The Path to a Legendary Copywriting Career

John Carlton is a force of nature.

He’s that rare breed who can write fascinating copy, and is just as fascinating to listen to. Every story ends up a great story.

Through the lens of his remarkable journey to and through the copywriting trade, John delivers practical business tips and killer copywriting advice in this first half of a two-part interview I did with him.

Whether you’re a veteran writer, or just starting to learn your craft, the next 30 minutes with this outspoken ad man is a worthwhile spend …

In this episode we discuss:

  • How to go from slacker to pro
  • Why writer’s block is a myth, and how to get your work done
  • 4 books that will change your career (and you should read every year)
  • The dirty little secret most copywriters don’t want you to know
  • The mental attitude that made John’s career
  • 2 secrets of John’s success
  • A vital lesson on the nature of opportunity

Hit the flash player below to listen now:


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Please note that this transcript has been lightly edited for clarity and grammar.


Robert: You have found Internet Marketing for Smart People radio . I’m Robert Bruce. Today we’re getting back to basics with one of the most respected, dangerous and “been around the block” copywriters in the world. John Carlton is on the horn with me and I am going to grill him on your behalf and try to get every bit of copywriting wisdom that I can from the man. Mr. Carlton thanks for coming on the show today. It’s a pleasure to have you here.

John: It’s a pleasure to be here, I am looking forward to this.

Robert: Well before we get into these questions for you John, I want to remind those of you listening that this show is brought to you by the Internet Marketing for Smart People course which is our totally free, 20-part online marketing course, delivered straight to your inbox.

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If you want to get on the bus it’s easy, head over to , scroll down to about the middle of our home page, you’ll see the headline, “Grab out free 20-part internet marketing course,” drop your email address in the little box there and we’ll take care of the rest.

All right John. We could probably spend the entire show on just the story of how you came up as a copywriter, how you started, and then how you finally found your way, but give us the ten-minute version here if you can. This is a great story and I think it’s also very instructive to those out there listening who either want to learn this craft or want to get better at it.

How to go from slacker to pro

John: The reason it’s a good story is totally by accident of course, but I was the uber-slacker even before they invented the term slacker. I finished college, drifted away, and just really never figured out what I was going to do.

I was in my early 30’s, I think I was 32 maybe 33, and I had gone through a period of time where I was working in Silicon Valley in an art department and I lost my girlfriend, my place to live and my job all within a two-month period. I wound up living out of my car, going up and down the west coast looking up every friend I knew who had a couch to sleep on and sleeping on that couch.

I went down to San Diego and wound up in Los Angeles and got a really bad job and just had an epiphany that if my life was going to change, I was going to have to be the one who took responsibility and changed it. I learned for the first time in my life about goals, and goal setting and all this stuff happened and that’s stuff I could talk about a long time and I try to help people out with that, but as far as my story, literally I was working from nothing.

When I decided to become a freelance copywriter and go off into what I call, a career, which became a career, but I had no idea what was going to happen, I had no mentors, I had never meant a freelance copywriter before, I had no idea how I was going to pull all this off.

All I had was one month’s rent left in my bank account, I had a rattle trap car, that I had to put water in every time I wanted to drive it anywhere and I was working on a manual typewriter at the time, this was the early 80’s, before PCs came out. I had big cojones. I was living down in Los Angeles, happened to be a right period of time for freelancers, so it didn’t matter that I was figuring this out as I went along. Because there weren’t many freelancers out there.

The main thing that I did, the accidental thing that made my rags to riches story compelling was, I made what seems like an obvious decision. Back then, it wasn’t obvious at all, I figured out before I walked into a direct response advertising agency and said “I am here to be hired to write the stuff that your staff can’t handle right now” I better get really hip on everything about business, marketing, advertising, and stuff like that.

I took a speed-reading course, paid $100 for it, really couldn’t afford it, but did it. I went to the Torrance Municipal Library and read everything in the Dewey decimal system from I think 600 to 750, something like that. It was marketing, advertising, sales, salesmanship, all the stuff and I sped read through it and found the good books and took these good books and read them again very slowly.

What was interesting about that, there were two things that happened that gave me a leg up on everything? I then walked in to agencies thinking that that two or three weeks of having spent reading the entire library so of speak, was going to get me up to speed with the guys I would be begging for jobs from. In fact, it put me light years ahead of them.

I discovered right off the bat that most agencies, most writers and agencies, and most people who ran agencies knew very little about advertising marketing or business in general. They usually have jobs, they really wanted to be screenwriters or novel writers and they look down on copywriting and they thought being cute and clever was the way to go and they really had very little idea of what to do.

I walked in, the day I walked in as a rookie, I knew more than most of the people there just from an intellectual standpoint and as I gained experience, I kept running it through a couple of things that I invented, mostly the “gun to the head” attitude.

I just decided, every time I sat down to write a piece that I was going to write as if I had a gun to my head that would go off if it didn’t work. So that kept me from doing cute stuff, that kept me from going off on tangents, that kept me from experimenting, I used classy “how to” headlines. I kept it simple, straight forward and really stuck to classic salesmanship and all that worked.

The second thing that happened was when I met Jay Abraham, through Jay Abraham when I met Gary Halbert, who your listeners should know are now legendary copywriters, the books that I had found during my jaunt through the library and decided were the best ones, happened to be the ones that these guys had also chosen.

4 books that will change your copywriting career

This included Claude Hopkins, who was then out of print. The best book would be My Life in Advertising & Scientific Advertising two books that he wrote that were sold as one book is now back in print.

David Ogilvy’s books, Confessions of an Ad Man and a guy that worked with Ogilvy, John Caples, who wrote Tested Advertising Methods and also a guy name Victor Schwab, who wrote How to Write a Good Advertisement.

A lot of this stuff was written back in the 40’s, 50’s, and 60’s and in fact Claude Hopkins was writing back in the 1920’s, so this was the kind of stuff that was over looked, ignored and dismissed by most advertising, so called experts, back in the 80’s and we kept it alive. Like I said, a lot of the stuff, like the Robert Collier Letter Book had been out of print for 15 years.

When I was with Halbert, we paid a $1,000 for a copy of a mimeograph copy of that book. It’s now back in print and I think you can get it, I am not sure who is publishing it but you can get it for $12 now, but it was worth a $1,000 at the time to get a badly copied …. I don’t know if the listeners here know what a mimeograph is; it’s a very low-level form of copying.

The point is the information was most important. So all this stuff kind of coalesced. Now I spent my career working for agencies, for small corporations and then I got involved in the largest mailers in the world like Phillips and Boardroom and Rodale and things like that. When Halbert came along he kind of made me an offer, he represented the entrepreneurial side of the marketing world, and I didn’t even hesitate.

I turned my back on a million dollar career, I was “the” up and coming writer with these corporations and had a very, very lucrative career ahead of me and I was working with guys like Jim Rutz, I was ghostwriting for Jim Rutz, he’s the inventor of the magalog one of the top and highest paid writers.

I was working with Gary Bencivenga and guys like that, but I didn’t even hesitate to go off with Halbert and work with the entrepreneurs because that’s where it was exciting and that’s where we could try stuff, and we could market fearlessly and go where no marketer had gone before so I went off on that way. What happened was, while I was having fun and jumping on this stuff, two things are relevant and I will wrap up this story with this, one is, during my career and I would say it took me ten years to figure out how to be a good freelance copywriter before I took off with Halbert.

2 secrets of John’s success

I made almost every mistake possible, I stumbled into every pitfall, I went down to every blind alley, I did it, but I recovered quickly and I took notes.

Those notes, then became my first book, Kick Ass Copywriting Secrets of a Marketing Rebel , and became the foundation from my own teaching and my own abilities to take almost any writer and show them the ropes very quickly of what to do, because I knew what to do because I had done what “not” to do, figured it out, fixed it and then went back and did it right.

So I multiplied the successes, recognized, and minimized the bad stuff. It was kind of perfect. If I hadn’t taken notes, I would be a much less better teacher but I kept journals along the way, which I recommend all writers do. Keep a semi-secret journal. Actually, I would not want anybody to read my journals so I had an uncensored way of letting out all my frustrations and talking about things and I hope nobody finds these journals, but it helped me clear my head and stay focused on what was going on and fix a lot of problems that were happening. So I recommend journals for everybody. Well that’s great, I offered two things, I talked about one and the other one will remain a secret.

Robert: We’ll come back around to it if it comes back up. Why copywriting? In the very beginning where did the idea come from and what kind of captivated you or captured your imagination about it in the very beginning, when you were looking around, when you were living in your car, this rental trap car and you had a month, I think you said you had a month of income left or even that. Why was it copywriting?

John: There was a period of time, I sometimes compress the story because there is a lot of irrelevant stuff, but I did have a job. There was about a year and a half between that period of me living out of my car and me going out as a freelancer. During that time, I actually had a job where I was a one-man advertising department for a very small company and I was just trying things out. I stayed there because it was a forgettable job but when I went out on my own, yes, I had no money saved up, I had a car and I was working off of a typewriter that I had bartered for and I had a phone that I had actually taken out of the garbage at this other job that I had and set it up in my bedroom. I was in a little tiny apartment in Redondo Beach down in the LA area.

I had a bed and next to the bed was a desk and everything was there. There are photos of me back there, it’s pretty interesting, but it proved the point that that’s all you need is your brain and your skills and the ability to translate that into advertising.

Early I got a personal computer, I was an early adopter and I didn’t get a bigger office for five years or so, I continued working out of the bedroom because I just had my little cubby-hole. I did remember by the way Robert, not to scatter brain this too much, the other thing that I was going to say,

the main decision that I made when I became a freelancer, I just kind of announced to the world by just saying to myself — I am now a freelancer, that’s what I am going to do…

…and I had no plan B, and I was going to starve if I didn’t make this work, so it was kind of like Cortez burning his ships off the coast of Central America when he conquered the Aztecs.

Take your opportunities when they come

I realize that opportunities were not something that cascaded upon a person’s head. Opportunities are like whispers in the wind. If you are not primed to hear them, you will not hear them. I discovered Jay Abraham through someone else mentioning an ad that he had written somewhere and if I hadn’t had my antenna up and hyper attune to listening to that stuff … I didn’t know who Jay was, I didn’t know who Gary was, nobody did, Gary was actually still unknown when I was introduced to him.

These whispers in the wind, I think most people in their lives get at most two or three opportunities, big opportunities in life. Most people get none, even if some go by them or are available. What happens is that we not attuned to it, we get jaded about it, we think “oh if I don’t do it now, I’ll do it later” and what happened to me was not going to a Jimmy Hendrix concert back in 1968, I was still in high school, had an opportunity to go, didn’t go because something important popped up and Jimmy was gone not too long after that. I never did see him live and to this day, I can’t tell you what was so important that I didn’t go to that concert, but I do remember missing the concert.

That is that thing that opportunities come and go and there aren’t a lot of them and the big opportunities, the life changing and career changing opportunities often will not announce themselves, they will not tap you on the shoulder, they will drift by almost imperceptivity, you’ve got to be hyper attune to that. That alone can change a person’s life once they realize that opportunities are hard to catch and you need to jump on them right away.

Robert: Alright, one more thing from your story. You said that you went through the entire marketing and advertising section of the Torrance Public Library. This is fantastic, probably my favorite part of the story. You talked about coming out of that experience, reading those books that you thought would catch you up, but you found when you got out in the world that you were way ahead of working professional writers and copywriters.

One thing in particular from that is that you said that you read the stuff and tried to find the good stuff of course, but you reread the really good stuff. This is a drop dead simple, elementary piece of advice, deceptively to simple, but this is really important. Reading, re-reading, even a hand-full of books maybe on an annual basis.

John: Oh I would say, what’s interesting is that when I met Jay Abraham I actually physically met him, I had arrived at his office ready to punch him out because he had put an ad in the LA Times looking for direct response writers and I responded and he sent me back a curt letter which made it obvious to me that he had not read my stuff, because he had said “You are not really ready for this kind of stuff, why don’t you read Claude Hopkins and I suggest that you read it six times before you get back to me.”

Well I had actually read Claude Hopkins, My Life in Advertising & Scientific Advertising , eight times at that point. That was during the first year and a half of my so-called career. So I was very angry because it was obvious that he had not even looked at the package, that he had just taken my response and sent me this form letter back. So I found out that he lived very nearby and I went and met him and his office manager intercepted me, I was going to go in to confront him, but I was really mad because this was my life and he was being capricious about it and I wound up becoming fast friends and made a deal with Jay, this is very important too, and ties in with that reading the books.

When he found out that we had the same books in common, that I had read a lot of them, we were reading these and I continued to read that book yearly for another 15 years, I haven’t read it in the last couple years, but I am due to read it again. I kept reading these books but I also made a deal with Jay that I would work for free in exchange for free run of his office, so I got to hang out while he was doing consultations, I got to look in the back drawers of forgotten cabinets where stacks of unpublished advertising was hidden away and I got to see how a successful consultant ran his operation, so it was huge.

The mental attitude that made John’s career

I wasn’t getting paid for it. I would write for free, but it was a million dollar education. Finding those old books that other people dismissed and ignored, setting myself up for not becoming rich right away but actually doing my due diligence. I grew up in a working class household. My father was a construction worker and they don’t do it anymore but they use to have a guild, you had to be a novice, you had to be mentored by someone else who knew how to do the job and it took a couple of years to get from novice state to journeyman and then after journeyman you became a foreman and such but you had to climb the ladder very slowly.

So that was beaten into me and I didn’t expect, even when I knew I could write better and knew more than a lot of these ad guys, I knew that until I got the experience, and until I had done my duties as a rookie, that I wouldn’t be deserving of calling myself an expert writer yet, so I was willing to do this. I didn’t have expectations of fast wealth, I had expectations of entering a career that I could do for the rest of my life.

I have to tell you too Robert, that career, I teach other people how to be writers and how to be freelancers, because the career saved my life and I made a vow early on that I would help others if I made it. I mean I seriously had no plan B, I was working without a net, it was pretty scary so I understand how scary it can be for others and I started confronting things. That attitude, that “gun to the head” attitude, I started confronting things like writer’s block and things like that and realizing that they were myths.

Really, being a good writer meant that you didn’t have a novel … I do write novels on the side, but I didn’t consider myself a novel writer, moonlighting or trying to pay the bills by being a copywriter. I was a copywriter and on the side I might sample in fiction and do other things, but I took this business of creating ads very seriously and I never forgot that when I wrote an ad for somebody, his business was on the line, his lifestyle, his family, everything that he needed to make his business a success, copy was king from the very beginning, so without a good ad, they are nothing. Businesses are toast!

I realized that even if I wasn’t getting paid or even respected as much as I should, I held the keys to the kingdom for every single job that I took. If the ad didn’t work, bad things were going to happen to the client’s business. Also it formed my attitude later as my fees went up and as I started gaining notoriety and “reputation,” I started realizing that I had to take control, that I had to be and actually I think, we’ll get into this later on, but it’s about doing freelancing in the right way and having the right attitude and I think a lot of people get into it thinking mostly this is about you making money as a writer and that’s fun for people who realize “wow I am a professional writer this is great!”

That’s a huge revelation to have that you are actually paying the bills by being a writer, but sitting down and crafting language so that it effectively communicates a business sales message to prospects. That’s all very fun but really you are the savior of businesses, you are the guy that is going to come in and take an untenable position of a business. They’re almost always struggling when they have freelancers. They don’t know how to write, they don’t understand advertising and they don’t understand salesmanship and print, they don’t understand any of this stuff and you are that guy that comes in.

You are the white knight. So that attitude means that you have to be serious about this, it’s your job, and your job is very important.

Robert: Alright, you talked about goals, you talked about writer’s block, worth ethics, let’s extend this idea of what your job is and take a look, maybe a day in the life kind of thing. What are your working habits John, and how do you approach the blank page and how are you getting your work done day after day and year after year?

Why writer’s block is a myth and how to get you work done

John: That’s a great question and I will say that as a tie-in to me being a slacker who didn’t get my act together until my early 30’s and I had a true rags to riches story. Actually living in my car and then breaking out from that, so too am I one of the laziest writers that you will ever meet. I am by nature a slumbering ape in the jungle who is waiting for the banana to fall on my lap because I am too lazy to get up and go grab it.

But when I write, I do something that I call “stocking the desk” and what happens is that I know that I am going to spend a period of time and it could be an hour or two hours or whatever but I am going to go deep into this writerly state and so I stock the desk. And when I have to write an ad, I will do what I need to do, maybe I have to take a walk before hand, maybe I’ll take a nap, maybe I’ll take a long hot shower, I will do what I need to do and I’ll start to get prepped and if I don’t need to get prepped at the desk, if I can get on the phone, say an interview with somebody, and just get some information, I won’t sit at the desk and do it, I’ll walk around the house or I’ll walk out back.

What I am doing is prepping myself, and when I get in close to my desk, my desk by the way looks like a bomb went off, I use pile theory here. People would be appalled by the mess on my desk right now but I know where everything is and there is a method to my madness but I work very sloppily, I am very lazy but when I sit down and I am ready to write, I become the most intensely focused, hard-working writer that I’ve ever met in my life. What I do is I get prepped, I get zeroed in, I stock the desk and when I am ready to go, it’s like “bang” let’s go!

I am a fighter stepping into the ring. I’ve mentioned before that writer’s block was a myth, when I speak in front of audiences and there are usually a number of writers in the audience, or even there’s people who are sampling writers or need to write and say “how many people are bothered by writers block?” and a good third to a half of the room will raise their hands and I disabuse them of the notion, my response is “grow up it’s a myth, it’s nonsense.”

All writer’s block is, is not being prepared on what you need to do.

So if you sit down and haven’t got a headline burning in your head and you don’t know how you are going to start this conversation using language to write down whether it’s going to eventually be a sales video or a presentation from the stage or whether it’s going to be an infomercial, whether it’s going to be a written ad in a magazine or it’s going to be a website, it doesn’t matter. It starts with a written page, writing down “Hi my name is Joe Blow and for the last twenty years I’ve been an expert in blah, blah, and here is what I have for you.”

If you are not ready to just blast that first draft out when you are sitting down, then you have no business sitting down and even starting because you should be prepared. You should be boiling with the information that you need and all the stuff. Freelancers become experts in the markets that they inhabit for the period of time that they are paid to inhabit that market, so that’s what makes us different from other writers.

Some writers only work in one market, like they get a job … say a guy in the weight loss or diet field and they wind up becoming an expert in that, but they couldn’t write for the financial industry to save their lives, they would have to reinvent it. The kind of freelancer that I was, was that I took every job that came along and I don’t think there was a market out there that I haven’t written for. I knew a little bit about a lot of different things, but for the period of time that I am writing a piece I become an expert. I do what I have to do. I do a shorter version the equivalent of reading everything in the Torrance Municipal Library of that, I know how to interview people now and get the short cuts on what’s going on.

The dirty little secret most copywriters don’t want you to know

When I interview to write for a client, in a perfect world I interview the client yes, but I don’t take what he says, the boss of the company or the guy behind the product as seriously as I do when I want to talk to his secretary, I want to talk to the guy who actually has to sell the thing, I want to talk to the feet in the street, I want to talk to the chemist if they are involved, I there is anybody else involved, I want to hear the rumors, I want to hear what his staff is saying behind his back about him. I want to hear from the people who actually have to deal with the people on the phone who are maybe doing the refunding, I want to hear all these stories.

Hidden within that are the hooks and the real reasons why people buy and why the product can be successful, which often the owner of the company is clueless about because he has his own myth going on. He is in this echo chamber where he believes his product is really great and it’s his baby and people buy it because they want “X”. Usually that’s not true. Usually people are buying it for a totally different reason.

That is why when I present … and I don’t take on very many clients anymore, in fact I turn down 99% of people who want me to write for them and I recommend other writers to them, I make sure that they are taken care of but I am not taking the jobs, but when a client does hire me and I present a piece to them, if he says “wow this is a great ad John, I can’t wait to run it” then I know I did something wrong.

The only way I know that I did something right is when I present him an ad that makes him nervous. I want him to come back and say, “We can’t run this! We can’t say this! This is going to blow everything up! This is horrific!” because then I knows I’ve gotten him out of his comfort zone, into that space where the ad is going to wake people up and actually get the results that he has been looking for.

Most people want pabulum out there, they are afraid of their “reputation” and they want to run ads that are mild and don’t offend anybody, they are more worried about offending people then they are about selling stuff. If you are going to sell stuff, if you are going to be aggressive about having a great ad running, you are going to get some blow back; you are going to get a certain amount of refunds.

I tell people if you are marketing and you don’t have that sweet spot of refunds; between 7% and 15% of all sales should come back as refunds. If they are not, you are not pushing hard enough because to wake people up to get them to understand your message, to get them involved in the capitalistic dance of buying and consuming and getting whatever it is, whether it’s services or products or information, whatever you’ve got to sell.

It’s a dance and 15% of the population, I have a psychology degree Robert, we’ve talked about that, 15% of the population is crazy. So if you are not bringing in enough of any given audience of the 7% refund rate that you have, you can’t take that personally, that’s going to be people who bought by accident, who were drunk and bought, who bought and where in sycophantic episode and have no memory of it and things.

You just have to keep that in mind so that you don’t take that personally, but you have to be … I hear people bragging about zero refund rates, you are just marketing inside a small pocket and if you are happy with that then great, but if you want to break out of that and really start making some waves in your niche or your industry then you’ve got to get out of your comfort zone.

Robert: Hey everybody, Robert Bruce here closing out of part one of this interview with John Carlton, we’ll be back next week with part two. If you want to get more of John in the meantime, you can find him at and if you like what’s going on with this show, the best way to support it as always is to head over to iTunes and drop a comment there or a rating if you do so, we really appreciate it. All right, we’ll see you next week for part two of this interview with John Carlton.


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About the Author: Robert Bruce is Copyblogger Media’s Chief Copywriter and Resident Recluse.