Copywriting Genius: Issue #64
Find Out Why This Master Copywriter Says,
“These are the Three Best Ways to
Perfect Your Copywriting Skills…”

Leon: I was an adjunct lecturer in English at Queens College of the City University of New York. Basically it was teaching freshman composition and supervising the College’s writing workshop which assisted students after classes.

CG: Did you know what copywriting or direct mail was before you became a copywriter?

Leon: Yes, I did. At a certain point, I knew I would be leaving teaching. I did a systematic review of my talents and abilities and what jobs suited me. Copywriting seemed to be it, so I took a look at what was available.

CG: Wow! That’s a good way to approach copywriting. Most of the copywriters we interview usually stumble into copywriting. Not many realize they could have a career as a copywriter. So tell us how you become a copywriter.

Leon: While I was teaching, I investigated copywriting possibilities. As an adjunct lecturer, I only taught a couple of days a week, so I had time to try my hand at copywriting. A friend knew the promotion director at Times Mirror Book Clubs. I put together some spec samples and got a number of assignments writing direct mail for their book clubs: Nature Book Club, Outdoor life, History, etc.

At that time, I also wrote a long article that was featured in the Sunday New York Times – the article, along with Times Mirror samples and some more specs, got me my first job as a copywriter at Wunderman (at the time, it was called Wunderman Ricotta Kline), the largest direct marketing agency at the time. I was first interviewed by Lester Wunderman, who was the chairman or chairman emeritus at the time. After my interview, he sent me to interview with various creative directors, and I got the job as copywriter.

CG: That’s really neat … that the article helped you get your first job as a copywriter. So at the agency, did someone help you? Did you have a mentor?

Leon: My beginning was pretty much working at ad agencies. You worked with copy supervisors and group creative directors. There were so many, so I can’t point to any particular person – just an accumulation of supervisors who worked with you. Your copy was constantly being reviewed and critiqued. And you had to rewrite in order to get approval. Then of course, there was editing after client comments. So it was constant on-the-job learning. You were constantly creating concepts, writing drafts, having them reviewed, then you rewrote and edited. You learn a lot in that process. There’s a lot at stake, so you really absorb and internalize the lessons.

Also, at that time, Wunderman and its parent agency, Young & Rubicam, where I worked after Wunderman, had formal training programs. We’d go to various workshops in the morning. Workshops on creative strategy, strategic thinking, copywriting, etc. So, overall, the agency experience provided a great deal of training. I don’t think they have the resources or the profits to do that these days.

Throughout I also had a subscription to Who’s Mailing What, and studied the packages very closely. In particular, I followed and studied the work of Bill Jayme. I thought his work was truly brilliant. He was the one who saw how to use every element of the direct mail package. I think it is also relevant that he worked so closely as a team with his art director for years and years.

CG: I forgot to ask this earlier, but how long have you been writing copy?

Leon: 27 years.

Top Notch Agencies and Gangbuster Results
CG: Do you remember the first project you worked on as a copywriter?

Leon: It was a package for Times Mirror Book Clubs. I believe it was for their Nature Book Club. At the time, the main element in the package was a large fold-out piece, which unfolded like a map. It acted as their brochure. For instance, one section on the Nature Club fold-out might be a beautiful illustration of a bird with some interesting facts about that bird. You might say it was a way to present all sorts of fascinations in a graphic and engaging way.

CG: What about the first success you had as a copywriter? Do you remember what that was?

Leon: I believe my first official success was when one of my packages I wrote for Times Mirror – for their Outdoor Life Club – beat the control. But the first big success was when I was writing on the Time magazine account. I wrote a print campaign that lasted for years, and also worked on their successful direct marketing TV campaign.

CG: Is there one project that stands out as your favorite?

Leon: Yes, it was for San Francisco Federal Savings – I think they’ve since been acquired or merged. The package was a promotion for some kind of bank membership club. I forget exactly what you got with membership, but it included a nice increase in CD rates plus various bonuses. It was meant to convey a sense of exclusiveness for San Franciscans.

At the time, there was an iconic newspaper columnist in San Francisco named Herb Caen. His column was an interesting mix: part local gossip of the San Francisco area – who was seen at various nightclubs, etc. – and part celebration of the SF Bay area, and how wonderful it was to live there. Since the bank’s Club membership was supposed to convey a sense of insider status in the San Francisco Bay area, I thought nothing said that better than Herb Caen.

So one of the concepts I proposed was to have the mailing come from Herb Caen.

The idea was to imbue a boring bank membership with some of Herb Caen’s panache and excitement. Instead of a brochure I proposed we have a long column in Herb Caen’s format, and I would write the column in his style. His style was known as 3 dot journalism. He would offer a tidbit of gossip, followed by three dots, then another tidbit, and so on. So for the promotion I tried to think up juicy things that people could do with the club membership and the money they got from the rate increase. Each item was separated by the three dots.

While I really liked the idea, I thought it was one of those longshot concepts. Either the client or Herb Caen would nix it. Well it turned out they all liked it. Caen just wanted final approval.

It was a lot of fun to write, turning CD rates and other banking items into tidbits of gossip. And Caen approved it without any changes.

It turned out to be one of those wonderful trifectas, where the client loves it, you love it, and the results are gangbuster. And for a moment, you think all’s right with the world.

CG: Such a great story. Thanks for sharing it. You talked about working for agencies, but let me switch gears here for a minute. As a freelancer, how do you drum up clients?

Leon: Well, a number come to me through referrals from current and former clients and art directors I’ve worked with in the past. A number come to me because they’ve found me on the Internet.

As far as drumming up clients … I periodically send out direct mailers to select target audiences. The mailer includes a flyer with a concept that demonstrates a good direct marketing approach. Usually something fairly simple, so I can just call on an art director friend to polish the design. The flyer and the letter have my phone number and also direct the reader to a webpage where I have samples and other information about my services.

CG: Sorry about jumping around here, but our readers would be curious to know … What do you like most about copywriting?

Leon: I’d say it’s a combination of 3 things. There is a certain satisfaction in craftsmanship. It is a craft. And when you feel like you’ve crafted together a really effective marketing piece from concept to finished copy, there is satisfaction in that. Of course it’s much better if the piece does well and beats the control. That isn’t always the case. But you can always feel you’ve done your best and crafted a piece of marketing communications that has everything in place, hits all the hot buttons, flows well, etc.

Also I find satisfaction in helping people grow their business. This is particularly true when some sort of kinship is established between me and the client. I believe my copy is an important part of the success of their business, and when you get to know and like the client, that is very rewarding.

The other thing – at least it’s true with freelance writing – is the freedom to work on your own. At home – with control over when you work.

CG: We talked earlier about some of your successes. Now let me ask you this: What one thing did you learn (or take away) from a package you wrote that didn’t work as well as you had expected or hoped?

Leon: I remember a piece I thought would do well. It had a really good, unique idea. The story was well told. It did okay, better than average but not great. When I rewrote it and took an approach that was more in your gut, something that leveraged current events more forcefully, a more controversial approach, it did better. It told me that it takes more than a good idea to get the best response. You have to find the idea that hits the audience in a more emotional, visceral way.

CG: Was there a moment in your career where you knew you had made – or could make – good money writing copy?

Leon: I’d say it took a couple of moments. After I worked as a successful copywriter in the ad agency world for a good many years, I had to prove myself as a freelancer.

I got a project working on subscriptions for a computer magazine. At that time, new computer magazines were springing up every day. This was a technology magazine that was part of a larger group of magazines. They hired me essentially to act as their creative agency. I hired the art designer and we worked together to produce a very successful package. Once that made it, I knew I would continue to get projects from the other magazines in the group.

Then, when I moved back to New York after a number of years in California, I had to prove myself again. I got a project to create a multi-step direct mail package for IBM. It beat the control many times over and was written up as a case study in a direct marketing textbook. Once I saw it in the textbook, I was pretty sure I could make good money based here in New York.

Tell Us About Your Methodology …
CG: Now let’s get into the nitty-gritty of your methodology. What’s the first thing you do when you get an assignment?

Leon: The first thing is to research the subject matter. I do a lot of research on the web – competitors, articles, reports, forums, Amazon.com. I want to know characteristics of the list. If I’m promoting a newsletter I want to see as many previous newsletters as I can. I ask to speak to company executives and others who might be helpful, whether it is an editor or a marketing director.

Once I get a grasp of the subject, I start thinking of a first round of ideas and concepts. I tend to do this before looking at old controls. By doing this, I’m not influenced by what people did before me. Then, after I have a first round of ideas, I analyze previous controls and other promotions, and try to assess why the control worked and why others didn’t.

CG: What do you need the client to supply you with?

Leon: A project brief. If they don’t have it, I ask them some questions so I can create one: Who is the target audience, what is the main benefit, what is the unique selling or value proposition, what is the main problem the product or service addresses, etc. Any previous samples, previous controls, competitive pieces, relevant websites, testimonials and case studies, access to interview key people.

CG: Has a client every supplied you with too much information … enough that it bogged the project down or was too overwhelming?

Leon: Yes, that does happen. When it does, I have to make a conscious effort to decide what is needed and what is just weighing me down. In some cases this weeding out process is helpful, because as you’re eliminating or accepting material, you’re refining your thought process about the promotion. But sometimes weeding out overload is just time consuming.

CG: How do you get to know the target audience?

Leon: In some cases where I’ve worked in the arena for a long time, I know a great deal about the target audience already. For example, the investor audience. Other times, I try to assess as soon as possible what is the main problem or pain of the target audience that the product or service should solve or address. Once I get a good fix on the problem, I try to get as much demographic and psychographic information as I can. Age, gender, lifestyle, attitudes, income, etc.

I read websites that relate to the product. I’ll also see if there are any online forums related to the product and read them. It’s a good way to find out the problems your target audience is having … what gets them agitated. You also get a peek into the specific language and buzzwords they use. I’ll read any testimonials and case studies the client has. I check out Amazon and see what books in that market are popular. I read the reviews, pro and con. I’ll also check out related magazines, trade journals, and articles. Just the titles alone of articles can be very revealing.

Truly Understanding Your Target Audience
CG: What about the concept of the package? How do you come up with the theme or idea for the promotion?

Leon: It certainly starts with research on the target audience. It’s important to understand what their main problem is, what they really want. Not only the rational problem and benefits they are seeking, but also the underlying emotions. Is it fear, or anxiety, do they feel they are missing out on something? Are they confused about an issue? Are they seeking simplicity? Get all the rational and emotional benefits.

I try to refine the emotion at the heart of the matter. For instance, is it really wealth the audience seeks, or a sense of security? Once I feel I have a grasp on that, an understanding of the market, and a unique selling proposition, that’s when I’ll go off and work on themes or ideas for the promotion. I want the theme to be based on the target market and the unique selling proposition.

If I’m working on my own, and not with an art director, I’ll go to a café with a notepad and just start thinking of ideas. Since I live near Central Park, I’ll walk around the park and mull over ideas. Generally what happens is, once I’m thinking of concepts for an assignment, it’s hard to turn my mind off, so I’m thinking about it all the time.

Working on themes and ideas is one of my favorite parts of the work, so I really get into it. I try many different angles, each aimed at illustrating the unique selling proposition. There may be a single detail or fact that can be expanded. For instance, in the China promotion, I was reading quotes by Chinese officials about how important the upcoming Olympics were to them. There was building frenzy to make sure they made a good impression on foreign visitors. So it occurred to me that, not only were certain companies benefiting greatly from the pressure to build now, but the fact that the Olympics were upcoming lent itself to the idea of an inherent deadline: If you want to invest in these companies, do it now, while they are benefiting from the build up to the Olympics.

I try lots of different ideas, and then I narrow it down to about 2 or 3. If I feel I could go with any of them, I present them to the client, and get feedback. Then we’ll talk about it.

CG: Do you develop the headline first or start with the body copy?

Leon: It depends. I always start with the concept and theme first. Then if it’s a standard direct mail package I’ll begin working on the body of the letter first. When I’m working on the brochure or booklet part of the package, I’ll begin by working on headlines.

Why the difference? I think people will glance at headlines of brochures first and decide if they want to read it. With a letter, while the headline or Johnson Box is important, I think it’s the first few lines of the letter that determines whether the person will continue to read it.

With an online promotion, let’s say an email sales letter, I start with headlines. I think with email and other online promotions, the subject line and the header are even more critical. You must grab the reader’s attention and interest or they won’t scroll down. You’ve got to hook them in very quickly. I’m not trying to hone the headlines yet, just trying to get a bunch of possibilities that I can attach to specific themes and ideas.

During the course of writing the copy I’ll keep revising the headline. Sometimes the direction the copy takes can dictate some dramatic changes in the headline. Sometimes the best headline is buried in the body copy or in a subhead – you just have to recognize it.

CG: After you finish a draft, do you let it rest for a day or so and then re-read and make edits?

Leon: Oh, yes, I think that is necessary. Let it rest. Come back to it with fresh eyes. Copy almost always improves when you come back to it after letting it sit for a bit.

CG: Do you ever show your copy to another copywriter for comments and suggestions?

Leon: Sometimes, when I know a copywriter friend is around. Sometimes I’ll show it to a non-copywriter – somebody who may be representative of the target audience – so I get more of a sense of the typical reaction from people who might be receiving the promotion.

From Financial Products to Silicon Valley
CG: I know you have a varied background. But do you specialize in writing for certain products? If so, which ones?

Leon: I won’t say I specialize in certain areas, but there a few areas where I have extensive experience, and most of the work falls in those areas.

For instance, I’ve done financial services for most of my career. In fact, at one point, when I was writing copy for an investment magazine for many years, I actually went ahead and earned a stockbroker’s license. I wasn’t really going to be a stockbroker – but I found it interesting … and it definitely separated me from the pack. For example, when Barclays was introducing iShares, the agency handling the account told me the fact that I had a broker’s license was one of the reasons they picked me to write for the account.

For a number of years I worked extensively with pharmaceutical ad agencies. This meant learning referencing and annotating – it’s almost a scholarly type of work, where every claim has to have acceptable attribution – be it a recognized journal or clinical study. Having this kind of expertise has brought me a good deal of healthcare work

When I was working in the San Francisco Bay area, right near Silicon Valley, I would get a lot of technology assignments – software, hardware, publications, etc. Right now, there seems to be an upswing in tech clients.

So it varies, depending on the business cycle. When certain industries are doing well, I get a lot of assignments in those industries. Right now, no matter what the industry is, I get a lot of Internet-related work.

CG: How would you characterize your style of writing?

Leon: I think it’s strong on concept and theme. It tends to be conversational, but that varies to a degree, depending on the audience. I try to get a good picture in my head of the ideal target audience. One person. Whether it’s an investor, someone suffering from arthritis, whatever. I keep that person in my mind as I write. And because I read my copy over and over out loud as I’m revising, I imagine reading it to the person I have in my mind.

CG: Do you make suggestions on what things the client could test on your package?

Leon: I do. Generally, themes, headlines and lead paragraphs. It can be a progression. For instance, first testing different headlines and leads with the same theme. Then switching to testing new themes and different headlines within the new theme.

As far as the offer is concerned, usually the pricing is set, but I often suggest different bonuses. For instance, special reports that may relate to the promotion’s theme.

CG: How involved are you in the design?

Leon: I’m often very involved. I worked with agencies for many years where you generally work with an art director. I really enjoy working with art directors and have a very healthy respect for the power of design to affect response.

When I’m asked to choose my own art director, I first try to see if one of the art directors I’ve worked with in the past is available. If the client has its own design staff, I often do very rough drawings to indicate graphics or layout.

CG: How long did it take you to complete this project?

Leon: This one took about 2 weeks. I was also working on other projects at the same time, so it wasn’t 2 weeks solely on that project. But that’s about how long it took from start to finish.

CG: If you could divide you work up in parts, how much time do you devote to research, to writing, to editing?

Leon: This can vary. Also, there isn’t a strict demarcation between them. While I may start with research, sometimes – in the middle of writing copy – I realize that more research in a particular area is needed. And as I write, I also do a fair amount of editing before I have a first draft. If you include concepting and brainstorming as part of writing, it’s something like this: 30% research, 35% writing, 35% editing

As this indicates, I spend a great deal of time of time editing and rewriting. I think a copywriter is like a sculptor. The sculptor has a rough slab and he is constantly whittling, scraping, refining until the piece is finished. My copywriting process is something like that.

CG: How do you figure out all the benefits a product offers? Do you list them out, do you talk with the client, do you use the product yourself?

Leon: I’ll ask the client, research the product, use the product if possible, study and analyze the target audience, look at testimonials and case studies. I’ll try to see if anything has been overlooked – or if there is a benefit that is not obvious but is maybe an emotion that was not considered at first.

CG: Do you think there is a difference between online prospects and direct mail prospects?

Leon: It depends. If it’s a promotion mailed to a certain list vs. a promotion emailed to a similar list, the messaging and the writing can also be quite similar.

But if, let’s say, it’s a promotion mailed to a list vs. a landing page people come to from a pay per click ad, then there is a bigger difference. The person who arrives at the landing page has actively searched using specific keywords for a topic or problem. When they click on the ad they want to see a pretty specific message. The landing page needs to be very aligned with the keywords and ads in the pay-per-click campaign. You need to write with that in mind. With the direct mail, you don’t have to align your writing so closely to specific keywords.

Special Tips and Techniques
CG: Do you have any special tips or techniques for boosting response?

Leon: It’s important to inject a credible sense of urgency to boost response. Once the reader puts it aside, the possibility of a response plummets. If the urgency is tied to an offer with a deadline or a limited quantity, try to give a reason for the deadline or the limitation. Make it as real and credible as possible. If it’s possible, I also try to find a deadline that is organic to the promotion. Like the Olympics I mentioned for the China stock promotion. The urgency to get into these stocks before the upcoming Olympics was inherent in the promotion.

I like to use graphics to heighten a sense of urgency. In direct mail I like deadlines and calls to action to not only be in the copy but also attached to graphics, such as boxes, callouts, etc. Make it stand out.

On the web, you now have great multimedia tools such as audio and video to heighten urgency.

CG: Is there a special thing you do to come up with headlines for your projects?

Leon: Well, one thing is to write a lot of them. But not just wordsmithing variations. I look at whole different approaches and categories of headlines before wordsmithing.

For instance I might look at some benefit-heavy headlines. Then I might try headlines that approach it from a more emotional point of view. Then problem-solution, etc. So I try to make sure I have a bunch of very different directions before I really get into wordsmithing the different headlines.

Also before wordsmithing, I’ll use a pen and pad and get into a relaxed atmosphere – whether it’s my couch or a nearby café. Once I start refining the wording, I’ll work on the computer.

CG: Is there ONE thing that every package you write always has?

Leon: A central idea. In other words, not just an offer or sending an announcement that the client thinks is important. The idea could be a story, a unique marketing angle or offer, a new solution to a problem. It gives the mailing or webpage a reason for being. People see all sorts of announcements and offers. A central idea or theme strikes a deeper chord and sets it apart.

How to Build Credibility for the Product
CG: How do you build credibility for the product?

Leon: I look to incorporate as many credibility indicators as possible: awards, certifications, testimonials, case studies. Certain names or brands, depending on the industry, can offer credibility. In the health field, it can be a study from Harvard Medical School or Johns Hopkins. If the promotion is technology-related, any connection to a Google or an IBM, or a company like that, will carry a lot of weight. Certain investment firms and analysts carry a lot of weight in the financial field. Track records and biographies can be particularly effective in certain categories.

While testimonials are effective, I think testimonials integrated within case studies are even more effective. I call them case stories. This way the quotes have context. You know the situation and how a problem was solved.

CG: How do you stay in touch with the marketplace?

Leon: I read tons of magazines and newsletters. The NY Times, NY Post, INC, Business 2.0, Forbes, etc. Websites such as popurl and digg not only tell you what people are reading but how popular articles are in different industries or sectors. Home pages of Yahoo and MSN are not only good for keeping up with what’s happening, but it’s also worthwhile to study their headlines.

About Your Current Control
CG: Now let’s talk about your current control. I know readers will want to know more about it. Can you describe the target audience to us …. their concerns, etc.?

Leon: The target audience for Growth Report, an investment newsletter focusing on growth stocks, is self-directed, individual investors primarily trading through online brokerage accounts. Major concerns are inflation, US stocks, discovering opportunities in China-based stocks trading on US exchanges.

CG: So what is the core emotion in this package?

Leon: On one hand you, could say that almost all investment pitches appeal to the desire to make more money. But I think there is an underlying emotion that is an offshoot of that. The fear of missing out on a big opportunity – at least that is the core emotion I used in this instance.

In many cases, I think the fear of missing out triggers a stronger call to action than the desire to take advantage of an opportunity. I know they sound about the same. But there is a psychological difference, and that difference is reflected at various points in the copy. Of course, you have to make the opportunity big enough and credible in order to make the fear of missing out effective.

CG: You do a nice job of teasing about the stocks in the report. Is that original copy of your own, or did the material come from the report?

Leon: The copy is definitely my own. I read the report and incorporated any relevant data and insight about the stocks that are in the report. But I also did a lot of research on my own about each stock I chose to write about. The fact is, I needed to do initial research in order to select the juiciest stocks in the report to write about.

I go to Yahoo Finance and other investment portals to see what’s there – do a Google search on the stocks and the industries they’re in, and of course, look at their websites. I’m pretty through on doing additional research. The research often yields additional nuggets. Even if it’s just one piece of data that I can build a story around, it’s worth the time.

CG: Speaking of the report, how involved were you in the concept of the free reports or were they part of the control?

Leon: In this case, they had already created the report. The control piece used a similar China report, although the stocks were different. How I used the free report was up to me – whether the letter would focus on the report or the newsletter, which stocks to highlight, how many stocks to use in the tease, etc.

CG: Your description of the newsletter is great … “more like a special, highly focused membership club …” How did you come up with that copy?

Leon: I think the idea of a being a member of a special club is more desirable than just a subscription. Of course, you need to be able to justify calling it a membership. And I believe the added features and benefits subscribers to Growth Report get with the website – such as updates and 24/7 access – justifies the larger claim of a membership. Whenever possible, I look to stimulate the idea of being part of something special, appealing to the desire to be an insider. It’s not just added value – it’s added emotional value.

CG: Why do you think this package worked so well?

Leon: I’d point to a number of factors:

Highlighting the incredible growth rate of one of the companies in the headline not just drew people in, but set up the possibility of a big investment opportunity.
Creating a framework of organic urgency. What I mean by that is, I stated that much of the furious growth in China is being stimulated by the rush to prepare for the Olympics.
It was all part of a central underlying image I tried to convey: China feverishly building and growing. The statistic about China’s infrastructure growth equaling the size of the city Houston every month – and using a photo of Houston to emphasize the point – all added to this image of feverish growth. And by implying that it was all hurtling toward this one day, this global deadline – the opening of the Olympics – fed the urgency to find out about these stocks now.

I tried to integrate each stock tease into the thought that certain stocks were riding the wave of China’s hyper growth – and you shouldn’t wait to find out what these stocks are.

CG: The tone you use in the copy is very conversational and easy to read. Would you say that is one of your trademarks?

Leon: Yes. And this brings up an interesting topic to me – tone and voice. I haven’t seen enough talk about it in copywriting articles and books. And I think it is critical.

I try to be appropriately conversational. It depends on the industry and the venue. In the investment newsletter world I think a conversational, slightly wise-guy approach works well.

For a number of years, when I was working with an institutional investing magazine, I was fairly heavily involved with investment analysts. At that time, I noticed that a few star analysts, for instance Mary Meeker, an analyst at Morgan Stanley, wrote research reports that were highly evocative and conversational. Something you wouldn’t expect from high-end analytical research. But the fact is, they were the most popular analysts. In a sense, I saw it as a green light to be just as conversational and evocative in my marketing copy for the industry.

I’ll tell you something interesting on the topic of tone and voice. A number of years ago I was also writing a bunch of annual reports. It was well-paying work that kept coming my way. But I noticed that, as I was adopting the kind of corporate tone and language that fit that venue, I was losing, or feared that I might lose, the conversational tone I liked for my marketing projects. So, at a certain point, I turned down all annual report work and stuck to marketing.

CG: Can you share with us results – such as gross revenue, response rate? Any statistics you can share is greatly appreciated.

Leon: According to the marketing director for Business Financial Publishing, the parent company to Growth Report, my sales letter did

89% better than the previous control piece on China
444% better than our initial China control piece
CG: Fantastic results. Thanks for sharing. Now for a few fun questions.

A Few Fun Questions …
CG: What’s it like to work with you on a project?

Leon: I like to think I’m pretty easy and flexible to work with. I think it’s important to meet deadlines, so I do. I try to get buy-in at key points. This helps avoid misunderstandings, etc. For instance, I like to get buy-in on a concept before proceeding with the writing. I want the client to have a pretty clear idea of what direction I want to go in and what to expect, so we’re all on the same page, so to speak.

CG: If you could choose another career besides copywriting, what would that be and why?

Leon: Well, actually, I am already working in that other career. Internet entrepreneur. I market a number of information products online. It’s not only a nice income generator, it also keeps me on top of what methods are working best, what’s getting the best response, etc. So it also helps me in my copywriting work with clients. I find the Internet extremely interesting. For instance I believe the Internet has been crucial to the rise of Barack Obama. It really was his spectacular online fundraising early on, instead of through the old methods, that said, “I am a serious candidate.”

CG: What advice would you give up-and-coming copywriters to help them learn this trade?

Leon: This is a trade, a craft. And I think you learn best by working with someone who knows the craft. This could be working at an agency, or apprenticing to a successful copywriter, or a hands-on writing course, where you’re getting specific assignments which are critiqued by professionals. Writing, getting critiqued, then rewriting. This is how your skill grows. Studying and really analyzing controls in different industries is also extremely helpful.

CG: Tell us about your most outrageous client and how you dealt with it.

Leon: I remember working with this marketing consultant who had a very large client. He hired me to write the copy and to be in charge of the creative. He was off-the charts obsessive. He would send 50 page faxes in the middle of the night. I’m talking about 3:00 in the morning. At the time, I had a free-standing fax machine (I’ve since gone to computer-based), so I would hear the fax ring then the pages go on and on until it finally rang off. Sometimes he did this a few times in the middle of the night.

That was indicative of his obsessive, micro-management throughout the process. I dealt with it the best I could, got him toned down a bit. It was very good money, but once the assignment was done, I said, ”Adios.” And then slept a whole lot better.

CG: Tell us about the funniest copywriting experience you’ve had.

Leon: I was a copywriter working on the Johnson & Johnson account. At the time, I was working on their dental floss. We had a big focus group, and a whole bunch of us – client people, agency people – were behind the one-way mirror, watching the focus group. The focus group was finishing up. We were hungry and were gobbling up the sandwiches, standing close to the one way mirror watching the people file out of the room. One person didn’t file out right away. She went up to the mirror and opened up her mouth wide and started examining her gums, as we were inches in front of her on the other side of the mirror, our mouths full of food. Needless to say, we didn’t finish our sandwiches.

CG: Thanks so much, Leon, for joining us!