywriter, list manager, and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like,, and

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